#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/89/4508983.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4508983
loop_
_publ_author_name
'Reddy, L. Sreenivas'
'Bethune, Sarah J.'
'Kampf, Jeff W.'
'Rodríguez-Hornedo, Naír'
_publ_section_title
;
 Cocrystals and Salts of Gabapentin: pH Dependent Cocrystal Stability and
 Solubility
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              378
_journal_paper_doi               10.1021/cg800587y
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C9 H17 N O2, C7 H6 O3'
_chemical_formula_sum            'C16 H23 N O5'
_chemical_formula_weight         309.35
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8276(12)
_cell_length_b                   25.380(2)
_cell_length_c                   9.5029(9)
_cell_measurement_reflns_used    9804
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      23.36
_cell_measurement_theta_min      2.76
_cell_volume                     3093.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART-APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            73413
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2.10) Bruker/Siemens area
  detector absorption and other corrections, University of
  Gottingen, Germany 2003.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0533P)²+1.2715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                3585
_reflns_number_total             3874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800587ysup1.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_sg_symbol_H-M      Pccn
_cod_database_code               4508983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
O1 O 0.12806(5) 0.43893(3) 0.22057(8) 0.01573(16) Uani 1 1 d .
O2 O 0.27428(5) 0.48384(3) 0.18729(8) 0.01511(16) Uani 1 1 d .
O3 O 0.35526(6) 0.56108(3) 0.94393(8) 0.01755(16) Uani 1 1 d .
O4 O 0.19060(5) 0.54171(3) 1.00064(8) 0.01552(16) Uani 1 1 d .
O5 O -0.03582(6) 0.64884(3) 0.68674(8) 0.01897(17) Uani 1 1 d .
H4 H 0.2218(14) 0.5209(7) 1.0669(19) 0.045(5) Uiso 1 1 d .
H5 H -0.0674(14) 0.6204(7) 0.7229(18) 0.041(5) Uiso 1 1 d .
N1 N 0.48283(7) 0.47921(3) 0.22506(9) 0.01505(18) Uani 1 1 d .
H1A H 0.5239(12) 0.5062(6) 0.2544(17) 0.026(4) Uiso 1 1 d .
H1B H 0.5186(12) 0.4637(6) 0.1520(16) 0.026(4) Uiso 1 1 d .
H1C H 0.4184(13) 0.4900(6) 0.1971(15) 0.023(4) Uiso 1 1 d .
C1 C 0.22375(7) 0.44618(4) 0.24184(10) 0.01188(18) Uani 1 1 d .
C2 C 0.28040(7) 0.40896(4) 0.34129(10) 0.01207(18) Uani 1 1 d .
H2A H 0.2400 0.3758 0.3457 0.014 Uiso 1 1 calc R
H2B H 0.2786 0.4248 0.4365 0.014 Uiso 1 1 calc R
C3 C 0.39495(7) 0.39452(4) 0.30815(10) 0.01086(18) Uani 1 1 d .
C4 C 0.40766(7) 0.37578(4) 0.15462(10) 0.01160(18) Uani 1 1 d .
H4A H 0.3792 0.4030 0.0907 0.014 Uiso 1 1 calc R
H4B H 0.4828 0.3718 0.1335 0.014 Uiso 1 1 calc R
C5 C 0.35263(8) 0.32353(4) 0.12562(10) 0.01449(19) Uani 1 1 d .
H5B H 0.2766 0.3279 0.1394 0.017 Uiso 1 1 calc R
H5C H 0.3647 0.3130 0.0266 0.017 Uiso 1 1 calc R
C6 C 0.39286(8) 0.28040(4) 0.22348(11) 0.0170(2) Uani 1 1 d .
H6A H 0.4680 0.2744 0.2057 0.020 Uiso 1 1 calc R
H6B H 0.3553 0.2471 0.2042 0.020 Uiso 1 1 calc R
C7 C 0.37673(8) 0.29621(4) 0.37702(10) 0.0164(2) Uani 1 1 d .
H7A H 0.4073 0.2690 0.4390 0.020 Uiso 1 1 calc R
H7B H 0.3011 0.2982 0.3972 0.020 Uiso 1 1 calc R
C8 C 0.42721(8) 0.34943(4) 0.40893(10) 0.01379(19) Uani 1 1 d .
H8A H 0.5039 0.3453 0.4047 0.017 Uiso 1 1 calc R
H8B H 0.4089 0.3598 0.5063 0.017 Uiso 1 1 calc R
C9 C 0.46983(8) 0.44027(4) 0.34190(10) 0.01445(19) Uani 1 1 d .
H9A H 0.4437 0.4590 0.4261 0.017 Uiso 1 1 calc R
H9B H 0.5390 0.4254 0.3656 0.017 Uiso 1 1 calc R
C10 C 0.26167(8) 0.56811(4) 0.92931(10) 0.01339(19) Uani 1 1 d .
C11 C 0.21662(8) 0.60735(4) 0.82958(10) 0.01358(19) Uani 1 1 d .
C12 C 0.10949(7) 0.60955(4) 0.80742(10) 0.01319(19) Uani 1 1 d .
H12A H 0.0646 0.5863 0.8570 0.016 Uiso 1 1 calc R
C13 C 0.06780(8) 0.64580(4) 0.71259(10) 0.01477(19) Uani 1 1 d .
C14 C 0.13384(9) 0.68016(4) 0.64123(12) 0.0202(2) Uani 1 1 d .
H14A H 0.1059 0.7050 0.5766 0.024 Uiso 1 1 calc R
C15 C 0.24044(9) 0.67804(4) 0.66470(13) 0.0228(2) Uani 1 1 d .
H15A H 0.2853 0.7016 0.6160 0.027 Uiso 1 1 calc R
C16 C 0.28241(8) 0.64187(4) 0.75857(12) 0.0192(2) Uani 1 1 d .
H16A H 0.3555 0.6407 0.7742 0.023 Uiso 1 1 calc R
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
O1 C1 O2 122.99(9)
O1 C1 C2 118.39(8)
O2 C1 C2 118.60(8)
C1 C2 C3 118.33(8)
C9 C3 C4 111.29(8)
C9 C3 C2 111.79(8)
C4 C3 C2 111.46(7)
C9 C3 C8 105.16(7)
C4 C3 C8 109.20(7)
C2 C3 C8 107.64(7)
C5 C4 C3 112.91(8)
C6 C5 C4 110.89(8)
C5 C6 C7 110.35(8)
C6 C7 C8 111.37(8)
C7 C8 C3 114.65(8)
N1 C9 C3 114.39(8)
O3 C10 O4 123.13(9)
O3 C10 C11 123.42(9)
O4 C10 C11 113.46(8)
C16 C11 C12 120.04(9)
C16 C11 C10 119.58(9)
C12 C11 C10 120.38(9)
C11 C12 C13 120.20(9)
O5 C13 C14 118.24(9)
O5 C13 C12 122.10(9)
C14 C13 C12 119.66(9)
C15 C14 C13 119.83(10)
C14 C15 C16 120.75(10)
C15 C16 C11 119.52(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2575(12)
O2 C1 1.2658(12)
O3 C10 1.2217(12)
O4 C10 1.3189(12)
O5 C13 1.3539(12)
N1 C9 1.4958(13)
C1 C2 1.5210(13)
C2 C3 1.5468(13)
C3 C9 1.5407(13)
C3 C4 1.5431(13)
C3 C8 1.5485(13)
C4 C5 1.5274(13)
C5 C6 1.5263(14)
C6 C7 1.5274(14)
C7 C8 1.5285(14)
C10 C11 1.4913(13)
C11 C16 1.3911(14)
C11 C12 1.3914(13)
C12 C13 1.3944(13)
C13 C14 1.3922(14)
C14 C15 1.3865(16)
C15 C16 1.3887(15)
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
O4 H4 O2 0.914(19) 1.627(19) 2.5408(10) 178.5(18) 1_556
O5 H5 O1 0.896(19) 1.779(19) 2.6718(11) 174.7(17) 5_566
N1 H1A O1 0.908(16) 1.944(16) 2.8379(11) 167.6(14) 4_565
N1 H1B O3 0.920(16) 1.961(16) 2.8174(12) 154.1(13) 5_666
N1 H1C O2 0.910(16) 1.858(16) 2.7018(12) 153.3(13) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146822
