#------------------------------------------------------------------------------
#$Date: 2019-11-25 04:54:22 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/93/4129310.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_4129310
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                 118.5970(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1304(8)
_cell_length_b                   13.7261(12)
_cell_length_c                   9.4089(8)
_cell_measurement_reflns_used    7045
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.422
_cell_measurement_theta_min      2.466
_cell_volume                     1035.32(16)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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            15274
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.422
_diffrn_reflns_theta_min         2.465
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.793
_exptl_absorpt_correction_T_max  0.5166
_exptl_absorpt_correction_T_min  0.2971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0994 before and 0.0331 after correction. The Ratio of minimum to maximum transmission is 0.5751. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.008
_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         0.611
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0264
_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)+(0.0306P)²+0.8461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2147
_reflns_number_total             2464
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b00412_si_002.cif
_cod_data_source_block           HMB_TBPA_300K
_cod_database_code               4129310
_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   0.746
_shelx_estimated_absorpt_t_min   0.279
_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 0.93209(4) 0.2500 0.56460(5) 0.04675(11) Uani 1 2 d S T P
Br2 Br 1.06931(4) 0.2500 0.96002(5) 0.05791(13) Uani 1 2 d S T P
Br3 Br 0.80727(6) 0.2500 1.10229(4) 0.06057(14) Uani 1 2 d S T P
Br4 Br 0.40289(5) 0.2500 0.85342(5) 0.05295(12) Uani 1 2 d S T P
O1 O 0.1974(3) 0.2500 0.4631(3) 0.0511(7) Uani 1 2 d S T P
O2 O 0.5521(4) 0.2500 0.2672(3) 0.0510(6) Uani 1 2 d S T P
O3 O 0.3461(3) 0.2500 0.3309(3) 0.0403(5) Uani 1 2 d S T P
C1 C 0.3302(4) 0.2500 0.4700(4) 0.0365(7) Uani 1 2 d S T P
C2 C 0.5141(4) 0.2500 0.3697(4) 0.0348(7) Uani 1 2 d S T P
C3 C 0.7834(4) 0.2500 0.6495(4) 0.0312(6) Uani 1 2 d S T P
C4 C 0.8401(4) 0.2500 0.8158(4) 0.0344(7) Uani 1 2 d S T P
C5 C 0.7275(4) 0.2500 0.8780(4) 0.0351(7) Uani 1 2 d S T P
C6 C 0.5554(4) 0.2500 0.7746(4) 0.0319(6) Uani 1 2 d S T P
C7 C 0.5016(4) 0.2500 0.6094(4) 0.0300(6) Uani 1 2 d S T P
C8 C 0.6118(4) 0.2500 0.5489(3) 0.0288(6) Uani 1 2 d S T P
C9 C 0.2686(5) 0.5013(3) 0.6318(5) 0.0817(11) Uani 1 1 d . . .
H9A H 0.1605 0.4800 0.5505 0.123 Uiso 0.5 1 calc GR . .
H9B H 0.2605 0.5662 0.6655 0.123 Uiso 0.5 1 calc GR . .
H9C H 0.3089 0.4582 0.7231 0.123 Uiso 0.5 1 calc GR . .
H9D H 0.3261 0.5229 0.7423 0.123 Uiso 0.5 1 calc GR . .
H9E H 0.2261 0.4367 0.6272 0.123 Uiso 0.5 1 calc GR . .
H9F H 0.1777 0.5447 0.5696 0.123 Uiso 0.5 1 calc GR . .
C10 C 0.1419(4) 0.4842(3) 0.2825(5) 0.0793(11) Uani 1 1 d . . .
H10A H 0.0831 0.5232 0.3235 0.119 Uiso 0.5 1 calc GR . .
H10B H 0.1084 0.4174 0.2763 0.119 Uiso 0.5 1 calc GR . .
H10C H 0.1165 0.5067 0.1765 0.119 Uiso 0.5 1 calc GR . .
H10D H 0.1222 0.4417 0.1941 0.119 Uiso 0.5 1 calc GR . .
H10E H 0.0969 0.5475 0.2412 0.119 Uiso 0.5 1 calc GR . .
H10F H 0.0889 0.4581 0.3410 0.119 Uiso 0.5 1 calc GR . .
C11 C 0.3755(5) 0.4836(3) 0.1519(4) 0.0800(11) Uani 1 1 d . . .
H11A H 0.4422 0.5235 0.1215 0.120 Uiso 0.5 1 calc GR . .
H11B H 0.2615 0.5048 0.0949 0.120 Uiso 0.5 1 calc GR . .
H11C H 0.3825 0.4169 0.1249 0.120 Uiso 0.5 1 calc GR . .
H11D H 0.2819 0.4400 0.1061 0.120 Uiso 0.5 1 calc GR . .
H11E H 0.4626 0.4587 0.1326 0.120 Uiso 0.5 1 calc GR . .
H11F H 0.3416 0.5466 0.1026 0.120 Uiso 0.5 1 calc GR . .
C12 C 0.3885(4) 0.5005(2) 0.5627(4) 0.0542(7) Uani 1 1 d . . .
C13 C 0.3283(4) 0.4926(2) 0.3950(4) 0.0542(7) Uani 1 1 d . . .
C14 C 0.4390(4) 0.4922(2) 0.3328(4) 0.0549(7) 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 110.6(2) . .
O1 C1 O3 121.1(3) . .
O1 C1 C7 131.9(3) . .
O3 C1 C7 107.0(3) . .
O2 C2 O3 120.4(3) . .
O2 C2 C8 133.0(3) . .
O3 C2 C8 106.6(3) . .
C4 C3 Br1 121.5(2) . .
C8 C3 Br1 121.3(2) . .
C8 C3 C4 117.2(3) . .
C3 C4 Br2 120.0(2) . .
C3 C4 C5 121.0(3) . .
C5 C4 Br2 119.0(2) . .
C4 C5 Br3 120.1(2) . .
C6 C5 Br3 119.1(2) . .
C6 C5 C4 120.8(3) . .
C5 C6 Br4 121.8(2) . .
C7 C6 Br4 120.9(2) . .
C7 C6 C5 117.2(3) . .
C6 C7 C1 130.4(3) . .
C8 C7 C1 107.8(3) . .
C8 C7 C6 121.8(3) . .
C3 C8 C2 130.1(3) . .
C7 C8 C2 108.0(3) . .
C7 C8 C3 121.9(3) . .
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 120.5(3) . .
C13 C12 C14 119.8(3) . 3_666
C14 C12 C9 119.7(3) 3_666 .
C12 C13 C10 119.7(3) . .
C14 C13 C10 120.3(3) . .
C14 C13 C12 120.0(3) . .
C12 C14 C11 119.3(3) 3_666 .
C13 C14 C11 120.5(3) . .
C13 C14 C12 120.1(3) . 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(3) .
Br2 C4 1.872(3) .
Br3 C5 1.874(3) .
Br4 C6 1.865(3) .
O1 C1 1.183(4) .
O2 C2 1.171(4) .
O3 C1 1.384(4) .
O3 C2 1.396(4) .
C1 C7 1.485(4) .
C2 C8 1.483(4) .
C3 C4 1.393(4) .
C3 C8 1.389(4) .
C4 C5 1.405(4) .
C5 C6 1.397(4) .
C6 C7 1.388(4) .
C7 C8 1.374(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C9 H9D 0.9600 .
C9 H9E 0.9600 .
C9 H9F 0.9600 .
C9 C12 1.518(4) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C10 H10D 0.9600 .
C10 H10E 0.9600 .
C10 H10F 0.9600 .
C10 C13 1.518(4) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C11 H11D 0.9600 .
C11 H11E 0.9600 .
C11 H11F 0.9600 .
C11 C14 1.517(4) .
C12 C13 1.404(4) .
C12 C14 1.405(4) 3_666
C13 C14 1.390(4) .
C14 C12 1.405(4) 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(2) . .
Br3 C5 C6 C7 180.000(1) . .
Br4 C6 C7 C1 0.000(2) . .
Br4 C6 C7 C8 180.000(1) . .
O1 C1 C7 C6 0.000(2) . .
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(1) . .
O3 C2 C8 C7 0.000(1) . .
C1 O3 C2 O2 180.000(1) . .
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(1) . .
C2 O3 C1 C7 0.000(1) . .
C3 C4 C5 Br3 180.000(1) . .
C3 C4 C5 C6 0.000(2) . .
C4 C3 C8 C2 180.000(1) . .
C4 C3 C8 C7 0.000(2) . .
C4 C5 C6 Br4 180.000(1) . .
C4 C5 C6 C7 0.000(2) . .
C5 C6 C7 C1 180.000(2) . .
C5 C6 C7 C8 0.000(2) . .
C6 C7 C8 C2 180.000(1) . .
C6 C7 C8 C3 0.000(2) . .
C8 C3 C4 Br2 180.000(1) . .
C8 C3 C4 C5 0.000(2) . .
C9 C12 C13 C10 -0.3(4) . .
C9 C12 C13 C14 179.8(3) . .
C10 C13 C14 C11 0.1(4) . .
C10 C13 C14 C12 -179.6(3) . 3_666
C12 C13 C14 C11 179.9(3) . .
C12 C13 C14 C12 0.2(5) . 3_666
C14 C12 C13 C10 179.6(3) 3_666 .
C14 C12 C13 C14 -0.2(5) 3_666 .
