#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:08:48 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257489 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/97/7239706.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_7239706
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            'C18 H36 N2 O8'
_chemical_formula_weight         408.49
_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                 99.780(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5328(10)
_cell_length_b                   6.1123(5)
_cell_length_c                   16.0138(14)
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      29.1780
_cell_measurement_theta_min      4.3600
_cell_volume                     1112.44(17)
_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      150.0(1)
_diffrn_detector_area_resol_mean 16.1048
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.872
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2690
_diffrn_reflns_point_group_measured_fraction_full 0.745
_diffrn_reflns_point_group_measured_fraction_max 0.617
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.069
_diffrn_reflns_theta_min         3.599
_diffrn_source                   'fine-focus sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74806
_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    1.219
_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         0.252
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1838
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0398
_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)+(0.0575P)²+0.2355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.301
_reflns_Friedel_fraction_full    0.435
_reflns_Friedel_fraction_max     0.313
_reflns_number_gt                1720
_reflns_number_total             1838
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01625b2.cif
_cod_data_source_block           oxal_lt
_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               7239706
_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.
;
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.981
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 0.76793(13) 0.4112(3) 0.39852(9) 0.0207(3) Uani 1 1 d . .
O7 O 0.60062(13) 0.5067(3) 0.31433(10) 0.0233(4) Uani 1 1 d . .
H7 H 0.592614 0.585389 0.354427 0.035 Uiso 1 1 calc R U
O12 O 0.58480(14) 1.1123(3) 0.44745(10) 0.0235(4) Uani 1 1 d . .
O11 O 0.55119(14) 0.7534(3) 0.43288(11) 0.0275(4) Uani 1 1 d . .
N1 N 0.83253(16) -0.0448(3) 0.43329(11) 0.0222(4) Uani 1 1 d . .
H1A H 0.884770 0.061180 0.448512 0.033 Uiso 1 1 calc R U
H1B H 0.851332 -0.161066 0.466277 0.033 Uiso 1 1 calc R U
H1C H 0.761159 0.001971 0.438853 0.033 Uiso 1 1 calc R U
C5 C 0.69380(17) 0.3793(4) 0.33605(14) 0.0181(4) Uani 1 1 d . .
C14 C 0.53948(17) 0.9377(4) 0.46491(12) 0.0175(4) Uani 1 1 d . .
C2 C 0.83309(19) -0.1058(4) 0.34345(14) 0.0206(5) Uani 1 1 d . .
H2A H 0.770630 -0.210995 0.326244 0.025 Uiso 1 1 calc R U
H2B H 0.907050 -0.178037 0.340104 0.025 Uiso 1 1 calc R U
C3 C 0.81742(18) 0.0826(4) 0.28074(13) 0.0184(4) Uani 1 1 d . .
H3 H 0.879545 0.190530 0.298607 0.022 Uiso 1 1 calc R U
C8 C 0.8338(2) -0.0110(4) 0.19493(14) 0.0247(5) Uani 1 1 d . .
H8A H 0.905362 -0.097499 0.203416 0.030 Uiso 1 1 calc R U
H8B H 0.768923 -0.109800 0.175805 0.030 Uiso 1 1 calc R U
C4 C 0.69753(18) 0.1970(4) 0.27438(14) 0.0212(5) Uani 1 1 d . .
H4A H 0.675353 0.254524 0.217455 0.025 Uiso 1 1 calc R U
H4B H 0.639201 0.088602 0.282884 0.025 Uiso 1 1 calc R U
C9 C 0.8409(2) 0.1530(6) 0.12405(15) 0.0367(7) Uani 1 1 d . .
H9 H 0.766541 0.233850 0.112733 0.044 Uiso 1 1 calc R U
C11 C 0.8556(3) 0.0307(8) 0.04421(19) 0.0652(12) Uani 1 1 d . .
H11A H 0.927986 -0.050169 0.054113 0.098 Uiso 1 1 calc R U
H11B H 0.857189 0.133269 -0.000987 0.098 Uiso 1 1 calc R U
H11C H 0.790910 -0.068403 0.028925 0.098 Uiso 1 1 calc R U
C10 C 0.9401(4) 0.3168(7) 0.1482(2) 0.0632(11) Uani 1 1 d . .
H10A H 0.924473 0.404675 0.194696 0.095 Uiso 1 1 calc R U
H10B H 0.945518 0.409266 0.100537 0.095 Uiso 1 1 calc R U
H10C H 1.013019 0.239898 0.164556 0.095 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 123.2(2) .
O6 C5 C4 124.60(19) .
O7 C5 C4 112.20(18) .
O12 C14 O11 126.98(19) .
O12 C14 C14 118.78(12) 2_656
O11 C14 C14 114.23(13) 2_656
N1 C2 C3 115.47(18) .
C2 C3 C8 106.94(18) .
C2 C3 C4 113.16(18) .
C8 C3 C4 110.95(17) .
C9 C8 C3 116.9(2) .
C5 C4 C3 114.95(17) .
C11 C9 C10 110.6(3) .
C11 C9 C8 109.3(3) .
C10 C9 C8 112.1(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 C5 1.216(3) .
O7 C5 1.325(3) .
O12 C14 1.241(3) .
O11 C14 1.255(3) .
N1 C2 1.487(3) .
C5 C4 1.495(3) .
C14 C14 1.562(4) 2_656
C2 C3 1.519(3) .
C3 C8 1.530(3) .
C3 C4 1.537(3) .
C8 C9 1.527(4) .
C9 C11 1.515(4) .
C9 C10 1.520(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O7 H7 O11 0.82 1.75 2.563(2) 170.7 . yes
N1 H1A O11 0.89 2.30 3.112(3) 151.7 3_545 yes
N1 H1A O11 0.89 2.25 2.956(3) 136.2 4_646 yes
N1 H1B O12 0.89 2.01 2.886(3) 169.7 4_636 yes
N1 H1C O12 0.89 2.17 3.059(2) 177.8 1_545 yes
C2 H2A O6 0.97 2.59 3.207(3) 122.0 1_545 yes
C2 H2A O7 0.97 2.59 3.548(3) 167.8 1_545 yes
C2 H2B O7 0.97 2.60 3.271(3) 126.8 3_545 yes
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 174.05(17)
N1 C2 C3 C4 -63.5(2)
C2 C3 C8 C9 -170.88(19)
C4 C3 C8 C9 65.3(3)
O6 C5 C4 C3 -15.3(3)
O7 C5 C4 C3 163.68(19)
C2 C3 C4 C5 88.4(2)
C8 C3 C4 C5 -151.42(19)
C3 C8 C9 C11 -179.3(2)
C3 C8 C9 C10 57.6(3)
