#------------------------------------------------------------------------------
#$Date: 2019-11-25 04:54:22 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/93/4129317.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_4129317
loop_
_publ_author_name
'Harada, Jun'
'Ohtani, Masaki'
'Takahashi, Yukihiro'
'Inabe, Tamotsu'
_publ_section_title
;
 Molecular motion, dielectric response, and phase transition of
 charge-transfer crystals: acquired dynamic and dielectric properties of
 polar molecules in crystals.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4477
_journal_page_last               4486
_journal_paper_doi               10.1021/jacs.5b00412
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'Br4 C8 O3, 2(C10 H6)'
_chemical_formula_sum            'C28 H12 Br4 O3'
_chemical_formula_weight         716.02
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                85.4641(13)
_cell_angle_beta                 73.8886(12)
_cell_angle_gamma                68.9570(12)
_cell_formula_units_Z            2
_cell_length_a                   9.9647(8)
_cell_length_b                   10.0419(9)
_cell_length_c                   12.5208(11)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.499
_cell_measurement_theta_min      2.174
_cell_volume                     1123.11(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2 2014.1-1 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21609
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         1.693
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.199
_exptl_absorpt_correction_T_max  0.3783
_exptl_absorpt_correction_T_min  0.1437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1273 before and 0.0409 after correction. The Ratio of minimum to maximum transmission is 0.3799. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.118
_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     316
_refine_ls_number_reflns         5150
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0220
_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)+(0.0317P)²+0.3726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4665
_reflns_number_total             5150
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b00412_si_002.cif
_cod_data_source_block           perylene_TBPA_200K
_cod_database_code               4129317
_shelxl_version_number           2014/6
_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_max   0.672
_shelx_estimated_absorpt_t_min   0.256
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.09405(2) 0.26944(2) 0.05048(2) 0.03281(6) Uani 1 1 d .
Br2 Br 0.30097(2) 0.46870(2) 0.03351(2) 0.03535(6) Uani 1 1 d .
Br3 Br 0.44599(2) 0.47207(2) 0.23717(2) 0.03745(7) Uani 1 1 d .
Br4 Br 0.41694(2) 0.25264(2) 0.44469(2) 0.03780(6) Uani 1 1 d .
O1 O 0.23663(18) 0.03498(17) 0.50214(12) 0.0414(4) Uani 1 1 d .
O2 O 0.04107(17) 0.02884(16) 0.22550(14) 0.0403(4) Uani 1 1 d .
O3 O 0.12435(15) 0.01047(14) 0.37614(12) 0.0337(3) Uani 1 1 d .
C1 C 0.2070(2) 0.0703(2) 0.41742(17) 0.0299(4) Uani 1 1 d .
C2 C 0.1032(2) 0.06880(19) 0.27485(17) 0.0295(4) Uani 1 1 d .
C3 C 0.18880(19) 0.26595(18) 0.16068(15) 0.0221(3) Uani 1 1 d .
C4 C 0.27281(19) 0.35263(18) 0.15672(15) 0.0235(4) Uani 1 1 d .
C5 C 0.33842(19) 0.35136(18) 0.24203(15) 0.0240(4) Uani 1 1 d .
C6 C 0.3249(2) 0.26148(19) 0.33231(15) 0.0234(3) Uani 1 1 d .
C7 C 0.24203(19) 0.17580(18) 0.33426(15) 0.0229(4) Uani 1 1 d .
C8 C 0.17686(19) 0.17747(18) 0.25054(15) 0.0228(3) Uani 1 1 d .
C9 C 0.6930(2) 0.1441(2) 0.01068(18) 0.0347(4) Uani 1 1 d .
H9 H 0.7205 0.2018 -0.0491 0.042 Uiso 1 1 calc R
C10 C 0.7506(2) 0.1309(2) 0.1020(2) 0.0407(5) Uani 1 1 d .
H10 H 0.8172 0.1784 0.1030 0.049 Uiso 1 1 calc R
C11 C 0.7123(2) 0.0506(2) 0.18987(19) 0.0367(5) Uani 1 1 d .
H11 H 0.7512 0.0431 0.2522 0.044 Uiso 1 1 calc R
C12 C 0.5758(2) -0.1076(2) 0.27785(17) 0.0352(5) Uani 1 1 d .
H12 H 0.6134 -0.1146 0.3408 0.042 Uiso 1 1 calc R
C13 C 0.4851(2) -0.1802(2) 0.27438(18) 0.0371(5) Uani 1 1 d .
H13 H 0.4599 -0.2380 0.3349 0.045 Uiso 1 1 calc R
C14 C 0.4288(2) -0.17031(19) 0.18221(17) 0.0313(4) Uani 1 1 d .
H14 H 0.3660 -0.2221 0.1813 0.038 Uiso 1 1 calc R
C15 C 0.59701(19) 0.07584(18) 0.00433(15) 0.0245(4) Uani 1 1 d .
C16 C 0.55709(19) -0.01040(17) 0.09477(15) 0.0232(4) Uani 1 1 d .
C17 C 0.4620(2) -0.08722(18) 0.09234(15) 0.0240(4) Uani 1 1 d .
C18 C 0.6145(2) -0.0217(2) 0.18797(16) 0.0288(4) Uani 1 1 d .
C19 C 0.1502(2) 0.6879(2) 0.51041(19) 0.0366(5) Uani 1 1 d .
H19 H 0.1612 0.7536 0.4527 0.044 Uiso 1 1 calc R
C20 C 0.2093(2) 0.6854(3) 0.5997(2) 0.0463(6) Uani 1 1 d .
H20 H 0.2591 0.7496 0.6022 0.056 Uiso 1 1 calc R
C21 C 0.1963(2) 0.5918(3) 0.6833(2) 0.0438(6) Uani 1 1 d .
H21 H 0.2372 0.5908 0.7436 0.053 Uiso 1 1 calc R
C22 C 0.1088(2) 0.3975(2) 0.76718(18) 0.0410(5) Uani 1 1 d .
H22 H 0.1492 0.3958 0.8279 0.049 Uiso 1 1 calc R
C23 C 0.0387(3) 0.3061(2) 0.76333(18) 0.0438(6) Uani 1 1 d .
H23 H 0.0305 0.2402 0.8214 0.053 Uiso 1 1 calc R
C24 C -0.0220(2) 0.3068(2) 0.67513(17) 0.0348(5) Uani 1 1 d .
H24 H -0.0703 0.2409 0.6743 0.042 Uiso 1 1 calc R
C25 C 0.0758(2) 0.59688(18) 0.50382(15) 0.0248(4) Uani 1 1 d .
C26 C 0.06118(19) 0.49816(18) 0.59119(15) 0.0238(4) Uani 1 1 d .
C27 C -0.01329(19) 0.40110(18) 0.58909(15) 0.0248(4) Uani 1 1 d .
C28 C 0.1225(2) 0.4963(2) 0.68077(17) 0.0321(4) Uani 1 1 d .
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'
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
_geom_angle_site_symmetry_3
C2 O3 C1 111.30(15) .
O1 C1 O3 121.57(18) .
O1 C1 C7 132.2(2) .
O3 C1 C7 106.22(16) .
O2 C2 O3 121.42(18) .
O2 C2 C8 132.38(19) .
O3 C2 C8 106.18(17) .
C4 C3 Br1 121.88(13) .
C8 C3 Br1 120.75(14) .
C8 C3 C4 117.38(17) .
C3 C4 Br2 119.45(14) .
C5 C4 Br2 119.82(13) .
C5 C4 C3 120.71(16) .
C4 C5 Br3 120.06(13) .
C4 C5 C6 121.10(16) .
C6 C5 Br3 118.85(14) .
C5 C6 Br4 122.05(14) .
C7 C6 Br4 120.68(14) .
C7 C6 C5 117.26(17) .
C6 C7 C1 130.27(18) .
C8 C7 C1 108.07(17) .
C8 C7 C6 121.66(16) .
C3 C8 C2 129.91(18) .
C7 C8 C2 108.18(16) .
C7 C8 C3 121.88(17) .
C10 C9 H9 119.0 .
C15 C9 H9 119.0 .
C15 C9 C10 122.0(2) .
C9 C10 H10 119.6 .
C11 C10 C9 120.7(2) .
C11 C10 H10 119.6 .
C10 C11 H11 120.1 .
C10 C11 C18 119.7(2) .
C18 C11 H11 120.1 .
C13 C12 H12 119.9 .
C13 C12 C18 120.2(2) .
C18 C12 H12 119.9 .
C12 C13 H13 119.8 .
C12 C13 C14 120.35(19) .
C14 C13 H13 119.8 .
C13 C14 H14 119.0 .
C17 C14 C13 121.9(2) .
C17 C14 H14 119.0 .
C9 C15 C16 118.21(18) .
C9 C15 C17 122.35(18) 2_655
C16 C15 C17 119.43(16) 2_655
C15 C16 C17 121.19(17) .
C18 C16 C15 119.42(17) .
C18 C16 C17 119.39(17) .
C14 C17 C15 122.26(18) 2_655
C14 C17 C16 118.36(18) .
C16 C17 C15 119.38(16) 2_655
C11 C18 C12 120.4(2) .
C11 C18 C16 119.89(19) .
C12 C18 C16 119.72(19) .
C20 C19 H19 119.2 .
C25 C19 H19 119.2 .
C25 C19 C20 121.7(2) .
C19 C20 H20 119.7 .
C21 C20 C19 120.5(2) .
C21 C20 H20 119.7 .
C20 C21 H21 119.9 .
C20 C21 C28 120.3(2) .
C28 C21 H21 119.9 .
C23 C22 H22 119.9 .
C23 C22 C28 120.2(2) .
C28 C22 H22 119.9 .
C22 C23 H23 119.5 .
C22 C23 C24 120.9(2) .
C24 C23 H23 119.5 .
C23 C24 H24 119.2 .
C27 C24 C23 121.5(2) .
C27 C24 H24 119.2 .
C19 C25 C26 118.35(19) .
C19 C25 C27 122.09(18) 2_566
C26 C25 C27 119.56(16) 2_566
C27 C26 C25 121.13(17) .
C28 C26 C25 119.31(18) .
C28 C26 C27 119.56(17) .
C24 C27 C25 122.24(18) 2_566
C24 C27 C26 118.45(19) .
C26 C27 C25 119.31(16) 2_566
C21 C28 C22 120.8(2) .
C21 C28 C26 119.9(2) .
C26 C28 C22 119.3(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.8676(18) .
Br2 C4 1.8781(17) .
Br3 C5 1.8727(18) .
Br4 C6 1.8621(19) .
O1 C1 1.174(3) .
O2 C2 1.164(3) .
O3 C1 1.396(3) .
O3 C2 1.392(2) .
C1 C7 1.489(2) .
C2 C8 1.490(3) .
C3 C4 1.398(3) .
C3 C8 1.383(2) .
C4 C5 1.396(3) .
C5 C6 1.397(3) .
C6 C7 1.385(3) .
C7 C8 1.374(3) .
C9 H9 0.9500 .
C9 C10 1.393(3) .
C9 C15 1.383(3) .
C10 H10 0.9500 .
C10 C11 1.361(3) .
C11 H11 0.9500 .
C11 C18 1.415(3) .
C12 H12 0.9500 .
C12 C13 1.360(3) .
C12 C18 1.416(3) .
C13 H13 0.9500 .
C13 C14 1.399(3) .
C14 H14 0.9500 .
C14 C17 1.384(3) .
C15 C16 1.426(3) .
C15 C17 1.466(3) 2_655
C16 C17 1.428(3) .
C16 C18 1.416(3) .
C17 C15 1.466(3) 2_655
C19 H19 0.9500 .
C19 C20 1.396(3) .
C19 C25 1.387(3) .
C20 H20 0.9500 .
C20 C21 1.361(4) .
C21 H21 0.9500 .
C21 C28 1.409(3) .
C22 H22 0.9500 .
C22 C23 1.349(4) .
C22 C28 1.421(3) .
C23 H23 0.9500 .
C23 C24 1.397(3) .
C24 H24 0.9500 .
C24 C27 1.382(3) .
C25 C26 1.430(3) .
C25 C27 1.460(3) 2_566
C26 C27 1.427(3) .
C26 C28 1.414(3) .
C27 C25 1.460(3) 2_566
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
Br1 C3 C4 Br2 -3.5(2) . .
Br1 C3 C4 C5 177.88(12) . .
Br1 C3 C8 C2 4.3(3) . .
Br1 C3 C8 C7 -178.16(13) . .
Br2 C4 C5 Br3 3.15(19) . .
Br2 C4 C5 C6 -177.16(13) . .
Br3 C5 C6 Br4 -2.6(2) . .
Br3 C5 C6 C7 178.72(12) . .
Br4 C6 C7 C1 1.3(3) . .
Br4 C6 C7 C8 -178.03(13) . .
O1 C1 C7 C6 1.9(4) . .
O1 C1 C7 C8 -178.7(2) . .
O2 C2 C8 C3 1.8(4) . .
O2 C2 C8 C7 -176.0(2) . .
O3 C1 C7 C6 -177.76(17) . .
O3 C1 C7 C8 1.67(19) . .
O3 C2 C8 C3 179.96(17) . .
O3 C2 C8 C7 2.12(19) . .
C1 O3 C2 O2 177.36(18) . .
C1 O3 C2 C8 -1.06(19) . .
C1 C7 C8 C2 -2.31(19) . .
C1 C7 C8 C3 179.65(16) . .
C2 O3 C1 O1 -179.99(18) . .
C2 O3 C1 C7 -0.30(19) . .
C3 C4 C5 Br3 -178.26(13) . .
C3 C4 C5 C6 1.4(3) . .
C4 C3 C8 C2 -176.34(17) . .
C4 C3 C8 C7 1.2(3) . .
C4 C5 C6 Br4 177.72(13) . .
C4 C5 C6 C7 -1.0(3) . .
C5 C6 C7 C1 -179.95(17) . .
C5 C6 C7 C8 0.7(3) . .
C6 C7 C8 C2 177.18(16) . .
C6 C7 C8 C3 -0.9(3) . .
C8 C3 C4 Br2 177.09(12) . .
C8 C3 C4 C5 -1.5(2) . .
C9 C10 C11 C18 0.8(3) . .
C9 C15 C16 C17 -178.17(16) . .
C9 C15 C16 C18 0.9(2) . .
C10 C9 C15 C16 -0.1(3) . .
C10 C9 C15 C17 -178.91(18) . 2_655
C10 C11 C18 C12 178.87(19) . .
C10 C11 C18 C16 0.1(3) . .
C12 C13 C14 C17 -0.2(3) . .
C13 C12 C18 C11 -178.12(19) . .
C13 C12 C18 C16 0.6(3) . .
C13 C14 C17 C15 -179.76(17) . 2_655
C13 C14 C17 C16 0.2(3) . .
C15 C9 C10 C11 -0.8(3) . .
C15 C16 C17 C14 179.28(16) . .
C15 C16 C17 C15 -0.7(3) . 2_655
C15 C16 C18 C11 -1.0(3) . .
C15 C16 C18 C12 -179.73(16) . .
C17 C15 C16 C17 0.7(3) 2_655 .
C17 C15 C16 C18 179.81(15) 2_655 .
C17 C16 C18 C11 178.14(17) . .
C17 C16 C18 C12 -0.6(2) . .
C18 C12 C13 C14 -0.2(3) . .
C18 C16 C17 C14 0.2(2) . .
C18 C16 C17 C15 -179.81(15) . 2_655
C19 C20 C21 C28 -0.2(3) . .
C19 C25 C26 C27 -179.64(16) . .
C19 C25 C26 C28 0.0(3) . .
C20 C19 C25 C26 -0.4(3) . .
C20 C19 C25 C27 179.84(18) . 2_566
C20 C21 C28 C22 179.6(2) . .
C20 C21 C28 C26 -0.2(3) . .
C22 C23 C24 C27 -0.3(3) . .
C23 C22 C28 C21 -179.6(2) . .
C23 C22 C28 C26 0.3(3) . .
C23 C24 C27 C25 179.88(17) . 2_566
C23 C24 C27 C26 0.7(3) . .
C25 C19 C20 C21 0.5(3) . .
C25 C26 C27 C24 179.06(16) . .
C25 C26 C27 C25 -0.2(3) . 2_566
C25 C26 C28 C21 0.3(3) . .
C25 C26 C28 C22 -179.54(16) . .
C27 C25 C26 C27 0.2(3) 2_566 .
C27 C25 C26 C28 179.77(15) 2_566 .
C27 C26 C28 C21 179.93(17) . .
C27 C26 C28 C22 0.1(3) . .
C28 C22 C23 C24 -0.2(3) . .
C28 C26 C27 C24 -0.5(3) . .
C28 C26 C27 C25 -179.77(15) . 2_566
