#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/72/2227277.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_2227277
loop_
_publ_author_name
'Black, Harrison M.'
'Baughman, Russell G.'
_publ_section_title
;
 1-(4-Bromo-3-chlorophenyl)-3-methoxy-3-methylurea (chlorbromuron)
;
_journal_coeditor_code           BV2148
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2221
_journal_paper_doi               10.1107/S1600536810030606
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H10 Br Cl N2 O2'
_chemical_formula_moiety         'C9 H10 Br Cl N2 O2'
_chemical_formula_sum            'C9 H10 Br Cl N2 O2'
_chemical_formula_weight         293.55
_chemical_name_common            Chlorbromuron
_chemical_name_systematic
;
1-(4-Bromo-3-chlorophenyl)-3-methoxy-3-methylurea
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3872(7)
_cell_length_b                   9.5037(5)
_cell_length_c                   21.512(2)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      15.8
_cell_measurement_theta_min      10.0
_cell_volume                     2328.0(3)
_computing_cell_refinement
;
XSCANS (Bruker, 1996)
;
_computing_data_collection
;
XSCANS (Bruker, 1996)
;
_computing_data_reduction        'XSCANS (Bruker, 1996)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL/PC (Sheldrick, 2008) and SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Bruker P4 diffractometer'
_diffrn_measurement_method       Ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2643
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        1.3
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.743
_exptl_absorpt_correction_T_max  0.331
_exptl_absorpt_correction_T_min  0.224
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(XSHELL; Bruker, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular prism'
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.633
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0647
_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)+(0.1011P)²+0.0100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1727
_reflns_number_gt                1230
_reflns_number_total             2017
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2148.cif
_cod_data_source_block           I
_cod_database_code               2227277
_cod_database_fobs_code          2227277
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.99321(6) 0.13975(8) 0.40066(3) 0.0648(4) Uani d . 1 . .
Cl Cl1 0.75978(19) -0.0374(2) 0.44369(7) 0.0690(6) Uani d . 1 . .
O O1 0.6655(4) 0.0148(4) 0.6675(2) 0.0571(12) Uani d . 1 . .
O O2 0.6463(4) 0.3363(4) 0.7430(2) 0.0560(12) Uani d . 1 . .
N N1 0.7597(4) 0.2249(5) 0.6520(2) 0.0424(12) Uani d . 1 . .
H H1 0.7741 0.3050 0.6690 0.051 Uiso d R 1 . .
N N2 0.6419(5) 0.1877(5) 0.7384(2) 0.0501(14) Uani d . 1 . .
C C1 0.8124(5) 0.1972(6) 0.5945(3) 0.0389(14) Uani d . 1 . .
C C2 0.7677(6) 0.1002(6) 0.5513(3) 0.0449(15) Uani d . 1 . .
H H2 0.7011 0.0479 0.5609 0.054 Uiso d R 1 . .
C C3 0.8216(5) 0.0839(6) 0.4948(3) 0.0457(15) Uani d . 1 . .
C C4 0.9200(5) 0.1589(6) 0.4788(3) 0.0443(15) Uani d . 1 . .
C C5 0.9659(5) 0.2525(7) 0.5221(3) 0.0506(17) Uani d . 1 . .
H H5 1.0328 0.3040 0.5121 0.061 Uiso d R 1 . .
C C6 0.9133(6) 0.2707(6) 0.5784(3) 0.0466(15) Uani d . 1 . .
H H6 0.9457 0.3331 0.6070 0.056 Uiso d R 1 . .
C C7 0.6870(6) 0.1363(7) 0.6830(3) 0.0429(15) Uani d . 1 . .
C C8 0.5314(7) 0.1313(8) 0.7610(4) 0.074(2) Uani d . 1 . .
H H8A 0.5320 0.0306 0.7571 0.111 Uiso d R 1 . .
H H8B 0.5204 0.1565 0.8038 0.111 Uiso d R 1 . .
H H8C 0.4684 0.1693 0.7366 0.111 Uiso d R 1 . .
C C9 0.7083(8) 0.3723(8) 0.7985(3) 0.079(2) Uani d . 1 . .
H H9A 0.7121 0.4729 0.8023 0.118 Uiso d R 1 . .
H H9B 0.6691 0.3336 0.8341 0.118 Uiso d R 1 . .
H H9C 0.7864 0.3348 0.7960 0.118 Uiso d R 1 . .
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
Br1 0.0657(5) 0.0802(6) 0.0485(5) 0.0019(4) 0.0147(4) 0.0053(4)
Cl1 0.0940(14) 0.0718(12) 0.0412(9) -0.0225(10) 0.0052(10) -0.0125(9)
O1 0.084(3) 0.038(3) 0.049(3) -0.006(2) 0.007(3) -0.005(2)
O2 0.071(3) 0.047(2) 0.051(3) 0.007(2) 0.003(2) -0.013(2)
N1 0.049(3) 0.037(3) 0.041(3) 0.003(2) -0.001(3) -0.008(2)
N2 0.065(4) 0.042(3) 0.043(3) 0.006(3) 0.009(3) -0.007(2)
C1 0.043(3) 0.033(3) 0.041(3) 0.008(3) -0.001(3) 0.000(3)
C2 0.051(4) 0.042(3) 0.042(3) -0.002(3) 0.005(3) 0.005(3)
C3 0.053(4) 0.043(3) 0.041(4) 0.000(3) -0.002(3) 0.001(3)
C4 0.041(4) 0.051(4) 0.040(3) 0.009(3) 0.005(3) 0.002(3)
C5 0.039(3) 0.047(4) 0.065(5) -0.006(3) 0.000(3) 0.009(3)
C6 0.050(4) 0.046(4) 0.045(4) -0.003(3) -0.003(3) -0.002(3)
C7 0.052(4) 0.042(4) 0.035(3) 0.007(3) -0.004(3) 0.000(3)
C8 0.077(5) 0.074(5) 0.070(5) -0.009(4) 0.024(4) -0.009(4)
C9 0.094(6) 0.088(6) 0.054(5) -0.018(5) 0.003(4) -0.023(4)
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'
Cl Cl 0.1484 0.1585 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 2 2
0 2 6
-2 0 7
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
N2 O2 C9 . . 108.4(5) ?
C7 N1 C1 . . 125.4(5) y
C7 N1 H1 . . 117.2 y
C1 N1 H1 . . 117.4 y
C7 N2 O2 . . 113.5(5) y
C7 N2 C8 . . 118.6(6) y
O2 N2 C8 . . 112.0(5) y
C6 C1 N1 . . 118.7(5) ?
C6 C1 C2 . . 117.8(6) ?
N1 C1 C2 . . 123.5(5) ?
C3 C2 C1 . . 119.9(6) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.0 ?
C4 C3 C2 . . 121.9(6) ?
C4 C3 Cl1 . . 121.1(5) ?
C2 C3 Cl1 . . 117.0(5) ?
C3 C4 C5 . . 118.1(6) ?
C3 C4 Br1 . . 122.3(5) ?
C5 C4 Br1 . . 119.6(5) ?
C6 C5 C4 . . 120.8(6) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C1 . . 121.4(6) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.0 ?
O1 C7 N1 . . 124.9(5) ?
O1 C7 N2 . . 119.5(6) ?
N1 C7 N2 . . 115.4(5) ?
N2 C8 H8A . . 109.4 ?
N2 C8 H8B . . 110.0 ?
H8A C8 H8B . . 109.5 ?
N2 C8 H8C . . 109.0 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O2 C9 H9A . . 109.4 ?
O2 C9 H9B . . 110.2 ?
H9A C9 H9B . . 109.5 ?
O2 C9 H9C . . 108.8 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 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 C4 . 1.885(6) y
Cl1 C3 . 1.741(6) y
O1 C7 . 1.227(7) y
O2 N2 . 1.417(6) y
O2 C9 . 1.428(8) ?
N1 C7 . 1.356(8) ?
N1 C1 . 1.401(7) ?
N1 H1 . 0.8602 ?
N2 C7 . 1.385(7) ?
N2 C8 . 1.452(9) ?
C1 C6 . 1.388(8) ?
C1 C2 . 1.404(8) ?
C2 C3 . 1.372(8) ?
C2 H2 . 0.9303 ?
C3 C4 . 1.372(9) ?
C4 C5 . 1.390(9) ?
C5 C6 . 1.363(9) ?
C5 H5 . 0.9302 ?
C6 H6 . 0.9302 ?
C8 H8A . 0.9604 ?
C8 H8B . 0.9599 ?
C8 H8C . 0.9601 ?
C9 H9A . 0.9605 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9602 ?
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
N1 H1 O1 8_765 0.86 2.11 2.902(7) 153
N1 H1 O2 . 0.86 2.18 2.573(6) 108
C2 H2 O1 . 0.93 2.35 2.873(7) 115
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
C9 O2 N2 C7 . . . . -124.6(6) y
C9 O2 N2 C8 . . . . 97.8(7) y
C7 N1 C1 C6 . . . . -157.8(6) ?
C7 N1 C1 C2 . . . . 23.3(9) y
C6 C1 C2 C3 . . . . -1.8(9) ?
N1 C1 C2 C3 . . . . 177.0(5) ?
C1 C2 C3 C4 . . . . 0.7(9) ?
C1 C2 C3 Cl1 . . . . -179.4(5) ?
C2 C3 C4 C5 . . . . 0.8(9) ?
Cl1 C3 C4 C5 . . . . -179.1(5) ?
C2 C3 C4 Br1 . . . . -178.8(5) ?
Cl1 C3 C4 Br1 . . . . 1.3(8) ?
C3 C4 C5 C6 . . . . -1.1(9) ?
Br1 C4 C5 C6 . . . . 178.5(5) ?
C4 C5 C6 C1 . . . . -0.1(9) ?
N1 C1 C6 C5 . . . . -177.4(5) ?
C2 C1 C6 C5 . . . . 1.6(9) ?
C1 N1 C7 O1 . . . . 6.7(10) ?
C1 N1 C7 N2 . . . . -178.0(5) ?
O2 N2 C7 O1 . . . . -164.2(5) ?
C8 N2 C7 O1 . . . . -29.6(9) ?
O2 N2 C7 N1 . . . . 20.2(7) y
C8 N2 C7 N1 . . . . 154.8(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24141
