#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009059.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_2009059
loop_
_publ_author_name
'Krishna, R.'
'Shanmuga Sundara Raj, S.'
'Velmurugan, D.'
'Fun, H.-K.'
'Manikandan, S.'
'Raghunathan, R.'
_publ_section_title
;
 2,4,5-Triphenylspiro[pyrazolidine-3,3'-(4'-flavanone)]
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9900120
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C35 H26 N2 O2'
_chemical_formula_weight         506.58
_chemical_name_systematic
;
 Spiro Pyrazolidine [5.3] 4'-Flavanone.
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.5244(2)
_cell_length_b                   19.1647(3)
_cell_length_c                   24.83550(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.64
_cell_volume                     5485.21(13)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PARST (Nardelli, 1995)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_sigmaI/netI    0.036
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27670
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.131
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0396P)^2^+1.7056P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.128
_reflns_number_gt                3409
_reflns_number_total             4838
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    qa0170.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2009059
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 1.05905(15) 0.11030(10) 0.34897(7) 0.0563(5) Uani d . 1 N
N2 1.14553(15) 0.14170(10) 0.38107(8) 0.0580(5) Uani d . 1 N
C3 1.18506(18) 0.09642(11) 0.41474(9) 0.0492(5) Uani d . 1 C
C4 1.12732(17) 0.02550(11) 0.41028(8) 0.0462(5) Uani d . 1 C
H4A 1.1056 0.0089 0.4462 0.055 Uiso calc R 1 H
C5 1.01628(17) 0.04560(11) 0.37821(8) 0.0461(5) Uani d . 1 C
C6 0.97412(18) -0.00968(12) 0.33863(8) 0.0538(6) Uani d . 1 C
H6A 1.0334 -0.0131 0.3104 0.065 Uiso calc R 1 H
O7 0.86686(13) 0.01167(9) 0.31201(6) 0.0666(5) Uani d . 1 O
C8 0.6680(2) 0.03382(15) 0.32278(11) 0.0760(8) Uani d . 1 C
H8A 0.6547 0.0143 0.2891 0.091 Uiso calc R 1 H
C9 0.5775(2) 0.06002(15) 0.35257(13) 0.0764(8) Uani d . 1 C
H9A 0.5028 0.0587 0.3384 0.092 Uiso calc R 1 H
C10 0.5951(2) 0.08826(13) 0.40300(12) 0.0662(7) Uani d . 1 C
H10A 0.5326 0.1051 0.4228 0.079 Uiso calc R 1 H
C11 0.70569(19) 0.09140(11) 0.42386(10) 0.0543(6) Uani d . 1 C
H11A 0.7178 0.1109 0.4577 0.065 Uiso calc R 1 H
C12 0.91814(18) 0.06805(11) 0.41657(9) 0.0470(5) Uani d . 1 C
C13 0.78002(19) 0.03690(12) 0.34382(9) 0.0548(6) Uani d . 1 C
C14 0.80007(17) 0.06545(11) 0.39445(8) 0.0461(5) Uani d . 1 C
C15 0.9788(2) 0.16006(14) 0.32622(10) 0.0605(6) Uani d . 1 C
C16 0.9423(2) 0.21722(14) 0.35504(12) 0.0734(8) Uani d . 1 C
H16A 0.9686 0.2243 0.3900 0.088 Uiso calc R 1 H
C17 0.8656(3) 0.26453(17) 0.33175(17) 0.0977(10) Uani d . 1 C
H17A 0.8418 0.3037 0.3509 0.117 Uiso calc R 1 H
C18 0.8254(3) 0.2534(2) 0.28068(19) 0.1175(14) Uani d . 1 C
H18A 0.7732 0.2847 0.2654 0.141 Uiso calc R 1 H
C19 0.8614(3) 0.1965(3) 0.25195(14) 0.1189(14) Uani d . 1 C
H19A 0.8330 0.1891 0.2174 0.143 Uiso calc R 1 H
C20 0.9399(3) 0.14987(18) 0.27396(11) 0.0900(9) Uani d . 1 C
H20A 0.9662 0.1121 0.2539 0.108 Uiso calc R 1 H
C21 1.27747(18) 0.11414(11) 0.45323(9) 0.0497(5) Uani d . 1 C
C22 1.3199(2) 0.06535(12) 0.48921(9) 0.0579(6) Uani d . 1 C
H22A 1.2928 0.0197 0.4877 0.069 Uiso calc R 1 H
C23 1.4020(2) 0.08338(14) 0.52743(10) 0.0699(7) Uani d . 1 C
H23A 1.4303 0.0497 0.5510 0.084 Uiso calc R 1 H
C24 1.4419(2) 0.15067(15) 0.53060(12) 0.0760(8) Uani d . 1 C
H24A 1.4963 0.1629 0.5566 0.091 Uiso calc R 1 H
C25 1.4013(2) 0.19986(15) 0.49511(12) 0.0768(8) Uani d . 1 C
H25A 1.4281 0.2455 0.4972 0.092 Uiso calc R 1 H
C26 1.3207(2) 0.18189(13) 0.45636(11) 0.0661(7) Uani d . 1 C
H26A 1.2950 0.2154 0.4321 0.079 Uiso calc R 1 H
C27 1.20642(17) -0.02761(11) 0.38322(8) 0.0453(5) Uani d . 1 C
C28 1.22200(19) -0.09356(12) 0.40513(9) 0.0554(6) Uani d . 1 C
H28A 1.1853 -0.1051 0.4373 0.066 Uiso calc R 1 H
C29 1.2913(2) -0.14221(13) 0.37981(11) 0.0662(7) Uani d . 1 C
H29A 1.3016 -0.1860 0.3953 0.079 Uiso calc R 1 H
C30 1.3456(2) -0.12661(14) 0.33178(11) 0.0710(7) Uani d . 1 C
H30A 1.3911 -0.1598 0.3145 0.085 Uiso calc R 1 H
C31 1.3314(2) -0.06147(14) 0.30997(10) 0.0694(7) Uani d . 1 C
H31A 1.3681 -0.0504 0.2777 0.083 Uiso calc R 1 H
C32 1.26342(19) -0.01221(12) 0.33531(9) 0.0569(6) Uani d . 1 C
H32A 1.2555 0.0319 0.3202 0.068 Uiso calc R 1 H
C33 0.95658(18) -0.08264(12) 0.36023(10) 0.0549(6) Uani d . 1 C
C34 0.9184(2) -0.09723(12) 0.41215(11) 0.0637(7) Uani d . 1 C
H34A 0.9062 -0.0607 0.4361 0.076 Uiso calc R 1 H
C35 0.8983(2) -0.16449(14) 0.42869(14) 0.0842(9) Uani d . 1 C
H35A 0.8726 -0.1733 0.4635 0.101 Uiso calc R 1 H
C36 0.9163(3) -0.21847(16) 0.3937(2) 0.1036(12) Uani d . 1 C
H36A 0.9021 -0.2640 0.4048 0.124 Uiso calc R 1 H
C37 0.9554(3) -0.20588(19) 0.34231(19) 0.1074(12) Uani d . 1 C
H37A 0.9680 -0.2429 0.3188 0.129 Uiso calc R 1 H
C38 0.9760(2) -0.13831(16) 0.32563(12) 0.0823(9) Uani d . 1 C
H38A 1.0031 -0.1300 0.2909 0.099 Uiso calc R 1 H
O39 0.93951(13) 0.08803(9) 0.46223(6) 0.0644(5) Uani d . 1 O
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
N1 0.0479(11) 0.0691(12) 0.0519(11) 0.0019(9) -0.0023(9) 0.0158(10)
N2 0.0451(11) 0.0661(12) 0.0629(13) -0.0013(9) -0.0024(10) 0.0114(10)
C3 0.0429(12) 0.0557(13) 0.0489(13) 0.0035(10) 0.0017(10) 0.0081(11)
C4 0.0412(11) 0.0596(13) 0.0378(11) 0.0003(10) -0.0002(9) 0.0084(10)
C5 0.0411(11) 0.0600(13) 0.0373(11) 0.0033(10) 0.0009(10) 0.0028(10)
C6 0.0411(12) 0.0825(16) 0.0378(12) 0.0104(11) -0.0007(10) -0.0076(12)
O7 0.0543(10) 0.1028(13) 0.0426(9) 0.0195(9) -0.0102(8) -0.0139(9)
C8 0.0555(16) 0.106(2) 0.0666(17) 0.0077(15) -0.0191(14) -0.0072(15)
C9 0.0448(14) 0.095(2) 0.090(2) 0.0065(13) -0.0111(15) 0.0068(17)
C10 0.0472(14) 0.0685(16) 0.0830(19) 0.0114(12) 0.0118(13) 0.0109(15)
C11 0.0520(14) 0.0536(13) 0.0573(14) 0.0051(11) 0.0093(11) 0.0031(11)
C12 0.0493(12) 0.0503(12) 0.0413(12) 0.0002(10) 0.0024(10) -0.0013(10)
C13 0.0459(13) 0.0665(14) 0.0519(14) 0.0058(11) -0.0024(11) -0.0007(12)
C14 0.0419(12) 0.0512(12) 0.0451(12) 0.0014(9) 0.0011(10) 0.0025(10)
C15 0.0473(13) 0.0776(17) 0.0566(15) 0.0083(12) 0.0042(11) 0.0228(13)
C16 0.0616(16) 0.0726(17) 0.086(2) 0.0047(14) -0.0030(15) 0.0206(16)
C17 0.074(2) 0.089(2) 0.130(3) 0.0198(16) 0.005(2) 0.034(2)
C18 0.077(2) 0.149(4) 0.126(3) 0.035(2) 0.002(2) 0.073(3)
C19 0.094(2) 0.190(4) 0.073(2) 0.038(3) -0.0076(19) 0.053(3)
C20 0.084(2) 0.133(3) 0.0533(16) 0.0259(18) 0.0010(15) 0.0271(17)
C21 0.0415(12) 0.0530(13) 0.0544(13) -0.0008(10) 0.0008(10) 0.0016(11)
C22 0.0581(14) 0.0572(14) 0.0582(14) -0.0041(11) -0.0089(12) 0.0035(12)
C23 0.0743(17) 0.0712(17) 0.0641(16) 0.0005(14) -0.0211(14) 0.0040(14)
C24 0.0674(17) 0.082(2) 0.0787(19) -0.0071(14) -0.0203(15) -0.0077(16)
C25 0.0704(17) 0.0611(16) 0.099(2) -0.0132(14) -0.0109(16) -0.0087(16)
C26 0.0589(15) 0.0576(15) 0.0819(18) -0.0005(12) -0.0077(14) 0.0090(13)
C27 0.0382(11) 0.0547(13) 0.0429(12) -0.0011(9) -0.0039(10) 0.0077(10)
C28 0.0461(13) 0.0630(15) 0.0571(14) -0.0028(11) -0.0025(11) 0.0164(12)
C29 0.0543(14) 0.0585(15) 0.0860(19) 0.0065(12) -0.0077(14) 0.0145(14)
C30 0.0585(15) 0.0759(18) 0.0786(19) 0.0184(13) 0.0024(14) -0.0029(15)
C31 0.0635(16) 0.0869(19) 0.0578(15) 0.0169(14) 0.0150(13) 0.0094(14)
C32 0.0530(13) 0.0638(14) 0.0538(14) 0.0075(11) 0.0076(12) 0.0161(12)
C33 0.0388(12) 0.0670(15) 0.0588(15) 0.0067(10) -0.0081(11) -0.0182(13)
C34 0.0599(15) 0.0544(15) 0.0769(18) 0.0007(11) 0.0133(13) -0.0131(13)
C35 0.0717(18) 0.0596(17) 0.121(3) 0.0019(14) 0.0163(17) -0.0006(18)
C36 0.084(2) 0.0581(19) 0.168(4) 0.0012(16) -0.014(2) -0.014(2)
C37 0.107(3) 0.079(2) 0.136(3) 0.023(2) -0.025(3) -0.051(2)
C38 0.0796(19) 0.089(2) 0.0779(19) 0.0243(16) -0.0179(15) -0.0352(17)
O39 0.0582(10) 0.0868(12) 0.0483(10) 0.0031(8) -0.0009(8) -0.0173(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
_geom_angle_publ_flag
N2 N1 C15 113.1(2) y
N2 N1 C5 107.9(2) y
C15 N1 C5 121.2(2) y
C3 N2 N1 109.2(2) y
N2 C3 C21 121.5(2) y
N2 C3 C4 113.6(2) y
C21 C3 C4 124.9(2) y
C3 C4 C27 111.62(17) ?
C3 C4 C5 100.15(16) ?
C27 C4 C5 115.59(17) ?
N1 C5 C6 111.2(2) y
N1 C5 C12 107.8(2) y
C6 C5 C12 111.0(2) y
N1 C5 C4 100.4(2) y
C6 C5 C4 114.84(17) ?
C12 C5 C4 110.88(16) ?
O7 C6 C33 107.86(18) ?
O7 C6 C5 111.53(17) ?
C33 C6 C5 117.17(18) ?
C13 O7 C6 117.27(16) ?
C9 C8 C13 119.0(2) ?
C8 C9 C10 121.4(2) ?
C11 C10 C9 119.7(2) ?
C10 C11 C14 120.4(2) ?
O39 C12 C14 123.0(2) y
O39 C12 C5 120.9(2) y
C14 C12 C5 116.08(18) ?
O7 C13 C14 122.79(19) ?
O7 C13 C8 116.6(2) ?
C14 C13 C8 120.6(2) ?
C13 C14 C11 118.8(2) ?
C13 C14 C12 120.37(19) ?
C11 C14 C12 120.82(19) ?
C16 C15 C20 120.0(2) ?
C16 C15 N1 121.3(2) ?
C20 C15 N1 118.7(2) ?
C15 C16 C17 119.8(3) ?
C18 C17 C16 120.0(3) ?
C17 C18 C19 120.4(3) ?
C18 C19 C20 120.5(3) ?
C19 C20 C15 119.3(3) ?
C22 C21 C26 117.9(2) ?
C22 C21 C3 121.3(2) ?
C26 C21 C3 120.7(2) ?
C21 C22 C23 121.1(2) ?
C24 C23 C22 120.2(2) ?
C23 C24 C25 119.6(3) ?
C24 C25 C26 120.4(2) ?
C25 C26 C21 120.8(2) ?
C28 C27 C32 117.9(2) ?
C28 C27 C4 120.87(19) ?
C32 C27 C4 121.23(19) ?
C29 C28 C27 120.8(2) ?
C28 C29 C30 120.7(2) ?
C31 C30 C29 119.0(2) ?
C30 C31 C32 120.7(2) ?
C31 C32 C27 120.9(2) ?
C38 C33 C34 118.1(2) ?
C38 C33 C6 118.0(2) ?
C34 C33 C6 123.9(2) ?
C35 C34 C33 121.3(2) ?
C36 C35 C34 119.7(3) ?
C35 C36 C37 120.5(3) ?
C36 C37 C38 120.0(3) ?
C37 C38 C33 120.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 1.411(3) y
N1 C15 1.443(3) y
N1 C5 1.519(3) y
N2 C3 1.288(3) y
C3 C21 1.471(3) ?
C3 C4 1.517(3) y
C4 C27 1.523(3) y
C4 C5 1.556(3) y
C5 C6 1.525(3) ?
C5 C12 1.540(3) ?
C6 O7 1.460(2) y
C6 C33 1.511(3) y
O7 C13 1.364(3) y
C8 C9 1.373(4) ?
C8 C13 1.394(3) ?
C9 C10 1.380(4) ?
C10 C11 1.377(3) ?
C11 C14 1.401(3) ?
C12 O39 1.222(2) y
C12 C14 1.468(3) ?
C13 C14 1.391(3) ?
C15 C16 1.375(4) ?
C15 C20 1.387(4) ?
C16 C17 1.392(4) ?
C17 C18 1.367(5) ?
C18 C19 1.368(5) ?
C19 C20 1.384(4) ?
C21 C22 1.383(3) ?
C21 C26 1.393(3) ?
C22 C23 1.384(3) ?
C23 C24 1.371(3) ?
C24 C25 1.373(4) ?
C25 C26 1.381(3) ?
C27 C28 1.388(3) ?
C27 C32 1.391(3) ?
C28 C29 1.379(3) ?
C29 C30 1.380(4) ?
C30 C31 1.371(4) ?
C31 C32 1.379(3) ?
C33 C38 1.388(3) ?
C33 C34 1.391(3) ?
C34 C35 1.372(3) ?
C35 C36 1.367(4) ?
C36 C37 1.375(5) ?
C37 C38 1.380(5) ?
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
_geom_hbond_publ_flag
C31 H31A O7 6_555 0.93 2.53 3.363(3) 149.8 yes