#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:35:18 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179537 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/06/4500600.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_4500600
loop_
_publ_author_name
'André, Vânia'
'Fernandes, Auguste'
'Santos, Pedro Paulo'
'Duarte, M. Teresa'
_publ_section_title
;
 On the Track of New Multicomponent Gabapentin Crystal Forms: Synthon
 Competition and pH Stability
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2325
_journal_paper_doi               10.1021/cg200008z
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C9 H18 N O2, 0.5(C8 H4 O4)'
_chemical_formula_sum            'C13 H20 N O4'
_chemical_formula_weight         254.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 101.140(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.324(17)
_cell_length_b                   6.433(3)
_cell_length_c                   14.561(8)
_cell_measurement_reflns_used    2881
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      3.26
_cell_volume                     2511(2)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_collection       'BRUKER APEX2 (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II 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     0.71069
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10134
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0455
_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)+(0.0461P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                1448
_reflns_number_total             2281
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg200008z_si_001.cif
_cod_data_source_block           gbpterephtac
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4500600
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
H2 H 0.1584(9) 0.529(4) 0.5862(16) 0.029(7) Uiso 1 1 d .
H3 H 0.1601(10) 0.763(4) 0.5720(16) 0.032(7) Uiso 1 1 d .
H1 H 0.2051(10) 0.631(4) 0.5617(17) 0.036(8) Uiso 1 1 d .
C12 C 0.03938(8) -0.1324(3) 0.49363(14) 0.0166(5) Uani 1 1 d .
H12 H 0.0656 -0.2220 0.4895 0.020 Uiso 1 1 calc R
C13 C -0.00912(9) -0.2054(3) 0.47612(15) 0.0155(5) Uani 1 1 d .
H13 H -0.0152 -0.3441 0.4598 0.019 Uiso 1 1 calc R
C7 C 0.19159(8) 0.7279(3) 0.86120(14) 0.0162(5) Uani 1 1 d .
H7A H 0.1981 0.8744 0.8535 0.019 Uiso 1 1 calc R
H7B H 0.1684 0.7169 0.9038 0.019 Uiso 1 1 calc R
C11 C 0.04907(8) 0.0758(3) 0.51757(14) 0.0135(5) Uani 1 1 d .
C9 C 0.23987(8) 0.6226(3) 0.90526(14) 0.0139(5) Uani 1 1 d .
C10 C 0.10109(9) 0.1626(3) 0.53632(14) 0.0145(5) Uani 1 1 d .
C8 C 0.20253(8) 0.6705(3) 0.69662(14) 0.0147(5) Uani 1 1 d .
H8A H 0.2164 0.8095 0.7059 0.018 Uiso 1 1 calc R
H8B H 0.2299 0.5728 0.7124 0.018 Uiso 1 1 calc R
C6 C 0.11725(8) 0.7557(4) 0.72983(15) 0.0202(6) Uani 1 1 d .
H6A H 0.1244 0.9035 0.7310 0.024 Uiso 1 1 calc R
H6B H 0.1043 0.7170 0.6653 0.024 Uiso 1 1 calc R
C2 C 0.15462(9) 0.4038(3) 0.77327(15) 0.0193(6) Uani 1 1 d .
H2A H 0.1433 0.3466 0.7112 0.023 Uiso 1 1 calc R
H2B H 0.1850 0.3318 0.8014 0.023 Uiso 1 1 calc R
C1 C 0.16625(8) 0.6371(3) 0.76449(14) 0.0151(5) Uani 1 1 d .
C5 C 0.07719(10) 0.7154(4) 0.78719(17) 0.0320(7) Uani 1 1 d .
H5A H 0.0466 0.7847 0.7581 0.038 Uiso 1 1 calc R
H5B H 0.0878 0.7725 0.8495 0.038 Uiso 1 1 calc R
C3 C 0.11499(10) 0.3637(4) 0.83211(17) 0.0282(6) Uani 1 1 d .
H3A H 0.1076 0.2162 0.8319 0.034 Uiso 1 1 calc R
H3B H 0.1277 0.4055 0.8963 0.034 Uiso 1 1 calc R
C4 C 0.06746(10) 0.4834(5) 0.79421(18) 0.0396(8) Uani 1 1 d .
H4A H 0.0437 0.4615 0.8350 0.048 Uiso 1 1 calc R
H4B H 0.0528 0.4304 0.7327 0.048 Uiso 1 1 calc R
O3 O 0.13782(6) 0.0354(2) 0.54611(10) 0.0186(4) Uani 1 1 d .
O2 O 0.27969(6) 0.7042(2) 0.88094(11) 0.0197(4) Uani 1 1 d .
H5 H 0.3046 0.6398 0.9063 0.030 Uiso 1 1 calc R
O4 O 0.10605(6) 0.3562(2) 0.54161(10) 0.0193(4) Uani 1 1 d .
O1 O 0.24187(6) 0.4732(2) 0.95775(11) 0.0237(4) Uani 1 1 d .
N1 N 0.17944(8) 0.6445(3) 0.59543(12) 0.0145(5) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_1
_geom_angle_site_symmetry_3
C13 C12 C11 120.1(2) . .
C12 C13 C11 121.4(2) . 5_556
C9 C7 C1 114.52(18) . .
C13 C11 C12 118.6(2) 5_556 .
C13 C11 C10 119.47(19) 5_556 .
C12 C11 C10 122.0(2) . .
O1 C9 O2 122.8(2) . .
O1 C9 C7 123.2(2) . .
O2 C9 C7 113.98(19) . .
O4 C10 O3 123.7(2) . .
O4 C10 C11 117.9(2) . .
O3 C10 C11 118.42(19) . .
N1 C8 C1 114.45(18) . .
C5 C6 C1 114.05(19) . .
C3 C2 C1 112.94(19) . .
C6 C1 C8 110.27(17) . .
C6 C1 C2 109.23(19) . .
C8 C1 C2 110.85(17) . .
C6 C1 C7 108.49(17) . .
C8 C1 C7 107.34(18) . .
C2 C1 C7 110.62(17) . .
C6 C5 C4 110.9(2) . .
C4 C3 C2 111.1(2) . .
C3 C4 C5 111.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C12 C13 1.383(3) .
C12 C11 1.396(3) .
C13 C11 1.391(3) 5_556
C7 C9 1.511(3) .
C7 C1 1.558(3) .
C11 C13 1.391(3) 5_556
C11 C10 1.502(3) .
C9 O1 1.223(3) .
C9 O2 1.317(3) .
C10 O4 1.254(3) .
C10 O3 1.281(3) .
C8 N1 1.496(3) .
C8 C1 1.544(3) .
C6 C5 1.522(3) .
C6 C1 1.539(3) .
C2 C3 1.527(3) .
C2 C1 1.545(3) .
C5 C4 1.522(4) .
C3 C4 1.519(4) .
