#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:08:48 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257489 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/97/7239705.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_7239705
loop_
_publ_author_name
'Khandavilli, U. B. Rao'
'Yousuf, Mustafa'
'Schaller, Barbara E.'
'Steendam, René R. E.'
'Keshavarz, Leila'
'McArdle, Patrick'
'Frawley, Patrick J.'
_publ_section_title
;
 Plastically bendable pregabalin multi-component systems with improved
 tabletability and compressibility
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              412
_journal_page_last               415
_journal_paper_doi               10.1039/C9CE01625B
_journal_volume                  22
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_sum            'C9 H18 N O4'
_chemical_formula_weight         204.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-11-22 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.628(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7250(10)
_cell_length_b                   6.1271(4)
_cell_length_c                   16.0527(15)
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    294.0(3)
_cell_measurement_theta_max      28.9310
_cell_measurement_theta_min      3.9270
_cell_volume                     1136.99(16)
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_collection       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_molecular_graphics
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294.0(3)
_diffrn_detector_area_resol_mean 16.1048
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5043
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.202
_diffrn_reflns_theta_min         3.525
_diffrn_source                   'fine-focus sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018)
empirical absorption correction using spherical harmonics,
 implemented in scale3 abspack scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 867 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2580
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0580P)²+0.1627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.781
_reflns_number_gt                2271
_reflns_number_total             2580
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01625b2.cif
_cod_data_source_block           oxal
_cod_depositor_comments
;Adding full bibliography for 7239704--7239707.cif.

 Adding full bibliography for 7239704--7239707.cif.
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7239705
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
O6 O 0.76550(14) 0.4115(3) 0.39987(11) 0.0384(4) Uani 1 1 d . .
O7 O 0.60064(15) 0.5027(3) 0.31699(12) 0.0433(5) Uani 1 1 d . .
H7 H 0.590118 0.575496 0.357906 0.065 Uiso 1 1 calc R U
O12 O 0.58214(19) 1.1073(3) 0.44762(13) 0.0518(5) Uani 1 1 d . .
O11 O 0.5520(2) 0.7499(4) 0.43454(15) 0.0621(6) Uani 1 1 d . .
N1 N 0.8304(2) -0.0502(3) 0.43217(13) 0.0407(5) Uani 1 1 d . .
H1A H 0.881161 0.055607 0.448640 0.061 Uiso 1 1 calc R U
H1B H 0.848786 -0.167887 0.464090 0.061 Uiso 1 1 calc R U
H1C H 0.759782 -0.005415 0.437619 0.061 Uiso 1 1 calc R U
C5 C 0.69346(19) 0.3796(3) 0.33805(15) 0.0305(5) Uani 1 1 d . .
C14 C 0.53881(18) 0.9348(4) 0.46580(14) 0.0310(5) Uani 1 1 d . .
C2 C 0.8327(2) -0.1049(4) 0.34262(17) 0.0383(6) Uani 1 1 d . .
H2A H 0.772215 -0.210851 0.324211 0.046 Uiso 1 1 calc R U
H2B H 0.906110 -0.174121 0.339083 0.046 Uiso 1 1 calc R U
C3 C 0.8166(2) 0.0873(4) 0.28167(15) 0.0323(5) Uani 1 1 d . .
H3 H 0.876981 0.195290 0.300766 0.039 Uiso 1 1 calc R U
C8 C 0.8346(2) 0.0004(5) 0.19533(17) 0.0448(6) Uani 1 1 d . .
H8A H 0.904763 -0.086408 0.203482 0.054 Uiso 1 1 calc R U
H8B H 0.770856 -0.096665 0.174465 0.054 Uiso 1 1 calc R U
C4 C 0.6983(2) 0.1990(4) 0.27604(17) 0.0392(5) Uani 1 1 d . .
H4A H 0.676061 0.257244 0.219452 0.047 Uiso 1 1 calc R U
H4B H 0.641507 0.089480 0.284367 0.047 Uiso 1 1 calc R U
C9 C 0.8436(3) 0.1704(7) 0.1268(2) 0.0671(10) Uani 1 1 d . .
H9 H 0.771237 0.253478 0.116404 0.081 Uiso 1 1 calc R U
C11 C 0.8573(6) 0.0540(11) 0.0460(3) 0.122(2) Uani 1 1 d . .
H11A H 0.926224 -0.033469 0.055611 0.182 Uiso 1 1 calc R U
H11B H 0.863025 0.159517 0.002724 0.182 Uiso 1 1 calc R U
H11C H 0.791443 -0.038096 0.028487 0.182 Uiso 1 1 calc R U
C10 C 0.9425(6) 0.3294(10) 0.1535(3) 0.118(2) Uani 1 1 d . .
H10A H 0.929539 0.407137 0.203014 0.177 Uiso 1 1 calc R U
H10B H 0.946352 0.431100 0.108596 0.177 Uiso 1 1 calc R U
H10C H 1.014010 0.250302 0.165862 0.177 Uiso 1 1 calc R U
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'
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_3
O6 C5 O7 123.5(2) .
O6 C5 C4 124.6(2) .
O7 C5 C4 111.9(2) .
O12 C14 O11 126.6(2) .
O12 C14 C14 119.13(15) 2_656
O11 C14 C14 114.28(16) 2_656
N1 C2 C3 115.36(19) .
C2 C3 C8 106.95(19) .
C2 C3 C4 113.3(2) .
C8 C3 C4 111.2(2) .
C9 C8 C3 116.8(3) .
C5 C4 C3 115.1(2) .
C11 C9 C10 111.1(4) .
C11 C9 C8 109.0(4) .
C10 C9 C8 111.9(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 C5 1.207(3) .
O7 C5 1.321(3) .
O12 C14 1.229(3) .
O11 C14 1.259(3) .
N1 C2 1.481(3) .
C5 C4 1.496(3) .
C14 C14 1.539(4) 2_656
C2 C3 1.523(3) .
C3 C8 1.532(3) .
C3 C4 1.536(3) .
C8 C9 1.532(5) .
C9 C11 1.511(6) .
C9 C10 1.520(7) .
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
N1 C2 C3 C8 174.1(2)
N1 C2 C3 C4 -63.0(3)
C2 C3 C8 C9 -169.7(3)
C4 C3 C8 C9 66.1(3)
O6 C5 C4 C3 -15.3(4)
O7 C5 C4 C3 164.3(2)
C2 C3 C4 C5 89.4(3)
C8 C3 C4 C5 -150.1(2)
C3 C8 C9 C11 -178.2(3)
C3 C8 C9 C10 58.5(4)
