#------------------------------------------------------------------------------
#$Date: 2020-02-20 01:36:14 +0200 (Thu, 20 Feb 2020) $
#$Revision: 248294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/42/4134202.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_4134202
loop_
_publ_author_name
'Shimomura, Keito'
'Kai, Hiroto'
'Nakamura, Yuma'
'Hong, Yongseok'
'Mori, Shigeki'
'Miki, Koji'
'Ohe, Kouichi'
'Notsuka, Yusuke'
'Yamaoka, Yoshihisa'
'Ishida, Masatoshi'
'Kim, Dongho'
'Furuta, Hiroyuki'
_publ_section_title
;
 Bis-Metal Complexes of Doubly N-Confused Dioxohexaphyrins as Potential
 Near Infrared-II Photoacoustic Dyes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13475
_journal_year                    2020
_chemical_formula_moiety         'C66 H10 Cu2 F30 N6 O2, 2(C H2 Cl2)'
_chemical_formula_sum            'C68 H14 Cl4 Cu2 F30 N6 O2'
_chemical_formula_weight         1785.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.891(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4761(5)
_cell_length_b                   25.9270(9)
_cell_length_c                   25.4632(9)
_cell_measurement_reflns_used    13762
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.14
_cell_measurement_theta_min      2.24
_cell_volume                     6196.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_publication_material  'CrystalStructure 4.2.1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            50539
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.615
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_exptl_absorpt_coefficient_mu    1.006
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3504
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.880
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     668
_refine_ls_number_reflns         7114
_refine_ls_number_restraints     840
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0700P)²+90.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2325
_refine_ls_wR_factor_ref         0.2485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5177
_reflns_number_total             7114
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b13475_si_004.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4134202
_shelx_shelxl_version_number     2014/7
_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   0.864
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.2500 0.73584(4) 0.0000 0.0326(3) Uani 1 2 d S T P . .
Cu2 Cu 0.2500 0.55929(4) 0.0000 0.0352(3) Uani 1 2 d S T P . .
F16 F 0.4551(5) 0.36784(17) 0.06326(18) 0.0562(13) Uani 1 1 d . . . . .
F17 F 0.4599(6) 0.26358(18) 0.0615(2) 0.0671(15) Uani 1 1 d . . . . .
F18 F 0.2500 0.2114(2) 0.0000 0.071(2) Uani 1 2 d S T P . .
O1 O 0.3852(5) 0.68035(17) 0.02006(18) 0.0390(11) Uani 1 1 d . . . . .
N1 N 0.3295(6) 0.7850(2) 0.0518(2) 0.0347(13) Uani 1 1 d . . . . .
N2 N 0.2911(7) 0.6100(2) 0.0604(2) 0.0416(14) Uani 1 1 d . . . . .
N3 N 0.2124(7) 0.5053(2) 0.0514(2) 0.0389(13) Uani 1 1 d . . . . .
C1 C 0.3322(8) 0.8366(3) 0.0422(3) 0.0389(16) Uani 1 1 d . . . . .
C2 C 0.4264(9) 0.8616(3) 0.0849(3) 0.0470(19) Uani 1 1 d . . . . .
H2 H 0.4492 0.8973 0.0874 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4746(8) 0.8250(3) 0.1198(3) 0.0427(17) Uani 1 1 d . . . . .
H3 H 0.5391 0.8301 0.1514 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4113(8) 0.7764(3) 0.1011(2) 0.0369(15) Uani 1 1 d . . . . .
C5 C 0.4146(7) 0.7312(2) 0.1296(2) 0.0351(15) Uani 1 1 d . . . . .
C6 C 0.3548(8) 0.6825(2) 0.1133(2) 0.0386(16) Uani 1 1 d . . . . .
C7 C 0.3458(8) 0.6583(2) 0.0599(3) 0.0395(17) Uani 1 1 d . . . . .
C8 C 0.3047(8) 0.6455(3) 0.1447(3) 0.0395(16) Uani 1 1 d . . . . .
H8 H 0.2998 0.6484 0.1816 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2615(9) 0.6020(3) 0.1122(3) 0.0423(17) Uani 1 1 d . . . . .
C10 C 0.1992(9) 0.5592(3) 0.1302(3) 0.0431(17) Uani 1 1 d D . . . .
C11 C 0.1730(9) 0.5125(3) 0.1006(3) 0.0423(17) Uani 1 1 d . . . . .
C12 C 0.1262(10) 0.4655(3) 0.1213(3) 0.052(2) Uani 1 1 d . . . . .
H12 H 0.0908 0.4608 0.1541 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1424(10) 0.4286(3) 0.0844(3) 0.0485(19) Uani 1 1 d . . . . .
H13 H 0.1198 0.3931 0.0866 0.058 Uiso 1 1 calc R U . . .
C14 C 0.1988(8) 0.4529(2) 0.0425(3) 0.0381(16) Uani 1 1 d . . . . .
C15 C 0.2500 0.8617(3) 0.0000 0.042(2) Uani 1 2 d S T P . .
C16 C 0.274(3) 0.9197(5) -0.0027(11) 0.049(6) Uani 0.5 1 d . U P A -1
C17 C 0.357(3) 0.9417(11) -0.0367(10) 0.064(6) Uani 0.5 1 d . U P A -1
C18 C 0.372(2) 0.9945(7) -0.0408(7) 0.064(4) Uani 0.5 1 d . U P A -1
C19 C 0.301(3) 1.0260(7) -0.0084(9) 0.071(5) Uani 0.5 1 d . U P A -1
C20 C 0.220(3) 1.0063(8) 0.0232(9) 0.071(5) Uani 0.5 1 d . U P A -1
C21 C 0.202(3) 0.9508(8) 0.0281(9) 0.064(6) Uani 0.5 1 d . U P A -1
F1 F 0.4232(18) 0.9117(5) -0.0682(5) 0.077(4) Uani 0.5 1 d . U P A -1
F2 F 0.453(2) 1.0131(5) -0.0752(5) 0.104(5) Uani 0.5 1 d . U P A -1
F3 F 0.3152(17) 1.0771(4) -0.0127(5) 0.098(5) Uani 0.5 1 d . U P A -1
F4 F 0.150(2) 1.0366(6) 0.0547(7) 0.127(6) Uani 0.5 1 d . U P A -1
F5 F 0.121(3) 0.9340(7) 0.0598(9) 0.111(8) Uani 0.5 1 d . U P A -1
C22 C 0.4809(8) 0.7326(3) 0.1866(3) 0.0382(16) Uani 1 1 d . . . . .
C23 C 0.4280(9) 0.7628(3) 0.2244(3) 0.0473(19) Uani 1 1 d . . . . .
C24 C 0.4891(10) 0.7627(3) 0.2775(3) 0.058(2) Uani 1 1 d . . . . .
C25 C 0.6032(12) 0.7303(4) 0.2929(3) 0.074(3) Uani 1 1 d . . . . .
C26 C 0.6548(10) 0.7002(4) 0.2567(3) 0.067(3) Uani 1 1 d . . . . .
C27 C 0.5926(9) 0.7006(3) 0.2045(3) 0.051(2) Uani 1 1 d . . . . .
F6 F 0.3164(5) 0.79374(17) 0.21174(18) 0.0516(11) Uani 1 1 d . . . . .
F7 F 0.4392(7) 0.7923(2) 0.31279(19) 0.0778(18) Uani 1 1 d . . . . .
F8 F 0.6707(8) 0.7315(3) 0.3432(2) 0.106(3) Uani 1 1 d . . . . .
F9 F 0.7693(7) 0.6698(3) 0.2715(2) 0.098(2) Uani 1 1 d . . . . .
F10 F 0.6520(5) 0.67068(18) 0.17003(18) 0.0589(14) Uani 1 1 d . . . . .
C28 C 0.191(2) 0.5579(13) 0.1887(5) 0.039(4) Uani 0.529(14) 1 d D U P B 2
C29 C 0.070(2) 0.5742(8) 0.2056(7) 0.049(4) Uani 0.529(14) 1 d . U P B 2
C30 C 0.049(2) 0.5708(8) 0.2584(8) 0.056(4) Uani 0.529(14) 1 d . U P B 2
C31 C 0.150(3) 0.5520(7) 0.2945(7) 0.039(3) Uani 0.529(14) 1 d . U P B 2
C32 C 0.278(2) 0.5374(7) 0.2792(6) 0.041(4) Uani 0.529(14) 1 d . U P B 2
C33 C 0.299(2) 0.5406(9) 0.2269(8) 0.042(4) Uani 0.529(14) 1 d . U P B 2
F11 F -0.0386(16) 0.5922(7) 0.1707(5) 0.081(5) Uani 0.529(14) 1 d . U P B 2
F12 F -0.0716(18) 0.5884(8) 0.2734(5) 0.102(6) Uani 0.529(14) 1 d . U P B 2
F13 F 0.1368(16) 0.5486(5) 0.3462(5) 0.057(3) Uani 0.529(14) 1 d . U P B 2
F14 F 0.3841(12) 0.5207(7) 0.3161(5) 0.077(4) Uani 0.529(14) 1 d . U P B 2
F15 F 0.4210(16) 0.5232(9) 0.2121(6) 0.089(5) Uani 0.529(14) 1 d . U P B 2
C28A C 0.150(3) 0.5593(17) 0.1839(6) 0.042(5) Uani 0.471(14) 1 d D U P B 3
C29A C 0.007(3) 0.5607(8) 0.1963(9) 0.052(4) Uani 0.471(14) 1 d . U P B 3
C30A C -0.025(3) 0.5599(8) 0.2455(10) 0.062(4) Uani 0.471(14) 1 d . U P B 3
C31A C 0.077(4) 0.5541(10) 0.2871(11) 0.065(5) Uani 0.471(14) 1 d . U P B 3
C32A C 0.217(4) 0.5505(9) 0.2816(10) 0.054(5) Uani 0.471(14) 1 d . U P B 3
C33A C 0.254(3) 0.5535(8) 0.2286(10) 0.043(4) Uani 0.471(14) 1 d . U P B 3
F11A F -0.0930(16) 0.5670(5) 0.1554(7) 0.065(4) Uani 0.471(14) 1 d . U P B 3
F12A F -0.158(2) 0.5618(5) 0.2544(7) 0.085(5) Uani 0.471(14) 1 d . U P B 3
F13A F 0.050(3) 0.5472(7) 0.3372(7) 0.098(6) Uani 0.471(14) 1 d . U P B 3
F14A F 0.315(3) 0.5437(7) 0.3197(5) 0.095(6) Uani 0.471(14) 1 d . U P B 3
F15A F 0.3952(19) 0.5490(5) 0.2214(5) 0.050(3) Uani 0.471(14) 1 d . U P B 3
C34 C 0.2500 0.4275(4) 0.0000 0.037(2) Uani 1 2 d S T P . .
C35 C 0.2500 0.3703(4) 0.0000 0.039(2) Uani 1 2 d S T P . .
C36 C 0.3533(8) 0.3427(3) 0.0320(3) 0.0407(17) Uani 1 1 d . . . . .
C37 C 0.3558(9) 0.2894(3) 0.0319(3) 0.0485(19) Uani 1 1 d . . . . .
C38 C 0.2500 0.2633(4) 0.0000 0.052(3) Uani 1 2 d S T P . .
Cl1 Cl 0.4266(5) 0.6576(2) 0.3582(2) 0.1151(18) Uani 0.791(7) 1 d D U P C 4
Cl2 Cl 0.6768(7) 0.5938(3) 0.3551(3) 0.168(2) Uani 0.791(7) 1 d D U P C 4
C39 C 0.5880(13) 0.6354(5) 0.3952(5) 0.169(3) Uani 0.791(7) 1 d D U P C 4
H39A H 0.6499 0.6652 0.4069 0.203 Uiso 0.791(7) 1 calc R U P C 4
H39B H 0.5670 0.6167 0.4271 0.203 Uiso 0.791(7) 1 calc R U P C 4
Cl1A Cl 0.597(3) 0.5873(13) 0.2882(8) 0.192(6) Uani 0.209(7) 1 d D U P C 5
Cl2A Cl 0.5880(13) 0.6354(5) 0.3952(5) 0.169(3) Uani 0.209(7) 1 d D U P C 5
C39A C 0.6768(7) 0.5938(3) 0.3551(3) 0.168(2) Uani 0.209(7) 1 d D U P C 5
H39C H 0.6833 0.5592 0.3717 0.202 Uiso 0.209(7) 1 calc R U P C 5
H39D H 0.7753 0.6066 0.3553 0.202 Uiso 0.209(7) 1 calc R U P C 5
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'
O O 0.0106 0.0060 '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'
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
N1 Cu1 N1 96.4(3) 2 . ?
N1 Cu1 O1 148.8(2) 2 . ?
N1 Cu1 O1 97.4(2) . . ?
N1 Cu1 O1 97.4(2) 2 2 ?
N1 Cu1 O1 148.8(2) . 2 ?
O1 Cu1 O1 84.8(3) . 2 ?
N3 Cu2 N3 90.2(3) . 2 ?
N3 Cu2 N2 158.3(3) . 2 ?
N3 Cu2 N2 89.5(2) 2 2 ?
N3 Cu2 N2 89.5(2) . . ?
N3 Cu2 N2 158.3(3) 2 . ?
N2 Cu2 N2 98.7(3) 2 . ?
C7 O1 Cu1 106.7(5) . . ?
C1 N1 C4 107.3(5) . . ?
C1 N1 Cu1 123.1(4) . . ?
C4 N1 Cu1 128.9(4) . . ?
C7 N2 C9 105.7(6) . . ?
C7 N2 Cu2 129.0(5) . . ?
C9 N2 Cu2 125.2(5) . . ?
C11 N3 C14 104.7(6) . . ?
C11 N3 Cu2 127.2(5) . . ?
C14 N3 Cu2 127.4(5) . . ?
N1 C1 C15 125.1(6) . . ?
N1 C1 C2 109.1(6) . . ?
C15 C1 C2 125.7(6) . . ?
C3 C2 C1 107.4(6) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
C2 C3 C4 108.1(6) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
C5 C4 N1 125.4(6) . . ?
C5 C4 C3 126.1(6) . . ?
N1 C4 C3 108.0(6) . . ?
C4 C5 C6 128.5(5) . . ?
C4 C5 C22 117.7(6) . . ?
C6 C5 C22 113.6(6) . . ?
C8 C6 C5 127.2(6) . . ?
C8 C6 C7 104.8(6) . . ?
C5 C6 C7 127.7(7) . . ?
O1 C7 N2 125.4(6) . . ?
O1 C7 C6 123.7(6) . . ?
N2 C7 C6 110.9(6) . . ?
C6 C8 C9 107.9(6) . . ?
C6 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
C10 C9 N2 126.1(6) . . ?
C10 C9 C8 123.4(7) . . ?
N2 C9 C8 110.5(6) . . ?
C9 C10 C11 124.2(7) . . ?
C9 C10 C28 115.8(14) . . ?
C11 C10 C28 118.4(14) . . ?
C9 C10 C28A 120.5(18) . . ?
C11 C10 C28A 115.3(18) . . ?
N3 C11 C12 111.1(6) . . ?
N3 C11 C10 123.3(7) . . ?
C12 C11 C10 124.7(7) . . ?
C13 C12 C11 106.0(7) . . ?
C13 C12 H12 127.0 . . ?
C11 C12 H12 127.0 . . ?
C12 C13 C14 107.4(6) . . ?
C12 C13 H13 126.3 . . ?
C14 C13 H13 126.3 . . ?
N3 C14 C13 110.6(6) . . ?
N3 C14 C34 123.6(7) . . ?
C13 C14 C34 125.5(6) . . ?
C1 C15 C1 124.4(8) . 2 ?
C1 C15 C16 115.0(11) . . ?
C1 C15 C16 119.8(11) 2 . ?
C17 C16 C21 119(2) . . ?
C17 C16 C15 123(2) . . ?
C21 C16 C15 118(2) . . ?
F1 C17 C16 120(2) . . ?
F1 C17 C18 118(2) . . ?
C16 C17 C18 122(3) . . ?
F2 C18 C17 119(2) . . ?
F2 C18 C19 123.0(17) . . ?
C17 C18 C19 118(2) . . ?
C20 C19 F3 120.9(19) . . ?
C20 C19 C18 120.8(17) . . ?
F3 C19 C18 118(2) . . ?
C19 C20 F4 121.3(18) . . ?
C19 C20 C21 122(2) . . ?
F4 C20 C21 117(2) . . ?
F5 C21 C16 124(2) . . ?
F5 C21 C20 119(2) . . ?
C16 C21 C20 118(2) . . ?
C27 C22 C23 116.6(6) . . ?
C27 C22 C5 120.5(6) . . ?
C23 C22 C5 122.8(6) . . ?
F6 C23 C22 121.6(6) . . ?
F6 C23 C24 116.4(7) . . ?
C22 C23 C24 122.0(7) . . ?
F7 C24 C25 119.9(7) . . ?
F7 C24 C23 121.3(8) . . ?
C25 C24 C23 118.8(7) . . ?
F8 C25 C26 119.5(8) . . ?
F8 C25 C24 120.4(8) . . ?
C26 C25 C24 119.9(7) . . ?
C25 C26 F9 119.9(7) . . ?
C25 C26 C27 120.6(7) . . ?
F9 C26 C27 119.5(8) . . ?
F10 C27 C22 120.2(6) . . ?
F10 C27 C26 117.5(7) . . ?
C22 C27 C26 122.1(7) . . ?
C29 C28 C33 117.2(15) . . ?
C29 C28 C10 118.3(16) . . ?
C33 C28 C10 124.5(17) . . ?
C28 C29 F11 120.2(16) . . ?
C28 C29 C30 122.1(16) . . ?
F11 C29 C30 117.6(18) . . ?
C31 C30 F12 120(2) . . ?
C31 C30 C29 120.6(18) . . ?
F12 C30 C29 119.8(18) . . ?
C30 C31 F13 123(2) . . ?
C30 C31 C32 119.0(18) . . ?
F13 C31 C32 117.8(15) . . ?
F14 C32 C33 120.3(17) . . ?
F14 C32 C31 119.3(15) . . ?
C33 C32 C31 120.5(17) . . ?
F15 C33 C32 119.7(17) . . ?
F15 C33 C28 119.7(18) . . ?
C32 C33 C28 120.5(19) . . ?
C33A C28A C29A 113.9(17) . . ?
C33A C28A C10 117.6(19) . . ?
C29A C28A C10 128.4(19) . . ?
F11A C29A C30A 121(2) . . ?
F11A C29A C28A 115.4(19) . . ?
C30A C29A C28A 123(2) . . ?
F12A C30A C29A 121(3) . . ?
F12A C30A C31A 118(2) . . ?
C29A C30A C31A 121(3) . . ?
C30A C31A F13A 124(3) . . ?
C30A C31A C32A 122(2) . . ?
F13A C31A C32A 114(3) . . ?
F14A C32A C31A 124(3) . . ?
F14A C32A C33A 119(3) . . ?
C31A C32A C33A 118(2) . . ?
F15A C33A C28A 119(2) . . ?
F15A C33A C32A 119(2) . . ?
C28A C33A C32A 122(2) . . ?
C14 C34 C14 124.2(9) 2 . ?
C14 C34 C35 117.9(4) 2 . ?
C14 C34 C35 117.9(4) . . ?
C36 C35 C36 117.6(9) . 2 ?
C36 C35 C34 121.2(4) . . ?
C36 C35 C34 121.2(4) 2 . ?
F16 C36 C37 118.7(6) . . ?
F16 C36 C35 119.5(6) . . ?
C37 C36 C35 121.8(7) . . ?
F17 C37 C38 120.5(7) . . ?
F17 C37 C36 120.7(7) . . ?
C38 C37 C36 118.8(7) . . ?
F18 C38 C37 119.4(5) . . ?
F18 C38 C37 119.4(5) . 2 ?
C37 C38 C37 121.1(9) . 2 ?
Cl2 C39 Cl1 109.5(7) . . ?
Cl2 C39 H39A 109.8 . . ?
Cl1 C39 H39A 109.8 . . ?
Cl2 C39 H39B 109.8 . . ?
Cl1 C39 H39B 109.8 . . ?
H39A C39 H39B 108.2 . . ?
Cl2A C39A Cl1A 115.8(11) . . ?
Cl2A C39A H39C 108.3 . . ?
Cl1A C39A H39C 108.3 . . ?
Cl2A C39A H39D 108.3 . . ?
Cl1A C39A H39D 108.3 . . ?
H39C C39A H39D 107.4 . . ?
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 N1 1.914(5) 2 ?
Cu1 N1 1.914(5) . ?
Cu1 O1 1.948(5) . ?
Cu1 O1 1.948(5) 2 ?
Cu2 N3 1.982(6) . ?
Cu2 N3 1.982(6) 2 ?
Cu2 N2 2.020(6) 2 ?
Cu2 N2 2.020(6) . ?
F16 C36 1.334(8) . ?
F17 C37 1.336(9) . ?
F18 C38 1.344(12) . ?
O1 C7 1.266(9) . ?
N1 C1 1.360(8) . ?
N1 C4 1.399(8) . ?
N2 C7 1.355(9) . ?
N2 C9 1.402(9) . ?
N3 C11 1.366(9) . ?
N3 C14 1.380(8) . ?
C1 C15 1.399(8) . ?
C1 C2 1.461(9) . ?
C2 C3 1.337(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.450(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(9) . ?
C5 C6 1.422(9) . ?
C5 C22 1.502(8) . ?
C6 C8 1.375(10) . ?
C6 C7 1.487(9) . ?
C8 C9 1.425(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.365(10) . ?
C10 C11 1.431(9) . ?
C10 C28 1.502(15) . ?
C10 C28A 1.504(16) . ?
C11 C12 1.423(10) . ?
C12 C13 1.363(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.407(10) . ?
C13 H13 0.9500 . ?
C14 C34 1.408(8) . ?
C15 C1 1.399(8) 2 ?
C15 C16 1.524(16) . ?
C16 C17 1.37(4) . ?
C16 C21 1.37(3) . ?
C17 F1 1.33(3) . ?
C17 C18 1.38(3) . ?
C18 F2 1.33(3) . ?
C18 C19 1.39(3) . ?
C19 C20 1.30(3) . ?
C19 F3 1.34(2) . ?
C20 F4 1.36(3) . ?
C20 C21 1.45(3) . ?
C21 F5 1.27(3) . ?
C22 C27 1.372(9) . ?
C22 C23 1.386(10) . ?
C23 F6 1.331(8) . ?
C23 C24 1.396(10) . ?
C24 F7 1.319(9) . ?
C24 C25 1.382(12) . ?
C25 F8 1.350(8) . ?
C25 C26 1.350(13) . ?
C26 F9 1.352(9) . ?
C26 C27 1.378(10) . ?
C27 F10 1.350(9) . ?
C28 C29 1.35(3) . ?
C28 C33 1.39(3) . ?
C29 F11 1.346(19) . ?
C29 C30 1.39(3) . ?
C30 C31 1.33(3) . ?
C30 F12 1.33(2) . ?
C31 F13 1.34(2) . ?
C31 C32 1.38(3) . ?
C32 F14 1.348(19) . ?
C32 C33 1.37(3) . ?
C33 F15 1.34(2) . ?
C28A C33A 1.41(3) . ?
C28A C29A 1.43(3) . ?
C29A F11A 1.32(3) . ?
C29A C30A 1.33(3) . ?
C30A F12A 1.32(3) . ?
C30A C31A 1.34(4) . ?
C31A F13A 1.35(3) . ?
C31A C32A 1.36(4) . ?
C32A F14A 1.26(3) . ?
C32A C33A 1.44(4) . ?
C33A F15A 1.38(3) . ?
C34 C14 1.408(8) 2 ?
C34 C35 1.483(13) . ?
C35 C36 1.385(8) . ?
C35 C36 1.385(8) 2 ?
C36 C37 1.381(10) . ?
C37 C38 1.378(9) . ?
C38 C37 1.378(9) 2 ?
Cl1 C39 1.778(11) . ?
Cl2 C39 1.773(10) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
Cl1A C39A 1.776(17) . ?
Cl2A C39A 1.773(10) . ?
C39A H39C 0.9900 . ?
C39A H39D 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
C4 N1 C1 C15 -172.1(6) . . . . ?
Cu1 N1 C1 C15 16.5(10) . . . . ?
C4 N1 C1 C2 3.8(9) . . . . ?
Cu1 N1 C1 C2 -167.6(5) . . . . ?
N1 C1 C2 C3 -1.7(10) . . . . ?
C15 C1 C2 C3 174.1(7) . . . . ?
C1 C2 C3 C4 -1.0(10) . . . . ?
C1 N1 C4 C5 167.5(7) . . . . ?
Cu1 N1 C4 C5 -21.7(11) . . . . ?
C1 N1 C4 C3 -4.4(8) . . . . ?
Cu1 N1 C4 C3 166.4(5) . . . . ?
C2 C3 C4 C5 -168.5(8) . . . . ?
C2 C3 C4 N1 3.3(9) . . . . ?
N1 C4 C5 C6 9.6(13) . . . . ?
C3 C4 C5 C6 -179.9(8) . . . . ?
N1 C4 C5 C22 -166.1(7) . . . . ?
C3 C4 C5 C22 4.4(12) . . . . ?
C4 C5 C6 C8 -150.0(8) . . . . ?
C22 C5 C6 C8 25.8(11) . . . . ?
C4 C5 C6 C7 36.6(13) . . . . ?
C22 C5 C6 C7 -147.6(7) . . . . ?
Cu1 O1 C7 N2 110.9(7) . . . . ?
Cu1 O1 C7 C6 -69.5(7) . . . . ?
C9 N2 C7 O1 -179.4(7) . . . . ?
Cu2 N2 C7 O1 -1.7(11) . . . . ?
C9 N2 C7 C6 0.9(8) . . . . ?
Cu2 N2 C7 C6 178.6(5) . . . . ?
C8 C6 C7 O1 -178.7(7) . . . . ?
C5 C6 C7 O1 -4.1(12) . . . . ?
C8 C6 C7 N2 1.0(8) . . . . ?
C5 C6 C7 N2 175.5(7) . . . . ?
C5 C6 C8 C9 -177.0(7) . . . . ?
C7 C6 C8 C9 -2.4(8) . . . . ?
C7 N2 C9 C10 177.0(8) . . . . ?
Cu2 N2 C9 C10 -0.8(11) . . . . ?
C7 N2 C9 C8 -2.5(8) . . . . ?
Cu2 N2 C9 C8 179.7(5) . . . . ?
C6 C8 C9 C10 -176.3(7) . . . . ?
C6 C8 C9 N2 3.2(9) . . . . ?
N2 C9 C10 C11 9.6(13) . . . . ?
C8 C9 C10 C11 -171.0(7) . . . . ?
N2 C9 C10 C28 174.8(12) . . . . ?
C8 C9 C10 C28 -5.8(15) . . . . ?
N2 C9 C10 C28A -169.1(14) . . . . ?
C8 C9 C10 C28A 10.3(17) . . . . ?
C14 N3 C11 C12 -3.7(9) . . . . ?
Cu2 N3 C11 C12 167.5(6) . . . . ?
C14 N3 C11 C10 166.5(7) . . . . ?
Cu2 N3 C11 C10 -22.3(11) . . . . ?
C9 C10 C11 N3 2.2(12) . . . . ?
C28 C10 C11 N3 -162.6(11) . . . . ?
C28A C10 C11 N3 -179.0(13) . . . . ?
C9 C10 C11 C12 171.1(8) . . . . ?
C28 C10 C11 C12 6.2(15) . . . . ?
C28A C10 C11 C12 -10.2(16) . . . . ?
N3 C11 C12 C13 2.1(10) . . . . ?
C10 C11 C12 C13 -167.9(8) . . . . ?
C11 C12 C13 C14 0.4(10) . . . . ?
C11 N3 C14 C13 3.9(9) . . . . ?
Cu2 N3 C14 C13 -167.2(5) . . . . ?
C11 N3 C14 C34 -169.6(6) . . . . ?
Cu2 N3 C14 C34 19.3(10) . . . . ?
C12 C13 C14 N3 -2.7(10) . . . . ?
C12 C13 C14 C34 170.6(7) . . . . ?
N1 C1 C15 C1 -9.1(6) . . . 2 ?
C2 C1 C15 C1 175.7(9) . . . 2 ?
N1 C1 C15 C16 -179.0(13) . . . . ?
C2 C1 C15 C16 5.8(14) . . . . ?
C1 C15 C16 C17 100.9(14) . . . . ?
C1 C15 C16 C17 -69.5(16) 2 . . . ?
C1 C15 C16 C21 -83.4(18) . . . . ?
C1 C15 C16 C21 106.2(18) 2 . . . ?
C21 C16 C17 F1 -178(2) . . . . ?
C15 C16 C17 F1 -1.9(17) . . . . ?
C21 C16 C17 C18 0.7(15) . . . . ?
C15 C16 C17 C18 176.3(19) . . . . ?
F1 C17 C18 F2 -1.2(19) . . . . ?
C16 C17 C18 F2 -179.4(15) . . . . ?
F1 C17 C18 C19 179.3(19) . . . . ?
C16 C17 C18 C19 1.1(14) . . . . ?
F2 C18 C19 C20 177.7(19) . . . . ?
C17 C18 C19 C20 -3(3) . . . . ?
F2 C18 C19 F3 1(3) . . . . ?
C17 C18 C19 F3 -179.6(15) . . . . ?
F3 C19 C20 F4 -3(4) . . . . ?
C18 C19 C20 F4 -179(2) . . . . ?
F3 C19 C20 C21 179(2) . . . . ?
C18 C19 C20 C21 3(4) . . . . ?
C17 C16 C21 F5 178(2) . . . . ?
C15 C16 C21 F5 3(4) . . . . ?
C17 C16 C21 C20 -1(3) . . . . ?
C15 C16 C21 C20 -177(2) . . . . ?
C19 C20 C21 F5 180(3) . . . . ?
F4 C20 C21 F5 2(4) . . . . ?
C19 C20 C21 C16 -1(4) . . . . ?
F4 C20 C21 C16 -179(2) . . . . ?
C4 C5 C22 C27 -122.9(9) . . . . ?
C6 C5 C22 C27 60.8(10) . . . . ?
C4 C5 C22 C23 61.8(11) . . . . ?
C6 C5 C22 C23 -114.5(9) . . . . ?
C27 C22 C23 F6 -177.4(8) . . . . ?
C5 C22 C23 F6 -1.9(13) . . . . ?
C27 C22 C23 C24 3.0(13) . . . . ?
C5 C22 C23 C24 178.5(8) . . . . ?
F6 C23 C24 F7 -0.8(14) . . . . ?
C22 C23 C24 F7 178.8(8) . . . . ?
F6 C23 C24 C25 178.5(9) . . . . ?
C22 C23 C24 C25 -1.9(15) . . . . ?
F7 C24 C25 F8 -4.9(17) . . . . ?
C23 C24 C25 F8 175.8(10) . . . . ?
F7 C24 C25 C26 -179.6(11) . . . . ?
C23 C24 C25 C26 1.1(17) . . . . ?
F8 C25 C26 F9 3.1(18) . . . . ?
C24 C25 C26 F9 177.8(11) . . . . ?
F8 C25 C26 C27 -176.3(10) . . . . ?
C24 C25 C26 C27 -1.6(18) . . . . ?
C23 C22 C27 F10 -178.6(8) . . . . ?
C5 C22 C27 F10 5.8(13) . . . . ?
C23 C22 C27 C26 -3.5(14) . . . . ?
C5 C22 C27 C26 -179.1(9) . . . . ?
C25 C26 C27 F10 178.1(10) . . . . ?
F9 C26 C27 F10 -1.3(15) . . . . ?
C25 C26 C27 C22 2.8(17) . . . . ?
F9 C26 C27 C22 -176.6(9) . . . . ?
C9 C10 C28 C29 95(3) . . . . ?
C11 C10 C28 C29 -99(3) . . . . ?
C9 C10 C28 C33 -85(3) . . . . ?
C11 C10 C28 C33 81(3) . . . . ?
C33 C28 C29 F11 179(2) . . . . ?
C10 C28 C29 F11 -1(4) . . . . ?
C33 C28 C29 C30 -4(4) . . . . ?
C10 C28 C29 C30 175(2) . . . . ?
C28 C29 C30 C31 1(4) . . . . ?
F11 C29 C30 C31 178(2) . . . . ?
C28 C29 C30 F12 179(2) . . . . ?
F11 C29 C30 F12 -5(3) . . . . ?
F12 C30 C31 F13 2(3) . . . . ?
C29 C30 C31 F13 178.9(19) . . . . ?
F12 C30 C31 C32 -175(2) . . . . ?
C29 C30 C31 C32 2(3) . . . . ?
C30 C31 C32 F14 176.8(18) . . . . ?
F13 C31 C32 F14 0(3) . . . . ?
C30 C31 C32 C33 -2(3) . . . . ?
F13 C31 C32 C33 -179.3(18) . . . . ?
F14 C32 C33 F15 5(3) . . . . ?
C31 C32 C33 F15 -176(2) . . . . ?
F14 C32 C33 C28 -180(2) . . . . ?
C31 C32 C33 C28 -1(3) . . . . ?
C29 C28 C33 F15 179(2) . . . . ?
C10 C28 C33 F15 0(4) . . . . ?
C29 C28 C33 C32 4(4) . . . . ?
C10 C28 C33 C32 -175(2) . . . . ?
C9 C10 C28A C33A -77(3) . . . . ?
C11 C10 C28A C33A 104(3) . . . . ?
C9 C10 C28A C29A 108(4) . . . . ?
C11 C10 C28A C29A -71(4) . . . . ?
C33A C28A C29A F11A 179(2) . . . . ?
C10 C28A C29A F11A -6(5) . . . . ?
C33A C28A C29A C30A 4(5) . . . . ?
C10 C28A C29A C30A 179(3) . . . . ?
F11A C29A C30A F12A 5(3) . . . . ?
C28A C29A C30A F12A 179(3) . . . . ?
F11A C29A C30A C31A -179(2) . . . . ?
C28A C29A C30A C31A -5(4) . . . . ?
F12A C30A C31A F13A 4(4) . . . . ?
C29A C30A C31A F13A -172(2) . . . . ?
F12A C30A C31A C32A 179(2) . . . . ?
C29A C30A C31A C32A 2(4) . . . . ?
C30A C31A C32A F14A -178(2) . . . . ?
F13A C31A C32A F14A -3(4) . . . . ?
C30A C31A C32A C33A 0(4) . . . . ?
F13A C31A C32A C33A 175.4(19) . . . . ?
C29A C28A C33A F15A 177(2) . . . . ?
C10 C28A C33A F15A 1(4) . . . . ?
C29A C28A C33A C32A -1(4) . . . . ?
C10 C28A C33A C32A -177(2) . . . . ?
F14A C32A C33A F15A 0(3) . . . . ?
C31A C32A C33A F15A -179(2) . . . . ?
F14A C32A C33A C28A 178(3) . . . . ?
C31A C32A C33A C28A -1(4) . . . . ?
N3 C14 C34 C14 -9.9(5) . . . 2 ?
C13 C14 C34 C14 177.6(8) . . . 2 ?
N3 C14 C34 C35 170.1(5) . . . . ?
C13 C14 C34 C35 -2.4(8) . . . . ?
C14 C34 C35 C36 102.4(5) 2 . . . ?
C14 C34 C35 C36 -77.6(5) . . . . ?
C14 C34 C35 C36 -77.6(5) 2 . . 2 ?
C14 C34 C35 C36 102.4(5) . . . 2 ?
C36 C35 C36 F16 179.7(8) 2 . . . ?
C34 C35 C36 F16 -0.3(8) . . . . ?
C36 C35 C36 C37 0.9(6) 2 . . . ?
C34 C35 C36 C37 -179.1(6) . . . . ?
F16 C36 C37 F17 -1.6(12) . . . . ?
C35 C36 C37 F17 177.2(6) . . . . ?
F16 C36 C37 C38 179.4(6) . . . . ?
C35 C36 C37 C38 -1.8(11) . . . . ?
F17 C37 C38 F18 1.9(9) . . . . ?
C36 C37 C38 F18 -179.1(6) . . . . ?
F17 C37 C38 C37 -178.1(9) . . . 2 ?
C36 C37 C38 C37 0.9(6) . . . 2 ?
