# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_olanzapinepropanol
_database_code_depnum_ccdc_archive 'CCDC 1479180'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-Methyl-4-(4-methylpiperazin-1-yl)-10H-\
thieno[2,3-b][1,5]benzodiazepine propan-1-ol solvate 
;
_chemical_name_common            'Olanzapine propan-1-ol'
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 N4 S, C3 H8 O'
_chemical_formula_sum            'C20 H28 N4 O S'
_chemical_formula_weight         372.52
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c


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'

_cell_length_a                   10.217(3)
_cell_length_b                   13.069(4)
_cell_length_c                   14.918(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.342(7)
_cell_angle_gamma                90.00
_cell_volume                     1983.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4767
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      28.33

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          .305
_exptl_crystal_size_mid          .225
_exptl_crystal_size_min          .102
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.5810
_exptl_absorpt_correction_T_max  0.7454


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13958
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_av_sigmaI/netI    0.1020
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         28.33
_reflns_number_total             4954
_reflns_number_gt                3028
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0705P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4767
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.928
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
S1 S 0.52031(6) 0.88551(4) 0.22096(3) 0.01822(15) Uani 1 1 d . . .
N1' N 0.56080(17) 1.16361(14) 0.44661(12) 0.0174(4) Uani 1 1 d . . .
N4' N 0.75127(18) 1.27557(14) 0.55935(12) 0.0193(4) Uani 1 1 d . . .
C2 C 0.6387(2) 0.88029(17) 0.31251(14) 0.0182(5) Uani 1 1 d . . .
N10 N 0.33167(18) 1.03386(15) 0.22148(12) 0.0186(4) Uani 1 1 d . . .
N5 N 0.34470(18) 1.13965(14) 0.39673(11) 0.0175(4) Uani 1 1 d . . .
C4 C 0.4644(2) 1.11041(17) 0.39433(13) 0.0161(5) Uani 1 1 d . . .
C2' C 0.6912(2) 1.18337(17) 0.41873(14) 0.0183(5) Uani 1 1 d . . .
H2'A H 0.6902 1.2475 0.3833 0.022 Uiso 1 1 calc R . .
H2'B H 0.7175 1.1267 0.3801 0.022 Uiso 1 1 calc R . .
C5A C 0.2348(2) 1.08339(16) 0.35929(14) 0.0166(5) Uani 1 1 d . . .
C10A C 0.4459(2) 0.99094(17) 0.26461(14) 0.0170(5) Uani 1 1 d . . .
C3A C 0.5089(2) 1.02124(16) 0.34533(14) 0.0158(5) Uani 1 1 d . . .
C6 C 0.1252(2) 1.08355(17) 0.40834(14) 0.0191(5) Uani 1 1 d . . .
H6A H 0.1311 1.1160 0.4656 0.023 Uiso 1 1 calc R . .
C6' C 0.5201(2) 1.24523(17) 0.50491(14) 0.0190(5) Uani 1 1 d . . .
H6'A H 0.4321 1.2296 0.5241 0.023 Uiso 1 1 calc R . .
H6'B H 0.5146 1.3108 0.4715 0.023 Uiso 1 1 calc R . .
C3 C 0.6184(2) 0.95498(17) 0.37192(14) 0.0168(5) Uani 1 1 d . . .
H3A H 0.6720 0.9633 0.4270 0.020 Uiso 1 1 calc R . .
C3' C 0.7889(2) 1.19267(17) 0.50120(15) 0.0211(5) Uani 1 1 d . . .
H3'A H 0.7923 1.1274 0.5351 0.025 Uiso 1 1 calc R . .
H3'B H 0.8776 1.2063 0.4823 0.025 Uiso 1 1 calc R . .
C5' C 0.6191(2) 1.25447(17) 0.58675(14) 0.0213(5) Uani 1 1 d . . .
H5'A H 0.5924 1.3105 0.6259 0.026 Uiso 1 1 calc R . .
H5'B H 0.6207 1.1900 0.6217 0.026 Uiso 1 1 calc R . .
C9A C 0.2235(2) 1.03598(16) 0.27447(14) 0.0168(5) Uani 1 1 d . . .
C9 C 0.1040(2) 0.99243(17) 0.24126(15) 0.0205(5) Uani 1 1 d . . .
H9A H 0.0961 0.9616 0.1833 0.025 Uiso 1 1 calc R . .
C2A C 0.7404(2) 0.79750(17) 0.31803(15) 0.0213(5) Uani 1 1 d . . .
H2AA H 0.7989 0.8057 0.3734 0.032 Uiso 1 1 calc R . .
H2AB H 0.7917 0.8020 0.2659 0.032 Uiso 1 1 calc R . .
H2AC H 0.6971 0.7306 0.3184 0.032 Uiso 1 1 calc R . .
C7 C 0.0079(2) 1.03777(18) 0.37599(15) 0.0220(5) Uani 1 1 d . . .
H7A H -0.0645 1.0368 0.4116 0.026 Uiso 1 1 calc R . .
C4' C 0.8454(2) 1.2842(2) 0.63957(15) 0.0278(6) Uani 1 1 d . . .
H4'A H 0.8187 1.3401 0.6777 0.042 Uiso 1 1 calc R . .
H4'B H 0.9332 1.2984 0.6212 0.042 Uiso 1 1 calc R . .
H4'C H 0.8472 1.2199 0.6734 0.042 Uiso 1 1 calc R . .
C8 C -0.0028(2) 0.99352(19) 0.29129(15) 0.0239(5) Uani 1 1 d . . .
H8A H -0.0837 0.9639 0.2677 0.029 Uiso 1 1 calc R . .
O1 O 0.73435(16) 1.45245(13) 0.45569(10) 0.0232(4) Uani 1 1 d . . .
C100 C 0.6896(2) 1.53165(18) 0.51051(15) 0.0230(5) Uani 1 1 d . . .
H10B H 0.6220 1.5035 0.5471 0.028 Uiso 1 1 calc R . .
H10C H 0.6475 1.5857 0.4713 0.028 Uiso 1 1 calc R . .
C101 C 0.7988(2) 1.5790(2) 0.57273(16) 0.0296(6) Uani 1 1 d . . .
H10D H 0.7606 1.6305 0.6113 0.036 Uiso 1 1 calc R . .
H10E H 0.8402 1.5251 0.6125 0.036 Uiso 1 1 calc R . .
C102 C 0.9029(3) 1.6294(2) 0.52252(19) 0.0358(7) Uani 1 1 d . . .
H10F H 0.9707 1.6588 0.5657 0.054 Uiso 1 1 calc R . .
H10G H 0.8628 1.6837 0.4839 0.054 Uiso 1 1 calc R . .
H10H H 0.9428 1.5783 0.4854 0.054 Uiso 1 1 calc R . .
H10A H 0.309(2) 1.0045(18) 0.1718(16) 0.021(6) Uiso 1 1 d . . .
H1A H 0.744(3) 1.399(2) 0.492(2) 0.055(10) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10A 1.730(2) . ?
S1 C2 1.739(2) . ?
N1' C4 1.385(3) . ?
N1' C2' 1.456(3) . ?
N1' C6' 1.461(3) . ?
N4' C3' 1.462(3) . ?
N4' C4' 1.468(3) . ?
N4' C5' 1.473(3) . ?
C2 C3 1.347(3) . ?
C2 C2A 1.497(3) . ?
N10 C10A 1.397(3) . ?
N10 C9A 1.418(3) . ?
N5 C4 1.285(3) . ?
N5 C5A 1.413(3) . ?
C4 C3A 1.470(3) . ?
C2' C3' 1.515(3) . ?
C5A C6 1.394(3) . ?
C5A C9A 1.404(3) . ?
C10A C3A 1.370(3) . ?
C3A C3 1.441(3) . ?
C6 C7 1.386(3) . ?
C6' C5' 1.516(3) . ?
C9A C9 1.395(3) . ?
C9 C8 1.378(3) . ?
C7 C8 1.385(3) . ?
O1 C100 1.421(3) . ?
C100 C101 1.515(3) . ?
C101 C102 1.508(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
_geom_angle_publ_flag
C10A S1 C2 91.92(10) . . ?
C4 N1' C2' 123.39(18) . . ?
C4 N1' C6' 118.34(18) . . ?
C2' N1' C6' 111.06(17) . . ?
C3' N4' C4' 110.61(18) . . ?
C3' N4' C5' 108.95(17) . . ?
C4' N4' C5' 109.64(18) . . ?
C3 C2 C2A 129.5(2) . . ?
C3 C2 S1 110.48(17) . . ?
C2A C2 S1 119.99(16) . . ?
C10A N10 C9A 114.37(17) . . ?
C4 N5 C5A 123.88(19) . . ?
N5 C4 N1' 117.64(19) . . ?
N5 C4 C3A 126.08(19) . . ?
N1' C4 C3A 116.17(19) . . ?
N1' C2' C3' 109.50(18) . . ?
C6 C5A C9A 118.1(2) . . ?
C6 C5A N5 116.07(19) . . ?
C9A C5A N5 125.6(2) . . ?
C3A C10A N10 126.3(2) . . ?
C3A C10A S1 111.99(16) . . ?
N10 C10A S1 121.61(16) . . ?
C10A C3A C3 110.93(19) . . ?
C10A C3A C4 121.64(19) . . ?
C3 C3A C4 127.43(18) . . ?
C7 C6 C5A 121.9(2) . . ?
N1' C6' C5' 109.41(18) . . ?
C2 C3 C3A 114.66(19) . . ?
N4' C3' C2' 110.56(18) . . ?
N4' C5' C6' 110.58(18) . . ?
C9 C9A C5A 119.8(2) . . ?
C9 C9A N10 119.73(19) . . ?
C5A C9A N10 120.5(2) . . ?
C8 C9 C9A 120.9(2) . . ?
C8 C7 C6 119.4(2) . . ?
C9 C8 C7 120.0(2) . . ?
O1 C100 C101 113.1(2) . . ?
C102 C101 C100 112.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.072

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 1-propanol
