#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:20:11 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298790 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/37/1573779.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_1573779
loop_
_publ_author_name
'Xu, Xiang'
'Ma, Hao-Ran'
'Cui, Jian-Fang'
'Peng, Xiao-Shui'
'Wong, Henry N. C.'
_publ_section_title
;
 Regioselective late-stage functionalization of tetraphenylenes: rapid
 construction of double helical architectures and potential hole transport
 materials.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              4342
_journal_page_last               4351
_journal_paper_doi               10.1039/d4sc07803a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C64 H60 O2'
_chemical_formula_sum            'C64 H60 O2'
_chemical_formula_weight         861.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2025-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.354(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8746(12)
_cell_length_b                   19.1113(14)
_cell_length_c                   17.1888(14)
_cell_measurement_reflns_used    7967
_cell_measurement_temperature    297
_cell_measurement_theta_max      23.637
_cell_measurement_theta_min      2.443
_cell_volume                     5171.9(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31660
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.780
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0668
_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)+(0.0594P)²+7.7987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1765
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2848
_reflns_number_total             4678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07803a2.cif
_cod_data_source_block           sam1-1
_cod_depositor_comments          'Adding full bibliography for 1573779.cif.'
_cod_database_code               1573779
_shelx_shelxl_version_number     2018/3
_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   0.987
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C14(H14), C16(H16),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O1 O 0.500000 0.03820(15) 0.250000 0.0844(11) Uani 1 2 d S T P . .
O2 O 0.500000 0.5718(2) 0.250000 0.170(3) Uani 1 2 d S T P . .
C1 C 0.5673(2) 0.06994(15) 0.22117(17) 0.0566(8) Uani 1 1 d . . . . .
C2 C 0.5979(3) 0.03424(17) 0.1608(2) 0.0778(11) Uani 1 1 d . . . . .
H2 H 0.568687 -0.004713 0.138968 0.093 Uiso 1 1 calc R . . . .
C3 C 0.6700(3) 0.0553(2) 0.1329(2) 0.0887(13) Uani 1 1 d . . . . .
H3 H 0.689719 0.030832 0.092061 0.106 Uiso 1 1 calc R . . . .
C4 C 0.7138(3) 0.1122(2) 0.1644(2) 0.0846(11) Uani 1 1 d . . . . .
H4 H 0.763666 0.126356 0.146010 0.102 Uiso 1 1 calc R . . . .
C5 C 0.6826(2) 0.14852(17) 0.22423(18) 0.0628(9) Uani 1 1 d . . . . .
H5 H 0.712050 0.187679 0.245186 0.075 Uiso 1 1 calc R . . . .
C6 C 0.60925(18) 0.12869(13) 0.25403(15) 0.0449(7) Uani 1 1 d . . . . .
C7 C 0.57830(16) 0.17365(12) 0.31552(14) 0.0395(6) Uani 1 1 d . . . . .
C8 C 0.60915(16) 0.16600(13) 0.39437(14) 0.0430(7) Uani 1 1 d . . . . .
H8 H 0.647620 0.130278 0.409326 0.052 Uiso 1 1 calc R . . . .
C9 C 0.58447(16) 0.20988(13) 0.45144(14) 0.0399(6) Uani 1 1 d . . . . .
C10 C 0.53043(16) 0.26461(13) 0.42578(14) 0.0414(6) Uani 1 1 d . . . . .
H10 H 0.514842 0.296091 0.462642 0.050 Uiso 1 1 calc R . . . .
C11 C 0.49866(15) 0.27437(12) 0.34743(14) 0.0358(6) Uani 1 1 d . . . . .
C12 C 0.52044(15) 0.22714(12) 0.29162(13) 0.0349(6) Uani 1 1 d . . . . .
C13 C 0.43966(16) 0.33272(12) 0.32278(14) 0.0366(6) Uani 1 1 d . . . . .
C14 C 0.36373(16) 0.33840(13) 0.35467(14) 0.0424(6) Uani 1 1 d . . . . .
H14 H 0.352088 0.306067 0.392296 0.051 Uiso 1 1 calc R . . . .
C15 C 0.30470(17) 0.39054(14) 0.33239(15) 0.0446(7) Uani 1 1 d . . . . .
C16 C 0.32507(18) 0.43798(15) 0.27673(16) 0.0510(7) Uani 1 1 d . . . . .
H16 H 0.286757 0.473528 0.260620 0.061 Uiso 1 1 calc R . . . .
C17 C 0.40049(17) 0.43438(13) 0.24420(15) 0.0442(7) Uani 1 1 d . . . . .
C18 C 0.45878(15) 0.38122(12) 0.26694(14) 0.0358(6) Uani 1 1 d . . . . .
C19 C 0.41553(18) 0.48058(15) 0.17735(19) 0.0572(8) Uani 1 1 d . . . . .
C20 C 0.3800(2) 0.4601(2) 0.1038(2) 0.0795(11) Uani 1 1 d . . . . .
H20 H 0.347930 0.419241 0.098718 0.095 Uiso 1 1 calc R . . . .
C21 C 0.3901(3) 0.4978(4) 0.0371(3) 0.135(2) Uani 1 1 d . . . . .
H21 H 0.367223 0.481808 -0.012162 0.162 Uiso 1 1 calc R . . . .
C22 C 0.4343(5) 0.5589(5) 0.0451(5) 0.185(4) Uani 1 1 d . . . . .
H22 H 0.438144 0.586710 0.001279 0.222 Uiso 1 1 calc R . . . .
C23 C 0.4718(4) 0.5789(3) 0.1142(5) 0.161(3) Uani 1 1 d . . . . .
H23 H 0.504762 0.619309 0.117788 0.193 Uiso 1 1 calc R . . . .
C24 C 0.4633(2) 0.5410(2) 0.1826(3) 0.0966(14) Uani 1 1 d . . . . .
C25 C 0.61066(18) 0.19753(15) 0.53931(15) 0.0507(7) Uani 1 1 d . . . . .
C26 C 0.6783(3) 0.1420(3) 0.5555(2) 0.1170(18) Uani 1 1 d . . . . .
H26A H 0.657377 0.098489 0.532818 0.175 Uiso 1 1 calc GR . . . .
H26B H 0.692552 0.136444 0.611133 0.175 Uiso 1 1 calc GR . . . .
H26C H 0.727954 0.155869 0.532855 0.175 Uiso 1 1 calc GR . . . .
C27 C 0.6478(3) 0.2640(2) 0.5790(2) 0.1177(17) Uani 1 1 d . . . . .
H27A H 0.698536 0.276702 0.557347 0.177 Uiso 1 1 calc GR . . . .
H27B H 0.661221 0.255958 0.634287 0.177 Uiso 1 1 calc GR . . . .
H27C H 0.607103 0.301234 0.570211 0.177 Uiso 1 1 calc GR . . . .
C28 C 0.5341(3) 0.1775(3) 0.5758(2) 0.143(2) Uani 1 1 d . . . . .
H28A H 0.492446 0.214091 0.567362 0.214 Uiso 1 1 calc GR . . . .
H28B H 0.549588 0.170700 0.631135 0.214 Uiso 1 1 calc GR . . . .
H28C H 0.510840 0.134936 0.552546 0.214 Uiso 1 1 calc GR . . . .
C29 C 0.21803(18) 0.39230(17) 0.36290(16) 0.0580(8) Uani 1 1 d . . . . .
C30 C 0.1520(2) 0.3654(3) 0.2981(2) 0.0982(14) Uani 1 1 d . . . . .
H30A H 0.154957 0.392037 0.251198 0.147 Uiso 1 1 calc GR . . . .
H30B H 0.096463 0.370100 0.313944 0.147 Uiso 1 1 calc GR . . . .
H30C H 0.162915 0.316992 0.288235 0.147 Uiso 1 1 calc GR . . . .
C31 C 0.2176(2) 0.3490(2) 0.4372(2) 0.0895(13) Uani 1 1 d . . . . .
H31A H 0.223273 0.300376 0.425108 0.134 Uiso 1 1 calc GR . . . .
H31B H 0.165062 0.356383 0.458195 0.134 Uiso 1 1 calc GR . . . .
H31C H 0.264129 0.363110 0.475244 0.134 Uiso 1 1 calc GR . . . .
C32 C 0.1941(2) 0.4675(2) 0.3830(2) 0.0933(13) Uani 1 1 d . . . . .
H32A H 0.234935 0.485141 0.424419 0.140 Uiso 1 1 calc GR . . . .
H32B H 0.138730 0.467644 0.399829 0.140 Uiso 1 1 calc GR . . . .
H32C H 0.193788 0.496555 0.337479 0.140 Uiso 1 1 calc GR . . . .
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'
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
_geom_angle_publ_flag
C1 O1 C1 127.6(3) . 2_655 ?
C24 O2 C24 128.8(4) 2_655 . ?
O1 C1 C2 114.6(3) . . ?
O1 C1 C6 124.4(3) . . ?
C2 C1 C6 120.6(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.4(3) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C7 124.7(3) . . ?
C5 C6 C1 117.0(3) . . ?
C5 C6 C7 118.2(2) . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 C12 120.0(2) . . ?
C12 C7 C6 118.4(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.1(2) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 116.8(2) . . ?
C8 C9 C25 122.6(2) . . ?
C10 C9 C25 120.5(2) . . ?
C9 C10 H10 118.6 . . ?
C9 C10 C11 122.8(2) . . ?
C11 C10 H10 118.6 . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 C13 121.1(2) . . ?
C12 C11 C13 119.6(2) . . ?
C7 C12 C12 117.99(19) . 2_655 ?
C11 C12 C7 118.8(2) . . ?
C11 C12 C12 123.0(2) . 2_655 ?
C14 C13 C11 119.6(2) . . ?
C14 C13 C18 119.7(2) . . ?
C18 C13 C11 120.7(2) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.4(2) . . ?
C15 C14 H14 118.8 . . ?
C14 C15 C29 121.7(2) . . ?
C16 C15 C14 116.8(2) . . ?
C16 C15 C29 121.3(2) . . ?
C15 C16 H16 118.8 . . ?
C15 C16 C17 122.4(2) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 C19 120.8(2) . . ?
C18 C17 C19 118.7(2) . . ?
C13 C18 C17 118.8(2) . . ?
C13 C18 C18 123.00(19) . 2_655 ?
C17 C18 C18 118.15(19) . 2_655 ?
C20 C19 C17 116.9(3) . . ?
C20 C19 C24 117.2(3) . . ?
C24 C19 C17 125.9(3) . . ?
C19 C20 H20 118.8 . . ?
C19 C20 C21 122.5(5) . . ?
C21 C20 H20 118.8 . . ?
C20 C21 H21 120.7 . . ?
C22 C21 C20 118.6(6) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.6(6) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.1 . . ?
C22 C23 C24 121.7(6) . . ?
C24 C23 H23 119.1 . . ?
O2 C24 C19 126.1(4) . . ?
O2 C24 C23 114.4(4) . . ?
C19 C24 C23 119.3(5) . . ?
C26 C25 C9 112.8(2) . . ?
C26 C25 C27 106.1(3) . . ?
C27 C25 C9 110.7(2) . . ?
C28 C25 C9 108.8(2) . . ?
C28 C25 C26 110.0(3) . . ?
C28 C25 C27 108.4(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C15 C29 C32 110.8(3) . . ?
C30 C29 C15 107.9(2) . . ?
C30 C29 C31 110.8(3) . . ?
C30 C29 C32 108.4(3) . . ?
C31 C29 C15 112.1(2) . . ?
C31 C29 C32 106.9(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.375(3) . ?
O1 C1 1.375(3) 2_655 ?
O2 C24 1.363(5) 2_655 ?
O2 C24 1.363(5) . ?
C1 C2 1.381(4) . ?
C1 C6 1.388(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C6 C7 1.493(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.400(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(3) . ?
C9 C10 1.388(3) . ?
C9 C25 1.533(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(3) . ?
C11 C12 1.393(3) . ?
C11 C13 1.483(3) . ?
C12 C12 1.493(5) 2_655 ?
C13 C14 1.391(3) . ?
C13 C18 1.395(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 C16 1.386(4) . ?
C15 C29 1.534(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(4) . ?
C17 C18 1.396(3) . ?
C17 C19 1.492(4) . ?
C18 C18 1.499(5) 2_655 ?
C19 C20 1.374(4) . ?
C19 C24 1.378(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.359(10) . ?
C22 H22 0.9300 . ?
C22 C23 1.316(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.402(7) . ?
C25 C26 1.510(4) . ?
C25 C27 1.524(5) . ?
C25 C28 1.487(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.518(4) . ?
C29 C31 1.523(4) . ?
C29 C32 1.536(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
