#------------------------------------------------------------------------------
#$Date: 2023-10-10 04:19:25 +0200 (Tue, 10 Oct 2023) $
#$Revision: 286864 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/28/2022892.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022892
loop_
_publ_author_name
'Rajendrakumar, Satyasree'
'Surampudi Venkata Sai Durga, Anuja'
'Balasubramanian, Sridhar'
_publ_section_title
;
Strategic synthon approach in obtaining cocrystals and cocrystal
polymorphs of a high-Z′ system deferiprone -- an anti-thalassemia
drug
;
_journal_coeditor_code LO5093
_journal_issue 6
_journal_name_full
'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials'
_journal_page_first 946
_journal_page_last 964
_journal_paper_doi 10.1107/S205252062100980X
_journal_volume 77
_journal_year 2021
_chemical_formula_moiety 'C7 H9 N O2, C6 H6 O2'
_chemical_formula_sum 'C13 H15 N O4'
_chemical_formula_weight 249.26
_chemical_name_common 'Deferiprone-Catechol (1:1) cocrystal'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2ybc'
_space_group_name_H-M_alt 'P 1 21/c 1'
_atom_sites_solution_hydrogens mixed
_audit_creation_method SHELXL-2018/3
_cell_angle_alpha 90
_cell_angle_beta 110.761(7)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 12.867(3)
_cell_length_b 9.550(2)
_cell_length_c 10.487(2)
_cell_measurement_reflns_used 6762
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.69
_cell_measurement_theta_min 2.71
_cell_volume 1205.0(4)
_computing_cell_refinement 'SAINT (Bruker, 2016)'
_computing_data_collection 'APEX3 (Bruker, 2016)'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution 'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method '\w and \f'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0712
_diffrn_reflns_av_unetI/netI 0.0475
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_number 2125
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full 24.986
_diffrn_reflns_theta_max 24.986
_diffrn_reflns_theta_min 2.723
_diffrn_source microfocus
_exptl_absorpt_coefficient_mu 0.102
_exptl_absorpt_correction_T_max 0.7461
_exptl_absorpt_correction_T_min 0.6862
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS, Bruker, 2016'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.374
_exptl_crystal_description block
_exptl_crystal_F_000 528
_exptl_crystal_size_max 0.260
_exptl_crystal_size_mid 0.240
_exptl_crystal_size_min 0.180
_refine_diff_density_max 0.376
_refine_diff_density_min -0.379
_refine_diff_density_rms 0.094
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.250
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 177
_refine_ls_number_reflns 2125
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.250
_refine_ls_R_factor_all 0.1106
_refine_ls_R_factor_gt 0.0863
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+5.1435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1940
_refine_ls_wR_factor_ref 0.2032
_reflns_Friedel_coverage 0.000
_reflns_number_gt 1755
_reflns_number_total 2125
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file lo5093sup1.cif
_cod_data_source_block KA1027_0m_4def-cat_1_1_form2
_cod_original_cell_volume 1205.1(5)
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 2022892
_shelx_shelxl_version_number 2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min 0.974
_shelx_estimated_absorpt_t_max 0.982
_shelx_res_file
;
TITL KA1027_0m_4_a.res in P2(1)/c
KA1027_0m_4.res
created by SHELXL-2018/3 at 15:13:47 on 10-Dec-2020
CELL 0.71073 12.8674 9.5503 10.4873 90.000 110.761 90.000
ZERR 4.00 0.0027 0.0021 0.0023 0.000 0.0073 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H O N
UNIT 52 60 16 4
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -173
MERG 2
BOND $H
EQIV $1 x, -y+1/2, z-1/2
EQIV $2 -x+1, y-1/2, -z+5/2
HTAB O1 O2
HTAB O1 O3
HTAB O3 O2_$1
HTAB O4 O2
HTAB O4 O3
HTAB C5 O2_$2
HTAB C6 O4_$2
SIZE 0.26 0.24 0.18
OMIT -3 50
ACTA
L.S. 20
FMAP 2
PLAN 5
WGHT 0.041000 5.143500
FVAR 0.88630
MOLE 1
C1 1 0.609250 0.166425 1.086588 11.00000 0.01635 0.01383 =
0.01144 0.00087 -0.00022 -0.00163
C2 1 0.499677 0.203621 1.056587 11.00000 0.01426 0.01368 =
0.01242 0.00053 0.00049 -0.00041
C3 1 0.431270 0.136114 1.119497 11.00000 0.01889 0.01507 =
0.00695 -0.00298 0.00001 0.00014
C4 1 0.482265 0.029943 1.212328 11.00000 0.02170 0.01700 =
0.01366 0.00041 0.00734 -0.00066
AFIX 43
H4 2 0.440667 -0.018518 1.257328 11.00000 -1.20000
AFIX 0
C5 1 0.590829 -0.005323 1.239454 11.00000 0.02307 0.01366 =
0.00725 0.00204 0.00034 0.00297
AFIX 43
H5 2 0.623165 -0.078582 1.302291 11.00000 -1.20000
AFIX 0
C6 1 0.770662 0.019740 1.210799 11.00000 0.01091 0.02399 =
0.01929 0.00173 -0.00021 0.00433
AFIX 137
H6A 2 0.779711 -0.020463 1.129388 11.00000 -1.50000
H6B 2 0.790890 -0.050254 1.283867 11.00000 -1.50000
H6C 2 0.818976 0.101786 1.240608 11.00000 -1.50000
AFIX 0
C7 1 0.679978 0.237761 1.020363 11.00000 0.01606 0.02631 =
0.02984 0.01332 0.00146 0.00235
AFIX 137
H7A 2 0.635731 0.308211 0.955960 11.00000 -1.50000
H7B 2 0.707886 0.168534 0.971404 11.00000 -1.50000
H7C 2 0.742808 0.283428 1.090196 11.00000 -1.50000
AFIX 0
O1 3 0.458694 0.309655 0.966953 11.00000 0.01358 0.02626 =
0.02992 0.01644 0.00447 0.00509
H1O 2 0.390819 0.310088 0.944844 11.00000 0.08131
O2 3 0.328382 0.174775 1.087888 11.00000 0.01449 0.02129 =
0.01609 0.00354 0.00332 0.00378
N1 4 0.653441 0.062272 1.178368 11.00000 0.01342 0.01582 =
0.01470 -0.00022 -0.00019 0.00166
MOLE 2
C8 1 0.172901 0.442351 0.769228 11.00000 0.00690 0.01736 =
0.01491 -0.00199 -0.00083 -0.00209
C9 1 0.134485 0.459755 0.876349 11.00000 0.01413 0.01493 =
0.01315 -0.00279 -0.00036 -0.00534
C10 1 0.059233 0.566071 0.870259 11.00000 0.01790 0.01936 =
0.02625 -0.00253 0.00942 -0.00040
AFIX 43
H10 2 0.033708 0.579797 0.943963 11.00000 -1.20000
AFIX 0
C11 1 0.021756 0.651273 0.757812 11.00000 0.01667 0.01786 =
0.03143 0.00116 0.00528 0.00351
AFIX 43
H11 2 -0.029763 0.723678 0.754502 11.00000 -1.20000
AFIX 0
C12 1 0.057684 0.633591 0.649122 11.00000 0.02099 0.01926 =
0.02597 0.00702 0.00064 0.00242
AFIX 43
H12 2 0.030612 0.692229 0.571093 11.00000 -1.20000
AFIX 0
C13 1 0.134680 0.527625 0.656455 11.00000 0.01960 0.02382 =
0.01908 0.00104 0.00483 -0.00095
AFIX 43
H13 2 0.160714 0.514500 0.583096 11.00000 -1.20000
AFIX 0
O3 3 0.248453 0.336189 0.782597 11.00000 0.01797 0.01908 =
0.01336 0.00222 0.00424 0.00550
H3O 2 0.267880 0.343232 0.703917 11.00000 0.01722
O4 3 0.167544 0.374086 0.988434 11.00000 0.02435 0.02480 =
0.01529 0.00409 0.00642 0.00746
H4O 2 0.210608 0.304552 0.974818 11.00000 0.06473
HKLF 4 1 1 0 0 0 1 0 0 0 1
REM KA1027_0m_4_a.res in P2(1)/c
REM wR2 = 0.2032, GooF = S = 1.250, Restrained GooF = 1.250 for all data
REM R1 = 0.0863 for 1755 Fo > 4sig(Fo) and 0.1106 for all 2125 data
REM 177 parameters refined using 0 restraints
END
WGHT 0.0417 5.0023
REM Highest difference peak 0.376, deepest hole -0.379, 1-sigma level 0.094
Q1 1 0.7651 -0.1591 1.2746 11.00000 0.05 0.38
Q2 1 0.1874 0.2039 1.0208 11.00000 0.05 0.34
Q3 1 0.6322 -0.0093 1.3414 11.00000 0.05 0.33
Q4 1 0.0364 0.5725 1.0178 11.00000 0.05 0.33
Q5 1 0.8197 -0.1719 1.2137 11.00000 0.05 0.33
;
_shelx_res_checksum 78728
_shelx_hkl_file
;
0 0 2 911.62 18.61
0 0 3 0.10 0.68
0 0 4 1054.69 23.27
0 0 5 0.41 1.56
0 0 6 222.13 14.26
0 0 7 9.13 3.37
0 0 8 294.90 12.10
0 0 9 5.76 5.22
0 0 10 79.17 155.49
0 0 11 0.75 6.11
0 0 12 52.39 14.94
0 0 13 19.78 12.90
0 0 14 46.90 205.85
0 -1 1 156.30 2.33
0 -1 2 1133.44 16.28
0 -1 3 2678.07 36.92
0 -1 4 690.78 10.37
0 -1 5 4.39 0.90
0 -1 6 215.09 9.17
0 -1 7 235.85 7.47
0 -1 8 225.44 5.01
0 -1 9 182.50 5.92
0 -1 10 193.54 69.81
0 -1 11 84.60 9.15
0 -1 12 59.41 9.24
0 -1 13 93.33 10.10
0 -1 14 116.00 19.71
0 -2 0 605.84 66.18
0 -2 1 2418.28 50.84
0 -2 2 9957.55 205.26
0 -2 3 735.79 11.24
0 -2 4 169.08 3.07
0 -2 5 1079.91 15.87
0 -2 6 149.16 3.72
0 -2 7 10.60 2.04
0 -2 8 118.50 6.04
0 -2 9 122.98 4.86
0 -2 10 2.29 75.03
0 -2 11 273.49 12.28
0 -2 12 60.99 10.04
0 -2 13 72.23 8.69
0 -3 0 0.00 1.70
0 -3 1 118.49 5.22
0 -3 2 15.08 0.90
0 -3 3 22.33 1.14
0 -3 4 276.52 4.47
0 -3 5 4917.20 68.68
0 -3 6 0.34 2.11
0 -3 7 110.26 14.23
0 -3 8 31.79 2.81
0 -3 9 62.31 4.37
0 -3 10 26.36 6.16
0 -3 11 105.15 9.45
0 -3 12 85.35 10.03
0 -3 13 98.43 9.43
0 -4 0 22.20 5.41
0 -4 1 3.77 13.11
0 -4 2 355.40 7.00
0 -4 3 3075.86 50.84
0 -4 4 49.25 1.40
0 -4 5 285.90 5.10
0 -4 6 17.68 2.13
0 -4 7 25.31 4.77
0 -4 8 81.02 3.05
0 -4 9 4.69 4.81
0 -4 10 95.69 7.94
0 -4 11 22.20 6.90
0 -4 12 94.26 11.46
0 -4 13 65.27 10.56
0 -5 0 2.95 3.74
0 -5 1 484.32 24.60
0 -5 2 4.02 1.94
0 -5 3 2.79 0.95
0 -5 4 535.08 9.96
0 -5 5 7.04 1.09
0 -5 6 900.77 21.98
0 -5 7 151.54 4.02
0 -5 8 169.55 4.26
0 -5 9 72.17 6.36
0 -5 10 57.78 5.41
0 -5 11 10.23 10.67
0 -5 12 45.22 10.99
0 -5 13 193.96 13.33
0 -6 0 2480.14 267.68
0 -6 1 644.79 30.83
0 -6 2 112.52 5.63
0 -6 3 17.85 1.14
0 -6 4 90.55 2.71
0 -6 5 216.19 6.93
0 -6 6 550.65 20.96
0 -6 7 106.88 10.54
0 -6 8 24.48 3.33
0 -6 9 18.69 4.07
0 -6 10 13.69 11.16
0 -6 11 21.93 8.98
0 -6 12 124.63 16.32
0 -7 0 0.00 4.73
0 -7 1 50.17 7.33
0 -7 2 24.49 9.03
0 -7 3 363.05 8.33
0 -7 4 15.71 2.70
0 -7 5 235.51 8.33
0 -7 6 16.71 7.87
0 -7 7 16.62 4.06
0 -7 8 191.42 9.11
0 -7 9 78.85 27.00
0 -7 10 224.17 12.17
0 -7 11 173.03 321.99
0 -7 12 146.39 23.73
0 -8 0 171.33 22.35
0 -8 1 168.94 12.82
0 -8 2 0.00 12.75
0 -8 3 2.75 2.86
0 -8 4 75.85 3.20
0 -8 5 16.61 6.13
0 -8 6 63.82 12.50
0 -8 7 118.48 7.53
0 -8 8 201.69 12.95
0 -8 9 176.20 14.52
0 -8 10 53.66 15.93
0 -8 11 235.34 361.44
0 -9 0 4.80 7.32
0 -9 1 3.16 9.02
0 -9 2 90.28 13.38
0 -9 3 44.31 6.10
0 -9 4 0.59 1.62
0 -9 5 110.50 5.47
0 -9 6 144.83 6.48
0 -9 7 12.01 6.33
0 -9 8 59.29 21.91
0 -9 9 250.15 16.53
0 -9 10 146.41 17.63
0 -10 0 302.78 37.50
0 -10 1 51.00 11.34
0 -10 2 183.05 12.38
0 -10 3 24.36 12.04
0 -10 4 46.35 2.87
0 -10 5 11.14 5.22
0 -10 6 30.83 8.50
0 -10 7 10.11 8.54
0 -10 8 57.74 10.72
0 -10 9 71.05 13.75
0 -11 0 4.07 9.63
0 -11 1 0.00 19.14
0 -11 2 127.02 21.69
0 -11 3 8.44 15.02
0 -11 4 49.70 7.26
0 -11 5 99.66 7.84
0 -11 6 186.55 12.10
0 -11 7 63.71 12.65
0 -11 8 154.95 15.89
0 -12 0 21.77 12.08
0 -12 1 11.67 12.67
0 -12 2 6.84 15.05
0 -12 3 5.85 18.62
0 -12 4 46.98 15.91
0 -12 5 49.03 192.09
0 -12 6 164.68 30.71
0 -13 0 0.00 12.54
0 -13 1 30.56 15.22
0 -13 2 42.98 24.96
0 -13 3 55.29 31.65
0 -13 4 23.52 199.27
1 0 -14 66.79 11.50
1 0 -13 30.96 12.93
1 0 -12 56.11 14.20
1 0 -11 1.02 6.75
1 0 -10 888.07 111.30
1 0 -9 0.00 5.87
1 0 -8 823.56 23.32
1 0 -7 0.00 3.55
1 0 -6 282.90 7.90
1 0 -5 1.22 1.04
1 0 -4 36.48 1.79
1 0 -3 0.16 0.82
1 0 -2 4482.38 120.21
1 0 -1 3.89 5.71
1 0 1 0.29 0.35
1 0 2 122.98 2.99
1 0 3 0.37 0.64
1 0 4 1578.14 30.81
1 0 5 0.46 1.03
1 0 6 2907.69 68.01
1 0 7 7.34 3.13
1 0 8 177.90 6.73
1 0 9 0.00 7.05
1 0 10 196.74 15.98
1 0 11 0.00 12.74
1 0 12 57.65 14.87
1 0 13 27.58 11.84
1 -1 -14 64.17 7.47
1 -1 -13 45.78 9.10
1 -1 -12 0.00 27.55
1 -1 -11 47.66 6.21
1 -1 -10 10.84 9.86
1 -1 -9 34.67 3.43
1 -1 -8 10.98 2.38
1 -1 -7 13.03 2.98
1 -1 -6 371.96 10.27
1 -1 -5 1.12 0.80
1 -1 -4 448.20 7.66
1 -1 -3 2322.95 32.83
1 -1 -2 1502.43 22.49
1 -1 -1 308.57 4.48
1 -1 0 1657.43 92.17
1 -1 1 3420.72 73.39
1 -1 2 2583.30 37.39
1 -1 3 25.10 0.87
1 -1 4 31.22 1.18
1 -1 5 3.24 0.81
1 -1 6 25.25 4.17
1 -1 7 362.19 7.51
1 -1 8 120.29 3.91
1 -1 9 1033.63 28.35
1 -1 10 149.71 11.26
1 -1 11 3.91 6.15
1 -1 12 21.70 8.77
1 -1 13 60.17 8.44
1 -2 -14 40.68 10.67
1 -2 -13 99.43 10.21
1 -2 -12 35.14 10.69
1 -2 -11 5.45 4.66
1 -2 -10 31.88 10.36
1 -2 -9 36.80 4.30
1 -2 -8 160.81 7.21
1 -2 -7 36.45 6.68
1 -2 -6 57.53 2.57
1 -2 -5 1757.08 27.39
1 -2 -4 203.70 3.81
1 -2 -3 1675.70 26.03
1 -2 -2 2192.38 29.35
1 -2 -1 1004.42 19.97
1 -2 0 1852.91 101.80
1 -2 1 9999.00 257.85
1 -2 2 6008.70 111.23
1 -2 3 853.94 12.61
1 -2 4 1349.84 19.49
1 -2 5 1726.39 25.97
1 -2 6 13.30 2.53
1 -2 7 19.36 5.11
1 -2 8 135.64 3.79
1 -2 9 89.64 4.94
1 -2 10 46.13 20.17
1 -2 11 26.76 9.07
1 -2 12 79.69 9.57
1 -2 13 83.05 8.82
1 -3 -13 21.09 11.15
1 -3 -12 21.31 9.49
1 -3 -11 21.44 9.88
1 -3 -10 64.44 8.43
1 -3 -9 13.46 5.96
1 -3 -8 275.10 6.68
1 -3 -7 30.14 2.24
1 -3 -6 0.00 2.67
1 -3 -5 1927.49 28.74
1 -3 -4 10.80 0.74
1 -3 -3 515.51 8.08
1 -3 -2 1491.43 24.62
1 -3 -1 935.45 22.63
1 -3 0 195.58 14.23
1 -3 1 2493.46 71.47
1 -3 2 17.26 1.22
1 -3 3 21.78 0.80
1 -3 4 1443.15 20.85
1 -3 5 3.15 0.85
1 -3 6 30.04 2.29
1 -3 7 5.23 2.10
1 -3 8 131.21 3.88
1 -3 9 39.15 4.78
1 -3 10 9.33 8.49
1 -3 11 263.26 13.67
1 -3 12 58.16 9.34
1 -3 13 86.80 10.22
1 -4 -13 96.92 9.77
1 -4 -12 9.94 10.02
1 -4 -11 5.46 5.63
1 -4 -10 12.48 11.79
1 -4 -9 0.00 4.77
1 -4 -8 9.98 2.56
1 -4 -7 56.64 2.57
1 -4 -6 13.84 2.11
1 -4 -5 746.61 12.08
1 -4 -4 1282.12 19.24
1 -4 -3 0.47 0.81
1 -4 -2 2.04 0.97
1 -4 -1 521.96 16.81
1 -4 0 746.90 56.76
1 -4 1 31.41 5.00
1 -4 2 452.24 9.38
1 -4 3 2001.09 32.20
1 -4 4 897.30 13.54
1 -4 5 1245.52 18.21
1 -4 6 19.27 2.54
1 -4 7 114.12 16.89
1 -4 8 29.64 3.12
1 -4 9 37.61 5.85
1 -4 10 182.96 13.10
1 -4 11 182.86 19.12
1 -4 12 54.51 9.55
1 -4 13 49.83 12.74
1 -5 -13 109.57 9.72
1 -5 -12 64.87 11.73
1 -5 -11 13.10 8.61
1 -5 -10 26.61 5.13
1 -5 -9 48.21 4.73
1 -5 -8 42.67 3.54
1 -5 -7 273.11 8.14
1 -5 -6 38.65 2.88
1 -5 -5 12.85 1.31
1 -5 -4 648.58 12.24
1 -5 -3 297.51 6.33
1 -5 -2 230.64 6.07
1 -5 -1 78.50 17.25
1 -5 0 1529.73 77.23
1 -5 1 62.37 7.31
1 -5 2 20.28 1.90
1 -5 3 0.95 0.81
1 -5 4 49.87 1.97
1 -5 5 111.17 3.45
1 -5 6 882.33 14.77
1 -5 7 154.20 4.62
1 -5 8 85.95 8.19
1 -5 9 18.27 4.42
1 -5 10 131.37 8.06
1 -5 11 63.09 10.34
1 -5 12 122.07 11.59
1 -6 -12 74.37 19.48
1 -6 -11 56.36 8.40
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14 -5 -4 19.46 5.13
14 -5 -3 0.00 9.15
14 -5 -2 18.10 6.45
14 -5 -1 1.50 4.53
14 -5 0 0.39 2.96
14 -5 1 0.00 5.84
14 -5 2 0.00 9.42
14 -5 3 0.82 3.56
14 -6 -10 54.10 20.99
14 -6 -9 46.04 12.41
14 -6 -8 0.00 13.10
14 -6 -7 4.41 7.73
14 -6 -6 17.47 10.68
14 -6 -5 8.30 9.03
14 -6 -4 22.62 3.47
14 -6 -3 27.05 9.89
14 -6 -2 54.95 7.00
14 -6 -1 0.00 6.15
14 -6 0 40.98 5.51
14 -6 1 10.47 11.29
14 -6 2 41.93 8.30
14 -7 -9 306.21 16.71
14 -7 -8 57.88 9.43
14 -7 -7 0.93 8.67
14 -7 -6 58.07 11.55
14 -7 -5 0.00 11.20
14 -7 -4 5.51 5.54
14 -7 -3 0.00 13.26
14 -7 -2 7.82 9.37
14 -7 -1 0.00 6.42
14 -7 0 36.60 5.45
14 -7 1 0.00 6.35
14 -8 -8 7.16 11.26
14 -8 -7 76.13 13.14
14 -8 -6 20.85 13.78
14 -8 -5 10.87 12.20
14 -8 -4 0.00 15.36
14 -8 -3 17.94 12.81
14 -8 -2 77.39 10.57
14 -8 -1 0.00 8.00
15 0 -12 0.00 23.92
15 0 -11 4.78 11.01
15 0 -10 72.75 18.85
15 0 -9 1.69 10.78
15 0 -8 0.00 27.79
15 0 -7 2.96 9.81
15 0 -6 88.17 11.85
15 0 -5 0.00 9.51
15 0 -4 176.90 10.19
15 0 -3 0.00 14.09
15 0 -2 35.84 13.79
15 0 -1 0.00 10.92
15 0 0 24.89 5.81
15 0 1 0.00 11.79
15 0 2 0.71 8.86
15 -1 -12 33.57 23.92
15 -1 -11 82.66 7.94
15 -1 -10 0.00 10.77
15 -1 -9 46.76 7.94
15 -1 -8 60.37 8.06
15 -1 -7 0.07 5.85
15 -1 -6 18.99 5.69
15 -1 -5 59.85 8.58
15 -1 -4 60.59 3.99
15 -1 -3 0.00 6.26
15 -1 -2 60.09 7.05
15 -1 -1 43.81 5.51
15 -1 0 2.00 3.01
15 -1 1 32.58 5.26
15 -1 2 3.58 7.55
15 -1 3 0.00 218.52
15 -2 -12 55.74 5.44
15 -2 -11 0.00 17.35
15 -2 -10 23.26 10.71
15 -2 -9 233.47 16.95
15 -2 -8 0.00 5.56
15 -2 -7 6.08 5.52
15 -2 -6 15.58 6.50
15 -2 -5 0.00 8.93
15 -2 -4 100.81 6.29
15 -2 -3 8.02 6.69
15 -2 -2 2.39 5.69
15 -2 -1 39.50 6.01
15 -2 0 3.23 3.16
15 -2 1 0.00 8.47
15 -2 2 0.00 13.42
15 -2 3 0.00 243.82
15 -3 -11 0.00 23.78
15 -3 -10 0.00 10.99
15 -3 -9 62.65 10.95
15 -3 -8 17.26 5.66
15 -3 -7 55.32 6.14
15 -3 -6 82.78 7.13
15 -3 -5 11.49 7.21
15 -3 -4 81.95 5.67
15 -3 -3 12.54 8.22
15 -3 -2 0.00 6.22
15 -3 -1 2.35 4.93
15 -3 0 11.16 3.73
15 -3 1 15.44 5.55
15 -3 2 0.00 8.67
15 -3 3 9.36 9.95
15 -4 -11 7.67 9.50
15 -4 -10 0.00 13.24
15 -4 -9 0.00 9.94
15 -4 -8 236.27 11.68
15 -4 -7 53.60 6.01
15 -4 -6 36.34 7.17
15 -4 -5 0.67 7.37
15 -4 -4 0.00 8.53
15 -4 -3 8.06 8.05
15 -4 -2 13.31 7.08
15 -4 -1 0.00 5.14
15 -4 0 15.65 4.15
15 -4 1 100.99 7.44
15 -4 2 0.00 11.19
15 -5 -10 5.18 12.55
15 -5 -9 2.08 11.79
15 -5 -8 0.00 10.75
15 -5 -7 11.23 6.28
15 -5 -6 0.30 6.76
15 -5 -5 166.68 9.55
15 -5 -4 134.05 9.16
15 -5 -3 0.00 7.10
15 -5 -2 0.00 6.47
15 -5 -1 0.94 6.14
15 -5 0 12.59 3.65
15 -5 1 0.27 6.11
15 -5 2 3.48 6.05
15 -6 -9 0.00 12.33
15 -6 -8 27.73 7.99
15 -6 -7 26.23 8.24
15 -6 -6 14.02 9.86
15 -6 -5 87.55 9.94
15 -6 -4 11.37 4.93
15 -6 -3 0.00 11.13
15 -6 -2 3.16 12.56
15 -6 -1 0.00 7.92
15 -6 0 3.23 3.56
15 -6 1 0.19 3.94
15 -7 -8 7.18 9.36
15 -7 -7 20.73 10.64
15 -7 -6 0.00 18.46
15 -7 -5 0.00 12.45
15 -7 -4 32.20 5.95
15 -7 -3 10.53 14.12
15 -7 -2 0.00 7.76
15 -7 -1 40.52 6.81
16 0 -11 0.00 6.98
16 0 -10 98.17 17.26
16 0 -9 17.73 10.92
16 0 -8 16.71 9.81
16 0 -7 0.00 11.16
16 0 -6 4.33 10.43
16 0 -5 0.00 12.61
16 0 -4 385.55 15.86
16 0 -3 0.00 16.26
16 0 -2 0.00 14.36
16 0 -1 0.00 12.02
16 0 0 36.88 6.38
16 0 2 16.81 4.25
16 -1 -11 14.65 6.48
16 -1 -10 12.94 13.13
16 -1 -9 17.60 7.73
16 -1 -8 137.29 8.27
16 -1 -7 42.81 6.34
16 -1 -6 9.26 8.75
16 -1 -5 33.09 11.86
16 -1 -4 340.93 12.03
16 -1 -3 80.92 9.24
16 -1 -2 0.00 7.59
16 -1 -1 0.00 5.35
16 -1 0 13.49 3.78
16 -1 1 4.43 5.00
16 -1 2 4.88 2.93
16 -2 -11 17.36 10.53
16 -2 -10 0.00 12.60
16 -2 -9 19.06 7.92
16 -2 -8 113.42 8.27
16 -2 -7 28.72 6.05
16 -2 -6 98.28 7.39
16 -2 -5 13.61 7.66
16 -2 -4 108.62 7.44
16 -2 -3 13.30 7.03
16 -2 -2 22.68 6.30
16 -2 -1 0.80 7.11
16 -2 0 28.83 4.10
16 -2 1 0.87 7.88
16 -2 2 4.43 9.23
16 -3 -10 4.16 10.26
16 -3 -9 0.00 11.13
16 -3 -8 9.38 6.00
16 -3 -7 27.10 6.14
16 -3 -6 143.01 8.10
16 -3 -5 72.37 8.96
16 -3 -4 51.35 7.22
16 -3 -3 8.31 7.46
16 -3 -2 8.10 6.39
16 -3 -1 24.53 6.19
16 -3 0 2.13 3.59
16 -3 1 62.88 8.32
16 -4 -10 20.67 13.00
16 -4 -9 4.85 8.67
16 -4 -8 15.40 6.60
16 -4 -7 8.69 8.79
16 -4 -6 7.57 8.75
16 -4 -5 26.83 7.70
16 -4 -4 0.00 13.02
16 -4 -3 13.17 7.30
16 -4 -2 105.78 8.52
16 -4 -1 79.37 7.49
16 -4 0 3.14 3.70
16 -4 1 56.87 4.29
16 -5 -9 15.17 16.05
16 -5 -8 68.42 9.06
16 -5 -7 0.00 9.61
16 -5 -6 13.42 8.62
16 -5 -5 12.87 13.17
16 -5 -4 16.78 6.41
16 -5 -3 9.55 9.30
16 -5 -2 14.59 10.64
16 -5 -1 34.03 6.58
16 -5 0 0.00 3.94
16 -6 -7 98.40 10.97
16 -6 -6 0.00 11.03
16 -6 -5 70.99 16.48
16 -6 -4 8.52 6.18
16 -6 -3 0.00 15.56
16 -6 -2 10.97 10.34
17 0 -10 6.76 21.01
17 0 -9 0.30 112.42
17 0 -8 59.71 10.90
17 0 -7 4.49 11.12
17 0 -6 155.77 13.20
17 0 -5 0.35 133.69
17 0 -4 13.24 6.62
17 0 -3 0.00 118.39
17 0 -2 40.96 10.05
17 0 0 6.18 6.73
17 -1 -10 0.00 15.75
17 -1 -9 19.26 7.59
17 -1 -8 6.16 9.02
17 -1 -7 40.02 7.09
17 -1 -6 14.25 16.20
17 -1 -5 0.00 8.70
17 -1 -4 0.00 20.66
17 -1 -3 6.80 8.26
17 -1 -2 4.71 9.07
17 -1 -1 30.03 5.44
17 -1 0 0.00 7.13
17 -2 -9 15.18 9.44
17 -2 -8 25.28 6.06
17 -2 -7 12.65 7.36
17 -2 -6 0.00 12.30
17 -2 -5 8.54 11.27
17 -2 -4 29.82 9.96
17 -2 -3 229.18 10.60
17 -2 -2 0.53 16.37
17 -2 -1 7.72 7.19
17 -2 0 226.75 14.64
17 -3 -9 29.96 16.02
17 -3 -8 15.01 6.46
17 -3 -7 22.23 6.12
17 -3 -6 18.37 7.68
17 -3 -5 10.93 7.60
17 -3 -4 6.46 7.27
17 -3 -3 8.02 9.32
17 -3 -2 18.50 8.87
17 -3 -1 94.92 8.68
17 -4 -8 0.31 8.90
17 -4 -7 114.75 7.59
17 -4 -6 31.74 7.04
17 -4 -5 13.42 18.70
17 -4 -4 15.19 20.52
17 -4 -3 46.99 9.80
17 -4 -2 60.74 12.63
17 -5 -6 49.58 4.23
17 -5 -5 1.94 3.46
17 -5 -4 14.58 5.23
18 0 -8 45.43 15.25
18 0 -7 0.00 99.40
18 0 -6 47.02 17.26
18 0 -4 4.69 8.16
18 -1 -8 37.17 15.32
18 -1 -7 33.46 9.54
18 -1 -6 10.44 18.01
18 -1 -5 14.79 133.39
18 -1 -4 0.00 4.40
18 -1 -3 0.00 126.20
18 -2 -7 0.00 106.69
18 -2 -6 0.00 121.02
18 -2 -5 61.29 4.28
18 -2 -4 118.93 6.42
18 -2 -3 0.00 140.82
0 0 0 0.00 0.00
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
;
_shelx_hkl_checksum 85410
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6092(3) 0.1664(4) 1.0866(4) 0.0153(9) Uani 1 1 d . . . . .
C2 C 0.4997(3) 0.2036(4) 1.0566(4) 0.0146(9) Uani 1 1 d . . . . .
C3 C 0.4313(3) 0.1361(4) 1.1195(4) 0.0149(9) Uani 1 1 d . . . . .
C4 C 0.4823(3) 0.0299(4) 1.2123(4) 0.0172(9) Uani 1 1 d . . . . .
H4 H 0.440667 -0.018518 1.257328 0.021 Uiso 1 1 calc R U . . .
C5 C 0.5908(3) -0.0053(4) 1.2395(4) 0.0160(9) Uani 1 1 d . . . . .
H5 H 0.623165 -0.078582 1.302291 0.019 Uiso 1 1 calc R U . . .
C6 C 0.7707(3) 0.0197(5) 1.2108(4) 0.0196(10) Uani 1 1 d . . . . .
H6A H 0.779711 -0.020463 1.129388 0.029 Uiso 1 1 calc R U . . .
H6B H 0.790890 -0.050254 1.283867 0.029 Uiso 1 1 calc R U . . .
H6C H 0.818976 0.101786 1.240608 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6800(4) 0.2378(5) 1.0204(5) 0.0259(11) Uani 1 1 d . . . . .
H7A H 0.635731 0.308211 0.955960 0.039 Uiso 1 1 calc R U . . .
H7B H 0.707886 0.168534 0.971404 0.039 Uiso 1 1 calc R U . . .
H7C H 0.742808 0.283428 1.090196 0.039 Uiso 1 1 calc R U . . .
O1 O 0.4587(3) 0.3097(3) 0.9670(3) 0.0241(8) Uani 1 1 d . . . . .
H1O H 0.391(7) 0.310(8) 0.945(8) 0.08(3) Uiso 1 1 d . . . . .
O2 O 0.3284(2) 0.1748(3) 1.0879(3) 0.0179(7) Uani 1 1 d . . . . .
N1 N 0.6534(3) 0.0623(4) 1.1784(3) 0.0160(8) Uani 1 1 d . . . . .
C8 C 0.1729(3) 0.4424(4) 0.7692(4) 0.0143(9) Uani 1 1 d . . . . .
C9 C 0.1345(3) 0.4598(4) 0.8763(4) 0.0155(9) Uani 1 1 d . . . . .
C10 C 0.0592(4) 0.5661(5) 0.8703(5) 0.0207(10) Uani 1 1 d . . . . .
H10 H 0.033708 0.579797 0.943963 0.025 Uiso 1 1 calc R U . . .
C11 C 0.0218(4) 0.6513(5) 0.7578(5) 0.0229(10) Uani 1 1 d . . . . .
H11 H -0.029763 0.723678 0.754502 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0577(4) 0.6336(5) 0.6491(5) 0.0241(10) Uani 1 1 d . . . . .
H12 H 0.030612 0.692229 0.571093 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1347(4) 0.5276(5) 0.6565(4) 0.0214(10) Uani 1 1 d . . . . .
H13 H 0.160714 0.514500 0.583096 0.026 Uiso 1 1 calc R U . . .
O3 O 0.2485(2) 0.3362(3) 0.7826(3) 0.0172(7) Uani 1 1 d . . . . .
H3O H 0.268(4) 0.343(5) 0.704(5) 0.017(12) Uiso 1 1 d . . . . .
O4 O 0.1675(3) 0.3741(3) 0.9884(3) 0.0216(7) Uani 1 1 d . . . . .
H4O H 0.211(6) 0.305(7) 0.975(7) 0.06(2) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.016(2) 0.014(2) 0.011(2) 0.0009(16) -0.0002(16) -0.0016(16)
C2 0.014(2) 0.014(2) 0.012(2) 0.0005(16) 0.0005(16) -0.0004(16)
C3 0.019(2) 0.015(2) 0.0070(19) -0.0030(16) 0.0000(16) 0.0001(16)
C4 0.022(2) 0.017(2) 0.014(2) 0.0004(16) 0.0073(18) -0.0007(17)
C5 0.023(2) 0.014(2) 0.0073(19) 0.0020(16) 0.0003(17) 0.0030(17)
C6 0.011(2) 0.024(2) 0.019(2) 0.0017(18) -0.0002(17) 0.0043(17)
C7 0.016(2) 0.026(2) 0.030(3) 0.013(2) 0.0015(19) 0.0024(19)
O1 0.0136(16) 0.0263(18) 0.0299(18) 0.0164(14) 0.0045(14) 0.0051(13)
O2 0.0145(15) 0.0213(16) 0.0161(15) 0.0035(12) 0.0033(12) 0.0038(12)
N1 0.0134(18) 0.0158(18) 0.0147(18) -0.0002(14) -0.0002(14) 0.0017(14)
C8 0.0069(19) 0.017(2) 0.015(2) -0.0020(16) -0.0008(16) -0.0021(15)
C9 0.014(2) 0.015(2) 0.013(2) -0.0028(16) -0.0004(16) -0.0053(16)
C10 0.018(2) 0.019(2) 0.026(2) -0.0025(19) 0.0094(19) -0.0004(17)
C11 0.017(2) 0.018(2) 0.031(3) 0.0012(19) 0.0053(19) 0.0035(17)
C12 0.021(2) 0.019(2) 0.026(2) 0.0070(19) 0.0006(19) 0.0024(18)
C13 0.020(2) 0.024(2) 0.019(2) 0.0010(18) 0.0048(18) -0.0009(18)
O3 0.0180(15) 0.0191(16) 0.0134(15) 0.0022(12) 0.0042(12) 0.0055(12)
O4 0.0244(17) 0.0248(17) 0.0153(16) 0.0041(13) 0.0064(13) 0.0075(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 119.2(4) . . ?
N1 C1 C7 119.5(4) . . ?
C2 C1 C7 121.3(4) . . ?
O1 C2 C1 117.8(4) . . ?
O1 C2 C3 120.4(4) . . ?
C1 C2 C3 121.8(4) . . ?
O2 C3 C4 124.6(4) . . ?
O2 C3 C2 119.6(4) . . ?
C4 C3 C2 115.8(4) . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 O1 H1O 108(6) . . ?
C5 N1 C1 120.8(3) . . ?
C5 N1 C6 119.2(3) . . ?
C1 N1 C6 120.0(4) . . ?
C13 C8 O3 123.2(4) . . ?
C13 C8 C9 120.2(4) . . ?
O3 C8 C9 116.5(4) . . ?
O4 C9 C8 122.1(4) . . ?
O4 C9 C10 118.4(4) . . ?
C8 C9 C10 119.5(4) . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 118.7(4) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C8 C13 C12 120.4(4) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C8 O3 H3O 105(3) . . ?
C9 O4 H4O 109(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.361(5) . ?
C1 C2 1.378(6) . ?
C1 C7 1.491(6) . ?
C2 O1 1.355(5) . ?
C2 C3 1.427(6) . ?
C3 O2 1.299(5) . ?
C3 C4 1.398(6) . ?
C4 C5 1.365(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.357(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.481(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1 H1O 0.82(8) . ?
C8 C13 1.375(6) . ?
C8 O3 1.377(5) . ?
C8 C9 1.388(6) . ?
C9 O4 1.370(5) . ?
C9 C10 1.389(6) . ?
C10 C11 1.372(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O3 H3O 0.95(5) . ?
O4 H4O 0.91(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O O2 0.82(8) 2.33(8) 2.754(4) 113(6) . yes
O1 H1O O3 0.82(8) 2.03(8) 2.723(4) 142(7) . yes
O3 H3O O2 0.95(5) 1.67(5) 2.594(4) 165(4) 4_565 yes
O4 H4O O2 0.91(7) 1.99(7) 2.732(4) 138(6) . yes
O4 H4O O3 0.91(7) 2.26(7) 2.733(4) 112(5) . yes
C5 H5 O2 0.95 2.60 3.516(5) 162.2 2_647 yes
C6 H6B O4 0.98 2.37 3.277(5) 154.1 2_647 yes
_cod_database_fobs_code 2022892