#------------------------------------------------------------------------------
#$Date: 2020-09-22 04:25:22 +0300 (Tue, 22 Sep 2020) $
#$Revision: 256608 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/91/1559137.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_1559137
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_absolute_configuration ad
_chemical_formula_moiety         'C43 H56 Cu N6 1+, F6 P 1-, C H2 Cl2'
_chemical_formula_sum            'C44 H58 Cl2 Cu F6 N6 P'
_chemical_formula_weight         950.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1264(7)
_cell_length_b                   18.4915(15)
_cell_length_c                   19.9843(14)
_cell_measurement_reflns_used    18216
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      29.9470
_cell_measurement_theta_min      2.3570
_cell_volume                     4481.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (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      95(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0350
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41059
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.648
_diffrn_reflns_theta_min         1.964
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (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    1.409
_exptl_crystal_description       prism
_exptl_crystal_F_000             1984
_exptl_crystal_recrystallization_method
'vapor diffusion in a DCM-diethyl ether system at r.t.'
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 4130 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         10348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0308
_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)+(0.0391P)²+1.6121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                9808
_reflns_number_total             10348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04442c7.cif
_cod_data_source_block           jk161
_cod_database_code               1559137
_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   0.844
_shelx_estimated_absorpt_t_max   0.941
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Cu1 Cu 0.21394(2) 0.65303(2) 0.70401(2) 0.01376(7) Uani 1 1 d . . . . .
N1 N 0.22432(17) 0.69675(11) 0.80161(10) 0.0154(4) Uani 1 1 d . . . . .
N2 N 0.17090(17) 0.76061(12) 0.68356(10) 0.0157(4) Uani 1 1 d . . . . .
N3 N 0.03987(16) 0.64791(13) 0.73183(10) 0.0171(4) Uani 1 1 d . . . . .
N4 N 0.4227(2) 0.80182(13) 0.73789(13) 0.0240(5) Uani 1 1 d . . . . .
N5 N 0.38267(16) 0.54664(11) 0.66528(10) 0.0132(4) Uani 1 1 d . . . . .
N6 N 0.25953(16) 0.55630(11) 0.58931(10) 0.0142(4) Uani 1 1 d . . . . .
C1 C 0.2863(2) 0.58171(13) 0.65175(11) 0.0130(4) Uani 1 1 d . . . . .
C2 C 0.4154(2) 0.50224(14) 0.61269(13) 0.0174(5) Uani 1 1 d . . . . .
H2 H 0.479910 0.473142 0.610885 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3381(2) 0.50854(15) 0.56509(13) 0.0181(5) Uani 1 1 d . . . . .
H3 H 0.337386 0.484870 0.522901 0.022 Uiso 1 1 calc R U . . .
C11 C 0.0350(2) 0.65557(16) 0.80534(12) 0.0199(5) Uani 1 1 d . . . . .
H11A H 0.036304 0.606817 0.825801 0.024 Uiso 1 1 calc R U . . .
H11B H -0.035799 0.678661 0.817637 0.024 Uiso 1 1 calc R U . . .
C12 C 0.1280(2) 0.69949(14) 0.83398(13) 0.0176(5) Uani 1 1 d . . . . .
C13 C 0.1133(3) 0.73879(17) 0.89233(15) 0.0271(6) Uani 1 1 d . . . . .
H13 H 0.044009 0.738975 0.914560 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2003(3) 0.77732(18) 0.91733(15) 0.0338(7) Uani 1 1 d . . . . .
H14 H 0.192373 0.804556 0.957339 0.041 Uiso 1 1 calc R U . . .
C15 C 0.2999(3) 0.77622(17) 0.88383(15) 0.0292(7) Uani 1 1 d . . . . .
H15 H 0.361382 0.802398 0.900640 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3090(2) 0.73621(14) 0.82509(14) 0.0193(5) Uani 1 1 d . . . . .
C17 C 0.4119(2) 0.73962(15) 0.78310(14) 0.0213(5) Uani 1 1 d . . . . .
H17A H 0.476318 0.739425 0.813569 0.026 Uiso 1 1 calc R U . . .
H17B H 0.415841 0.694961 0.755873 0.026 Uiso 1 1 calc R U . . .
C21 C -0.0108(2) 0.70922(16) 0.69626(14) 0.0217(6) Uani 1 1 d . . . . .
H21A H -0.078552 0.723811 0.720397 0.026 Uiso 1 1 calc R U . . .
H21B H -0.032936 0.693005 0.651000 0.026 Uiso 1 1 calc R U . . .
C22 C 0.0632(2) 0.77418(15) 0.68948(13) 0.0189(5) Uani 1 1 d . . . . .
C23 C 0.0211(2) 0.84382(18) 0.68516(14) 0.0274(6) Uani 1 1 d . . . . .
H23 H -0.055937 0.852107 0.689415 0.033 Uiso 1 1 calc R U . . .
C24 C 0.0918(3) 0.90046(16) 0.67469(16) 0.0298(7) Uani 1 1 d . . . . .
H24 H 0.064234 0.948312 0.670227 0.036 Uiso 1 1 calc R U . . .
C25 C 0.2037(3) 0.88711(15) 0.67071(14) 0.0258(6) Uani 1 1 d . . . . .
H25 H 0.254227 0.925748 0.664376 0.031 Uiso 1 1 calc R U . . .
C26 C 0.2412(2) 0.81619(15) 0.67613(13) 0.0195(5) Uani 1 1 d . . . . .
C27 C 0.3635(2) 0.79881(15) 0.67450(15) 0.0220(6) Uani 1 1 d . . . . .
H27A H 0.372476 0.749585 0.655786 0.026 Uiso 1 1 calc R U . . .
H27B H 0.399527 0.832841 0.643099 0.026 Uiso 1 1 calc R U . . .
C31 C -0.0172(2) 0.58083(16) 0.71353(15) 0.0252(6) Uani 1 1 d . . . . .
H31A H -0.092664 0.581993 0.730983 0.038 Uiso 1 1 calc R U . . .
H31B H 0.022220 0.539442 0.732682 0.038 Uiso 1 1 calc R U . . .
H31C H -0.019154 0.576243 0.664690 0.038 Uiso 1 1 calc R U . . .
C41 C 0.4184(3) 0.87196(17) 0.77092(18) 0.0362(8) Uani 1 1 d . . . . .
H41A H 0.436938 0.910019 0.738706 0.054 Uiso 1 1 calc R U . . .
H41B H 0.471316 0.872856 0.807952 0.054 Uiso 1 1 calc R U . . .
H41C H 0.343862 0.880220 0.788331 0.054 Uiso 1 1 calc R U . . .
C51 C 0.44448(19) 0.55125(14) 0.72704(12) 0.0135(5) Uani 1 1 d . . . . .
C52 C 0.5518(2) 0.57929(14) 0.72450(12) 0.0158(5) Uani 1 1 d . . . . .
C521 C 0.6034(2) 0.61058(18) 0.66139(14) 0.0266(6) Uani 1 1 d . . . . .
H521 H 0.544621 0.614618 0.626474 0.032 Uiso 1 1 calc R U . . .
C522 C 0.6491(3) 0.6865(2) 0.67513(16) 0.0378(8) Uani 1 1 d . . . . .
H52A H 0.589130 0.718148 0.690010 0.057 Uiso 1 1 calc R U . . .
H52B H 0.681718 0.705991 0.634066 0.057 Uiso 1 1 calc R U . . .
H52C H 0.705610 0.683729 0.710080 0.057 Uiso 1 1 calc R U . . .
C523 C 0.6938(2) 0.5613(2) 0.63476(17) 0.0413(9) Uani 1 1 d . . . . .
H52D H 0.750803 0.555219 0.669037 0.062 Uiso 1 1 calc R U . . .
H52E H 0.726481 0.583009 0.594648 0.062 Uiso 1 1 calc R U . . .
H52F H 0.662263 0.514103 0.623443 0.062 Uiso 1 1 calc R U . . .
C53 C 0.6134(2) 0.57745(15) 0.78350(13) 0.0185(5) Uani 1 1 d . . . . .
H53 H 0.687717 0.593784 0.782767 0.022 Uiso 1 1 calc R U . . .
C54 C 0.5696(2) 0.55266(15) 0.84259(13) 0.0189(5) Uani 1 1 d . . . . .
H54 H 0.612719 0.553049 0.882259 0.023 Uiso 1 1 calc R U . . .
C55 C 0.4624(2) 0.52712(15) 0.84416(13) 0.0200(5) Uani 1 1 d . . . . .
H55 H 0.432045 0.510884 0.885333 0.024 Uiso 1 1 calc R U . . .
C56 C 0.3981(2) 0.52480(15) 0.78645(13) 0.0175(5) Uani 1 1 d . . . . .
C561 C 0.2843(2) 0.49065(19) 0.78893(15) 0.0325(7) Uani 1 1 d . . . . .
H561 H 0.238013 0.516536 0.755168 0.039 Uiso 1 1 calc R U . . .
C562 C 0.2269(2) 0.49880(17) 0.85575(16) 0.0291(6) Uani 1 1 d . . . . .
H56A H 0.150658 0.481784 0.851929 0.044 Uiso 1 1 calc R U . . .
H56B H 0.227208 0.549813 0.869037 0.044 Uiso 1 1 calc R U . . .
H56C H 0.265771 0.470074 0.889562 0.044 Uiso 1 1 calc R U . . .
C563 C 0.2903(4) 0.4141(3) 0.7675(3) 0.090(2) Uani 1 1 d . . . . .
H56D H 0.326843 0.411165 0.723835 0.135 Uiso 1 1 calc R U . . .
H56E H 0.215520 0.394331 0.763923 0.135 Uiso 1 1 calc R U . . .
H56F H 0.332312 0.386249 0.800452 0.135 Uiso 1 1 calc R U . . .
C61 C 0.1556(2) 0.56858(15) 0.55596(12) 0.0159(5) Uani 1 1 d . . . . .
C62 C 0.0798(2) 0.51185(15) 0.55319(13) 0.0189(5) Uani 1 1 d . . . . .
C621 C 0.1026(2) 0.43638(16) 0.58035(14) 0.0245(6) Uani 1 1 d . . . . .
H621 H 0.174423 0.437395 0.604895 0.029 Uiso 1 1 calc R U . . .
C622 C 0.0127(4) 0.4109(2) 0.6288(2) 0.0461(10) Uani 1 1 d . . . . .
H62A H 0.010781 0.442947 0.667814 0.069 Uiso 1 1 calc R U . . .
H62B H 0.028877 0.361385 0.643389 0.069 Uiso 1 1 calc R U . . .
H62C H -0.058974 0.411929 0.606191 0.069 Uiso 1 1 calc R U . . .
C623 C 0.1122(3) 0.38214(18) 0.52253(16) 0.0317(7) Uani 1 1 d . . . . .
H62D H 0.042426 0.380597 0.497797 0.048 Uiso 1 1 calc R U . . .
H62E H 0.128580 0.334009 0.540476 0.048 Uiso 1 1 calc R U . . .
H62F H 0.171644 0.397179 0.492379 0.048 Uiso 1 1 calc R U . . .
C63 C -0.0211(2) 0.52506(18) 0.52185(14) 0.0252(6) Uani 1 1 d . . . . .
H63 H -0.074505 0.487586 0.519465 0.030 Uiso 1 1 calc R U . . .
C64 C -0.0442(2) 0.59148(19) 0.49441(15) 0.0298(7) Uani 1 1 d . . . . .
H64 H -0.113813 0.599715 0.474004 0.036 Uiso 1 1 calc R U . . .
C65 C 0.0329(2) 0.64634(18) 0.49625(14) 0.0276(6) Uani 1 1 d . . . . .
H65 H 0.015920 0.691802 0.476663 0.033 Uiso 1 1 calc R U . . .
C66 C 0.1355(2) 0.63609(14) 0.52644(13) 0.0187(5) Uani 1 1 d . . . . .
C661 C 0.2223(3) 0.69497(15) 0.52422(13) 0.0248(6) Uani 1 1 d . . . . .
H661 H 0.262991 0.693610 0.567708 0.030 Uiso 1 1 calc R U . . .
C662 C 0.1742(3) 0.77100(18) 0.51644(16) 0.0360(8) Uani 1 1 d . . . . .
H66A H 0.140358 0.775732 0.472131 0.054 Uiso 1 1 calc R U . . .
H66B H 0.233250 0.806832 0.521197 0.054 Uiso 1 1 calc R U . . .
H66C H 0.118270 0.779157 0.551017 0.054 Uiso 1 1 calc R U . . .
C663 C 0.3057(3) 0.67921(18) 0.46860(16) 0.0334(7) Uani 1 1 d . . . . .
H66D H 0.340528 0.632195 0.476727 0.050 Uiso 1 1 calc R U . . .
H66E H 0.362287 0.717051 0.468162 0.050 Uiso 1 1 calc R U . . .
H66F H 0.267739 0.678295 0.425323 0.050 Uiso 1 1 calc R U . . .
P1 P 0.63354(5) 0.43111(4) 0.45899(3) 0.01672(14) Uani 1 1 d . . . . .
F1 F 0.65753(18) 0.51489(10) 0.46945(9) 0.0355(4) Uani 1 1 d . . . . .
F2 F 0.61146(13) 0.34628(9) 0.44840(8) 0.0251(3) Uani 1 1 d . . . . .
F3 F 0.50778(14) 0.44800(11) 0.44175(9) 0.0332(4) Uani 1 1 d . . . . .
F4 F 0.66408(14) 0.43831(10) 0.38098(8) 0.0262(4) Uani 1 1 d . . . . .
F5 F 0.76027(12) 0.41326(9) 0.47564(8) 0.0249(4) Uani 1 1 d . . . . .
F6 F 0.60325(14) 0.42198(9) 0.53661(8) 0.0266(4) Uani 1 1 d . . . . .
C01 C 0.3180(3) 0.2385(2) 0.6001(2) 0.0411(8) Uani 1 1 d . . . . .
H01A H 0.266267 0.220935 0.565390 0.049 Uiso 1 1 calc R U . . .
H01B H 0.364915 0.197363 0.614011 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.24342(10) 0.26960(6) 0.66871(5) 0.0569(3) Uani 1 1 d . . . . .
Cl2 Cl 0.40127(7) 0.30677(5) 0.56621(4) 0.03843(19) 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 0.0033 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'
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
_geom_angle_publ_flag
C1 Cu1 N2 131.85(9) . . ?
C1 Cu1 N1 138.22(9) . . ?
N2 Cu1 N1 80.32(8) . . ?
C1 Cu1 N3 123.83(10) . . ?
N2 Cu1 N3 81.39(9) . . ?
N1 Cu1 N3 80.76(8) . . ?
C12 N1 C16 118.6(2) . . ?
C12 N1 Cu1 114.13(17) . . ?
C16 N1 Cu1 125.10(18) . . ?
C22 N2 C26 119.1(2) . . ?
C22 N2 Cu1 113.86(18) . . ?
C26 N2 Cu1 126.11(18) . . ?
C31 N3 C21 109.5(2) . . ?
C31 N3 C11 108.1(2) . . ?
C21 N3 C11 112.9(2) . . ?
C31 N3 Cu1 115.39(17) . . ?
C21 N3 Cu1 104.30(15) . . ?
C11 N3 Cu1 106.71(14) . . ?
C41 N4 C27 114.2(2) . . ?
C41 N4 C17 114.5(2) . . ?
C27 N4 C17 117.5(2) . . ?
C1 N5 C2 112.1(2) . . ?
C1 N5 C51 125.8(2) . . ?
C2 N5 C51 122.1(2) . . ?
C1 N6 C3 111.9(2) . . ?
C1 N6 C61 124.9(2) . . ?
C3 N6 C61 122.6(2) . . ?
N5 C1 N6 102.7(2) . . ?
N5 C1 Cu1 128.16(17) . . ?
N6 C1 Cu1 128.98(18) . . ?
C3 C2 N5 106.6(2) . . ?
C3 C2 H2 126.7 . . ?
N5 C2 H2 126.7 . . ?
C2 C3 N6 106.8(2) . . ?
C2 C3 H3 126.6 . . ?
N6 C3 H3 126.6 . . ?
N3 C11 C12 113.6(2) . . ?
N3 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N3 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N1 C12 C13 122.7(3) . . ?
N1 C12 C11 116.8(2) . . ?
C13 C12 C11 120.5(2) . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N1 C16 C15 121.5(3) . . ?
N1 C16 C17 117.5(2) . . ?
C15 C16 C17 120.9(2) . . ?
N4 C17 C16 116.7(2) . . ?
N4 C17 H17A 108.1 . . ?
C16 C17 H17A 108.1 . . ?
N4 C17 H17B 108.1 . . ?
C16 C17 H17B 108.1 . . ?
H17A C17 H17B 107.3 . . ?
N3 C21 C22 114.2(2) . . ?
N3 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
N3 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
N2 C22 C23 121.9(3) . . ?
N2 C22 C21 116.2(2) . . ?
C23 C22 C21 121.8(2) . . ?
C24 C23 C22 119.3(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 119.2(3) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 119.0(3) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
N2 C26 C25 121.4(3) . . ?
N2 C26 C27 117.4(2) . . ?
C25 C26 C27 121.2(3) . . ?
N4 C27 C26 117.0(2) . . ?
N4 C27 H27A 108.0 . . ?
C26 C27 H27A 108.0 . . ?
N4 C27 H27B 108.0 . . ?
C26 C27 H27B 108.0 . . ?
H27A C27 H27B 107.3 . . ?
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 122.1(2) . . ?
C56 C51 N5 119.6(2) . . ?
C52 C51 N5 118.2(2) . . ?
C53 C52 C51 117.2(2) . . ?
C53 C52 C521 119.3(2) . . ?
C51 C52 C521 123.5(2) . . ?
C523 C521 C52 111.0(3) . . ?
C523 C521 C522 110.5(3) . . ?
C52 C521 C522 110.4(2) . . ?
C523 C521 H521 108.3 . . ?
C52 C521 H521 108.3 . . ?
C522 C521 H521 108.3 . . ?
C521 C522 H52A 109.5 . . ?
C521 C522 H52B 109.5 . . ?
H52A C522 H52B 109.5 . . ?
C521 C522 H52C 109.5 . . ?
H52A C522 H52C 109.5 . . ?
H52B C522 H52C 109.5 . . ?
C521 C523 H52D 109.5 . . ?
C521 C523 H52E 109.5 . . ?
H52D C523 H52E 109.5 . . ?
C521 C523 H52F 109.5 . . ?
H52D C523 H52F 109.5 . . ?
H52E C523 H52F 109.5 . . ?
C54 C53 C52 121.8(2) . . ?
C54 C53 H53 119.1 . . ?
C52 C53 H53 119.1 . . ?
C53 C54 C55 119.8(2) . . ?
C53 C54 H54 120.1 . . ?
C55 C54 H54 120.1 . . ?
C54 C55 C56 121.2(2) . . ?
C54 C55 H55 119.4 . . ?
C56 C55 H55 119.4 . . ?
C55 C56 C51 117.8(2) . . ?
C55 C56 C561 119.6(2) . . ?
C51 C56 C561 122.5(2) . . ?
C563 C561 C562 111.9(3) . . ?
C563 C561 C56 110.1(3) . . ?
C562 C561 C56 113.9(2) . . ?
C563 C561 H561 106.8 . . ?
C562 C561 H561 106.8 . . ?
C56 C561 H561 106.8 . . ?
C561 C562 H56A 109.5 . . ?
C561 C562 H56B 109.5 . . ?
H56A C562 H56B 109.5 . . ?
C561 C562 H56C 109.5 . . ?
H56A C562 H56C 109.5 . . ?
H56B C562 H56C 109.5 . . ?
C561 C563 H56D 109.5 . . ?
C561 C563 H56E 109.5 . . ?
H56D C563 H56E 109.5 . . ?
C561 C563 H56F 109.5 . . ?
H56D C563 H56F 109.5 . . ?
H56E C563 H56F 109.5 . . ?
C62 C61 C66 122.6(2) . . ?
C62 C61 N6 118.4(2) . . ?
C66 C61 N6 119.1(2) . . ?
C61 C62 C63 117.6(3) . . ?
C61 C62 C621 123.7(2) . . ?
C63 C62 C621 118.6(3) . . ?
C62 C621 C622 112.3(3) . . ?
C62 C621 C623 110.1(2) . . ?
C622 C621 C623 109.2(3) . . ?
C62 C621 H621 108.4 . . ?
C622 C621 H621 108.4 . . ?
C623 C621 H621 108.4 . . ?
C621 C622 H62A 109.5 . . ?
C621 C622 H62B 109.5 . . ?
H62A C622 H62B 109.5 . . ?
C621 C622 H62C 109.5 . . ?
H62A C622 H62C 109.5 . . ?
H62B C622 H62C 109.5 . . ?
C621 C623 H62D 109.5 . . ?
C621 C623 H62E 109.5 . . ?
H62D C623 H62E 109.5 . . ?
C621 C623 H62F 109.5 . . ?
H62D C623 H62F 109.5 . . ?
H62E C623 H62F 109.5 . . ?
C64 C63 C62 121.0(3) . . ?
C64 C63 H63 119.5 . . ?
C62 C63 H63 119.5 . . ?
C63 C64 C65 120.5(3) . . ?
C63 C64 H64 119.7 . . ?
C65 C64 H64 119.7 . . ?
C64 C65 C66 121.0(3) . . ?
C64 C65 H65 119.5 . . ?
C66 C65 H65 119.5 . . ?
C65 C66 C61 117.2(3) . . ?
C65 C66 C661 120.6(3) . . ?
C61 C66 C661 122.1(2) . . ?
C66 C661 C662 113.5(3) . . ?
C66 C661 C663 110.1(2) . . ?
C662 C661 C663 110.7(2) . . ?
C66 C661 H661 107.4 . . ?
C662 C661 H661 107.4 . . ?
C663 C661 H661 107.4 . . ?
C661 C662 H66A 109.5 . . ?
C661 C662 H66B 109.5 . . ?
H66A C662 H66B 109.5 . . ?
C661 C662 H66C 109.5 . . ?
H66A C662 H66C 109.5 . . ?
H66B C662 H66C 109.5 . . ?
C661 C663 H66D 109.5 . . ?
C661 C663 H66E 109.5 . . ?
H66D C663 H66E 109.5 . . ?
C661 C663 H66F 109.5 . . ?
H66D C663 H66F 109.5 . . ?
H66E C663 H66F 109.5 . . ?
F1 P1 F3 90.72(11) . . ?
F1 P1 F6 90.98(10) . . ?
F3 P1 F6 90.60(10) . . ?
F1 P1 F2 179.06(11) . . ?
F3 P1 F2 90.20(10) . . ?
F6 P1 F2 89.23(9) . . ?
F1 P1 F5 89.88(11) . . ?
F3 P1 F5 179.26(11) . . ?
F6 P1 F5 89.83(9) . . ?
F2 P1 F5 89.21(9) . . ?
F1 P1 F4 90.27(10) . . ?
F3 P1 F4 89.69(10) . . ?
F6 P1 F4 178.71(10) . . ?
F2 P1 F4 89.52(9) . . ?
F5 P1 F4 89.86(9) . . ?
Cl1 C01 Cl2 111.5(2) . . ?
Cl1 C01 H01A 109.3 . . ?
Cl2 C01 H01A 109.3 . . ?
Cl1 C01 H01B 109.3 . . ?
Cl2 C01 H01B 109.3 . . ?
H01A C01 H01B 108.0 . . ?
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 1.897(2) . ?
Cu1 N2 2.097(2) . ?
Cu1 N1 2.115(2) . ?
Cu1 N3 2.185(2) . ?
N1 C12 1.336(3) . ?
N1 C16 1.344(3) . ?
N2 C22 1.336(3) . ?
N2 C26 1.344(4) . ?
N3 C31 1.466(4) . ?
N3 C21 1.473(3) . ?
N3 C11 1.477(3) . ?
N4 C41 1.456(4) . ?
N4 C27 1.457(4) . ?
N4 C17 1.469(4) . ?
N5 C1 1.364(3) . ?
N5 C2 1.391(3) . ?
N5 C51 1.447(3) . ?
N6 C1 1.372(3) . ?
N6 C3 1.387(3) . ?
N6 C61 1.443(3) . ?
C2 C3 1.340(4) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C11 C12 1.503(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.385(4) . ?
C13 C14 1.368(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.506(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C21 C22 1.505(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.388(4) . ?
C23 C24 1.370(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.518(4) . ?
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 1.402(4) . ?
C51 C52 1.402(3) . ?
C52 C53 1.396(3) . ?
C52 C521 1.522(4) . ?
C521 C523 1.521(5) . ?
C521 C522 1.533(5) . ?
C521 H521 1.0000 . ?
C522 H52A 0.9800 . ?
C522 H52B 0.9800 . ?
C522 H52C 0.9800 . ?
C523 H52D 0.9800 . ?
C523 H52E 0.9800 . ?
C523 H52F 0.9800 . ?
C53 C54 1.374(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.383(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.392(4) . ?
C55 H55 0.9500 . ?
C56 C561 1.518(4) . ?
C561 C563 1.480(6) . ?
C561 C562 1.513(4) . ?
C561 H561 1.0000 . ?
C562 H56A 0.9800 . ?
C562 H56B 0.9800 . ?
C562 H56C 0.9800 . ?
C563 H56D 0.9800 . ?
C563 H56E 0.9800 . ?
C563 H56F 0.9800 . ?
C61 C62 1.396(4) . ?
C61 C66 1.402(4) . ?
C62 C63 1.396(4) . ?
C62 C621 1.523(4) . ?
C621 C622 1.532(4) . ?
C621 C623 1.535(4) . ?
C621 H621 1.0000 . ?
C622 H62A 0.9800 . ?
C622 H62B 0.9800 . ?
C622 H62C 0.9800 . ?
C623 H62D 0.9800 . ?
C623 H62E 0.9800 . ?
C623 H62F 0.9800 . ?
C63 C64 1.374(5) . ?
C63 H63 0.9500 . ?
C64 C65 1.380(5) . ?
C64 H64 0.9500 . ?
C65 C66 1.396(4) . ?
C65 H65 0.9500 . ?
C66 C661 1.514(4) . ?
C661 C662 1.530(4) . ?
C661 C663 1.531(4) . ?
C661 H661 1.0000 . ?
C662 H66A 0.9800 . ?
C662 H66B 0.9800 . ?
C662 H66C 0.9800 . ?
C663 H66D 0.9800 . ?
C663 H66E 0.9800 . ?
C663 H66F 0.9800 . ?
P1 F1 1.5902(19) . ?
P1 F3 1.5944(18) . ?
P1 F6 1.6030(17) . ?
P1 F2 1.6053(18) . ?
P1 F5 1.6066(17) . ?
P1 F4 1.6077(16) . ?
C01 Cl1 1.740(4) . ?
C01 Cl2 1.752(4) . ?
C01 H01A 0.9900 . ?
C01 H01B 0.9900 . ?
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 1.1(3) . . . . ?
C51 N5 C1 N6 -176.8(2) . . . . ?
C2 N5 C1 Cu1 -174.86(18) . . . . ?
C51 N5 C1 Cu1 7.2(3) . . . . ?
C3 N6 C1 N5 -1.2(3) . . . . ?
C61 N6 C1 N5 170.3(2) . . . . ?
C3 N6 C1 Cu1 174.68(19) . . . . ?
C61 N6 C1 Cu1 -13.8(4) . . . . ?
N2 Cu1 C1 N5 119.8(2) . . . . ?
N1 Cu1 C1 N5 -11.8(3) . . . . ?
N3 Cu1 C1 N5 -129.2(2) . . . . ?
N2 Cu1 C1 N6 -55.1(3) . . . . ?
N1 Cu1 C1 N6 173.27(18) . . . . ?
N3 Cu1 C1 N6 55.9(2) . . . . ?
C1 N5 C2 C3 -0.6(3) . . . . ?
C51 N5 C2 C3 177.4(2) . . . . ?
N5 C2 C3 N6 -0.2(3) . . . . ?
C1 N6 C3 C2 0.9(3) . . . . ?
C61 N6 C3 C2 -170.9(2) . . . . ?
C31 N3 C11 C12 153.8(2) . . . . ?
C21 N3 C11 C12 -84.9(3) . . . . ?
Cu1 N3 C11 C12 29.1(3) . . . . ?
C16 N1 C12 C13 -2.9(4) . . . . ?
Cu1 N1 C12 C13 -166.9(2) . . . . ?
C16 N1 C12 C11 179.0(2) . . . . ?
Cu1 N1 C12 C11 15.0(3) . . . . ?
N3 C11 C12 N1 -31.0(3) . . . . ?
N3 C11 C12 C13 150.8(3) . . . . ?
N1 C12 C13 C14 1.1(4) . . . . ?
C11 C12 C13 C14 179.1(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C12 N1 C16 C15 3.6(4) . . . . ?
Cu1 N1 C16 C15 165.6(2) . . . . ?
C12 N1 C16 C17 -172.5(2) . . . . ?
Cu1 N1 C16 C17 -10.4(3) . . . . ?
C14 C15 C16 N1 -2.3(4) . . . . ?
C14 C15 C16 C17 173.6(3) . . . . ?
C41 N4 C17 C16 57.8(3) . . . . ?
C27 N4 C17 C16 -80.3(3) . . . . ?
N1 C16 C17 N4 95.1(3) . . . . ?
C15 C16 C17 N4 -80.9(3) . . . . ?
C31 N3 C21 C22 -157.9(2) . . . . ?
C11 N3 C21 C22 81.6(3) . . . . ?
Cu1 N3 C21 C22 -33.9(3) . . . . ?
C26 N2 C22 C23 3.0(4) . . . . ?
Cu1 N2 C22 C23 172.7(2) . . . . ?
C26 N2 C22 C21 178.8(2) . . . . ?
Cu1 N2 C22 C21 -11.4(3) . . . . ?
N3 C21 C22 N2 32.5(3) . . . . ?
N3 C21 C22 C23 -151.6(3) . . . . ?
N2 C22 C23 C24 -0.2(4) . . . . ?
C21 C22 C23 C24 -175.8(3) . . . . ?
C22 C23 C24 C25 -1.9(5) . . . . ?
C23 C24 C25 C26 1.3(5) . . . . ?
C22 N2 C26 C25 -3.7(4) . . . . ?
Cu1 N2 C26 C25 -172.1(2) . . . . ?
C22 N2 C26 C27 175.8(2) . . . . ?
Cu1 N2 C26 C27 7.4(3) . . . . ?
C24 C25 C26 N2 1.6(4) . . . . ?
C24 C25 C26 C27 -177.9(3) . . . . ?
C41 N4 C27 C26 -58.8(3) . . . . ?
C17 N4 C27 C26 79.5(3) . . . . ?
N2 C26 C27 N4 -92.6(3) . . . . ?
C25 C26 C27 N4 86.8(3) . . . . ?
C1 N5 C51 C56 64.9(3) . . . . ?
C2 N5 C51 C56 -112.8(3) . . . . ?
C1 N5 C51 C52 -118.1(3) . . . . ?
C2 N5 C51 C52 64.2(3) . . . . ?
C56 C51 C52 C53 2.4(4) . . . . ?
N5 C51 C52 C53 -174.6(2) . . . . ?
C56 C51 C52 C521 -178.0(3) . . . . ?
N5 C51 C52 C521 5.0(4) . . . . ?
C53 C52 C521 C523 69.9(3) . . . . ?
C51 C52 C521 C523 -109.7(3) . . . . ?
C53 C52 C521 C522 -53.0(4) . . . . ?
C51 C52 C521 C522 127.5(3) . . . . ?
C51 C52 C53 C54 -3.2(4) . . . . ?
C521 C52 C53 C54 177.2(3) . . . . ?
C52 C53 C54 C55 1.5(4) . . . . ?
C53 C54 C55 C56 1.2(4) . . . . ?
C54 C55 C56 C51 -1.9(4) . . . . ?
C54 C55 C56 C561 174.9(3) . . . . ?
C52 C51 C56 C55 0.1(4) . . . . ?
N5 C51 C56 C55 177.0(2) . . . . ?
C52 C51 C56 C561 -176.6(3) . . . . ?
N5 C51 C56 C561 0.3(4) . . . . ?
C55 C56 C561 C563 -95.1(4) . . . . ?
C51 C56 C561 C563 81.6(4) . . . . ?
C55 C56 C561 C562 31.6(4) . . . . ?
C51 C56 C561 C562 -151.8(3) . . . . ?
C1 N6 C61 C62 -104.2(3) . . . . ?
C3 N6 C61 C62 66.5(3) . . . . ?
C1 N6 C61 C66 77.2(3) . . . . ?
C3 N6 C61 C66 -112.1(3) . . . . ?
C66 C61 C62 C63 -2.6(4) . . . . ?
N6 C61 C62 C63 178.8(2) . . . . ?
C66 C61 C62 C621 175.4(2) . . . . ?
N6 C61 C62 C621 -3.1(4) . . . . ?
C61 C62 C621 C622 127.1(3) . . . . ?
C63 C62 C621 C622 -54.9(4) . . . . ?
C61 C62 C621 C623 -111.0(3) . . . . ?
C63 C62 C621 C623 67.0(3) . . . . ?
C61 C62 C63 C64 0.4(4) . . . . ?
C621 C62 C63 C64 -177.7(3) . . . . ?
C62 C63 C64 C65 1.1(4) . . . . ?
C63 C64 C65 C66 -0.6(4) . . . . ?
C64 C65 C66 C61 -1.4(4) . . . . ?
C64 C65 C66 C661 176.0(3) . . . . ?
C62 C61 C66 C65 3.1(4) . . . . ?
N6 C61 C66 C65 -178.4(2) . . . . ?
C62 C61 C66 C661 -174.3(2) . . . . ?
N6 C61 C66 C661 4.3(4) . . . . ?
C65 C66 C661 C662 25.7(4) . . . . ?
C61 C66 C661 C662 -157.0(2) . . . . ?
C65 C66 C661 C663 -99.0(3) . . . . ?
C61 C66 C661 C663 78.3(3) . . . . ?
