#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100370.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2100370
_journal_coeditor_code         DE5020
_journal_date_accepted         2005-11-19
_journal_date_recd_electronic  2005-04-29
_journal_issue                 1
_journal_name_full             'Acta Crystallographica, Section B'
_journal_page_first            109
_journal_page_last             117
_journal_paper_category        FA
_journal_volume                62
_journal_year                  2006
_chemical_formula_moiety       'C7 H3 Br2 N O'
_chemical_formula_sum          'C7 H3 Br2 N O'
_chemical_formula_weight       276.92
_chemical_melting_point        ?
_chemical_name_common          Bromoxynil
_chemical_name_systematic
;
 3,5-dibromo-4-hydroxybenzonitrile
;
_symmetry_cell_setting         triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXTL
_cell_angle_alpha              79.680(10)
_cell_angle_beta               83.710(10)
_cell_angle_gamma              83.060(10)
_cell_formula_units_Z          '4 '
_cell_length_a                 3.9684(10)
_cell_length_b                 12.669(3)
_cell_length_c                 16.047(4)
_cell_measurement_reflns_used  2619
_cell_measurement_temperature  174(2)
_cell_measurement_theta_max    27.20
_cell_measurement_theta_min    2.83
_cell_volume                   784.7(3)
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_data_reduction      SAINT
_computing_molecular_graphics  SHELXTL
_computing_publication_material SHELXTL
_computing_structure_refinement SHELXTL
_computing_structure_solution  'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature    174(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
;
Siemens area detector diffractometer
;
_diffrn_measurement_method     '\w 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 0.042
_diffrn_reflns_av_sigmaI/netI  0.058
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_l_max     20
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_number          8883
_diffrn_reflns_theta_full      27.49
_diffrn_reflns_theta_max       27.49
_diffrn_reflns_theta_min       1.30
_diffrn_standards_decay_%      'less than 1'
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  10.263
_exptl_absorpt_correction_T_max 0.440
_exptl_absorpt_correction_T_min 0.105
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
 SADABS;  Sheldrick, 1996;  Blessing, 1995'
;
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  2.344
_exptl_crystal_density_meas    'not measured'
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     plate
_exptl_crystal_F_000           520
_exptl_crystal_size_max        0.40
_exptl_crystal_size_mid        0.20
_exptl_crystal_size_min        0.08
_refine_diff_density_max       1.74
_refine_diff_density_min       -1.61
_refine_ls_extinction_coef     ?
_refine_ls_extinction_expression
;
 Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
;
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.09
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   200
_refine_ls_number_reflns       3510
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.09
_refine_ls_R_factor_all        0.057
_refine_ls_R_factor_gt         0.047
_refine_ls_shift/su_max        0.002
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 calc w=1/[\s^2^(Fo^2^)+(0.066P)^2^+0.42P] where
P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.117
_refine_ls_wR_factor_ref       0.120
_reflns_number_gt              2975
_reflns_number_total           3510
_reflns_threshold_expression   '>2\s(I) '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
C11 -0.0095(12) 0.9176(4) 0.3529(3) 0.0227(10) Uani d . 1 . . C
C12 -0.0705(12) 0.9253(4) 0.2676(3) 0.0232(10) Uani d . 1 . . C
H12 -0.1906 0.9882 0.2386 0.028 Uiso calc R 1 . . H
Br13 -0.04126(13) 0.84563(5) 0.11182(3) 0.02951(17) Uani d . 1 . . Br
C13 0.0476(12) 0.8394(4) 0.2264(3) 0.0229(10) Uani d . 1 . . C
O14 0.3444(9) 0.6603(3) 0.2300(2) 0.0320(9) Uani d . 1 . . O
H14 0.2966 0.6726 0.1792 0.048 Uiso calc R 1 . . H
C14 0.2266(11) 0.7469(4) 0.2676(3) 0.0228(10) Uani d . 1 . . C
Br15 0.51745(13) 0.61547(4) 0.41019(3) 0.02696(17) Uani d . 1 . . Br
C15 0.2814(12) 0.7423(4) 0.3526(3) 0.0240(11) Uani d . 1 . . C
C16 0.1678(12) 0.8260(4) 0.3959(3) 0.0220(10) Uani d . 1 . . C
H16 0.2092 0.8214 0.4537 0.026 Uiso calc R 1 . . H
N17 -0.2474(12) 1.0800(4) 0.4266(3) 0.0336(11) Uani d . 1 . . N
C17 -0.1384(12) 1.0078(4) 0.3959(3) 0.0254(11) Uani d . 1 . . C
C21 0.8384(11) 0.4237(4) 0.1469(3) 0.0208(10) Uani d . 1 . . C
C22 0.8960(12) 0.4265(4) 0.2305(3) 0.0227(10) Uani d . 1 . . C
H22 0.8098 0.4868 0.2571 0.027 Uiso calc R 1 . . H
Br23 1.17513(13) 0.33922(4) 0.38743(3) 0.02710(17) Uani d . 1 . . Br
C23 1.0847(12) 0.3378(4) 0.2736(3) 0.0217(10) Uani d . 1 . . C
O24 1.4033(9) 0.1624(3) 0.2758(2) 0.0287(8) Uani d . 1 . . O
H24 1.4262 0.1708 0.3255 0.034 Uiso calc R 1 . . H
C24 1.2159(11) 0.2491(4) 0.2365(3) 0.0209(10) Uani d . 1 . . C
Br25 1.33538(13) 0.13119(4) 0.09937(3) 0.02804(17) Uani d . 1 . . Br
C25 1.1513(11) 0.2491(4) 0.1521(3) 0.0207(10) Uani d . 1 . . C
C26 0.9636(11) 0.3361(4) 0.1071(3) 0.0210(10) Uani d . 1 . . C
H26 0.9212 0.3358 0.0500 0.025 Uiso calc R 1 . . H
N27 0.5009(11) 0.5912(4) 0.0657(3) 0.0327(11) Uani d . 1 . . N
C27 0.6505(12) 0.5170(4) 0.1000(3) 0.0243(11) Uani d . 1 . . C
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C11 0.027(2) 0.022(3) 0.020(2) -0.001(2) -0.0030(18) -0.0080(19)
C12 0.026(2) 0.024(3) 0.020(2) 0.000(2) -0.0070(18) -0.0025(19)
Br13 0.0399(3) 0.0331(3) 0.0167(3) 0.0045(2) -0.0087(2) -0.0093(2)
C13 0.029(2) 0.023(3) 0.019(2) -0.004(2) -0.0043(18) -0.0070(19)
O14 0.047(2) 0.027(2) 0.0227(19) 0.0064(17) -0.0078(16) -0.0115(16)
C14 0.028(3) 0.020(3) 0.022(3) 0.000(2) -0.0007(19) -0.010(2)
Br15 0.0355(3) 0.0207(3) 0.0235(3) 0.0042(2) -0.0071(2) -0.0029(2)
C15 0.025(2) 0.024(3) 0.022(2) -0.004(2) -0.0064(18) 0.002(2)
C16 0.029(2) 0.022(3) 0.017(2) -0.002(2) -0.0032(18) -0.0076(19)
N17 0.049(3) 0.027(3) 0.026(2) 0.009(2) -0.013(2) -0.009(2)
C17 0.034(3) 0.022(3) 0.022(3) 0.003(2) -0.012(2) -0.006(2)
C21 0.021(2) 0.021(3) 0.021(2) -0.0004(19) -0.0036(17) -0.0052(19)
C22 0.028(2) 0.021(3) 0.020(2) 0.000(2) -0.0002(18) -0.0093(19)
Br23 0.0360(3) 0.0303(3) 0.0166(3) -0.0001(2) -0.00651(19) -0.0078(2)
C23 0.024(2) 0.029(3) 0.013(2) -0.007(2) -0.0007(17) -0.0036(19)
O24 0.039(2) 0.026(2) 0.0206(18) 0.0079(16) -0.0116(15) -0.0072(15)
C24 0.022(2) 0.022(3) 0.020(2) -0.0031(19) -0.0022(17) -0.0031(19)
Br25 0.0358(3) 0.0261(3) 0.0231(3) 0.0066(2) -0.0054(2) -0.0114(2)
C25 0.025(2) 0.024(3) 0.015(2) -0.003(2) -0.0007(17) -0.0075(19)
C26 0.022(2) 0.028(3) 0.013(2) -0.001(2) -0.0043(17) -0.0043(19)
N27 0.042(3) 0.031(3) 0.024(2) 0.006(2) -0.0052(19) -0.008(2)
C27 0.033(3) 0.025(3) 0.015(2) 0.000(2) -0.003(2) -0.004(2)
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 C11 C12 . . 121.3(5) ?
C16 C11 C17 . . 120.5(4) ?
C12 C11 C17 . . 118.2(4) ?
C13 C12 C11 . . 118.6(5) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
C12 C13 C14 . . 121.4(5) ?
C12 C13 Br13 . . 119.6(4) ?
C14 C13 Br13 . . 118.9(4) ?
C14 O14 H14 . . 109.5 ?
O14 C14 C13 . . 123.5(4) ?
O14 C14 C15 . . 118.3(4) ?
C13 C14 C15 . . 118.2(5) ?
C16 C15 C14 . . 122.2(5) ?
C16 C15 Br15 . . 119.2(4) ?
C14 C15 Br15 . . 118.6(4) ?
C15 C16 C11 . . 118.3(4) ?
C15 C16 H16 . . 120.9 ?
C11 C16 H16 . . 120.9 ?
N17 C17 C11 . . 176.9(5) ?
C22 C21 C26 . . 121.9(4) ?
C22 C21 C27 . . 118.2(5) ?
C26 C21 C27 . . 119.9(4) ?
C23 C22 C21 . . 117.4(5) ?
C23 C22 H22 . . 121.3 ?
C21 C22 H22 . . 121.3 ?
C24 C23 C22 . . 122.6(4) ?
C24 C23 Br23 . . 118.5(4) ?
C22 C23 Br23 . . 118.8(4) ?
C24 O24 H24 . . 109.5 ?
O24 C24 C23 . . 124.4(4) ?
O24 C24 C25 . . 117.4(4) ?
C23 C24 C25 . . 118.2(4) ?
C26 C25 C24 . . 120.7(4) ?
C26 C25 Br25 . . 120.2(4) ?
C24 C25 Br25 . . 119.1(4) ?
C25 C26 C21 . . 119.1(4) ?
C25 C26 H26 . . 120.5 ?
C21 C26 H26 . . 120.5 ?
N27 C27 C21 . . 177.8(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
C11 C16 . 1.394(7) ?
C11 C12 . 1.401(7) ?
C11 C17 . 1.452(7) ?
C12 C13 . 1.381(7) ?
C12 H12 . 0.9500 ?
Br13 C13 . 1.895(5) ?
C13 C14 . 1.392(7) ?
O14 C14 . 1.355(6) ?
O14 H14 . 0.8400 ?
C14 C15 . 1.395(7) ?
Br15 C15 . 1.899(5) ?
C15 C16 . 1.375(7) ?
C16 H16 . 0.9500 ?
N17 C17 . 1.133(7) ?
C21 C22 . 1.394(7) ?
C21 C26 . 1.392(7) ?
C21 C27 . 1.453(6) ?
C22 C23 . 1.391(7) ?
C22 H22 . 0.9500 ?
Br23 C23 . 1.903(5) ?
C23 C24 . 1.385(7) ?
O24 C24 . 1.347(5) ?
O24 H24 . 0.8400 ?
C24 C25 . 1.406(6) ?
Br25 C25 . 1.880(5) ?
C25 C26 . 1.387(6) ?
C26 H26 . 0.9500 ?
N27 C27 . 1.136(6) ?