#------------------------------------------------------------------------------
#$Date: 2023-12-07 12:51:05 +0100 (Thu, 07 Dec 2023) $
#$Revision: 288145 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/29/2022933.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_2022933
loop_
_publ_author_name
'Baletska, Sofiia'
'Techert, Simone'
'Velazquez-Garcia, Jose de Jesus'
_publ_section_title
;
Crystal structure of 2-methyl-1H-imidazol-3-ium
3,5-di-carb-oxy-benzoate.
;
_journal_coeditor_code JQ2031
_journal_issue 'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first 1088
_journal_page_last 1092
_journal_paper_doi 10.1107/S2056989023009209
_journal_volume 79
_journal_year 2023
_chemical_formula_iupac 'C4 H7 N2 +, C9 H5 O6 -'
_chemical_formula_moiety 'C4 H7 N2 +, C9 H5 O6 -'
_chemical_formula_sum 'C13 H12 N2 O6'
_chemical_formula_weight 292.25
_chemical_name_systematic
;
2-Methyl-1H-imidazol-3-ium 3,5-dicarboxybenzoate
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_Hall '-C 2yc'
_space_group_name_H-M_alt 'C 1 2/c 1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha 90
_cell_angle_beta 99.481(8)
_cell_angle_gamma 90
_cell_formula_units_Z 8
_cell_length_a 24.0655(18)
_cell_length_b 3.7704(3)
_cell_length_c 27.4258(19)
_cell_measurement_reflns_used 2955
_cell_measurement_temperature 100.00
_cell_measurement_theta_max 30.35
_cell_measurement_theta_min 2.46
_cell_volume 2454.5(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Bruker APEX Duo CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0741
_diffrn_reflns_av_unetI/netI 0.0361
_diffrn_reflns_limit_h_max 30
_diffrn_reflns_limit_h_min -30
_diffrn_reflns_limit_k_max 4
_diffrn_reflns_limit_k_min -4
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_number 23840
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.432
_diffrn_reflns_theta_min 2.088
_diffrn_source_current 0.6
_diffrn_source_power 0.03
_diffrn_source_voltage 50.0
_exptl_absorpt_coefficient_mu 0.127
_exptl_absorpt_correction_T_max 0.7454
_exptl_absorpt_correction_T_min 0.6277
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour 'clear light colourless'
_exptl_crystal_density_diffrn 1.582
_exptl_crystal_description block
_exptl_crystal_F_000 1216
_exptl_crystal_size_max 0.1
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.235
_refine_diff_density_min -0.275
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 204
_refine_ls_number_reflns 2531
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 1.035
_refine_ls_R_factor_all 0.0566
_refine_ls_R_factor_gt 0.0392
_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^)+(0.0457P)^2^+3.1540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0931
_refine_ls_wR_factor_ref 0.1029
_reflns_number_gt 1969
_reflns_number_total 2531
_reflns_threshold_expression 'I > 2\s(I)'
_iucr_refine_instructions_details
;
TITL mim_btc_100k_c2_2_a.res in C2/c
mim_btc_100k_c2_2.res
created by SHELXL-2018/3 at 14:03:25 on 28-Sep-2023
REM Old TITL mim_btc_100k_c2_2_a.res in C2/c
REM SHELXT solution in C2/c: R1 0.106, Rweak 0.003, Alpha 0.019
REM 0.307 for 400 systematic absences, Orientation as input
REM Formula found by SHELXT: C13 N2 O6
CELL 0.71073 24.0655 3.7704 27.4258 90 99.481 90
ZERR 8 0.0018 0.0003 0.0019 0 0.008 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 104 96 16 48
SADI C13 H13a C13 H13d
SADI C13 H13b C13 H13f
SADI C13 H13c C13 H13e
L.S. 20 0 0
PLAN 5
SIZE 0.03 0.1 0.1
TEMP -173.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
OMIT 0 0 2
REM
REM
REM
WGHT 0.045700 3.154000
FVAR 0.35279 0.47131
O5 4 0.212430 1.019425 0.293856 11.00000 0.01152 0.02753 =
0.00965 0.00132 -0.00238 -0.00266
AFIX 147
H5 2 0.178804 0.950516 0.290143 11.00000 -1.50000
AFIX 0
O4 4 0.390144 1.297331 0.228952 11.00000 0.01398 0.02954 =
0.00732 0.00320 -0.00014 0.00097
O3 4 0.470258 1.241559 0.282429 11.00000 0.01194 0.03053 =
0.01013 0.00243 0.00236 -0.00040
PART -1
AFIX 147
H3 2 0.484491 1.273555 0.256792 10.50000 -1.50000
AFIX 0
PART 0
O1 4 0.398734 0.784892 0.482115 11.00000 0.01869 0.02916 =
0.01047 0.00520 0.00130 -0.00308
O2 4 0.473445 1.043941 0.457870 11.00000 0.01320 0.02934 =
0.00851 0.00166 -0.00204 -0.00201
PART -1
AFIX 147
H2 2 0.488390 1.006191 0.487304 10.50000 -1.50000
AFIX 0
PART 0
O6 4 0.218103 0.726922 0.365807 11.00000 0.01588 0.02647 =
0.01333 0.00273 0.00192 -0.00455
N1 3 0.413645 0.425123 0.567430 11.00000 0.01916 0.01853 =
0.00931 0.00147 0.00238 -0.00106
AFIX 43
H1 2 0.417821 0.532713 0.539790 11.00000 -1.20000
AFIX 0
N2 3 0.377014 0.142624 0.622084 11.00000 0.01542 0.01710 =
0.01424 0.00242 0.00429 -0.00147
AFIX 43
H2B 2 0.352463 0.029800 0.636906 11.00000 -1.20000
AFIX 0
C2 1 0.416795 1.077574 0.360042 11.00000 0.01155 0.01376 =
0.01202 -0.00180 -0.00019 -0.00015
AFIX 43
H2A 2 0.456452 1.111505 0.365596 11.00000 -1.20000
AFIX 0
C1 1 0.390229 0.978561 0.399327 11.00000 0.01540 0.01340 =
0.00873 -0.00044 0.00014 0.00028
C9 1 0.240193 0.893134 0.335781 11.00000 0.01594 0.01527 =
0.00875 -0.00349 0.00062 0.00065
C4 1 0.328311 1.073485 0.304812 11.00000 0.01428 0.01329 =
0.00916 0.00028 -0.00044 0.00075
AFIX 43
H4 2 0.306933 1.108898 0.272846 11.00000 -1.20000
AFIX 0
C7 1 0.422785 0.928555 0.450869 11.00000 0.01473 0.01699 =
0.00953 -0.00015 0.00110 0.00230
C8 1 0.416653 1.230745 0.270974 11.00000 0.01138 0.01524 =
0.01083 -0.00044 0.00129 -0.00002
C6 1 0.332579 0.917216 0.390788 11.00000 0.01609 0.01385 =
0.00872 0.00034 0.00177 -0.00050
AFIX 43
H6 2 0.314219 0.841015 0.417075 11.00000 -1.20000
AFIX 0
C5 1 0.301616 0.967204 0.343746 11.00000 0.01448 0.01288 =
0.01076 -0.00151 0.00138 -0.00017
C3 1 0.386461 1.127974 0.312747 11.00000 0.01546 0.01183 =
0.01007 -0.00042 0.00125 0.00088
C12 1 0.366428 0.276044 0.576392 11.00000 0.01759 0.01520 =
0.01357 -0.00132 0.00094 0.00148
C10 1 0.454970 0.385454 0.607973 11.00000 0.01516 0.01718 =
0.01555 -0.00172 0.00023 -0.00035
AFIX 43
H10 2 0.492702 0.467759 0.611105 11.00000 -1.20000
AFIX 0
C11 1 0.432233 0.208673 0.642444 11.00000 0.01705 0.01813 =
0.01215 0.00000 -0.00024 0.00294
AFIX 43
H11 2 0.450624 0.142482 0.674491 11.00000 -1.20000
AFIX 0
C13 1 0.312388 0.260347 0.541677 11.00000 0.02008 0.02766 =
0.02126 0.00027 -0.00364 -0.00012
PART 1
AFIX 137
H13A 2 0.308320 0.473526 0.520952 21.00000 -1.50000
H13B 2 0.281126 0.247390 0.560431 21.00000 -1.50000
H13C 2 0.311958 0.049737 0.520678 21.00000 -1.50000
AFIX 0
PART 2
H13D 2 0.287129 0.449913 0.549385 -21.00000 -1.50000
H13E 2 0.317466 0.267138 0.507421 -21.00000 -1.50000
H13F 2 0.287275 0.072970 0.549461 -21.00000 -1.50000
HKLF 4
REM mim_btc_100k_c2_2_a.res in C2/c
REM wR2 = 0.1029, GooF = S = 1.036, Restrained GooF = 1.035 for all data
REM R1 = 0.0392 for 1969 Fo > 4sig(Fo) and 0.0566 for all 2531 data
REM 204 parameters refined using 3 restraints
END
WGHT 0.0457 3.1540
REM Highest difference peak 0.235, deepest hole -0.275, 1-sigma level 0.058
Q1 1 0.3605 0.9434 0.3005 11.00000 0.05 0.24
Q2 1 0.4012 1.1819 0.2985 11.00000 0.05 0.23
Q3 1 0.2810 0.9001 0.3396 11.00000 0.05 0.22
Q4 1 0.3979 0.8894 0.3817 11.00000 0.05 0.22
Q5 1 0.4031 0.9777 0.4188 11.00000 0.05 0.21
REM The information below was added by Olex2.
REM
REM R1 = 0.0392 for 1969 Fo > 4sig(Fo) and 0.0566 for all 26079 data
REM 204 parameters refined using n/a restraints
REM Highest difference peak 0.24, deepest hole -0.27
REM Mean Shift 0, Max Shift 0.000.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0566
REM R1_gt = 0.0392
REM wR_ref = 0.1029
REM GOOF = 1.036
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 26079
REM Reflections_gt = 1969
REM Parameters = 204
REM Hole = -0.27
REM Peak = 0.24
REM Flack = n/a
;
_cod_data_source_file jq2031sup1.cif
_cod_data_source_block I
_cod_depositor_comments 'Adding full bibliography for 2022933.cif.'
_cod_database_code 2022933
_cod_database_fobs_code 2022933
_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 0.987
_shelx_estimated_absorpt_t_max 0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O5 0.21243(5) 1.0194(4) 0.29386(4) 0.0167(3) Uani d 1 . .
H H5 0.178804 0.950516 0.290143 0.025 Uiso calc 1 . .
O O4 0.39014(5) 1.2973(4) 0.22895(4) 0.0172(3) Uani d 1 . .
O O3 0.47026(5) 1.2416(4) 0.28243(4) 0.0175(3) Uani d 1 . .
H H3 0.484491 1.273555 0.256792 0.026 Uiso calc 0.5 A -1
O O1 0.39873(5) 0.7849(4) 0.48212(4) 0.0196(3) Uani d 1 . .
O O2 0.47345(5) 1.0439(4) 0.45787(4) 0.0174(3) Uani d 1 . .
H H2 0.488390 1.006191 0.487304 0.026 Uiso calc 0.5 B -1
O O6 0.21810(5) 0.7269(4) 0.36581(4) 0.0186(3) Uani d 1 . .
N N1 0.41365(6) 0.4251(4) 0.56743(5) 0.0157(3) Uani d 1 . .
H H1 0.417821 0.532713 0.539790 0.019 Uiso calc 1 . .
N N2 0.37701(6) 0.1426(4) 0.62208(5) 0.0154(3) Uani d 1 . .
H H2B 0.352463 0.029800 0.636906 0.018 Uiso calc 1 . .
C C2 0.41679(7) 1.0776(5) 0.36004(6) 0.0127(4) Uani d 1 . .
H H2A 0.456452 1.111505 0.365596 0.015 Uiso calc 1 . .
C C1 0.39023(7) 0.9786(5) 0.39933(6) 0.0127(4) Uani d 1 . .
C C9 0.24019(7) 0.8931(5) 0.33578(6) 0.0135(4) Uani d 1 . .
C C4 0.32831(7) 1.0735(5) 0.30481(6) 0.0125(4) Uani d 1 . .
H H4 0.306933 1.108898 0.272846 0.015 Uiso calc 1 . .
C C7 0.42279(7) 0.9286(5) 0.45087(6) 0.0139(4) Uani d 1 . .
C C8 0.41665(7) 1.2307(5) 0.27097(6) 0.0125(4) Uani d 1 . .
C C6 0.33258(7) 0.9172(5) 0.39079(6) 0.0129(4) Uani d 1 . .
H H6 0.314219 0.841015 0.417075 0.016 Uiso calc 1 . .
C C5 0.30162(7) 0.9672(5) 0.34375(6) 0.0128(4) Uani d 1 . .
C C3 0.38646(7) 1.1280(5) 0.31275(6) 0.0126(4) Uani d 1 . .
C C12 0.36643(8) 0.2760(5) 0.57639(6) 0.0156(4) Uani d 1 . .
C C10 0.45497(8) 0.3855(5) 0.60797(6) 0.0162(4) Uani d 1 . .
H H10 0.492702 0.467759 0.611105 0.019 Uiso calc 1 . .
C C11 0.43223(7) 0.2087(5) 0.64244(7) 0.0161(4) Uani d 1 . .
H H11 0.450624 0.142482 0.674491 0.019 Uiso calc 1 . .
C C13 0.31239(8) 0.2603(6) 0.54168(8) 0.0238(4) Uani d 1 . .
H H13A 0.308320 0.473526 0.520952 0.036 Uiso calc 0.47(2) C 1
H H13B 0.281126 0.247390 0.560431 0.036 Uiso calc 0.47(2) C 1
H H13C 0.311958 0.049737 0.520678 0.036 Uiso calc 0.47(2) C 1
H H13D 0.2871(17) 0.450(11) 0.5494(18) 0.036 Uiso d 0.53(2) C 2
H H13E 0.3175(18) 0.267(16) 0.5074(8) 0.036 Uiso d 0.53(2) C 2
H H13F 0.2873(16) 0.073(11) 0.5495(18) 0.036 Uiso d 0.53(2) C 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O5 0.0115(6) 0.0275(7) 0.0096(6) -0.0027(5) -0.0024(5) 0.0013(5)
O4 0.0140(6) 0.0295(8) 0.0073(6) 0.0010(5) -0.0001(5) 0.0032(5)
O3 0.0119(6) 0.0305(8) 0.0101(6) -0.0004(5) 0.0024(5) 0.0024(6)
O1 0.0187(7) 0.0292(8) 0.0105(6) -0.0031(6) 0.0013(5) 0.0052(6)
O2 0.0132(6) 0.0293(8) 0.0085(6) -0.0020(5) -0.0020(5) 0.0017(6)
O6 0.0159(6) 0.0265(8) 0.0133(6) -0.0046(6) 0.0019(5) 0.0027(6)
N1 0.0192(8) 0.0185(8) 0.0093(7) -0.0011(6) 0.0024(6) 0.0015(6)
N2 0.0154(7) 0.0171(8) 0.0142(7) -0.0015(6) 0.0043(6) 0.0024(6)
C2 0.0115(8) 0.0138(9) 0.0120(8) -0.0002(7) -0.0002(7) -0.0018(7)
C1 0.0154(8) 0.0134(9) 0.0087(8) 0.0003(7) 0.0001(7) -0.0004(7)
C9 0.0159(9) 0.0153(9) 0.0088(8) 0.0006(7) 0.0006(7) -0.0035(7)
C4 0.0143(8) 0.0133(9) 0.0092(8) 0.0008(7) -0.0004(6) 0.0003(7)
C7 0.0147(8) 0.0170(9) 0.0095(8) 0.0023(7) 0.0011(7) -0.0001(7)
C8 0.0114(8) 0.0152(9) 0.0108(8) 0.0000(7) 0.0013(6) -0.0004(7)
C6 0.0161(9) 0.0139(9) 0.0087(8) -0.0005(7) 0.0018(7) 0.0003(7)
C5 0.0145(8) 0.0129(9) 0.0108(8) -0.0002(7) 0.0014(7) -0.0015(7)
C3 0.0155(9) 0.0118(9) 0.0101(8) 0.0009(7) 0.0013(7) -0.0004(7)
C12 0.0176(9) 0.0152(9) 0.0136(9) 0.0015(7) 0.0009(7) -0.0013(7)
C10 0.0152(9) 0.0172(9) 0.0156(9) -0.0003(7) 0.0002(7) -0.0017(7)
C11 0.0170(9) 0.0181(9) 0.0121(9) 0.0029(7) -0.0002(7) 0.0000(7)
C13 0.0201(10) 0.0277(11) 0.0213(10) -0.0001(8) -0.0036(8) 0.0003(9)
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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O5 H5 . . 109.5 ?
C8 O3 H3 . . 109.5 ?
C7 O2 H2 . . 109.5 ?
C12 N1 H1 . . 125.3 ?
C12 N1 C10 . . 109.41(15) ?
C10 N1 H1 . . 125.3 ?
C12 N2 H2B . . 125.2 ?
C12 N2 C11 . . 109.55(15) ?
C11 N2 H2B . . 125.2 ?
C1 C2 H2A . . 119.3 ?
C1 C2 C3 . . 121.37(16) ?
C3 C2 H2A . . 119.3 ?
C2 C1 C7 . . 121.63(15) ?
C6 C1 C2 . . 119.22(16) ?
C6 C1 C7 . . 119.14(15) ?
O5 C9 C5 . . 114.15(15) ?
O6 C9 O5 . . 123.87(16) ?
O6 C9 C5 . . 121.98(15) ?
C5 C4 H4 . . 120.0 ?
C5 C4 C3 . . 120.01(16) ?
C3 C4 H4 . . 120.0 ?
O1 C7 O2 . . 126.09(16) ?
O1 C7 C1 . . 118.28(15) ?
O2 C7 C1 . . 115.64(15) ?
O4 C8 O3 . . 124.26(15) ?
O4 C8 C3 . . 121.17(15) ?
O3 C8 C3 . . 114.57(15) ?
C1 C6 H6 . . 120.0 ?
C1 C6 C5 . . 120.09(16) ?
C5 C6 H6 . . 120.0 ?
C4 C5 C9 . . 121.01(15) ?
C6 C5 C9 . . 118.60(15) ?
C6 C5 C4 . . 120.36(16) ?
C2 C3 C4 . . 118.91(16) ?
C2 C3 C8 . . 119.96(15) ?
C4 C3 C8 . . 121.11(15) ?
N1 C12 N2 . . 107.26(15) ?
N1 C12 C13 . . 125.88(17) ?
N2 C12 C13 . . 126.86(17) ?
N1 C10 H10 . . 126.3 ?
C11 C10 N1 . . 107.41(16) ?
C11 C10 H10 . . 126.3 ?
N2 C11 H11 . . 126.8 ?
C10 C11 N2 . . 106.37(16) ?
C10 C11 H11 . . 126.8 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
C12 C13 H13D . . 110(3) ?
C12 C13 H13E . . 113(3) ?
C12 C13 H13F . . 113(3) ?
H13A C13 H13B . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
H13D C13 H13E . . 112(4) ?
H13D C13 H13F . . 93(4) ?
H13E C13 H13F . . 114(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 H5 0.8400
O5 C9 1.320(2)
O4 C8 1.247(2)
O3 H3 0.8400
O3 C8 1.277(2)
O1 C7 1.235(2)
O2 H2 0.8400
O2 C7 1.279(2)
O6 C9 1.224(2)
N1 H1 0.8800
N1 C12 1.326(2)
N1 C10 1.372(2)
N2 H2B 0.8800
N2 C12 1.335(2)
N2 C11 1.377(2)
C2 H2A 0.9500
C2 C1 1.391(2)
C2 C3 1.393(2)
C1 C7 1.511(2)
C1 C6 1.388(2)
C9 C5 1.485(2)
C4 H4 0.9500
C4 C5 1.393(2)
C4 C3 1.396(2)
C8 C3 1.505(2)
C6 H6 0.9500
C6 C5 1.392(2)
C12 C13 1.481(3)
C10 H10 0.9500
C10 C11 1.345(3)
C11 H11 0.9500
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C13 H13D 0.984(19)
C13 H13E 0.968(19)
C13 H13F 0.976(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O1 . 0.88 1.84 2.6771(19) 159
O2 H2 O2 5_676 0.84 1.64 2.4718(16) 171
N2 H2B O6 7_556 0.88 1.95 2.746(2) 151
O3 H3 O3 2_655 0.84 1.66 2.4601(16) 159
O5 H5 O4 4_545 0.84 1.75 2.5840(18) 170
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 C9 C5 C4 . . . . -16.1(2) ?
O5 C9 C5 C6 . . . . 165.92(15) ?
O4 C8 C3 C2 . . . . -175.82(17) ?
O4 C8 C3 C4 . . . . 5.7(3) ?
O3 C8 C3 C2 . . . . 4.4(2) ?
O3 C8 C3 C4 . . . . -174.11(16) ?
O6 C9 C5 C4 . . . . 163.43(17) ?
O6 C9 C5 C6 . . . . -14.5(3) ?
N1 C10 C11 N2 . . . . 0.1(2) ?
C2 C1 C7 O1 . . . . -168.16(17) ?
C2 C1 C7 O2 . . . . 12.3(3) ?
C2 C1 C6 C5 . . . . -2.3(3) ?
C1 C2 C3 C4 . . . . -0.7(3) ?
C1 C2 C3 C8 . . . . -179.26(16) ?
C1 C6 C5 C9 . . . . 178.97(16) ?
C1 C6 C5 C4 . . . . 1.0(3) ?
C7 C1 C6 C5 . . . . 178.97(16) ?
C6 C1 C7 O1 . . . . 10.5(3) ?
C6 C1 C7 O2 . . . . -169.07(16) ?
C5 C4 C3 C2 . . . . -0.6(3) ?
C5 C4 C3 C8 . . . . 177.89(16) ?
C3 C2 C1 C7 . . . . -179.11(16) ?
C3 C2 C1 C6 . . . . 2.2(3) ?
C3 C4 C5 C9 . . . . -177.44(16) ?
C3 C4 C5 C6 . . . . 0.5(3) ?
C12 N1 C10 C11 . . . . -0.2(2) ?
C12 N2 C11 C10 . . . . 0.0(2) ?
C10 N1 C12 N2 . . . . 0.1(2) ?
C10 N1 C12 C13 . . . . -179.50(18) ?
C11 N2 C12 N1 . . . . -0.1(2) ?
C11 N2 C12 C13 . . . . 179.56(18) ?