#------------------------------------------------------------------------------
#$Date: 2018-02-14 10:12:20 +0200 (Wed, 14 Feb 2018) $
#$Revision: 206435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242386.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_2242386
loop_
_publ_author_name
'Noland, Wayland E.'
'Herzig, Ryan J.'
'Engwall, Abigail J.'
'Jensen, Renee C.'
'Tritch, Kenneth J.'
_publ_section_title
;
 Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl
 3,5-dibromo-4-isocyanobenzoate
;
_journal_coeditor_code           LH5870
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              345
_journal_page_last               348
_journal_paper_doi               10.1107/S2056989018002256
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H5 Br2 N O2'
_chemical_formula_moiety         'C9 H5 Br2 N O2'
_chemical_formula_sum            'C9 H5 Br2 N O2'
_chemical_formula_weight         318.96
_chemical_melting_point          410
_chemical_name_common            RCN
_chemical_name_systematic        'Methyl 3,5-dibromo-4-cyanobenzoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 93.757(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9273(18)
_cell_length_b                   17.881(8)
_cell_length_c                   14.739(7)
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.67
_cell_volume                     1032.8(8)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.814
_diffrn_reflns_theta_min         1.793
_exptl_absorpt_coefficient_mu    7.820
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_description       Block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.518
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0274P)²+0.0295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0593
_reflns_number_gt                2013
_reflns_number_total             2426
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5870sup1.cif
_cod_data_source_block           RCN
_cod_original_cell_volume        1032.9(8)
_cod_database_code               2242386
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.189
_shelx_estimated_absorpt_t_max   0.245
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_occupancy
C C1 0.6370(6) 0.65590(14) 0.86321(17) 0.0196(5) Uani d 1
C C2 0.7731(6) 0.67398(14) 0.95078(16) 0.0199(5) Uani d 1
Br Br2 0.74408(8) 0.60384(2) 1.04534(2) 0.02954(9) Uani d 1
C C3 0.9245(6) 0.74304(14) 0.96807(17) 0.0204(5) Uani d 1
H H3A 1.0169 0.7548 1.0275 0.024 Uiso calc 1
C C4 0.9412(6) 0.79516(14) 0.89815(17) 0.0197(5) Uani d 1
C C5 0.8100(6) 0.77825(14) 0.81049(16) 0.0193(5) Uani d 1
H H5A 0.8216 0.8138 0.7629 0.023 Uiso calc 1
C C6 0.6624(6) 0.70889(15) 0.79351(16) 0.0193(5) Uani d 1
Br Br6 0.49149(7) 0.68383(2) 0.67451(2) 0.02395(9) Uani d 1
C C7 0.4695(7) 0.58481(16) 0.84529(18) 0.0251(6) Uani d 1
N N1 0.3333(6) 0.52966(14) 0.82991(16) 0.0359(6) Uani d 1
C C8 1.1066(6) 0.86917(14) 0.92064(17) 0.0203(5) Uani d 1
O O1 1.2632(5) 0.88220(11) 0.99159(14) 0.0357(5) Uani d 1
O O2 1.0590(5) 0.91760(10) 0.85308(13) 0.0292(5) Uani d 1
C C9 1.2078(8) 0.99150(15) 0.8667(2) 0.0326(7) Uani d 1
H H9A 1.1628 1.0215 0.8115 0.049 Uiso calc 1
H H9B 1.4548 0.9868 0.8798 0.049 Uiso calc 1
H H9C 1.1063 1.0161 0.9179 0.049 Uiso calc 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'
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
C2 C1 C6 118.4(2)
C2 C1 C7 120.8(2)
C6 C1 C7 120.8(2)
C3 C2 C1 120.5(2)
C3 C2 Br2 120.19(19)
C1 C2 Br2 119.32(19)
C2 C3 C4 120.0(2)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
C5 C4 C3 120.5(2)
C5 C4 C8 121.6(2)
C3 C4 C8 117.8(2)
C6 C5 C4 119.2(2)
C6 C5 H5A 120.4
C4 C5 H5A 120.4
C5 C6 C1 121.4(2)
C5 C6 Br6 119.93(19)
C1 C6 Br6 118.71(19)
N1 C7 C1 178.6(3)
O1 C8 O2 124.6(2)
O1 C8 C4 123.6(2)
O2 C8 C4 111.9(2)
C8 O2 C9 117.1(2)
O2 C9 H9A 109.5
O2 C9 H9B 109.5
H9A C9 H9B 109.5
O2 C9 H9C 109.5
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_distance
C1 C2 1.402(4)
C1 C6 1.406(4)
C1 C7 1.448(4)
C2 C3 1.387(3)
C2 Br2 1.884(3)
C3 C4 1.394(3)
C3 H3A 0.9500
C4 C5 1.393(3)
C4 C8 1.502(4)
C5 C6 1.385(4)
C5 H5A 0.9500
C6 Br6 1.890(2)
C7 N1 1.138(3)
C8 O1 1.201(3)
C8 O2 1.324(3)
O2 C9 1.454(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
C3 H3A Br6 4_676 0.95 2.97 3.878(3) 159.6
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
C6 C1 C2 C3 0.9(4)
C7 C1 C2 C3 -178.1(2)
C6 C1 C2 Br2 -179.76(18)
C7 C1 C2 Br2 1.2(3)
C1 C2 C3 C4 0.2(4)
Br2 C2 C3 C4 -179.11(18)
C2 C3 C4 C5 -0.7(4)
C2 C3 C4 C8 179.8(2)
C3 C4 C5 C6 0.0(4)
C8 C4 C5 C6 179.5(2)
C4 C5 C6 C1 1.2(4)
C4 C5 C6 Br6 -178.62(18)
C2 C1 C6 C5 -1.6(4)
C7 C1 C6 C5 177.4(2)
C2 C1 C6 Br6 178.18(18)
C7 C1 C6 Br6 -2.8(3)
C5 C4 C8 O1 -169.5(3)
C3 C4 C8 O1 10.1(4)
C5 C4 C8 O2 10.4(3)
C3 C4 C8 O2 -170.0(2)
O1 C8 O2 C9 0.0(4)
C4 C8 O2 C9 -179.9(2)

_cod_database_fobs_code 2242386
