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#$Date: 2021-11-25 01:21:22 +0200 (Thu, 25 Nov 2021) $
#$Revision: 270867 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/54/1565402.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_1565402
loop_
_publ_author_name
'Jayasooriya, Isuri U.'
'Bakhoda, Abolghasem (Gus)'
'Palmer, Rachel'
'Ng, Kristi'
'Khachemoune, Nour L.'
'Bertke, Jeffery A.'
'Warren, Timothy H.'
_publ_section_title
;
 Copper(ii) ketimides in sp3 C--H amination
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01990B
_journal_year                    2021
_chemical_formula_moiety         'C30 H24 Cl4 Cu N3'
_chemical_formula_sum            'C30 H24 Cl4 Cu N3'
_chemical_formula_weight         631.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc239b1t
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.036(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8807(5)
_cell_length_b                   15.5610(5)
_cell_length_c                   14.8263(6)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.25
_cell_volume                     2825.71(19)
_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-2018-1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26800
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.487
_diffrn_reflns_theta_min         1.834
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0222
_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)+(0.0248P)²+1.6714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4723
_reflns_number_total             5209
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc01990b2.cif
_cod_data_source_block           P21n_a_CCDC1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1565402
_shelx_shelxl_version_number     2017/1
_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   0.712
_shelx_estimated_absorpt_t_max   0.874
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cu1 Cu 0.28582(2) 0.74121(2) 0.53319(2) 0.01256(6) Uani 1 1 d . . . . .
Cl1 Cl 0.46318(3) 0.88426(3) 0.49832(3) 0.02622(11) Uani 1 1 d . . . . .
Cl2 Cl 0.06871(3) 0.80960(3) 0.24775(3) 0.02331(10) Uani 1 1 d . . . . .
Cl3 Cl 0.36636(3) 0.80349(3) 0.79083(3) 0.02336(10) Uani 1 1 d . . . . .
Cl4 Cl 0.05165(3) 0.59771(3) 0.57186(3) 0.02145(10) Uani 1 1 d . . . . .
N1 N 0.22754(11) 0.83894(8) 0.44555(9) 0.0127(3) Uani 1 1 d . . . . .
N2 N 0.19474(11) 0.75430(8) 0.61192(9) 0.0130(3) Uani 1 1 d . . . . .
N3 N 0.40245(12) 0.68141(8) 0.50895(10) 0.0144(3) Uani 1 1 d . . . . .
H3 H 0.4673(17) 0.6905(12) 0.5449(14) 0.022 Uiso 1 1 d . U . . .
C1 C 0.15253(13) 0.89126(10) 0.45849(11) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.10348(13) 0.87998(10) 0.53046(11) 0.0138(3) Uani 1 1 d . . . . .
H2 H 0.049423 0.921350 0.530949 0.017 Uiso 1 1 calc R U . . .
C3 C 0.12208(13) 0.81733(9) 0.60123(11) 0.0124(3) Uani 1 1 d . . . . .
C4 C 0.11660(14) 0.97066(10) 0.39769(12) 0.0194(4) Uani 1 1 d . . . . .
H4A H 0.158224 0.975179 0.352636 0.029 Uiso 1 1 calc R U . . .
H4B H 0.129783 1.021760 0.438305 0.029 Uiso 1 1 calc R U . . .
H4C H 0.038563 0.966403 0.362810 0.029 Uiso 1 1 calc R U . . .
C5 C 0.05642(14) 0.82354(10) 0.66947(12) 0.0175(3) Uani 1 1 d . . . . .
H5A H 0.014062 0.770685 0.666295 0.026 Uiso 1 1 calc R U . . .
H5B H 0.006659 0.872725 0.652321 0.026 Uiso 1 1 calc R U . . .
H5C H 0.105904 0.831232 0.734087 0.026 Uiso 1 1 calc R U . . .
C6 C 0.26867(13) 0.84799(9) 0.36897(11) 0.0133(3) Uani 1 1 d . . . . .
C7 C 0.38012(14) 0.86309(10) 0.38385(12) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.42658(15) 0.86367(11) 0.31147(14) 0.0251(4) Uani 1 1 d . . . . .
H8 H 0.502850 0.872600 0.325067 0.030 Uiso 1 1 calc R U . . .
C9 C 0.36140(17) 0.85121(12) 0.21948(14) 0.0299(4) Uani 1 1 d . . . . .
H9 H 0.392298 0.852694 0.169038 0.036 Uiso 1 1 calc R U . . .
C10 C 0.25135(16) 0.83659(12) 0.20069(13) 0.0262(4) Uani 1 1 d . . . . .
H10 H 0.206166 0.828318 0.137186 0.031 Uiso 1 1 calc R U . . .
C11 C 0.20640(14) 0.83393(10) 0.27430(11) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.21105(13) 0.69579(10) 0.68746(11) 0.0132(3) Uani 1 1 d . . . . .
C13 C 0.29240(13) 0.70850(10) 0.77412(11) 0.0167(3) Uani 1 1 d . . . . .
C14 C 0.31710(15) 0.64787(11) 0.84604(12) 0.0232(4) Uani 1 1 d . . . . .
H14 H 0.373718 0.658321 0.903668 0.028 Uiso 1 1 calc R U . . .
C15 C 0.25835(16) 0.57177(11) 0.83305(13) 0.0252(4) Uani 1 1 d . . . . .
H15 H 0.274852 0.529677 0.881851 0.030 Uiso 1 1 calc R U . . .
C16 C 0.17588(15) 0.55708(11) 0.74928(13) 0.0212(4) Uani 1 1 d . . . . .
H16 H 0.134883 0.505295 0.740491 0.025 Uiso 1 1 calc R U . . .
C17 C 0.15342(13) 0.61834(10) 0.67825(11) 0.0155(3) Uani 1 1 d . . . . .
C18 C 0.40523(13) 0.63854(10) 0.43504(11) 0.0137(3) Uani 1 1 d . . . . .
C19 C 0.30041(13) 0.61381(9) 0.36468(11) 0.0144(3) Uani 1 1 d . . . . .
C20 C 0.28857(14) 0.61174(11) 0.26795(12) 0.0193(4) Uani 1 1 d . . . . .
H20 H 0.349474 0.623375 0.246579 0.023 Uiso 1 1 calc R U . . .
C21 C 0.18820(15) 0.59275(11) 0.20313(12) 0.0240(4) Uani 1 1 d . . . . .
H21 H 0.180231 0.592146 0.137256 0.029 Uiso 1 1 calc R U . . .
C22 C 0.09940(15) 0.57464(11) 0.23357(13) 0.0240(4) Uani 1 1 d . . . . .
H22 H 0.030612 0.561778 0.188711 0.029 Uiso 1 1 calc R U . . .
C23 C 0.11089(14) 0.57528(11) 0.32952(13) 0.0215(4) Uani 1 1 d . . . . .
H23 H 0.050126 0.562120 0.350538 0.026 Uiso 1 1 calc R U . . .
C24 C 0.21037(14) 0.59499(10) 0.39474(12) 0.0174(3) Uani 1 1 d . . . . .
H24 H 0.217646 0.595756 0.460484 0.021 Uiso 1 1 calc R U . . .
C25 C 0.51014(13) 0.61389(10) 0.42054(11) 0.0144(3) Uani 1 1 d . . . . .
C26 C 0.59826(13) 0.67063(11) 0.44590(11) 0.0164(3) Uani 1 1 d . . . . .
H26 H 0.589321 0.726377 0.468547 0.020 Uiso 1 1 calc R U . . .
C27 C 0.69872(14) 0.64637(11) 0.43833(12) 0.0205(4) Uani 1 1 d . . . . .
H27 H 0.758412 0.685330 0.455904 0.025 Uiso 1 1 calc R U . . .
C28 C 0.71205(14) 0.56498(11) 0.40500(12) 0.0215(4) Uani 1 1 d . . . . .
H28 H 0.781327 0.547771 0.401191 0.026 Uiso 1 1 calc R U . . .
C29 C 0.62450(14) 0.50903(11) 0.37738(12) 0.0203(4) Uani 1 1 d . . . . .
H29 H 0.633418 0.453887 0.353295 0.024 Uiso 1 1 calc R U . . .
C30 C 0.52373(14) 0.53304(10) 0.38467(11) 0.0176(3) Uani 1 1 d . . . . .
H30 H 0.463775 0.494438 0.365230 0.021 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
N3 Cu1 N2 147.58(6) . . ?
N3 Cu1 N1 114.37(6) . . ?
N2 Cu1 N1 97.98(5) . . ?
C1 N1 C6 122.17(13) . . ?
C1 N1 Cu1 121.39(11) . . ?
C6 N1 Cu1 116.43(10) . . ?
C3 N2 C12 119.85(13) . . ?
C3 N2 Cu1 123.35(11) . . ?
C12 N2 Cu1 116.73(10) . . ?
C18 N3 Cu1 130.25(12) . . ?
C18 N3 H3 109.7(13) . . ?
Cu1 N3 H3 118.8(13) . . ?
N1 C1 C2 123.52(14) . . ?
N1 C1 C4 121.22(14) . . ?
C2 C1 C4 115.23(14) . . ?
C3 C2 C1 129.98(15) . . ?
C3 C2 H2 115.0 . . ?
C1 C2 H2 115.0 . . ?
N2 C3 C2 123.66(14) . . ?
N2 C3 C5 119.12(14) . . ?
C2 C3 C5 117.21(14) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C11 123.59(14) . . ?
N1 C6 C7 120.98(14) . . ?
C11 C6 C7 115.09(15) . . ?
C8 C7 C6 123.18(16) . . ?
C8 C7 Cl1 118.34(14) . . ?
C6 C7 Cl1 118.47(13) . . ?
C9 C8 C7 119.41(17) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 119.86(17) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.07(17) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 122.35(16) . . ?
C10 C11 Cl2 118.35(14) . . ?
C6 C11 Cl2 119.28(13) . . ?
C13 C12 C17 115.81(14) . . ?
C13 C12 N2 121.63(14) . . ?
C17 C12 N2 122.36(14) . . ?
C14 C13 C12 122.64(16) . . ?
C14 C13 Cl3 119.04(13) . . ?
C12 C13 Cl3 118.31(12) . . ?
C13 C14 C15 119.31(16) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.08(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.48(16) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C12 122.66(15) . . ?
C16 C17 Cl4 118.96(13) . . ?
C12 C17 Cl4 118.37(12) . . ?
N3 C18 C19 118.26(14) . . ?
N3 C18 C25 121.46(15) . . ?
C19 C18 C25 120.28(14) . . ?
C20 C19 C24 119.09(15) . . ?
C20 C19 C18 121.11(15) . . ?
C24 C19 C18 119.77(14) . . ?
C21 C20 C19 120.03(16) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.44(17) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.88(16) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.16(16) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 120.39(16) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C26 C25 C30 119.01(15) . . ?
C26 C25 C18 119.95(14) . . ?
C30 C25 C18 121.00(15) . . ?
C27 C26 C25 120.55(15) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 119.90(16) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 120.01(16) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.30(16) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.18(16) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
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
Cu1 N3 1.8937(14) . ?
Cu1 N2 1.9049(13) . ?
Cu1 N1 1.9901(13) . ?
Cl1 C7 1.7346(17) . ?
Cl2 C11 1.7353(17) . ?
Cl3 C13 1.7344(17) . ?
Cl4 C17 1.7405(17) . ?
N1 C1 1.322(2) . ?
N1 C6 1.401(2) . ?
N2 C3 1.331(2) . ?
N2 C12 1.408(2) . ?
N3 C18 1.293(2) . ?
N3 H3 0.85(2) . ?
C1 C2 1.409(2) . ?
C1 C4 1.515(2) . ?
C2 C3 1.397(2) . ?
C2 H2 0.9500 . ?
C3 C5 1.509(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.401(2) . ?
C6 C7 1.403(2) . ?
C7 C8 1.381(2) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.398(2) . ?
C12 C17 1.400(2) . ?
C13 C14 1.385(2) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(2) . ?
C16 H16 0.9500 . ?
C18 C19 1.479(2) . ?
C18 C25 1.483(2) . ?
C19 C20 1.395(2) . ?
C19 C24 1.396(2) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.395(2) . ?
C25 C30 1.398(2) . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 Cl2 0.85(2) 2.88(2) 3.5279(14) 133.8(16) 4_676 yes
