#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/85/2018512.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018512
loop_
_publ_author_name
'Popp, Sebastian'
'Ruth, Kai'
'Lerner, Hans-Wolfram'
'Bolte, Michael'
_publ_section_title
;
 Structural characteristics of dibromoborylated benzene derivatives
;
_journal_coeditor_code           SK3438
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o226
_journal_page_last               o230
_journal_paper_doi               10.1107/S0108270112020604
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H12 B Br2 N'
_chemical_formula_moiety         'C8 H12 B Br2 N'
_chemical_formula_sum            'C8 H12 B Br2 N'
_chemical_formula_weight         292.82
_chemical_name_systematic
;
dibromo(dimethylamino)(phenyl)borane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.249(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9095(9)
_cell_length_b                   9.2874(13)
_cell_length_c                   12.9306(13)
_cell_measurement_reflns_used    4532
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.5
_cell_volume                     1069.1(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_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  0.0817
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6363
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.59
_diffrn_reflns_theta_min         3.50
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.530
_exptl_absorpt_correction_T_max  0.7046
_exptl_absorpt_correction_T_min  0.3288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.961
_refine_ls_extinction_coef       0.0035(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0462
_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)+(0.0472P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                1413
_reflns_number_total             2004
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3438.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018512
_cod_database_fobs_code          2018512
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
B B1 0.1562(8) 0.1816(7) 0.4299(4) 0.0238(15) Uani d . 1 1
Br Br1 0.19350(9) -0.00845(7) 0.35462(4) 0.0406(2) Uani d . 1 1
Br Br2 -0.06537(8) 0.23148(8) 0.39628(5) 0.0402(2) Uani d . 1 1
N N1 0.1676(6) 0.1454(6) 0.5521(3) 0.0257(11) Uani d . 1 1
H H1 0.102(8) 0.080(8) 0.563(5) 0.031 Uiso d . 1 1
C C1 0.3197(8) 0.0914(8) 0.5886(4) 0.0388(17) Uani d . 1 1
H H1A 0.3478 0.0087 0.5464 0.058 Uiso calc R 1 1
H H1B 0.3164 0.0621 0.6612 0.058 Uiso calc R 1 1
H H1C 0.3941 0.1683 0.5818 0.058 Uiso calc R 1 1
C C2 0.1254(9) 0.2710(8) 0.6194(4) 0.0364(16) Uani d . 1 1
H H2A 0.0255 0.3062 0.5973 0.055 Uiso calc R 1 1
H H2B 0.1991 0.3485 0.6127 0.055 Uiso calc R 1 1
H H2C 0.1242 0.2398 0.6917 0.055 Uiso calc R 1 1
C C11 0.2681(7) 0.3076(6) 0.3985(3) 0.0236(13) Uani d . 1 1
C C12 0.4201(7) 0.2776(7) 0.3746(4) 0.0298(14) Uani d . 1 1
H H12 0.4544 0.1807 0.3756 0.036 Uiso calc R 1 1
C C13 0.5186(9) 0.3861(8) 0.3500(5) 0.0404(18) Uani d . 1 1
H H13 0.6194 0.3637 0.3346 0.049 Uiso calc R 1 1
C C14 0.4701(9) 0.5266(8) 0.3479(4) 0.0408(19) Uani d . 1 1
H H14 0.5373 0.6010 0.3297 0.049 Uiso calc R 1 1
C C15 0.3260(10) 0.5606(8) 0.3719(5) 0.0447(19) Uani d . 1 1
H H15 0.2945 0.6583 0.3716 0.054 Uiso calc R 1 1
C C16 0.2252(8) 0.4517(7) 0.3967(4) 0.0326(15) Uani d . 1 1
H H16 0.1253 0.4766 0.4128 0.039 Uiso calc R 1 1
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 B1 N1 112.6(5)
C11 B1 Br1 113.3(4)
N1 B1 Br1 106.3(4)
C11 B1 Br2 112.6(4)
N1 B1 Br2 106.1(4)
Br1 B1 Br2 105.4(3)
C1 N1 C2 108.6(5)
C1 N1 B1 113.4(5)
C2 N1 B1 113.2(5)
C1 N1 H1 109(5)
C2 N1 H1 105(4)
B1 N1 H1 107(4)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C16 C11 C12 116.5(6)
C16 C11 B1 122.3(6)
C12 C11 B1 121.2(5)
C13 C12 C11 121.6(6)
C13 C12 H12 119.2
C11 C12 H12 119.2
C14 C13 C12 119.6(7)
C14 C13 H13 120.2
C12 C13 H13 120.2
C15 C14 C13 120.8(7)
C15 C14 H14 119.6
C13 C14 H14 119.6
C14 C15 C16 120.1(7)
C14 C15 H15 119.9
C16 C15 H15 119.9
C11 C16 C15 121.4(7)
C11 C16 H16 119.3
C15 C16 H16 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 C11 1.600(9)
B1 N1 1.615(7)
B1 Br1 2.049(6)
B1 Br2 2.058(7)
N1 C1 1.503(9)
N1 C2 1.512(8)
N1 H1 0.85(7)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C11 C16 1.392(9)
C11 C12 1.429(9)
C12 C13 1.381(9)
C12 H12 0.9500
C13 C14 1.375(10)
C13 H13 0.9500
C14 C15 1.369(11)
C14 H14 0.9500
C15 C16 1.399(10)
C15 H15 0.9500
C16 H16 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 Br1 3_556 0.85(7) 2.96(7) 3.705(6) 147(6)
N1 H1 Br2 3_556 0.85(7) 2.96(7) 3.684(5) 143(6)
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 B1 N1 C1 -62.4(7)
Br1 B1 N1 C1 62.2(6)
Br2 B1 N1 C1 174.1(4)
C11 B1 N1 C2 61.9(7)
Br1 B1 N1 C2 -173.4(4)
Br2 B1 N1 C2 -61.6(6)
N1 B1 C11 C16 -91.3(6)
Br1 B1 C11 C16 148.1(5)
Br2 B1 C11 C16 28.6(6)
N1 B1 C11 C12 86.2(6)
Br1 B1 C11 C12 -34.4(6)
Br2 B1 C11 C12 -153.9(4)
C16 C11 C12 C13 -0.7(8)
B1 C11 C12 C13 -178.3(5)
C11 C12 C13 C14 -0.2(9)
C12 C13 C14 C15 1.2(9)
C13 C14 C15 C16 -1.3(9)
C12 C11 C16 C15 0.6(8)
B1 C11 C16 C15 178.2(5)
C14 C15 C16 C11 0.4(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061337
