#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/80/4508043.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_4508043
loop_
_publ_author_name
'Thakuria, Ranjit'
'Nangia, Ashwini'
_publ_section_title
;
 Olanzapinium Salts, Isostructural Solvates, and Their Physicochemical
 Properties
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3672
_journal_paper_doi               10.1021/cg400692x
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C33 H35 N4 O3 S'
_chemical_formula_weight         567.71
_chemical_name_systematic
; 
 Olanzapinium salicylate benzene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.808(7)
_cell_angle_beta                 104.176(8)
_cell_angle_gamma                95.930(8)
_cell_formula_units_Z            2
_cell_length_a                   9.270(4)
_cell_length_b                   10.539(5)
_cell_length_c                   15.713(7)
_cell_measurement_reflns_used    1639
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.170
_cell_measurement_theta_min      1.50
_cell_volume                     1431.0(11)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0743
_diffrn_reflns_av_sigmaI/netI    0.0993
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14968
_diffrn_reflns_theta_full        26.17
_diffrn_reflns_theta_max         26.17
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             602
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0830
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0496P)²+1.4828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1745
_reflns_number_gt                3987
_reflns_number_total             5664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400692x_si_004.cif
_cod_data_source_block           Olanzapinium_salicylate_benzene
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4508043
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C2 C 0.9225(4) 0.3088(3) 0.0969(2) 0.0170(8) Uani 1 1 d .
C3 C 0.8691(4) 0.3113(3) 0.1729(2) 0.0186(8) Uani 1 1 d .
C5 C 0.7722(4) 0.0841(3) 0.1423(2) 0.0183(8) Uani 1 1 d .
C6 C 0.8092(4) 0.0281(3) 0.0651(2) 0.0153(8) Uani 1 1 d .
C7 C 0.8121(4) 0.0995(4) -0.0042(2) 0.0172(8) Uani 1 1 d .
C8 C 0.8387(4) -0.1028(3) 0.0635(2) 0.0195(8) Uani 1 1 d .
H8 H 0.8687 -0.1554 0.0155 0.023 Uiso 1 1 calc R
C9 C 0.8204(4) -0.1456(3) 0.1352(3) 0.0205(8) Uani 1 1 d .
C10 C 0.8406(5) -0.2759(4) 0.1553(3) 0.0254(9) Uani 1 1 d .
H10A H 0.7418 -0.3267 0.1482 0.038 Uiso 1 1 calc R
H10B H 0.9032 -0.2615 0.2178 0.038 Uiso 1 1 calc R
H10C H 0.8900 -0.3249 0.1132 0.038 Uiso 1 1 calc R
C11 C 1.0439(4) 0.4064(3) 0.1051(3) 0.0197(8) Uani 1 1 d .
H11 H 1.0817 0.4069 0.0541 0.024 Uiso 1 1 calc R
C12 C 1.1095(4) 0.5010(4) 0.1849(3) 0.0248(9) Uani 1 1 d .
H12 H 1.1938 0.5640 0.1892 0.030 Uiso 1 1 calc R
C13 C 1.0536(5) 0.5052(4) 0.2590(3) 0.0273(9) Uani 1 1 d .
H13 H 1.0973 0.5716 0.3140 0.033 Uiso 1 1 calc R
C14 C 0.9312(4) 0.4099(4) 0.2516(3) 0.0231(9) Uani 1 1 d .
H14 H 0.8903 0.4132 0.3017 0.028 Uiso 1 1 calc R
C15 C 0.6525(4) -0.0911(4) -0.1277(3) 0.0233(9) Uani 1 1 d .
H15A H 0.5535 -0.0652 -0.1506 0.028 Uiso 1 1 calc R
H15B H 0.6468 -0.1329 -0.0778 0.028 Uiso 1 1 calc R
C16 C 0.6877(4) -0.1882(3) -0.2033(2) 0.0217(9) Uani 1 1 d .
H16A H 0.7839 -0.2178 -0.1793 0.026 Uiso 1 1 calc R
H16B H 0.6069 -0.2666 -0.2268 0.026 Uiso 1 1 calc R
C17 C 0.8068(4) 0.0012(4) -0.2436(2) 0.0216(9) Uani 1 1 d .
H17A H 0.8003 0.0456 -0.2934 0.026 Uiso 1 1 calc R
H17B H 0.9112 -0.0166 -0.2247 0.026 Uiso 1 1 calc R
C18 C 0.7741(4) 0.0917(4) -0.1648(2) 0.0226(9) Uani 1 1 d .
H18A H 0.8530 0.1715 -0.1408 0.027 Uiso 1 1 calc R
H18B H 0.6757 0.1200 -0.1854 0.027 Uiso 1 1 calc R
C19 C 0.7446(5) -0.2174(4) -0.3502(3) 0.0277(10) Uani 1 1 d .
H19A H 0.8478 -0.2320 -0.3260 0.042 Uiso 1 1 calc R
H19B H 0.7402 -0.1781 -0.4015 0.042 Uiso 1 1 calc R
H19C H 0.6756 -0.3019 -0.3706 0.042 Uiso 1 1 calc R
C20 C 0.8083(4) 0.1869(4) 0.4565(2) 0.0215(9) Uani 1 1 d .
C21 C 0.8316(4) 0.1027(4) 0.5129(3) 0.0232(9) Uani 1 1 d .
C22 C 0.9702(5) 0.1189(4) 0.5769(3) 0.0293(10) Uani 1 1 d .
H22 H 0.9863 0.0606 0.6153 0.035 Uiso 1 1 calc R
C23 C 1.0846(5) 0.2198(4) 0.5847(3) 0.0332(11) Uani 1 1 d .
H23 H 1.1796 0.2296 0.6277 0.040 Uiso 1 1 calc R
C24 C 1.0611(5) 0.3058(4) 0.5303(3) 0.0363(11) Uani 1 1 d .
H24 H 1.1388 0.3762 0.5365 0.044 Uiso 1 1 calc R
C25 C 0.9253(5) 0.2891(4) 0.4672(3) 0.0295(10) Uani 1 1 d .
H25 H 0.9099 0.3485 0.4296 0.035 Uiso 1 1 calc R
C26 C 0.6642(4) 0.1706(4) 0.3836(2) 0.0191(8) Uani 1 1 d .
C27 C 0.5279(5) 0.6755(5) 0.2683(3) 0.0398(12) Uani 1 1 d .
H27 H 0.5434 0.6979 0.2155 0.048 Uiso 1 1 calc R
C28 C 0.5616(5) 0.5575(5) 0.2860(3) 0.0415(12) Uani 1 1 d .
H28 H 0.6006 0.4987 0.2455 0.050 Uiso 1 1 calc R
C29 C 0.5387(5) 0.5260(4) 0.3614(3) 0.0423(13) Uani 1 1 d .
H29 H 0.5650 0.4467 0.3752 0.051 Uiso 1 1 calc R
C30 C 0.4776(6) 0.6090(5) 0.4174(3) 0.0450(13) Uani 1 1 d .
H30 H 0.4563 0.5848 0.4684 0.054 Uiso 1 1 calc R
C31 C 0.4470(5) 0.7256(5) 0.4008(3) 0.0415(12) Uani 1 1 d .
H31 H 0.4075 0.7841 0.4411 0.050 Uiso 1 1 calc R
C32 C 0.4729(5) 0.7591(4) 0.3263(3) 0.0357(11) Uani 1 1 d .
H32 H 0.4523 0.8412 0.3151 0.043 Uiso 1 1 calc R
C33 C 0.6153(5) 0.4441(4) -0.0259(3) 0.0264(9) Uani 1 1 d .
H33 H 0.6951 0.4059 -0.0440 0.032 Uiso 1 1 calc R
C34 C 0.5389(4) 0.3870(4) 0.0247(3) 0.0255(9) Uani 1 1 d .
H34 H 0.5654 0.3095 0.0415 0.031 Uiso 1 1 calc R
C35 C 0.4234(5) 0.4435(4) 0.0507(3) 0.0279(9) Uani 1 1 d .
H35 H 0.3703 0.4049 0.0857 0.033 Uiso 1 1 calc R
H3 H 0.613(5) -0.102(4) -0.299(3) 0.036(13) Uiso 1 1 d .
H4 H 0.708(4) 0.231(3) 0.213(2) 0.016(10) Uiso 1 1 d .
H3A H 0.621(8) 0.018(6) 0.449(5) 0.12(2) Uiso 1 1 d .
N1 N 0.8568(3) 0.2242(3) 0.0095(2) 0.0186(7) Uani 1 1 d .
N2 N 0.7704(3) 0.0260(3) -0.09365(19) 0.0180(7) Uani 1 1 d .
N3 N 0.6997(4) -0.1271(3) -0.2782(2) 0.0201(7) Uani 1 1 d .
N4 N 0.7465(4) 0.2135(3) 0.1682(2) 0.0199(7) Uani 1 1 d .
O1 O 0.5571(3) 0.0814(3) 0.38113(18) 0.0249(6) Uani 1 1 d .
O2 O 0.6518(3) 0.2421(3) 0.33061(17) 0.0239(6) Uani 1 1 d .
O3 O 0.7221(3) 0.0034(3) 0.50937(19) 0.0293(7) Uani 1 1 d .
S1 S 0.76701(11) -0.02425(9) 0.21045(6) 0.0198(2) Uani 1 1 d .
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
C3 C2 C11 117.8(3) . .
C3 C2 N1 125.8(3) . .
C11 C2 N1 116.2(3) . .
C14 C3 C2 120.3(3) . .
C14 C3 N4 119.8(3) . .
C2 C3 N4 119.9(3) . .
C6 C5 N4 126.3(3) . .
C6 C5 S1 111.7(3) . .
N4 C5 S1 122.0(3) . .
C5 C6 C8 111.4(3) . .
C5 C6 C7 120.8(3) . .
C8 C6 C7 127.8(3) . .
N1 C7 N2 116.1(3) . .
N1 C7 C6 126.6(3) . .
N2 C7 C6 117.2(3) . .
C9 C8 C6 114.7(3) . .
C8 C9 C10 129.0(3) . .
C8 C9 S1 110.7(3) . .
C10 C9 S1 120.3(3) . .
C12 C11 C2 121.7(4) . .
C11 C12 C13 120.3(4) . .
C12 C13 C14 118.8(4) . .
C3 C14 C13 121.1(4) . .
N2 C15 C16 109.7(3) . .
N3 C16 C15 110.8(3) . .
N3 C17 C18 112.5(3) . .
N2 C18 C17 110.6(3) . .
C21 C20 C25 118.4(4) . .
C21 C20 C26 122.4(3) . .
C25 C20 C26 119.2(3) . .
O3 C21 C20 122.4(3) . .
O3 C21 C22 117.6(4) . .
C20 C21 C22 120.0(4) . .
C23 C22 C21 120.1(4) . .
C24 C23 C22 120.2(4) . .
C25 C24 C23 119.5(4) . .
C24 C25 C20 121.7(4) . .
O2 C26 O1 123.2(3) . .
O2 C26 C20 120.4(3) . .
O1 C26 C20 116.4(3) . .
C32 C27 C28 119.9(4) . .
C29 C28 C27 119.7(4) . .
C28 C29 C30 119.7(4) . .
C31 C30 C29 120.5(5) . .
C30 C31 C32 120.1(4) . .
C27 C32 C31 120.1(4) . .
C34 C33 C35 120.4(4) . 2_665
C33 C34 C35 119.3(4) . .
C33 C35 C34 120.3(4) 2_665 .
C7 N1 C2 122.8(3) . .
C7 N2 C18 119.4(3) . .
C7 N2 C15 122.6(3) . .
C18 N2 C15 110.2(3) . .
C19 N3 C16 111.7(3) . .
C19 N3 C17 110.5(3) . .
C16 N3 C17 111.3(3) . .
C5 N4 C3 113.8(3) . .
C5 S1 C9 91.53(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 C3 1.397(5) .
C2 C11 1.404(5) .
C2 N1 1.409(4) .
C3 C14 1.378(5) .
C3 N4 1.429(5) .
C5 C6 1.366(5) .
C5 N4 1.397(4) .
C5 S1 1.735(4) .
C6 C8 1.430(5) .
C6 C7 1.457(5) .
C7 N1 1.290(4) .
C7 N2 1.384(4) .
C8 C9 1.343(5) .
C9 C10 1.497(5) .
C9 S1 1.739(4) .
C11 C12 1.373(5) .
C12 C13 1.379(5) .
C13 C14 1.399(5) .
C15 N2 1.465(4) .
C15 C16 1.511(5) .
C16 N3 1.482(5) .
C17 N3 1.497(5) .
C17 C18 1.503(5) .
C18 N2 1.445(4) .
C19 N3 1.481(5) .
C20 C21 1.384(5) .
C20 C25 1.397(5) .
C20 C26 1.496(5) .
C21 O3 1.362(5) .
C21 C22 1.391(5) .
C22 C23 1.384(6) .
C23 C24 1.376(6) .
C24 C25 1.366(6) .
C26 O2 1.234(4) .
C26 O1 1.281(4) .
C27 C32 1.353(6) .
C27 C28 1.383(6) .
C28 C29 1.358(7) .
C29 C30 1.366(7) .
C30 C31 1.355(6) .
C31 C32 1.361(6) .
C33 C34 1.377(5) .
C33 C35 1.381(5) 2_665
C34 C35 1.381(6) .
C35 C33 1.381(5) 2_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146563
