#------------------------------------------------------------------------------
#$Date: 2018-02-14 10:12:20 +0200 (Wed, 14 Feb 2018) $
#$Revision: 206435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242387.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_2242387
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_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          391
_chemical_name_common            RNC
_chemical_name_systematic        'Methyl 3,5-dibromo-4-isocyanobenzoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90.002(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9233(9)
_cell_length_b                   13.554(3)
_cell_length_c                   18.672(4)
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.18
_cell_volume                     992.9(4)
_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 0.998
_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  0.0526
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11400
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         1.090
_exptl_absorpt_coefficient_mu    8.134
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_description       Needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.653
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0287
_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)+(0.0385P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                2132
_reflns_number_total             2277
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5870sup1.cif
_cod_data_source_block           RNC
_cod_database_code               2242387
_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   0.106
_shelx_estimated_absorpt_t_max   0.792
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 C11 0.5312(10) 0.5930(3) 0.6880(2) 0.0187(7) Uani d 1
C C12 0.6653(9) 0.5605(2) 0.6228(2) 0.0193(7) Uani d 1
Br Br12 0.85319(11) 0.43306(2) 0.61597(2) 0.02497(11) Uani d 1
C C13 0.6606(10) 0.6211(2) 0.5634(2) 0.0216(8) Uani d 1
H H13A 0.7504 0.5983 0.5192 0.026 Uiso calc 1
C C14 0.5246(10) 0.7153(2) 0.56835(19) 0.0188(8) Uani d 1
C C15 0.3900(9) 0.7501(2) 0.63284(19) 0.0185(8) Uani d 1
H H15A 0.2971 0.8147 0.6360 0.022 Uiso calc 1
C C16 0.3944(9) 0.6887(3) 0.69219(18) 0.0181(7) Uani d 1
Br Br16 0.21859(11) 0.73312(2) 0.78028(2) 0.02528(11) Uani d 1
N N11 0.5307(9) 0.5321(2) 0.74742(17) 0.0240(7) Uani d 1
C C17 0.5282(15) 0.4800(3) 0.7968(2) 0.0402(11) Uani d 1
C C18 0.5255(11) 0.7760(2) 0.5011(2) 0.0210(8) Uani d 1
O O11 0.6712(9) 0.75012(19) 0.44732(15) 0.0321(7) Uani d 1
O O12 0.3467(8) 0.85902(17) 0.50681(14) 0.0270(6) Uani d 1
C C19 0.3135(13) 0.9150(3) 0.4408(2) 0.0306(9) Uani d 1
H H19A 0.1794 0.9747 0.4498 0.046 Uiso calc 1
H H19B 0.1984 0.8745 0.4046 0.046 Uiso calc 1
H H19C 0.5404 0.9335 0.4234 0.046 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
N11 C11 C12 120.8(3)
N11 C11 C16 120.3(3)
C12 C11 C16 118.9(3)
C13 C12 C11 120.5(3)
C13 C12 Br12 119.8(3)
C11 C12 Br12 119.7(3)
C12 C13 C14 120.0(3)
C12 C13 H13A 120.0
C14 C13 H13A 120.0
C13 C14 C15 120.9(3)
C13 C14 C18 116.6(3)
C15 C14 C18 122.5(3)
C16 C15 C14 118.8(3)
C16 C15 H15A 120.6
C14 C15 H15A 120.6
C15 C16 C11 120.9(3)
C15 C16 Br16 120.2(3)
C11 C16 Br16 118.9(3)
C17 N11 C11 179.1(4)
O11 C18 O12 124.2(4)
O11 C18 C14 122.6(3)
O12 C18 C14 113.2(3)
C18 O12 C19 114.8(3)
O12 C19 H19A 109.5
O12 C19 H19B 109.5
H19A C19 H19B 109.5
O12 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 N11 1.383(5)
C11 C12 1.396(5)
C11 C16 1.407(5)
C12 C13 1.379(5)
C12 Br12 1.883(3)
C13 C14 1.387(5)
C13 H13A 0.9500
C14 C15 1.397(5)
C14 C18 1.501(5)
C15 C16 1.386(5)
C15 H15A 0.9500
C16 Br16 1.882(3)
N11 C17 1.162(5)
C18 O11 1.207(5)
C18 O12 1.331(4)
O12 C19 1.454(4)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
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
N11 C11 C12 C13 179.1(3)
C16 C11 C12 C13 -0.6(6)
N11 C11 C12 Br12 -0.8(5)
C16 C11 C12 Br12 179.5(3)
C11 C12 C13 C14 0.6(6)
Br12 C12 C13 C14 -179.5(3)
C12 C13 C14 C15 -0.3(6)
C12 C13 C14 C18 -179.3(4)
C13 C14 C15 C16 0.0(6)
C18 C14 C15 C16 179.0(3)
C14 C15 C16 C11 -0.1(6)
C14 C15 C16 Br16 179.5(3)
N11 C11 C16 C15 -179.3(4)
C12 C11 C16 C15 0.4(5)
N11 C11 C16 Br16 1.1(5)
C12 C11 C16 Br16 -179.2(3)
C13 C14 C18 O11 -8.6(6)
C15 C14 C18 O11 172.4(4)
C13 C14 C18 O12 170.5(3)
C15 C14 C18 O12 -8.5(6)
O11 C18 O12 C19 4.8(6)
C14 C18 O12 C19 -174.2(4)

_cod_database_fobs_code 2242387
