#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/00/4500003.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_4500003
loop_
_publ_author_name
'Scott G. Fleischman'
'Srinivasan S. Kuduva'
'Jennifer A. McMahon'
'Brian Moulton'
'Rosa D. Bailey Walsh'
'Naír Rodríguez-Hornedo'
'Michael J. Zaworotko'
_publ_section_title
;
 Crystal Engineering of the Composition of Pharmaceutical Phases:
 Multiple-Component Crystalline Solids Involving Carbamazepine
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              909
_journal_page_last               919
_journal_paper_doi               10.1021/cg034035x
_journal_volume                  3
_journal_year                    2003
_chemical_formula_sum            'C18 H18 N2 O2'
_chemical_formula_weight         294.34
_space_group_IT_number           2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.809(3)
_cell_angle_beta                 93.401(4)
_cell_angle_gamma                101.362(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3985(15)
_cell_length_b                   8.9054(18)
_cell_length_c                   11.873(2)
_cell_measurement_temperature    100(2)
_cell_volume                     760.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3283
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9750
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.017(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.665
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.665
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0768
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2089
_refine_ls_wR_factor_ref         0.2669
_reflns_number_gt                1824
_reflns_number_total             2449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm431.cif
_cod_data_source_block           jm431
_cod_database_code               4500003
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0407(3) 0.1193(3) 0.3890(2) 0.0265(7) Uani 1 1 d . . .
N1 N 0.8308(3) 0.0601(3) 0.2349(3) 0.0237(8) Uani 1 1 d . . .
N2 N 0.8327(3) -0.1076(3) 0.3743(3) 0.0277(8) Uani 1 1 d . . .
H2A H 0.8796 -0.1349 0.4372 0.033 Uiso 1 1 calc R . .
H2B H 0.7371 -0.1690 0.3350 0.033 Uiso 1 1 calc R . .
C1 C 0.8785(4) 0.2176(4) 0.2085(3) 0.0231(9) Uani 1 1 d . . .
C14 C 0.6704(4) -0.0352(4) 0.1748(3) 0.0214(9) Uani 1 1 d . . .
C9 C 0.4934(4) -0.0051(4) 0.1885(3) 0.0249(9) Uani 1 1 d . . .
C10 C 0.3407(4) -0.1057(4) 0.1299(3) 0.0265(9) Uani 1 1 d . . .
H10 H 0.2201 -0.0883 0.1411 0.032 Uiso 1 1 calc R . .
C13 C 0.6908(4) -0.1617(4) 0.0989(3) 0.0269(9) Uani 1 1 d . . .
H13 H 0.8106 -0.1813 0.0882 0.032 Uiso 1 1 calc R . .
C7 C 0.5788(4) 0.2698(4) 0.2791(3) 0.0254(9) Uani 1 1 d . . .
H7 H 0.5378 0.3466 0.3267 0.031 Uiso 1 1 calc R . .
C15 C 0.9076(4) 0.0286(4) 0.3383(3) 0.0215(8) Uani 1 1 d . . .
C8 C 0.4657(4) 0.1311(4) 0.2616(3) 0.0238(9) Uani 1 1 d . . .
H8 H 0.3559 0.1191 0.3004 0.029 Uiso 1 1 calc R . .
C2 C 1.0426(4) 0.2668(4) 0.1597(3) 0.0270(9) Uani 1 1 d . . .
H2 H 1.1199 0.1960 0.1407 0.032 Uiso 1 1 calc R . .
C5 C 0.8144(4) 0.4717(4) 0.2124(3) 0.0279(9) Uani 1 1 d . . .
H5 H 0.7376 0.5430 0.2309 0.033 Uiso 1 1 calc R . .
C12 C 0.5381(4) -0.2571(4) 0.0402(3) 0.0268(9) Uani 1 1 d . . .
H12 H 0.5531 -0.3419 -0.0112 0.032 Uiso 1 1 calc R . .
C11 C 0.3613(4) -0.2300(4) 0.0557(3) 0.0264(9) Uani 1 1 d . . .
H11 H 0.2560 -0.2965 0.0156 0.032 Uiso 1 1 calc R . .
C3 C 1.0936(4) 0.4186(4) 0.1388(3) 0.0303(10) Uani 1 1 d . . .
H3 H 1.2067 0.4525 0.1062 0.036 Uiso 1 1 calc R . .
C4 C 0.9802(4) 0.5213(4) 0.1651(3) 0.0273(9) Uani 1 1 d . . .
H4 H 1.0156 0.6257 0.1509 0.033 Uiso 1 1 calc R . .
C6 C 0.7591(4) 0.3178(4) 0.2333(3) 0.0251(9) Uani 1 1 d . . .
O2 O 0.5080(3) 0.3620(3) 0.6474(2) 0.0364(8) Uani 1 1 d . . .
C17 C 0.6498(4) 0.3588(5) 0.6012(3) 0.0310(10) Uani 1 1 d . . .
C18 C 0.7655(5) 0.5014(5) 0.5648(4) 0.0407(11) Uani 1 1 d . . .
H18A H 0.7113 0.5906 0.5876 0.061 Uiso 1 1 calc R . .
H18B H 0.7692 0.4889 0.4820 0.061 Uiso 1 1 calc R . .
H18C H 0.8914 0.5176 0.6010 0.061 Uiso 1 1 calc R . .
C16 C 0.7151(6) 0.2119(6) 0.5767(4) 0.0473(12) Uani 1 1 d . . .
H16A H 0.8224 0.2117 0.6291 0.071 Uiso 1 1 calc R . .
H16B H 0.7502 0.2025 0.4983 0.071 Uiso 1 1 calc R . .
H16C H 0.6156 0.1247 0.5864 0.071 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C14 123.1(2) . . ?
C15 N1 C1 116.8(3) . . ?
C14 N1 C1 116.9(2) . . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 N1 119.4(3) . . ?
C6 C1 N1 119.4(3) . . ?
C9 C14 C13 119.5(3) . . ?
C9 C14 N1 121.6(3) . . ?
C13 C14 N1 118.9(3) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 C8 119.5(3) . . ?
C14 C9 C8 121.6(3) . . ?
C11 C10 C9 121.3(3) . . ?
C12 C13 C14 120.4(3) . . ?
C8 C7 C6 127.8(3) . . ?
O1 C15 N2 123.3(3) . . ?
O1 C15 N1 120.1(3) . . ?
N2 C15 N1 116.5(3) . . ?
C7 C8 C9 126.8(3) . . ?
C3 C2 C1 120.0(3) . . ?
C4 C5 C6 120.8(3) . . ?
C13 C12 C11 120.4(4) . . ?
C10 C11 C12 119.5(3) . . ?
C2 C3 C4 120.1(3) . . ?
C3 C4 C5 120.0(3) . . ?
C1 C6 C5 117.9(3) . . ?
C1 C6 C7 123.4(3) . . ?
C5 C6 C7 118.7(3) . . ?
O2 C17 C16 121.2(3) . . ?
O2 C17 C18 121.8(3) . . ?
C16 C17 C18 117.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.225(4) . ?
N1 C15 1.399(4) . ?
N1 C14 1.421(4) . ?
N1 C1 1.448(4) . ?
N2 C15 1.353(4) . ?
C1 C2 1.388(4) . ?
C1 C6 1.397(5) . ?
C14 C9 1.403(4) . ?
C14 C13 1.407(5) . ?
C9 C10 1.395(5) . ?
C9 C8 1.474(5) . ?
C10 C11 1.382(6) . ?
C13 C12 1.376(5) . ?
C7 C8 1.338(5) . ?
C7 C6 1.473(4) . ?
C2 C3 1.382(5) . ?
C5 C4 1.391(4) . ?
C5 C6 1.402(5) . ?
C12 C11 1.395(5) . ?
C3 C4 1.384(5) . ?
O2 C17 1.216(4) . ?
C17 C16 1.489(6) . ?
C17 C18 1.503(5) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C1 C2 83.7(4) . . . . ?
C14 N1 C1 C2 -115.6(3) . . . . ?
C15 N1 C1 C6 -95.9(3) . . . . ?
C14 N1 C1 C6 64.8(5) . . . . ?
C15 N1 C14 C9 94.0(4) . . . . ?
C1 N1 C14 C9 -65.3(4) . . . . ?
C15 N1 C14 C13 -86.6(4) . . . . ?
C1 N1 C14 C13 114.0(3) . . . . ?
C13 C14 C9 C10 2.6(4) . . . . ?
N1 C14 C9 C10 -178.0(3) . . . . ?
C13 C14 C9 C8 -176.3(3) . . . . ?
N1 C14 C9 C8 3.1(4) . . . . ?
C14 C9 C10 C11 -2.5(5) . . . . ?
C8 C9 C10 C11 176.4(3) . . . . ?
C9 C14 C13 C12 -1.3(4) . . . . ?
N1 C14 C13 C12 179.4(3) . . . . ?
C14 N1 C15 O1 -176.3(3) . . . . ?
C1 N1 C15 O1 -17.0(4) . . . . ?
C14 N1 C15 N2 6.6(5) . . . . ?
C1 N1 C15 N2 165.9(3) . . . . ?
C6 C7 C8 C9 -2.3(5) . . . . ?
C10 C9 C8 C7 -145.3(3) . . . . ?
C14 C9 C8 C7 33.6(5) . . . . ?
C6 C1 C2 C3 2.5(5) . . . . ?
N1 C1 C2 C3 -177.1(3) . . . . ?
C14 C13 C12 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C13 C12 C11 C10 0.6(5) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C6 C5 C4 C3 -0.5(5) . . . . ?
C2 C1 C6 C5 -3.1(5) . . . . ?
N1 C1 C6 C5 176.5(3) . . . . ?
C2 C1 C6 C7 176.5(3) . . . . ?
N1 C1 C6 C7 -3.9(5) . . . . ?
C4 C5 C6 C1 2.1(5) . . . . ?
C4 C5 C6 C7 -177.5(3) . . . . ?
C8 C7 C6 C1 -30.4(5) . . . . ?
C8 C7 C6 C5 149.1(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661265
2 PubChem 139144268
