#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/76/4507610.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_4507610
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, (C3 H8 O2), (H2 O)'
_chemical_formula_sum            'C18.5 H23 N4 O2.25 S'
_chemical_formula_weight         369.47
_chemical_name_common            'olanzapine 1,2 propanediol 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                 125.206(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.704(2)
_cell_length_b                   12.1883(10)
_cell_length_c                   15.1242(12)
_cell_measurement_reflns_used    7900
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.62
_cell_measurement_theta_min      2.91
_cell_volume                     3720.9(5)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0255
_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            26423
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.076
_refine_diff_density_max         1.263
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0758P)²+9.5441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                2911
_reflns_number_total             3649
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg301826s_si_002.cif
_cod_data_source_block           olanzapine_propanediol_hydrate
_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        3721.0(5)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C18.50 H23 N4 O2.25 S'
_cod_database_code               4507610
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 0.79027(3) -0.34544(5) 0.24352(5) 0.0259(2) Uani 1 1 d .
N1 N 0.68415(10) -0.20399(18) 0.15150(17) 0.0229(5) Uani 1 1 d .
N2 N 0.66600(10) -0.12136(16) 0.31525(16) 0.0201(4) Uani 1 1 d .
N3 N 0.76963(10) -0.07316(17) 0.46362(16) 0.0213(5) Uani 1 1 d .
N4 N 0.85060(10) 0.05573(17) 0.65497(16) 0.0231(5) Uani 1 1 d .
C1 C 0.76386(12) -0.21717(19) 0.34869(19) 0.0198(5) Uani 1 1 d .
C2 C 0.74176(12) -0.2441(2) 0.2455(2) 0.0208(5) Uani 1 1 d .
C3 C 0.62593(12) -0.2287(2) 0.14608(19) 0.0215(5) Uani 1 1 d .
C4 C 0.62041(12) -0.19147(19) 0.22875(19) 0.0199(5) Uani 1 1 d .
C5 C 0.72977(12) -0.1347(2) 0.37130(19) 0.0192(5) Uani 1 1 d .
C6 C 0.82099(12) -0.2801(2) 0.4274(2) 0.0223(5) Uani 1 1 d .
H6 H 0.8425 -0.2720 0.5031 0.027 Uiso 1 1 calc R
C7 C 0.84152(13) -0.3520(2) 0.3841(2) 0.0248(6) Uani 1 1 d .
C8 C 0.89828(14) -0.4318(2) 0.4406(2) 0.0349(7) Uani 1 1 d .
H8A H 0.9132 -0.4406 0.5159 0.052 Uiso 1 1 calc R
H8B H 0.9349 -0.4039 0.4390 0.052 Uiso 1 1 calc R
H8C H 0.8837 -0.5029 0.4038 0.052 Uiso 1 1 calc R
C9 C 0.57421(13) -0.2877(2) 0.0589(2) 0.0285(6) Uani 1 1 d .
H9 H 0.5781 -0.3118 0.0031 0.034 Uiso 1 1 calc R
C10 C 0.51724(13) -0.3116(2) 0.0524(2) 0.0310(6) Uani 1 1 d .
H10 H 0.4823 -0.3515 -0.0076 0.037 Uiso 1 1 calc R
C11 C 0.51158(12) -0.2772(2) 0.1338(2) 0.0273(6) Uani 1 1 d .
H11 H 0.4731 -0.2946 0.1308 0.033 Uiso 1 1 calc R
C12 C 0.56227(12) -0.2173(2) 0.2197(2) 0.0225(5) Uani 1 1 d .
H12 H 0.5574 -0.1928 0.2743 0.027 Uiso 1 1 calc R
C13 C 0.73987(12) -0.0016(2) 0.5020(2) 0.0236(5) Uani 1 1 d .
H13A H 0.6973 -0.0332 0.4823 0.028 Uiso 1 1 calc R
H13B H 0.7308 0.0713 0.4673 0.028 Uiso 1 1 calc R
C14 C 0.78688(13) 0.0104(2) 0.6241(2) 0.0235(5) Uani 1 1 d .
H14A H 0.7669 0.0594 0.6501 0.028 Uiso 1 1 calc R
H14B H 0.7941 -0.0623 0.6586 0.028 Uiso 1 1 calc R
C15 C 0.88044(13) -0.0178(2) 0.6175(2) 0.0248(6) Uani 1 1 d .
H15A H 0.8891 -0.0902 0.6530 0.030 Uiso 1 1 calc R
H15B H 0.9233 0.0130 0.6378 0.030 Uiso 1 1 calc R
C16 C 0.83440(12) -0.0317(2) 0.4954(2) 0.0223(5) Uani 1 1 d .
H16A H 0.8286 0.0397 0.4597 0.027 Uiso 1 1 calc R
H16B H 0.8542 -0.0839 0.4714 0.027 Uiso 1 1 calc R
C17 C 0.89490(15) 0.0710(3) 0.7726(2) 0.0350(7) Uani 1 1 d .
H17A H 0.9017 0.0004 0.8088 0.052 Uiso 1 1 calc R
H17B H 0.8749 0.1231 0.7954 0.052 Uiso 1 1 calc R
H17C H 0.9376 0.0996 0.7924 0.052 Uiso 1 1 calc R
O1W O 0.65920(15) 0.24575(19) 0.44573(19) 0.0539(7) Uani 1 1 d DU
O1S O 0.58992(13) 0.0605(2) 0.3159(3) 0.0772(10) Uani 1 1 d D
C1S C 0.52196(17) 0.0597(3) 0.2276(4) 0.0651(12) Uani 1 1 d D
C3S C 0.5130(5) 0.1704(7) 0.1844(8) 0.089(3) Uani 0.50 1 d PD
O2S O 0.5000 0.2488(10) 0.2500 0.136(5) Uani 0.50 2 d SPD
H1N H 0.6805(14) -0.223(2) 0.094(2) 0.026(8) Uiso 1 1 d .
H1W H 0.6428(14) 0.195(2) 0.399(2) 0.031 Uiso 1 1 d D
H2W H 0.6566(15) 0.3056(19) 0.413(2) 0.031 Uiso 1 1 d D
H1S H 0.612(3) 0.006(4) 0.311(6) 0.19(3) 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
C2 S1 C7 91.99(12) . .
C2 N1 C3 112.8(2) . .
C2 N1 H1N 113(2) . .
C3 N1 H1N 111.9(19) . .
N2 N2 C5 0(10) 1 .
N2 N2 C4 0(10) 1 .
C5 N2 C4 123.1(2) . .
C5 N3 C13 119.9(2) . .
C5 N3 C16 121.7(2) . .
C13 N3 C16 111.59(19) . .
C15 N4 C14 109.43(19) . .
C15 N4 C17 110.9(2) . .
C14 N4 C17 110.3(2) . .
C2 C1 C6 112.0(2) . .
C2 C1 C5 121.7(2) . .
C6 C1 C5 126.4(2) . .
C1 C2 N1 125.5(2) . .
C1 C2 S1 111.51(19) . .
N1 C2 S1 122.75(19) . .
C9 C3 C4 120.0(2) . .
C9 C3 N1 120.5(2) . .
C4 C3 N1 119.5(2) . .
C12 C4 C3 117.4(2) . .
C12 C4 N2 116.8(2) . 1
C3 C4 N2 125.5(2) . 1
C12 C4 N2 116.8(2) . .
C3 C4 N2 125.5(2) . .
N2 C4 N2 0.0(3) 1 .
N2 C5 N2 0.00(12) 1 .
N2 C5 N3 118.9(2) 1 .
N2 C5 N3 118.9(2) . .
N2 C5 C1 125.1(2) 1 .
N2 C5 C1 125.1(2) . .
N3 C5 C1 115.9(2) . .
C7 C6 C1 114.1(2) . .
C7 C6 H6 123.0 . .
C1 C6 H6 123.0 . .
C6 C7 C8 129.0(2) . .
C6 C7 S1 110.5(2) . .
C8 C7 S1 120.5(2) . .
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 . .
C10 C9 C3 121.0(2) . .
C10 C9 H9 119.5 . .
C3 C9 H9 119.5 . .
C11 C10 C9 119.6(2) . .
C11 C10 H10 120.2 . .
C9 C10 H10 120.2 . .
C10 C11 C12 119.7(2) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C11 C12 C4 122.3(2) . .
C11 C12 H12 118.9 . .
C4 C12 H12 118.9 . .
N3 C13 C14 109.5(2) . .
N3 C13 H13A 109.8 . .
C14 C13 H13A 109.8 . .
N3 C13 H13B 109.8 . .
C14 C13 H13B 109.8 . .
H13A C13 H13B 108.2 . .
N4 C14 C13 110.6(2) . .
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 . .
N4 C15 C16 110.3(2) . .
N4 C15 H15A 109.6 . .
C16 C15 H15A 109.6 . .
N4 C15 H15B 109.6 . .
C16 C15 H15B 109.6 . .
H15A C15 H15B 108.1 . .
N3 C16 C15 110.3(2) . .
N3 C16 H16A 109.6 . .
C15 C16 H16A 109.6 . .
N3 C16 H16B 109.6 . .
C15 C16 H16B 109.6 . .
H16A C16 H16B 108.1 . .
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 . .
H1W O1W H2W 107(3) . .
C1S O1S H1S 111(5) . .
O1S C1S C3S 101.9(5) . .
O1S C1S C1S 109.2(5) . 2_655
C3S C1S C1S 103.2(4) . 2_655
C1S C3S O2S 108.7(7) . .
C3S O2S C3S 103.1(9) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.733(3) .
S1 C7 1.740(3) .
N1 C2 1.397(3) .
N1 C3 1.425(3) .
N1 H1N 0.85(3) .
N2 N2 0.000(6) 1
N2 C5 1.299(3) .
N2 C4 1.418(3) .
N3 C5 1.377(3) .
N3 C13 1.459(3) .
N3 C16 1.470(3) .
N4 C15 1.465(3) .
N4 C14 1.467(3) .
N4 C17 1.468(3) .
C1 C2 1.364(3) .
C1 C6 1.435(3) .
C1 C5 1.473(3) .
C3 C9 1.395(4) .
C3 C4 1.409(3) .
C4 C12 1.398(3) .
C4 N2 1.418(3) 1
C5 N2 1.299(3) 1
C6 C7 1.355(4) .
C6 H6 0.9500 .
C7 C8 1.504(4) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.384(4) .
C9 H9 0.9500 .
C10 C11 1.382(4) .
C10 H10 0.9500 .
C11 C12 1.383(4) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C14 1.519(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.521(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
O1W H1W 0.848(18) .
O1W H2W 0.867(18) .
O1S C1S 1.420(4) .
O1S H1S 0.895(19) .
C1S C3S 1.459(8) .
C1S C1S 1.576(9) 2_655
C3S O2S 1.538(8) .
O2S C3S 1.538(8) 2_655
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 N1 174.4(2) . .
C5 C1 C2 N1 -4.0(4) . .
C6 C1 C2 S1 -0.2(3) . .
C5 C1 C2 S1 -178.57(18) . .
C3 N1 C2 C1 -59.3(3) . .
C3 N1 C2 S1 114.7(2) . .
C7 S1 C2 C1 -0.1(2) . .
C7 S1 C2 N1 -174.8(2) . .
C2 N1 C3 C9 -122.4(3) . .
C2 N1 C3 C4 58.7(3) . .
C9 C3 C4 C12 0.8(4) . .
N1 C3 C4 C12 179.7(2) . .
C9 C3 C4 N2 -173.0(2) . 1
N1 C3 C4 N2 6.0(4) . 1
C9 C3 C4 N2 -173.0(2) . .
N1 C3 C4 N2 6.0(4) . .
N2 N2 C4 C12 0.00(3) 1 .
C5 N2 C4 C12 141.0(2) . .
N2 N2 C4 C3 0.00(9) 1 .
C5 N2 C4 C3 -45.3(4) . .
C5 N2 C4 N2 0(88) . 1
C4 N2 C5 N2 0(100) . 1
N2 N2 C5 N3 0.00(10) 1 .
C4 N2 C5 N3 -170.3(2) . .
N2 N2 C5 C1 0.00(3) 1 .
C4 N2 C5 C1 5.1(4) . .
C13 N3 C5 N2 5.3(3) . 1
C16 N3 C5 N2 -143.5(2) . 1
C13 N3 C5 N2 5.3(3) . .
C16 N3 C5 N2 -143.5(2) . .
C13 N3 C5 C1 -170.5(2) . .
C16 N3 C5 C1 40.7(3) . .
C2 C1 C5 N2 37.4(4) . 1
C6 C1 C5 N2 -140.8(3) . 1
C2 C1 C5 N2 37.4(4) . .
C6 C1 C5 N2 -140.8(3) . .
C2 C1 C5 N3 -147.1(2) . .
C6 C1 C5 N3 34.7(3) . .
C2 C1 C6 C7 0.4(3) . .
C5 C1 C6 C7 178.7(2) . .
C1 C6 C7 C8 -179.0(3) . .
C1 C6 C7 S1 -0.5(3) . .
C2 S1 C7 C6 0.3(2) . .
C2 S1 C7 C8 179.0(2) . .
C4 C3 C9 C10 -0.7(4) . .
N1 C3 C9 C10 -179.6(2) . .
C3 C9 C10 C11 -0.4(4) . .
C9 C10 C11 C12 1.4(4) . .
C10 C11 C12 C4 -1.3(4) . .
C3 C4 C12 C11 0.2(4) . .
N2 C4 C12 C11 174.5(2) 1 .
N2 C4 C12 C11 174.5(2) . .
C5 N3 C13 C14 151.4(2) . .
C16 N3 C13 C14 -56.9(3) . .
C15 N4 C14 C13 -59.9(3) . .
C17 N4 C14 C13 177.9(2) . .
N3 C13 C14 N4 58.7(3) . .
C14 N4 C15 C16 58.8(3) . .
C17 N4 C15 C16 -179.3(2) . .
C5 N3 C16 C15 -152.4(2) . .
C13 N3 C16 C15 56.5(3) . .
N4 C15 C16 N3 -57.0(3) . .
O1S C1S C3S O2S -83.6(6) . .
C1S C1S C3S O2S 29.7(7) 2_655 .
C1S C3S O2S C3S -12.2(3) . 2_655
