#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:38:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179670 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/23/4512303.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_4512303
loop_
_publ_author_name
'Buist, Amanda R.'
'Kennedy, Alan R.'
_publ_section_title
;
 Ionic Cocrystals of Pharmaceutical Compounds: Sodium Complexes of
 Carbamazepine
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6508
_journal_paper_doi               10.1021/cg501400n
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C13 H10 Cl I2 N'
_chemical_formula_weight         469.47
_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                 122.427(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2879(4)
_cell_length_b                   17.9944(4)
_cell_length_c                   8.8718(3)
_cell_measurement_reflns_used    4022
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.5723
_cell_measurement_theta_min      3.5326
_cell_volume                     1386.30(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       '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  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5912
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         30.64
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    4.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0175
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0132P)²+2.1559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0384
_refine_ls_wR_factor_ref         0.0398
_reflns_number_gt                1778
_reflns_number_total             2000
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg501400n_si_002.cif
_cod_data_source_block           buist_ki_cbz_acetyl_cl
_cod_depositor_comments
'Adding full bibliography for 4512299--4512304.cif.'
_cod_original_cell_volume        1386.30(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4512303
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
I1 I 0.499934(16) -0.275062(8) -0.095210(18) 0.02006(5) Uani 1 1 d .
Cl1 Cl 0.5000 -0.26264(4) 0.2500 0.02115(15) Uani 1 2 d S
N1 N 0.5000 -0.09265(14) 0.2500 0.0176(5) Uani 1 2 d S
H1N H 0.5000 -0.1416 0.2500 0.021 Uiso 1 2 calc SR
C1 C 0.3937(2) -0.05746(12) 0.0986(3) 0.0177(4) Uani 1 1 d .
C2 C 0.2844(2) -0.09821(13) -0.0529(3) 0.0206(4) Uani 1 1 d .
H2 H 0.2826 -0.1509 -0.0492 0.025 Uiso 1 1 calc R
C3 C 0.1814(3) -0.06094(13) -0.2045(3) 0.0236(5) Uani 1 1 d .
H3 H 0.1076 -0.0882 -0.3069 0.028 Uiso 1 1 calc R
C4 C 0.1822(3) 0.01801(13) -0.2127(3) 0.0236(5) Uani 1 1 d .
H4 H 0.1104 0.0427 -0.3208 0.028 Uiso 1 1 calc R
C5 C 0.2845(2) 0.05826(12) -0.0674(3) 0.0207(4) Uani 1 1 d .
H5 H 0.2830 0.1110 -0.0738 0.025 Uiso 1 1 calc R
C6 C 0.3942(2) 0.02184(12) 0.0946(3) 0.0184(4) Uani 1 1 d .
C7 C 0.5000 0.05934(16) 0.2500 0.0187(6) Uani 1 2 d S
H7 H 0.5000 0.1121 0.2500 0.022 Uiso 1 2 calc SR
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02901(8) 0.01445(8) 0.02149(7) 0.00082(5) 0.01671(6) 0.00042(6)
Cl1 0.0306(4) 0.0127(3) 0.0215(3) 0.000 0.0148(3) 0.000
N1 0.0228(12) 0.0093(12) 0.0275(13) 0.000 0.0181(11) 0.000
C1 0.0208(10) 0.0145(10) 0.0264(10) 0.0008(8) 0.0185(9) 0.0012(8)
C2 0.0241(10) 0.0148(10) 0.0293(11) -0.0033(9) 0.0186(9) -0.0018(8)
C3 0.0233(11) 0.0228(12) 0.0282(11) -0.0040(9) 0.0160(9) -0.0018(9)
C4 0.0232(10) 0.0221(12) 0.0290(11) 0.0052(9) 0.0163(9) 0.0036(9)
C5 0.0238(10) 0.0149(10) 0.0297(11) 0.0030(9) 0.0184(9) 0.0033(8)
C6 0.0219(10) 0.0129(10) 0.0286(10) 0.0010(8) 0.0190(9) 0.0015(8)
C7 0.0257(15) 0.0095(13) 0.0295(15) 0.000 0.0205(13) 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 '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'
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C1 124.1(3) 2_655 .
C1 N1 H1N 118.0 2_655 .
C1 N1 H1N 118.0 . .
N1 C1 C2 120.7(2) . .
N1 C1 C6 118.8(2) . .
C2 C1 C6 120.5(2) . .
C3 C2 C1 119.1(2) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 C4 121.3(2) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C5 C4 C3 120.5(2) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 120.3(2) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C7 C6 C5 123.6(2) . .
C7 C6 C1 118.2(2) . .
C5 C6 C1 118.3(2) . .
C6 C7 C6 121.9(3) . 2_655
C6 C7 H7 119.1 . .
C6 C7 H7 119.1 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 I1 2.7473(3) 2_654
N1 C1 1.351(2) 2_655
N1 C1 1.351(2) .
N1 H1N 0.8800 .
C1 C2 1.410(3) .
C1 C6 1.427(3) .
C2 C3 1.362(3) .
C2 H2 0.9500 .
C3 C4 1.423(3) .
C3 H3 0.9500 .
C4 C5 1.356(3) .
C4 H4 0.9500 .
C5 C6 1.425(3) .
C5 H5 0.9500 .
C6 C7 1.390(3) .
C7 C6 1.390(3) 2_655
C7 H7 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 N1 C1 C2 -178.6(2) 2_655 .
C1 N1 C1 C6 1.44(12) 2_655 .
N1 C1 C2 C3 -178.42(17) . .
C6 C1 C2 C3 1.5(3) . .
C1 C2 C3 C4 0.0(3) . .
C2 C3 C4 C5 -1.2(3) . .
C3 C4 C5 C6 0.9(3) . .
C4 C5 C6 C7 -178.40(17) . .
C4 C5 C6 C1 0.5(3) . .
N1 C1 C6 C7 -2.8(2) . .
C2 C1 C6 C7 177.20(15) . .
N1 C1 C6 C5 178.17(15) . .
C2 C1 C6 C5 -1.8(3) . .
C5 C6 C7 C6 -179.7(2) . 2_655
C1 C6 C7 C6 1.41(12) . 2_655
