#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/85/4508549.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_4508549
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 H13 Br N2 O'
_chemical_formula_weight         317.18
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8120(2)
_cell_length_b                   9.5016(3)
_cell_length_c                   18.0400(7)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.4044
_cell_measurement_theta_min      3.3693
_cell_volume                     1339.05(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.928
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6015
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    3.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38091
_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            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       euhedral
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.017(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0376
_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)+(0.0299P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                2721
_reflns_number_total             3043
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg401341y_si_002.cif
_cod_data_source_block           cbzbr_check
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4508549
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
Br1 Br 1.16331(4) -0.08018(3) 0.79683(2) 0.02335(10) Uani 1 1 d .
O1 O 0.8432(3) -0.0438(2) 0.89406(13) 0.0189(5) Uani 1 1 d .
N1 N 0.6228(3) 0.1081(2) 0.89869(15) 0.0141(6) Uani 1 1 d .
N2 N 0.8463(4) 0.1455(3) 0.81670(16) 0.0186(6) Uani 1 1 d .
C1 C 0.7729(4) 0.0721(3) 0.86890(17) 0.0145(6) Uani 1 1 d .
C2 C 0.5390(4) 0.2371(3) 0.87670(18) 0.0157(7) Uani 1 1 d .
C3 C 0.4524(4) 0.2405(3) 0.81017(18) 0.0185(7) Uani 1 1 d .
H3 H 0.4462 0.1588 0.7799 0.022 Uiso 1 1 calc R
C4 C 0.3738(4) 0.3657(3) 0.7880(2) 0.0235(8) Uani 1 1 d .
H4 H 0.3115 0.3698 0.7428 0.028 Uiso 1 1 calc R
C5 C 0.3881(4) 0.4852(4) 0.8331(2) 0.0245(8) Uani 1 1 d .
H5 H 0.3380 0.5716 0.8179 0.029 Uiso 1 1 calc R
C6 C 0.4744(4) 0.4775(3) 0.8990(2) 0.0209(8) Uani 1 1 d .
H6 H 0.4838 0.5597 0.9287 0.025 Uiso 1 1 calc R
C7 C 0.5488(4) 0.3528(3) 0.92407(19) 0.0169(7) Uani 1 1 d .
C8 C 0.6241(4) 0.3455(3) 0.9980(2) 0.0183(7) Uani 1 1 d .
H8 H 0.6783 0.4286 1.0155 0.022 Uiso 1 1 calc R
C9 C 0.6254(4) 0.2349(3) 1.04390(19) 0.0183(7) Uani 1 1 d .
H9 H 0.6775 0.2494 1.0909 0.022 Uiso 1 1 calc R
C10 C 0.5557(4) 0.0934(4) 1.03028(18) 0.0181(7) Uani 1 1 d .
C11 C 0.5489(4) 0.0317(3) 0.96069(19) 0.0168(7) Uani 1 1 d .
C12 C 0.4714(4) -0.0975(3) 0.94784(19) 0.0193(7) Uani 1 1 d .
H12 H 0.4676 -0.1362 0.8993 0.023 Uiso 1 1 calc R
C13 C 0.4000(4) -0.1686(3) 1.0072(2) 0.0221(8) Uani 1 1 d .
H13 H 0.3447 -0.2564 0.9995 0.026 Uiso 1 1 calc R
C14 C 0.4091(4) -0.1118(3) 1.0780(2) 0.0236(8) Uani 1 1 d .
H14 H 0.3629 -0.1623 1.1188 0.028 Uiso 1 1 calc R
C15 C 0.4850(4) 0.0178(4) 1.0894(2) 0.0207(8) Uani 1 1 d .
H15 H 0.4893 0.0561 1.1381 0.025 Uiso 1 1 calc R
H1N H 0.946(5) 0.116(4) 0.796(2) 0.036(11) Uiso 1 1 d .
H2N H 0.801(5) 0.231(4) 0.803(2) 0.037(11) Uiso 1 1 d .
H1H H 0.954(5) -0.076(4) 0.870(2) 0.047(12) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1H 118(2)
C1 N1 C2 120.3(3)
C1 N1 C11 122.1(3)
C2 N1 C11 117.1(2)
C1 N2 H1N 120(2)
C1 N2 H2N 119(2)
H1N N2 H2N 120(3)
N2 C1 O1 121.0(3)
N2 C1 N1 122.6(3)
O1 C1 N1 116.3(3)
C3 C2 C7 122.9(3)
C3 C2 N1 118.8(3)
C7 C2 N1 118.4(3)
C2 C3 C4 119.0(3)
C2 C3 H3 120.5
C4 C3 H3 120.5
C3 C4 C5 119.3(3)
C3 C4 H4 120.4
C5 C4 H4 120.4
C6 C5 C4 120.0(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 122.1(3)
C5 C6 H6 118.9
C7 C6 H6 118.9
C2 C7 C6 116.6(3)
C2 C7 C8 123.0(3)
C6 C7 C8 120.3(3)
C9 C8 C7 127.3(3)
C9 C8 H8 116.4
C7 C8 H8 116.4
C8 C9 C10 127.7(3)
C8 C9 H9 116.1
C10 C9 H9 116.1
C11 C10 C15 117.3(3)
C11 C10 C9 123.5(3)
C15 C10 C9 119.2(3)
C10 C11 C12 122.8(3)
C10 C11 N1 118.1(3)
C12 C11 N1 119.1(3)
C13 C12 C11 118.6(3)
C13 C12 H12 120.7
C11 C12 H12 120.7
C12 C13 C14 120.1(3)
C12 C13 H13 119.9
C14 C13 H13 119.9
C15 C14 C13 120.3(3)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C10 120.8(3)
C14 C15 H15 119.6
C10 C15 H15 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.312(4)
O1 H1H 1.02(4)
N1 C1 1.335(4)
N1 C2 1.445(4)
N1 C11 1.453(4)
N2 C1 1.304(4)
N2 H1N 0.91(4)
N2 H2N 0.92(4)
C2 C3 1.378(4)
C2 C7 1.394(5)
C3 C4 1.398(4)
C3 H3 0.9500
C4 C5 1.401(5)
C4 H4 0.9500
C5 C6 1.369(5)
C5 H5 0.9500
C6 C7 1.395(4)
C6 H6 0.9500
C7 C8 1.459(5)
C8 C9 1.338(5)
C8 H8 0.9500
C9 C10 1.472(5)
C9 H9 0.9500
C10 C11 1.386(5)
C10 C15 1.400(5)
C11 C12 1.388(4)
C12 C13 1.384(5)
C12 H12 0.9500
C13 C14 1.389(5)
C13 H13 0.9500
C14 C15 1.382(5)
C14 H14 0.9500
C15 H15 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
C2 N1 C1 N2 -3.6(5)
C11 N1 C1 N2 -175.1(3)
C2 N1 C1 O1 177.5(3)
C11 N1 C1 O1 6.0(4)
C1 N1 C2 C3 78.1(4)
C11 N1 C2 C3 -110.0(3)
C1 N1 C2 C7 -102.2(3)
C11 N1 C2 C7 69.7(4)
C7 C2 C3 C4 1.5(5)
N1 C2 C3 C4 -178.8(3)
C2 C3 C4 C5 1.3(5)
C3 C4 C5 C6 -1.8(5)
C4 C5 C6 C7 -0.6(5)
C3 C2 C7 C6 -3.7(5)
N1 C2 C7 C6 176.6(3)
C3 C2 C7 C8 173.1(3)
N1 C2 C7 C8 -6.6(4)
C5 C6 C7 C2 3.3(5)
C5 C6 C7 C8 -173.7(3)
C2 C7 C8 C9 -31.4(5)
C6 C7 C8 C9 145.3(3)
C7 C8 C9 C10 1.8(5)
C8 C9 C10 C11 30.9(5)
C8 C9 C10 C15 -146.2(3)
C15 C10 C11 C12 2.0(5)
C9 C10 C11 C12 -175.1(3)
C15 C10 C11 N1 -179.5(3)
C9 C10 C11 N1 3.4(4)
C1 N1 C11 C10 104.7(3)
C2 N1 C11 C10 -67.0(4)
C1 N1 C11 C12 -76.7(4)
C2 N1 C11 C12 111.5(3)
C10 C11 C12 C13 -0.9(5)
N1 C11 C12 C13 -179.4(3)
C11 C12 C13 C14 -1.1(5)
C12 C13 C14 C15 1.9(5)
C13 C14 C15 C10 -0.7(5)
C11 C10 C15 C14 -1.2(5)
C9 C10 C15 C14 176.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146710
