#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:52:01 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233356 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/87/4348797.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_4348797
loop_
_publ_author_name
'Domyati, Doaa'
'Hope, Sydney L.'
'Latifi, Reza'
'Hearns, Micah D.'
'Tahsini, Laleh'
_publ_section_title
;
 Cu(I) Complexes of Pincer Pyridine-Based N-Heterocyclic Carbenes with
 Small Wingtip Substituents: Synthesis and Structural and Spectroscopic
 Studies.
;
_journal_issue                   22
_journal_name_full               'Inorganic chemistry'
_journal_page_first              11685
_journal_page_last               11693
_journal_paper_doi               10.1021/acs.inorgchem.6b01646
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C15 H17 Cu N5, F6 P'
_chemical_formula_sum            'C15 H17 Cu F6 N5 P'
_chemical_formula_weight         475.85
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.991(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0391(13)
_cell_length_b                   10.3084(12)
_cell_length_c                   16.3127(19)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.99
_cell_measurement_theta_min      2.37
_cell_volume                     1765.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29700
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0756 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.8092.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'metallic dark brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 'Diethyl-ether diffusion'
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0411P)²+1.9982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                4150
_reflns_number_total             4951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic6b01646_si_006.cif
_cod_data_source_block           full_integ
_cod_database_code               4348797
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_refinement_flags_posn
Cu1 Cu 0.90871(2) 0.04244(2) 0.933091(15) 0.01738(7) Uani 1 d .
N1 N 0.72119(15) 0.02791(16) 0.97090(10) 0.0183(3) Uani 1 d .
N2 N 0.75308(15) 0.27491(16) 0.87129(10) 0.0194(3) Uani 1 d .
N3 N 0.88539(15) 0.25351(15) 0.80044(10) 0.0179(3) Uani 1 d .
N4 N 0.86686(15) -0.22797(16) 0.97068(11) 0.0206(3) Uani 1 d .
N6 N 0.99581(15) -0.22298(16) 0.89606(11) 0.0201(3) Uani 1 d .
C1 C 0.63390(18) 0.1150(2) 0.92826(12) 0.0206(4) Uani 1 d .
C2 C 0.68111(19) 0.2528(2) 0.93235(13) 0.0224(4) Uani 1 d .
H2A H 0.6076 0.3129 0.9189 0.027 Uiso 1 calc R
H2B H 0.7364 0.2719 0.9916 0.027 Uiso 1 calc R
C3 C 0.84958(17) 0.19700(18) 0.86457(12) 0.0176(3) Uani 1 d .
C4 C 0.98214(19) 0.2026(2) 0.76538(13) 0.0228(4) Uani 1 d .
H4A H 1.0091 0.1166 0.7899 0.034 Uiso 1 calc GR
H4B H 1.0556 0.2612 0.7801 0.034 Uiso 1 calc GR
H4C H 0.9468 0.1957 0.7026 0.034 Uiso 1 calc GR
C5 C 0.93618(17) -0.14388(18) 0.93873(11) 0.0161(3) Uani 1 d .
C6 C 0.73072(19) 0.3769(2) 0.81340(13) 0.0234(4) Uani 1 d .
H6 H 0.6689 0.4435 0.8066 0.028 Uiso 1 calc R
C7 C 0.50854(19) 0.0803(2) 0.88456(13) 0.0254(4) Uani 1 d .
H7 H 0.4492 0.1434 0.8536 0.030 Uiso 1 calc R
C8 C 0.47205(19) -0.0479(2) 0.88708(13) 0.0264(4) Uani 1 d .
H8 H 0.3874 -0.0742 0.8574 0.032 Uiso 1 calc R
C9 C 0.56072(18) -0.1372(2) 0.93349(12) 0.0229(4) Uani 1 d .
H9 H 0.5372 -0.2251 0.9375 0.027 Uiso 1 calc R
C10 C 0.68443(18) -0.09594(19) 0.97391(12) 0.0189(3) Uani 1 d .
C11 C 0.78692(18) -0.18752(19) 1.02284(13) 0.0215(4) Uani 1 d .
H11A H 0.8405 -0.1445 1.0759 0.026 Uiso 1 calc R
H11B H 0.7475 -0.2649 1.0400 0.026 Uiso 1 calc R
C12 C 1.07644(19) -0.1768(2) 0.84604(13) 0.0220(4) Uani 1 d .
H12A H 1.0232 -0.1549 0.7876 0.033 Uiso 1 calc GR
H12B H 1.1369 -0.2450 0.8433 0.033 Uiso 1 calc GR
H12C H 1.1233 -0.0996 0.8737 0.033 Uiso 1 calc GR
C13 C 0.9632(2) -0.3507(2) 0.90110(19) 0.0375(6) Uani 1 d .
H13 H 0.9921 -0.4227 0.8759 0.045 Uiso 1 calc R
C14 C 0.8825(2) -0.3545(2) 0.94849(19) 0.0377(6) Uani 1 d .
H14 H 0.8441 -0.4295 0.9636 0.045 Uiso 1 calc R
C15 C 0.81402(19) 0.3631(2) 0.76856(13) 0.0232(4) Uani 1 d .
H15 H 0.8222 0.4180 0.7238 0.028 Uiso 1 calc R
P1 P 1.82295(5) 0.00444(5) 1.34936(3) 0.01973(11) Uani 1 d .
F1 F 1.85089(17) 0.04032(17) 1.44821(10) 0.0470(4) Uani 1 d .
F2 F 1.83666(13) -0.14602(13) 1.37380(10) 0.0370(3) Uani 1 d .
F3 F 1.80768(15) 0.15439(13) 1.32362(10) 0.0388(3) Uani 1 d .
F4 F 1.79359(13) -0.03289(14) 1.24986(9) 0.0355(3) Uani 1 d .
F5 F 1.97167(12) 0.01039(14) 1.35922(10) 0.0324(3) Uani 1 d .
F6 F 1.67351(13) -0.00090(15) 1.33808(12) 0.0418(4) Uani 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 0.0033 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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
N1 Cu1 Cu1 105.92(4) . 3_757
N1 Cu1 C5 103.92(6) . 3_757
C3 Cu1 Cu1 142.10(6) . 3_757
C3 Cu1 N1 92.11(7) . .
C3 Cu1 C5 99.26(7) . 3_757
C3 Cu1 C5 149.24(8) . .
C5 Cu1 Cu1 64.02(5) . 3_757
C5 Cu1 Cu1 44.59(4) 3_757 3_757
C5 Cu1 N1 93.56(7) . .
C5 Cu1 C5 108.61(6) . 3_757
C1 N1 Cu1 111.85(12) . .
C1 N1 C10 118.49(17) . .
C10 N1 Cu1 111.82(12) . .
C3 N2 C2 124.15(16) . .
C3 N2 C6 111.80(16) . .
C6 N2 C2 124.05(16) . .
C3 N3 C4 124.81(16) . .
C3 N3 C15 111.84(16) . .
C15 N3 C4 123.26(16) . .
C5 N4 C11 123.52(16) . .
C5 N4 C14 111.76(17) . .
C14 N4 C11 124.72(18) . .
C5 N6 C12 124.26(16) . .
C5 N6 C13 111.43(17) . .
C13 N6 C12 124.16(18) . .
N1 C1 C2 115.09(17) . .
N1 C1 C7 122.3(2) . .
C7 C1 C2 122.63(18) . .
N2 C2 C1 111.54(16) . .
N2 C2 H2A 109.3 . .
N2 C2 H2B 109.3 . .
C1 C2 H2A 109.3 . .
C1 C2 H2B 109.3 . .
H2A C2 H2B 108.0 . .
N2 C3 Cu1 124.68(14) . .
N3 C3 Cu1 132.04(14) . .
N3 C3 N2 103.27(15) . .
N3 C4 H4A 109.5 . .
N3 C4 H4B 109.5 . .
N3 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
Cu1 C5 Cu1 71.39(6) . 3_757
N4 C5 Cu1 105.55(11) . 3_757
N4 C5 Cu1 123.34(13) . .
N4 C5 N6 103.37(16) . .
N6 C5 Cu1 111.37(12) . 3_757
N6 C5 Cu1 131.23(13) . .
N2 C6 H6 126.8 . .
C15 C6 N2 106.41(17) . .
C15 C6 H6 126.8 . .
C1 C7 H7 120.6 . .
C8 C7 C1 118.75(19) . .
C8 C7 H7 120.6 . .
C7 C8 H8 120.4 . .
C9 C8 C7 119.15(19) . .
C9 C8 H8 120.4 . .
C8 C9 H9 120.6 . .
C8 C9 C10 118.8(2) . .
C10 C9 H9 120.6 . .
N1 C10 C9 122.51(18) . .
N1 C10 C11 115.48(16) . .
C9 C10 C11 121.99(19) . .
N4 C11 C10 111.18(15) . .
N4 C11 H11A 109.4 . .
N4 C11 H11B 109.4 . .
C10 C11 H11A 109.4 . .
C10 C11 H11B 109.4 . .
H11A C11 H11B 108.0 . .
N6 C12 H12A 109.5 . .
N6 C12 H12B 109.5 . .
N6 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N6 C13 H13 126.5 . .
C14 C13 N6 107.08(19) . .
C14 C13 H13 126.5 . .
N4 C14 H14 126.8 . .
C13 C14 N4 106.36(19) . .
C13 C14 H14 126.8 . .
N3 C15 H15 126.7 . .
C6 C15 N3 106.68(17) . .
C6 C15 H15 126.7 . .
F1 P1 F2 89.95(9) . .
F1 P1 F3 90.76(9) . .
F1 P1 F4 179.34(10) . .
F1 P1 F5 91.01(9) . .
F1 P1 F6 89.70(10) . .
F2 P1 F3 179.16(10) . .
F2 P1 F4 89.63(9) . .
F2 P1 F5 89.83(8) . .
F2 P1 F6 90.58(8) . .
F3 P1 F4 89.66(8) . .
F3 P1 F5 90.63(8) . .
F3 P1 F6 88.96(8) . .
F4 P1 F6 89.80(9) . .
F5 P1 F4 89.50(8) . .
F5 P1 F6 179.18(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cu1 2.6221(5) 3_757
Cu1 N1 2.3402(16) .
Cu1 C3 1.9399(19) .
Cu1 C5 1.9422(19) .
Cu1 C5 2.4871(18) 3_757
N1 C1 1.343(2) .
N1 C10 1.345(3) .
N2 C2 1.471(2) .
N2 C3 1.365(2) .
N2 C6 1.383(2) .
N3 C3 1.359(2) .
N3 C4 1.456(2) .
N3 C15 1.384(2) .
N4 C5 1.362(2) .
N4 C11 1.463(2) .
N4 C14 1.379(3) .
N6 C5 1.366(2) .
N6 C12 1.461(2) .
N6 C13 1.374(3) .
C1 C2 1.508(3) .
C1 C7 1.393(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 Cu1 2.4871(18) 3_757
C6 H6 0.9500 .
C6 C15 1.348(3) .
C7 H7 0.9500 .
C7 C8 1.386(3) .
C8 H8 0.9500 .
C8 C9 1.386(3) .
C9 H9 0.9500 .
C9 C10 1.387(3) .
C10 C11 1.500(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13 0.9500 .
C13 C14 1.349(4) .
C14 H14 0.9500 .
C15 H15 0.9500 .
P1 F1 1.5890(15) .
P1 F2 1.5968(14) .
P1 F3 1.5971(14) .
P1 F4 1.6009(15) .
P1 F5 1.6006(13) .
P1 F6 1.6034(14) .
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_4
Cu1 Cu1 N1 C1 153.12(13) 3_757 .
Cu1 Cu1 N1 C10 -71.31(13) 3_757 .
Cu1 Cu1 C3 N2 -101.27(16) 3_757 .
Cu1 Cu1 C3 N3 80.4(2) 3_757 .
Cu1 Cu1 C5 N4 96.73(15) 3_757 .
Cu1 Cu1 C5 N6 -102.49(18) 3_757 .
Cu1 N1 C1 C2 -51.07(18) . .
Cu1 N1 C1 C7 129.81(16) . .
Cu1 N1 C10 C9 -131.19(16) . .
Cu1 N1 C10 C11 47.83(18) . .
N1 Cu1 C3 N2 18.34(17) . .
N1 Cu1 C3 N3 -159.97(18) . .
N1 Cu1 C5 Cu1 -105.98(5) . 3_757
N1 Cu1 C5 N4 -9.25(16) . .
N1 Cu1 C5 N6 151.53(17) . .
N1 C1 C2 N2 79.5(2) . .
N1 C1 C7 C8 1.7(3) . .
N1 C10 C11 N4 -79.8(2) . .
N2 C6 C15 N3 -0.2(2) . .
N6 C13 C14 N4 0.5(3) . .
C1 N1 C10 C9 1.1(3) . .
C1 N1 C10 C11 -179.84(16) . .
C1 C7 C8 C9 0.6(3) . .
C2 N2 C3 Cu1 0.6(3) . .
C2 N2 C3 N3 179.32(17) . .
C2 N2 C6 C15 -179.30(18) . .
C2 C1 C7 C8 -177.39(18) . .
C3 Cu1 N1 C1 6.85(14) . .
C3 Cu1 N1 C10 142.43(13) . .
C3 Cu1 C5 Cu1 153.84(13) . 3_757
C3 Cu1 C5 N4 -109.43(18) . .
C3 Cu1 C5 N6 51.4(3) . .
C3 N2 C2 C1 -49.8(2) . .
C3 N2 C6 C15 0.4(2) . .
C3 N3 C15 C6 0.0(2) . .
C4 N3 C3 Cu1 1.9(3) . .
C4 N3 C3 N2 -176.63(17) . .
C4 N3 C15 C6 176.94(18) . .
C5 Cu1 N1 C1 106.93(14) 3_757 .
C5 Cu1 N1 C1 -142.90(14) . .
C5 Cu1 N1 C10 -117.50(13) 3_757 .
C5 Cu1 N1 C10 -7.33(13) . .
C5 Cu1 C3 N2 118.91(18) . .
C5 Cu1 C3 N2 -86.14(16) 3_757 .
C5 Cu1 C3 N3 95.56(18) 3_757 .
C5 Cu1 C3 N3 -59.4(3) . .
C5 Cu1 C5 Cu1 0.0 3_757 3_757
C5 Cu1 C5 N4 96.73(15) 3_757 .
C5 Cu1 C5 N6 -102.49(18) 3_757 .
C5 N4 C11 C10 60.5(2) . .
C5 N4 C14 C13 -0.2(3) . .
C5 N6 C13 C14 -0.7(3) . .
C6 N2 C2 C1 129.86(19) . .
C6 N2 C3 Cu1 -179.11(14) . .
C6 N2 C3 N3 -0.4(2) . .
C7 C1 C2 N2 -101.3(2) . .
C7 C8 C9 C10 -1.9(3) . .
C8 C9 C10 N1 1.0(3) . .
C8 C9 C10 C11 -177.91(17) . .
C9 C10 C11 N4 99.2(2) . .
C10 N1 C1 C2 176.60(16) . .
C10 N1 C1 C7 -2.5(3) . .
C11 N4 C5 Cu1 -15.5(3) . .
C11 N4 C5 Cu1 62.20(19) . 3_757
C11 N4 C5 N6 179.27(17) . .
C11 N4 C14 C13 -179.7(2) . .
C12 N6 C5 Cu1 12.7(3) . .
C12 N6 C5 Cu1 -70.85(19) . 3_757
C12 N6 C5 N4 176.27(17) . .
C12 N6 C13 C14 -176.4(2) . .
C13 N6 C5 Cu1 113.40(18) . 3_757
C13 N6 C5 Cu1 -163.06(18) . .
C13 N6 C5 N4 0.5(2) . .
C14 N4 C5 Cu1 165.08(17) . .
C14 N4 C5 Cu1 -117.23(18) . 3_757
C14 N4 C5 N6 -0.2(2) . .
C14 N4 C11 C10 -120.2(2) . .
C15 N3 C3 Cu1 178.81(15) . .
C15 N3 C3 N2 0.2(2) . .
