#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:05:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179612 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/76/4507605.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_4507605
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), (C2 H3 N1), (H2 O)'
_chemical_formula_sum            'C19 H22 N5 O S'
_chemical_formula_weight         368.48
_chemical_name_common            'olanzapine acetonitrile 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                 125.321(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.381(2)
_cell_length_b                   12.3856(9)
_cell_length_c                   15.0565(14)
_cell_measurement_reflns_used    9032
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.91
_cell_volume                     3709.7(6)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            64953
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6933
_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             1560
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.852
_refine_diff_density_min         -1.066
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5672
_refine_ls_number_restraints     216
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0575
_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)+(0.1021P)²+6.8924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1951
_reflns_number_gt                4818
_reflns_number_total             5672
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg301826s_si_002.cif
_cod_data_source_block           olanzapine_acetonitrile_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        3709.8(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4507605
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.31187(8) 0.29217(13) 0.34819(12) 0.0204(3) Uani 1 1 d U . .
N2 N 0.33052(7) 0.37362(12) 0.18381(12) 0.0192(3) Uani 1 1 d U . .
N3 N 0.22555(7) 0.41767(12) 0.03252(12) 0.0191(3) Uani 1 1 d U . .
N4 N 0.14613(8) 0.55201(13) -0.15487(12) 0.0240(3) Uani 1 1 d U . .
S1 S 0.20616(2) 0.14812(4) 0.25539(4) 0.02589(15) Uani 1 1 d U . .
C1 C 0.42490(9) 0.21568(16) 0.44515(14) 0.0238(4) Uani 1 1 d U . .
H1 H 0.4208 0.1921 0.5011 0.029 Uiso 1 1 calc R . .
C2 C 0.48394(9) 0.19482(18) 0.45373(15) 0.0281(4) Uani 1 1 d U . .
H2 H 0.5198 0.1570 0.5150 0.034 Uiso 1 1 calc R . .
C3 C 0.48997(9) 0.22976(17) 0.37204(16) 0.0251(4) Uani 1 1 d U . .
H3 H 0.5297 0.2145 0.3764 0.030 Uiso 1 1 calc R . .
C4 C 0.43772(9) 0.28714(15) 0.28377(14) 0.0207(3) Uani 1 1 d U . .
H4 H 0.4430 0.3128 0.2297 0.025 Uiso 1 1 calc R . .
C5 C 0.16064(9) 0.45988(14) 0.00208(14) 0.0202(3) Uani 1 1 d U . .
H5A H 0.1675 0.5288 0.0406 0.024 Uiso 1 1 calc R . .
H5B H 0.1396 0.4079 0.0239 0.024 Uiso 1 1 calc R . .
C6 C 0.11443(9) 0.47818(15) -0.12045(15) 0.0246(4) Uani 1 1 d U . .
H6A H 0.1048 0.4083 -0.1587 0.030 Uiso 1 1 calc R . .
H6B H 0.0713 0.5093 -0.1402 0.030 Uiso 1 1 calc R . .
C7 C 0.25742(9) 0.48909(15) -0.00261(14) 0.0210(3) Uani 1 1 d U . .
H7A H 0.3000 0.4566 0.0163 0.025 Uiso 1 1 calc R . .
H7B H 0.2679 0.5594 0.0352 0.025 Uiso 1 1 calc R . .
C8 C 0.21029(10) 0.50595(15) -0.12467(15) 0.0245(4) Uani 1 1 d U . .
H8A H 0.2315 0.5552 -0.1484 0.029 Uiso 1 1 calc R . .
H8B H 0.2020 0.4360 -0.1623 0.029 Uiso 1 1 calc R . .
C9 C 0.37168(8) 0.27081(14) 0.35519(13) 0.0182(3) Uani 1 1 d U . .
C10 C 0.37738(8) 0.30816(13) 0.27239(13) 0.0172(3) Uani 1 1 d U . .
C11 C 0.25424(9) 0.25006(14) 0.25365(14) 0.0187(3) Uani 1 1 d U . .
C12 C 0.23153(8) 0.27654(13) 0.14920(13) 0.0177(3) Uani 1 1 d U . .
C13 C 0.26611(9) 0.35839(13) 0.12702(13) 0.0171(3) Uani 1 1 d U . .
C14 C 0.17415(9) 0.21341(14) 0.06985(15) 0.0218(3) Uani 1 1 d U . .
H14 H 0.1523 0.2212 -0.0063 0.026 Uiso 1 1 calc R . .
C15 C 0.15401(10) 0.14135(15) 0.11385(16) 0.0262(4) Uani 1 1 d U . .
C17 C 0.09699(12) 0.0624(2) 0.0574(2) 0.0416(6) Uani 1 1 d U . .
H17A H 0.0770 0.0627 -0.0208 0.062 Uiso 1 1 calc R . .
H17B H 0.0629 0.0829 0.0693 0.062 Uiso 1 1 calc R . .
H17C H 0.1138 -0.0101 0.0868 0.062 Uiso 1 1 calc R . .
C18 C 0.10188(12) 0.5716(2) -0.27230(16) 0.0376(5) Uani 1 1 d U . .
H18A H 0.0912 0.5029 -0.3112 0.056 Uiso 1 1 calc R . .
H18B H 0.1245 0.6193 -0.2935 0.056 Uiso 1 1 calc R . .
H18C H 0.0603 0.6058 -0.2907 0.056 Uiso 1 1 calc R . .
O1W O 0.18054(9) 0.74686(12) 0.95665(13) 0.0320(3) Uani 1 1 d D . .
N1S N 0.5000 0.7126(12) 0.2500 0.495(14) Uiso 0.65 2 d SPDU . 1
C1S C 0.4494(6) 0.6673(10) 0.214(2) 0.246(9) Uiso 0.65 1 d PDU A 1
C2S C 0.4096(5) 0.5699(8) 0.1937(9) 0.098(3) Uiso 0.65 1 d PDU A 1
N1SA N 0.5572(4) 0.597(3) 0.296(4) 0.279(18) Uiso 0.35 1 d PDU . 2
C1SA C 0.5000 0.6112(8) 0.2500 0.079(2) Uiso 0.35 2 d SPDU . 2
C2SA C 0.4311(3) 0.5752(10) 0.1992(10) 0.058(2) Uiso 0.35 1 d PDU . 2
H1N H 0.3143(14) 0.273(2) 0.406(2) 0.029(7) Uiso 1 1 d . . .
H1W H 0.1687(16) 0.6883(16) 0.921(2) 0.045(8) Uiso 1 1 d D . .
H2W H 0.2227(8) 0.750(5) 0.986(5) 0.039(16) Uiso 0.50 1 d PD . .
H3W H 0.150(2) 0.789(4) 0.908(3) 0.031(14) 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'
S S 0.1246 0.1234 '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'
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
C11 N1 C9 112.88(14) . .
C11 N1 H1N 111.4(19) . .
C9 N1 H1N 113.7(18) . .
C13 N2 C10 123.48(15) . .
C13 N3 C7 118.64(14) . .
C13 N3 C5 120.75(14) . .
C7 N3 C5 111.98(13) . .
C18 N4 C8 110.35(17) . .
C18 N4 C6 110.98(16) . .
C8 N4 C6 109.38(14) . .
C11 S1 C15 92.19(9) . .
C2 C1 C9 120.75(17) . .
C2 C1 H1 119.6 . .
C9 C1 H1 119.6 . .
C3 C2 C1 119.51(17) . .
C3 C2 H2 120.2 . .
C1 C2 H2 120.2 . .
C2 C3 C4 119.83(17) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C3 C4 C10 121.83(16) . .
C3 C4 H4 119.1 . .
C10 C4 H4 119.1 . .
N3 C5 C6 109.90(15) . .
N3 C5 H5A 109.7 . .
C6 C5 H5A 109.7 . .
N3 C5 H5B 109.7 . .
C6 C5 H5B 109.7 . .
H5A C5 H5B 108.2 . .
N4 C6 C5 110.35(14) . .
N4 C6 H6A 109.6 . .
C5 C6 H6A 109.6 . .
N4 C6 H6B 109.6 . .
C5 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
N3 C7 C8 109.42(15) . .
N3 C7 H7A 109.8 . .
C8 C7 H7A 109.8 . .
N3 C7 H7B 109.8 . .
C8 C7 H7B 109.8 . .
H7A C7 H7B 108.2 . .
N4 C8 C7 110.74(15) . .
N4 C8 H8A 109.5 . .
C7 C8 H8A 109.5 . .
N4 C8 H8B 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
C1 C9 C10 120.43(16) . .
C1 C9 N1 119.98(15) . .
C10 C9 N1 119.57(15) . .
C4 C10 N2 116.23(15) . .
C4 C10 C9 117.61(15) . .
N2 C10 C9 125.88(15) . .
C12 C11 N1 125.40(16) . .
C12 C11 S1 111.31(13) . .
N1 C11 S1 123.09(13) . .
C11 C12 C14 112.15(15) . .
C11 C12 C13 121.29(15) . .
C14 C12 C13 126.52(15) . .
N2 C13 N3 118.30(15) . .
N2 C13 C12 125.71(15) . .
N3 C13 C12 115.80(14) . .
C15 C14 C12 113.83(16) . .
C15 C14 H14 123.1 . .
C12 C14 H14 123.1 . .
C14 C15 C17 129.00(19) . .
C14 C15 S1 110.52(14) . .
C17 C15 S1 120.47(16) . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N4 C18 H18A 109.5 . .
N4 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N4 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
H1W O1W H2W 104(5) . .
H1W O1W H3W 100(4) . .
H2W O1W H3W 127(6) . .
C1S N1S C1S 122.4(19) . 2_655
N1S C1S C2S 152.8(14) . .
C2SA N1SA C1SA 140(7) 2_655 .
N1SA C1SA N1SA 162(3) 2_655 .
N1SA C1SA C2SA 9(2) 2_655 .
N1SA C1SA C2SA 152.9(15) . .
N1SA C1SA C2SA 152.9(15) 2_655 2_655
N1SA C1SA C2SA 9(2) . 2_655
C2SA C1SA C2SA 144.3(12) . 2_655
N1SA C2SA C1SA 31(5) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C11 1.400(2) .
N1 C9 1.425(2) .
N1 H1N 0.87(3) .
N2 C13 1.296(2) .
N2 C10 1.407(2) .
N3 C13 1.384(2) .
N3 C7 1.464(2) .
N3 C5 1.466(2) .
N4 C18 1.464(2) .
N4 C8 1.469(3) .
N4 C6 1.472(2) .
S1 C11 1.7333(18) .
S1 C15 1.741(2) .
C1 C2 1.393(3) .
C1 C9 1.397(2) .
C1 H1 0.9500 .
C2 C3 1.390(3) .
C2 H2 0.9500 .
C3 C4 1.392(2) .
C3 H3 0.9500 .
C4 C10 1.404(2) .
C4 H4 0.9500 .
C5 C6 1.524(2) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.516(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.410(2) .
C11 C12 1.371(2) .
C12 C14 1.436(2) .
C12 C13 1.475(2) .
C14 C15 1.361(3) .
C14 H14 0.9500 .
C15 C17 1.499(3) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
O1W H1W 0.848(10) .
O1W H2W 0.853(10) .
O1W H3W 0.852(10) .
N1S C1S 1.164(5) .
N1S C1S 1.164(5) 2_655
C1S C2S 1.467(5) .
N1SA C2SA 0.36(3) 2_655
N1SA C1SA 1.158(5) .
C1SA N1SA 1.158(5) 2_655
C1SA C2SA 1.456(5) .
C1SA C2SA 1.456(5) 2_655
C2SA N1SA 0.36(3) 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
C9 C1 C2 C3 0.3(3) . .
C1 C2 C3 C4 1.4(3) . .
C2 C3 C4 C10 -2.2(3) . .
C13 N3 C5 C6 -156.08(15) . .
C7 N3 C5 C6 56.62(19) . .
C18 N4 C6 C5 -179.17(17) . .
C8 N4 C6 C5 58.84(19) . .
N3 C5 C6 N4 -57.1(2) . .
C13 N3 C7 C8 155.01(15) . .
C5 N3 C7 C8 -56.93(19) . .
C18 N4 C8 C7 177.96(16) . .
C6 N4 C8 C7 -59.67(19) . .
N3 C7 C8 N4 58.25(19) . .
C2 C1 C9 C10 -1.2(3) . .
C2 C1 C9 N1 -179.51(18) . .
C11 N1 C9 C1 -122.85(18) . .
C11 N1 C9 C10 58.8(2) . .
C3 C4 C10 N2 175.53(17) . .
C3 C4 C10 C9 1.2(3) . .
C13 N2 C10 C4 142.60(17) . .
C13 N2 C10 C9 -43.7(3) . .
C1 C9 C10 C4 0.5(2) . .
N1 C9 C10 C4 178.75(15) . .
C1 C9 C10 N2 -173.22(17) . .
N1 C9 C10 N2 5.1(3) . .
C9 N1 C11 C12 -59.7(2) . .
C9 N1 C11 S1 114.78(15) . .
C15 S1 C11 C12 -0.59(14) . .
C15 S1 C11 N1 -175.78(15) . .
N1 C11 C12 C14 175.35(16) . .
S1 C11 C12 C14 0.28(19) . .
N1 C11 C12 C13 -2.5(3) . .
S1 C11 C12 C13 -177.57(12) . .
C10 N2 C13 N3 -170.79(15) . .
C10 N2 C13 C12 4.1(3) . .
C7 N3 C13 N2 4.1(2) . .
C5 N3 C13 N2 -141.13(17) . .
C7 N3 C13 C12 -171.35(15) . .
C5 N3 C13 C12 43.5(2) . .
C11 C12 C13 N2 36.6(3) . .
C14 C12 C13 N2 -140.89(18) . .
C11 C12 C13 N3 -148.34(16) . .
C14 C12 C13 N3 34.1(2) . .
C11 C12 C14 C15 0.3(2) . .
C13 C12 C14 C15 178.01(17) . .
C12 C14 C15 C17 -179.7(2) . .
C12 C14 C15 S1 -0.7(2) . .
C11 S1 C15 C14 0.75(16) . .
C11 S1 C15 C17 179.84(19) . .
C1S N1S C1S C2S 10(5) 2_655 .
C2SA N1SA C1SA N1SA 17(17) 2_655 2_655
C2SA N1SA C1SA C2SA 23(24) 2_655 .
N1SA C1SA C2SA N1SA -168(12) . 2_655
C2SA C1SA C2SA N1SA -162(18) 2_655 2_655
