#------------------------------------------------------------------------------
#$Date: 2019-12-25 22:38:55 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245923 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/14/2311487.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_2311487
loop_
_publ_author_name
'Noland, Wayland E.'
'Rieger, Janel L.'
'Tu, Zoe H.'
'Tritch, Kenneth J.'
_publ_section_title
;
 A 2:1 co-crystal of 3,5-di-bromo-4-cyano-benzoic acid and anthracene.
;
_journal_coeditor_code           LH5854
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1743
_journal_page_last               1746
_journal_paper_doi               10.1107/S2056989017014815
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C8 H3 Br2 N O2, 0.5C14 H10'
_chemical_formula_moiety         'C8 H3 Br2 N O2, 0.5(C14 H10)'
_chemical_formula_sum            'C15 H8 Br2 N O2'
_chemical_formula_weight         394.04
_chemical_name_common            VII
_chemical_name_systematic
;
3,5-Dibromo-4-cyanobenzoic acid--anthracene (2/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                115.356(3)
_cell_angle_beta                 106.876(3)
_cell_angle_gamma                94.119(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8963(8)
_cell_length_b                   9.4701(9)
_cell_length_c                   9.5839(9)
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.60
_cell_measurement_theta_min      5.31
_cell_volume                     680.03(11)
_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
;
SHELXS97 (Sheldrick 2015a)
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON-1000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9139
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.590
_diffrn_reflns_theta_min         5.307
_exptl_absorpt_coefficient_mu    7.569
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.924
_exptl_crystal_description       plate
_exptl_crystal_F_000             382
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.531
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0264
_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)+(0.0369P)²+0.5603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0681
_reflns_number_gt                2607
_reflns_number_total             2745
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5854sup1.cif
_cod_data_source_block           I
_cod_database_code               2311487
_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   0.343
_shelx_estimated_absorpt_t_max   0.805
_shelxl_version_number           2014/6
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
Br Br1 0.38562(3) 0.12356(3) 0.93908(3) 0.01483(9) Uani d 1
Br Br2 0.81803(2) 0.51847(3) 0.84679(3) 0.01686(9) Uani d 1
O O1 0.21809(18) 0.54610(19) 0.5615(2) 0.0154(3) Uani d 1
H H1A 0.1338 0.5671 0.5146 0.023 Uiso calc 1
O O2 0.04198(18) 0.38413(18) 0.5858(2) 0.0139(3) Uani d 1
N N1 0.8230(2) 0.2641(3) 1.0526(3) 0.0211(4) Uani d 1
C C1 0.1800(3) 0.4429(2) 0.6097(3) 0.0102(4) Uani d 1
C C2 0.3217(2) 0.4018(2) 0.7011(2) 0.0092(4) Uani d 1
C C3 0.2929(2) 0.2999(2) 0.7650(2) 0.0096(4) Uani d 1
H H3A 0.1859 0.2573 0.7495 0.011 Uiso calc 1
C C4 0.4229(3) 0.2615(2) 0.8516(2) 0.0100(4) Uani d 1
C C5 0.5815(2) 0.3249(2) 0.8767(2) 0.0102(4) Uani d 1
C C6 0.7162(3) 0.2888(3) 0.9728(3) 0.0135(4) Uani d 1
C C7 0.6057(3) 0.4265(3) 0.8107(3) 0.0116(4) Uani d 1
C C8 0.4777(3) 0.4647(2) 0.7223(2) 0.0103(4) Uani d 1
H H8A 0.4958 0.5328 0.6766 0.012 Uiso calc 1
C C9 0.4142(3) 0.8993(2) 0.5372(3) 0.0131(4) Uani d 1
H H9A 0.3562 0.8307 0.5622 0.016 Uiso calc 1
C C10 0.5827(3) 0.9268(2) 0.5908(3) 0.0126(4) Uani d 1
C C11 0.6714(3) 0.8552(3) 0.6831(3) 0.0179(5) Uani d 1
H H11A 0.6149 0.7875 0.7102 0.022 Uiso calc 1
C C12 0.8344(3) 0.8823(3) 0.7326(3) 0.0230(5) Uani d 1
H H12A 0.8912 0.8345 0.7947 0.028 Uiso calc 1
C C13 0.9206(3) 0.9822(3) 0.6915(3) 0.0247(5) Uani d 1
H H13A 1.0347 0.9989 0.7249 0.030 Uiso calc 1
C C14 0.8420(3) 1.0540(3) 0.6055(3) 0.0198(5) Uani d 1
H H14A 0.9019 1.1211 0.5803 0.024 Uiso calc 1
C C15 0.6700(3) 1.0296(2) 0.5522(3) 0.0121(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C1 O1 H1A . 109.5
O2 C1 O1 . 124.6(2)
O2 C1 C2 . 121.29(19)
O1 C1 C2 . 114.08(18)
C3 C2 C8 . 121.22(19)
C3 C2 C1 . 117.98(18)
C8 C2 C1 . 120.80(19)
C4 C3 C2 . 118.88(19)
C4 C3 H3A . 120.6
C2 C3 H3A . 120.6
C3 C4 C5 . 121.09(19)
C3 C4 Br1 . 119.34(16)
C5 C4 Br1 . 119.57(15)
C7 C5 C4 . 118.42(19)
C7 C5 C6 . 121.09(19)
C4 C5 C6 . 120.47(19)
N1 C6 C5 . 178.1(2)
C8 C7 C5 . 121.37(19)
C8 C7 Br2 . 119.04(16)
C5 C7 Br2 . 119.57(16)
C7 C8 C2 . 119.02(19)
C7 C8 H8A . 120.5
C2 C8 H8A . 120.5
C15 C9 C10 2_676 121.3(2)
C15 C9 H9A 2_676 119.4
C10 C9 H9A . 119.4
C9 C10 C11 . 122.1(2)
C9 C10 C15 . 119.3(2)
C11 C10 C15 . 118.6(2)
C12 C11 C10 . 121.2(2)
C12 C11 H11A . 119.4
C10 C11 H11A . 119.4
C11 C12 C13 . 120.0(2)
C11 C12 H12A . 120.0
C13 C12 H12A . 120.0
C14 C13 C12 . 121.0(2)
C14 C13 H13A . 119.5
C12 C13 H13A . 119.5
C13 C14 C15 . 120.7(2)
C13 C14 H14A . 119.7
C15 C14 H14A . 119.7
C9 C15 C10 2_676 119.5(2)
C9 C15 C14 2_676 122.1(2)
C10 C15 C14 . 118.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C4 . 1.886(2)
Br2 C7 . 1.890(2)
O1 C1 . 1.309(3)
O1 H1A . 0.8400
O2 C1 . 1.224(3)
N1 C6 . 1.142(3)
C1 C2 . 1.493(3)
C2 C3 . 1.390(3)
C2 C8 . 1.391(3)
C3 C4 . 1.386(3)
C3 H3A . 0.9500
C4 C5 . 1.402(3)
C5 C7 . 1.394(3)
C5 C6 . 1.446(3)
C7 C8 . 1.381(3)
C8 H8A . 0.9500
C9 C15 2_676 1.394(3)
C9 C10 . 1.400(3)
C9 H9A . 0.9500
C10 C11 . 1.432(3)
C10 C15 . 1.432(3)
C11 C12 . 1.356(4)
C11 H11A . 0.9500
C12 C13 . 1.423(4)
C12 H12A . 0.9500
C13 C14 . 1.359(4)
C13 H13A . 0.9500
C14 C15 . 1.433(3)
C14 H14A . 0.9500
C15 C9 2_676 1.394(3)
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
O1 H1A O2 2_566 0.84 1.79 2.627(2) 178.4
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
O2 C1 C2 C3 . . -2.9(3)
O1 C1 C2 C3 . . 176.48(18)
O2 C1 C2 C8 . . 177.60(19)
O1 C1 C2 C8 . . -3.1(3)
C8 C2 C3 C4 . . 0.2(3)
C1 C2 C3 C4 . . -179.35(18)
C2 C3 C4 C5 . . 0.6(3)
C2 C3 C4 Br1 . . 179.97(14)
C3 C4 C5 C7 . . -0.7(3)
Br1 C4 C5 C7 . . 180.00(14)
C3 C4 C5 C6 . . 177.55(18)
Br1 C4 C5 C6 . . -1.8(3)
C4 C5 C7 C8 . . -0.1(3)
C6 C5 C7 C8 . . -178.35(19)
C4 C5 C7 Br2 . . 178.40(14)
C6 C5 C7 Br2 . . 0.2(3)
C5 C7 C8 C2 . . 1.0(3)
Br2 C7 C8 C2 . . -177.60(15)
C3 C2 C8 C7 . . -1.0(3)
C1 C2 C8 C7 . . 178.55(18)
C15 C9 C10 C11 2_676 . 179.81(19)
C15 C9 C10 C15 2_676 . -0.3(3)
C9 C10 C11 C12 . . 179.4(2)
C15 C10 C11 C12 . . -0.5(3)
C10 C11 C12 C13 . . -0.6(4)
C11 C12 C13 C14 . . 1.2(4)
C12 C13 C14 C15 . . -0.7(4)
C9 C10 C15 C9 . 2_676 0.3(3)
C11 C10 C15 C9 . 2_676 -179.81(19)
C9 C10 C15 C14 . . -178.88(19)
C11 C10 C15 C14 . . 1.0(3)
C13 C14 C15 C9 . 2_676 -179.6(2)
C13 C14 C15 C10 . . -0.4(3)
