#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/12/7121268.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_7121268
loop_
_publ_author_name
'Jiang, Chuanling'
'Bang, Yawen'
'Wang, Xinhao'
'Lu, Xuefeng'
'Lim, Zhenglong'
'Wei, Haipeng'
'El-Hankari, Samir'
'Wu, Jishan'
'Zeng, Zebing'
_publ_section_title
;
 Tetrabenzo-Chichibabin's hydrocarbons: substituent effects and unusual
 thermochromic and thermomagnetic behaviours.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2389
_journal_page_last               2392
_journal_paper_doi               10.1039/c8cc00378e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C68 H64 Cl4 O12'
_chemical_formula_weight         1214.99
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-07-24 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                106.135(5)
_cell_angle_beta                 94.598(5)
_cell_angle_gamma                100.939(5)
_cell_formula_units_Z            1
_cell_length_a                   7.3362(17)
_cell_length_b                   12.952(3)
_cell_length_c                   16.918(4)
_cell_measurement_reflns_used    1010
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.5155
_cell_measurement_theta_min      2.8565
_cell_volume                     1501.0(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19631
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9496
_exptl_absorpt_correction_T_min  0.8589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.984
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         6894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0544P)²+1.7693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                5427
_reflns_number_total             6894
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc00378e2.cif
_cod_data_source_block           b494
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'Not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7121266--7121269.cif.
;
_cod_original_cell_volume        1501.1(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7121268
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.3115(2) 0.09297(13) 0.40592(10) 0.0204(4) Uani 1 1 d .
O2 O 0.2135(2) -0.09963(13) 0.28378(10) 0.0182(3) Uani 1 1 d .
O3 O 0.4134(2) -0.14575(13) 0.15931(10) 0.0200(4) Uani 1 1 d .
O4 O 0.7922(2) 0.36723(14) 0.05869(10) 0.0226(4) Uani 1 1 d .
O5 O 0.9991(2) 0.24036(14) -0.03335(10) 0.0233(4) Uani 1 1 d .
O6 O 1.1712(2) 0.11017(14) 0.02724(10) 0.0223(4) Uani 1 1 d .
C1 C 0.4248(3) 0.07772(19) 0.34522(14) 0.0170(5) Uani 1 1 d .
C2 C 0.3700(3) -0.02269(18) 0.28193(14) 0.0157(4) Uani 1 1 d .
C3 C 0.4807(3) -0.04669(18) 0.21822(14) 0.0166(4) Uani 1 1 d .
C4 C 0.6460(3) 0.02754(18) 0.21896(13) 0.0164(4) Uani 1 1 d .
H4 H 0.7211 0.0105 0.1760 0.020 Uiso 1 1 calc R
C5 C 0.7011(3) 0.12707(18) 0.28308(14) 0.0155(4) Uani 1 1 d .
C6 C 0.5858(3) 0.15316(18) 0.34426(14) 0.0167(4) Uani 1 1 d .
H6 H 0.6180 0.2230 0.3854 0.020 Uiso 1 1 calc R
C7 C 0.8828(3) 0.20450(18) 0.28591(13) 0.0144(4) Uani 1 1 d .
C8 C 0.9227(3) 0.21752(18) 0.20308(13) 0.0148(4) Uani 1 1 d .
C9 C 0.8396(3) 0.28908(19) 0.17240(14) 0.0178(5) Uani 1 1 d .
H9 H 0.7631 0.3307 0.2046 0.021 Uiso 1 1 calc R
C10 C 0.8685(3) 0.29978(18) 0.09445(14) 0.0173(5) Uani 1 1 d .
C11 C 0.9804(3) 0.23852(18) 0.04637(14) 0.0176(5) Uani 1 1 d .
C12 C 1.0642(3) 0.16715(18) 0.07782(14) 0.0175(5) Uani 1 1 d .
C13 C 1.0343(3) 0.15627(18) 0.15587(14) 0.0166(4) Uani 1 1 d .
H13 H 1.0902 0.1070 0.1768 0.020 Uiso 1 1 calc R
C14 C 0.3861(3) 0.1812(2) 0.48033(15) 0.0247(5) Uani 1 1 d .
H14A H 0.5144 0.1780 0.4988 0.037 Uiso 1 1 calc R
H14B H 0.3080 0.1744 0.5238 0.037 Uiso 1 1 calc R
H14C H 0.3869 0.2518 0.4695 0.037 Uiso 1 1 calc R
C15 C 0.0426(3) -0.0813(2) 0.24852(15) 0.0210(5) Uani 1 1 d .
H15A H 0.0353 -0.0045 0.2734 0.032 Uiso 1 1 calc R
H15B H -0.0645 -0.1304 0.2597 0.032 Uiso 1 1 calc R
H15C H 0.0403 -0.0963 0.1883 0.032 Uiso 1 1 calc R
C16 C 0.5215(4) -0.1763(2) 0.09358(15) 0.0252(5) Uani 1 1 d .
H16A H 0.5277 -0.1239 0.0612 0.038 Uiso 1 1 calc R
H16B H 0.4625 -0.2506 0.0574 0.038 Uiso 1 1 calc R
H16C H 0.6486 -0.1753 0.1171 0.038 Uiso 1 1 calc R
C17 C 0.6705(4) 0.4276(2) 0.10402(17) 0.0313(6) Uani 1 1 d .
H17A H 0.5665 0.3761 0.1151 0.047 Uiso 1 1 calc R
H17B H 0.6208 0.4703 0.0713 0.047 Uiso 1 1 calc R
H17C H 0.7406 0.4777 0.1568 0.047 Uiso 1 1 calc R
C18 C 1.1103(4) 0.3399(2) -0.04040(16) 0.0285(6) Uani 1 1 d .
H18A H 1.0505 0.4013 -0.0179 0.043 Uiso 1 1 calc R
H18B H 1.1211 0.3321 -0.0990 0.043 Uiso 1 1 calc R
H18C H 1.2355 0.3545 -0.0091 0.043 Uiso 1 1 calc R
C19 C 1.2623(4) 0.0390(2) 0.05910(15) 0.0244(5) Uani 1 1 d .
H19A H 1.3546 0.0830 0.1076 0.037 Uiso 1 1 calc R
H19B H 1.3259 -0.0018 0.0161 0.037 Uiso 1 1 calc R
H19C H 1.1690 -0.0131 0.0755 0.037 Uiso 1 1 calc R
C20 C 0.9979(3) 0.26283(17) 0.35733(13) 0.0138(4) Uani 1 1 d .
C21 C 0.9677(3) 0.25330(18) 0.44156(14) 0.0152(4) Uani 1 1 d .
C22 C 0.9274(3) 0.15175(19) 0.45830(15) 0.0175(5) Uani 1 1 d .
H22 H 0.9102 0.0850 0.4143 0.021 Uiso 1 1 calc R
C23 C 0.9128(3) 0.14859(19) 0.53901(15) 0.0191(5) Uani 1 1 d .
H23 H 0.8822 0.0797 0.5500 0.023 Uiso 1 1 calc R
C24 C 0.9429(3) 0.2463(2) 0.60380(14) 0.0188(5) Uani 1 1 d .
H24 H 0.9359 0.2439 0.6591 0.023 Uiso 1 1 calc R
C25 C 0.9830(3) 0.34696(19) 0.58819(14) 0.0166(5) Uani 1 1 d .
H25 H 1.0044 0.4134 0.6328 0.020 Uiso 1 1 calc R
C26 C 0.9919(3) 0.35092(18) 0.50656(13) 0.0140(4) Uani 1 1 d .
C27 C 1.0384(3) 0.45653(18) 0.48538(13) 0.0137(4) Uani 1 1 d .
C28 C 1.1831(3) 0.45152(18) 0.42817(13) 0.0137(4) Uani 1 1 d .
C29 C 1.3407(3) 0.53644(18) 0.44110(13) 0.0155(4) Uani 1 1 d .
H29 H 1.3523 0.6028 0.4849 0.019 Uiso 1 1 calc R
C30 C 1.4810(3) 0.52587(19) 0.39116(14) 0.0172(5) Uani 1 1 d .
H30 H 1.5875 0.5846 0.4002 0.021 Uiso 1 1 calc R
C31 C 1.4641(3) 0.4285(2) 0.32776(14) 0.0195(5) Uani 1 1 d .
H31 H 1.5599 0.4207 0.2933 0.023 Uiso 1 1 calc R
C32 C 1.3090(3) 0.34226(19) 0.31399(14) 0.0177(5) Uani 1 1 d .
H32 H 1.2998 0.2758 0.2706 0.021 Uiso 1 1 calc R
C33 C 1.1658(3) 0.35281(18) 0.36382(13) 0.0139(4) Uani 1 1 d .
C1S C 0.3644(4) 0.6639(2) 0.24890(17) 0.0281(6) Uani 1 1 d .
H1S1 H 0.3283 0.6516 0.3013 0.034 Uiso 1 1 calc R
H1S2 H 0.3222 0.7299 0.2431 0.034 Uiso 1 1 calc R
Cl1 Cl 0.61020(10) 0.68697(7) 0.25371(5) 0.0417(2) Uani 1 1 d .
Cl2 Cl 0.25310(17) 0.54915(8) 0.16480(8) 0.0868(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'
Cl Cl 0.1484 0.1585 '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
C1 O1 C14 116.32(17) .
C2 O2 C15 113.21(17) .
C3 O3 C16 117.35(18) .
C10 O4 C17 117.00(18) .
C11 O5 C18 115.34(18) .
C12 O6 C19 116.73(18) .
O1 C1 C6 124.4(2) .
O1 C1 C2 115.38(19) .
C6 C1 C2 120.2(2) .
O2 C2 C1 120.59(19) .
O2 C2 C3 120.02(19) .
C1 C2 C3 119.3(2) .
O3 C3 C4 125.1(2) .
O3 C3 C2 114.52(19) .
C4 C3 C2 120.4(2) .
C3 C4 C5 119.9(2) .
C6 C5 C4 119.6(2) .
C6 C5 C7 120.54(19) .
C4 C5 C7 119.90(19) .
C1 C6 C5 120.5(2) .
C20 C7 C5 123.23(19) .
C20 C7 C8 122.2(2) .
C5 C7 C8 114.45(19) .
C9 C8 C13 120.1(2) .
C9 C8 C7 118.68(19) .
C13 C8 C7 121.2(2) .
C8 C9 C10 120.0(2) .
O4 C10 C9 124.4(2) .
O4 C10 C11 115.2(2) .
C9 C10 C11 120.4(2) .
O5 C11 C12 118.8(2) .
O5 C11 C10 121.8(2) .
C12 C11 C10 119.2(2) .
O6 C12 C13 124.0(2) .
O6 C12 C11 115.79(19) .
C13 C12 C11 120.2(2) .
C8 C13 C12 120.1(2) .
C7 C20 C21 125.0(2) .
C7 C20 C33 124.47(19) .
C21 C20 C33 110.34(18) .
C26 C21 C22 119.5(2) .
C26 C21 C20 117.55(19) .
C22 C21 C20 122.9(2) .
C23 C22 C21 120.2(2) .
C22 C23 C24 120.0(2) .
C25 C24 C23 120.4(2) .
C24 C25 C26 120.0(2) .
C21 C26 C25 119.9(2) .
C21 C26 C27 117.13(19) .
C25 C26 C27 122.9(2) .
C27 C27 C28 125.3(2) 2_766
C27 C27 C26 124.6(2) 2_766
C28 C27 C26 110.14(18) .
C29 C28 C33 119.73(19) .
C29 C28 C27 122.3(2) .
C33 C28 C27 117.75(19) .
C30 C29 C28 121.1(2) .
C29 C30 C31 119.2(2) .
C30 C31 C32 120.8(2) .
C31 C32 C33 120.3(2) .
C32 C33 C28 118.9(2) .
C32 C33 C20 124.6(2) .
C28 C33 C20 116.44(18) .
Cl2 C1S Cl1 111.13(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.368(3) .
O1 C14 1.430(3) .
O2 C2 1.379(3) .
O2 C15 1.434(3) .
O3 C3 1.361(3) .
O3 C16 1.428(3) .
O4 C10 1.366(3) .
O4 C17 1.428(3) .
O5 C11 1.373(3) .
O5 C18 1.429(3) .
O6 C12 1.367(3) .
O6 C19 1.428(3) .
C1 C6 1.387(3) .
C1 C2 1.399(3) .
C2 C3 1.403(3) .
C3 C4 1.394(3) .
C4 C5 1.399(3) .
C5 C6 1.398(3) .
C5 C7 1.497(3) .
C7 C20 1.353(3) .
C7 C8 1.502(3) .
C8 C9 1.390(3) .
C8 C13 1.392(3) .
C9 C10 1.392(3) .
C10 C11 1.401(3) .
C11 C12 1.397(3) .
C12 C13 1.396(3) .
C20 C21 1.494(3) .
C20 C33 1.500(3) .
C21 C26 1.396(3) .
C21 C22 1.404(3) .
C22 C23 1.389(3) .
C23 C24 1.392(3) .
C24 C25 1.383(3) .
C25 C26 1.402(3) .
C26 C27 1.494(3) .
C27 C27 1.344(4) 2_766
C27 C28 1.491(3) .
C28 C29 1.392(3) .
C28 C33 1.407(3) .
C29 C30 1.386(3) .
C30 C31 1.387(3) .
C31 C32 1.388(3) .
C32 C33 1.402(3) .
C1S Cl2 1.754(3) .
C1S Cl1 1.763(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188434
