#------------------------------------------------------------------------------
#$Date: 2020-10-20 01:43:44 +0300 (Tue, 20 Oct 2020) $
#$Revision: 258464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135298.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_4135298
loop_
_publ_author_name
'Bakhoda, Abolghasem'
'Okoromoba, Otome E.'
'Greene, Christine'
'Raghibi Boroujeni, Mahdi'
'Bertke, Jeffery A.'
'Warren, Timothy H.'
_publ_section_title
;
 A Three Coordinate Copper(II) Alkynyl Complex in C-C Bond Formation: The
 Sesquicentennial of the Glaser Coupling.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c07137
_journal_year                    2020
_chemical_formula_moiety         'C27 H18 Cl2'
_chemical_formula_sum            'C27 H18 Cl2'
_chemical_formula_weight         413.31
_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     intrinisic
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                103.367(9)
_cell_angle_beta                 93.159(14)
_cell_angle_gamma                116.101(10)
_cell_formula_units_Z            2
_cell_length_a                   8.401(4)
_cell_length_b                   8.962(4)
_cell_length_c                   15.780(8)
_cell_measurement_reflns_used    5368
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.60
_cell_volume                     1021.2(9)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_collection       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_data_reduction
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9740
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.340
_diffrn_reflns_theta_min         2.600
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0368P)²+0.4147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3337
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c07137_si_004.cif
_cod_data_source_block           P1bar_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4135298
_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_min   0.937
_shelx_estimated_absorpt_t_max   0.952
loop_
_space_group_symop_operation_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_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 0.22701(6) 0.28691(5) 0.49690(2) 0.03003(12) Uani 1 1 d . . . . .
Cl2 Cl 0.27395(7) 0.87481(5) 0.43742(3) 0.03683(13) Uani 1 1 d . . . . .
C1 C 0.25174(18) 0.58677(17) 0.47464(9) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.22691(19) 0.48550(19) 0.53338(9) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.2020(2) 0.5385(2) 0.61939(9) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.184242 0.466790 0.657530 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2034(2) 0.6970(2) 0.64877(9) 0.0262(3) Uani 1 1 d . . . . .
H4 H 0.186863 0.734256 0.707522 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2287(2) 0.8017(2) 0.59352(10) 0.0275(3) Uani 1 1 d . . . . .
H5 H 0.231412 0.911195 0.614319 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2502(2) 0.74538(19) 0.50745(9) 0.0225(3) Uani 1 1 d . . . . .
C7 C 0.27550(18) 0.53142(17) 0.38571(9) 0.0170(3) Uani 1 1 d . . . . .
C8 C 0.29537(17) 0.48782(16) 0.31108(9) 0.0145(3) Uani 1 1 d . . . . .
C9 C 0.31746(17) 0.43091(16) 0.21854(8) 0.0135(3) Uani 1 1 d . . . . .
C10 C 0.34913(17) 0.27064(16) 0.20865(8) 0.0131(3) Uani 1 1 d . . . . .
C11 C 0.46804(18) 0.24261(16) 0.15684(9) 0.0158(3) Uani 1 1 d . . . . .
H11 H 0.534345 0.324932 0.127086 0.019 Uiso 1 1 calc R U . . .
C12 C 0.49065(19) 0.09509(17) 0.14824(9) 0.0188(3) Uani 1 1 d . . . . .
H12 H 0.572499 0.077749 0.112997 0.023 Uiso 1 1 calc R U . . .
C13 C 0.39379(19) -0.02663(17) 0.19110(9) 0.0194(3) Uani 1 1 d . . . . .
H13 H 0.409799 -0.126733 0.185747 0.023 Uiso 1 1 calc R U . . .
C14 C 0.27341(19) -0.00073(17) 0.24181(9) 0.0203(3) Uani 1 1 d . . . . .
H14 H 0.205305 -0.084612 0.270384 0.024 Uiso 1 1 calc R U . . .
C15 C 0.25172(19) 0.14684(17) 0.25111(9) 0.0176(3) Uani 1 1 d . . . . .
H15 H 0.170043 0.163788 0.286611 0.021 Uiso 1 1 calc R U . . .
C16 C 0.48097(17) 0.58140(16) 0.19878(8) 0.0129(3) Uani 1 1 d . . . . .
C17 C 0.48605(18) 0.60335(17) 0.11403(9) 0.0151(3) Uani 1 1 d . . . . .
H17 H 0.386713 0.526463 0.067530 0.018 Uiso 1 1 calc R U . . .
C18 C 0.63528(19) 0.73684(17) 0.09690(9) 0.0182(3) Uani 1 1 d . . . . .
H18 H 0.636097 0.750847 0.039035 0.022 Uiso 1 1 calc R U . . .
C19 C 0.78288(19) 0.84962(17) 0.16375(10) 0.0201(3) Uani 1 1 d . . . . .
H19 H 0.884429 0.940568 0.151966 0.024 Uiso 1 1 calc R U . . .
C20 C 0.77984(19) 0.82749(17) 0.24807(9) 0.0196(3) Uani 1 1 d . . . . .
H20 H 0.880827 0.902699 0.294001 0.023 Uiso 1 1 calc R U . . .
C21 C 0.62970(18) 0.69574(17) 0.26577(9) 0.0169(3) Uani 1 1 d . . . . .
H21 H 0.628416 0.683510 0.323980 0.020 Uiso 1 1 calc R U . . .
C22 C 0.14359(17) 0.38541(16) 0.15608(8) 0.0135(3) Uani 1 1 d . . . . .
C23 C 0.06423(18) 0.49494(17) 0.17286(9) 0.0170(3) Uani 1 1 d . . . . .
H23 H 0.111798 0.590394 0.224818 0.020 Uiso 1 1 calc R U . . .
C24 C -0.08318(19) 0.46615(18) 0.11464(9) 0.0197(3) Uani 1 1 d . . . . .
H24 H -0.135446 0.541940 0.126809 0.024 Uiso 1 1 calc R U . . .
C25 C -0.15450(19) 0.32620(18) 0.03839(9) 0.0199(3) Uani 1 1 d . . . . .
H25 H -0.255012 0.306554 -0.001668 0.024 Uiso 1 1 calc R U . . .
C26 C -0.07797(19) 0.21587(17) 0.02133(9) 0.0191(3) Uani 1 1 d . . . . .
H26 H -0.126732 0.119851 -0.030386 0.023 Uiso 1 1 calc R U . . .
C27 C 0.07051(18) 0.24517(17) 0.07981(9) 0.0158(3) Uani 1 1 d . . . . .
H27 H 0.122211 0.168921 0.067538 0.019 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 116.29(13) . . ?
C6 C1 C7 121.47(12) . . ?
C2 C1 C7 122.23(13) . . ?
C3 C2 C1 122.19(14) . . ?
C3 C2 Cl1 119.11(11) . . ?
C1 C2 Cl1 118.70(11) . . ?
C4 C3 C2 119.21(14) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.65(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.37(14) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 122.27(14) . . ?
C5 C6 Cl2 118.93(12) . . ?
C1 C6 Cl2 118.80(11) . . ?
C8 C7 C1 178.78(14) . . ?
C7 C8 C9 179.04(14) . . ?
C8 C9 C10 107.94(10) . . ?
C8 C9 C22 108.28(11) . . ?
C10 C9 C22 111.12(10) . . ?
C8 C9 C16 109.08(10) . . ?
C10 C9 C16 110.73(11) . . ?
C22 C9 C16 109.62(10) . . ?
C11 C10 C15 118.61(12) . . ?
C11 C10 C9 122.35(11) . . ?
C15 C10 C9 119.02(12) . . ?
C12 C11 C10 120.72(12) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.16(13) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.43(13) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.53(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.54(13) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C21 118.37(12) . . ?
C17 C16 C9 121.38(12) . . ?
C21 C16 C9 120.22(12) . . ?
C18 C17 C16 120.73(12) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.57(13) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.08(13) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 120.50(13) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.74(13) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C27 C22 C23 118.56(12) . . ?
C27 C22 C9 122.06(12) . . ?
C23 C22 C9 119.22(12) . . ?
C24 C23 C22 120.91(13) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.05(13) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 119.61(13) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.28(13) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C22 C27 C26 120.58(13) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
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 C2 1.7398(17) . ?
Cl2 C6 1.7377(16) . ?
C1 C6 1.402(2) . ?
C1 C2 1.404(2) . ?
C1 C7 1.432(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.197(2) . ?
C8 C9 1.4818(19) . ?
C9 C10 1.5478(18) . ?
C9 C22 1.5500(19) . ?
C9 C16 1.5540(18) . ?
C10 C11 1.3948(19) . ?
C10 C15 1.3982(19) . ?
C11 C12 1.394(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3961(19) . ?
C16 C21 1.398(2) . ?
C17 C18 1.3940(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.3948(19) . ?
C22 C23 1.3977(19) . ?
C23 C24 1.389(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
