#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/76/4507612.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_4507612
loop_
_publ_author_name
'Bhardwaj, Rajni M.'
'Price, Louise S.'
'Price, Sarah L.'
'Reutzel-Edens, Susan M.'
'Miller, Gary J.'
'Oswald, Iain D. H.'
'Johnston, Blair F.'
'Florence, Alastair J.'
_publ_section_title
;
 Exploring the Experimental and Computed Crystal Energy Landscape of
 Olanzapine
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1602
_journal_paper_doi               10.1021/cg301826s
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C17 H20 N4 S1, 2.5(H2 O1)'
_chemical_formula_sum            'C17 H25 N4 O2.5 S'
_chemical_formula_weight         357.47
_chemical_name_common            'olanzapine higher hydrate'
_chemical_name_systematic
;
 ?
;
_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                 124.928(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.940(6)
_cell_length_b                   12.156(3)
_cell_length_c                   14.867(3)
_cell_measurement_reflns_used    3357
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.92
_cell_volume                     3695.4(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12338
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0695
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1183P)²+4.2820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.2102
_reflns_number_gt                2479
_reflns_number_total             3582
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg301826s_si_002.cif
_cod_data_source_block           olanzapine_higherhydrate
_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        3695.2(14)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C17 H25 N4 O2.50 S'
_cod_database_code               4507612
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 0.20526(5) 0.34907(7) 0.25655(7) 0.0354(3) Uani 1 1 d .
N2 N 0.31858(15) 0.1226(2) 0.1653(2) 0.0310(7) Uani 1 1 d .
N4 N 0.13463(14) -0.0626(2) -0.1636(2) 0.0353(7) Uani 1 1 d .
N3 N 0.21456(14) 0.0836(2) 0.0156(2) 0.0327(7) Uani 1 1 d .
C2 C 0.36409(17) 0.2231(3) 0.3423(3) 0.0307(7) Uani 1 1 d .
N1 N 0.30743(15) 0.2034(2) 0.3397(2) 0.0330(7) Uani 1 1 d .
C5 C 0.25721(17) 0.1404(2) 0.1129(3) 0.0293(7) Uani 1 1 d .
C4 C 0.22580(16) 0.2235(3) 0.1410(3) 0.0294(7) Uani 1 1 d .
C9 C 0.41762(18) 0.2769(3) 0.4317(3) 0.0358(8) Uani 1 1 d .
H9 H 0.4151 0.3023 0.4896 0.043 Uiso 1 1 calc R
C1 C 0.36716(17) 0.1853(3) 0.2554(3) 0.0303(7) Uani 1 1 d .
C6 C 0.16931(17) 0.2872(3) 0.0660(3) 0.0305(7) Uani 1 1 d .
H6 H 0.1463 0.2807 -0.0113 0.037 Uiso 1 1 calc R
C3 C 0.25061(17) 0.2476(3) 0.2472(3) 0.0303(7) Uani 1 1 d .
C7 C 0.15126(18) 0.3578(3) 0.1146(3) 0.0337(8) Uani 1 1 d .
C12 C 0.42531(18) 0.2022(3) 0.2654(3) 0.0357(8) Uani 1 1 d .
H12 H 0.4292 0.1750 0.2094 0.043 Uiso 1 1 calc R
C15 C 0.24243(18) 0.0138(3) -0.0277(3) 0.0352(8) Uani 1 1 d .
H15A H 0.2576 -0.0563 0.0137 0.042 Uiso 1 1 calc R
H15B H 0.2806 0.0509 -0.0184 0.042 Uiso 1 1 calc R
C13 C 0.15476(17) 0.0360(3) -0.0034(3) 0.0352(8) Uani 1 1 d .
H13A H 0.1353 0.0885 0.0212 0.042 Uiso 1 1 calc R
H13B H 0.1657 -0.0323 0.0400 0.042 Uiso 1 1 calc R
C11 C 0.47758(18) 0.2567(3) 0.3528(3) 0.0385(8) Uani 1 1 d .
H11 H 0.5161 0.2691 0.3554 0.046 Uiso 1 1 calc R
C14 C 0.10579(18) 0.0106(3) -0.1238(3) 0.0386(8) Uani 1 1 d .
H14A H 0.0667 -0.0248 -0.1346 0.046 Uiso 1 1 calc R
H14B H 0.0917 0.0799 -0.1665 0.046 Uiso 1 1 calc R
C10 C 0.47376(18) 0.2937(3) 0.4374(3) 0.0404(9) Uani 1 1 d .
H10 H 0.5099 0.3303 0.4989 0.049 Uiso 1 1 calc R
C16 C 0.19148(19) -0.0096(3) -0.1484(3) 0.0392(9) Uani 1 1 d .
H16A H 0.1781 0.0602 -0.1902 0.047 Uiso 1 1 calc R
H16B H 0.2105 -0.0579 -0.1769 0.047 Uiso 1 1 calc R
C8 C 0.09610(19) 0.4383(3) 0.0631(3) 0.0432(9) Uani 1 1 d .
H8A H 0.1136 0.5130 0.0856 0.065 Uiso 1 1 calc R
H8B H 0.0675 0.4223 0.0868 0.065 Uiso 1 1 calc R
H8C H 0.0711 0.4323 -0.0169 0.065 Uiso 1 1 calc R
C17 C 0.0871(2) -0.0924(4) -0.2795(3) 0.0525(11) Uani 1 1 d .
H17A H 0.0715 -0.0256 -0.3244 0.079 Uiso 1 1 calc R
H17B H 0.0501 -0.1310 -0.2878 0.079 Uiso 1 1 calc R
H17C H 0.1082 -0.1405 -0.3035 0.079 Uiso 1 1 calc R
O1W O 0.18462(13) -0.25294(19) -0.03719(19) 0.0354(6) Uani 1 1 d D
O2W O 0.10961(16) 0.4326(3) 0.3417(3) 0.0642(9) Uani 1 1 d D
O3W O -0.0025(3) 0.3710(7) 0.1690(6) 0.087(2) Uani 0.50 1 d PD
H1N H 0.3108(15) 0.222(3) 0.396(3) 0.017(8) Uiso 1 1 d .
H1W1 H 0.1698(14) -0.1964(15) -0.078(2) 0.020 Uiso 1 1 d D
H2W1 H 0.1594(12) -0.3023(17) -0.0804(19) 0.020 Uiso 1 1 d D
H1W2 H 0.0681(5) 0.436(2) 0.299(2) 0.020 Uiso 1 1 d D
H2W2 H 0.1279(12) 0.4919(15) 0.344(2) 0.020 Uiso 1 1 d D
H1W3 H 0.0276(16) 0.410(4) 0.222(3) 0.020 Uiso 0.50 1 d PD
H2W3 H -0.0369(14) 0.396(5) 0.161(4) 0.020 Uiso 0.50 1 d PD
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
C3 S1 C7 91.94(16)
C5 N2 C1 124.5(3)
C16 N4 C14 109.2(3)
C16 N4 C17 110.5(3)
C14 N4 C17 111.7(3)
C5 N3 C15 118.2(3)
C5 N3 C13 118.9(3)
C15 N3 C13 111.9(3)
C9 C2 N1 120.2(3)
C9 C2 C1 120.0(3)
N1 C2 C1 119.8(3)
C3 N1 C2 113.4(3)
C3 N1 H1N 110(2)
C2 N1 H1N 114(2)
N2 C5 N3 119.0(3)
N2 C5 C4 126.0(3)
N3 C5 C4 114.8(3)
C3 C4 C6 112.4(3)
C3 C4 C5 120.9(3)
C6 C4 C5 126.7(3)
C10 C9 C2 121.1(3)
C10 C9 H9 119.5
C2 C9 H9 119.5
C12 C1 N2 117.3(3)
C12 C1 C2 117.1(3)
N2 C1 C2 125.3(3)
C7 C6 C4 114.2(3)
C7 C6 H6 122.9
C4 C6 H6 122.9
C4 C3 N1 126.2(3)
C4 C3 S1 111.3(3)
N1 C3 S1 122.4(2)
C6 C7 C8 129.2(3)
C6 C7 S1 110.2(3)
C8 C7 S1 120.5(3)
C11 C12 C1 122.7(3)
C11 C12 H12 118.6
C1 C12 H12 118.6
N3 C15 C16 110.0(3)
N3 C15 H15A 109.7
C16 C15 H15A 109.7
N3 C15 H15B 109.7
C16 C15 H15B 109.7
H15A C15 H15B 108.2
N3 C13 C14 110.6(3)
N3 C13 H13A 109.5
C14 C13 H13A 109.5
N3 C13 H13B 109.5
C14 C13 H13B 109.5
H13A C13 H13B 108.1
C12 C11 C10 119.5(4)
C12 C11 H11 120.3
C10 C11 H11 120.3
N4 C14 C13 110.6(3)
N4 C14 H14A 109.5
C13 C14 H14A 109.5
N4 C14 H14B 109.5
C13 C14 H14B 109.5
H14A C14 H14B 108.1
C9 C10 C11 119.6(3)
C9 C10 H10 120.2
C11 C10 H10 120.2
N4 C16 C15 110.4(3)
N4 C16 H16A 109.6
C15 C16 H16A 109.6
N4 C16 H16B 109.6
C15 C16 H16B 109.6
H16A C16 H16B 108.1
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N4 C17 H17A 109.5
N4 C17 H17B 109.5
H17A C17 H17B 109.5
N4 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
H1W1 O1W H2W1 102(2)
H1W2 O2W H2W2 113(3)
H1W3 O3W H2W3 102(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C3 1.731(3)
S1 C7 1.739(3)
N2 C5 1.277(4)
N2 C1 1.409(4)
N4 C16 1.453(5)
N4 C14 1.465(4)
N4 C17 1.472(4)
N3 C5 1.393(4)
N3 C15 1.459(4)
N3 C13 1.468(4)
C2 C9 1.394(5)
C2 N1 1.411(4)
C2 C1 1.414(4)
N1 C3 1.398(5)
N1 H1N 0.82(3)
C5 C4 1.478(4)
C4 C3 1.358(5)
C4 C6 1.425(5)
C9 C10 1.368(5)
C9 H9 0.9500
C1 C12 1.386(5)
C6 C7 1.353(5)
C6 H6 0.9500
C7 C8 1.493(5)
C12 C11 1.374(5)
C12 H12 0.9500
C15 C16 1.518(5)
C15 H15A 0.9900
C15 H15B 0.9900
C13 C14 1.512(5)
C13 H13A 0.9900
C13 H13B 0.9900
C11 C10 1.390(5)
C11 H11 0.9500
C14 H14A 0.9900
C14 H14B 0.9900
C10 H10 0.9500
C16 H16A 0.9900
C16 H16B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
O1W H1W1 0.849(10)
O1W H2W1 0.840(10)
O2W H1W2 0.851(10)
O2W H2W2 0.844(10)
O3W H1W3 0.858(10)
O3W H2W3 0.853(10)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 C2 N1 C3 123.3(3)
C1 C2 N1 C3 -58.5(4)
C1 N2 C5 N3 170.4(3)
C1 N2 C5 C4 -4.6(5)
C15 N3 C5 N2 -5.7(4)
C13 N3 C5 N2 135.6(3)
C15 N3 C5 C4 169.9(3)
C13 N3 C5 C4 -48.9(4)
N2 C5 C4 C3 -35.6(5)
N3 C5 C4 C3 149.1(3)
N2 C5 C4 C6 143.5(3)
N3 C5 C4 C6 -31.7(4)
N1 C2 C9 C10 177.9(3)
C1 C2 C9 C10 -0.3(5)
C5 N2 C1 C12 -144.4(3)
C5 N2 C1 C2 42.3(5)
C9 C2 C1 C12 1.4(5)
N1 C2 C1 C12 -176.8(3)
C9 C2 C1 N2 174.7(3)
N1 C2 C1 N2 -3.5(5)
C3 C4 C6 C7 -0.5(4)
C5 C4 C6 C7 -179.7(3)
C6 C4 C3 N1 -176.6(3)
C5 C4 C3 N1 2.6(5)
C6 C4 C3 S1 -0.3(4)
C5 C4 C3 S1 179.0(2)
C2 N1 C3 C4 58.8(4)
C2 N1 C3 S1 -117.1(3)
C7 S1 C3 C4 0.7(3)
C7 S1 C3 N1 177.2(3)
C4 C6 C7 C8 178.6(3)
C4 C6 C7 S1 1.0(4)
C3 S1 C7 C6 -1.0(3)
C3 S1 C7 C8 -178.8(3)
N2 C1 C12 C11 -176.3(3)
C2 C1 C12 C11 -2.4(5)
C5 N3 C15 C16 -161.2(3)
C13 N3 C15 C16 55.0(4)
C5 N3 C13 C14 162.1(3)
C15 N3 C13 C14 -54.4(4)
C1 C12 C11 C10 2.3(5)
C16 N4 C14 C13 -59.8(4)
C17 N4 C14 C13 177.7(3)
N3 C13 C14 N4 56.4(4)
C2 C9 C10 C11 0.1(5)
C12 C11 C10 C9 -1.1(5)
C14 N4 C16 C15 60.7(4)
C17 N4 C16 C15 -176.0(3)
N3 C15 C16 N4 -58.4(4)
