#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/80/4508047.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_4508047
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_moiety         'C17 H20 N4 S, 0.5(C3 H6 O), H2 O'
_chemical_formula_sum            'C18.5 H25 N4 O1.5 S'
_chemical_formula_weight         359.48
_chemical_name_systematic
; 
 Olanzapine acetone monohydrate 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.803(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.628(3)
_cell_length_b                   12.5833(15)
_cell_length_c                   15.2002(18)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.68
_cell_volume                     3820.4(8)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19537
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.9395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3777
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0523
_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)+(0.0896P)²+2.0763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                3228
_reflns_number_total             3777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400692x_si_008.cif
_cod_data_source_block           Olanzapine_acetone_monohydrate
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        3820.5(8)
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_original_formula_sum        'C18.50 H25 N4 O1.50 S'
_cod_database_code               4508047
loop_
_symmetry_equiv_pos_as_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_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
S1 S 0.20813(3) 0.64911(5) 0.25266(5) 0.0593(2) Uani 1 1 d .
N2 N 0.22736(8) 0.91783(12) 0.03587(13) 0.0461(4) Uani 1 1 d .
C7 C 0.26758(9) 0.85804(14) 0.12854(15) 0.0421(4) Uani 1 1 d .
N1 N 0.33139(8) 0.87168(13) 0.18535(13) 0.0457(4) Uani 1 1 d .
C5 C 0.25551(9) 0.75054(15) 0.25227(16) 0.0456(4) Uani 1 1 d .
N3 N 0.14816(9) 1.05056(13) -0.14941(13) 0.0550(4) Uani 1 1 d .
C2 C 0.37778(9) 0.80665(15) 0.27306(14) 0.0441(4) Uani 1 1 d .
N4 N 0.31284(8) 0.79138(14) 0.34677(14) 0.0516(4) Uani 1 1 d .
C8 C 0.17657(9) 0.71439(15) 0.07009(16) 0.0487(5) Uani 1 1 d .
H8 H 0.1553 0.7225 -0.0041 0.058 Uiso 1 1 calc R
C14 C 0.43730(9) 0.78478(17) 0.28488(16) 0.0524(5) Uani 1 1 d .
H14 H 0.4425 0.8091 0.2324 0.063 Uiso 1 1 calc R
C6 C 0.23296(9) 0.77686(14) 0.14931(15) 0.0426(4) Uani 1 1 d .
C3 C 0.37207(9) 0.77005(15) 0.35450(15) 0.0459(4) Uani 1 1 d .
C18 C 0.25875(10) 0.98905(16) 0.00212(16) 0.0491(5) Uani 1 1 d .
H18A H 0.3004 0.9583 0.0209 0.059 Uiso 1 1 calc R
H18B H 0.2688 1.0566 0.0395 0.059 Uiso 1 1 calc R
O2 O 0.31990(13) 0.74417(15) 0.54112(17) 0.0831(6) Uani 1 1 d D
C9 C 0.15695(10) 0.64309(17) 0.11180(18) 0.0564(5) Uani 1 1 d .
C15 C 0.16262(9) 0.95866(16) 0.00471(16) 0.0490(5) Uani 1 1 d .
H15A H 0.1692 1.0247 0.0427 0.059 Uiso 1 1 calc R
H15B H 0.1421 0.9079 0.0250 0.059 Uiso 1 1 calc R
C11 C 0.42480(11) 0.71486(19) 0.44314(17) 0.0605(6) Uani 1 1 d .
H11 H 0.4210 0.6917 0.4974 0.073 Uiso 1 1 calc R
C17 C 0.21195(11) 1.00634(17) -0.11887(17) 0.0556(5) Uani 1 1 d .
H17A H 0.2325 1.0546 -0.1412 0.067 Uiso 1 1 calc R
H17B H 0.2041 0.9392 -0.1560 0.067 Uiso 1 1 calc R
C16 C 0.11729(10) 0.97742(17) -0.11591(17) 0.0570(5) Uani 1 1 d .
H16A H 0.1080 0.9103 -0.1536 0.068 Uiso 1 1 calc R
H16B H 0.0751 1.0068 -0.1356 0.068 Uiso 1 1 calc R
C13 C 0.48870(11) 0.7282(2) 0.37211(19) 0.0641(6) Uani 1 1 d .
H13 H 0.5274 0.7134 0.3769 0.077 Uiso 1 1 calc R
C12 C 0.48268(11) 0.6941(2) 0.45148(19) 0.0713(7) Uani 1 1 d .
H12 H 0.5175 0.6570 0.5110 0.086 Uiso 1 1 calc R
C19 C 0.10406(14) 1.0711(2) -0.26666(18) 0.0825(8) Uani 1 1 d .
H19A H 0.1255 1.1199 -0.2858 0.124 Uiso 1 1 calc R
H19B H 0.0627 1.1012 -0.2855 0.124 Uiso 1 1 calc R
H19C H 0.0952 1.0056 -0.3053 0.124 Uiso 1 1 calc R
C10 C 0.10123(13) 0.5628(2) 0.0544(2) 0.0835(8) Uani 1 1 d .
H10A H 0.0799 0.5669 -0.0223 0.125 Uiso 1 1 calc R
H10B H 0.0690 0.5776 0.0691 0.125 Uiso 1 1 calc R
H10C H 0.1192 0.4928 0.0798 0.125 Uiso 1 1 calc R
C21 C 0.5000 0.8599(8) 0.7500 0.147(3) Uani 1 2 d S
C20 C 0.4396(4) 0.9150(6) 0.7350(8) 0.254(4) Uani 1 1 d .
H20A H 0.4069 0.9307 0.6596 0.381 Uiso 1 1 calc R
H20B H 0.4538 0.9799 0.7760 0.381 Uiso 1 1 calc R
H20C H 0.4202 0.8690 0.7600 0.381 Uiso 1 1 calc R
O1 O 0.4726(7) 0.7772(11) 0.7009(14) 0.378(12) Uani 0.50 1 d P
H4 H 0.3176(12) 0.7698(18) 0.404(2) 0.059(6) Uiso 1 1 d .
H2B H 0.3403(15) 0.6824(19) 0.581(2) 0.102(10) Uiso 1 1 d D
H2A H 0.276(3) 0.765(9) 0.521(10) 0.35(5) Uiso 1 1 d 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
C5 S1 C9 91.86(10) . .
C7 N2 C18 118.88(15) . .
C7 N2 C15 121.16(15) . .
C18 N2 C15 111.79(15) . .
N1 C7 N2 118.58(16) . .
N1 C7 C6 125.40(16) . .
N2 C7 C6 115.86(15) . .
C7 N1 C2 123.73(16) . .
C6 C5 N4 125.50(18) . .
C6 C5 S1 111.16(15) . .
N4 C5 S1 123.08(14) . .
C16 N3 C17 109.33(16) . .
C16 N3 C19 111.54(18) . .
C17 N3 C19 110.27(19) . .
C14 C2 C3 117.48(17) . .
C14 C2 N1 116.55(17) . .
C3 C2 N1 125.71(17) . .
C5 N4 C3 112.80(16) . .
C9 C8 C6 114.27(18) . .
C13 C14 C2 122.0(2) . .
C5 C6 C8 112.16(17) . .
C5 C6 C7 121.04(17) . .
C8 C6 C7 126.73(16) . .
C11 C3 C2 119.98(18) . .
C11 C3 N4 120.42(18) . .
C2 C3 N4 119.58(17) . .
N2 C18 C17 109.46(16) . .
C8 C9 C10 129.3(2) . .
C8 C9 S1 110.55(16) . .
C10 C9 S1 120.12(18) . .
N2 C15 C16 109.88(17) . .
C12 C11 C3 120.8(2) . .
N3 C17 C18 110.75(17) . .
N3 C16 C15 110.88(16) . .
C12 C13 C14 119.8(2) . .
C13 C12 C11 119.9(2) . .
O1 C21 O1 64.0(18) 2_656 .
O1 C21 C20 98.8(8) 2_656 2_656
O1 C21 C20 127.9(9) . 2_656
O1 C21 C20 127.9(9) 2_656 .
O1 C21 C20 98.8(8) . .
C20 C21 C20 126.2(9) 2_656 .
C21 O1 O1 58.0(9) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C5 1.732(2) .
S1 C9 1.738(2) .
N2 C7 1.378(2) .
N2 C18 1.459(2) .
N2 C15 1.465(2) .
C7 N1 1.287(2) .
C7 C6 1.478(2) .
N1 C2 1.404(2) .
C5 C6 1.360(3) .
C5 N4 1.396(3) .
N3 C16 1.462(3) .
N3 C17 1.463(3) .
N3 C19 1.469(3) .
C2 C14 1.396(3) .
C2 C3 1.403(3) .
N4 C3 1.419(2) .
C8 C9 1.341(3) .
C8 C6 1.428(3) .
C14 C13 1.380(3) .
C3 C11 1.392(3) .
C18 C17 1.509(3) .
C9 C10 1.504(3) .
C15 C16 1.506(3) .
C11 C12 1.380(3) .
C13 C12 1.368(4) .
C21 O1 1.227(11) 2_656
C21 O1 1.227(11) .
C21 C20 1.533(7) 2_656
C21 C20 1.533(7) .
O1 O1 1.30(3) 2_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146564
