#------------------------------------------------------------------------------
#$Date: 2020-09-22 04:25:22 +0300 (Tue, 22 Sep 2020) $
#$Revision: 256608 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/91/1559136.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_1559136
loop_
_publ_author_name
'Karimata, Ayumu'
'Patil, Pradnya H.'
'Fayzullin, Robert R.'
'Khaskin, Eugene'
'Lapointe, Sébastien'
'Khusnutdinova, Julia R.'
_publ_section_title
;
 Triboluminescence of a new family of CuI-NHC complexes in crystalline
 solid and in amorphous polymer films
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04442C
_journal_year                    2020
_chemical_formula_moiety         'C37 H44 Cu N6 1+, F6 P 1-, 0.5(C4 H10 O)'
_chemical_formula_sum            'C39 H49 Cu F6 N6 O0.5 P'
_chemical_formula_weight         818.35
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-06-13 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.3314(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.46796(15)
_cell_length_b                   19.4563(2)
_cell_length_c                   17.9268(3)
_cell_measurement_reflns_used    49732
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      32.4160
_cell_measurement_theta_min      2.2010
_cell_volume                     3838.51(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012);
PLATON (Spek, 2009); Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012); PLATON (Spek, 2009);
Olex2 (Dolomanov et al., 2009); enCIFer (Allen, 2004)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Rigaku XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            111295
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.347
_diffrn_reflns_theta_min         2.093
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.401
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015).
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model. Empirical absorption correction using
spherical harmonics, frame scaling and detector area scaling,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       prism
_exptl_crystal_F_000             1708
_exptl_crystal_recrystallization_method
'vapor diffusion in an acetonitrile-diethyl ether system at r.t.'
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.158
_refine_diff_density_max         1.018
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         12827
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0462P)²+1.3487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11273
_reflns_number_total             12827
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04442c7.cif
_cod_data_source_block           jk288
_cod_original_cell_volume        3838.52(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C39 H49 Cu F6 N6 O0.50 P'
_cod_database_code               1559136
_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   0.850
_shelx_estimated_absorpt_t_max   0.900
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 0.15847(2) 0.41243(2) 0.28805(2) 0.01594(4) Uani 1 1 d . . . . .
N1 N 0.28131(8) 0.43571(5) 0.39827(5) 0.01610(15) Uani 1 1 d . . . . .
N2 N 0.15365(8) 0.31877(5) 0.34849(5) 0.01678(16) Uani 1 1 d . . . . .
N3 N 0.32343(8) 0.36351(5) 0.27241(5) 0.01730(16) Uani 1 1 d . . . . .
N4 N 0.03579(9) 0.41499(5) 0.46488(6) 0.0239(2) Uani 1 1 d . . . . .
N5 N 0.06247(10) 0.53224(5) 0.19083(6) 0.02363(19) Uani 1 1 d . . . . .
N6 N -0.08048(9) 0.46034(6) 0.18738(6) 0.02343(19) Uani 1 1 d . . . . .
C1 C 0.04214(10) 0.46903(6) 0.21811(6) 0.01922(19) Uani 1 1 d . . . . .
C2 C -0.04430(14) 0.56180(8) 0.14479(8) 0.0350(3) Uani 1 1 d . . . . .
H2 H -0.052173 0.605290 0.119768 0.042 Uiso 1 1 calc R U . . .
C3 C -0.13356(13) 0.51689(8) 0.14277(8) 0.0349(3) Uani 1 1 d . . . . .
H3 H -0.217180 0.522462 0.116039 0.042 Uiso 1 1 calc R U . . .
C11 C 0.42459(10) 0.39703(7) 0.33087(7) 0.0230(2) Uani 1 1 d . . . . .
H11A H 0.445909 0.440324 0.308816 0.028 Uiso 1 1 calc R U . . .
H11B H 0.496644 0.366600 0.342187 0.028 Uiso 1 1 calc R U . . .
C12 C 0.39483(9) 0.41289(5) 0.40580(6) 0.01813(19) Uani 1 1 d . . . . .
C13 C 0.48100(10) 0.40590(6) 0.47734(7) 0.0241(2) Uani 1 1 d . . . . .
H13 H 0.559987 0.388870 0.480819 0.029 Uiso 1 1 calc R U . . .
C14 C 0.44887(12) 0.42441(7) 0.54357(7) 0.0278(2) Uani 1 1 d . . . . .
H14 H 0.506664 0.422017 0.593243 0.033 Uiso 1 1 calc R U . . .
C15 C 0.33108(11) 0.44651(7) 0.53635(7) 0.0257(2) Uani 1 1 d . . . . .
H15 H 0.307191 0.458880 0.581173 0.031 Uiso 1 1 calc R U . . .
C16 C 0.24823(10) 0.45039(5) 0.46287(6) 0.01877(19) Uani 1 1 d . . . . .
C17 C 0.11635(10) 0.46937(6) 0.45244(7) 0.0219(2) Uani 1 1 d . . . . .
H17A H 0.114204 0.507501 0.488597 0.026 Uiso 1 1 calc R U . . .
H17B H 0.082615 0.487182 0.398972 0.026 Uiso 1 1 calc R U . . .
C21 C 0.31302(10) 0.28973(6) 0.28934(7) 0.0204(2) Uani 1 1 d . . . . .
H21A H 0.395539 0.269655 0.307159 0.025 Uiso 1 1 calc R U . . .
H21B H 0.268941 0.265935 0.240783 0.025 Uiso 1 1 calc R U . . .
C22 C 0.24781(10) 0.27679(5) 0.35026(6) 0.01776(18) Uani 1 1 d . . . . .
C23 C 0.28089(11) 0.22299(6) 0.40279(7) 0.0234(2) Uani 1 1 d . . . . .
H23 H 0.350090 0.195558 0.404391 0.028 Uiso 1 1 calc R U . . .
C24 C 0.21063(13) 0.21012(6) 0.45295(7) 0.0265(2) Uani 1 1 d . . . . .
H24 H 0.228511 0.172159 0.487637 0.032 Uiso 1 1 calc R U . . .
C25 C 0.11419(12) 0.25331(6) 0.45176(7) 0.0247(2) Uani 1 1 d . . . . .
H25 H 0.064685 0.245137 0.485357 0.030 Uiso 1 1 calc R U . . .
C26 C 0.09055(10) 0.30896(6) 0.40069(6) 0.01935(19) Uani 1 1 d . . . . .
C27 C -0.00338(10) 0.36268(7) 0.40401(7) 0.0235(2) Uani 1 1 d . . . . .
H27A H -0.029128 0.386248 0.353058 0.028 Uiso 1 1 calc R U . . .
H27B H -0.075516 0.338919 0.411614 0.028 Uiso 1 1 calc R U . . .
C31 C 0.34685(11) 0.36885(7) 0.19545(7) 0.0256(2) Uani 1 1 d . . . . .
H31A H 0.278471 0.348914 0.155617 0.038 Uiso 1 1 calc R U . . .
H31B H 0.421493 0.343854 0.196509 0.038 Uiso 1 1 calc R U . . .
H31C H 0.356093 0.417307 0.183319 0.038 Uiso 1 1 calc R U . . .
C41 C 0.06607(13) 0.38813(7) 0.54352(7) 0.0291(3) Uani 1 1 d . . . . .
H41A H 0.140160 0.360364 0.553441 0.044 Uiso 1 1 calc R U . . .
H41B H -0.000915 0.359506 0.549692 0.044 Uiso 1 1 calc R U . . .
H41C H 0.079422 0.426384 0.580525 0.044 Uiso 1 1 calc R U . . .
C51 C 0.18185(12) 0.55961(6) 0.19980(7) 0.0245(2) Uani 1 1 d . . . . .
C52 C 0.23567(15) 0.60205(6) 0.26313(7) 0.0318(3) Uani 1 1 d . . . . .
C53 C 0.35149(15) 0.62688(7) 0.26905(8) 0.0378(3) Uani 1 1 d . . . . .
H53 H 0.388969 0.656749 0.310840 0.045 Uiso 1 1 calc R U . . .
C54 C 0.41435(14) 0.60943(7) 0.21579(9) 0.0374(3) Uani 1 1 d . . . . .
C55 C 0.35742(13) 0.56715(7) 0.15333(8) 0.0316(3) Uani 1 1 d . . . . .
H55 H 0.399776 0.554733 0.116783 0.038 Uiso 1 1 calc R U . . .
C56 C 0.23994(12) 0.54275(6) 0.14336(7) 0.0247(2) Uani 1 1 d . . . . .
C57 C 0.17119(19) 0.61993(8) 0.32311(8) 0.0443(4) Uani 1 1 d . . . . .
H57A H 0.085998 0.630769 0.297078 0.066 Uiso 1 1 calc R U . . .
H57B H 0.210444 0.659881 0.353144 0.066 Uiso 1 1 calc R U . . .
H57C H 0.175209 0.580764 0.358119 0.066 Uiso 1 1 calc R U . . .
C58 C 0.53992(17) 0.63744(10) 0.22380(13) 0.0571(5) Uani 1 1 d . . . . .
H58A H 0.535150 0.687182 0.214888 0.086 Uiso 1 1 calc R U . . .
H58B H 0.574008 0.615366 0.185477 0.086 Uiso 1 1 calc R U . . .
H58C H 0.592179 0.627959 0.276255 0.086 Uiso 1 1 calc R U . . .
C59 C 0.17632(13) 0.50090(7) 0.07292(7) 0.0297(3) Uani 1 1 d . . . . .
H59A H 0.147576 0.457678 0.089587 0.045 Uiso 1 1 calc R U . . .
H59B H 0.233082 0.490926 0.042425 0.045 Uiso 1 1 calc R U . . .
H59C H 0.106942 0.526873 0.040961 0.045 Uiso 1 1 calc R U . . .
C61 C -0.14592(10) 0.39929(7) 0.19595(7) 0.0232(2) Uani 1 1 d . . . . .
C62 C -0.12879(10) 0.33947(7) 0.15702(7) 0.0240(2) Uani 1 1 d . . . . .
C63 C -0.19608(11) 0.28148(7) 0.16440(7) 0.0274(2) Uani 1 1 d . . . . .
H63 H -0.186912 0.240674 0.137492 0.033 Uiso 1 1 calc R U . . .
C64 C -0.27662(11) 0.28157(8) 0.21020(7) 0.0305(3) Uani 1 1 d . . . . .
C65 C -0.28862(11) 0.34151(8) 0.24918(7) 0.0323(3) Uani 1 1 d . . . . .
H65 H -0.341190 0.341766 0.281761 0.039 Uiso 1 1 calc R U . . .
C66 C -0.22602(10) 0.40134(8) 0.24207(7) 0.0279(3) Uani 1 1 d . . . . .
C67 C -0.03943(11) 0.33639(7) 0.10926(8) 0.0296(3) Uani 1 1 d . . . . .
H67A H -0.053806 0.375109 0.072839 0.044 Uiso 1 1 calc R U . . .
H67B H -0.050069 0.293111 0.080146 0.044 Uiso 1 1 calc R U . . .
H67C H 0.043578 0.338945 0.143784 0.044 Uiso 1 1 calc R U . . .
C68 C -0.34995(14) 0.21884(10) 0.21696(9) 0.0419(4) Uani 1 1 d . . . . .
H68A H -0.432626 0.223746 0.182494 0.063 Uiso 1 1 calc R U . . .
H68B H -0.353066 0.213963 0.270771 0.063 Uiso 1 1 calc R U . . .
H68C H -0.311849 0.177983 0.202001 0.063 Uiso 1 1 calc R U . . .
C69 C -0.24257(13) 0.46505(9) 0.28591(9) 0.0377(3) Uani 1 1 d . . . . .
H69A H -0.166355 0.491070 0.300812 0.057 Uiso 1 1 calc R U . . .
H69B H -0.265262 0.451839 0.332716 0.057 Uiso 1 1 calc R U . . .
H69C H -0.306863 0.493629 0.252708 0.057 Uiso 1 1 calc R U . . .
P1 P -0.21563(3) 0.74213(2) 0.02215(2) 0.02439(7) Uani 1 1 d . . . . .
F1 F -0.28635(9) 0.71952(5) 0.08311(5) 0.0435(2) Uani 1 1 d . . . . .
F2 F -0.20165(9) 0.66337(4) 0.00027(5) 0.0409(2) Uani 1 1 d . . . . .
F3 F -0.14505(8) 0.76557(5) -0.03904(6) 0.0400(2) Uani 1 1 d . . . . .
F4 F -0.22776(8) 0.82110(4) 0.04448(6) 0.0405(2) Uani 1 1 d . . . . .
F5 F -0.34202(8) 0.74748(5) -0.04439(5) 0.03834(19) Uani 1 1 d . . . . .
F6 F -0.08853(8) 0.73697(6) 0.08898(6) 0.0471(2) Uani 1 1 d . . . . .
O1S O -0.5198(4) 0.5058(2) -0.0050(4) 0.0338(8) Uani 0.5 1 d D U P A -1
C1S C -0.4489(2) 0.45902(17) 0.05019(15) 0.0330(6) Uani 0.5 1 d D U P A -1
H1SA H -0.438660 0.476846 0.103361 0.040 Uiso 0.5 1 calc R U P A -1
H1SB H -0.367264 0.454410 0.042142 0.040 Uiso 0.5 1 calc R U P A -1
C2S C -0.5101(4) 0.38948(15) 0.0417(2) 0.0335(6) Uani 0.5 1 d D U P A -1
H2SA H -0.518520 0.371489 -0.010606 0.050 Uiso 0.5 1 calc R U P A -1
H2SB H -0.590760 0.394145 0.049870 0.050 Uiso 0.5 1 calc R U P A -1
H2SC H -0.460882 0.357737 0.080350 0.050 Uiso 0.5 1 calc R U P A -1
C3S C -0.4634(2) 0.56935(13) -0.00188(15) 0.0266(5) Uani 0.5 1 d D U P A -1
H3SA H -0.379778 0.564246 -0.006344 0.032 Uiso 0.5 1 calc R U P A -1
H3SB H -0.460176 0.593393 0.047343 0.032 Uiso 0.5 1 calc R U P A -1
C4S C -0.5432(3) 0.60817(18) -0.07125(18) 0.0335(7) Uani 0.5 1 d D U P A -1
H4SA H -0.539920 0.585477 -0.119420 0.050 Uiso 0.5 1 calc R U P A -1
H4SB H -0.513894 0.655523 -0.070756 0.050 Uiso 0.5 1 calc R U P A -1
H4SC H -0.627249 0.608511 -0.068270 0.050 Uiso 0.5 1 calc R U P A -1
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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'
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
C1 Cu1 N1 130.30(4) . . ?
C1 Cu1 N2 135.79(4) . . ?
N1 Cu1 N2 79.33(3) . . ?
C1 Cu1 N3 129.30(4) . . ?
N1 Cu1 N3 80.93(3) . . ?
N2 Cu1 N3 80.86(3) . . ?
C12 N1 C16 118.83(9) . . ?
C12 N1 Cu1 113.07(7) . . ?
C16 N1 Cu1 124.79(7) . . ?
C22 N2 C26 118.75(9) . . ?
C22 N2 Cu1 113.31(7) . . ?
C26 N2 Cu1 124.78(7) . . ?
C11 N3 C21 112.03(9) . . ?
C11 N3 C31 108.52(9) . . ?
C21 N3 C31 107.78(9) . . ?
C11 N3 Cu1 104.46(6) . . ?
C21 N3 Cu1 105.74(6) . . ?
C31 N3 Cu1 118.36(7) . . ?
C41 N4 C17 114.82(11) . . ?
C41 N4 C27 114.35(10) . . ?
C17 N4 C27 117.57(9) . . ?
C1 N5 C2 111.91(11) . . ?
C1 N5 C51 123.14(10) . . ?
C2 N5 C51 124.38(11) . . ?
C1 N6 C3 111.50(11) . . ?
C1 N6 C61 124.59(9) . . ?
C3 N6 C61 123.82(11) . . ?
N5 C1 N6 103.08(9) . . ?
N5 C1 Cu1 126.69(9) . . ?
N6 C1 Cu1 130.09(9) . . ?
C3 C2 N5 106.52(12) . . ?
C3 C2 H2 126.7 . . ?
N5 C2 H2 126.7 . . ?
C2 C3 N6 106.99(11) . . ?
C2 C3 H3 126.5 . . ?
N6 C3 H3 126.5 . . ?
N3 C11 C12 113.12(9) . . ?
N3 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N3 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 C13 122.82(10) . . ?
N1 C12 C11 115.67(10) . . ?
C13 C12 C11 121.49(10) . . ?
C14 C13 C12 118.31(10) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 119.12(11) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 119.47(11) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N1 C16 C15 121.31(10) . . ?
N1 C16 C17 117.25(9) . . ?
C15 C16 C17 121.42(10) . . ?
N4 C17 C16 117.13(9) . . ?
N4 C17 H17A 108.0 . . ?
C16 C17 H17A 108.0 . . ?
N4 C17 H17B 108.0 . . ?
C16 C17 H17B 108.0 . . ?
H17A C17 H17B 107.3 . . ?
N3 C21 C22 113.31(8) . . ?
N3 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N3 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
N2 C22 C23 122.54(10) . . ?
N2 C22 C21 116.04(9) . . ?
C23 C22 C21 121.38(10) . . ?
C22 C23 C24 118.54(11) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 119.15(11) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 119.23(11) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
N2 C26 C25 121.51(10) . . ?
N2 C26 C27 117.15(10) . . ?
C25 C26 C27 121.28(10) . . ?
N4 C27 C26 115.83(9) . . ?
N4 C27 H27A 108.3 . . ?
C26 C27 H27A 108.3 . . ?
N4 C27 H27B 108.3 . . ?
C26 C27 H27B 108.3 . . ?
H27A C27 H27B 107.4 . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N4 C41 H41A 109.5 . . ?
N4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C56 C51 C52 122.30(13) . . ?
C56 C51 N5 117.75(11) . . ?
C52 C51 N5 119.95(12) . . ?
C53 C52 C51 117.48(13) . . ?
C53 C52 C57 121.04(13) . . ?
C51 C52 C57 121.48(14) . . ?
C52 C53 C54 122.12(13) . . ?
C52 C53 H53 118.9 . . ?
C54 C53 H53 118.9 . . ?
C53 C54 C55 118.64(14) . . ?
C53 C54 C58 120.78(15) . . ?
C55 C54 C58 120.55(17) . . ?
C56 C55 C54 121.46(14) . . ?
C56 C55 H55 119.3 . . ?
C54 C55 H55 119.3 . . ?
C55 C56 C51 117.92(12) . . ?
C55 C56 C59 120.99(12) . . ?
C51 C56 C59 121.07(12) . . ?
C52 C57 H57A 109.5 . . ?
C52 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C52 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C54 C58 H58A 109.5 . . ?
C54 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C54 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C56 C59 H59A 109.5 . . ?
C56 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C56 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C66 C61 C62 121.76(12) . . ?
C66 C61 N6 119.30(11) . . ?
C62 C61 N6 118.94(10) . . ?
C63 C62 C61 117.83(10) . . ?
C63 C62 C67 120.24(11) . . ?
C61 C62 C67 121.92(12) . . ?
C62 C63 C64 121.97(12) . . ?
C62 C63 H63 119.0 . . ?
C64 C63 H63 119.0 . . ?
C65 C64 C63 118.23(13) . . ?
C65 C64 C68 120.29(12) . . ?
C63 C64 C68 121.48(13) . . ?
C64 C65 C66 122.03(11) . . ?
C64 C65 H65 119.0 . . ?
C66 C65 H65 119.0 . . ?
C65 C66 C61 118.13(12) . . ?
C65 C66 C69 119.72(11) . . ?
C61 C66 C69 122.11(13) . . ?
C62 C67 H67A 109.5 . . ?
C62 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C62 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C64 C68 H68A 109.5 . . ?
C64 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C64 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C66 C69 H69A 109.5 . . ?
C66 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C66 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
F1 P1 F5 90.01(5) . . ?
F1 P1 F2 90.52(6) . . ?
F5 P1 F2 90.68(5) . . ?
F1 P1 F3 179.46(6) . . ?
F5 P1 F3 89.84(5) . . ?
F2 P1 F3 90.01(5) . . ?
F1 P1 F4 89.81(5) . . ?
F5 P1 F4 89.98(5) . . ?
F2 P1 F4 179.26(6) . . ?
F3 P1 F4 89.66(5) . . ?
F1 P1 F6 90.07(5) . . ?
F5 P1 F6 179.84(6) . . ?
F2 P1 F6 89.46(5) . . ?
F3 P1 F6 90.07(5) . . ?
F4 P1 F6 89.88(6) . . ?
C3S O1S C1S 112.0(4) . . ?
O1S C1S C2S 110.1(3) . . ?
O1S C1S H1SA 109.6 . . ?
C2S C1S H1SA 109.6 . . ?
O1S C1S H1SB 109.6 . . ?
C2S C1S H1SB 109.6 . . ?
H1SA C1S H1SB 108.1 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
O1S C3S C4S 104.1(3) . . ?
O1S C3S H3SA 110.9 . . ?
C4S C3S H3SA 110.9 . . ?
O1S C3S H3SB 110.9 . . ?
C4S C3S H3SB 110.9 . . ?
H3SA C3S H3SB 109.0 . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 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
Cu1 C1 1.9037(11) . ?
Cu1 N1 2.1280(9) . ?
Cu1 N2 2.1286(9) . ?
Cu1 N3 2.2048(9) . ?
N1 C12 1.3459(13) . ?
N1 C16 1.3467(13) . ?
N2 C22 1.3472(13) . ?
N2 C26 1.3478(13) . ?
N3 C11 1.4785(14) . ?
N3 C21 1.4790(14) . ?
N3 C31 1.4815(14) . ?
N4 C41 1.4510(15) . ?
N4 C17 1.4624(16) . ?
N4 C27 1.4672(16) . ?
N5 C1 1.3675(15) . ?
N5 C2 1.3939(16) . ?
N5 C51 1.4352(17) . ?
N6 C1 1.3689(15) . ?
N6 C3 1.3953(16) . ?
N6 C61 1.4362(17) . ?
C2 C3 1.339(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C11 C12 1.5078(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3882(16) . ?
C13 C14 1.3861(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3884(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3927(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.5165(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C21 C22 1.5082(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.3876(15) . ?
C23 C24 1.3885(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3845(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.3945(16) . ?
C25 H25 0.9500 . ?
C26 C27 1.5140(16) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C51 C56 1.3980(17) . ?
C51 C52 1.3992(17) . ?
C52 C53 1.389(2) . ?
C52 C57 1.507(2) . ?
C53 C54 1.391(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.395(2) . ?
C54 C58 1.508(2) . ?
C55 C56 1.3917(19) . ?
C55 H55 0.9500 . ?
C56 C59 1.5072(17) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C61 C66 1.3986(15) . ?
C61 C62 1.3990(17) . ?
C62 C63 1.3941(18) . ?
C62 C67 1.5101(15) . ?
C63 C64 1.3978(16) . ?
C63 H63 0.9500 . ?
C64 C65 1.386(2) . ?
C64 C68 1.506(2) . ?
C65 C66 1.392(2) . ?
C65 H65 0.9500 . ?
C66 C69 1.5079(19) . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
P1 F1 1.5951(9) . ?
P1 F5 1.6007(8) . ?
P1 F2 1.6010(9) . ?
P1 F3 1.6018(9) . ?
P1 F4 1.6037(9) . ?
P1 F6 1.6087(9) . ?
O1S C3S 1.389(6) . ?
O1S C1S 1.420(4) . ?
C1S C2S 1.513(4) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C3S C4S 1.521(4) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
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
C2 N5 C1 N6 0.13(13) . . . . ?
C51 N5 C1 N6 -171.59(10) . . . . ?
C2 N5 C1 Cu1 -175.79(9) . . . . ?
C51 N5 C1 Cu1 12.49(15) . . . . ?
C3 N6 C1 N5 -0.22(13) . . . . ?
C61 N6 C1 N5 176.44(10) . . . . ?
C3 N6 C1 Cu1 175.51(9) . . . . ?
C61 N6 C1 Cu1 -7.84(16) . . . . ?
C1 N5 C2 C3 0.00(15) . . . . ?
C51 N5 C2 C3 171.60(11) . . . . ?
N5 C2 C3 N6 -0.13(15) . . . . ?
C1 N6 C3 C2 0.23(15) . . . . ?
C61 N6 C3 C2 -176.46(11) . . . . ?
C21 N3 C11 C12 -77.61(11) . . . . ?
C31 N3 C11 C12 163.52(10) . . . . ?
Cu1 N3 C11 C12 36.39(11) . . . . ?
C16 N1 C12 C13 -2.20(16) . . . . ?
Cu1 N1 C12 C13 -162.66(9) . . . . ?
C16 N1 C12 C11 179.51(10) . . . . ?
Cu1 N1 C12 C11 19.05(12) . . . . ?
N3 C11 C12 N1 -39.50(14) . . . . ?
N3 C11 C12 C13 142.18(11) . . . . ?
N1 C12 C13 C14 -1.12(18) . . . . ?
C11 C12 C13 C14 177.08(11) . . . . ?
C12 C13 C14 C15 2.54(19) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C12 N1 C16 C15 4.08(16) . . . . ?
Cu1 N1 C16 C15 162.07(9) . . . . ?
C12 N1 C16 C17 -174.27(10) . . . . ?
Cu1 N1 C16 C17 -16.28(14) . . . . ?
C14 C15 C16 N1 -2.64(19) . . . . ?
C14 C15 C16 C17 175.64(12) . . . . ?
C41 N4 C17 C16 63.78(13) . . . . ?
C27 N4 C17 C16 -75.15(13) . . . . ?
N1 C16 C17 N4 98.12(12) . . . . ?
C15 C16 C17 N4 -80.23(14) . . . . ?
C11 N3 C21 C22 80.67(11) . . . . ?
C31 N3 C21 C22 -160.02(9) . . . . ?
Cu1 N3 C21 C22 -32.54(10) . . . . ?
C26 N2 C22 C23 1.28(16) . . . . ?
Cu1 N2 C22 C23 162.18(9) . . . . ?
C26 N2 C22 C21 178.89(9) . . . . ?
Cu1 N2 C22 C21 -20.21(11) . . . . ?
N3 C21 C22 N2 37.27(13) . . . . ?
N3 C21 C22 C23 -145.09(10) . . . . ?
N2 C22 C23 C24 3.06(17) . . . . ?
C21 C22 C23 C24 -174.43(11) . . . . ?
C22 C23 C24 C25 -3.33(18) . . . . ?
C23 C24 C25 C26 -0.50(18) . . . . ?
C22 N2 C26 C25 -5.34(16) . . . . ?
Cu1 N2 C26 C25 -163.87(8) . . . . ?
C22 N2 C26 C27 172.01(10) . . . . ?
Cu1 N2 C26 C27 13.48(14) . . . . ?
C24 C25 C26 N2 4.98(18) . . . . ?
C24 C25 C26 C27 -172.26(11) . . . . ?
C41 N4 C27 C26 -63.29(13) . . . . ?
C17 N4 C27 C26 75.84(13) . . . . ?
N2 C26 C27 N4 -97.71(12) . . . . ?
C25 C26 C27 N4 79.64(14) . . . . ?
C1 N5 C51 C56 86.70(14) . . . . ?
C2 N5 C51 C56 -83.99(15) . . . . ?
C1 N5 C51 C52 -93.82(14) . . . . ?
C2 N5 C51 C52 95.50(15) . . . . ?
C56 C51 C52 C53 -0.77(18) . . . . ?
N5 C51 C52 C53 179.77(11) . . . . ?
C56 C51 C52 C57 179.65(12) . . . . ?
N5 C51 C52 C57 0.19(18) . . . . ?
C51 C52 C53 C54 -1.60(19) . . . . ?
C57 C52 C53 C54 177.99(13) . . . . ?
C52 C53 C54 C55 1.8(2) . . . . ?
C52 C53 C54 C58 179.85(13) . . . . ?
C53 C54 C55 C56 0.3(2) . . . . ?
C58 C54 C55 C56 -177.69(13) . . . . ?
C54 C55 C56 C51 -2.56(18) . . . . ?
C54 C55 C56 C59 176.01(12) . . . . ?
C52 C51 C56 C55 2.80(17) . . . . ?
N5 C51 C56 C55 -177.73(10) . . . . ?
C52 C51 C56 C59 -175.78(11) . . . . ?
N5 C51 C56 C59 3.69(16) . . . . ?
C1 N6 C61 C66 110.54(13) . . . . ?
C3 N6 C61 C66 -73.21(15) . . . . ?
C1 N6 C61 C62 -70.23(15) . . . . ?
C3 N6 C61 C62 106.02(13) . . . . ?
C66 C61 C62 C63 1.10(17) . . . . ?
N6 C61 C62 C63 -178.11(10) . . . . ?
C66 C61 C62 C67 -178.00(11) . . . . ?
N6 C61 C62 C67 2.79(17) . . . . ?
C61 C62 C63 C64 -1.32(18) . . . . ?
C67 C62 C63 C64 177.79(12) . . . . ?
C62 C63 C64 C65 -0.15(19) . . . . ?
C62 C63 C64 C68 179.26(13) . . . . ?
C63 C64 C65 C66 1.9(2) . . . . ?
C68 C64 C65 C66 -177.49(13) . . . . ?
C64 C65 C66 C61 -2.14(19) . . . . ?
C64 C65 C66 C69 -179.97(13) . . . . ?
C62 C61 C66 C65 0.57(18) . . . . ?
N6 C61 C66 C65 179.78(11) . . . . ?
C62 C61 C66 C69 178.36(12) . . . . ?
N6 C61 C66 C69 -2.43(18) . . . . ?
C3S O1S C1S C2S -176.9(4) . . . . ?
C1S O1S C3S C4S 172.5(4) . . . . ?
