#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:17:01 +0300 (Fri, 05 May 2023) $
#$Revision: 283451 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159096.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_7159096
loop_
_publ_author_name
'Dong, Jie'
'Lei, Yu'
'Hu, Qiong'
'Zong, Lingli'
'Zhang, Ke'
'Zhang, Yajuan'
'Hu, Yimin'
_publ_section_title
;
 Fused diethynylbenzenes and phenanthrenes via arynes with
 alkynylsilanes.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2715
_journal_page_last               2719
_journal_paper_doi               10.1039/d2ob02046g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C35 H26 O4'
_chemical_formula_sum            'C35 H26 O4'
_chemical_formula_weight         510.56
_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             2022-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-22 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.370(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.511(3)
_cell_length_b                   14.995(3)
_cell_length_c                   15.259(2)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.584
_cell_measurement_theta_min      2.717
_cell_volume                     5274.2(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1646
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            101861
_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         25.998
_diffrn_reflns_theta_min         2.716
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0975 before and 0.0830 after correction. The Ratio of minimum to maximum transmission is 0.8883. The λ/2 correction factor is Not present.'
_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    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.0750
_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)+(0.0695P)²+15.9663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1883
_refine_ls_wR_factor_ref         0.2271
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3086
_reflns_number_total             5185
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02046g2.cif
_cod_data_source_block           20220912c
_cod_depositor_comments
'Adding full bibliography for 7159093--7159096.cif.'
_cod_original_cell_volume        5274.1(14)
_cod_database_code               7159096
_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   0.992
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34),
  C35(H35)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_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 0.05846(14) 0.44592(19) 0.5728(2) 0.0641(8) Uani 1 1 d . . . . .
O2 O 0.08102(13) 0.58876(18) 0.6077(2) 0.0591(8) Uani 1 1 d . . . . .
O3 O 0.09307(14) 0.3964(2) 0.3936(2) 0.0693(9) Uani 1 1 d . . . . .
O4 O 0.16321(13) 0.38122(18) 0.5434(2) 0.0599(8) Uani 1 1 d . . . . .
C1 C 0.08217(16) 0.5127(3) 0.5654(3) 0.0445(9) Uani 1 1 d . . . . .
C2 C 0.0467(2) 0.5915(3) 0.6632(4) 0.0752(14) Uani 1 1 d . . . . .
H2A H 0.007233 0.605856 0.620866 0.113 Uiso 1 1 calc GR . . . .
H2B H 0.062200 0.636182 0.712896 0.113 Uiso 1 1 calc GR . . . .
H2C H 0.048194 0.534413 0.692601 0.113 Uiso 1 1 calc GR . . . .
C3 C 0.12162(18) 0.4264(3) 0.4721(3) 0.0495(10) Uani 1 1 d . . . . .
C4 C 0.1707(2) 0.2897(3) 0.5216(4) 0.0750(14) Uani 1 1 d . . . . .
H4A H 0.180694 0.287957 0.467695 0.112 Uiso 1 1 calc GR . . . .
H4B H 0.135161 0.257613 0.505326 0.112 Uiso 1 1 calc GR . . . .
H4C H 0.201113 0.262762 0.577142 0.112 Uiso 1 1 calc GR . . . .
C5 C 0.11594(16) 0.5211(2) 0.5044(3) 0.0435(9) Uani 1 1 d . . . . .
C6 C 0.08209(17) 0.5837(2) 0.4164(3) 0.0486(9) Uani 1 1 d . . . . .
H6A H 0.083925 0.561604 0.358050 0.058 Uiso 1 1 calc R . . . .
H6B H 0.041745 0.588955 0.404842 0.058 Uiso 1 1 calc R . . . .
C7 C 0.11294(15) 0.6718(2) 0.4469(3) 0.0414(8) Uani 1 1 d . . . . .
C8 C 0.16556(15) 0.6622(2) 0.5283(2) 0.0394(8) Uani 1 1 d . . . . .
C9 C 0.17582(16) 0.5666(2) 0.5608(3) 0.0452(9) Uani 1 1 d . . . . .
H9A H 0.188233 0.562065 0.630262 0.054 Uiso 1 1 calc R . . . .
H9B H 0.205060 0.539701 0.544456 0.054 Uiso 1 1 calc R . . . .
C10 C 0.09743(16) 0.7536(2) 0.4036(3) 0.0431(9) Uani 1 1 d . . . . .
H10 H 0.062428 0.760353 0.348974 0.052 Uiso 1 1 calc R . . . .
C11 C 0.13427(15) 0.8278(2) 0.4416(3) 0.0419(8) Uani 1 1 d . . . . .
C12 C 0.11902(17) 0.9098(2) 0.3888(3) 0.0460(9) Uani 1 1 d . . . . .
H12 H 0.084515 0.912586 0.332621 0.055 Uiso 1 1 calc R . . . .
C13 C 0.15287(16) 0.9839(2) 0.4174(3) 0.0443(9) Uani 1 1 d . . . . .
C14 C 0.20331(16) 0.9823(2) 0.5088(3) 0.0433(9) Uani 1 1 d . . . . .
C15 C 0.23433(18) 1.0619(3) 0.5493(3) 0.0530(10) Uani 1 1 d . . . . .
H15 H 0.221447 1.115193 0.515716 0.064 Uiso 1 1 calc R . . . .
C16 C 0.2826(2) 1.0627(3) 0.6360(3) 0.0590(11) Uani 1 1 d . . . . .
H16 H 0.302317 1.115683 0.660930 0.071 Uiso 1 1 calc R . . . .
C17 C 0.3015(2) 0.9838(3) 0.6858(3) 0.0597(11) Uani 1 1 d . . . . .
H17 H 0.334908 0.983473 0.743830 0.072 Uiso 1 1 calc R . . . .
C18 C 0.27161(18) 0.9051(3) 0.6510(3) 0.0541(10) Uani 1 1 d . . . . .
H18 H 0.284945 0.853187 0.687032 0.065 Uiso 1 1 calc R . . . .
C19 C 0.22171(16) 0.9014(2) 0.5627(3) 0.0425(9) Uani 1 1 d . . . . .
C20 C 0.18763(15) 0.8200(2) 0.5263(2) 0.0387(8) Uani 1 1 d . . . . .
C21 C 0.20352(15) 0.7329(2) 0.5686(2) 0.0383(8) Uani 1 1 d . . . . .
C22 C 0.13941(17) 1.0617(2) 0.3498(3) 0.0490(9) Uani 1 1 d . . . . .
C23 C 0.0838(2) 1.0948(3) 0.3033(3) 0.0654(12) Uani 1 1 d . . . . .
H23 H 0.054749 1.072832 0.318776 0.079 Uiso 1 1 calc R . . . .
C24 C 0.0710(2) 1.1613(3) 0.2331(4) 0.0809(15) Uani 1 1 d . . . . .
H24 H 0.033425 1.183514 0.202310 0.097 Uiso 1 1 calc R . . . .
C25 C 0.1132(2) 1.1940(3) 0.2093(4) 0.0741(14) Uani 1 1 d . . . . .
H25 H 0.104099 1.237271 0.161375 0.089 Uiso 1 1 calc R . . . .
C26 C 0.1691(2) 1.1629(3) 0.2560(3) 0.0653(12) Uani 1 1 d . . . . .
H26 H 0.198165 1.186287 0.241408 0.078 Uiso 1 1 calc R . . . .
C27 C 0.18169(19) 1.0966(3) 0.3251(3) 0.0576(11) Uani 1 1 d . . . . .
H27 H 0.219391 1.074809 0.355647 0.069 Uiso 1 1 calc R . . . .
C28 C 0.25662(16) 0.7118(2) 0.6501(3) 0.0427(8) Uani 1 1 d . . . . .
C29 C 0.30014(17) 0.6865(3) 0.7174(3) 0.0495(9) Uani 1 1 d . . . . .
C30 C 0.35433(16) 0.6656(3) 0.7974(3) 0.0492(10) Uani 1 1 d . . . . .
C31 C 0.39863(19) 0.7292(3) 0.8315(3) 0.0641(12) Uani 1 1 d . . . . .
H31 H 0.392635 0.784933 0.801946 0.077 Uiso 1 1 calc R . . . .
C32 C 0.4508(2) 0.7105(5) 0.9080(4) 0.0896(17) Uani 1 1 d . . . . .
H32 H 0.480192 0.753061 0.930308 0.108 Uiso 1 1 calc R . . . .
C33 C 0.4592(3) 0.6271(6) 0.9517(4) 0.100(2) Uani 1 1 d . . . . .
H33 H 0.494584 0.613635 1.003224 0.120 Uiso 1 1 calc R . . . .
C34 C 0.4160(3) 0.5645(4) 0.9199(4) 0.0901(18) Uani 1 1 d . . . . .
H34 H 0.422205 0.509282 0.950421 0.108 Uiso 1 1 calc R . . . .
C35 C 0.3633(2) 0.5823(3) 0.8431(3) 0.0643(12) Uani 1 1 d . . . . .
H35 H 0.334136 0.539541 0.821922 0.077 Uiso 1 1 calc R . . . .
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 O2 C2 117.1(3) . . ?
C3 O4 C4 115.6(4) . . ?
O1 C1 O2 124.0(4) . . ?
O1 C1 C5 124.5(3) . . ?
O2 C1 C5 111.5(3) . . ?
O3 C3 O4 123.9(4) . . ?
O3 C3 C5 125.0(4) . . ?
O4 C3 C5 111.1(3) . . ?
C1 C5 C3 106.1(3) . . ?
C1 C5 C6 109.1(3) . . ?
C1 C5 C9 112.2(3) . . ?
C3 C5 C6 112.0(3) . . ?
C3 C5 C9 112.3(3) . . ?
C9 C5 C6 105.2(3) . . ?
C7 C6 C5 103.8(3) . . ?
C8 C7 C6 111.2(3) . . ?
C10 C7 C6 129.3(3) . . ?
C10 C7 C8 119.5(3) . . ?
C7 C8 C9 111.0(3) . . ?
C21 C8 C7 122.6(3) . . ?
C21 C8 C9 126.3(3) . . ?
C8 C9 C5 104.2(3) . . ?
C7 C10 C11 120.3(3) . . ?
C10 C11 C12 118.3(3) . . ?
C10 C11 C20 121.2(3) . . ?
C20 C11 C12 120.4(3) . . ?
C13 C12 C11 122.7(4) . . ?
C12 C13 C14 118.6(3) . . ?
C12 C13 C22 119.3(3) . . ?
C14 C13 C22 121.9(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 C19 118.7(3) . . ?
C19 C14 C13 120.7(3) . . ?
C16 C15 C14 122.1(4) . . ?
C15 C16 C17 118.9(4) . . ?
C16 C17 C18 121.1(4) . . ?
C17 C18 C19 121.8(4) . . ?
C14 C19 C20 119.7(3) . . ?
C18 C19 C14 117.3(3) . . ?
C18 C19 C20 123.0(3) . . ?
C11 C20 C19 117.2(3) . . ?
C11 C20 C21 117.3(3) . . ?
C21 C20 C19 125.5(3) . . ?
C8 C21 C20 119.1(3) . . ?
C8 C21 C28 116.0(3) . . ?
C28 C21 C20 124.9(3) . . ?
C23 C22 C13 121.2(4) . . ?
C23 C22 C27 118.1(4) . . ?
C27 C22 C13 120.4(4) . . ?
C22 C23 C24 120.3(4) . . ?
C25 C24 C23 120.5(5) . . ?
C24 C25 C26 120.1(4) . . ?
C25 C26 C27 119.4(4) . . ?
C26 C27 C22 121.6(4) . . ?
C29 C28 C21 174.4(4) . . ?
C28 C29 C30 173.9(4) . . ?
C31 C30 C29 119.9(4) . . ?
C31 C30 C35 119.3(4) . . ?
C35 C30 C29 120.8(4) . . ?
C32 C31 C30 120.8(5) . . ?
C31 C32 C33 119.0(6) . . ?
C34 C33 C32 120.8(5) . . ?
C33 C34 C35 120.8(6) . . ?
C34 C35 C30 119.2(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 1.200(4) . ?
O2 C1 1.316(4) . ?
O2 C2 1.456(5) . ?
O3 C3 1.191(5) . ?
O4 C3 1.334(5) . ?
O4 C4 1.443(5) . ?
C1 C5 1.520(5) . ?
C3 C5 1.531(5) . ?
C5 C6 1.561(5) . ?
C5 C9 1.553(5) . ?
C6 C7 1.506(5) . ?
C7 C8 1.392(5) . ?
C7 C10 1.369(5) . ?
C8 C9 1.502(5) . ?
C8 C21 1.389(5) . ?
C10 C11 1.410(5) . ?
C11 C12 1.430(5) . ?
C11 C20 1.425(5) . ?
C12 C13 1.359(5) . ?
C13 C14 1.437(5) . ?
C13 C22 1.496(5) . ?
C14 C15 1.418(5) . ?
C14 C19 1.427(5) . ?
C15 C16 1.368(6) . ?
C16 C17 1.377(6) . ?
C17 C18 1.381(5) . ?
C18 C19 1.403(5) . ?
C19 C20 1.464(5) . ?
C20 C21 1.436(5) . ?
C21 C28 1.427(5) . ?
C22 C23 1.378(6) . ?
C22 C27 1.389(5) . ?
C23 C24 1.395(6) . ?
C24 C25 1.367(7) . ?
C25 C26 1.373(6) . ?
C26 C27 1.383(6) . ?
C28 C29 1.206(5) . ?
C29 C30 1.433(5) . ?
C30 C31 1.398(6) . ?
C30 C35 1.400(6) . ?
C31 C32 1.372(7) . ?
C32 C33 1.391(9) . ?
C33 C34 1.369(9) . ?
C34 C35 1.378(7) . ?
