#------------------------------------------------------------------------------
#$Date: 2016-04-01 04:37:12 +0300 (Fri, 01 Apr 2016) $
#$Revision: 180662 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/16/2241620.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_2241620
loop_
_publ_author_name
'Meany, Joseph E.'
'Gerlach, Deidra L.'
'Papish, Elizabeth T.'
'Woski, Stephen A.'
_publ_section_title
;
 Crystal structure of
 4'-bromo-2',5'-dimethoxy-2,5-dioxo-[1,1'-biphenyl]-3,4-dicarbonitrile
 [BrHBQ(CN)₂] benzene hemisolvate
;
_journal_coeditor_code           HB7567
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              600
_journal_page_last               603
_journal_paper_doi               10.1107/S2056989016005120
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C16 H9 Br N2 O4, 0.5C6 H6'
_chemical_formula_moiety         'C16 H9 Br N2 O4, 0.5(C6 H6)'
_chemical_formula_sum            'C19 H12 Br N2 O4'
_chemical_formula_weight         412.22
_chemical_name_common            FNWI-021
_chemical_name_systematic
;
4'-Bromo-2',5'-dimethoxy-2,5-dioxo-[1,1'-biphenyl]-3,4-dicarbonitrile
benzene hemisolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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           SHELXL-2014/7
_cell_angle_alpha                104.469(2)
_cell_angle_beta                 95.120(2)
_cell_angle_gamma                102.851(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0427(17)
_cell_length_b                   10.343(2)
_cell_length_c                   11.007(2)
_cell_measurement_reflns_used    5182
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.92
_cell_volume                     854.1(3)
_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.,  2006)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2015b)
SHELXLE (Hübschle et al.,  2011)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS SMART APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.632
_diffrn_reflns_theta_min         2.920
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       block
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.352
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0276
_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)+(0.0307P)²+0.3076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0676
_reflns_number_gt                3382
_reflns_number_total             3957
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7567sup1.cif
_cod_data_source_block           I
_cod_database_code               2241620
_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   0.629
_shelx_estimated_absorpt_t_max   0.868
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
C C1 0.1145(2) -0.15670(19) -0.05223(15) 0.0248(4) Uani d 1
C C2 0.2309(2) -0.02953(19) -0.02559(16) 0.0249(4) Uani d 1
H H2 0.2677 0.0071 -0.0925 0.030 Uiso calc 1
C C3 0.2939(2) 0.04468(18) 0.10043(16) 0.0240(4) Uani d 1
C C4 0.2382(2) -0.01088(18) 0.19817(15) 0.0216(3) Uani d 1
C C5 0.1153(2) -0.13776(18) 0.16872(15) 0.0219(3) Uani d 1
H H5 0.0746 -0.1731 0.2353 0.026 Uiso calc 1
C C6 0.0521(2) -0.21285(18) 0.04302(16) 0.0235(4) Uani d 1
C C7 0.3088(2) 0.06338(17) 0.33278(15) 0.0207(3) Uani d 1
C C8 0.5003(2) 0.10333(17) 0.36973(15) 0.0207(3) Uani d 1
C C9 0.5736(2) 0.19577(17) 0.50147(15) 0.0207(3) Uani d 1
C C10 0.4713(2) 0.21563(17) 0.59112(15) 0.0212(3) Uani d 1
C C11 0.2798(2) 0.15131(17) 0.55889(16) 0.0215(3) Uani d 1
C C12 0.2090(2) 0.08304(18) 0.42447(16) 0.0224(3) Uani d 1
H H12 0.0872 0.0513 0.4011 0.027 Uiso calc 1
C C13 0.4568(3) 0.2362(2) 0.04085(19) 0.0327(4) Uani d 1
H H13A 0.5171 0.1797 -0.0155 0.049 Uiso calc 1
H H13B 0.5338 0.3282 0.0801 0.049 Uiso calc 1
H H13C 0.3540 0.2445 -0.0084 0.049 Uiso calc 1
C C14 -0.1132(3) -0.4035(2) 0.10228(19) 0.0356(4) Uani d 1
H H14A -0.1932 -0.4943 0.0630 0.053 Uiso calc 1
H H14B -0.1695 -0.3463 0.1616 0.053 Uiso calc 1
H H14C -0.0097 -0.4148 0.1483 0.053 Uiso calc 1
C C15 0.5379(2) 0.29235(19) 0.72153(16) 0.0260(4) Uani d 1
C C16 0.7587(2) 0.24907(19) 0.52856(16) 0.0257(4) Uani d 1
C C17 0.3212(2) 0.45790(19) 0.48189(19) 0.0298(4) Uani d 1
H H17 0.1988 0.4292 0.4699 0.036 Uiso calc 1
C C18 0.4079(3) 0.43078(19) 0.37931(18) 0.0301(4) Uani d 1
H H18 0.3454 0.3836 0.2969 0.036 Uiso calc 1
C C19 0.5876(3) 0.4731(2) 0.39738(18) 0.0306(4) Uani d 1
H H19 0.6478 0.4547 0.3271 0.037 Uiso calc 1
N N1 0.9050(2) 0.2909(2) 0.55007(17) 0.0393(4) Uani d 1
N N2 0.5915(2) 0.35262(19) 0.82435(15) 0.0399(4) Uani d 1
O O1 -0.06536(16) -0.33788(13) 0.00550(12) 0.0311(3) Uani d 1
O O2 0.40645(18) 0.17220(13) 0.13801(12) 0.0327(3) Uani d 1
O O3 0.59685(17) 0.05565(14) 0.30356(12) 0.0308(3) Uani d 1
O O4 0.19158(16) 0.15713(14) 0.64297(12) 0.0303(3) Uani d 1
Br Br1 0.04198(3) -0.26003(2) -0.22428(2) 0.03965(8) 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 0.0000 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
C2 C1 C6 . . 122.44(15)
C2 C1 Br1 . . 118.35(13)
C6 C1 Br1 . . 119.19(13)
C1 C2 C3 . . 119.35(15)
C1 C2 H2 . . 120.3
C3 C2 H2 . . 120.3
O2 C3 C2 . . 124.46(15)
O2 C3 C4 . . 115.94(15)
C2 C3 C4 . . 119.59(16)
C5 C4 C3 . . 119.93(15)
C5 C4 C7 . . 119.47(14)
C3 C4 C7 . . 120.60(15)
C6 C5 C4 . . 120.83(15)
C6 C5 H5 . . 119.6
C4 C5 H5 . . 119.6
O1 C6 C5 . . 124.89(15)
O1 C6 C1 . . 117.32(15)
C5 C6 C1 . . 117.79(16)
C12 C7 C4 . . 123.16(15)
C12 C7 C8 . . 118.87(15)
C4 C7 C8 . . 117.58(14)
O3 C8 C7 . . 123.21(15)
O3 C8 C9 . . 118.80(15)
C7 C8 C9 . . 117.66(14)
C10 C9 C16 . . 122.54(15)
C10 C9 C8 . . 120.68(15)
C16 C9 C8 . . 116.49(14)
C9 C10 C15 . . 122.68(15)
C9 C10 C11 . . 120.23(15)
C15 C10 C11 . . 117.03(14)
O4 C11 C12 . . 123.04(16)
O4 C11 C10 . . 119.64(15)
C12 C11 C10 . . 117.32(14)
C7 C12 C11 . . 123.04(15)
C7 C12 H12 . . 118.5
C11 C12 H12 . . 118.5
O2 C13 H13A . . 109.5
O2 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
O2 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
O1 C14 H14A . . 109.5
O1 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
O1 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
N2 C15 C10 . . 179.5(2)
N1 C16 C9 . . 179.8(2)
C18 C17 C19 . 2_666 120.29(17)
C18 C17 H17 . . 119.9
C19 C17 H17 2_666 . 119.9
C17 C18 C19 . . 119.66(17)
C17 C18 H18 . . 120.2
C19 C18 H18 . . 120.2
C17 C19 C18 2_666 . 120.05(18)
C17 C19 H19 2_666 . 120.0
C18 C19 H19 . . 120.0
C6 O1 C14 . . 117.33(14)
C3 O2 C13 . . 117.42(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.379(3)
C1 C6 . 1.399(2)
C1 Br1 . 1.8928(17)
C2 C3 . 1.393(2)
C2 H2 . 0.9500
C3 O2 . 1.364(2)
C3 C4 . 1.403(2)
C4 C5 . 1.399(2)
C4 C7 . 1.482(2)
C5 C6 . 1.392(2)
C5 H5 . 0.9500
C6 O1 . 1.362(2)
C7 C12 . 1.349(2)
C7 C8 . 1.493(2)
C8 O3 . 1.212(2)
C8 C9 . 1.506(2)
C9 C10 . 1.346(2)
C9 C16 . 1.443(2)
C10 C15 . 1.443(2)
C10 C11 . 1.506(2)
C11 O4 . 1.213(2)
C11 C12 . 1.470(2)
C12 H12 . 0.9500
C13 O2 . 1.434(2)
C13 H13A . 0.9800
C13 H13B . 0.9800
C13 H13C . 0.9800
C14 O1 . 1.436(2)
C14 H14A . 0.9800
C14 H14B . 0.9800
C14 H14C . 0.9800
C15 N2 . 1.138(2)
C16 N1 . 1.141(2)
C17 C18 . 1.382(3)
C17 C19 2_666 1.390(3)
C17 H17 . 0.9500
C18 C19 . 1.394(3)
C18 H18 . 0.9500
C19 C17 2_666 1.390(3)
C19 H19 . 0.9500
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_4
_geom_torsion
C6 C1 C2 C3 . . 2.2(3)
Br1 C1 C2 C3 . . -176.22(13)
C1 C2 C3 O2 . . -178.67(17)
C1 C2 C3 C4 . . 0.0(3)
O2 C3 C4 C5 . . 176.45(16)
C2 C3 C4 C5 . . -2.3(3)
O2 C3 C4 C7 . . -3.8(2)
C2 C3 C4 C7 . . 177.44(16)
C3 C4 C5 C6 . . 2.5(3)
C7 C4 C5 C6 . . -177.20(15)
C4 C5 C6 O1 . . 178.97(16)
C4 C5 C6 C1 . . -0.4(3)
C2 C1 C6 O1 . . 178.57(16)
Br1 C1 C6 O1 . . -3.0(2)
C2 C1 C6 C5 . . -2.0(3)
Br1 C1 C6 C5 . . 176.44(12)
C5 C4 C7 C12 . . -47.4(2)
C3 C4 C7 C12 . . 132.83(18)
C5 C4 C7 C8 . . 125.34(17)
C3 C4 C7 C8 . . -54.4(2)
C12 C7 C8 O3 . . 158.02(17)
C4 C7 C8 O3 . . -15.1(2)
C12 C7 C8 C9 . . -15.3(2)
C4 C7 C8 C9 . . 171.61(14)
O3 C8 C9 C10 . . -158.87(16)
C7 C8 C9 C10 . . 14.8(2)
O3 C8 C9 C16 . . 15.1(2)
C7 C8 C9 C16 . . -171.25(14)
C16 C9 C10 C15 . . 0.3(3)
C8 C9 C10 C15 . . 173.92(15)
C16 C9 C10 C11 . . -176.80(15)
C8 C9 C10 C11 . . -3.2(2)
C9 C10 C11 O4 . . 171.98(16)
C15 C10 C11 O4 . . -5.3(2)
C9 C10 C11 C12 . . -7.8(2)
C15 C10 C11 C12 . . 174.96(15)
C4 C7 C12 C11 . . 177.18(15)
C8 C7 C12 C11 . . 4.5(2)
O4 C11 C12 C7 . . -172.59(17)
C10 C11 C12 C7 . . 7.1(2)
C19 C17 C18 C19 2_666 . 0.0(3)
C17 C18 C19 C17 . 2_666 0.0(3)
C5 C6 O1 C14 . . -7.0(3)
C1 C6 O1 C14 . . 172.39(16)
C2 C3 O2 C13 . . 2.9(3)
C4 C3 O2 C13 . . -175.80(16)

_cod_database_fobs_code 2241620
