#------------------------------------------------------------------------------
#$Date: 2020-10-07 01:58:18 +0300 (Wed, 07 Oct 2020) $
#$Revision: 258202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038105.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_4038105
loop_
_publ_author_name
'Lazreg, Faïma'
'Vasseur, Marie'
'Slawin, Alexandra M. Z.'
'Cazin, Catherine S. J.'
_publ_section_title
;
 Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic
 carbene copper(I) catalysts
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              482
_journal_page_last               491
_journal_paper_doi               10.3762/bjoc.16.43
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C50 H66 B Cu F4 N6'
_chemical_formula_sum            'C50 H66 B Cu F4 N6'
_chemical_formula_weight         901.46
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-16
_audit_creation_method           'by CrystalStructure 4.1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.439(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.580(6)
_cell_length_b                   21.854(10)
_cell_length_c                   15.012(7)
_cell_measurement_reflns_used    11502
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.65
_cell_volume                     4769(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 29.257
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.434
_diffrn_reflns_theta_min         1.649
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1912.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.52
_refine_diff_density_min         -1.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     559
_refine_ls_number_reflns         8762
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0939
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1453P)²+17.2690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2495
_refine_ls_wR_factor_ref         0.2634
_reflns_number_gt                7559
_reflns_number_total             8762
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            1860-5397-16-43-S4.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 4038105--4038107.cif.'
_cod_database_code               4038105
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +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 0.22369(4) 0.12869(3) 0.24036(4) 0.0317(2) Uani 1 1 d . . . . .
F1 F 0.0476(3) -0.06797(16) 0.3330(2) 0.0531(9) Uani 1 1 d . . . . .
F2 F 0.0508(2) -0.16991(15) 0.3028(2) 0.0476(8) Uani 1 1 d . . . . .
F3 F 0.0293(2) -0.10176(15) 0.1896(2) 0.0449(8) Uani 1 1 d . . . . .
F4 F -0.0827(2) -0.11744(17) 0.2845(3) 0.0554(9) Uani 1 1 d . . . . .
N3 N 0.1525(3) 0.19890(18) -0.0068(3) 0.0303(9) Uani 1 1 d . . . . .
N4 N 0.2349(3) 0.22363(19) 0.0027(3) 0.0331(10) Uani 1 1 d . . . . .
N5 N 0.2686(3) 0.20228(18) 0.0824(3) 0.0289(9) Uani 1 1 d . . . . .
N33 N 0.1780(3) 0.03635(18) 0.4700(3) 0.0304(9) Uani 1 1 d . . . . .
N34 N 0.2594(3) 0.01320(18) 0.4557(3) 0.0306(9) Uani 1 1 d . . . . .
N35 N 0.2821(3) 0.04478(18) 0.3846(3) 0.0318(9) Uani 1 1 d . . . . .
C1 C 0.2105(4) 0.1650(2) 0.1252(4) 0.0331(11) Uani 1 1 d . . . . .
C2 C 0.1335(3) 0.1632(2) 0.0639(4) 0.0316(11) Uani 1 1 d . . . . .
C6 C 0.0471(4) 0.1293(2) 0.0717(3) 0.0325(11) Uani 1 1 d . . . . .
C7 C 0.0515(4) 0.0687(2) 0.1020(3) 0.0323(11) Uani 1 1 d . . . . .
H7 H 0.1097 0.0494 0.1127 0.039 Uiso 1 1 calc R U . . .
C8 C -0.0270(4) 0.0368(2) 0.1165(3) 0.0337(11) Uani 1 1 d . . . . .
H8 H -0.0221 -0.0044 0.1364 0.040 Uiso 1 1 calc R U . . .
C9 C -0.1141(4) 0.0636(2) 0.1025(3) 0.0319(11) Uani 1 1 d . . . . .
C10 C -0.1176(4) 0.1238(2) 0.0702(4) 0.0337(11) Uani 1 1 d . . . . .
H10 H -0.1757 0.1429 0.0580 0.040 Uiso 1 1 calc R U . . .
C11 C -0.0387(4) 0.1559(2) 0.0558(4) 0.0360(12) Uani 1 1 d . . . . .
H11 H -0.0433 0.1968 0.0345 0.043 Uiso 1 1 calc R U . . .
C12 C -0.1998(4) 0.0273(2) 0.1239(4) 0.0334(11) Uani 1 1 d . . . . .
C13 C -0.1930(4) 0.0148(2) 0.2254(4) 0.0376(12) Uani 1 1 d . . . . .
H13A H -0.1903 0.0537 0.2578 0.045 Uiso 1 1 calc R U . . .
H13B H -0.2471 -0.0084 0.2408 0.045 Uiso 1 1 calc R U . . .
H13C H -0.1373 -0.0090 0.2420 0.045 Uiso 1 1 calc R U . . .
C14 C -0.2890(4) 0.0620(3) 0.0993(4) 0.0387(12) Uani 1 1 d . . . . .
H14A H -0.2875 0.1014 0.1308 0.046 Uiso 1 1 calc R U . . .
H14B H -0.2955 0.0692 0.0347 0.046 Uiso 1 1 calc R U . . .
H14C H -0.3413 0.0378 0.1167 0.046 Uiso 1 1 calc R U . . .
C15 C -0.2039(4) -0.0335(2) 0.0742(4) 0.0373(12) Uani 1 1 d . . . . .
H15A H -0.1470 -0.0565 0.0892 0.045 Uiso 1 1 calc R U . . .
H15B H -0.2566 -0.0573 0.0917 0.045 Uiso 1 1 calc R U . . .
H15C H -0.2107 -0.0259 0.0097 0.045 Uiso 1 1 calc R U . . .
C16 C 0.0959(4) 0.2112(2) -0.0902(3) 0.0343(11) Uani 1 1 d . . . . .
H16A H 0.0366 0.1903 -0.0887 0.041 Uiso 1 1 calc R U . . .
H16B H 0.0856 0.2554 -0.0964 0.041 Uiso 1 1 calc R U . . .
H16C H 0.1278 0.1963 -0.1410 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3607(3) 0.2194(2) 0.1135(3) 0.0315(11) Uani 1 1 d . . . . .
C18 C 0.4331(4) 0.1834(2) 0.0887(3) 0.0332(11) Uani 1 1 d . . . . .
C19 C 0.5210(4) 0.1997(2) 0.1209(4) 0.0371(12) Uani 1 1 d . . . . .
H19 H 0.5720 0.1764 0.1043 0.045 Uiso 1 1 calc R U . . .
C20 C 0.5353(4) 0.2496(2) 0.1773(4) 0.0394(13) Uani 1 1 d . . . . .
H20 H 0.5959 0.2595 0.2007 0.047 Uiso 1 1 calc R U . . .
C21 C 0.4622(4) 0.2850(2) 0.1996(4) 0.0368(12) Uani 1 1 d . . . . .
H21 H 0.4733 0.3198 0.2369 0.044 Uiso 1 1 calc R U . . .
C22 C 0.3730(4) 0.2707(2) 0.1686(3) 0.0337(11) Uani 1 1 d . . . . .
C23 C 0.4170(4) 0.1275(2) 0.0297(4) 0.0365(12) Uani 1 1 d . . . . .
H23 H 0.3540 0.1309 -0.0012 0.044 Uiso 1 1 calc R U . . .
C24 C 0.4855(4) 0.1224(3) -0.0425(4) 0.0452(14) Uani 1 1 d . . . . .
H24A H 0.4720 0.0856 -0.0784 0.054 Uiso 1 1 calc R U . . .
H24B H 0.4803 0.1586 -0.0811 0.054 Uiso 1 1 calc R U . . .
H24C H 0.5482 0.1197 -0.0140 0.054 Uiso 1 1 calc R U . . .
C25 C 0.4192(4) 0.0698(2) 0.0873(4) 0.0430(13) Uani 1 1 d . . . . .
H25A H 0.4088 0.0338 0.0488 0.052 Uiso 1 1 calc R U . . .
H25B H 0.4794 0.0664 0.1209 0.052 Uiso 1 1 calc R U . . .
H25C H 0.3709 0.0722 0.1290 0.052 Uiso 1 1 calc R U . . .
C26 C 0.2915(4) 0.3109(2) 0.1896(3) 0.0338(11) Uani 1 1 d . . . . .
H26 H 0.2348 0.2851 0.1830 0.041 Uiso 1 1 calc R U . . .
C27 C 0.2798(4) 0.3631(2) 0.1222(4) 0.0403(13) Uani 1 1 d . . . . .
H27A H 0.2276 0.3886 0.1361 0.048 Uiso 1 1 calc R U . . .
H27B H 0.3359 0.3880 0.1253 0.048 Uiso 1 1 calc R U . . .
H27C H 0.2685 0.3462 0.0619 0.048 Uiso 1 1 calc R U . . .
C28 C 0.3001(4) 0.3365(2) 0.2854(4) 0.0395(12) Uani 1 1 d . . . . .
H28A H 0.3076 0.3026 0.3281 0.047 Uiso 1 1 calc R U . . .
H28B H 0.3538 0.3636 0.2929 0.047 Uiso 1 1 calc R U . . .
H28C H 0.2445 0.3596 0.2962 0.047 Uiso 1 1 calc R U . . .
C31 C 0.2187(4) 0.0864(2) 0.3508(3) 0.0305(11) Uani 1 1 d . . . . .
C32 C 0.1506(3) 0.0808(2) 0.4102(3) 0.0305(11) Uani 1 1 d . . . . .
C36 C 0.0617(4) 0.1130(2) 0.4099(3) 0.0318(11) Uani 1 1 d . . . . .
C37 C 0.0133(4) 0.1264(2) 0.3284(3) 0.0329(11) Uani 1 1 d . . . . .
H37 H 0.0372 0.1137 0.2743 0.040 Uiso 1 1 calc R U . . .
C38 C -0.0686(4) 0.1576(2) 0.3258(4) 0.0342(11) Uani 1 1 d . . . . .
H38 H -0.0994 0.1671 0.2694 0.041 Uiso 1 1 calc R U . . .
C39 C -0.1080(3) 0.1760(2) 0.4034(4) 0.0319(11) Uani 1 1 d . . . . .
C40 C -0.0584(4) 0.1642(2) 0.4843(4) 0.0323(11) Uani 1 1 d . . . . .
H40 H -0.0826 0.1769 0.5383 0.039 Uiso 1 1 calc R U . . .
C41 C 0.0261(4) 0.1341(2) 0.4878(4) 0.0345(12) Uani 1 1 d . . . . .
H41 H 0.0597 0.1279 0.5439 0.041 Uiso 1 1 calc R U . . .
C42 C -0.2008(4) 0.2082(2) 0.3964(4) 0.0340(11) Uani 1 1 d . . . . .
C43 C -0.1928(4) 0.2689(3) 0.3474(4) 0.0465(14) Uani 1 1 d . . . . .
H43A H -0.2525 0.2896 0.3429 0.056 Uiso 1 1 calc R U . . .
H43B H -0.1471 0.2949 0.3805 0.056 Uiso 1 1 calc R U . . .
H43C H -0.1734 0.2612 0.2873 0.056 Uiso 1 1 calc R U . . .
C44 C -0.2724(4) 0.1680(3) 0.3453(4) 0.0472(15) Uani 1 1 d . . . . .
H44A H -0.3320 0.1889 0.3410 0.057 Uiso 1 1 calc R U . . .
H44B H -0.2534 0.1601 0.2852 0.057 Uiso 1 1 calc R U . . .
H44C H -0.2778 0.1291 0.3770 0.057 Uiso 1 1 calc R U . . .
C45 C -0.2356(4) 0.2209(3) 0.4886(4) 0.0404(13) Uani 1 1 d . . . . .
H45A H -0.2954 0.2416 0.4812 0.048 Uiso 1 1 calc R U . . .
H45B H -0.2423 0.1821 0.5203 0.048 Uiso 1 1 calc R U . . .
H45C H -0.1914 0.2470 0.5233 0.048 Uiso 1 1 calc R U . . .
C46 C 0.1268(4) 0.0057(2) 0.5392(4) 0.0351(12) Uani 1 1 d . . . . .
H46A H 0.0679 0.0265 0.5441 0.042 Uiso 1 1 calc R U . . .
H46B H 0.1156 -0.0371 0.5223 0.042 Uiso 1 1 calc R U . . .
H46C H 0.1632 0.0074 0.5968 0.042 Uiso 1 1 calc R U . . .
C47 C 0.3671(3) 0.0273(2) 0.3471(3) 0.0297(11) Uani 1 1 d . . . . .
C48 C 0.4481(4) 0.0591(2) 0.3741(3) 0.0322(11) Uani 1 1 d . . . . .
C49 C 0.5278(4) 0.0396(2) 0.3377(4) 0.0382(12) Uani 1 1 d . . . . .
H49 H 0.5839 0.0606 0.3530 0.046 Uiso 1 1 calc R U . . .
C50 C 0.5272(4) -0.0096(2) 0.2795(3) 0.0360(12) Uani 1 1 d . . . . .
H50 H 0.5829 -0.0228 0.2567 0.043 Uiso 1 1 calc R U . . .
C51 C 0.4457(4) -0.0396(2) 0.2546(4) 0.0369(12) Uani 1 1 d . . . . .
H51 H 0.4462 -0.0732 0.2144 0.044 Uiso 1 1 calc R U . . .
C52 C 0.3629(4) -0.0215(2) 0.2871(3) 0.0324(11) Uani 1 1 d . . . . .
C53 C 0.4469(4) 0.1129(2) 0.4375(4) 0.0385(12) Uani 1 1 d . . . . .
H53 H 0.3889 0.1102 0.4688 0.046 Uiso 1 1 calc R U . . .
C54 C 0.4442(4) 0.1733(2) 0.3859(4) 0.0469(14) Uani 1 1 d . . . . .
H54A H 0.4434 0.2075 0.4279 0.056 Uiso 1 1 calc R U . . .
H54B H 0.4987 0.1763 0.3518 0.056 Uiso 1 1 calc R U . . .
H54C H 0.3887 0.1746 0.3447 0.056 Uiso 1 1 calc R U . . .
C55 C 0.5278(4) 0.1109(3) 0.5091(4) 0.0453(14) Uani 1 1 d . . . . .
H55A H 0.5247 0.1464 0.5487 0.054 Uiso 1 1 calc R U . . .
H55B H 0.5247 0.0732 0.5441 0.054 Uiso 1 1 calc R U . . .
H55C H 0.5859 0.1119 0.4803 0.054 Uiso 1 1 calc R U . . .
C56 C 0.2746(4) -0.0555(2) 0.2622(3) 0.0339(11) Uani 1 1 d . . . . .
H56 H 0.2227 -0.0299 0.2809 0.041 Uiso 1 1 calc R U . . .
C57 C 0.2590(4) -0.0660(3) 0.1614(4) 0.0431(13) Uani 1 1 d . . . . .
H57A H 0.2011 -0.0882 0.1483 0.052 Uiso 1 1 calc R U . . .
H57B H 0.2559 -0.0265 0.1306 0.052 Uiso 1 1 calc R U . . .
H57C H 0.3100 -0.0901 0.1409 0.052 Uiso 1 1 calc R U . . .
C58 C 0.2740(4) -0.1154(3) 0.3140(4) 0.0447(14) Uani 1 1 d . . . . .
H58A H 0.2166 -0.1374 0.2977 0.054 Uiso 1 1 calc R U . . .
H58B H 0.3264 -0.1406 0.2994 0.054 Uiso 1 1 calc R U . . .
H58C H 0.2786 -0.1067 0.3782 0.054 Uiso 1 1 calc R U . . .
B1 B 0.0111(5) -0.1139(3) 0.2775(4) 0.0389(14) 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(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
C31 Cu1 C1 171.0(2) . . ?
N4 N3 C2 112.9(4) . . ?
N4 N3 C16 117.7(4) . . ?
C2 N3 C16 129.3(4) . . ?
N3 N4 N5 102.8(4) . . ?
N4 N5 C1 115.3(4) . . ?
N4 N5 C17 117.9(4) . . ?
C1 N5 C17 126.8(4) . . ?
N34 N33 C32 112.8(4) . . ?
N34 N33 C46 116.5(4) . . ?
C32 N33 C46 130.2(4) . . ?
N33 N34 N35 102.3(4) . . ?
N34 N35 C31 116.0(4) . . ?
N34 N35 C47 116.5(4) . . ?
C31 N35 C47 127.2(4) . . ?
N5 C1 C2 101.7(4) . . ?
N5 C1 Cu1 130.7(4) . . ?
C2 C1 Cu1 127.5(4) . . ?
N3 C2 C1 107.2(4) . . ?
N3 C2 C6 125.1(5) . . ?
C1 C2 C6 127.7(5) . . ?
C11 C6 C7 118.1(5) . . ?
C11 C6 C2 122.9(4) . . ?
C7 C6 C2 118.9(5) . . ?
C8 C7 C6 121.0(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.4(5) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 117.0(5) . . ?
C8 C9 C12 119.7(4) . . ?
C10 C9 C12 123.3(5) . . ?
C11 C10 C9 121.5(5) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C6 120.9(5) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C15 C12 C14 108.4(4) . . ?
C15 C12 C9 110.6(4) . . ?
C14 C12 C9 112.6(4) . . ?
C15 C12 C13 109.0(4) . . ?
C14 C12 C13 108.3(4) . . ?
C9 C12 C13 107.8(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 123.2(5) . . ?
C18 C17 N5 118.4(4) . . ?
C22 C17 N5 118.3(4) . . ?
C19 C18 C17 117.7(5) . . ?
C19 C18 C23 120.6(5) . . ?
C17 C18 C23 121.7(5) . . ?
C18 C19 C20 120.5(5) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.1(5) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C17 C22 C21 117.1(5) . . ?
C17 C22 C26 121.2(5) . . ?
C21 C22 C26 121.7(5) . . ?
C18 C23 C25 109.8(5) . . ?
C18 C23 C24 113.0(5) . . ?
C25 C23 C24 110.7(5) . . ?
C18 C23 H23 107.7 . . ?
C25 C23 H23 107.7 . . ?
C24 C23 H23 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C22 110.0(4) . . ?
C27 C26 C28 110.2(4) . . ?
C22 C26 C28 113.2(4) . . ?
C27 C26 H26 107.8 . . ?
C22 C26 H26 107.8 . . ?
C28 C26 H26 107.8 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N35 C31 C32 101.5(4) . . ?
N35 C31 Cu1 125.2(4) . . ?
C32 C31 Cu1 132.7(4) . . ?
N33 C32 C31 107.3(4) . . ?
N33 C32 C36 123.8(5) . . ?
C31 C32 C36 128.9(5) . . ?
C41 C36 C37 118.1(5) . . ?
C41 C36 C32 122.7(5) . . ?
C37 C36 C32 119.2(5) . . ?
C38 C37 C36 120.6(5) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C39 122.1(5) . . ?
C37 C38 H38 118.9 . . ?
C39 C38 H38 118.9 . . ?
C38 C39 C40 117.1(5) . . ?
C38 C39 C42 119.8(5) . . ?
C40 C39 C42 123.1(5) . . ?
C39 C40 C41 121.3(5) . . ?
C39 C40 H40 119.3 . . ?
C41 C40 H40 119.3 . . ?
C36 C41 C40 120.7(5) . . ?
C36 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C39 C42 C44 109.8(4) . . ?
C39 C42 C43 109.5(4) . . ?
C44 C42 C43 109.5(5) . . ?
C39 C42 C45 112.1(4) . . ?
C44 C42 C45 107.2(5) . . ?
C43 C42 C45 108.7(4) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N33 C46 H46A 109.5 . . ?
N33 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
N33 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C52 C47 C48 124.1(5) . . ?
C52 C47 N35 117.1(4) . . ?
C48 C47 N35 118.8(4) . . ?
C49 C48 C47 116.5(5) . . ?
C49 C48 C53 122.4(5) . . ?
C47 C48 C53 121.1(5) . . ?
C48 C49 C50 121.4(5) . . ?
C48 C49 H49 119.3 . . ?
C50 C49 H49 119.3 . . ?
C51 C50 C49 120.1(5) . . ?
C51 C50 H50 119.9 . . ?
C49 C50 H50 119.9 . . ?
C50 C51 C52 121.3(5) . . ?
C50 C51 H51 119.3 . . ?
C52 C51 H51 119.3 . . ?
C47 C52 C51 116.5(5) . . ?
C47 C52 C56 122.1(5) . . ?
C51 C52 C56 121.3(5) . . ?
C48 C53 C55 111.9(5) . . ?
C48 C53 C54 110.7(5) . . ?
C55 C53 C54 111.6(5) . . ?
C48 C53 H53 107.5 . . ?
C55 C53 H53 107.5 . . ?
C54 C53 H53 107.5 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C53 C55 H55A 109.5 . . ?
C53 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C53 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C52 C56 C57 112.2(4) . . ?
C52 C56 C58 109.6(4) . . ?
C57 C56 C58 111.7(5) . . ?
C52 C56 H56 107.7 . . ?
C57 C56 H56 107.7 . . ?
C58 C56 H56 107.7 . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C56 C58 H58A 109.5 . . ?
C56 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C56 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
F3 B1 F2 108.6(5) . . ?
F3 B1 F4 110.2(5) . . ?
F2 B1 F4 108.8(5) . . ?
F3 B1 F1 109.9(5) . . ?
F2 B1 F1 109.9(5) . . ?
F4 B1 F1 109.4(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 C31 1.905(5) . ?
Cu1 C1 1.898(5) . ?
F1 B1 1.384(7) . ?
F2 B1 1.395(7) . ?
F3 B1 1.392(7) . ?
F4 B1 1.382(8) . ?
N3 N4 1.316(6) . ?
N3 C2 1.364(6) . ?
N3 C16 1.469(6) . ?
N4 N5 1.342(6) . ?
N5 C1 1.371(6) . ?
N5 C17 1.437(6) . ?
N33 N34 1.322(6) . ?
N33 C32 1.361(6) . ?
N33 C46 1.485(6) . ?
N34 N35 1.334(6) . ?
N35 C31 1.366(6) . ?
N35 C47 1.452(6) . ?
C1 C2 1.395(7) . ?
C2 C6 1.474(7) . ?
C6 C11 1.383(8) . ?
C6 C7 1.400(7) . ?
C7 C8 1.371(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(7) . ?
C9 C12 1.535(7) . ?
C10 C11 1.379(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C15 1.522(7) . ?
C12 C14 1.527(7) . ?
C12 C13 1.544(7) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.389(7) . ?
C17 C22 1.397(7) . ?
C18 C19 1.380(7) . ?
C18 C23 1.519(7) . ?
C19 C20 1.388(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(7) . ?
C21 H21 0.9500 . ?
C22 C26 1.530(7) . ?
C23 C25 1.527(7) . ?
C23 C24 1.533(8) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.525(7) . ?
C26 C28 1.539(7) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C31 C32 1.390(7) . ?
C32 C36 1.474(7) . ?
C36 C41 1.395(7) . ?
C36 C37 1.395(7) . ?
C37 C38 1.374(7) . ?
C37 H37 0.9500 . ?
C38 C39 1.398(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.390(7) . ?
C39 C42 1.521(7) . ?
C40 C41 1.394(7) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 C44 1.525(7) . ?
C42 C43 1.526(7) . ?
C42 C45 1.537(8) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C52 1.394(7) . ?
C47 C48 1.403(7) . ?
C48 C49 1.388(8) . ?
C48 C53 1.514(7) . ?
C49 C50 1.386(8) . ?
C49 H49 0.9500 . ?
C50 C51 1.383(8) . ?
C50 H50 0.9500 . ?
C51 C52 1.395(7) . ?
C51 H51 0.9500 . ?
C52 C56 1.508(7) . ?
C53 C55 1.534(8) . ?
C53 C54 1.529(8) . ?
C53 H53 1.0000 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 C57 1.529(7) . ?
C56 C58 1.522(7) . ?
C56 H56 1.0000 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 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 N3 N4 N5 0.1(5) . . . . ?
C16 N3 N4 N5 -178.1(4) . . . . ?
N3 N4 N5 C1 -0.5(5) . . . . ?
N3 N4 N5 C17 178.4(4) . . . . ?
C32 N33 N34 N35 -0.1(5) . . . . ?
C46 N33 N34 N35 172.8(4) . . . . ?
N33 N34 N35 C31 -1.3(5) . . . . ?
N33 N34 N35 C47 -175.9(4) . . . . ?
N4 N5 C1 C2 0.6(5) . . . . ?
C17 N5 C1 C2 -178.2(4) . . . . ?
N4 N5 C1 Cu1 -175.4(4) . . . . ?
C17 N5 C1 Cu1 5.8(8) . . . . ?
N4 N3 C2 C1 0.2(6) . . . . ?
C16 N3 C2 C1 178.2(5) . . . . ?
N4 N3 C2 C6 -179.5(4) . . . . ?
C16 N3 C2 C6 -1.5(8) . . . . ?
N5 C1 C2 N3 -0.5(5) . . . . ?
Cu1 C1 C2 N3 175.8(4) . . . . ?
N5 C1 C2 C6 179.2(5) . . . . ?
Cu1 C1 C2 C6 -4.5(8) . . . . ?
N3 C2 C6 C11 -48.8(8) . . . . ?
C1 C2 C6 C11 131.5(6) . . . . ?
N3 C2 C6 C7 135.4(5) . . . . ?
C1 C2 C6 C7 -44.3(8) . . . . ?
C11 C6 C7 C8 -0.7(8) . . . . ?
C2 C6 C7 C8 175.3(5) . . . . ?
C6 C7 C8 C9 -0.7(8) . . . . ?
C7 C8 C9 C10 2.2(7) . . . . ?
C7 C8 C9 C12 -177.1(5) . . . . ?
C8 C9 C10 C11 -2.2(8) . . . . ?
C12 C9 C10 C11 177.0(5) . . . . ?
C9 C10 C11 C6 0.8(8) . . . . ?
C7 C6 C11 C10 0.7(8) . . . . ?
C2 C6 C11 C10 -175.1(5) . . . . ?
C8 C9 C12 C15 -55.1(6) . . . . ?
C10 C9 C12 C15 125.7(5) . . . . ?
C8 C9 C12 C14 -176.5(5) . . . . ?
C10 C9 C12 C14 4.3(7) . . . . ?
C8 C9 C12 C13 64.1(6) . . . . ?
C10 C9 C12 C13 -115.1(5) . . . . ?
N4 N5 C17 C18 -87.7(6) . . . . ?
C1 N5 C17 C18 91.1(6) . . . . ?
N4 N5 C17 C22 93.6(6) . . . . ?
C1 N5 C17 C22 -87.7(6) . . . . ?
C22 C17 C18 C19 0.2(8) . . . . ?
N5 C17 C18 C19 -178.5(5) . . . . ?
C22 C17 C18 C23 179.2(5) . . . . ?
N5 C17 C18 C23 0.5(7) . . . . ?
C17 C18 C19 C20 1.1(8) . . . . ?
C23 C18 C19 C20 -177.8(5) . . . . ?
C18 C19 C20 C21 -2.2(8) . . . . ?
C19 C20 C21 C22 1.8(8) . . . . ?
C18 C17 C22 C21 -0.6(8) . . . . ?
N5 C17 C22 C21 178.1(4) . . . . ?
C18 C17 C22 C26 176.5(5) . . . . ?
N5 C17 C22 C26 -4.8(7) . . . . ?
C20 C21 C22 C17 -0.5(8) . . . . ?
C20 C21 C22 C26 -177.5(5) . . . . ?
C19 C18 C23 C25 80.3(6) . . . . ?
C17 C18 C23 C25 -98.6(6) . . . . ?
C19 C18 C23 C24 -43.9(7) . . . . ?
C17 C18 C23 C24 137.2(5) . . . . ?
C17 C22 C26 C27 -92.0(6) . . . . ?
C21 C22 C26 C27 85.0(6) . . . . ?
C17 C22 C26 C28 144.3(5) . . . . ?
C21 C22 C26 C28 -38.8(7) . . . . ?
N34 N35 C31 C32 2.1(6) . . . . ?
C47 N35 C31 C32 176.0(5) . . . . ?
N34 N35 C31 Cu1 -170.0(3) . . . . ?
C47 N35 C31 Cu1 3.9(7) . . . . ?
N34 N33 C32 C31 1.3(6) . . . . ?
C46 N33 C32 C31 -170.3(5) . . . . ?
N34 N33 C32 C36 178.5(4) . . . . ?
C46 N33 C32 C36 6.9(8) . . . . ?
N35 C31 C32 N33 -1.9(5) . . . . ?
Cu1 C31 C32 N33 169.3(4) . . . . ?
N35 C31 C32 C36 -178.9(5) . . . . ?
Cu1 C31 C32 C36 -7.7(8) . . . . ?
N33 C32 C36 C41 43.5(7) . . . . ?
C31 C32 C36 C41 -139.9(6) . . . . ?
N33 C32 C36 C37 -140.3(5) . . . . ?
C31 C32 C36 C37 36.2(8) . . . . ?
C41 C36 C37 C38 -2.1(7) . . . . ?
C32 C36 C37 C38 -178.4(5) . . . . ?
C36 C37 C38 C39 -1.6(8) . . . . ?
C37 C38 C39 C40 3.3(7) . . . . ?
C37 C38 C39 C42 -177.5(5) . . . . ?
C38 C39 C40 C41 -1.4(7) . . . . ?
C42 C39 C40 C41 179.4(5) . . . . ?
C37 C36 C41 C40 4.0(7) . . . . ?
C32 C36 C41 C40 -179.9(5) . . . . ?
C39 C40 C41 C36 -2.3(8) . . . . ?
C38 C39 C42 C44 57.1(6) . . . . ?
C40 C39 C42 C44 -123.7(5) . . . . ?
C38 C39 C42 C43 -63.2(6) . . . . ?
C40 C39 C42 C43 116.0(6) . . . . ?
C38 C39 C42 C45 176.1(5) . . . . ?
C40 C39 C42 C45 -4.7(7) . . . . ?
N34 N35 C47 C52 84.0(6) . . . . ?
C31 N35 C47 C52 -89.9(6) . . . . ?
N34 N35 C47 C48 -94.8(5) . . . . ?
C31 N35 C47 C48 91.3(6) . . . . ?
C52 C47 C48 C49 0.0(7) . . . . ?
N35 C47 C48 C49 178.7(4) . . . . ?
C52 C47 C48 C53 178.1(5) . . . . ?
N35 C47 C48 C53 -3.2(7) . . . . ?
C47 C48 C49 C50 -1.6(7) . . . . ?
C53 C48 C49 C50 -179.7(5) . . . . ?
C48 C49 C50 C51 1.8(8) . . . . ?
C49 C50 C51 C52 -0.2(8) . . . . ?
C48 C47 C52 C51 1.4(7) . . . . ?
N35 C47 C52 C51 -177.3(4) . . . . ?
C48 C47 C52 C56 178.1(5) . . . . ?
N35 C47 C52 C56 -0.6(7) . . . . ?
C50 C51 C52 C47 -1.3(7) . . . . ?
C50 C51 C52 C56 -178.0(5) . . . . ?
C49 C48 C53 C55 -45.0(7) . . . . ?
C47 C48 C53 C55 137.0(5) . . . . ?
C49 C48 C53 C54 80.1(6) . . . . ?
C47 C48 C53 C54 -97.9(6) . . . . ?
C47 C52 C56 C57 134.4(5) . . . . ?
C51 C52 C56 C57 -49.1(7) . . . . ?
C47 C52 C56 C58 -100.9(6) . . . . ?
C51 C52 C56 C58 75.7(6) . . . . ?
