#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/85/4508546.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_4508546
loop_
_publ_author_name
'Buist, Amanda R.'
'Kennedy, Alan R.'
'Shankland, Kenneth'
'Shankland, Norman'
'Spillman, Mark J.'
_publ_section_title
;
 Salt Forms of Amides: Protonation and Polymorphism of Carbamazepine and
 Cytenamide
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5121
_journal_paper_doi               10.1021/cg401341y
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C15 H15.5 Cl0.5 N2 O2.5'
_chemical_formula_weight         281.52
_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                 119.462(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.4803(17)
_cell_length_b                   4.9462(2)
_cell_length_c                   21.6558(13)
_cell_measurement_reflns_used    3716
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.9005
_cell_measurement_theta_min      5.0286
_cell_volume                     2749.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10286
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         71.92
_diffrn_reflns_theta_min         6.14
_exptl_absorpt_coefficient_mu    1.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flattened prism'
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0368
_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)+(0.0561P)²+1.5551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                2274
_reflns_number_total             2686
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg401341y_si_002.cif
_cod_data_source_block           cbz_greenmonop
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C15 H15.50 Cl0.50 N2 O2.50'
_cod_database_code               4508546
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
O1 O 0.05386(4) 0.1788(2) -0.00192(5) 0.0276(2) Uani 1 1 d .
N1 N 0.10452(4) 0.4124(2) 0.10010(6) 0.0238(3) Uani 1 1 d .
N2 N 0.02527(5) 0.2277(3) 0.07646(7) 0.0275(3) Uani 1 1 d .
H1N H -0.0006(7) 0.122(4) 0.0506(10) 0.033 Uiso 1 1 d .
H2N H 0.0292(7) 0.285(4) 0.1151(11) 0.033 Uiso 1 1 d .
C1 C 0.06047(5) 0.2687(3) 0.05587(7) 0.0227(3) Uani 1 1 d .
C2 C 0.11746(5) 0.4725(3) 0.17186(7) 0.0238(3) Uani 1 1 d .
C3 C 0.09016(6) 0.6738(3) 0.18462(8) 0.0282(3) Uani 1 1 d .
H3 H 0.0651 0.7795 0.1464 0.034 Uiso 1 1 calc R
C4 C 0.09945(6) 0.7204(3) 0.25303(9) 0.0315(4) Uani 1 1 d .
H4 H 0.0808 0.8578 0.2618 0.038 Uiso 1 1 calc R
C5 C 0.13607(6) 0.5656(4) 0.30853(8) 0.0333(4) Uani 1 1 d .
H5 H 0.1423 0.5953 0.3554 0.040 Uiso 1 1 calc R
C6 C 0.16356(6) 0.3682(3) 0.29581(8) 0.0303(3) Uani 1 1 d .
H6 H 0.1885 0.2637 0.3344 0.036 Uiso 1 1 calc R
C7 C 0.15556(5) 0.3179(3) 0.22733(8) 0.0252(3) Uani 1 1 d .
C8 C 0.18656(5) 0.1104(3) 0.21706(8) 0.0277(3) Uani 1 1 d .
H8 H 0.1983 -0.0348 0.2500 0.033 Uiso 1 1 calc R
C9 C 0.20051(5) 0.1001(3) 0.16661(8) 0.0275(3) Uani 1 1 d .
H9 H 0.2207 -0.0519 0.1681 0.033 Uiso 1 1 calc R
C10 C 0.18835(5) 0.2941(3) 0.10980(8) 0.0244(3) Uani 1 1 d .
C11 C 0.14337(5) 0.4536(3) 0.07930(7) 0.0236(3) Uani 1 1 d .
C12 C 0.13472(6) 0.6453(3) 0.02793(8) 0.0290(3) Uani 1 1 d .
H12 H 0.1045 0.7560 0.0094 0.035 Uiso 1 1 calc R
C13 C 0.16999(6) 0.6757(3) 0.00356(9) 0.0320(4) Uani 1 1 d .
H13 H 0.1641 0.8069 -0.0317 0.038 Uiso 1 1 calc R
C14 C 0.21399(6) 0.5132(3) 0.03105(8) 0.0312(3) Uani 1 1 d .
H14 H 0.2379 0.5300 0.0138 0.037 Uiso 1 1 calc R
C15 C 0.22306(6) 0.3267(3) 0.08346(8) 0.0291(3) Uani 1 1 d .
H15 H 0.2535 0.2179 0.1021 0.035 Uiso 1 1 calc R
Cl1 Cl -0.02683(7) 0.2514(4) 0.17716(11) 0.0307(3) Uani 0.50 1 d P
O2W O -0.07272(16) -0.1636(7) 0.1119(2) 0.0388(8) Uani 0.50 1 d PD
H3W H -0.0743(15) -0.315(4) 0.1321(16) 0.047 Uiso 0.50 1 d PD
H4W H -0.0685(8) -0.238(4) 0.0775(8) 0.047 Uiso 1 1 d D
H5W H -0.0400(6) -0.129(7) 0.1421(13) 0.047 Uiso 0.50 1 d PD
O1W O -0.0261(3) 0.2912(15) 0.1648(4) 0.071(3) Uani 0.50 1 d PD
H1W H -0.012(2) 0.273(10) 0.2112(7) 0.085 Uiso 0.50 1 d PD
H2W H -0.044(2) 0.141(7) 0.151(2) 0.085 Uiso 0.50 1 d PD
O3W O -0.06968(15) -0.2870(7) 0.1079(2) 0.0355(7) Uani 0.50 1 d PD
H6W H -0.0484(14) -0.419(6) 0.1322(19) 0.050 Uiso 0.50 1 d PD
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C11 118.76(11)
C1 N1 C2 121.22(11)
C11 N1 C2 118.75(11)
C1 N2 H1N 117.3(12)
C1 N2 H2N 122.4(13)
H1N N2 H2N 119.9(17)
O1 C1 N2 121.19(13)
O1 C1 N1 120.72(12)
N2 C1 N1 118.09(13)
C3 C2 C7 121.25(14)
C3 C2 N1 119.42(13)
C7 C2 N1 119.26(13)
C4 C3 C2 120.12(15)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 119.65(15)
C5 C4 H4 120.2
C3 C4 H4 120.2
C6 C5 C4 120.09(14)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 121.72(15)
C5 C6 H6 119.1
C7 C6 H6 119.1
C2 C7 C6 117.14(14)
C2 C7 C8 123.39(13)
C6 C7 C8 119.48(14)
C9 C8 C7 127.88(14)
C9 C8 H8 116.1
C7 C8 H8 116.1
C8 C9 C10 127.87(14)
C8 C9 H9 116.1
C10 C9 H9 116.1
C11 C10 C15 117.03(14)
C11 C10 C9 123.50(13)
C15 C10 C9 119.47(13)
C12 C11 C10 121.48(13)
C12 C11 N1 119.24(12)
C10 C11 N1 119.26(13)
C11 C12 C13 120.23(14)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C14 119.46(15)
C12 C13 H13 120.3
C14 C13 H13 120.3
C15 C14 C13 120.09(14)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C10 121.64(14)
C14 C15 H15 119.2
C10 C15 H15 119.2
H1W Cl1 H2W 141(3)
O3W O2W H3W 45(2)
O3W O2W H4W 53.1(13)
H3W O2W H4W 97(2)
O3W O2W H5W 97(3)
H3W O2W H5W 96(2)
H4W O2W H5W 98.7(19)
O3W O2W H6W 24.4(18)
H3W O2W H6W 39(3)
H4W O2W H6W 68.5(15)
H5W O2W H6W 75(3)
H1W O1W H2W 100(2)
O2W O3W H3W 90(2)
O2W O3W H4W 82.5(13)
H3W O3W H4W 169(4)
O2W O3W H5W 50.1(17)
H3W O3W H5W 92(3)
H4W O3W H5W 90(2)
O2W O3W H6W 138(3)
H3W O3W H6W 73(4)
H4W O3W H6W 117(2)
H5W O3W H6W 92(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2498(17)
N1 C1 1.3730(18)
N1 C11 1.4366(17)
N1 C2 1.4374(17)
N2 C1 1.3311(19)
N2 H1N 0.87(2)
N2 H2N 0.84(2)
C2 C3 1.391(2)
C2 C7 1.401(2)
C3 C4 1.387(2)
C3 H3 0.9500
C4 C5 1.386(2)
C4 H4 0.9500
C5 C6 1.380(2)
C5 H5 0.9500
C6 C7 1.405(2)
C6 H6 0.9500
C7 C8 1.462(2)
C8 C9 1.344(2)
C8 H8 0.9500
C9 C10 1.459(2)
C9 H9 0.9500
C10 C11 1.398(2)
C10 C15 1.404(2)
C11 C12 1.386(2)
C12 C13 1.386(2)
C12 H12 0.9500
C13 C14 1.387(2)
C13 H13 0.9500
C14 C15 1.383(2)
C14 H14 0.9500
C15 H15 0.9500
Cl1 H1W 0.658(19)
Cl1 H2W 0.77(2)
O2W O3W 0.629(3)
O2W H3W 0.882(10)
O2W H4W 0.890(9)
O2W H5W 0.877(10)
O1W H1W 0.882(10)
O1W H2W 0.878(10)
O3W H3W 0.62(2)
O3W H4W 0.718(15)
O3W H5W 1.14(2)
O3W H6W 0.877(10)
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
C11 N1 C1 O1 -1.1(2)
C2 N1 C1 O1 -168.06(13)
C11 N1 C1 N2 178.76(13)
C2 N1 C1 N2 11.8(2)
C1 N1 C2 C3 -75.51(18)
C11 N1 C2 C3 117.51(14)
C1 N1 C2 C7 101.34(15)
C11 N1 C2 C7 -65.65(17)
C7 C2 C3 C4 -1.6(2)
N1 C2 C3 C4 175.14(13)
C2 C3 C4 C5 0.0(2)
C3 C4 C5 C6 0.8(2)
C4 C5 C6 C7 0.0(2)
C3 C2 C7 C6 2.3(2)
N1 C2 C7 C6 -174.47(12)
C3 C2 C7 C8 -177.85(13)
N1 C2 C7 C8 5.4(2)
C5 C6 C7 C2 -1.5(2)
C5 C6 C7 C8 178.66(14)
C2 C7 C8 C9 28.8(2)
C6 C7 C8 C9 -151.35(15)
C7 C8 C9 C10 0.3(3)
C8 C9 C10 C11 -29.3(2)
C8 C9 C10 C15 150.62(16)
C15 C10 C11 C12 -3.2(2)
C9 C10 C11 C12 176.65(14)
C15 C10 C11 N1 174.85(13)
C9 C10 C11 N1 -5.3(2)
C1 N1 C11 C12 76.51(17)
C2 N1 C11 C12 -116.18(15)
C1 N1 C11 C10 -101.61(16)
C2 N1 C11 C10 65.70(18)
C10 C11 C12 C13 2.5(2)
N1 C11 C12 C13 -175.61(13)
C11 C12 C13 C14 -0.1(2)
C12 C13 C14 C15 -1.4(2)
C13 C14 C15 C10 0.6(2)
C11 C10 C15 C14 1.7(2)
C9 C10 C15 C14 -178.18(14)
