#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/80/4508042.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_4508042
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 H21 N4 S, C7 H6 N O2, O'
_chemical_formula_sum            'C24 H27 N5 O3 S'
_chemical_formula_weight         465.57
_chemical_name_systematic
; 
 Olanzapinium p-aminobenzoate hemihydrate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.0660(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5118(10)
_cell_length_b                   9.6552(8)
_cell_length_c                   19.3403(16)
_cell_measurement_reflns_used    5843
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.64
_cell_volume                     2336.0(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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23586
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.076
_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     316
_refine_ls_number_reflns         4589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0605
_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)+(0.0742P)²+2.9678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                4120
_reflns_number_total             4589
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400692x_si_003.cif
_cod_data_source_block           Olanzapinium_p-aminobenzoate_hemihydrate
_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_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4508042
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C2 C -0.00596(19) 0.1751(2) 0.16037(12) 0.0155(5) Uani 1 1 d .
C3 C -0.09261(19) 0.2638(2) 0.17221(12) 0.0157(5) Uani 1 1 d .
C5 C -0.14546(19) 0.3079(2) 0.05670(12) 0.0162(5) Uani 1 1 d .
C6 C -0.07781(19) 0.2305(3) 0.01807(12) 0.0168(5) Uani 1 1 d .
C7 C 0.0334(2) 0.2050(2) 0.04118(12) 0.0170(5) Uani 1 1 d .
C8 C -0.1296(2) 0.1766(2) -0.04334(12) 0.0187(5) Uani 1 1 d .
H8 H -0.0942 0.1199 -0.0759 0.022 Uiso 1 1 calc R
C9 C -0.2338(2) 0.2141(3) -0.05037(12) 0.0194(5) Uani 1 1 d .
C10 C -0.3130(2) 0.1746(3) -0.10618(13) 0.0257(6) Uani 1 1 d .
H10A H -0.2823 0.1023 -0.1353 0.039 Uiso 1 1 calc R
H10B H -0.3301 0.2560 -0.1346 0.039 Uiso 1 1 calc R
H10C H -0.3784 0.1397 -0.0851 0.039 Uiso 1 1 calc R
C11 C 0.01977(19) 0.0776(2) 0.21139(12) 0.0166(5) Uani 1 1 d .
H11 H 0.0779 0.0162 0.2043 0.020 Uiso 1 1 calc R
C12 C -0.0370(2) 0.0678(3) 0.27214(12) 0.0196(5) Uani 1 1 d .
H12 H -0.0190 -0.0010 0.3055 0.024 Uiso 1 1 calc R
C13 C -0.1203(2) 0.1591(3) 0.28385(12) 0.0192(5) Uani 1 1 d .
H13 H -0.1582 0.1553 0.3259 0.023 Uiso 1 1 calc R
C14 C -0.14771(19) 0.2562(3) 0.23364(12) 0.0176(5) Uani 1 1 d .
H14 H -0.2051 0.3184 0.2415 0.021 Uiso 1 1 calc R
C15 C 0.1044(2) 0.2784(3) -0.07262(13) 0.0213(5) Uani 1 1 d .
H15A H 0.1479 0.3630 -0.0651 0.026 Uiso 1 1 calc R
H15B H 0.0299 0.3072 -0.0830 0.026 Uiso 1 1 calc R
C16 C 0.1476(2) 0.1972(3) -0.13308(13) 0.0230(6) Uani 1 1 d .
H16A H 0.1007 0.1167 -0.1428 0.028 Uiso 1 1 calc R
H16B H 0.1479 0.2567 -0.1748 0.028 Uiso 1 1 calc R
C17 C 0.2618(2) 0.0673(3) -0.05140(12) 0.0213(5) Uani 1 1 d .
H17A H 0.3366 0.0408 -0.0403 0.026 Uiso 1 1 calc R
H17B H 0.2194 -0.0187 -0.0572 0.026 Uiso 1 1 calc R
C18 C 0.21757(19) 0.1515(3) 0.00734(13) 0.0191(5) Uani 1 1 d .
H18A H 0.2186 0.0958 0.0503 0.023 Uiso 1 1 calc R
H18B H 0.2623 0.2349 0.0152 0.023 Uiso 1 1 calc R
C19 C 0.2999(2) 0.0625(3) -0.17455(14) 0.0299(6) Uani 1 1 d .
H19A H 0.3743 0.0370 -0.1642 0.045 Uiso 1 1 calc R
H19B H 0.2963 0.1156 -0.2177 0.045 Uiso 1 1 calc R
H19C H 0.2565 -0.0215 -0.1795 0.045 Uiso 1 1 calc R
C20 C 0.53351(19) 0.4497(3) 0.15110(12) 0.0179(5) Uani 1 1 d .
C21 C 0.4348(2) 0.4678(3) 0.11783(13) 0.0200(5) Uani 1 1 d .
H21 H 0.4251 0.5432 0.0868 0.024 Uiso 1 1 calc R
C22 C 0.3509(2) 0.3782(3) 0.12914(13) 0.0199(5) Uani 1 1 d .
H22 H 0.2839 0.3941 0.1066 0.024 Uiso 1 1 calc R
C23 C 0.3632(2) 0.2639(3) 0.17349(12) 0.0197(5) Uani 1 1 d .
C24 C 0.4636(2) 0.2440(3) 0.20553(14) 0.0228(5) Uani 1 1 d .
H24 H 0.4749 0.1661 0.2348 0.027 Uiso 1 1 calc R
C25 C 0.5456(2) 0.3358(3) 0.19513(13) 0.0218(5) Uani 1 1 d .
H25 H 0.6122 0.3215 0.2184 0.026 Uiso 1 1 calc R
C26 C 0.62203(19) 0.5516(3) 0.14206(12) 0.0188(5) Uani 1 1 d .
H3A H 0.315(3) 0.235(4) -0.1126(18) 0.046(10) Uiso 1 1 d .
H4A H -0.169(3) 0.418(4) 0.1358(16) 0.029(8) Uiso 1 1 d .
H5A H 0.226(3) 0.188(3) 0.1705(16) 0.020(8) Uiso 1 1 d .
H5B H 0.285(2) 0.122(3) 0.2215(17) 0.027(8) Uiso 1 1 d .
N1 N 0.06485(16) 0.1850(2) 0.10447(10) 0.0171(4) Uani 1 1 d .
N2 N 0.10774(17) 0.1928(2) -0.01014(10) 0.0192(5) Uani 1 1 d .
N3 N 0.25819(18) 0.1481(2) -0.11733(11) 0.0207(5) Uani 1 1 d .
N4 N -0.12224(17) 0.3653(2) 0.12147(10) 0.0176(4) Uani 1 1 d .
N5 N 0.2810(2) 0.1749(3) 0.18577(13) 0.0251(5) Uani 1 1 d .
O1 O 0.60407(15) 0.65392(19) 0.10205(10) 0.0265(4) Uani 1 1 d .
O2 O 0.70818(13) 0.53445(18) 0.17514(9) 0.0209(4) Uani 1 1 d .
O3 O 0.4902(3) 0.1911(5) 0.0063(2) 0.1032(13) Uani 1 1 d .
S1 S -0.27206(5) 0.31713(6) 0.01891(3) 0.01974(18) 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
C11 C2 C3 117.7(2)
C11 C2 N1 116.5(2)
C3 C2 N1 125.5(2)
C14 C3 C2 120.3(2)
C14 C3 N4 119.8(2)
C2 C3 N4 119.8(2)
C6 C5 N4 126.1(2)
C6 C5 S1 111.63(18)
N4 C5 S1 122.10(18)
C5 C6 C8 112.1(2)
C5 C6 C7 121.2(2)
C8 C6 C7 126.7(2)
N1 C7 N2 118.1(2)
N1 C7 C6 125.5(2)
N2 C7 C6 116.2(2)
C9 C8 C6 113.7(2)
C9 C8 H8 123.1
C6 C8 H8 123.1
C8 C9 C10 128.6(2)
C8 C9 S1 110.65(18)
C10 C9 S1 120.69(19)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C2 121.9(2)
C12 C11 H11 119.0
C2 C11 H11 119.0
C13 C12 C11 119.5(2)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C14 119.5(2)
C12 C13 H13 120.3
C14 C13 H13 120.3
C3 C14 C13 121.0(2)
C3 C14 H14 119.5
C13 C14 H14 119.5
N2 C15 C16 109.8(2)
N2 C15 H15A 109.7
C16 C15 H15A 109.7
N2 C15 H15B 109.7
C16 C15 H15B 109.7
H15A C15 H15B 108.2
N3 C16 C15 110.5(2)
N3 C16 H16A 109.5
C15 C16 H16A 109.5
N3 C16 H16B 109.5
C15 C16 H16B 109.5
H16A C16 H16B 108.1
N3 C17 C18 110.8(2)
N3 C17 H17A 109.5
C18 C17 H17A 109.5
N3 C17 H17B 109.5
C18 C17 H17B 109.5
H17A C17 H17B 108.1
N2 C18 C17 109.2(2)
N2 C18 H18A 109.9
C17 C18 H18A 109.9
N2 C18 H18B 109.9
C17 C18 H18B 109.9
H18A C18 H18B 108.3
N3 C19 H19A 109.5
N3 C19 H19B 109.5
H19A C19 H19B 109.5
N3 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C21 C20 C25 117.8(2)
C21 C20 C26 121.1(2)
C25 C20 C26 121.1(2)
C22 C21 C20 121.2(2)
C22 C21 H21 119.4
C20 C21 H21 119.4
C21 C22 C23 120.9(2)
C21 C22 H22 119.5
C23 C22 H22 119.5
N5 C23 C24 120.5(2)
N5 C23 C22 121.8(2)
C24 C23 C22 117.7(2)
C25 C24 C23 120.8(2)
C25 C24 H24 119.6
C23 C24 H24 119.6
C24 C25 C20 121.6(2)
C24 C25 H25 119.2
C20 C25 H25 119.2
O2 C26 O1 123.6(2)
O2 C26 C20 119.0(2)
O1 C26 C20 117.4(2)
C7 N1 C2 123.3(2)
C7 N2 C15 122.5(2)
C7 N2 C18 120.0(2)
C15 N2 C18 110.87(19)
C19 N3 C16 111.3(2)
C19 N3 C17 109.9(2)
C16 N3 C17 110.71(19)
C19 N3 H3A 104.6(18)
C16 N3 H3A 111.7(19)
C17 N3 H3A 108.5(18)
C5 N4 C3 113.04(19)
C5 N4 H4A 114(2)
C3 N4 H4A 112(2)
C23 N5 H5A 120(2)
C23 N5 H5B 118(2)
H5A N5 H5B 117(3)
C5 S1 C9 91.88(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 C11 1.397(3)
C2 C3 1.404(3)
C2 N1 1.414(3)
C3 C14 1.387(3)
C3 N4 1.430(3)
C5 C6 1.363(3)
C5 N4 1.395(3)
C5 S1 1.734(2)
C6 C8 1.440(3)
C6 C7 1.474(3)
C7 N1 1.293(3)
C7 N2 1.378(3)
C8 C9 1.357(4)
C8 H8 0.9500
C9 C10 1.501(3)
C9 S1 1.743(3)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.388(3)
C11 H11 0.9500
C12 C13 1.386(4)
C12 H12 0.9500
C13 C14 1.388(3)
C13 H13 0.9500
C14 H14 0.9500
C15 N2 1.464(3)
C15 C16 1.516(4)
C15 H15A 0.9900
C15 H15B 0.9900
C16 N3 1.488(3)
C16 H16A 0.9900
C16 H16B 0.9900
C17 N3 1.495(3)
C17 C18 1.511(3)
C17 H17A 0.9900
C17 H17B 0.9900
C18 N2 1.464(3)
C18 H18A 0.9900
C18 H18B 0.9900
C19 N3 1.483(3)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 C21 1.393(3)
C20 C25 1.397(4)
C20 C26 1.494(3)
C21 C22 1.381(4)
C21 H21 0.9500
C22 C23 1.404(4)
C22 H22 0.9500
C23 N5 1.365(3)
C23 C24 1.403(4)
C24 C25 1.374(4)
C24 H24 0.9500
C25 H25 0.9500
C26 O2 1.254(3)
C26 O1 1.273(3)
N3 H3A 1.11(4)
N4 H4A 0.83(3)
N5 H5A 0.75(3)
N5 H5B 0.86(3)
