#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/19/2241937.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_2241937
loop_
_publ_author_name
'Navarrete Guitérrez, Angélica'
'Aguirre Hernández, Gerardo'
'Bernès, Sylvain'
_publ_section_title
;
 Crystal structures of p-substituted derivatives of
 2,6-dimethylbromobenzene with {\scriptstyle{1øver2}} {łeq} Z'
 {łeq} 4
;
_journal_coeditor_code           IS5462
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1762
_journal_page_last               1767
_journal_paper_doi               10.1107/S2056989016017485
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C8 H10 Br N'
_chemical_formula_moiety         'C8 H10 Br N'
_chemical_formula_sum            'C8 H10 Br N'
_chemical_formula_weight         200.08
_chemical_melting_point          346
_chemical_name_common            4-Bromo-3,5-dimethylaniline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.0731(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.48314(15)
_cell_length_b                   6.10173(10)
_cell_length_c                   26.6195(5)
_cell_measurement_reflns_used    14036
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      71.4250
_cell_measurement_theta_min      3.3640
_cell_volume                     1676.48(5)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
CifTab (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296.0(10)
_diffrn_detector_area_resol_mean 5.1980
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku OD SuperNova AtlasS2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            39830
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.790
_diffrn_reflns_theta_min         3.373
_exptl_absorpt_coefficient_mu    6.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.435
_refine_diff_density_min         -1.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0779P)²+1.0194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1647
_reflns_number_gt                2716
_reflns_number_total             3276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is5462sup1.cif
_cod_data_source_block           3
_cod_database_code               2241937
_cod_database_fobs_code          2241937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
Br Br1 0.24694(5) 0.23484(10) 0.15702(3) 0.1038(3) Uani d 1
N N1 -0.1935(4) 0.7889(7) 0.20733(16) 0.0868(12) Uani d 1
H H1A -0.201(5) 0.787(7) 0.2398(9) 0.104 Uiso d 1
H H1B -0.202(5) 0.918(5) 0.1918(15) 0.104 Uiso d 1
C C1 0.0703(3) 0.5931(7) 0.14294(14) 0.0673(9) Uani d 1
C C2 0.1125(3) 0.4160(6) 0.17418(14) 0.0618(8) Uani d 1
C C3 0.0613(3) 0.3673(6) 0.21759(14) 0.0616(8) Uani d 1
C C4 -0.0384(3) 0.4981(6) 0.22843(12) 0.0601(8) Uani d 1
H H4A -0.0745 0.4684 0.2572 0.072 Uiso calc 1
C C5 -0.0852(3) 0.6715(7) 0.19735(13) 0.0608(8) Uani d 1
C C6 -0.0292(4) 0.7188(6) 0.15532(15) 0.0673(9) Uani d 1
H H6A -0.0593 0.8382 0.1349 0.081 Uiso calc 1
C C7 0.1289(6) 0.6536(10) 0.0969(2) 0.1049(17) Uani d 1
H H7A 0.2212 0.6663 0.1067 0.157 Uiso calc 1
H H7B 0.0938 0.7910 0.0834 0.157 Uiso calc 1
H H7C 0.1091 0.5419 0.0713 0.157 Uiso calc 1
C C8 0.1109(5) 0.1815(8) 0.2535(2) 0.0951(14) Uani d 1
H H8A 0.1029 0.0456 0.2351 0.143 Uiso calc 1
H H8B 0.0611 0.1745 0.2805 0.143 Uiso calc 1
H H8C 0.2003 0.2068 0.2678 0.143 Uiso calc 1
Br Br11 0.72828(6) -0.22871(10) -0.00212(2) 0.0996(3) Uani d 1
N N11 0.6186(4) 0.3496(7) 0.17122(14) 0.0816(10) Uani d 1
H H11A 0.658(4) 0.480(5) 0.1713(19) 0.098 Uiso d 1
H H11B 0.536(2) 0.356(7) 0.1745(18) 0.098 Uiso d 1
C C11 0.5864(3) -0.0934(7) 0.07484(15) 0.0681(9) Uani d 1
C C12 0.6933(3) -0.0488(7) 0.05224(13) 0.0652(9) Uani d 1
C C13 0.7753(3) 0.1285(7) 0.06764(13) 0.0652(9) Uani d 1
C C14 0.7478(4) 0.2596(6) 0.10694(14) 0.0648(9) Uani d 1
H H14A 0.8018 0.3773 0.1180 0.078 Uiso calc 1
C C15 0.6412(4) 0.2187(7) 0.13007(14) 0.0649(9) Uani d 1
C C16 0.5626(3) 0.0413(7) 0.11379(14) 0.0688(10) Uani d 1
H H16A 0.4918 0.0122 0.1295 0.083 Uiso calc 1
C C17 0.4956(5) -0.2818(8) 0.0571(2) 0.0917(14) Uani d 1
H H17A 0.4340 -0.2971 0.0796 0.138 Uiso calc 1
H H17B 0.5447 -0.4147 0.0572 0.138 Uiso calc 1
H H17C 0.4507 -0.2530 0.0231 0.138 Uiso calc 1
C C18 0.8907(5) 0.1869(9) 0.04352(18) 0.0884(13) Uani d 1
H H18A 0.8643 0.1973 0.0072 0.133 Uiso calc 1
H H18B 0.9558 0.0755 0.0513 0.133 Uiso calc 1
H H18C 0.9254 0.3251 0.0567 0.133 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C5 N1 H1A 113(3)
C5 N1 H1B 113(3)
H1A N1 H1B 117(3)
C6 C1 C2 117.7(3)
C6 C1 C7 119.3(4)
C2 C1 C7 123.0(4)
C1 C2 C3 122.4(3)
C1 C2 Br1 118.6(3)
C3 C2 Br1 119.0(3)
C4 C3 C2 117.8(3)
C4 C3 C8 119.2(4)
C2 C3 C8 123.0(4)
C5 C4 C3 121.3(3)
C5 C4 H4A 119.4
C3 C4 H4A 119.4
C4 C5 C6 119.3(3)
C4 C5 N1 119.5(3)
C6 C5 N1 121.2(4)
C1 C6 C5 121.5(4)
C1 C6 H6A 119.2
C5 C6 H6A 119.2
C1 C7 H7A 109.5
C1 C7 H7B 109.5
H7A C7 H7B 109.5
C1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C3 C8 H8A 109.5
C3 C8 H8B 109.5
H8A C8 H8B 109.5
C3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C15 N11 H11A 111(3)
C15 N11 H11B 114(3)
H11A N11 H11B 115(3)
C16 C11 C12 118.3(4)
C16 C11 C17 120.0(4)
C12 C11 C17 121.6(4)
C11 C12 C13 121.8(3)
C11 C12 Br11 119.6(3)
C13 C12 Br11 118.6(3)
C14 C13 C12 118.0(3)
C14 C13 C18 118.2(4)
C12 C13 C18 123.8(4)
C13 C14 C15 121.3(4)
C13 C14 H14A 119.3
C15 C14 H14A 119.3
C16 C15 C14 118.9(3)
C16 C15 N11 121.0(3)
C14 C15 N11 120.0(4)
C11 C16 C15 121.7(3)
C11 C16 H16A 119.2
C15 C16 H16A 119.2
C11 C17 H17A 109.5
C11 C17 H17B 109.5
H17A C17 H17B 109.5
C11 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C13 C18 H18A 109.5
C13 C18 H18B 109.5
H18A C18 H18B 109.5
C13 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.908(3)
N1 C5 1.407(5)
N1 H1A 0.881(18)
N1 H1B 0.886(18)
C1 C6 1.380(5)
C1 C2 1.388(6)
C1 C7 1.510(5)
C2 C3 1.389(5)
C3 C4 1.385(5)
C3 C8 1.515(6)
C4 C5 1.379(5)
C4 H4A 0.9300
C5 C6 1.382(5)
C6 H6A 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
Br11 C12 1.902(3)
N11 C15 1.409(5)
N11 H11A 0.897(18)
N11 H11B 0.884(18)
C11 C16 1.380(5)
C11 C12 1.389(5)
C11 C17 1.514(6)
C12 C13 1.398(6)
C13 C14 1.387(5)
C13 C18 1.508(5)
C14 C15 1.390(5)
C14 H14A 0.9300
C15 C16 1.383(6)
C16 H16A 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
_geom_hbond_publ_flag
N1 H1A N11 2 0.881(18) 2.41(3) 3.212(6) 152(5) yes
N11 H11A N1 1_655 0.897(18) 2.52(3) 3.365(6) 157(4) yes
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
C6 C1 C2 C3 -2.1(6)
C7 C1 C2 C3 177.4(4)
C6 C1 C2 Br1 178.4(3)
C7 C1 C2 Br1 -2.1(5)
C1 C2 C3 C4 2.1(5)
Br1 C2 C3 C4 -178.4(3)
C1 C2 C3 C8 -176.8(4)
Br1 C2 C3 C8 2.6(5)
C2 C3 C4 C5 -0.2(5)
C8 C3 C4 C5 178.8(4)
C3 C4 C5 C6 -1.7(6)
C3 C4 C5 N1 174.7(4)
C2 C1 C6 C5 0.1(6)
C7 C1 C6 C5 -179.4(4)
C4 C5 C6 C1 1.7(6)
N1 C5 C6 C1 -174.6(4)
C16 C11 C12 C13 -0.6(5)
C17 C11 C12 C13 178.3(4)
C16 C11 C12 Br11 -179.3(3)
C17 C11 C12 Br11 -0.4(5)
C11 C12 C13 C14 0.7(5)
Br11 C12 C13 C14 179.3(3)
C11 C12 C13 C18 -178.5(4)
Br11 C12 C13 C18 0.2(5)
C12 C13 C14 C15 -0.8(6)
C18 C13 C14 C15 178.4(4)
C13 C14 C15 C16 0.9(6)
C13 C14 C15 N11 177.6(4)
C12 C11 C16 C15 0.8(6)
C17 C11 C16 C15 -178.2(4)
C14 C15 C16 C11 -0.9(6)
N11 C15 C16 C11 -177.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139088215
