#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:57:32 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257916 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157580.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_7157580
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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                113.594(8)
_cell_angle_beta                 103.447(7)
_cell_angle_gamma                93.898(7)
_cell_formula_units_Z            2
_cell_length_a                   7.5655(2)
_cell_length_b                   10.9027(3)
_cell_length_c                   11.0880(3)
_cell_measurement_reflns_used    8765
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.50
_cell_volume                     801.74(8)
_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      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.976
_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  0.0694
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       -9999
_diffrn_reflns_limit_h_min       9999
_diffrn_reflns_limit_k_max       -9999
_diffrn_reflns_limit_k_min       9999
_diffrn_reflns_limit_l_max       -9999
_diffrn_reflns_limit_l_min       9999
_diffrn_reflns_number            9006
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.226
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.075
_exptl_absorpt_correction_T_max  0.660
_exptl_absorpt_correction_T_min  0.333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             344.00
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0603P)²+0.3581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2580
_reflns_number_total             2855
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d0ob01211d2.cif
_cod_data_source_block           20191223takano_enyne_iPr
_cod_depositor_comments
;Adding full bibliography for 7157579--7157581.cif.

 Adding full bibliography for 7157579--7157581.cif.
;
_cod_database_code               7157580
_shelxl_version_number           2014/6
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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_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 0.24297(7) 0.58611(5) 0.13555(5) 0.03289(19) Uani 1 1 d . . . . .
C1 C 0.3990(3) 0.67194(18) 0.67334(19) 0.0223(4) Uani 1 1 d . . . . .
C2 C 0.2532(3) 0.46605(18) 0.6644(2) 0.0230(4) Uani 1 1 d . . . . .
C3 C 0.4950(3) 0.80349(18) 0.68042(19) 0.0231(4) Uani 1 1 d . . . . .
C4 C 0.2946(3) 0.54280(18) 0.59116(19) 0.0220(4) Uani 1 1 d . . . . .
C5 C 0.2656(3) 0.55458(19) 0.36741(19) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.3361 0.6418 0.4127 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4620(3) 0.72429(19) 0.8170(2) 0.0249(4) Uani 1 1 d . . . . .
C7 C 0.1211(3) 0.35159(19) 0.3717(2) 0.0246(4) Uani 1 1 d . . . . .
C8 C 0.3202(3) 0.5219(2) 0.8081(2) 0.0262(4) Uani 1 1 d . . . . .
H8 H 0.2927 0.4694 0.8522 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5582(3) 0.85477(19) 0.8256(2) 0.0246(4) Uani 1 1 d . . . . .
C10 C 0.5399(3) 0.87704(19) 0.6135(2) 0.0274(4) Uani 1 1 d . . . . .
H10 H 0.4998 0.8438 0.5184 0.033 Uiso 1 1 calc R U . . .
C11 C 0.0781(3) 0.28002(19) 0.4484(2) 0.0270(4) Uani 1 1 d . . . . .
H11 H 0.0042 0.1941 0.4004 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1396(3) 0.33110(19) 0.5866(2) 0.0249(4) Uani 1 1 d . . . . .
C13 C 0.1983(3) 0.4950(2) 0.2271(2) 0.0262(4) Uani 1 1 d . . . . .
C14 C 0.2281(3) 0.48375(18) 0.44254(19) 0.0227(4) Uani 1 1 d . . . . .
C15 C 0.7117(3) 1.0558(2) 0.8376(2) 0.0320(5) Uani 1 1 d . . . . .
H15 H 0.7849 1.1418 0.8885 0.038 Uiso 1 1 calc R U . . .
C16 C 0.0951(3) 0.3641(2) 0.1554(2) 0.0301(5) Uani 1 1 d . . . . .
H16 H 0.0526 0.3248 0.0601 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6660(3) 0.9792(2) 0.9071(2) 0.0296(5) Uani 1 1 d . . . . .
H17 H 0.7071 1.0118 1.0020 0.035 Uiso 1 1 calc R U . . .
C18 C 0.2428(3) 0.1705(2) 0.6922(2) 0.0291(5) Uani 1 1 d . . . . .
H18A H 0.2545 0.1011 0.6075 0.035 Uiso 1 1 calc R U . . .
H18B H 0.3596 0.2336 0.7388 0.035 Uiso 1 1 calc R U . . .
C19 C 0.0909(3) 0.24692(19) 0.6582(2) 0.0280(5) Uani 1 1 d . . . . .
H19A H -0.0215 0.1816 0.6001 0.034 Uiso 1 1 calc R U . . .
H19B H 0.0663 0.3062 0.7426 0.034 Uiso 1 1 calc R U . . .
C20 C 0.0569(3) 0.2937(2) 0.2276(2) 0.0303(5) Uani 1 1 d . . . . .
H20 H -0.0126 0.2062 0.1804 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6511(3) 1.0069(2) 0.6979(2) 0.0310(5) Uani 1 1 d . . . . .
H21 H 0.6842 1.0610 0.6568 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4253(3) 0.6514(2) 0.8878(2) 0.0278(4) Uani 1 1 d . . . . .
H22 H 0.4682 0.6866 0.9829 0.033 Uiso 1 1 calc R U . . .
C23 C 0.2034(3) 0.1038(2) 0.7824(2) 0.0329(5) Uani 1 1 d . . . . .
H23A H 0.3019 0.0571 0.8011 0.039 Uiso 1 1 calc R U . . .
H23B H 0.1941 0.1722 0.8672 0.039 Uiso 1 1 calc R U . . .
H23C H 0.0891 0.0398 0.7359 0.039 Uiso 1 1 calc R U . . .
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
C4 C1 C6 122.81(17) . . ?
C4 C1 C3 147.30(18) . . ?
C6 C1 C3 89.88(15) . . ?
C8 C2 C4 120.32(17) . . ?
C8 C2 C12 120.96(17) . . ?
C4 C2 C12 118.71(17) . . ?
C10 C3 C9 121.64(17) . . ?
C10 C3 C1 148.88(18) . . ?
C9 C3 C1 89.45(15) . . ?
C1 C4 C2 114.98(17) . . ?
C1 C4 C14 124.86(17) . . ?
C2 C4 C14 120.16(16) . . ?
C13 C5 C14 119.87(18) . . ?
C13 C5 H5 120.1 . . ?
C14 C5 H5 120.1 . . ?
C22 C6 C1 122.67(18) . . ?
C22 C6 C9 146.59(18) . . ?
C1 C6 C9 90.71(15) . . ?
C20 C7 C14 119.14(18) . . ?
C20 C7 C11 121.55(18) . . ?
C14 C7 C11 119.30(17) . . ?
C22 C8 C2 123.45(17) . . ?
C22 C8 H8 118.3 . . ?
C2 C8 H8 118.3 . . ?
C17 C9 C3 122.80(18) . . ?
C17 C9 C6 147.22(18) . . ?
C3 C9 C6 89.96(15) . . ?
C3 C10 C21 115.78(18) . . ?
C3 C10 H10 122.1 . . ?
C21 C10 H10 122.1 . . ?
C12 C11 C7 123.37(17) . . ?
C12 C11 H11 118.3 . . ?
C7 C11 H11 118.3 . . ?
C11 C12 C2 119.48(17) . . ?
C11 C12 C19 119.62(17) . . ?
C2 C12 C19 120.89(17) . . ?
C5 C13 C16 121.85(18) . . ?
C5 C13 Cl1 119.17(15) . . ?
C16 C13 Cl1 118.98(15) . . ?
C5 C14 C7 119.07(17) . . ?
C5 C14 C4 121.99(17) . . ?
C7 C14 C4 118.93(17) . . ?
C21 C15 C17 121.85(18) . . ?
C21 C15 H15 119.1 . . ?
C17 C15 H15 119.1 . . ?
C20 C16 C13 118.93(18) . . ?
C20 C16 H16 120.5 . . ?
C13 C16 H16 120.5 . . ?
C9 C17 C15 115.54(18) . . ?
C9 C17 H17 122.2 . . ?
C15 C17 H17 122.2 . . ?
C23 C18 C19 112.29(17) . . ?
C23 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C23 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C12 C19 C18 113.31(16) . . ?
C12 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C12 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C16 C20 C7 121.12(18) . . ?
C16 C20 H20 119.4 . . ?
C7 C20 H20 119.4 . . ?
C15 C21 C10 122.38(18) . . ?
C15 C21 H21 118.8 . . ?
C10 C21 H21 118.8 . . ?
C6 C22 C8 115.75(18) . . ?
C6 C22 H22 122.1 . . ?
C8 C22 H22 122.1 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Cl1 C13 1.747(2) . ?
C1 C4 1.387(3) . ?
C1 C6 1.405(3) . ?
C1 C3 1.527(3) . ?
C2 C8 1.404(3) . ?
C2 C4 1.444(2) . ?
C2 C12 1.454(3) . ?
C3 C10 1.366(3) . ?
C3 C9 1.420(3) . ?
C4 C14 1.451(3) . ?
C5 C13 1.371(3) . ?
C5 C14 1.402(3) . ?
C5 H5 0.9300 . ?
C6 C22 1.377(3) . ?
C6 C9 1.511(3) . ?
C7 C20 1.407(3) . ?
C7 C14 1.410(3) . ?
C7 C11 1.436(3) . ?
C8 C22 1.388(3) . ?
C8 H8 0.9300 . ?
C9 C17 1.359(3) . ?
C10 C21 1.414(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.352(3) . ?
C11 H11 0.9300 . ?
C12 C19 1.510(2) . ?
C13 C16 1.389(3) . ?
C15 C21 1.367(3) . ?
C15 C17 1.418(3) . ?
C15 H15 0.9300 . ?
C16 C20 1.372(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.520(3) . ?
C18 C19 1.529(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
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
C4 C1 C3 C10 -0.5(6) . . . . ?
C6 C1 C3 C10 177.9(3) . . . . ?
C4 C1 C3 C9 -178.2(3) . . . . ?
C6 C1 C3 C9 0.21(16) . . . . ?
C6 C1 C4 C2 0.6(3) . . . . ?
C3 C1 C4 C2 178.8(3) . . . . ?
C6 C1 C4 C14 -179.31(17) . . . . ?
C3 C1 C4 C14 -1.2(4) . . . . ?
C8 C2 C4 C1 -1.1(3) . . . . ?
C12 C2 C4 C1 178.19(17) . . . . ?
C8 C2 C4 C14 178.82(17) . . . . ?
C12 C2 C4 C14 -1.9(3) . . . . ?
C4 C1 C6 C22 0.1(3) . . . . ?
C3 C1 C6 C22 -178.85(19) . . . . ?
C4 C1 C6 C9 178.79(19) . . . . ?
C3 C1 C6 C9 -0.20(15) . . . . ?
C4 C2 C8 C22 0.9(3) . . . . ?
C12 C2 C8 C22 -178.38(18) . . . . ?
C10 C3 C9 C17 0.2(3) . . . . ?
C1 C3 C9 C17 178.8(2) . . . . ?
C10 C3 C9 C6 -178.82(18) . . . . ?
C1 C3 C9 C6 -0.19(14) . . . . ?
C22 C6 C9 C17 -0.3(6) . . . . ?
C1 C6 C9 C17 -178.2(3) . . . . ?
C22 C6 C9 C3 178.2(3) . . . . ?
C1 C6 C9 C3 0.21(16) . . . . ?
C9 C3 C10 C21 -0.5(3) . . . . ?
C1 C3 C10 C21 -177.9(3) . . . . ?
C20 C7 C11 C12 178.84(19) . . . . ?
C14 C7 C11 C12 -2.0(3) . . . . ?
C7 C11 C12 C2 0.9(3) . . . . ?
C7 C11 C12 C19 -178.58(17) . . . . ?
C8 C2 C12 C11 -179.67(18) . . . . ?
C4 C2 C12 C11 1.0(3) . . . . ?
C8 C2 C12 C19 -0.2(3) . . . . ?
C4 C2 C12 C19 -179.50(16) . . . . ?
C14 C5 C13 C16 -1.1(3) . . . . ?
C14 C5 C13 Cl1 178.83(14) . . . . ?
C13 C5 C14 C7 0.0(3) . . . . ?
C13 C5 C14 C4 -179.36(18) . . . . ?
C20 C7 C14 C5 0.8(3) . . . . ?
C11 C7 C14 C5 -178.36(16) . . . . ?
C20 C7 C14 C4 -179.76(17) . . . . ?
C11 C7 C14 C4 1.1(3) . . . . ?
C1 C4 C14 C5 0.2(3) . . . . ?
C2 C4 C14 C5 -179.78(17) . . . . ?
C1 C4 C14 C7 -179.24(18) . . . . ?
C2 C4 C14 C7 0.8(3) . . . . ?
C5 C13 C16 C20 1.2(3) . . . . ?
Cl1 C13 C16 C20 -178.70(15) . . . . ?
C3 C9 C17 C15 0.2(3) . . . . ?
C6 C9 C17 C15 178.3(3) . . . . ?
C21 C15 C17 C9 -0.2(3) . . . . ?
C11 C12 C19 C18 97.1(2) . . . . ?
C2 C12 C19 C18 -82.4(2) . . . . ?
C23 C18 C19 C12 171.48(17) . . . . ?
C13 C16 C20 C7 -0.3(3) . . . . ?
C14 C7 C20 C16 -0.7(3) . . . . ?
C11 C7 C20 C16 178.47(18) . . . . ?
C17 C15 C21 C10 -0.2(3) . . . . ?
C3 C10 C21 C15 0.6(3) . . . . ?
C1 C6 C22 C8 -0.4(3) . . . . ?
C9 C6 C22 C8 -178.0(3) . . . . ?
C2 C8 C22 C6 -0.1(3) . . . . ?
