#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/23/2222337.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_2222337
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Kennedy, Alan R.'
'Cordoba, Cristina'
_publ_section_title
;
 4-Bromo-4'-(dimethylamino)stilbene
;
_journal_coeditor_code           HG2518
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1475
_journal_paper_doi               10.1107/S1600536809020492
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H16 Br N'
_chemical_formula_moiety         'C16 H16 Br N'
_chemical_formula_sum            'C16 H16 Br N'
_chemical_formula_weight         302.21
_chemical_melting_point          354.0(10)
_chemical_name_systematic
;
4-Bromo-4'-(dimethylamino)stilbene
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.331(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.804(2)
_cell_length_b                   6.0962(5)
_cell_length_c                   15.2106(10)
_cell_measurement_reflns_used    2824
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.00
_cell_measurement_theta_min      2.65
_cell_volume                     1366.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PARST95 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.064
_diffrn_reflns_av_sigmaI/netI    0.125
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8606
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.989
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.942
_refine_diff_density_min         -0.540
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.156
_refine_ls_R_factor_gt           0.075
_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)+(0.1119P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.187
_refine_ls_wR_factor_ref         0.213
_reflns_number_gt                1533
_reflns_number_total             2986
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2518.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222337
_cod_database_fobs_code          2222337
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_disorder_assembly
_atom_site_disorder_group
Br Br1 0.36239(6) -0.41740(14) 0.35579(5) 0.0487(4) Uani d . 1 . .
N N1 -0.0563(6) 0.4693(11) 0.6162(5) 0.055(2) Uani d . 1 . .
C C1 0.3671(6) -0.2184(13) 0.4545(5) 0.043(2) Uani d . 1 . .
C C2 0.4151(6) -0.2818(16) 0.5312(5) 0.055(2) Uani d . 1 . .
H H2 0.4433 -0.4217 0.5367 0.066 Uiso calc R 1 . .
C C3 0.4210(6) -0.1319(16) 0.6019(5) 0.055(2) Uani d . 1 . .
H H3 0.4562 -0.1695 0.6552 0.066 Uiso calc R 1 . .
C C4 0.3768(5) 0.0699(13) 0.5960(5) 0.0394(19) Uani d . 1 . .
C C5 0.3297(6) 0.1216(13) 0.5151(5) 0.046(2) Uani d . 1 . .
H H5 0.3014 0.2613 0.5089 0.055 Uiso calc R 1 . .
C C6 0.3215(6) -0.0195(14) 0.4429(5) 0.050(2) Uani d . 1 . .
H H6 0.2871 0.0176 0.3892 0.061 Uiso calc R 1 . .
C C7 0.3859(6) 0.2246(15) 0.6700(5) 0.050(2) Uani d . 1 . .
H H7 0.4442 0.2300 0.7017 0.060 Uiso calc R 1 . .
C C8 0.3242(6) 0.3591(14) 0.6993(5) 0.047(2) Uani d . 1 . .
H H8 0.3483 0.4566 0.7442 0.056 Uiso calc R 1 . .
C C9 0.2261(6) 0.3859(12) 0.6758(4) 0.042(2) Uani d . 1 . .
C C10 0.1699(6) 0.2157(13) 0.6391(4) 0.039(2) Uani d . 1 . .
H H10 0.1963 0.0776 0.6278 0.047 Uiso calc R 1 . .
C C11 0.0804(6) 0.2435(12) 0.6198(5) 0.041(2) Uani d . 1 . .
H H11 0.0458 0.1253 0.5936 0.049 Uiso calc R 1 . .
C C12 0.0344(6) 0.4455(11) 0.6371(5) 0.0369(18) Uani d . 1 . .
C C13 0.0914(6) 0.6088(12) 0.6775(4) 0.042(2) Uani d . 1 . .
H H13 0.0663 0.7459 0.6924 0.050 Uiso calc R 1 . .
C C14 0.1825(6) 0.5720(12) 0.6956(5) 0.043(2) Uani d . 1 . .
H H14 0.2178 0.6859 0.7242 0.052 Uiso calc R 1 . .
C C15 -0.1121(6) 0.3046(14) 0.5665(6) 0.054(2) Uani d . 1 . .
H H15A -0.0868 0.2745 0.5105 0.081 Uiso calc R 1 . .
H H15B -0.1742 0.3600 0.5547 0.081 Uiso calc R 1 . .
H H15C -0.1127 0.1692 0.6012 0.081 Uiso calc R 1 . .
C C16 -0.1007(6) 0.6780(14) 0.6312(6) 0.055(2) Uani d . 1 . .
H H16A -0.0761 0.7393 0.6880 0.082 Uiso calc R 1 . .
H H16B -0.1661 0.6543 0.6319 0.082 Uiso calc R 1 . .
H H16C -0.0898 0.7805 0.5837 0.082 Uiso calc R 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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 N1 C16 . . 120.5(7) ?
C12 N1 C15 . . 123.1(7) ?
C16 N1 C15 . . 115.9(7) ?
C2 C1 C6 . . 124.3(8) ?
C2 C1 Br1 . . 117.8(6) ?
C6 C1 Br1 . . 117.9(6) ?
C1 C2 C3 . . 117.4(8) ?
C1 C2 H2 . . 121.3 ?
C3 C2 H2 . . 121.3 ?
C4 C3 C2 . . 121.9(7) ?
C4 C3 H3 . . 119.0 ?
C2 C3 H3 . . 119.0 ?
C3 C4 C5 . . 116.8(7) ?
C3 C4 C7 . . 120.7(7) ?
C5 C4 C7 . . 122.4(8) ?
C6 C5 C4 . . 123.8(8) ?
C6 C5 H5 . . 118.1 ?
C4 C5 H5 . . 118.1 ?
C1 C6 C5 . . 115.7(7) ?
C1 C6 H6 . . 122.2 ?
C5 C6 H6 . . 122.2 ?
C8 C7 C4 . . 129.5(8) ?
C8 C7 H7 . . 115.2 ?
C4 C7 H7 . . 115.2 ?
C7 C8 C9 . . 132.6(8) ?
C7 C8 H8 . . 113.7 ?
C9 C8 H8 . . 113.7 ?
C14 C9 C10 . . 115.4(8) ?
C14 C9 C8 . . 121.3(7) ?
C10 C9 C8 . . 123.1(7) ?
C11 C10 C9 . . 121.9(8) ?
C11 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
C10 C11 C12 . . 122.7(7) ?
C10 C11 H11 . . 118.7 ?
C12 C11 H11 . . 118.7 ?
N1 C12 C13 . . 124.4(7) ?
N1 C12 C11 . . 121.4(7) ?
C13 C12 C11 . . 114.2(8) ?
C14 C13 C12 . . 120.7(7) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C9 C14 C13 . . 125.0(7) ?
C9 C14 H14 . . 117.5 ?
C13 C14 H14 . . 117.5 ?
N1 C15 H15A . . 109.5 ?
N1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N1 C16 H16A . . 109.5 ?
N1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.927(8) ?
N1 C12 . 1.359(11) ?
N1 C16 . 1.460(10) ?
N1 C15 . 1.465(11) ?
C1 C2 . 1.364(10) ?
C1 C6 . 1.391(11) ?
C2 C3 . 1.408(12) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.392(11) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.393(10) ?
C4 C7 . 1.465(11) ?
C5 C6 . 1.392(11) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.334(12) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.472(12) ?
C8 H8 . 0.9500 ?
C9 C14 . 1.353(11) ?
C9 C10 . 1.412(10) ?
C10 C11 . 1.342(11) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.443(10) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.408(11) ?
C13 C14 . 1.371(11) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -2.3(14) ?
Br1 C1 C2 C3 . . . . 177.7(6) ?
C1 C2 C3 C4 . . . . 2.7(13) ?
C2 C3 C4 C5 . . . . -2.9(12) ?
C2 C3 C4 C7 . . . . -178.7(8) ?
C3 C4 C5 C6 . . . . 2.8(12) ?
C7 C4 C5 C6 . . . . 178.5(8) ?
C2 C1 C6 C5 . . . . 2.1(13) ?
Br1 C1 C6 C5 . . . . -177.8(6) ?
C4 C5 C6 C1 . . . . -2.4(12) ?
C3 C4 C7 C8 . . . . -142.8(9) ?
C5 C4 C7 C8 . . . . 41.7(13) yes
C4 C7 C8 C9 . . . . 7.1(15) yes
C7 C8 C9 C14 . . . . -160.7(9) ?
C7 C8 C9 C10 . . . . 25.4(12) yes
C14 C9 C10 C11 . . . . 4.5(10) ?
C8 C9 C10 C11 . . . . 178.7(7) ?
C9 C10 C11 C12 . . . . -1.8(10) ?
C16 N1 C12 C13 . . . . 3.1(11) ?
C15 N1 C12 C13 . . . . 173.9(7) ?
C16 N1 C12 C11 . . . . -177.6(7) ?
C15 N1 C12 C11 . . . . -6.8(11) ?
C10 C11 C12 N1 . . . . 179.5(7) ?
C10 C11 C12 C13 . . . . -1.1(10) ?
N1 C12 C13 C14 . . . . -179.3(7) ?
C11 C12 C13 C14 . . . . 1.3(9) ?
C10 C9 C14 C13 . . . . -4.4(10) ?
C8 C9 C14 C13 . . . . -178.8(7) ?
C12 C13 C14 C9 . . . . 1.5(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742515
