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#$Date: 2019-11-25 04:54:22 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/93/4129314.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_4129314
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, C20 H12'
_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                66.7020(10)
_cell_angle_beta                 84.4390(10)
_cell_angle_gamma                73.0640(10)
_cell_formula_units_Z            1
_cell_length_a                   7.7233(3)
_cell_length_b                   9.1834(3)
_cell_length_c                   9.1909(3)
_cell_measurement_reflns_used    7107
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.418
_cell_measurement_theta_min      2.413
_cell_volume                     572.63(3)
_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      300
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            11086
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.060
_exptl_absorpt_correction_T_max  0.2200
_exptl_absorpt_correction_T_min  0.0692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1078 before and 0.0423 after correction. The Ratio of minimum to maximum transmission is 0.3145. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.076
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.922
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     123
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0494
_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)+(0.0780P)²+1.0381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2303
_reflns_number_total             2586
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b00412_si_002.cif
_cod_data_source_block           perylene_TBPA_300K
_cod_database_code               4129314
_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   0.363
_shelx_estimated_absorpt_t_min   0.126
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 O3, O1, O2, Br1, Br2, Br3, Br4, C1, C2, C3, C4, C5, C6, C7, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: O3(0.5) O1(0.5) O2(0.5) Br1(0.5) Br2(0.5) Br3(0.5) Br4(0.5)
 C1(0.5) C2(0.5) C3(0.5) C4(0.5) C5(0.5) C6(0.5) C7(0.5) C8(0.5)
4.a Free rotating group:
 O3(O1,O2,Br1,Br2,Br3,Br4,C1,C2,C3,C4,C5,C6,C7,C8)
4.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.4059(4) 0.86883(12) 0.5059(2) 0.079(2) Uani 0.5 1 d . U P A -1
O1 O 0.5490(4) 0.72888(15) 0.74287(19) 0.069(2) Uani 0.5 1 d G U P A -1
O2 O 0.2773(4) 0.93774(11) 0.2719(2) 0.056(2) Uani 0.5 1 d G U P A -1
Br1 Br 0.3274(3) 0.64840(13) 0.14454(14) 0.0925(11) Uani 0.5 1 d G U P A -1
Br2 Br 0.48776(14) 0.24370(12) 0.32749(10) 0.0621(4) Uani 0.5 1 d G U P A -1
Br3 Br 0.68665(12) 0.09008(10) 0.67521(10) 0.0643(4) Uani 0.5 1 d G U P A -1
Br4 Br 0.6878(2) 0.33321(14) 0.85876(11) 0.0606(5) Uani 0.5 1 d G U P A -1
C1 C 0.4994(4) 0.72538(12) 0.62787(18) 0.055(2) Uani 0.5 1 d G U P A -1
C2 C 0.3611(4) 0.83433(11) 0.38222(19) 0.057(2) Uani 0.5 1 d G U P A -1
C3 C 0.4290(2) 0.55465(10) 0.34855(13) 0.043(2) Uani 0.5 1 d G U P A -1
C4 C 0.50255(17) 0.38438(10) 0.42577(10) 0.042(2) Uani 0.5 1 d G U P A -1
C5 C 0.58305(15) 0.31796(10) 0.57618(10) 0.0399(19) Uani 0.5 1 d G U P A -1
C6 C 0.5889(2) 0.41897(11) 0.65512(11) 0.042(2) Uani 0.5 1 d G U P A -1
C7 C 0.5142(3) 0.58717(11) 0.57697(14) 0.042(2) Uani 0.5 1 d G U P A -1
C8 C 0.4357(3) 0.65268(10) 0.42862(15) 0.045(2) Uani 0.5 1 d G U P A -1
C9 C 0.8359(8) 0.8327(6) 0.3147(8) 0.0744(15) Uani 1 1 d . . . . .
H9 H 0.8315 0.9140 0.3522 0.089 Uiso 1 1 calc R . . . .
C10 C 0.7601(10) 0.8791(8) 0.1647(9) 0.095(2) Uani 1 1 d . . . . .
H10 H 0.7094 0.9902 0.1039 0.114 Uiso 1 1 calc R . . . .
C11 C 0.7602(9) 0.7649(9) 0.1083(7) 0.0824(19) Uani 1 1 d . . . . .
H11 H 0.7078 0.7973 0.0095 0.099 Uiso 1 1 calc R . . . .
C12 C 0.8423(8) 0.4770(10) 0.1388(7) 0.0740(16) Uani 1 1 d . . . . .
H12 H 0.7904 0.5085 0.0399 0.089 Uiso 1 1 calc R . . . .
C13 C 0.9202(9) 0.3162(10) 0.2238(8) 0.0802(18) Uani 1 1 d . . . . .
H13 H 0.9217 0.2377 0.1833 0.096 Uiso 1 1 calc R . . . .
C14 C 0.9990(7) 0.2665(7) 0.3727(7) 0.0658(13) Uani 1 1 d . . . . .
H14 H 1.0518 0.1549 0.4299 0.079 Uiso 1 1 calc R . . . .
C15 C 0.9159(5) 0.6715(5) 0.4073(5) 0.0465(9) Uani 1 1 d . . . . .
C16 C 0.9189(5) 0.5486(5) 0.3486(5) 0.0433(8) Uani 1 1 d . . . . .
C17 C 1.0003(5) 0.3793(5) 0.4367(5) 0.0446(8) Uani 1 1 d . . . . .
C18 C 0.8386(6) 0.5968(7) 0.1973(5) 0.0579(11) 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 111.3 .
O3 C1 C7 106.2 .
O1 C1 O3 121.6 .
O1 C1 C7 132.2 .
O3 C2 C8 106.2 .
O2 C2 O3 121.4 .
O2 C2 C8 132.4 .
C4 C3 Br1 121.9 .
C8 C3 Br1 120.7 .
C8 C3 C4 117.4 .
C3 C4 Br2 119.5 .
C5 C4 Br2 119.8 .
C5 C4 C3 120.7 .
C4 C5 Br3 120.1 .
C4 C5 C6 121.1 .
C6 C5 Br3 118.8 .
C5 C6 Br4 122.0 .
C7 C6 Br4 120.7 .
C7 C6 C5 117.3 .
C6 C7 C1 130.3 .
C8 C7 C1 108.1 .
C8 C7 C6 121.7 .
C3 C8 C2 129.9 .
C7 C8 C2 108.2 .
C7 C8 C3 121.9 .
C10 C9 H9 119.0 .
C15 C9 H9 119.0 .
C15 C9 C10 122.0(6) .
C9 C10 H10 119.7 .
C11 C10 C9 120.6(5) .
C11 C10 H10 119.7 .
C10 C11 H11 119.7 .
C10 C11 C18 120.5(6) .
C18 C11 H11 119.7 .
C13 C12 H12 119.6 .
C13 C12 C18 120.7(5) .
C18 C12 H12 119.6 .
C12 C13 H13 119.8 .
C12 C13 C14 120.4(5) .
C14 C13 H13 119.8 .
C13 C14 H14 119.2 .
C17 C14 C13 121.6(5) .
C17 C14 H14 119.2 .
C9 C15 C16 118.1(5) .
C9 C15 C17 122.8(5) 2_766
C16 C15 C17 119.1(4) 2_766
C15 C16 C18 119.4(4) .
C17 C16 C15 121.6(4) .
C17 C16 C18 119.0(4) .
C14 C17 C15 122.0(4) 2_766
C14 C17 C16 118.6(4) .
C16 C17 C15 119.4(4) 2_766
C11 C18 C16 119.2(5) .
C12 C18 C11 121.1(5) .
C12 C18 C16 119.7(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C1 1.3955 .
O3 C2 1.3922 .
O1 C1 1.1736 .
O2 C2 1.1644 .
Br1 C3 1.8676 .
Br2 C4 1.8781 .
Br3 C5 1.8727 .
Br4 C6 1.8621 .
C1 C7 1.4891 .
C2 C8 1.4905 .
C3 C4 1.3979 .
C3 C8 1.3831 .
C4 C5 1.3958 .
C5 C6 1.3972 .
C6 C7 1.3850 .
C7 C8 1.3740 .
C9 H9 0.9300 .
C9 C10 1.403(10) .
C9 C15 1.368(6) .
C10 H10 0.9300 .
C10 C11 1.342(11) .
C11 H11 0.9300 .
C11 C18 1.404(9) .
C12 H12 0.9300 .
C12 C13 1.347(10) .
C12 C18 1.395(8) .
C13 H13 0.9300 .
C13 C14 1.398(9) .
C14 H14 0.9300 .
C14 C17 1.382(6) .
C15 C16 1.425(6) .
C15 C17 1.472(6) 2_766
C16 C17 1.414(6) .
C16 C18 1.427(6) .
C17 C15 1.472(6) 2_766
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
O3 C1 C7 C6 -177.8 . .
O3 C1 C7 C8 1.7 . .
O3 C2 C8 C3 180.0 . .
O3 C2 C8 C7 2.1 . .
O1 C1 C7 C6 1.9 . .
O1 C1 C7 C8 -178.7 . .
O2 C2 C8 C3 1.8 . .
O2 C2 C8 C7 -176.0 . .
Br1 C3 C4 Br2 -3.5 . .
Br1 C3 C4 C5 177.9 . .
Br1 C3 C8 C2 4.3 . .
Br1 C3 C8 C7 -178.2 . .
Br2 C4 C5 Br3 3.1 . .
Br2 C4 C5 C6 -177.2 . .
Br3 C5 C6 Br4 -2.6 . .
Br3 C5 C6 C7 178.7 . .
Br4 C6 C7 C1 1.3 . .
Br4 C6 C7 C8 -178.0 . .
C1 O3 C2 O2 177.4 . .
C1 O3 C2 C8 -1.1 . .
C1 C7 C8 C2 -2.3 . .
C1 C7 C8 C3 179.7 . .
C2 O3 C1 O1 -180.0 . .
C2 O3 C1 C7 -0.3 . .
C3 C4 C5 Br3 -178.3 . .
C3 C4 C5 C6 1.4 . .
C4 C3 C8 C2 -176.3 . .
C4 C3 C8 C7 1.2 . .
C4 C5 C6 Br4 177.7 . .
C4 C5 C6 C7 -1.0 . .
C5 C6 C7 C1 -180.0 . .
C5 C6 C7 C8 0.7 . .
C6 C7 C8 C2 177.2 . .
C6 C7 C8 C3 -0.9 . .
C8 C3 C4 Br2 177.1 . .
C8 C3 C4 C5 -1.5 . .
C9 C10 C11 C18 -1.0(11) . .
C9 C15 C16 C17 179.5(4) . .
C9 C15 C16 C18 -0.3(6) . .
C10 C9 C15 C16 -0.9(9) . .
C10 C9 C15 C17 178.6(6) . 2_766
C10 C11 C18 C12 -178.9(6) . .
C10 C11 C18 C16 -0.1(9) . .
C12 C13 C14 C17 -0.2(9) . .
C13 C12 C18 C11 179.0(6) . .
C13 C12 C18 C16 0.3(8) . .
C13 C14 C17 C15 -179.5(5) . 2_766
C13 C14 C17 C16 0.2(7) . .
C15 C9 C10 C11 1.6(11) . .
C15 C16 C17 C14 -179.8(4) . .
C15 C16 C17 C15 -0.1(6) . 2_766
C15 C16 C18 C11 0.8(7) . .
C15 C16 C18 C12 179.5(4) . .
C17 C15 C16 C17 0.1(6) 2_766 .
C17 C15 C16 C18 -179.7(4) 2_766 .
C17 C16 C18 C11 -179.0(4) . .
C17 C16 C18 C12 -0.3(6) . .
C18 C12 C13 C14 0.0(9) . .
C18 C16 C17 C14 0.0(6) . .
C18 C16 C17 C15 179.7(4) . 2_766
