#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:57:32 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257916 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157581.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_7157581
loop_
_publ_author_name
'Takano, Hideaki'
'Okazaki, Sari'
'Nishibe, Shun'
'Ito, Takeharu'
'Shiozawa, Natsumi'
'Sugimura, Natsuhiko'
'Kanyiva, Kyalo Stephen'
'Shibata, Takanori'
_publ_section_title
;
 Gold-catalyzed dual C-C bond cleavage of biphenylenes bearing a pendant
 alkyne at ambient temperature.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5826
_journal_page_last               5831
_journal_paper_doi               10.1039/d0ob01211d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C23 H17 Cl'
_chemical_formula_sum            'C23 H17 Cl'
_chemical_formula_weight         328.84
_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     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-03-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.847(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   19.2706(14)
_cell_length_b                   4.9741(4)
_cell_length_c                   33.688(2)
_cell_measurement_reflns_used    6084
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      4.60
_cell_volume                     3148.3(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            8088
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         4.707
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376.00
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1933
_refine_ls_R_factor_gt           0.0883
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+2.6954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1546
_reflns_number_total             2695
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d0ob01211d2.cif
_cod_data_source_block           20191203_propyl_TM-A
_cod_depositor_comments
;Adding full bibliography for 7157579--7157581.cif.

 Adding full bibliography for 7157579--7157581.cif.
;
_cod_database_code               7157581
_shelxl_version_number           2014/6
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
Cl1 Cl 0.41947(5) -0.23507(18) 0.29042(3) 0.0440(4) Uani 1 1 d . . . . .
C1 C 0.67150(18) 0.6051(7) 0.34950(10) 0.0273(9) Uani 1 1 d . . . . .
C2 C 0.76206(19) 0.6534(7) 0.31161(10) 0.0307(9) Uani 1 1 d . . . . .
H2 H 0.8038 0.7362 0.3068 0.037 Uiso 1 1 calc R U . . .
C3 C 0.63589(18) 0.4067(7) 0.32422(10) 0.0301(9) Uani 1 1 d . . . . .
C4 C 0.48741(19) 0.3012(7) 0.37784(11) 0.0345(10) Uani 1 1 d . . . . .
H4 H 0.4723 0.3655 0.4011 0.041 Uiso 1 1 calc R U . . .
C5 C 0.75469(19) 0.9274(7) 0.37656(10) 0.0290(9) Uani 1 1 d . . . . .
C6 C 0.73395(18) 0.7307(7) 0.34395(11) 0.0281(9) Uani 1 1 d . . . . .
C7 C 0.66628(19) 0.3281(7) 0.29152(10) 0.0329(10) Uani 1 1 d . . . . .
H7 H 0.6444 0.1911 0.2733 0.039 Uiso 1 1 calc R U . . .
C8 C 0.44799(18) 0.1082(7) 0.35458(11) 0.0331(9) Uani 1 1 d . . . . .
H8 H 0.4058 0.0419 0.3613 0.040 Uiso 1 1 calc R U . . .
C9 C 0.71504(19) 1.0860(7) 0.43570(10) 0.0321(9) Uani 1 1 d . . . . .
H9 H 0.6833 1.0803 0.4536 0.039 Uiso 1 1 calc R U . . .
C10 C 0.47035(19) 0.0083(7) 0.32064(10) 0.0328(10) Uani 1 1 d . . . . .
C11 C 0.54997(19) 0.4104(7) 0.36883(11) 0.0323(9) Uani 1 1 d . . . . .
C12 C 0.81914(19) 1.2734(7) 0.41769(11) 0.0345(10) Uani 1 1 d . . . . .
H12 H 0.8576 1.3973 0.4232 0.041 Uiso 1 1 calc R U . . .
C13 C 0.70467(18) 0.9161(7) 0.40220(10) 0.0280(9) Uani 1 1 d . . . . .
C14 C 0.53098(18) 0.1040(7) 0.31071(10) 0.0331(10) Uani 1 1 d . . . . .
H14 H 0.5453 0.0347 0.2875 0.040 Uiso 1 1 calc R U . . .
C15 C 0.7276(2) 0.4502(7) 0.28603(10) 0.0353(10) Uani 1 1 d . . . . .
H15 H 0.7473 0.3939 0.2639 0.042 Uiso 1 1 calc R U . . .
C16 C 0.56568(18) 0.7365(7) 0.43097(10) 0.0327(10) Uani 1 1 d . . . . .
H16A H 0.5769 0.9309 0.4331 0.039 Uiso 1 1 calc R U . . .
H16B H 0.5134 0.7175 0.4264 0.039 Uiso 1 1 calc R U . . .
C17 C 0.59982(18) 0.6020(7) 0.47108(10) 0.0356(10) Uani 1 1 d . . . . .
H17A H 0.6522 0.6085 0.4749 0.043 Uiso 1 1 calc R U . . .
H17B H 0.5853 0.4108 0.4701 0.043 Uiso 1 1 calc R U . . .
C18 C 0.58981(19) 0.6223(7) 0.39436(11) 0.0330(9) Uani 1 1 d . . . . .
C19 C 0.81093(19) 1.1040(7) 0.38439(10) 0.0321(9) Uani 1 1 d . . . . .
H19 H 0.8438 1.1096 0.3672 0.039 Uiso 1 1 calc R U . . .
C20 C 0.6502(2) 0.7129(7) 0.38473(10) 0.0318(10) Uani 1 1 d . . . . .
C21 C 0.5786(2) 0.7374(7) 0.50696(10) 0.0427(11) Uani 1 1 d . . . . .
H21A H 0.6016 0.6453 0.5322 0.051 Uiso 1 1 calc R U . . .
H21B H 0.5937 0.9260 0.5084 0.051 Uiso 1 1 calc R U . . .
H21C H 0.5268 0.7284 0.5035 0.051 Uiso 1 1 calc R U . . .
C22 C 0.7715(2) 1.2630(7) 0.44300(11) 0.0338(10) Uani 1 1 d . . . . .
H22 H 0.7778 1.3801 0.4658 0.041 Uiso 1 1 calc R U . . .
C23 C 0.57187(19) 0.3015(7) 0.33424(11) 0.0283(9) 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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(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
C3 C1 C6 123.9(3) . . ?
C3 C1 C20 125.4(3) . . ?
C6 C1 C20 110.6(3) . . ?
C6 C2 C15 118.3(3) . . ?
C6 C2 H2 120.8 . . ?
C15 C2 H2 120.8 . . ?
C1 C3 C7 116.3(3) . . ?
C1 C3 C23 116.5(3) . . ?
C7 C3 C23 127.2(3) . . ?
C8 C4 C11 122.7(4) . . ?
C8 C4 H4 118.6 . . ?
C11 C4 H4 118.6 . . ?
C19 C5 C13 121.2(3) . . ?
C19 C5 C6 130.2(3) . . ?
C13 C5 C6 108.6(3) . . ?
C2 C6 C1 118.8(3) . . ?
C2 C6 C5 133.9(3) . . ?
C1 C6 C5 107.3(3) . . ?
C15 C7 C3 120.0(3) . . ?
C15 C7 H7 120.0 . . ?
C3 C7 H7 120.0 . . ?
C4 C8 C10 119.2(3) . . ?
C4 C8 H8 120.4 . . ?
C10 C8 H8 120.4 . . ?
C22 C9 C13 119.9(3) . . ?
C22 C9 H9 120.0 . . ?
C13 C9 H9 120.0 . . ?
C14 C10 C8 120.7(3) . . ?
C14 C10 Cl1 120.0(3) . . ?
C8 C10 Cl1 119.3(3) . . ?
C4 C11 C23 116.7(3) . . ?
C4 C11 C18 120.7(3) . . ?
C23 C11 C18 122.6(3) . . ?
C22 C12 C19 120.2(3) . . ?
C22 C12 H12 119.9 . . ?
C19 C12 H12 119.9 . . ?
C9 C13 C5 118.2(3) . . ?
C9 C13 C20 134.4(3) . . ?
C5 C13 C20 107.4(3) . . ?
C10 C14 C23 120.8(3) . . ?
C10 C14 H14 119.6 . . ?
C23 C14 H14 119.6 . . ?
C7 C15 C2 122.7(3) . . ?
C7 C15 H15 118.6 . . ?
C2 C15 H15 118.6 . . ?
C17 C16 C18 114.0(3) . . ?
C17 C16 H16A 108.8 . . ?
C18 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C18 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C21 111.9(3) . . ?
C16 C17 H17A 109.2 . . ?
C21 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C21 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C20 C18 C11 117.7(3) . . ?
C20 C18 C16 120.3(3) . . ?
C11 C18 C16 122.0(3) . . ?
C5 C19 C12 119.2(3) . . ?
C5 C19 H19 120.4 . . ?
C12 C19 H19 120.4 . . ?
C18 C20 C1 119.4(3) . . ?
C18 C20 C13 134.7(3) . . ?
C1 C20 C13 106.0(3) . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C22 C12 121.3(3) . . ?
C9 C22 H22 119.4 . . ?
C12 C22 H22 119.4 . . ?
C14 C23 C11 119.9(3) . . ?
C14 C23 C3 121.8(3) . . ?
C11 C23 C3 118.3(3) . . ?
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
Cl1 C10 1.737(3) . ?
C1 C3 1.382(4) . ?
C1 C6 1.405(4) . ?
C1 C20 1.442(4) . ?
C2 C6 1.375(4) . ?
C2 C15 1.396(4) . ?
C2 H2 0.9500 . ?
C3 C7 1.413(4) . ?
C3 C23 1.447(5) . ?
C4 C8 1.360(4) . ?
C4 C11 1.415(5) . ?
C4 H4 0.9500 . ?
C5 C19 1.374(4) . ?
C5 C13 1.431(4) . ?
C5 C6 1.459(5) . ?
C7 C15 1.377(5) . ?
C7 H7 0.9500 . ?
C8 C10 1.399(4) . ?
C8 H8 0.9500 . ?
C9 C22 1.378(4) . ?
C9 C13 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C14 1.370(4) . ?
C11 C23 1.431(5) . ?
C11 C18 1.465(5) . ?
C12 C22 1.386(5) . ?
C12 C19 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C20 1.481(5) . ?
C14 C23 1.391(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.520(4) . ?
C16 C18 1.522(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C21 1.517(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C20 1.354(4) . ?
C19 H19 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 0.9500 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C3 C7 1.0(5) . . . . ?
C20 C1 C3 C7 -179.4(3) . . . . ?
C6 C1 C3 C23 -179.3(3) . . . . ?
C20 C1 C3 C23 0.3(5) . . . . ?
C15 C2 C6 C1 -0.9(5) . . . . ?
C15 C2 C6 C5 179.2(3) . . . . ?
C3 C1 C6 C2 -0.1(5) . . . . ?
C20 C1 C6 C2 -179.8(3) . . . . ?
C3 C1 C6 C5 179.8(3) . . . . ?
C20 C1 C6 C5 0.1(4) . . . . ?
C19 C5 C6 C2 1.0(6) . . . . ?
C13 C5 C6 C2 -179.2(3) . . . . ?
C19 C5 C6 C1 -178.9(3) . . . . ?
C13 C5 C6 C1 0.9(4) . . . . ?
C1 C3 C7 C15 -0.7(5) . . . . ?
C23 C3 C7 C15 179.6(3) . . . . ?
C11 C4 C8 C10 1.2(5) . . . . ?
C4 C8 C10 C14 -0.3(5) . . . . ?
C4 C8 C10 Cl1 -179.1(3) . . . . ?
C8 C4 C11 C23 -1.9(5) . . . . ?
C8 C4 C11 C18 178.7(3) . . . . ?
C22 C9 C13 C5 1.3(5) . . . . ?
C22 C9 C13 C20 -177.7(3) . . . . ?
C19 C5 C13 C9 -1.0(5) . . . . ?
C6 C5 C13 C9 179.2(3) . . . . ?
C19 C5 C13 C20 178.4(3) . . . . ?
C6 C5 C13 C20 -1.5(4) . . . . ?
C8 C10 C14 C23 0.4(5) . . . . ?
Cl1 C10 C14 C23 179.1(2) . . . . ?
C3 C7 C15 C2 -0.3(5) . . . . ?
C6 C2 C15 C7 1.1(5) . . . . ?
C18 C16 C17 C21 175.4(3) . . . . ?
C4 C11 C18 C20 178.2(3) . . . . ?
C23 C11 C18 C20 -1.1(5) . . . . ?
C4 C11 C18 C16 -0.8(5) . . . . ?
C23 C11 C18 C16 179.8(3) . . . . ?
C17 C16 C18 C20 -84.8(4) . . . . ?
C17 C16 C18 C11 94.2(4) . . . . ?
C13 C5 C19 C12 0.0(5) . . . . ?
C6 C5 C19 C12 179.8(3) . . . . ?
C22 C12 C19 C5 0.6(5) . . . . ?
C11 C18 C20 C1 2.0(5) . . . . ?
C16 C18 C20 C1 -179.0(3) . . . . ?
C11 C18 C20 C13 -179.4(3) . . . . ?
C16 C18 C20 C13 -0.3(6) . . . . ?
C3 C1 C20 C18 -1.7(5) . . . . ?
C6 C1 C20 C18 178.0(3) . . . . ?
C3 C1 C20 C13 179.3(3) . . . . ?
C6 C1 C20 C13 -1.0(4) . . . . ?
C9 C13 C20 C18 1.9(7) . . . . ?
C5 C13 C20 C18 -177.3(4) . . . . ?
C9 C13 C20 C1 -179.4(4) . . . . ?
C5 C13 C20 C1 1.5(4) . . . . ?
C13 C9 C22 C12 -0.8(5) . . . . ?
C19 C12 C22 C9 -0.2(5) . . . . ?
C10 C14 C23 C11 -1.2(5) . . . . ?
C10 C14 C23 C3 -179.7(3) . . . . ?
C4 C11 C23 C14 1.9(5) . . . . ?
C18 C11 C23 C14 -178.7(3) . . . . ?
C4 C11 C23 C3 -179.6(3) . . . . ?
C18 C11 C23 C3 -0.2(5) . . . . ?
C1 C3 C23 C14 179.1(3) . . . . ?
C7 C3 C23 C14 -1.3(5) . . . . ?
C1 C3 C23 C11 0.6(5) . . . . ?
C7 C3 C23 C11 -179.8(3) . . . . ?
