#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/47/2224720.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2224720
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Hakim Al-arique, Q. N. M.'
'Yathirajan, H. S.'
'Narayana, B.'
_publ_section_title
;
 Gabapentin-lactum--chloranilic acid (1/1)
;
_journal_coeditor_code           NG2704
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o163
_journal_page_last               o164
_journal_paper_doi               10.1107/S1600536809053410
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H15 N O, C6 H2 Cl2 O4'
_chemical_formula_moiety         'C9 H15 N O, C6 H2 Cl2 O4'
_chemical_formula_sum            'C15 H17 Cl2 N O5'
_chemical_formula_weight         362.20
_chemical_name_common
;
Gabapentin-lactum--chloranilic acid (1/1)
;
_chemical_name_systematic
;
2-azaspiro[4.5]decan-3-one--chloranilic acid (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                102.679(9)
_cell_angle_beta                 91.934(9)
_cell_angle_gamma                98.481(10)
_cell_formula_units_Z            2
_cell_length_a                   6.6127(9)
_cell_length_b                   9.5800(11)
_cell_length_c                   13.0724(13)
_cell_measurement_reflns_used    3438
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      73.9570
_cell_measurement_theta_min      4.7637
_cell_volume                     797.23(17)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type
;
Goniometer Xcalibur diffractometer with a Ruby (Gemini Cu) detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5138
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.15
_diffrn_reflns_theta_min         4.79
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.897
_exptl_absorpt_correction_T_max  0.557
_exptl_absorpt_correction_T_min  0.200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular plate'
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0422
_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)+(0.0762P)²+0.4046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                2731
_reflns_number_total             3123
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2704.cif
_cod_data_source_block           I
_cod_original_cell_volume        797.23(16)
_cod_database_code               2224720
_cod_database_fobs_code          2224720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.07819(8) 0.35536(5) 0.25360(3) 0.02058(15) Uani d . 1 . .
Cl Cl2 0.30441(7) 0.39346(5) 0.73387(3) 0.01894(15) Uani d . 1 . .
O O1A 0.0035(2) 0.11592(14) 0.36708(11) 0.0185(3) Uani d . 1 . .
H H1A -0.0101 0.0550 0.4048 0.022 Uiso calc R 1 . .
O O2A 0.1030(2) 0.13961(14) 0.57058(11) 0.0198(3) Uani d . 1 . .
O O3A 0.3781(2) 0.63101(14) 0.62265(11) 0.0168(3) Uani d . 1 . .
H H3A 0.3800 0.6958 0.5885 0.020 Uiso calc R 1 . .
O O4A 0.2633(2) 0.61192(14) 0.41806(11) 0.0174(3) Uani d . 1 . .
C C1A 0.1342(3) 0.3619(2) 0.38385(15) 0.0142(4) Uani d . 1 . .
C C2A 0.0914(3) 0.2440(2) 0.42497(15) 0.0149(4) Uani d . 1 . .
C C3A 0.1454(3) 0.25105(19) 0.53885(15) 0.0142(4) Uani d . 1 . .
C C4A 0.2436(3) 0.3875(2) 0.60388(14) 0.0139(4) Uani d . 1 . .
C C5A 0.2870(3) 0.50807(19) 0.56472(15) 0.0134(4) Uani d . 1 . .
C C6A 0.2301(3) 0.50147(19) 0.45017(15) 0.0132(4) Uani d . 1 . .
O O1B 0.5433(2) 1.13507(14) 0.43096(11) 0.0189(3) Uani d . 1 . .
C C1B 0.4590(3) 1.03933(19) 0.35294(15) 0.0147(4) Uani d . 1 . .
N N2B 0.3806(3) 0.90640(16) 0.35775(12) 0.0158(3) Uani d . 1 . .
H H2BA 0.3923 0.8731 0.4149 0.019 Uiso calc R 1 . .
C C3B 0.2729(3) 0.8193(2) 0.26005(14) 0.0163(4) Uani d . 1 . .
H H3BA 0.1226 0.8081 0.2654 0.020 Uiso calc R 1 . .
H H3BB 0.3141 0.7220 0.2424 0.020 Uiso calc R 1 . .
C C4B 0.3395(3) 0.90694(19) 0.17620(14) 0.0155(4) Uani d . 1 . .
C C5B 0.1561(3) 0.9111(2) 0.10248(16) 0.0214(4) Uani d . 1 . .
H H5BA 0.0461 0.9484 0.1448 0.026 Uiso calc R 1 . .
H H5BB 0.1986 0.9785 0.0568 0.026 Uiso calc R 1 . .
C C6B 0.0727(4) 0.7610(2) 0.03391(17) 0.0288(5) Uani d . 1 . .
H H6BA 0.0190 0.6956 0.0791 0.035 Uiso calc R 1 . .
H H6BB -0.0418 0.7686 -0.0143 0.035 Uiso calc R 1 . .
C C7B 0.2397(4) 0.6977(3) -0.02991(17) 0.0320(5) Uani d . 1 . .
H H7BA 0.2827 0.7577 -0.0805 0.038 Uiso calc R 1 . .
H H7BB 0.1841 0.5986 -0.0705 0.038 Uiso calc R 1 . .
C C8B 0.4253(4) 0.6919(2) 0.04056(17) 0.0278(5) Uani d . 1 . .
H H8BA 0.5350 0.6579 -0.0036 0.033 Uiso calc R 1 . .
H H8BB 0.3866 0.6216 0.0847 0.033 Uiso calc R 1 . .
C C9B 0.5062(3) 0.8409(2) 0.11141(16) 0.0198(4) Uani d . 1 . .
H H9BA 0.5625 0.9073 0.0674 0.024 Uiso calc R 1 . .
H H9BB 0.6193 0.8318 0.1598 0.024 Uiso calc R 1 . .
C C10B 0.4297(3) 1.0593(2) 0.24256(15) 0.0175(4) Uani d . 1 . .
H H10A 0.5621 1.0955 0.2170 0.021 Uiso calc R 1 . .
H H10B 0.3340 1.1288 0.2394 0.021 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A O1A H1A . . 109.5 ?
C5A O3A H3A . . 109.5 ?
C2A C1A C6A . . 120.62(17) ?
C2A C1A Cl1 . . 121.97(15) ?
C6A C1A Cl1 . . 117.41(14) ?
O1A C2A C1A . . 122.13(17) ?
O1A C2A C3A . . 116.63(16) ?
C1A C2A C3A . . 121.23(16) ?
O2A C3A C4A . . 124.02(17) ?
O2A C3A C2A . . 117.66(17) ?
C4A C3A C2A . . 118.32(16) ?
C5A C4A C3A . . 121.67(17) ?
C5A C4A Cl2 . . 120.66(14) ?
C3A C4A Cl2 . . 117.67(14) ?
O3A C5A C4A . . 121.97(17) ?
O3A C5A C6A . . 118.01(16) ?
C4A C5A C6A . . 120.03(16) ?
O4A C6A C1A . . 123.11(17) ?
O4A C6A C5A . . 118.78(16) ?
C1A C6A C5A . . 118.10(15) ?
O1B C1B N2B . . 123.96(17) ?
O1B C1B C10B . . 125.82(16) ?
N2B C1B C10B . . 110.21(16) ?
C1B N2B C3B . . 114.19(15) ?
C1B N2B H2BA . . 122.9 ?
C3B N2B H2BA . . 122.9 ?
N2B C3B C4B . . 104.11(15) ?
N2B C3B H3BA . . 110.9 ?
C4B C3B H3BA . . 110.9 ?
N2B C3B H3BB . . 110.9 ?
C4B C3B H3BB . . 110.9 ?
H3BA C3B H3BB . . 109.0 ?
C5B C4B C9B . . 109.57(15) ?
C5B C4B C10B . . 111.96(15) ?
C9B C4B C10B . . 109.81(16) ?
C5B C4B C3B . . 111.08(16) ?
C9B C4B C3B . . 110.64(15) ?
C10B C4B C3B . . 103.66(14) ?
C6B C5B C4B . . 111.76(17) ?
C6B C5B H5BA . . 109.3 ?
C4B C5B H5BA . . 109.3 ?
C6B C5B H5BB . . 109.3 ?
C4B C5B H5BB . . 109.3 ?
H5BA C5B H5BB . . 107.9 ?
C7B C6B C5B . . 110.90(19) ?
C7B C6B H6BA . . 109.5 ?
C5B C6B H6BA . . 109.5 ?
C7B C6B H6BB . . 109.5 ?
C5B C6B H6BB . . 109.5 ?
H6BA C6B H6BB . . 108.0 ?
C6B C7B C8B . . 111.52(18) ?
C6B C7B H7BA . . 109.3 ?
C8B C7B H7BA . . 109.3 ?
C6B C7B H7BB . . 109.3 ?
C8B C7B H7BB . . 109.3 ?
H7BA C7B H7BB . . 108.0 ?
C7B C8B C9B . . 111.18(17) ?
C7B C8B H8BA . . 109.4 ?
C9B C8B H8BA . . 109.4 ?
C7B C8B H8BB . . 109.4 ?
C9B C8B H8BB . . 109.4 ?
H8BA C8B H8BB . . 108.0 ?
C8B C9B C4B . . 112.62(17) ?
C8B C9B H9BA . . 109.1 ?
C4B C9B H9BA . . 109.1 ?
C8B C9B H9BB . . 109.1 ?
C4B C9B H9BB . . 109.1 ?
H9BA C9B H9BB . . 107.8 ?
C1B C10B C4B . . 105.01(15) ?
C1B C10B H10A . . 110.7 ?
C4B C10B H10A . . 110.7 ?
C1B C10B H10B . . 110.7 ?
C4B C10B H10B . . 110.7 ?
H10A C10B H10B . . 108.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1A . 1.7158(19) ?
Cl2 C4A . 1.7196(18) ?
O1A C2A . 1.330(2) ?
O1A H1A . 0.8400 ?
O2A C3A . 1.227(2) ?
O3A C5A . 1.301(2) ?
O3A H3A . 0.8400 ?
O4A C6A . 1.215(2) ?
C1A C2A . 1.352(3) ?
C1A C6A . 1.465(3) ?
C2A C3A . 1.504(3) ?
C3A C4A . 1.441(3) ?
C4A C5A . 1.361(3) ?
C5A C6A . 1.517(3) ?
O1B C1B . 1.262(2) ?
C1B N2B . 1.318(2) ?
C1B C10B . 1.507(2) ?
N2B C3B . 1.460(2) ?
N2B H2BA . 0.8800 ?
C3B C4B . 1.558(2) ?
C3B H3BA . 0.9900 ?
C3B H3BB . 0.9900 ?
C4B C5B . 1.534(3) ?
C4B C9B . 1.538(3) ?
C4B C10B . 1.546(2) ?
C5B C6B . 1.530(3) ?
C5B H5BA . 0.9900 ?
C5B H5BB . 0.9900 ?
C6B C7B . 1.523(3) ?
C6B H6BA . 0.9900 ?
C6B H6BB . 0.9900 ?
C7B C8B . 1.525(3) ?
C7B H7BA . 0.9900 ?
C7B H7BB . 0.9900 ?
C8B C9B . 1.531(3) ?
C8B H8BA . 0.9900 ?
C8B H8BB . 0.9900 ?
C9B H9BA . 0.9900 ?
C9B H9BB . 0.9900 ?
C10B H10A . 0.9900 ?
C10B H10B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1A H1A O2A 2_556 0.84 1.97 2.7493(19) 153.1
O1A H1A O2A . 0.84 2.20 2.671(2) 115.2
O3A H3A O1B 2_676 0.84 1.70 2.4807(19) 153.4
O3A H3A O4A . 0.84 2.26 2.7148(19) 114.0
N2B H2BA O1B 2_676 0.88 2.07 2.913(2) 161.3
N2B H2BA O4A . 0.88 2.53 3.091(2) 122.2
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A C1A C2A O1A . . . . 179.69(16) ?
Cl1 C1A C2A O1A . . . . 0.0(3) ?
C6A C1A C2A C3A . . . . -1.6(3) ?
Cl1 C1A C2A C3A . . . . 178.76(13) ?
O1A C2A C3A O2A . . . . -0.8(3) ?
C1A C2A C3A O2A . . . . -179.58(18) ?
O1A C2A C3A C4A . . . . 179.11(16) ?
C1A C2A C3A C4A . . . . 0.3(3) ?
O2A C3A C4A C5A . . . . -179.95(18) ?
C2A C3A C4A C5A . . . . 0.2(3) ?
O2A C3A C4A Cl2 . . . . 0.0(3) ?
C2A C3A C4A Cl2 . . . . -179.94(13) ?
C3A C4A C5A O3A . . . . -179.05(16) ?
Cl2 C4A C5A O3A . . . . 1.1(3) ?
C3A C4A C5A C6A . . . . 0.6(3) ?
Cl2 C4A C5A C6A . . . . -179.28(13) ?
C2A C1A C6A O4A . . . . -176.63(18) ?
Cl1 C1A C6A O4A . . . . 3.0(3) ?
C2A C1A C6A C5A . . . . 2.3(3) ?
Cl1 C1A C6A C5A . . . . -178.02(13) ?
O3A C5A C6A O4A . . . . -3.2(3) ?
C4A C5A C6A O4A . . . . 177.16(17) ?
O3A C5A C6A C1A . . . . 177.86(15) ?
C4A C5A C6A C1A . . . . -1.8(3) ?
O1B C1B N2B C3B . . . . 174.06(18) ?
C10B C1B N2B C3B . . . . -5.0(2) ?
C1B N2B C3B C4B . . . . 14.0(2) ?
N2B C3B C4B C5B . . . . -136.89(16) ?
N2B C3B C4B C9B . . . . 101.19(17) ?
N2B C3B C4B C10B . . . . -16.48(19) ?
C9B C4B C5B C6B . . . . 55.7(2) ?
C10B C4B C5B C6B . . . . 177.77(17) ?
C3B C4B C5B C6B . . . . -66.9(2) ?
C4B C5B C6B C7B . . . . -57.1(2) ?
C5B C6B C7B C8B . . . . 55.9(2) ?
C6B C7B C8B C9B . . . . -54.4(3) ?
C7B C8B C9B C4B . . . . 54.4(2) ?
C5B C4B C9B C8B . . . . -54.5(2) ?
C10B C4B C9B C8B . . . . -177.91(16) ?
C3B C4B C9B C8B . . . . 68.3(2) ?
O1B C1B C10B C4B . . . . 174.58(18) ?
N2B C1B C10B C4B . . . . -6.4(2) ?
C5B C4B C10B C1B . . . . 133.80(17) ?
C9B C4B C10B C1B . . . . -104.25(17) ?
C3B C4B C10B C1B . . . . 13.99(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655978
