#------------------------------------------------------------------------------
#$Date: 2016-03-04 10:32:26 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177337 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/26/1542688.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1542688
loop_
_publ_author_name
'Kumar, Yogendra'
'Kumar, Sharvan'
'Kumar Keshri, Sudhir'
'Shukla, Jyoti'
'Singh, Shiv Shankar'
'Thakur, Tejender S.'
'Denti, Mitchell'
'Facchetti, Antonio'
'Mukhopadhyay, Pritam'
_publ_section_title
;
 Synthesis of Octabromoperylene Dianhydride and Diimides: Evidence of
 Halogen Bonding and Semiconducting Properties.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              472
_journal_page_last               475
_journal_paper_doi               10.1021/acs.orglett.5b03513
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C24 Br8 O6, 2(C4 H8 O)'
_chemical_formula_sum            'C32 H16 Br8 O8'
_chemical_formula_weight         1167.73
_chemical_name_common            'Octa-bromo Perylenecarboxylicdianhydride'
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 128.249(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0972(18)
_cell_length_b                   15.0686(13)
_cell_length_c                   14.2085(12)
_cell_measurement_reflns_used    5431
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.46
_cell_volume                     3547.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_laue_measured_fraction_full 0.994
_diffrn_reflns_laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17752
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.194
_diffrn_reflns_theta_min         2.459
_exptl_absorpt_coefficient_mu    9.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_description       'rectangular - block'
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.635
_exptl_transmission_factor_min   0.422
_platon_squeeze_details
;
 ?
;
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0389
_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)+(0.1000P)²+0.4423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2245
_reflns_number_total             3174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b03513_si_002.cif
_cod_data_source_block           YK4_0m_a
_cod_database_code               1542688
_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   0.342
_shelx_estimated_absorpt_t_max   0.659
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br2 Br 0.44224(4) 0.32942(4) 0.29020(6) 0.0159(2) Uani 1 1 d . .
Br1 Br 0.57266(4) 0.31950(4) 0.57924(6) 0.0203(2) Uani 1 1 d . .
Br3 Br 0.59034(4) 0.82006(4) 0.28669(6) 0.0203(2) Uani 1 1 d . .
Br4 Br 0.71666(4) 0.82367(4) 0.57454(6) 0.0231(2) Uani 1 1 d . .
O1 O 0.6604(3) 0.4557(3) 0.7621(4) 0.0296(12) Uani 1 1 d . .
O3 O 0.7217(2) 0.5677(3) 0.7526(4) 0.0238(11) Uani 1 1 d . .
C11 C 0.6098(3) 0.5738(4) 0.5019(5) 0.0143(14) Uani 1 1 d . .
C6 C 0.5376(3) 0.6553(4) 0.3134(6) 0.0138(14) Uani 1 1 d . .
C12 C 0.5550(3) 0.5747(4) 0.3773(5) 0.0139(14) Uani 1 1 d . .
O2 O 0.7664(4) 0.6998(4) 0.7617(5) 0.061(2) Uani 1 1 d . .
C8 C 0.6501(3) 0.7230(4) 0.4994(5) 0.0150(14) Uani 1 1 d . .
C7 C 0.5899(3) 0.7257(4) 0.3735(5) 0.0133(14) Uani 1 1 d . .
O7 O 0.3410(3) 0.1830(3) 0.1465(5) 0.0424(15) Uani 1 1 d . .
C9 C 0.6572(3) 0.6495(4) 0.5646(5) 0.0147(14) Uani 1 1 d . .
C1 C 0.6649(4) 0.5015(4) 0.6976(6) 0.0208(15) Uani 1 1 d . .
C5 C 0.5180(3) 0.4940(4) 0.3127(5) 0.0138(14) Uani 1 1 d . .
C4 C 0.5173(3) 0.4231(4) 0.3752(6) 0.0149(14) Uani 1 1 d . .
C3 C 0.5673(3) 0.4248(4) 0.5015(5) 0.0164(14) Uani 1 1 d . .
C2 C 0.6137(3) 0.4975(4) 0.5646(5) 0.0157(15) Uani 1 1 d . .
C10 C 0.7196(4) 0.6449(5) 0.6975(6) 0.0250(17) Uani 1 1 d . .
C14 C 0.3518(4) 0.0549(5) 0.0628(6) 0.0299(18) Uani 1 1 d . .
H3 H 0.3986 0.0205 0.1292 0.036 Uiso 1 1 calc R U
H4 H 0.3383 0.0348 -0.0141 0.036 Uiso 1 1 calc R U
C15 C 0.2788(4) 0.0453(5) 0.0622(7) 0.036(2) Uani 1 1 d . .
H6 H 0.2297 0.0283 -0.0183 0.043 Uiso 1 1 calc R U
H5 H 0.2894 0.0002 0.1210 0.043 Uiso 1 1 calc R U
C13 C 0.3687(5) 0.1531(5) 0.0805(8) 0.043(2) Uani 1 1 d . .
H1 H 0.4271 0.1647 0.1265 0.052 Uiso 1 1 calc R U
H2 H 0.3390 0.1839 0.0023 0.052 Uiso 1 1 calc R U
C16 C 0.2694(5) 0.1361(5) 0.0966(9) 0.051(3) Uani 1 1 d . .
H8 H 0.2234 0.1675 0.0249 0.062 Uiso 1 1 calc R U
H7 H 0.2591 0.1309 0.1554 0.062 Uiso 1 1 calc R U
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'
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'
H H 0.0000 0.0000 '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
_geom_angle_site_symmetry_3
C1 O3 C10 125.2(5) .
C12 C11 C9 120.1(6) .
C12 C11 C2 118.9(6) .
C9 C11 C2 120.9(6) .
C7 C6 C12 118.0(5) .
C7 C6 C6 126.4(4) 2_655
C12 C6 C6 115.6(4) 2_655
C11 C12 C6 120.2(6) .
C11 C12 C5 120.2(5) .
C6 C12 C5 119.6(5) .
C9 C8 C7 120.4(5) .
C9 C8 Br4 121.8(5) .
C7 C8 Br4 117.7(4) .
C6 C7 C8 120.6(5) .
C6 C7 Br3 120.0(5) .
C8 C7 Br3 118.9(4) .
C16 O7 C13 104.8(6) .
C8 C9 C11 118.7(6) .
C8 C9 C10 121.8(6) .
C11 C9 C10 119.2(6) .
O1 C1 O3 116.0(6) .
O1 C1 C2 127.6(6) .
O3 C1 C2 116.4(6) .
C4 C5 C12 117.4(6) .
C4 C5 C5 125.6(4) 2_655
C12 C5 C5 117.0(4) 2_655
C5 C4 C3 120.0(5) .
C5 C4 Br2 119.9(5) .
C3 C4 Br2 119.8(4) .
C2 C3 C4 121.1(5) .
C2 C3 Br1 121.8(5) .
C4 C3 Br1 117.0(4) .
C3 C2 C11 119.6(6) .
C3 C2 C1 121.8(6) .
C11 C2 C1 118.5(5) .
O2 C10 O3 115.8(6) .
O2 C10 C9 127.6(7) .
O3 C10 C9 116.6(6) .
C13 C14 C15 103.0(6) .
C13 C14 H3 111.2 .
C15 C14 H3 111.2 .
C13 C14 H4 111.2 .
C15 C14 H4 111.2 .
H3 C14 H4 109.1 .
C16 C15 C14 104.2(6) .
C16 C15 H6 110.9 .
C14 C15 H6 110.9 .
C16 C15 H5 110.9 .
C14 C15 H5 110.9 .
H6 C15 H5 108.9 .
O7 C13 C14 105.3(6) .
O7 C13 H1 110.7 .
C14 C13 H1 110.7 .
O7 C13 H2 110.7 .
C14 C13 H2 110.7 .
H1 C13 H2 108.8 .
O7 C16 C15 107.9(6) .
O7 C16 H8 110.1 .
C15 C16 H8 110.1 .
O7 C16 H7 110.1 .
C15 C16 H7 110.1 .
H8 C16 H7 108.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br2 C4 1.894(5) .
Br1 C3 1.897(6) .
Br3 C7 1.887(6) .
Br4 C8 1.885(6) .
O1 C1 1.198(8) .
O3 C1 1.372(7) .
O3 C10 1.388(8) .
C11 C12 1.391(8) .
C11 C9 1.411(8) .
C11 C2 1.425(9) .
C6 C7 1.380(8) .
C6 C12 1.423(8) .
C6 C6 1.491(12) 2_655
C12 C5 1.429(8) .
O2 C10 1.172(8) .
C8 C9 1.393(9) .
C8 C7 1.415(8) .
O7 C16 1.398(8) .
O7 C13 1.451(9) .
C9 C10 1.492(8) .
C1 C2 1.488(9) .
C5 C4 1.395(8) .
C5 C5 1.442(12) 2_655
C4 C3 1.410(8) .
C3 C2 1.370(8) .
C14 C13 1.507(10) .
C14 C15 1.541(10) .
C14 H3 0.9900 .
C14 H4 0.9900 .
C15 C16 1.505(10) .
C15 H6 0.9900 .
C15 H5 0.9900 .
C13 H1 0.9900 .
C13 H2 0.9900 .
C16 H8 0.9900 .
C16 H7 0.9900 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.000 128 40 ' '
2 1.000 0.500 0.000 128 40 ' '
3 0.500 0.000 0.500 128 40 ' '
4 1.000 0.500 0.500 128 40 ' '
