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#$Date: 2024-03-04 22:20:17 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290192 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/50/7715042.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_7715042
loop_
_publ_author_name
'Sharma, Mitu'
'Perkins, Amanda M.'
'Awoyemi, Raymond Femi'
'Schmittou, Allison N.'
'Raju, Selvam'
'Pierce, Brad S.'
'Donnadieu, Bruno'
'Wipf, David O.'
'Stokes, Sean L.'
'Emerson, Joseph P.'
_publ_section_title
;
 Three water-soluble copper(II) N-heterocyclic carbene complexes:
 toward copper-catalyzed ketone reduction under sustainable conditions.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3180
_journal_page_last               3190
_journal_paper_doi               10.1039/d3dt03406b
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C17 H17 Cu F6 N4 O2 P'
_chemical_formula_sum            'C17 H17 Cu F6 N4 O2 P'
_chemical_formula_weight         517.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-15 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.6770(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0314(3)
_cell_length_b                   17.4564(4)
_cell_length_c                   9.0216(2)
_cell_measurement_reflns_used    1866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.489
_cell_measurement_theta_min      3.490
_cell_volume                     1994.05(8)
_computing_cell_refinement       'APEX4 v2021 4.0'
_computing_data_collection       'APEX4 v2021.4.0'
_computing_data_reduction        'Saint, APEX v2021.4.0.'
_computing_molecular_graphics    'Mercury V.4.2.0,POV-Ray v 3.7'
_computing_publication_material  'APEX3 v202.4.0'
_computing_structure_refinement  SHELXTL-2018/3
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS D8 Venture  '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23796
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_min         3.490
_exptl_absorpt_coefficient_mu    3.045
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+8.2561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3172
_reflns_number_total             4057
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt03406b2.cif
_cod_data_source_block           C_JE_002
_cod_depositor_comments
'Adding full bibliography for 7715042--7715043.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7715042
_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   0.793
_shelx_estimated_absorpt_t_max   0.936
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.18235(4) 0.28742(3) 0.67082(6) 0.01493(14) Uani 1 1 d . . . . .
N1 N 0.0410(2) 0.33250(18) 0.5469(3) 0.0175(7) Uani 1 1 d . . . . .
N2 N 0.2175(3) 0.43563(18) 0.5398(3) 0.0167(7) Uani 1 1 d . . . . .
N3 N 0.3315(3) 0.24787(19) 0.7925(4) 0.0186(7) Uani 1 1 d . . . . .
N4 N 0.3335(2) 0.41344(18) 0.7458(4) 0.0179(7) Uani 1 1 d . . . . .
C1 C -0.0476(3) 0.2961(2) 0.5619(5) 0.0203(8) Uani 1 1 d . . . . .
H1 H -0.042762 0.260966 0.643704 0.024 Uiso 1 1 calc R U . . .
C2 C -0.1444(3) 0.3079(2) 0.4635(5) 0.0254(9) Uani 1 1 d . . . . .
H2 H -0.204976 0.280732 0.476133 0.030 Uiso 1 1 calc R U . . .
C3 C -0.1519(3) 0.3599(3) 0.3461(5) 0.0272(9) Uani 1 1 d . . . . .
H3 H -0.217291 0.367998 0.274509 0.033 Uiso 1 1 calc R U . . .
C4 C -0.0631(3) 0.3998(2) 0.3345(5) 0.0232(9) Uani 1 1 d . . . . .
H4 H -0.067567 0.437415 0.257198 0.028 Uiso 1 1 calc R U . . .
C5 C 0.0331(3) 0.3851(2) 0.4357(4) 0.0170(8) Uani 1 1 d . . . . .
C6 C 0.1298(3) 0.4247(2) 0.4073(4) 0.0191(8) Uani 1 1 d . . . . .
H6A H 0.155746 0.394679 0.330531 0.023 Uiso 1 1 calc R U . . .
H6B H 0.108190 0.475606 0.362140 0.023 Uiso 1 1 calc R U . . .
C7 C 0.2882(3) 0.4959(2) 0.5590(5) 0.0204(8) Uani 1 1 d . . . . .
H7 H 0.286090 0.538524 0.492760 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3611(3) 0.4824(2) 0.6903(5) 0.0227(9) Uani 1 1 d . . . . .
H8 H 0.419617 0.513933 0.735350 0.027 Uiso 1 1 calc R U . . .
C9 C 0.2460(3) 0.3853(2) 0.6543(4) 0.0178(8) Uani 1 1 d . . . . .
C10 C 0.3836(3) 0.3784(2) 0.8918(4) 0.0234(9) Uani 1 1 d . . . . .
H10A H 0.338636 0.387889 0.964375 0.028 Uiso 1 1 calc R U . . .
H10B H 0.452215 0.404039 0.932676 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4024(3) 0.2930(2) 0.8846(4) 0.0201(8) Uani 1 1 d . . . . .
C12 C 0.4915(3) 0.2629(3) 0.9836(5) 0.0291(10) Uani 1 1 d . . . . .
H12 H 0.540185 0.295894 1.048640 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5087(4) 0.1849(3) 0.9870(6) 0.0357(11) Uani 1 1 d . . . . .
H13 H 0.568785 0.163516 1.055115 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4378(3) 0.1387(3) 0.8905(5) 0.0300(10) Uani 1 1 d . . . . .
H14 H 0.448379 0.084893 0.890072 0.036 Uiso 1 1 calc R U . . .
C15 C 0.3504(3) 0.1717(2) 0.7937(5) 0.0214(8) Uani 1 1 d . . . . .
H15 H 0.302068 0.139683 0.725722 0.026 Uiso 1 1 calc R U . . .
O1 O 0.1252(2) 0.18312(14) 0.6229(3) 0.0166(5) Uani 1 1 d . . . . .
O2 O 0.1438(2) 0.21544(16) 0.3936(3) 0.0200(6) Uani 1 1 d . . . . .
C16 C 0.1124(3) 0.1693(2) 0.4800(4) 0.0161(8) Uani 1 1 d . . . . .
C17 C 0.0559(3) 0.0973(2) 0.4195(5) 0.0225(8) Uani 1 1 d . . . . .
H17A H -0.020429 0.106752 0.392658 0.034 Uiso 1 1 calc R U . . .
H17B H 0.072274 0.057247 0.497551 0.034 Uiso 1 1 calc R U . . .
H17C H 0.078658 0.080776 0.328519 0.034 Uiso 1 1 calc R U . . .
P1 P 0.70589(8) 0.42517(6) 0.87247(12) 0.0235(2) Uani 1 1 d . . . . .
F1 F 0.6039(2) 0.44425(18) 0.7386(4) 0.0486(8) Uani 1 1 d . . . . .
F2 F 0.6397(3) 0.4436(2) 0.9958(4) 0.0592(10) Uani 1 1 d . . . . .
F3 F 0.8071(2) 0.4058(2) 1.0014(3) 0.0585(9) Uani 1 1 d . . . . .
F4 F 0.7705(2) 0.40664(19) 0.7471(3) 0.0474(8) Uani 1 1 d . . . . .
F5 F 0.7399(3) 0.51221(18) 0.8692(5) 0.0651(10) Uani 1 1 d . . . . .
F6 F 0.6688(3) 0.33882(17) 0.8676(4) 0.0556(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 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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C9 Cu1 O1 161.83(13) . . ?
C9 Cu1 N1 88.03(15) . . ?
O1 Cu1 N1 89.46(12) . . ?
C9 Cu1 N3 88.26(15) . . ?
O1 Cu1 N3 93.77(12) . . ?
N1 Cu1 N3 176.17(13) . . ?
C9 Cu1 O2 106.82(13) . 4_566 ?
O1 Cu1 O2 91.34(10) . 4_566 ?
N1 Cu1 O2 97.85(11) . 4_566 ?
N3 Cu1 O2 84.14(11) . 4_566 ?
C5 N1 C1 118.6(3) . . ?
C5 N1 Cu1 124.3(3) . . ?
C1 N1 Cu1 116.0(3) . . ?
C9 N2 C7 110.3(3) . . ?
C9 N2 C6 124.6(3) . . ?
C7 N2 C6 124.9(3) . . ?
C11 N3 C15 118.3(4) . . ?
C11 N3 Cu1 123.0(3) . . ?
C15 N3 Cu1 118.0(3) . . ?
C9 N4 C8 110.8(3) . . ?
C9 N4 C10 122.6(3) . . ?
C8 N4 C10 126.3(3) . . ?
N1 C1 C2 122.6(4) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.7(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.9(4) . . ?
N1 C5 C6 121.2(3) . . ?
C4 C5 C6 117.6(3) . . ?
N2 C6 C5 116.4(3) . . ?
N2 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
N2 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
C8 C7 N2 106.6(3) . . ?
C8 C7 H7 126.7 . . ?
N2 C7 H7 126.7 . . ?
C7 C8 N4 106.2(3) . . ?
C7 C8 H8 126.9 . . ?
N4 C8 H8 126.9 . . ?
N4 C9 N2 106.0(3) . . ?
N4 C9 Cu1 127.0(3) . . ?
N2 C9 Cu1 126.7(3) . . ?
N4 C10 C11 114.6(3) . . ?
N4 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
N4 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N3 C11 C12 121.7(4) . . ?
N3 C11 C10 120.6(3) . . ?
C12 C11 C10 117.6(4) . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 119.0(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 122.3(4) . . ?
N3 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C16 O1 Cu1 110.2(2) . . ?
C16 O2 Cu1 137.5(2) . 4_565 ?
O2 C16 O1 121.3(3) . . ?
O2 C16 C17 121.2(3) . . ?
O1 C16 C17 117.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F3 P1 F6 90.7(2) . . ?
F3 P1 F5 91.8(2) . . ?
F6 P1 F5 177.3(2) . . ?
F3 P1 F2 91.40(19) . . ?
F6 P1 F2 89.98(19) . . ?
F5 P1 F2 91.1(2) . . ?
F3 P1 F4 89.43(17) . . ?
F6 P1 F4 89.76(18) . . ?
F5 P1 F4 89.10(19) . . ?
F2 P1 F4 179.13(18) . . ?
F3 P1 F1 178.86(19) . . ?
F6 P1 F1 89.08(18) . . ?
F5 P1 F1 88.42(19) . . ?
F2 P1 F1 89.72(18) . . ?
F4 P1 F1 89.45(16) . . ?
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 C9 1.920(4) . ?
Cu1 O1 1.976(3) . ?
Cu1 N1 2.071(3) . ?
Cu1 N3 2.109(3) . ?
Cu1 O2 2.184(2) 4_566 ?
N1 C5 1.346(5) . ?
N1 C1 1.352(5) . ?
N2 C9 1.340(5) . ?
N2 C7 1.383(5) . ?
N2 C6 1.457(5) . ?
N3 C11 1.342(5) . ?
N3 C15 1.351(5) . ?
N4 C9 1.333(5) . ?
N4 C8 1.384(5) . ?
N4 C10 1.459(5) . ?
C1 C2 1.376(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.512(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.352(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.516(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.390(6) . ?
C12 C13 1.379(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O1 C16 1.283(4) . ?
O2 C16 1.254(4) . ?
C16 C17 1.493(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
P1 F3 1.576(3) . ?
P1 F6 1.580(3) . ?
P1 F5 1.585(3) . ?
P1 F2 1.594(3) . ?
P1 F4 1.594(3) . ?
P1 F1 1.605(3) . ?
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
C5 N1 C1 C2 3.3(6) . . . . ?
Cu1 N1 C1 C2 -165.2(3) . . . . ?
N1 C1 C2 C3 -1.1(6) . . . . ?
C1 C2 C3 C4 -2.0(6) . . . . ?
C2 C3 C4 C5 2.8(6) . . . . ?
C1 N1 C5 C4 -2.5(5) . . . . ?
Cu1 N1 C5 C4 165.0(3) . . . . ?
C1 N1 C5 C6 -176.6(3) . . . . ?
Cu1 N1 C5 C6 -9.1(5) . . . . ?
C3 C4 C5 N1 -0.6(6) . . . . ?
C3 C4 C5 C6 173.8(4) . . . . ?
C9 N2 C6 C5 36.7(5) . . . . ?
C7 N2 C6 C5 -149.2(3) . . . . ?
N1 C5 C6 N2 -30.6(5) . . . . ?
C4 C5 C6 N2 155.0(3) . . . . ?
C9 N2 C7 C8 -0.9(4) . . . . ?
C6 N2 C7 C8 -175.8(3) . . . . ?
N2 C7 C8 N4 1.0(4) . . . . ?
C9 N4 C8 C7 -0.8(4) . . . . ?
C10 N4 C8 C7 -174.4(3) . . . . ?
C8 N4 C9 N2 0.2(4) . . . . ?
C10 N4 C9 N2 174.1(3) . . . . ?
C8 N4 C9 Cu1 174.2(3) . . . . ?
C10 N4 C9 Cu1 -12.0(5) . . . . ?
C7 N2 C9 N4 0.4(4) . . . . ?
C6 N2 C9 N4 175.3(3) . . . . ?
C7 N2 C9 Cu1 -173.5(3) . . . . ?
C6 N2 C9 Cu1 1.3(5) . . . . ?
C9 N4 C10 C11 50.2(5) . . . . ?
C8 N4 C10 C11 -137.0(4) . . . . ?
C15 N3 C11 C12 -2.4(5) . . . . ?
Cu1 N3 C11 C12 168.4(3) . . . . ?
C15 N3 C11 C10 -178.0(3) . . . . ?
Cu1 N3 C11 C10 -7.3(5) . . . . ?
N4 C10 C11 N3 -37.5(5) . . . . ?
N4 C10 C11 C12 146.7(4) . . . . ?
N3 C11 C12 C13 0.7(6) . . . . ?
C10 C11 C12 C13 176.5(4) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C11 N3 C15 C14 2.6(6) . . . . ?
Cu1 N3 C15 C14 -168.6(3) . . . . ?
C13 C14 C15 N3 -1.1(6) . . . . ?
Cu1 O2 C16 O1 159.8(3) 4_565 . . . ?
Cu1 O2 C16 C17 -22.0(6) 4_565 . . . ?
Cu1 O1 C16 O2 6.5(4) . . . . ?
Cu1 O1 C16 C17 -171.7(3) . . . . ?
