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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/72/7227206.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7227206
loop_
_publ_author_name
'Nanubolu, Jagadeesh Babu'
'Ravikumar, Krishnan'
_publ_section_title
;
 Designing a new cocrystal of olanzapine drug and observation of
 concomitant polymorphism in a ternary cocrystal system
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              355
_journal_paper_doi               10.1039/C6CE02227H
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C17 H20 N4 S, C6 H6 O2, C7 H8'
_chemical_formula_sum            'C30 H34 N4 O2 S'
_chemical_formula_weight         514.67
_chemical_name_common            'Olanzapine-hydroquinone-toluene form II'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-10-20 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                88.561(2)
_cell_angle_beta                 85.685(2)
_cell_angle_gamma                81.729(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3202(10)
_cell_length_b                   10.5724(12)
_cell_length_c                   14.7777(16)
_cell_measurement_reflns_used    3903
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.37
_cell_volume                     1436.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15380
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_min         1.947
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5772
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0611
_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/[σ²(Fo²)+(0.0723P)²+0.6075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4141
_reflns_number_total             5772
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce02227h2.cif
_cod_data_source_block           ba31m
_cod_depositor_comments
'Adding full bibliography for 7227206--7227207.cif.'
_cod_database_code               7227206
_shelx_shelxl_version_number     2014/7
_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   0.943
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.7626(2) 0.2728(2) 0.68008(16) 0.0444(6) Uani 1 1 d . .
C2 C 0.7852(3) 0.2073(3) 0.76124(18) 0.0584(7) Uani 1 1 d . .
H2 H 0.7220 0.2289 0.8120 0.070 Uiso 1 1 calc R U
C3 C 0.9002(3) 0.1104(3) 0.7679(2) 0.0657(8) Uani 1 1 d . .
H3 H 0.9146 0.0673 0.8229 0.079 Uiso 1 1 calc R U
C4 C 0.9938(3) 0.0777(3) 0.6926(2) 0.0612(7) Uani 1 1 d . .
H4 H 1.0730 0.0140 0.6968 0.073 Uiso 1 1 calc R U
C5 C 0.9691(3) 0.1401(2) 0.61130(18) 0.0501(6) Uani 1 1 d . .
H5 H 1.0305 0.1153 0.5604 0.060 Uiso 1 1 calc R U
C6 C 0.8552(2) 0.2391(2) 0.60290(15) 0.0415(5) Uani 1 1 d . .
C7 C 0.8034(2) 0.4111(2) 0.49741(15) 0.0386(5) Uani 1 1 d . .
C8 C 0.7707(2) 0.5108(2) 0.56658(14) 0.0385(5) Uani 1 1 d . .
C9 C 0.6877(2) 0.4906(2) 0.64457(15) 0.0423(5) Uani 1 1 d . .
C10 C 0.7497(3) 0.7120(2) 0.63130(17) 0.0494(6) Uani 1 1 d . .
C11 C 0.8068(2) 0.6379(2) 0.56105(16) 0.0432(5) Uani 1 1 d . .
H11 H 0.8647 0.6668 0.5131 0.052 Uiso 1 1 calc R U
C12 C 0.7612(4) 0.8493(3) 0.6479(2) 0.0716(8) Uani 1 1 d . .
H12A H 0.8268 0.8796 0.6019 0.107 Uiso 1 1 calc R U
H12B H 0.7972 0.8568 0.7064 0.107 Uiso 1 1 calc R U
H12C H 0.6670 0.8994 0.6460 0.107 Uiso 1 1 calc R U
C13 C 0.8520(3) 0.3603(2) 0.33582(15) 0.0498(6) Uani 1 1 d . .
H13A H 0.7674 0.3290 0.3152 0.060 Uiso 1 1 calc R U
H13B H 0.9169 0.2880 0.3578 0.060 Uiso 1 1 calc R U
C14 C 0.9284(3) 0.4256(3) 0.25805(17) 0.0547(7) Uani 1 1 d . .
H14A H 1.0173 0.4499 0.2780 0.066 Uiso 1 1 calc R U
H14B H 0.9548 0.3657 0.2089 0.066 Uiso 1 1 calc R U
C15 C 0.7137(3) 0.5633(3) 0.37612(16) 0.0518(6) Uani 1 1 d . .
H15A H 0.6851 0.6226 0.4254 0.062 Uiso 1 1 calc R U
H15B H 0.6265 0.5375 0.3548 0.062 Uiso 1 1 calc R U
C16 C 0.7936(3) 0.6274(3) 0.30011(17) 0.0580(7) Uani 1 1 d . .
H16A H 0.7313 0.7021 0.2790 0.070 Uiso 1 1 calc R U
H16B H 0.8789 0.6558 0.3223 0.070 Uiso 1 1 calc R U
C17 C 0.9218(3) 0.6026(3) 0.1520(2) 0.0771(9) Uani 1 1 d . .
H17A H 1.0057 0.6285 0.1762 0.116 Uiso 1 1 calc R U
H17B H 0.8618 0.6764 0.1295 0.116 Uiso 1 1 calc R U
H17C H 0.9523 0.5440 0.1034 0.116 Uiso 1 1 calc R U
N1 N 0.6452(2) 0.3739(2) 0.67352(14) 0.0477(5) Uani 1 1 d . .
H1N H 0.590(3) 0.382(2) 0.7210(18) 0.055(8) Uiso 1 1 d . .
N2 N 0.8321(2) 0.28935(18) 0.51479(12) 0.0417(5) Uani 1 1 d . .
N3 N 0.8077(2) 0.45100(19) 0.40870(12) 0.0436(5) Uani 1 1 d . .
N4 N 0.8385(2) 0.5397(2) 0.22408(13) 0.0497(5) Uani 1 1 d . .
S1 S 0.65037(7) 0.62721(7) 0.70902(4) 0.0544(2) Uani 1 1 d . .
C18 C 0.6193(3) 0.0518(2) 0.46095(17) 0.0497(6) Uani 1 1 d . .
C19 C 0.5890(3) -0.0650(2) 0.43361(18) 0.0541(6) Uani 1 1 d . .
H19 H 0.6491 -0.1093 0.3883 0.065 Uiso 1 1 calc R U
C20 C 0.5290(3) 0.1169(2) 0.52762(18) 0.0520(6) Uani 1 1 d . .
H20 H 0.5475 0.1959 0.5465 0.062 Uiso 1 1 calc R U
O1 O 0.7382(2) 0.0971(2) 0.41969(14) 0.0717(6) Uani 1 1 d . .
H1O H 0.761(4) 0.165(3) 0.449(2) 0.095(11) Uiso 1 1 d . .
C21 C 0.6060(3) 0.4662(3) -0.06633(18) 0.0693(9) Uani 1 1 d . .
H21 H 0.6796 0.4441 -0.1116 0.083 Uiso 1 1 calc R U
C22 C 0.5357(3) 0.5185(3) 0.08735(15) 0.0500(6) Uani 1 1 d . .
C23 C 0.6416(3) 0.4830(3) 0.02126(17) 0.0620(8) Uani 1 1 d . .
H23 H 0.7384 0.4699 0.0349 0.074 Uiso 1 1 calc R U
O2 O 0.5647(2) 0.5400(3) 0.17469(12) 0.0767(7) Uani 1 1 d . .
H2O H 0.660(4) 0.529(3) 0.182(2) 0.082(10) Uiso 1 1 d . .
C24 C 0.7276(12) -0.1611(9) -0.0495(5) 0.265(4) Uani 1 1 d . U
H24A H 0.6792 -0.2349 -0.0384 0.398 Uiso 1 1 calc R U
H24B H 0.8301 -0.1878 -0.0608 0.398 Uiso 1 1 calc R U
H24C H 0.6905 -0.1146 -0.1014 0.398 Uiso 1 1 calc R U
C25 C 0.7027(6) -0.0824(5) 0.0265(3) 0.188(2) Uani 1 1 d G U
C26 C 0.6041(5) -0.1180(4) 0.0943(4) 0.173(2) Uani 1 1 d G U
H26 H 0.5578 -0.1888 0.0867 0.208 Uiso 1 1 calc R U
C27 C 0.5748(5) -0.0476(6) 0.1734(3) 0.191(3) Uani 1 1 d G U
H27 H 0.5088 -0.0714 0.2188 0.229 Uiso 1 1 calc R U
C28 C 0.6441(6) 0.0583(5) 0.1847(3) 0.192(3) Uani 1 1 d G U
H28 H 0.6244 0.1054 0.2376 0.231 Uiso 1 1 calc R U
C29 C 0.7427(6) 0.0939(5) 0.1169(4) 0.214(3) Uani 1 1 d G U
H29 H 0.7890 0.1647 0.1244 0.257 Uiso 1 1 calc R U
C30 C 0.7720(5) 0.0235(6) 0.0378(3) 0.205(3) Uani 1 1 d G U
H30 H 0.8380 0.0473 -0.0076 0.246 Uiso 1 1 calc R U
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'
S S 0.1246 0.1234 '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
C2 C1 C6 119.9(2) . .
C2 C1 N1 120.9(2) . .
C6 C1 N1 119.1(2) . .
C3 C2 C1 120.9(3) . .
C2 C3 C4 119.6(3) . .
C5 C4 C3 119.5(3) . .
C4 C5 C6 122.0(2) . .
C5 C6 C1 117.9(2) . .
C5 C6 N2 117.4(2) . .
C1 C6 N2 124.4(2) . .
N2 C7 N3 118.3(2) . .
N2 C7 C8 124.8(2) . .
N3 C7 C8 116.9(2) . .
C9 C8 C11 111.8(2) . .
C9 C8 C7 120.4(2) . .
C11 C8 C7 127.6(2) . .
C8 C9 N1 125.7(2) . .
C8 C9 S1 111.30(18) . .
N1 C9 S1 122.87(17) . .
C11 C10 C12 129.3(3) . .
C11 C10 S1 110.79(19) . .
C12 C10 S1 119.9(2) . .
C10 C11 C8 114.1(2) . .
N3 C13 C14 109.3(2) . .
N4 C14 C13 112.7(2) . .
N3 C15 C16 109.7(2) . .
N4 C16 C15 111.1(2) . .
C9 N1 C1 114.08(19) . .
C7 N2 C6 123.01(19) . .
C7 N3 C13 120.8(2) . .
C7 N3 C15 123.05(19) . .
C13 N3 C15 110.72(18) . .
C14 N4 C16 108.57(18) . .
C14 N4 C17 110.0(2) . .
C16 N4 C17 110.2(2) . .
C9 S1 C10 91.95(12) . .
O1 C18 C20 123.2(2) . .
O1 C18 C19 117.8(2) . .
C20 C18 C19 119.0(2) . .
C20 C19 C18 121.1(2) 2_656 .
C18 C20 C19 120.0(2) . 2_656
C22 C21 C23 120.9(2) 2_665 .
C23 C22 C21 118.9(2) . 2_665
C23 C22 O2 122.8(2) . .
C21 C22 O2 118.4(2) 2_665 .
C22 C23 C21 120.2(2) . .
C26 C25 C30 120.0 . .
C26 C25 C24 115.7(6) . .
C30 C25 C24 124.3(6) . .
C27 C26 C25 120.0 . .
C26 C27 C28 120.0 . .
C29 C28 C27 120.0 . .
C30 C29 C28 120.0 . .
C29 C30 C25 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.385(4) .
C1 C6 1.399(3) .
C1 N1 1.422(3) .
C2 C3 1.379(4) .
C3 C4 1.381(4) .
C4 C5 1.374(4) .
C5 C6 1.390(3) .
C6 N2 1.414(3) .
C7 N2 1.299(3) .
C7 N3 1.366(3) .
C7 C8 1.471(3) .
C8 C9 1.368(3) .
C8 C11 1.431(3) .
C9 N1 1.397(3) .
C9 S1 1.729(2) .
C10 C11 1.346(3) .
C10 C12 1.498(4) .
C10 S1 1.734(3) .
C13 N3 1.456(3) .
C13 C14 1.511(3) .
C14 N4 1.467(3) .
C15 N3 1.464(3) .
C15 C16 1.502(4) .
C16 N4 1.472(3) .
C17 N4 1.472(3) .
C18 O1 1.366(3) .
C18 C20 1.377(3) .
C18 C19 1.382(3) .
C19 C20 1.379(3) 2_656
C20 C19 1.379(3) 2_656
C21 C22 1.365(4) 2_665
C21 C23 1.382(3) .
C22 C23 1.355(3) .
C22 C21 1.365(4) 2_665
C22 O2 1.369(3) .
C24 C25 1.400(8) .
C25 C26 1.3900 .
C25 C30 1.3900 .
C26 C27 1.3900 .
C27 C28 1.3900 .
C28 C29 1.3900 .
C29 C30 1.3900 .
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
O2 H2O N4 0.90(3) 1.84(3) 2.706(3) 163(3) .
O1 H1O N2 0.91(4) 1.88(4) 2.777(3) 172(3) .
N1 H1N O2 0.84(3) 2.13(3) 2.936(3) 162(2) 2_666
C15 H15B N1 0.97 2.63 3.446(3) 141.8 2_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203048
