#------------------------------------------------------------------------------
#$Date: 2019-11-25 04:54:22 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/93/4129311.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_4129311
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, C12 H18'
_chemical_formula_sum            'C20 H18 Br4 O3'
_chemical_formula_weight         625.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 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                90
_cell_angle_beta                 118.3590(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0493(7)
_cell_length_b                   13.3796(10)
_cell_length_c                   9.3465(7)
_cell_measurement_reflns_used    9693
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.395
_cell_measurement_theta_min      2.477
_cell_volume                     995.83(13)
_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      100
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14633
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.411
_diffrn_reflns_theta_min         2.476
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.102
_exptl_absorpt_correction_T_max  0.5049
_exptl_absorpt_correction_T_min  0.2935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0955 before and 0.0305 after correction. The Ratio of minimum to maximum transmission is 0.5813. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.088
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0150
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0214P)²+0.5746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0391
_refine_ls_wR_factor_ref         0.0396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2238
_reflns_number_total             2366
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b00412_si_002.cif
_cod_data_source_block           HMB_TBPA_100K
_cod_database_code               4129311
_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   0.738
_shelx_estimated_absorpt_t_min   0.269
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H9C(0.5) H9D(0.5) H9E(0.5) H9F(0.5) H10A(0.5)
 H10B(0.5) H10C(0.5) H10D(0.5) H10E(0.5) H10F(0.5) H11A(0.5) H11B(0.5)
 H11C(0.5) H11D(0.5) H11E(0.5) H11F(0.5)
3.a Disordered Me refined as rotating group:
 C9(H9A,H9B,H9C,H9D,H9E,H9F), C10(H10A,H10B,H10C,H10D,H10E,H10F), C11(H11A,
 H11B,H11C,H11D,H11E,H11F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
Br1 Br 0.93802(3) 0.2500 0.56895(3) 0.01289(6) Uani 1 2 d S T P
Br2 Br 1.07243(3) 0.2500 0.96561(2) 0.01604(6) Uani 1 2 d S T P
Br3 Br 0.80540(3) 0.2500 1.10650(2) 0.01642(6) Uani 1 2 d S T P
Br4 Br 0.39908(3) 0.2500 0.85489(2) 0.01420(6) Uani 1 2 d S T P
O1 O 0.19499(19) 0.2500 0.46246(19) 0.0151(3) Uani 1 2 d S T P
O2 O 0.5578(2) 0.2500 0.26765(19) 0.0151(3) Uani 1 2 d S T P
O3 O 0.34697(19) 0.2500 0.33040(18) 0.0118(3) Uani 1 2 d S T P
C1 C 0.3293(3) 0.2500 0.4702(2) 0.0105(4) Uani 1 2 d S T P
C2 C 0.5169(3) 0.2500 0.3703(3) 0.0113(4) Uani 1 2 d S T P
C3 C 0.7863(3) 0.2500 0.6527(3) 0.0098(4) Uani 1 2 d S T P
C4 C 0.8418(3) 0.2500 0.8195(3) 0.0112(4) Uani 1 2 d S T P
C5 C 0.7277(3) 0.2500 0.8816(2) 0.0105(4) Uani 1 2 d S T P
C6 C 0.5544(3) 0.2500 0.7763(2) 0.0096(4) Uani 1 2 d S T P
C7 C 0.5012(3) 0.2500 0.6111(2) 0.0096(4) Uani 1 2 d S T P
C8 C 0.6138(3) 0.2500 0.5504(2) 0.0095(4) Uani 1 2 d S T P
C9 C 0.2654(2) 0.50177(14) 0.6319(2) 0.0252(4) Uani 1 1 d . . .
H9A H 0.1547 0.4793 0.5486 0.038 Uiso 0.5 1 calc GR . .
H9B H 0.2567 0.5699 0.6657 0.038 Uiso 0.5 1 calc GR . .
H9C H 0.3064 0.4570 0.7260 0.038 Uiso 0.5 1 calc GR . .
H9D H 0.3238 0.5248 0.7450 0.038 Uiso 0.5 1 calc GR . .
H9E H 0.2218 0.4342 0.6278 0.038 Uiso 0.5 1 calc GR . .
H9F H 0.1721 0.5471 0.5675 0.038 Uiso 0.5 1 calc GR . .
C10 C 0.1394(2) 0.48279(14) 0.2812(2) 0.0256(4) Uani 1 1 d . . .
H10A H 0.0776 0.5116 0.3335 0.038 Uiso 0.5 1 calc GR . .
H10B H 0.1097 0.4121 0.2572 0.038 Uiso 0.5 1 calc GR . .
H10C H 0.1101 0.5187 0.1798 0.038 Uiso 0.5 1 calc GR . .
H10D H 0.1207 0.4500 0.1802 0.038 Uiso 0.5 1 calc GR . .
H10E H 0.0886 0.5495 0.2564 0.038 Uiso 0.5 1 calc GR . .
H10F H 0.0881 0.4429 0.3339 0.038 Uiso 0.5 1 calc GR . .
C11 C 0.3771(2) 0.48337(14) 0.1500(2) 0.0262(4) Uani 1 1 d . . .
H11A H 0.4669 0.5029 0.1252 0.039 Uiso 0.5 1 calc GR . .
H11B H 0.2803 0.5276 0.0921 0.039 Uiso 0.5 1 calc GR . .
H11C H 0.3438 0.4142 0.1153 0.039 Uiso 0.5 1 calc GR . .
H11D H 0.2604 0.4602 0.0965 0.039 Uiso 0.5 1 calc GR . .
H11E H 0.4470 0.4355 0.1296 0.039 Uiso 0.5 1 calc GR . .
H11F H 0.3835 0.5489 0.1064 0.039 Uiso 0.5 1 calc GR . .
C12 C 0.3868(2) 0.50053(11) 0.5630(2) 0.0171(3) Uani 1 1 d . . .
C13 C 0.3267(2) 0.49212(12) 0.3943(2) 0.0174(3) Uani 1 1 d . . .
C14 C 0.4397(2) 0.49184(12) 0.3314(2) 0.0175(3) 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_1
_geom_angle_site_symmetry_3
C1 O3 C2 110.59(16) . .
O1 C1 O3 121.08(19) . .
O1 C1 C7 131.8(2) . .
O3 C1 C7 107.09(17) . .
O2 C2 O3 120.81(19) . .
O2 C2 C8 132.6(2) . .
O3 C2 C8 106.60(17) . .
C4 C3 Br1 121.38(16) . .
C8 C3 Br1 121.22(15) . .
C8 C3 C4 117.40(19) . .
C3 C4 Br2 120.03(16) . .
C3 C4 C5 121.17(19) . .
C5 C4 Br2 118.80(16) . .
C4 C5 Br3 120.40(16) . .
C6 C5 Br3 119.11(15) . .
C6 C5 C4 120.49(19) . .
C5 C6 Br4 121.58(15) . .
C7 C6 Br4 120.74(16) . .
C7 C6 C5 117.68(19) . .
C6 C7 C1 130.8(2) . .
C6 C7 C8 121.69(19) . .
C8 C7 C1 107.56(18) . .
C3 C8 C2 130.3(2) . .
C7 C8 C2 108.15(18) . .
C7 C8 C3 121.58(19) . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9A C9 H9D 141.1 . .
H9A C9 H9E 56.3 . .
H9A C9 H9F 56.3 . .
H9B C9 H9C 109.5 . .
H9B C9 H9D 56.3 . .
H9B C9 H9E 141.1 . .
H9B C9 H9F 56.3 . .
H9C C9 H9D 56.3 . .
H9C C9 H9E 56.3 . .
H9C C9 H9F 141.1 . .
H9D C9 H9E 109.5 . .
H9D C9 H9F 109.5 . .
H9E C9 H9F 109.5 . .
C12 C9 H9A 109.5 . .
C12 C9 H9B 109.5 . .
C12 C9 H9C 109.5 . .
C12 C9 H9D 109.5 . .
C12 C9 H9E 109.5 . .
C12 C9 H9F 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10A C10 H10D 141.1 . .
H10A C10 H10E 56.3 . .
H10A C10 H10F 56.3 . .
H10B C10 H10C 109.5 . .
H10B C10 H10D 56.3 . .
H10B C10 H10E 141.1 . .
H10B C10 H10F 56.3 . .
H10C C10 H10D 56.3 . .
H10C C10 H10E 56.3 . .
H10C C10 H10F 141.1 . .
H10D C10 H10E 109.5 . .
H10D C10 H10F 109.5 . .
H10E C10 H10F 109.5 . .
C13 C10 H10A 109.5 . .
C13 C10 H10B 109.5 . .
C13 C10 H10C 109.5 . .
C13 C10 H10D 109.5 . .
C13 C10 H10E 109.5 . .
C13 C10 H10F 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11A C11 H11D 141.1 . .
H11A C11 H11E 56.3 . .
H11A C11 H11F 56.3 . .
H11B C11 H11C 109.5 . .
H11B C11 H11D 56.3 . .
H11B C11 H11E 141.1 . .
H11B C11 H11F 56.3 . .
H11C C11 H11D 56.3 . .
H11C C11 H11E 56.3 . .
H11C C11 H11F 141.1 . .
H11D C11 H11E 109.5 . .
H11D C11 H11F 109.5 . .
H11E C11 H11F 109.5 . .
C14 C11 H11A 109.5 . .
C14 C11 H11B 109.5 . .
C14 C11 H11C 109.5 . .
C14 C11 H11D 109.5 . .
C14 C11 H11E 109.5 . .
C14 C11 H11F 109.5 . .
C13 C12 C9 120.33(15) . .
C14 C12 C9 119.63(15) 3_666 .
C14 C12 C13 120.04(16) 3_666 .
C12 C13 C10 119.80(16) . .
C14 C13 C10 120.21(16) . .
C14 C13 C12 119.99(15) . .
C12 C14 C11 119.32(16) 3_666 .
C13 C14 C11 120.71(15) . .
C13 C14 C12 119.97(15) . 3_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.876(2) .
Br2 C4 1.874(2) .
Br3 C5 1.873(2) .
Br4 C6 1.869(2) .
O1 C1 1.183(3) .
O2 C2 1.182(3) .
O3 C1 1.390(2) .
O3 C2 1.399(3) .
C1 C7 1.486(3) .
C2 C8 1.483(3) .
C3 C4 1.393(3) .
C3 C8 1.390(3) .
C4 C5 1.404(3) .
C5 C6 1.401(3) .
C6 C7 1.382(3) .
C7 C8 1.383(3) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C9 H9D 0.9800 .
C9 H9E 0.9800 .
C9 H9F 0.9800 .
C9 C12 1.514(2) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C10 H10D 0.9800 .
C10 H10E 0.9800 .
C10 H10F 0.9800 .
C10 C13 1.517(2) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C11 H11D 0.9800 .
C11 H11E 0.9800 .
C11 H11F 0.9800 .
C11 C14 1.516(2) .
C12 C13 1.407(2) .
C12 C14 1.406(2) 3_666
C13 C14 1.402(2) .
C14 C12 1.406(2) 3_666
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 0.000(1) . .
Br1 C3 C4 C5 180.000(1) . .
Br1 C3 C8 C2 0.000(1) . .
Br1 C3 C8 C7 180.000(1) . .
Br2 C4 C5 Br3 0.000(1) . .
Br2 C4 C5 C6 180.000(1) . .
Br3 C5 C6 Br4 0.000(1) . .
Br3 C5 C6 C7 180.000(1) . .
Br4 C6 C7 C1 0.000(1) . .
Br4 C6 C7 C8 180.000(1) . .
O1 C1 C7 C6 0.000(1) . .
O1 C1 C7 C8 180.000(1) . .
O2 C2 C8 C3 0.000(1) . .
O2 C2 C8 C7 180.000(1) . .
O3 C1 C7 C6 180.000(1) . .
O3 C1 C7 C8 0.000(1) . .
O3 C2 C8 C3 180.000(0) . .
O3 C2 C8 C7 0.000(1) . .
C1 O3 C2 O2 180.000(0) . .
C1 O3 C2 C8 0.000(1) . .
C1 C7 C8 C2 0.000(1) . .
C1 C7 C8 C3 180.000(1) . .
C2 O3 C1 O1 180.000(0) . .
C2 O3 C1 C7 0.000(1) . .
C3 C4 C5 Br3 180.000(1) . .
C3 C4 C5 C6 0.000(1) . .
C4 C3 C8 C2 180.000(1) . .
C4 C3 C8 C7 0.000(1) . .
C4 C5 C6 Br4 180.000(1) . .
C4 C5 C6 C7 0.000(1) . .
C5 C6 C7 C1 180.000(1) . .
C5 C6 C7 C8 0.000(1) . .
C6 C7 C8 C2 180.000(1) . .
C6 C7 C8 C3 0.000(1) . .
C8 C3 C4 Br2 180.000(0) . .
C8 C3 C4 C5 0.000(1) . .
C9 C12 C13 C10 -0.9(2) . .
C9 C12 C13 C14 179.49(15) . .
C10 C13 C14 C11 0.7(2) . .
C10 C13 C14 C12 -179.34(15) . 3_666
C12 C13 C14 C11 -179.69(15) . .
C12 C13 C14 C12 0.3(3) . 3_666
C14 C12 C13 C10 179.34(15) 3_666 .
C14 C12 C13 C14 -0.3(3) 3_666 .
