#------------------------------------------------------------------------------
#$Date: 2018-04-30 18:31:29 +0200 (lun 30 de abr de 2018) $
#$Revision: 207562 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/24/2242476.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_2242476
loop_
_publ_author_name
'Hill, Tania N.'
'Savig, Kelsey L.'
'Lemmerer, Andreas'
_publ_section_title
;
 Crystal structure of 5-[2-(2,4,6-tribromophenyl)diazenyl]tropolone
;
_journal_coeditor_code           FY2127
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              709
_journal_page_last               712
_journal_paper_doi               10.1107/S2056989018006151
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C13 H7 Br3 N2 O2'
_chemical_formula_moiety         'C13 H7 Br3 N2 O2'
_chemical_formula_sum            'C13 H7 Br3 N2 O2'
_chemical_formula_weight         462.94
_chemical_name_common
;
5-[2-(2,4,6-Tribromophenyl)diazenyl]tropolone
;
_chemical_name_systematic
;
2-Hydroxy-5-[2-(2,4,6-tribromophenyl)diazen-1-yl]cyclohepta-2,4,6-trien-1-one
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.5600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1742(3)
_cell_length_b                   4.78850(10)
_cell_length_c                   16.0308(3)
_cell_measurement_reflns_used    8182
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.32
_cell_volume                     1350.31(4)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2004) and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_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  0.0546
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27599
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         2.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.963
_exptl_absorpt_correction_T_max  0.5727
_exptl_absorpt_correction_T_min  0.1239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.684
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_gt           0.0225
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0151P)²+1.5233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.051
_reflns_number_gt                2744
_reflns_number_total             3258
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fy2127sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2242476
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
C C1 0.41630(13) 1.5974(5) 0.51392(14) 0.0173(5) Uani d . 1
C C2 0.45286(13) 1.6351(5) 0.60559(14) 0.0171(4) Uani d . 1
C C3 0.43788(13) 1.5012(5) 0.67536(15) 0.0189(5) Uani d . 1
H H3 0.4684 1.5592 0.7298 0.023 Uiso calc R 1
C C4 0.38490(13) 1.2934(5) 0.67894(14) 0.0191(5) Uani d . 1
H H4 0.3844 1.2338 0.7353 0.023 Uiso calc R 1
C C5 0.33337(12) 1.1622(5) 0.61327(14) 0.0163(4) Uani d . 1
C C6 0.32247(13) 1.2070(5) 0.52358(14) 0.0181(5) Uani d . 1
H H6 0.285 1.0929 0.4873 0.022 Uiso calc R 1
C C7 0.35821(13) 1.3907(5) 0.48232(15) 0.0190(5) Uani d . 1
H H7 0.3419 1.3811 0.4213 0.023 Uiso calc R 1
C C11 0.20015(13) 0.6200(5) 0.62034(14) 0.0171(4) Uani d . 1
C C12 0.14250(13) 0.4963(5) 0.55595(14) 0.0184(5) Uani d . 1
C C13 0.09308(13) 0.2960(5) 0.57313(15) 0.0208(5) Uani d . 1
H H13 0.0542 0.2182 0.5282 0.025 Uiso calc R 1
C C14 0.10233(13) 0.2135(5) 0.65781(16) 0.0213(5) Uani d . 1
C C15 0.15835(14) 0.3243(5) 0.72361(15) 0.0208(5) Uani d . 1
H H15 0.1639 0.263 0.7812 0.025 Uiso calc R 1
C C16 0.20691(13) 0.5268(5) 0.70536(14) 0.0186(5) Uani d . 1
N N1 0.28798(11) 0.9647(4) 0.64541(13) 0.0221(4) Uani d . 1
N N2 0.24557(11) 0.8171(4) 0.58994(12) 0.0200(4) Uani d . 1
O O1 0.43793(10) 1.7538(4) 0.46231(10) 0.0230(4) Uani d . 1
O O2 0.50700(10) 1.8299(3) 0.62292(11) 0.0225(4) Uani d . 1
H H2 0.511 1.9037 0.5767 0.034 Uiso calc R 1
Br Br1 0.128145(15) 0.60750(6) 0.439523(15) 0.02966(7) Uani d . 1
Br Br2 0.282839(16) 0.65030(6) 0.802286(15) 0.03009(8) Uani d . 1
Br Br3 0.036554(14) -0.06019(5) 0.684700(18) 0.02738(7) Uani d . 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 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
O1 C1 C7 120.2(2)
O1 C1 C2 116.8(2)
C7 C1 C2 123.0(2)
O2 C2 C3 116.3(2)
O2 C2 C1 114.9(2)
C3 C2 C1 128.8(2)
C2 C3 C4 130.2(2)
C2 C3 H3 114.9
C4 C3 H3 114.9
C5 C4 C3 129.7(2)
C5 C4 H4 115.1
C3 C4 H4 115.1
C4 C5 C6 127.1(2)
C4 C5 N1 111.70(19)
C6 C5 N1 121.2(2)
C7 C6 C5 129.0(2)
C7 C6 H6 115.5
C5 C6 H6 115.5
C6 C7 C1 132.0(2)
C6 C7 H7 114
C1 C7 H7 114
C12 C11 C16 116.4(2)
C12 C11 N2 114.79(19)
C16 C11 N2 128.8(2)
C13 C12 C11 123.1(2)
C13 C12 Br1 117.00(17)
C11 C12 Br1 119.88(17)
C14 C13 C12 117.9(2)
C14 C13 H13 121.1
C12 C13 H13 121.1
C15 C14 C13 121.8(2)
C15 C14 Br3 118.70(18)
C13 C14 Br3 119.53(18)
C14 C15 C16 119.6(2)
C14 C15 H15 120.2
C16 C15 H15 120.2
C15 C16 C11 121.2(2)
C15 C16 Br2 114.52(17)
C11 C16 Br2 124.22(17)
N2 N1 C5 115.36(19)
N1 N2 C11 116.30(19)
C2 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.250(3)
C1 C7 1.443(3)
C1 C2 1.464(3)
C2 O2 1.333(3)
C2 C3 1.375(3)
C3 C4 1.396(3)
C3 H3 0.95
C4 C5 1.373(3)
C4 H4 0.95
C5 C6 1.417(3)
C5 N1 1.433(3)
C6 C7 1.360(3)
C6 H6 0.95
C7 H7 0.95
C11 C12 1.404(3)
C11 C16 1.410(3)
C11 N2 1.419(3)
C12 C13 1.388(3)
C12 Br1 1.895(2)
C13 C14 1.383(3)
C13 H13 0.95
C14 C15 1.375(3)
C14 Br3 1.895(2)
C15 C16 1.391(3)
C15 H15 0.95
C16 Br2 1.895(2)
N1 N2 1.241(3)
O2 H2 0.84
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
C6 H6 N2 . 0.95 2.36 2.705(3) 101
O2 H2 O1 . 0.84 2.1 2.591(2) 116.7
C3 H3 O2 2_646 0.95 2.54 3.241(3) 130.7
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
O1 C1 C2 O2 -1.7(3)
C7 C1 C2 O2 178.0(2)
O1 C1 C2 C3 177.0(2)
C7 C1 C2 C3 -3.4(4)
O2 C2 C3 C4 179.1(2)
C1 C2 C3 C4 0.5(4)
C2 C3 C4 C5 0.9(5)
C3 C4 C5 C6 0.9(4)
C3 C4 C5 N1 -178.5(2)
C4 C5 C6 C7 -1.8(4)
N1 C5 C6 C7 177.6(2)
C5 C6 C7 C1 -1.0(4)
O1 C1 C7 C6 -176.5(2)
C2 C1 C7 C6 3.9(4)
C16 C11 C12 C13 1.1(3)
N2 C11 C12 C13 179.1(2)
C16 C11 C12 Br1 179.71(16)
N2 C11 C12 Br1 -2.3(3)
C11 C12 C13 C14 -0.9(4)
Br1 C12 C13 C14 -179.57(17)
C12 C13 C14 C15 0.0(4)
C12 C13 C14 Br3 -179.80(17)
C13 C14 C15 C16 0.6(4)
Br3 C14 C15 C16 -179.58(17)
C14 C15 C16 C11 -0.4(4)
C14 C15 C16 Br2 -178.21(18)
C12 C11 C16 C15 -0.4(3)
N2 C11 C16 C15 -178.1(2)
C12 C11 C16 Br2 177.20(17)
N2 C11 C16 Br2 -0.5(4)
C4 C5 N1 N2 -172.8(2)
C6 C5 N1 N2 7.7(3)
C5 N1 N2 C11 179.97(19)
C12 C11 N2 N1 167.9(2)
C16 C11 N2 N1 -14.3(4)

_cod_database_fobs_code 2242476
