#------------------------------------------------------------------------------
#$Date: 2018-02-14 10:11:25 +0200 (Wed, 14 Feb 2018) $
#$Revision: 206432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/23/2242383.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_2242383
loop_
_publ_author_name
'Lastovickova, Dominika N.'
'La Scala, John J.'
'Sausa, Rosario C.'
_publ_section_title
;
 Synthesis and crystal structures of
 (2E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione and
 (2E)-1,4-bis(4-bromophenyl)but-2-ene-1,4-dione
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              352
_journal_page_last               356
_journal_paper_doi               10.1107/S205698901800230X
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C16 H10 Br2 O2'
_chemical_formula_moiety         'C16 H10 Br2 O2'
_chemical_formula_sum            'C16 H10 Br2 O2'
_chemical_formula_weight         394.06
_chemical_name_systematic
;
(2E)-1,4-Bis(4-bromophenyl)but-2-ene-1,4-dione
;
_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
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.827(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.4391(7)
_cell_length_b                   3.9937(2)
_cell_length_c                   12.7244(7)
_cell_measurement_reflns_used    2527
_cell_measurement_temperature    298.00(10)
_cell_measurement_theta_max      26.2050
_cell_measurement_theta_min      2.8490
_cell_volume                     726.92(7)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298.00(10)
_diffrn_detector_area_resol_mean 8.0945
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dualflex, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6231
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.848
_exptl_absorpt_coefficient_mu    5.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Bourhis et al.,  2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_description       irregular
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.430
_refine_ls_extinction_coef       0.0047(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2016/4 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0292
_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)+(0.0234P)²+0.4382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0650
_reflns_number_gt                1228
_reflns_number_total             1470
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2724sup1.cif
_cod_data_source_block           2
_cod_database_code               2242383
_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.
;
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
Br Br1 0.06905(2) 0.86344(8) 0.66837(3) 0.05337(16) Uani d 1
C C1 0.31059(19) 0.3876(7) 0.5110(2) 0.0355(6) Uani d 1
C C2 0.3212(2) 0.4543(8) 0.6188(2) 0.0444(7) Uani d 1
H H2 0.377230 0.400535 0.660470 0.053 Uiso calc 1
C C3 0.2503(2) 0.5990(8) 0.6653(2) 0.0471(8) Uani d 1
H H3 0.258517 0.646056 0.737543 0.057 Uiso calc 1
C C4 0.1673(2) 0.6726(6) 0.6034(2) 0.0391(7) Uani d 1
C C5 0.1538(2) 0.6073(7) 0.4962(2) 0.0463(7) Uani d 1
H H5 0.097052 0.657253 0.455312 0.056 Uiso calc 1
C C6 0.2258(2) 0.4666(8) 0.4507(2) 0.0422(7) Uani d 1
H H6 0.217497 0.423632 0.378154 0.051 Uiso calc 1
C C7 0.3859(2) 0.2399(8) 0.4570(2) 0.0418(7) Uani d 1
C C8 0.4672(2) 0.0760(7) 0.5218(2) 0.0410(7) Uani d 1
H H8 0.471561 0.081856 0.595399 0.049 Uiso calc 1
O O1 0.38162(17) 0.2478(7) 0.36132(17) 0.0665(7) 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'
Br Br -0.2901 2.4595 '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'
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
C2 C1 C6 . 118.3(3)
C2 C1 C7 . 123.1(3)
C6 C1 C7 . 118.7(3)
C1 C2 H2 . 119.4
C3 C2 C1 . 121.2(3)
C3 C2 H2 . 119.4
C2 C3 H3 . 120.5
C4 C3 C2 . 119.0(3)
C4 C3 H3 . 120.5
C3 C4 Br1 . 118.8(2)
C3 C4 C5 . 121.5(3)
C5 C4 Br1 . 119.7(2)
C4 C5 H5 . 120.6
C4 C5 C6 . 118.8(3)
C6 C5 H5 . 120.6
C1 C6 H6 . 119.4
C5 C6 C1 . 121.3(3)
C5 C6 H6 . 119.4
C1 C7 C8 . 119.3(2)
O1 C7 C1 . 121.0(3)
O1 C7 C8 . 119.7(3)
C7 C8 H8 . 119.0
C8 C8 C7 3_656 121.9(4)
C8 C8 H8 3_656 119.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C4 . 1.896(3)
C1 C2 . 1.385(4)
C1 C6 . 1.390(4)
C1 C7 . 1.485(4)
C2 H2 . 0.9300
C2 C3 . 1.378(4)
C3 H3 . 0.9300
C3 C4 . 1.374(4)
C4 C5 . 1.376(4)
C5 H5 . 0.9300
C5 C6 . 1.377(4)
C6 H6 . 0.9300
C7 C8 . 1.492(4)
C7 O1 . 1.211(3)
C8 C8 3_656 1.310(5)
C8 H8 . 0.9300
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_4
_geom_torsion
Br1 C4 C5 C6 . -179.6(2)
C1 C2 C3 C4 . 1.0(5)
C1 C7 C8 C8 3_656 175.8(3)
C2 C1 C6 C5 . -0.1(4)
C2 C1 C7 C8 . 16.0(4)
C2 C1 C7 O1 . -164.7(3)
C2 C3 C4 Br1 . 178.8(2)
C2 C3 C4 C5 . -0.5(5)
C3 C4 C5 C6 . -0.4(5)
C4 C5 C6 C1 . 0.6(5)
C6 C1 C2 C3 . -0.8(5)
C6 C1 C7 C8 . -164.8(3)
C6 C1 C7 O1 . 14.5(4)
C7 C1 C2 C3 . 178.4(3)
C7 C1 C6 C5 . -179.3(3)
O1 C7 C8 C8 3_656 -3.5(6)

_cod_database_fobs_code 2242383
