#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/83/2238377.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_2238377
loop_
_publ_author_name
'Chetioui, Souheyla'
'Boudraa, Issam'
'Bouacida, Sofiane'
'Bouchoul, Abdelkader'
'Bouaoud, Salah Eddine'
_publ_section_title
;
 (E)-1-[(2,4,6-Tribromophenyl)diazenyl]naphthalen-2-ol
;
_journal_coeditor_code           IS5290
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1250
_journal_paper_doi               10.1107/S1600536813018977
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H9 Br3 N2 O'
_chemical_formula_moiety         'C16 H9 Br3 N2 O'
_chemical_formula_sum            'C16 H9 Br3 N2 O'
_chemical_formula_weight         484.98
_chemical_melting_point          422
_chemical_name_common
(E)-1-((2,4,6-tribromophenyl)diazenyl)naphthalen-2-ol.
_chemical_name_systematic
;
(E)-1-[(2,4,6-Tribromophenyl)diazenyl]naphthalen-2-ol
;
_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           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9904(11)
_cell_length_b                   15.689(4)
_cell_length_c                   24.580(7)
_cell_measurement_reflns_used    2052
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      3.12
_cell_volume                     1538.8(7)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13143
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.1
_exptl_absorpt_coefficient_mu    7.866
_exptl_absorpt_correction_T_max  0.3318
_exptl_absorpt_correction_T_min  0.2439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.436
_refine_ls_abs_structure_details 'Flack (1983), 1553 Friedel pairs'
_refine_ls_abs_structure_Flack   0.004(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0338
_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)+(0.0241P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                2910
_reflns_number_total             3841
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5290.cif
_cod_data_source_block           I
_cod_database_code               2238377
_cod_database_fobs_code          2238377
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
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_thermal_displace_type
_atom_site_occupancy
Br Br1 -0.12633(11) -0.15833(2) 0.00161(2) 0.03790(10) Uani 1.000
Br Br2 0.51026(12) 0.09227(3) 0.12476(2) 0.0481(2) Uani 1.000
Br Br3 0.12463(15) 0.17248(3) -0.08940(2) 0.0557(2) Uani 1.000
O O1 -0.4121(9) 0.02557(17) -0.18018(11) 0.0512(10) Uani 1.000
N N1 -0.0964(9) -0.01183(18) -0.09266(12) 0.0352(10) Uani 1.000
N N2 -0.0368(8) -0.08820(18) -0.10973(11) 0.0317(10) Uani 1.000
C C1 0.0433(10) 0.0081(2) -0.04134(14) 0.0304(11) Uani 1.000
C C2 0.0607(9) -0.0479(2) 0.00323(14) 0.0304(11) Uani 1.000
C C3 0.2004(11) -0.0226(2) 0.05163(14) 0.0333(12) Uani 1.000
C C4 0.3199(11) 0.0592(2) 0.05766(15) 0.0342(11) Uani 1.000
C C5 0.2983(11) 0.1171(2) 0.01563(15) 0.0373(14) Uani 1.000
C C6 0.1572(11) 0.0906(2) -0.03316(14) 0.0337(11) Uani 1.000
C C7 -0.1725(10) -0.1097(2) -0.15902(14) 0.0307(11) Uani 1.000
C C8 -0.3485(12) -0.0537(3) -0.19353(15) 0.0387(14) Uani 1.000
C C9 -0.4639(11) -0.0836(3) -0.24475(15) 0.0432(15) Uani 1.000
C C10 -0.4111(11) -0.1653(3) -0.25976(14) 0.0437(15) Uani 1.000
C C11 -0.2321(11) -0.2247(3) -0.22725(14) 0.0355(11) Uani 1.000
C C12 -0.1079(10) -0.1969(2) -0.17622(14) 0.0299(11) Uani 1.000
C C13 0.0637(11) -0.2558(2) -0.14376(15) 0.0360(14) Uani 1.000
C C14 0.1125(12) -0.3377(2) -0.16128(16) 0.0443(14) Uani 1.000
C C15 -0.0059(13) -0.3643(3) -0.21170(17) 0.0487(16) Uani 1.000
C C16 -0.1756(13) -0.3094(3) -0.24383(16) 0.0470(16) Uani 1.000
H H1 -0.33456 0.03546 -0.14993 0.0768 Uiso 1.000
H H3 0.21435 -0.06078 0.08045 0.0402 Uiso 1.000
H H5 0.37633 0.17259 0.01985 0.0449 Uiso 1.000
H H9 -0.57652 -0.04673 -0.26807 0.0520 Uiso 1.000
H H10 -0.49596 -0.18353 -0.29301 0.0524 Uiso 1.000
H H13 0.14544 -0.23913 -0.10996 0.0432 Uiso 1.000
H H14 0.22647 -0.37609 -0.13916 0.0531 Uiso 1.000
H H15 0.03174 -0.41991 -0.22331 0.0588 Uiso 1.000
H H16 -0.25621 -0.32774 -0.27734 0.0563 Uiso 1.000
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 0 '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 0.006 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C8 O1 H1 109.00 no
N2 N1 C1 115.0(3) no
N1 N2 C7 116.3(3) no
N1 C1 C2 125.2(3) no
C2 C1 C6 117.0(3) no
N1 C1 C6 117.7(3) no
Br1 C2 C3 116.4(2) no
C1 C2 C3 121.0(3) no
Br1 C2 C1 122.5(3) no
C2 C3 C4 120.2(3) no
Br2 C4 C5 119.9(3) no
C3 C4 C5 120.8(3) no
Br2 C4 C3 119.3(3) no
C4 C5 C6 118.4(3) no
Br3 C6 C5 117.1(2) no
C1 C6 C5 122.5(3) no
Br3 C6 C1 120.4(3) no
N2 C7 C12 114.8(3) no
C8 C7 C12 120.0(3) no
N2 C7 C8 125.2(3) no
O1 C8 C9 118.2(4) no
C7 C8 C9 119.3(4) no
O1 C8 C7 122.5(3) no
C8 C9 C10 120.3(4) no
C9 C10 C11 123.2(4) no
C10 C11 C16 122.5(4) no
C12 C11 C16 119.4(4) no
C10 C11 C12 118.2(4) no
C7 C12 C13 122.8(3) no
C11 C12 C13 118.2(3) no
C7 C12 C11 119.0(3) no
C12 C13 C14 120.7(3) no
C13 C14 C15 120.9(4) no
C14 C15 C16 120.0(4) no
C11 C16 C15 120.9(4) no
C2 C3 H3 120.00 no
C4 C3 H3 120.00 no
C4 C5 H5 121.00 no
C6 C5 H5 121.00 no
C8 C9 H9 120.00 no
C10 C9 H9 120.00 no
C9 C10 H10 118.00 no
C11 C10 H10 118.00 no
C12 C13 H13 120.00 no
C14 C13 H13 120.00 no
C13 C14 H14 120.00 no
C15 C14 H14 120.00 no
C14 C15 H15 120.00 no
C16 C15 H15 120.00 no
C11 C16 H16 120.00 no
C15 C16 H16 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 1.887(3) no
Br2 C4 1.889(4) no
Br3 C6 1.892(3) no
O1 C8 1.311(5) no
O1 H1 0.8200 no
N1 N2 1.292(4) no
N1 C1 1.414(5) no
N2 C7 1.369(5) no
C1 C2 1.406(5) no
C1 C6 1.387(5) no
C2 C3 1.373(5) no
C3 C4 1.377(5) no
C4 C5 1.378(5) no
C5 C6 1.389(5) no
C7 C8 1.409(6) no
C7 C12 1.455(5) no
C8 C9 1.420(6) no
C9 C10 1.350(7) no
C10 C11 1.420(6) no
C11 C16 1.408(7) no
C11 C12 1.418(5) no
C12 C13 1.400(5) no
C13 C14 1.369(5) no
C14 C15 1.390(6) no
C15 C16 1.351(7) no
C3 H3 0.9300 no
C5 H5 0.9300 no
C9 H9 0.9300 no
C10 H10 0.9300 no
C13 H13 0.9300 no
C14 H14 0.9300 no
C15 H15 0.9300 no
C16 H16 0.9300 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.85 2.561(4) 144 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
_geom_torsion_publ_flag
C1 N1 N2 C7 179.2(3) no
N2 N1 C1 C2 -38.6(5) no
N2 N1 C1 C6 144.9(4) no
N1 N2 C7 C8 4.8(6) no
N1 N2 C7 C12 -178.4(3) no
N1 C1 C2 Br1 -3.5(5) no
N1 C1 C2 C3 -179.8(4) no
C6 C1 C2 Br1 173.1(3) no
C6 C1 C2 C3 -3.2(6) no
N1 C1 C6 Br3 -0.1(5) no
N1 C1 C6 C5 179.9(4) no
C2 C1 C6 Br3 -176.9(3) no
C2 C1 C6 C5 3.1(6) no
Br1 C2 C3 C4 -175.1(3) no
C1 C2 C3 C4 1.4(6) no
C2 C3 C4 Br2 179.9(3) no
C2 C3 C4 C5 0.7(6) no
Br2 C4 C5 C6 179.9(3) no
C3 C4 C5 C6 -0.8(6) no
C4 C5 C6 Br3 178.9(3) no
C4 C5 C6 C1 -1.1(6) no
N2 C7 C8 O1 -3.0(7) no
N2 C7 C8 C9 177.3(4) no
C12 C7 C8 O1 -179.7(4) no
C12 C7 C8 C9 0.6(6) no
N2 C7 C12 C11 -178.7(3) no
N2 C7 C12 C13 3.3(6) no
C8 C7 C12 C11 -1.6(6) no
C8 C7 C12 C13 -179.6(4) no
O1 C8 C9 C10 -178.5(4) no
C7 C8 C9 C10 1.3(7) no
C8 C9 C10 C11 -2.1(7) no
C9 C10 C11 C12 1.0(6) no
C9 C10 C11 C16 -179.2(4) no
C10 C11 C12 C7 0.9(6) no
C10 C11 C12 C13 179.0(4) no
C16 C11 C12 C7 -179.0(4) no
C16 C11 C12 C13 -0.9(6) no
C10 C11 C16 C15 -179.6(4) no
C12 C11 C16 C15 0.2(7) no
C7 C12 C13 C14 178.7(4) no
C11 C12 C13 C14 0.7(6) no
C12 C13 C14 C15 0.2(7) no
C13 C14 C15 C16 -0.9(7) no
C14 C15 C16 C11 0.7(7) no
