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#$Date: 2025-05-01 11:33:25 +0300 (Thu, 01 May 2025) $
#$Revision: 299470 $
#$URL: file:///home/coder/svn-repositories/cod/cif/3/00/04/3000442.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_3000442
loop_
_publ_author_name
'Gogoi, Diptajyoti'
'Sasaki, Toshiyuki'
'Nakane, Takanori'
'Kawamoto, Akihiro'
'Hojo, Hironobu'
'Kurisu, Genji'
'Thakuria, Ranjit'
_publ_section_title
;
 Structure Elucidation of Olanzapine Molecular Salts by Combining
 Mechanochemistry and Micro-Electron Diffraction
;
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5821
_journal_page_last               5826
_journal_paper_doi               10.1021/acs.cgd.3c00432
_journal_volume                  23
_journal_year                    2023
_chemical_formula_moiety         '2(C4 H5 O4), C5 H14 N2, H2 O'
_chemical_formula_sum            'C13 H26 N2 O9'
_chemical_formula_weight         354.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                104.04
_cell_angle_beta                 97.60
_cell_angle_gamma                97.50
_cell_formula_units_Z            2
_cell_length_a                   6.605
_cell_length_b                   8.935
_cell_length_c                   15.061
_cell_measurement_reflns_used    8948
_cell_measurement_temperature    79
_cell_measurement_theta_max      0.8980291984245176
_cell_measurement_theta_min      0.1560398850479103
_cell_volume                     842.398
_computing_cell_refinement
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection
'Verlox (Thermo Fisher Scientific) and SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      79
_diffrn_measured_fraction_theta_full 0.872
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_device_type
;
Talos Arctica G2
;
_diffrn_radiation_type           electrons
_diffrn_radiation_wavelength     0.02508
_diffrn_reflns_av_R_equivalents  0.3127
_diffrn_reflns_av_unetI/netI     0.5636
_diffrn_reflns_Laue_measured_fraction_full 0.872
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45547
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        0.862
_diffrn_reflns_theta_max         0.898
_diffrn_reflns_theta_min         0.128
_diffrn_source                   electrons
_exptl_absorpt_coefficient_mu    0.000
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             132
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       10953(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.2214
_refine_ls_R_factor_gt           0.1475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4024
_refine_ls_wR_factor_ref         0.4200
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1338
_reflns_number_total             3004
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            SUCA.cif
_cod_data_source_block           suca
_cod_depositor_comments
'Releasing structure 3000442 into public domain as published material.'
_cod_original_cell_volume        842.2
_cod_database_code               3000442
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O9-H9C = O9-H9D
 0.82 with sigma of 0.02
 H9C-O9 \\sim O9-H9D
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 N2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C7(H7A,H7B), C6(H6A,H6B), C9(H9A,H9B), C2(H2A,H2B), C10(H10A,
 H10B), N1(H1A,H1B), C3(H3A,H3B), C12(H12A,H12B)
4.c Tetrahedral OH refined with riding coordinates:
 O1(H1), O5(H5)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 1.0667(9) 0.7732(7) 0.1429(7) 0.040(3) Uani 1 1 d . . . . .
C8 C 0.8721(9) 0.7711(7) 0.1422(8) 0.033(3) Uani 1 1 d . . . . .
O1 O 0.9744(8) -0.0945(7) 0.3861(7) 0.040(3) Uani 1 1 d . . . . .
H1 H 1.022027 -0.012553 0.375223 0.060 Uiso 1 1 calc R U . . .
O6 O 0.5529(8) 1.1569(7) 0.1052(7) 0.045(3) Uani 1 1 d . . . . .
N2 N 1.1651(9) 0.4941(7) 0.1643(7) 0.038(2) Uani 1 1 d . . . . .
H2 H 1.105121 0.588122 0.162095 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4535(10) 1.0405(7) 0.1171(8) 0.038(3) Uani 1 1 d . . . . .
C1 C 0.7777(10) -0.0927(8) 0.3972(8) 0.035(3) Uani 1 1 d . . . . .
O5 O 0.2531(9) 1.0357(7) 0.1200(7) 0.046(3) Uani 1 1 d . . . . .
H5 H 0.202901 0.949317 0.124255 0.069 Uiso 1 1 calc R U . . .
O9 O 0.7813(9) 0.5263(7) 0.4601(8) 0.051(3) Uani 1 1 d D . . . .
C11 C 1.3264(10) 0.5320(7) 0.2520(8) 0.036(2) Uani 1 1 d . . . . .
H11A H 1.432045 0.617797 0.251277 0.043 Uiso 1 1 calc R U . . .
H11B H 1.392834 0.441626 0.252983 0.043 Uiso 1 1 calc R U . . .
O4 O 0.1511(8) 0.1506(6) 0.3503(7) 0.042(3) Uani 1 1 d . . . . .
C7 C 0.7790(9) 0.9168(7) 0.1278(8) 0.035(3) Uani 1 1 d . . . . .
H7A H 0.842531 1.006931 0.178827 0.042 Uiso 1 1 calc R U . . .
H7B H 0.813207 0.938323 0.070947 0.042 Uiso 1 1 calc R U . . .
O2 O 0.6723(9) -0.2066(7) 0.4112(8) 0.050(3) Uani 1 1 d . . . . .
C6 C 0.5455(10) 0.8958(8) 0.1223(7) 0.034(3) Uani 1 1 d . . . . .
H6A H 0.481835 0.811508 0.067954 0.040 Uiso 1 1 calc R U . . .
H6B H 0.510857 0.864385 0.176504 0.040 Uiso 1 1 calc R U . . .
O3 O 0.4653(9) 0.2868(7) 0.3607(8) 0.057(3) Uani 1 1 d . . . . .
C9 C 0.9001(10) 0.4112(8) 0.2553(8) 0.039(2) Uani 1 1 d . . . . .
H9A H 0.830349 0.499982 0.254348 0.047 Uiso 1 1 calc R U . . .
H9B H 0.797578 0.323216 0.255637 0.047 Uiso 1 1 calc R U . . .
C2 C 0.6851(9) 0.0485(8) 0.3867(8) 0.044(3) Uani 1 1 d . . . . .
H2A H 0.730088 0.080137 0.334277 0.052 Uiso 1 1 calc R U . . .
H2B H 0.738388 0.133845 0.441879 0.052 Uiso 1 1 calc R U . . .
C10 C 0.9995(10) 0.3708(7) 0.1701(8) 0.039(2) Uani 1 1 d . . . . .
H10A H 1.056946 0.275971 0.169000 0.047 Uiso 1 1 calc R U . . .
H10B H 0.893098 0.348786 0.115517 0.047 Uiso 1 1 calc R U . . .
C13 C 1.2671(12) 0.4535(8) 0.0857(9) 0.045(2) Uani 1 1 d . . . . .
H13A H 1.390749 0.528626 0.094053 0.068 Uiso 1 1 calc R U . . .
H13B H 1.176109 0.453541 0.030446 0.068 Uiso 1 1 calc R U . . .
H13C H 1.302819 0.351261 0.079988 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3550(10) 0.1652(8) 0.3622(8) 0.040(3) Uani 1 1 d . . . . .
O8 O 0.7494(9) 0.6563(7) 0.1503(8) 0.052(3) Uani 1 1 d . . . . .
N1 N 1.0619(9) 0.4504(7) 0.3413(7) 0.037(2) Uani 1 1 d . . . . .
H1A H 1.002819 0.479888 0.391052 0.045 Uiso 1 1 calc R U . . .
H1B H 1.115595 0.365404 0.345063 0.045 Uiso 1 1 calc R U . . .
C3 C 0.4518(9) 0.0226(7) 0.3723(8) 0.038(3) Uani 1 1 d . . . . .
H3A H 0.407158 -0.009983 0.424581 0.045 Uiso 1 1 calc R U . . .
H3B H 0.398884 -0.062513 0.317009 0.045 Uiso 1 1 calc R U . . .
C12 C 1.2300(11) 0.5774(8) 0.3409(8) 0.038(2) Uani 1 1 d . . . . .
H12A H 1.335935 0.595564 0.395258 0.046 Uiso 1 1 calc R U . . .
H12B H 1.174744 0.673437 0.343241 0.046 Uiso 1 1 calc R U . . .
H9C H 0.668(4) 0.466(4) 0.441(4) 0.045(11) Uiso 1 1 d D . . . .
H9D H 0.745(13) 0.609(7) 0.454(9) 0.16(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 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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
O7 C8 C7 118.4(6) . .
O8 C8 O7 123.9(6) . .
O8 C8 C7 117.6(5) . .
C1 O1 H1 109.5 . .
C11 N2 H2 108.5 . .
C10 N2 H2 108.5 . .
C10 N2 C11 108.1(8) . .
C13 N2 H2 108.5 . .
C13 N2 C11 108.3(6) . .
C13 N2 C10 114.7(7) . .
O6 C5 O5 119.2(6) . .
O6 C5 C6 122.8(6) . .
O5 C5 C6 117.9(6) . .
O1 C1 C2 117.9(6) . .
O2 C1 O1 120.8(6) . .
O2 C1 C2 121.1(6) . .
C5 O5 H5 109.5 . .
H9C O9 H9D 100(7) . .
N2 C11 H11A 109.2 . .
N2 C11 H11B 109.2 . .
N2 C11 C12 112.0(6) . .
H11A C11 H11B 107.9 . .
C12 C11 H11A 109.2 . .
C12 C11 H11B 109.2 . .
C8 C7 H7A 108.9 . .
C8 C7 H7B 108.9 . .
H7A C7 H7B 107.7 . .
C6 C7 C8 113.3(5) . .
C6 C7 H7A 108.9 . .
C6 C7 H7B 108.9 . .
C5 C6 C7 114.3(5) . .
C5 C6 H6A 108.7 . .
C5 C6 H6B 108.7 . .
C7 C6 H6A 108.7 . .
C7 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
H9A C9 H9B 108.2 . .
C10 C9 H9A 109.7 . .
C10 C9 H9B 109.7 . .
N1 C9 H9A 109.7 . .
N1 C9 H9B 109.7 . .
N1 C9 C10 110.0(6) . .
C1 C2 H2A 108.7 . .
C1 C2 H2B 108.7 . .
C1 C2 C3 114.2(5) . .
H2A C2 H2B 107.6 . .
C3 C2 H2A 108.7 . .
C3 C2 H2B 108.7 . .
N2 C10 C9 114.4(8) . .
N2 C10 H10A 108.7 . .
N2 C10 H10B 108.7 . .
C9 C10 H10A 108.7 . .
C9 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
N2 C13 H13A 109.5 . .
N2 C13 H13B 109.5 . .
N2 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O4 C4 C3 117.9(6) . .
O3 C4 O4 121.7(6) . .
O3 C4 C3 120.4(6) . .
C9 N1 H1A 109.3 . .
C9 N1 H1B 109.3 . .
H1A N1 H1B 108.0 . .
C12 N1 C9 111.7(7) . .
C12 N1 H1A 109.3 . .
C12 N1 H1B 109.3 . .
C2 C3 C4 114.9(5) . .
C2 C3 H3A 108.5 . .
C2 C3 H3B 108.5 . .
C4 C3 H3A 108.5 . .
C4 C3 H3B 108.5 . .
H3A C3 H3B 107.5 . .
C11 C12 H12A 109.7 . .
C11 C12 H12B 109.7 . .
N1 C12 C11 110.0(7) . .
N1 C12 H12A 109.7 . .
N1 C12 H12B 109.7 . .
H12A C12 H12B 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O7 C8 1.281(8) .
C8 C7 1.560(8) .
C8 O8 1.262(9) .
O1 H1 0.8200 .
O1 C1 1.334(8) .
O6 C5 1.219(9) .
N2 H2 0.9800 .
N2 C11 1.521(13) .
N2 C10 1.475(9) .
N2 C13 1.432(14) .
C5 O5 1.325(8) .
C5 C6 1.514(8) .
C1 O2 1.234(8) .
C1 C2 1.504(8) .
O5 H5 0.8200 .
O9 H9C 0.837(16) .
O9 H9D 0.832(16) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.546(14) .
O4 C4 1.320(8) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C6 1.517(9) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
O3 C4 1.233(9) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.506(14) .
C9 N1 1.502(13) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.506(8) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C4 C3 1.528(8) .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
N1 C12 1.482(8) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O7 C8 C7 C6 176.4(10) . . . .
C8 C7 C6 C5 174.8(9) . . . .
O1 C1 C2 C3 162.9(10) . . . .
O6 C5 C6 C7 9.7(16) . . . .
N2 C11 C12 N1 56.5(7) . . . .
C1 C2 C3 C4 179.6(9) . . . .
O5 C5 C6 C7 -174.4(10) . . . .
C11 N2 C10 C9 56.2(7) . . . .
O4 C4 C3 C2 -179.4(10) . . . .
O2 C1 C2 C3 -13.6(15) . . . .
O3 C4 C3 C2 4.1(16) . . . .
C9 N1 C12 C11 -55.8(8) . . . .
C10 N2 C11 C12 -55.1(7) . . . .
C10 C9 N1 C12 55.4(7) . . . .
C13 N2 C11 C12 180.0(5) . . . .
C13 N2 C10 C9 177.1(8) . . . .
O8 C8 C7 C6 -2.0(14) . . . .
N1 C9 C10 N2 -56.8(8) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
_cod_related_entry_description
1 XRDa 00126 DOI:10.51093/xrd-00126
