#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:18:17 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230810 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/63/7156330.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_7156330
loop_
_publ_author_name
'Wang, Denan'
'Ivanov, Maxim V.'
'Mirzaei, Saber'
'Lindeman, Sergey V.'
'Rathore, Rajendra'
_publ_section_title
;
 An electron-transfer induced conformational transformation: from
 non-cofacial "sofa" to cofacial "boat" in
 cyclotetraveratrylene (CTTV) and formation of charge transfer complexes.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5712
_journal_page_last               5717
_journal_paper_doi               10.1039/c8ob01118d
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C50 H44 Cl12 O12'
_chemical_formula_weight         1262.25
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                74.4930(10)
_cell_angle_beta                 89.5790(10)
_cell_angle_gamma                84.4840(10)
_cell_formula_units_Z            1
_cell_length_a                   9.0593(2)
_cell_length_b                   12.1761(2)
_cell_length_c                   12.5506(2)
_cell_measurement_reflns_used    8372
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67
_cell_measurement_theta_min      4
_cell_volume                     1327.60(4)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v2.0-2 (Bruker, 2005)'
_computing_data_reduction        'SADABS-2004/1 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)'
_computing_structure_solution    'XS/SHELXTL v6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11087
_diffrn_reflns_theta_full        67.16
_diffrn_reflns_theta_max         67.16
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    6.256
_exptl_absorpt_correction_T_max  0.5735
_exptl_absorpt_correction_T_min  0.2931
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00024(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         4379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.7739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0637
_reflns_number_gt                4235
_reflns_number_total             4379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob01118d3.cif
_cod_data_source_block           raj6wa
_cod_depositor_comments
'Adding full bibliography for 7156330--7156331.cif.'
_cod_database_code               7156330
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
Cl1 Cl 0.26810(4) 0.16224(3) 0.33056(3) 0.01993(10) Uani 1 1 d
Cl2 Cl 0.60008(4) 0.10598(3) 0.25758(3) 0.02300(11) Uani 1 1 d
O1 O 0.22476(12) 0.04832(9) 0.56137(9) 0.0202(2) Uani 1 1 d
C1 C 0.34948(17) 0.02573(12) 0.53324(13) 0.0161(3) Uani 1 1 d
C2 C 0.39952(17) 0.07434(12) 0.41819(13) 0.0158(3) Uani 1 1 d
C3 C 0.53833(18) 0.05119(13) 0.38824(13) 0.0167(3) Uani 1 1 d
Cl3 Cl 0.24573(4) 0.60452(3) 0.10583(3) 0.02330(11) Uani 1 1 d
Cl4 Cl 0.09833(5) 0.73870(3) -0.12880(3) 0.02611(11) Uani 1 1 d
O2 O 0.12980(13) 0.38435(9) 0.19195(9) 0.0220(3) Uani 1 1 d
C4 C 0.06983(17) 0.43742(13) 0.10538(13) 0.0173(3) Uani 1 1 d
C5 C 0.11265(17) 0.55214(13) 0.04287(13) 0.0173(3) Uani 1 1 d
C6 C 0.04998(18) 0.60840(13) -0.05421(13) 0.0175(3) Uani 1 1 d
O3 O 0.26562(12) -0.19356(9) 0.50338(9) 0.0188(2) Uani 1 1 d
O4 O 0.51062(12) -0.20365(9) 0.39709(9) 0.0174(2) Uani 1 1 d
O5 O -0.31522(12) -0.36575(9) 0.02793(9) 0.0173(2) Uani 1 1 d
O6 O -0.13060(12) -0.42518(9) 0.19584(9) 0.0166(2) Uani 1 1 d
C10 C 0.25302(17) -0.04719(13) 0.03245(12) 0.0148(3) Uani 1 1 d
C11 C 0.25053(17) -0.07876(12) 0.15840(12) 0.0139(3) Uani 1 1 d
C12 C 0.11964(17) -0.06987(12) 0.21616(13) 0.0142(3) Uani 1 1 d
C13 C 0.12297(17) -0.10708(12) 0.33177(13) 0.0149(3) Uani 1 1 d
C14 C 0.25301(17) -0.15368(12) 0.39046(12) 0.0148(3) Uani 1 1 d
C15 C 0.38556(17) -0.16079(12) 0.33251(13) 0.0148(3) Uani 1 1 d
C16 C 0.38258(17) -0.12390(12) 0.21794(13) 0.0148(3) Uani 1 1 d
C17 C 0.12943(19) -0.20410(16) 0.56220(14) 0.0226(4) Uani 1 1 d
C18 C 0.63988(18) -0.23432(15) 0.34108(14) 0.0203(3) Uani 1 1 d
C20 C -0.02772(17) -0.02403(13) 0.15740(13) 0.0146(3) Uani 1 1 d
C21 C -0.10604(16) -0.11100(13) 0.11630(12) 0.0139(3) Uani 1 1 d
C22 C -0.20871(16) -0.07805(12) 0.02828(12) 0.0140(3) Uani 1 1 d
C23 C -0.27877(17) -0.16278(13) -0.00308(13) 0.0148(3) Uani 1 1 d
C24 C -0.25123(16) -0.27784(13) 0.05294(12) 0.0145(3) Uani 1 1 d
C25 C -0.15041(16) -0.31002(12) 0.14290(12) 0.0143(3) Uani 1 1 d
C26 C -0.07782(17) -0.22740(13) 0.17159(12) 0.0144(3) Uani 1 1 d
C27 C -0.42932(19) -0.33436(14) -0.05572(14) 0.0188(3) Uani 1 1 d
C28 C -0.0624(2) -0.45694(14) 0.30394(13) 0.0191(3) Uani 1 1 d
H10A H 0.352(2) -0.0682(16) 0.0101(15) 0.019(4) Uiso 1 1 d
H10B H 0.193(2) -0.0953(16) 0.0052(15) 0.017(4) Uiso 1 1 d
H13 H 0.037(2) -0.0998(15) 0.3696(15) 0.018(4) Uiso 1 1 d
H16 H 0.470(2) -0.1301(14) 0.1779(14) 0.012(4) Uiso 1 1 d
H17A H 0.157(2) -0.2431(17) 0.6375(18) 0.028(5) Uiso 1 1 d
H17B H 0.078(2) -0.1313(18) 0.5586(16) 0.025(5) Uiso 1 1 d
H17C H 0.065(2) -0.2492(17) 0.5336(17) 0.027(5) Uiso 1 1 d
H18A H 0.620(2) -0.2911(17) 0.3016(16) 0.025(5) Uiso 1 1 d
H18B H 0.714(2) -0.2645(17) 0.3968(17) 0.026(5) Uiso 1 1 d
H18C H 0.675(2) -0.1685(17) 0.2893(16) 0.022(5) Uiso 1 1 d
H20A H -0.0133(19) 0.0410(15) 0.0948(15) 0.014(4) Uiso 1 1 d
H20B H -0.093(2) 0.0017(15) 0.2083(15) 0.015(4) Uiso 1 1 d
H23 H -0.342(2) -0.1410(15) -0.0634(15) 0.012(4) Uiso 1 1 d
H26 H -0.011(2) -0.2500(15) 0.2319(16) 0.016(4) Uiso 1 1 d
H27A H -0.469(2) -0.4042(17) -0.0596(15) 0.022(5) Uiso 1 1 d
H27B H -0.507(2) -0.2837(17) -0.0382(16) 0.026(5) Uiso 1 1 d
H27C H -0.392(2) -0.2991(16) -0.1266(16) 0.020(5) Uiso 1 1 d
H28A H -0.067(2) -0.5372(18) 0.3330(16) 0.023(5) Uiso 1 1 d
H28B H 0.041(2) -0.4449(16) 0.3022(16) 0.025(5) Uiso 1 1 d
H28C H -0.114(2) -0.4178(17) 0.3526(17) 0.027(5) Uiso 1 1 d
Cl1S Cl 0.66333(5) -0.53293(4) 0.58622(4) 0.03736(13) Uani 1 1 d
Cl2S Cl 0.42590(5) -0.46913(4) 0.72420(4) 0.03119(12) Uani 1 1 d
C1S C 0.5704(2) -0.42021(16) 0.63426(16) 0.0295(4) Uani 1 1 d
H1SA H 0.526(2) -0.3636(18) 0.5708(18) 0.030(5) Uiso 1 1 d
H1SB H 0.639(2) -0.3925(18) 0.6770(17) 0.030(5) Uiso 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O1 C1 C3 121.85(14) . 2_656
O1 C1 C2 121.71(14) . .
C3 C1 C2 116.44(13) 2_656 .
C3 C2 C1 121.47(14) . .
C3 C2 Cl1 123.38(13) . .
C1 C2 Cl1 115.14(11) . .
C2 C3 C1 122.09(14) . 2_656
C2 C3 Cl2 122.83(13) . .
C1 C3 Cl2 115.08(11) 2_656 .
O2 C4 C6 121.90(14) . 2_565
O2 C4 C5 121.93(15) . .
C6 C4 C5 116.17(14) 2_565 .
C6 C5 C4 121.71(15) . .
C6 C5 Cl3 123.22(13) . .
C4 C5 Cl3 115.07(12) . .
C5 C6 C4 122.10(14) . 2_565
C5 C6 Cl4 122.90(13) . .
C4 C6 Cl4 115.00(12) 2_565 .
C14 O3 C17 116.20(12) . .
C15 O4 C18 116.28(12) . .
C24 O5 C27 116.67(12) . .
C25 O6 C28 116.85(12) . .
C11 C10 C22 116.87(12) . 2
C11 C10 H10A 108.4(11) . .
C22 C10 H10A 108.2(11) 2 .
C11 C10 H10B 109.9(11) . .
C22 C10 H10B 109.4(11) 2 .
H10A C10 H10B 103.1(15) . .
C12 C11 C16 118.98(14) . .
C12 C11 C10 122.15(14) . .
C16 C11 C10 118.78(13) . .
C11 C12 C13 119.47(14) . .
C11 C12 C20 121.96(14) . .
C13 C12 C20 118.56(14) . .
C14 C13 C12 121.52(14) . .
C14 C13 H13 119.3(11) . .
C12 C13 H13 119.2(11) . .
O3 C14 C13 125.26(14) . .
O3 C14 C15 115.65(14) . .
C13 C14 C15 119.09(14) . .
O4 C15 C16 125.07(14) . .
O4 C15 C14 115.44(13) . .
C16 C15 C14 119.48(14) . .
C15 C16 C11 121.44(14) . .
C15 C16 H16 120.4(10) . .
C11 C16 H16 118.1(10) . .
O3 C17 H17A 105.5(12) . .
O3 C17 H17B 111.7(12) . .
H17A C17 H17B 110.0(17) . .
O3 C17 H17C 111.3(12) . .
H17A C17 H17C 109.5(17) . .
H17B C17 H17C 108.8(17) . .
O4 C18 H18A 110.6(12) . .
O4 C18 H18B 105.7(12) . .
H18A C18 H18B 111.3(16) . .
O4 C18 H18C 111.7(11) . .
H18A C18 H18C 109.2(16) . .
H18B C18 H18C 108.3(16) . .
C12 C20 C21 114.96(12) . .
C12 C20 H20A 109.3(10) . .
C21 C20 H20A 108.7(10) . .
C12 C20 H20B 108.1(10) . .
C21 C20 H20B 107.0(10) . .
H20A C20 H20B 108.6(15) . .
C22 C21 C26 119.03(14) . .
C22 C21 C20 122.25(13) . .
C26 C21 C20 118.67(13) . .
C21 C22 C23 118.96(13) . .
C21 C22 C10 122.65(14) . 2
C23 C22 C10 118.34(14) . 2
C24 C23 C22 121.59(14) . .
C24 C23 H23 119.8(11) . .
C22 C23 H23 118.6(11) . .
O5 C24 C23 125.25(14) . .
O5 C24 C25 115.65(13) . .
C23 C24 C25 119.10(14) . .
O6 C25 C26 124.61(14) . .
O6 C25 C24 115.97(13) . .
C26 C25 C24 119.42(14) . .
C25 C26 C21 121.85(14) . .
C25 C26 H26 118.5(11) . .
C21 C26 H26 119.6(11) . .
O5 C27 H27A 107.2(11) . .
O5 C27 H27B 111.5(12) . .
H27A C27 H27B 108.9(16) . .
O5 C27 H27C 111.8(11) . .
H27A C27 H27C 108.3(16) . .
H27B C27 H27C 109.0(16) . .
O6 C28 H28A 107.1(12) . .
O6 C28 H28B 112.6(12) . .
H28A C28 H28B 106.1(16) . .
O6 C28 H28C 111.6(12) . .
H28A C28 H28C 108.9(16) . .
H28B C28 H28C 110.2(16) . .
Cl2S C1S Cl1S 111.41(10) . .
Cl2S C1S H1SA 107.2(12) . .
Cl1S C1S H1SA 107.6(12) . .
Cl2S C1S H1SB 105.9(12) . .
Cl1S C1S H1SB 109.5(12) . .
H1SA C1S H1SB 115.3(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7080(15) .
Cl2 C3 1.7089(15) .
O1 C1 1.2096(19) .
C1 C3 1.490(2) 2_656
C1 C2 1.492(2) .
C2 C3 1.336(2) .
C3 C1 1.490(2) 2_656
Cl3 C5 1.7076(16) .
Cl4 C6 1.7084(15) .
O2 C4 1.208(2) .
C4 C6 1.490(2) 2_565
C4 C5 1.494(2) .
C5 C6 1.329(2) .
C6 C4 1.490(2) 2_565
O3 C14 1.3715(19) .
O3 C17 1.4318(19) .
O4 C15 1.3735(19) .
O4 C18 1.4315(19) .
O5 C24 1.3718(18) .
O5 C27 1.429(2) .
O6 C25 1.3766(18) .
O6 C28 1.4345(19) .
C10 C11 1.524(2) .
C10 C22 1.527(2) 2
C10 H10A 0.967(19) .
C10 H10B 0.962(19) .
C11 C12 1.396(2) .
C11 C16 1.400(2) .
C12 C13 1.399(2) .
C12 C20 1.513(2) .
C13 C14 1.383(2) .
C13 H13 0.920(19) .
C14 C15 1.407(2) .
C15 C16 1.387(2) .
C16 H16 0.942(18) .
C17 H17A 0.96(2) .
C17 H17B 0.95(2) .
C17 H17C 0.97(2) .
C18 H18A 0.98(2) .
C18 H18B 0.95(2) .
C18 H18C 0.96(2) .
C20 C21 1.527(2) .
C20 H20A 0.973(18) .
C20 H20B 0.960(19) .
C21 C22 1.397(2) .
C21 C26 1.401(2) .
C22 C23 1.403(2) .
C22 C10 1.527(2) 2
C23 C24 1.389(2) .
C23 H23 0.920(19) .
C24 C25 1.404(2) .
C25 C26 1.378(2) .
C26 H26 0.935(19) .
C27 H27A 0.97(2) .
C27 H27B 0.96(2) .
C27 H27C 0.95(2) .
C28 H28A 0.95(2) .
C28 H28B 0.96(2) .
C28 H28C 0.96(2) .
Cl1S C1S 1.780(2) .
Cl2S C1S 1.7639(19) .
C1S H1SA 0.96(2) .
C1S H1SB 0.96(2) .
