#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:34:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179413 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/10/4331007.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_4331007
loop_
_publ_author_name
'Aline Arnold'
'Christian Limberg'
'Ramona Metzinger'
_publ_contact_author_address
;
      Institut fuer Chemie
      Humboldt Universitaet zu Berlin
      Brook-Taylor-Str. 2
      12489 Berlin
      Germany
;
_publ_contact_author_email       ramona.metzinger@chemie.hu-berlin.de
_publ_contact_author_fax         0049-30-20936966
_publ_contact_author_name        'Ramona Metzinger'
_publ_contact_author_phone       0049-30-20937391
_publ_section_title
;
 Chiral Tripodal Ligand Containing Three N-Heterocyclic Donor Functions
 and Its Copper Complexes: Crystallization of [LCuI]22+/[L2CuII]2+
 Stereoisomers and Tyrosinase Activity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              12210
_journal_page_last               12217
_journal_paper_doi               10.1021/ic301391s
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety
'C54 H50 Cu1.35 N10 O2, 2(C F3 O3 S), 2(C2 H3 N)'
_chemical_formula_sum            'C60 H56 Cu1.35 F6 N12 O8 S2'
_chemical_formula_weight         1337.07
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.207(5)
_cell_angle_beta                 105.279(5)
_cell_angle_gamma                110.881(4)
_cell_formula_units_Z            1
_cell_length_a                   10.5204(6)
_cell_length_b                   12.7204(7)
_cell_length_c                   13.2698(9)
_cell_measurement_reflns_used    12531
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.17
_cell_volume                     1457.02(19)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'SHELXS97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Stoe IPDS-2t diffractometer'
_diffrn_measurement_method       'ω-rotation,ω-incr.=1°,319 exposures'
_diffrn_radiation_collimation    '0.5 mm diameter monocapillary'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_source         'long fine focus sealed x-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.1301
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14268
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        'no decay'
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_correction_T_min  0.9284
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'STOE X-RED'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       block
_exptl_crystal_F_000             690.6
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       0.088(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         5438
_refine_ls_number_restraints     259
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1553
_refine_ls_R_factor_gt           0.1004
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1633P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2655
_refine_ls_wR_factor_ref         0.2907
_reflns_d_resolution_high        0.825
_reflns_d_resolution_low         9.377
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3016
_reflns_number_total             5438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301391s_si_001_1.cif
_cod_data_source_block           aa278_supportinginfo_complex2
_cod_database_code               4331007
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 0.5000 0.0436(7) Uani 0.649(3) 2 d SP . .
Cu2 Cu 0.0576(2) 0.5066(2) 0.4165(2) 0.0403(9) Uani 0.351(3) 1 d P . .
C1 C 0.0481(8) 0.2771(6) 0.5290(6) 0.0463(16) Uani 1 1 d U . .
C2 C 0.1483(9) 0.1559(8) 0.4353(8) 0.073(3) Uani 1 1 d . . .
H2A H 0.0846 0.1441 0.3601 0.110 Uiso 1 1 calc R A .
H2B H 0.1610 0.0819 0.4283 0.110 Uiso 1 1 calc R . .
H2C H 0.2457 0.2274 0.4634 0.110 Uiso 1 1 calc R . .
C3 C 0.1896(7) 0.3960(6) 0.5681(6) 0.0412(15) Uani 1 1 d . A .
C4 C 0.3518(7) 0.5765(6) 0.5945(6) 0.0443(16) Uani 1 1 d . A .
C5 C 0.4245(7) 0.5371(6) 0.6652(5) 0.0393(15) Uani 1 1 d . . .
C6 C 0.3526(8) 0.3495(7) 0.7109(6) 0.0487(17) Uani 1 1 d . . .
H6A H 0.2686 0.2661 0.6747 0.073 Uiso 1 1 calc R A .
H6B H 0.3677 0.3895 0.7908 0.073 Uiso 1 1 calc R . .
H6C H 0.4427 0.3444 0.7088 0.073 Uiso 1 1 calc R . .
C7 C 0.4183(5) 0.6929(4) 0.5798(4) 0.0462(16) Uani 1 1 d G . .
C8 C 0.3897(6) 0.6920(5) 0.4713(4) 0.062(2) Uani 1 1 d G A .
H8 H 0.3234 0.6169 0.4052 0.075 Uiso 1 1 calc R . .
C9 C 0.4578(6) 0.8005(5) 0.4593(5) 0.066(2) Uani 1 1 d G A .
H9 H 0.4382 0.7998 0.3850 0.079 Uiso 1 1 calc R . .
C10 C 0.5546(6) 0.9100(5) 0.5558(5) 0.062(2) Uani 1 1 d G A .
H10 H 0.6012 0.9843 0.5476 0.075 Uiso 1 1 calc R . .
C11 C 0.5832(5) 0.9109(4) 0.6643(5) 0.059(2) Uani 1 1 d G A .
H11 H 0.6495 0.9860 0.7304 0.071 Uiso 1 1 calc R . .
C12 C 0.5151(5) 0.8024(4) 0.6763(4) 0.0486(17) Uani 1 1 d G A .
H12 H 0.5347 0.8031 0.7506 0.058 Uiso 1 1 calc R . .
C13 C 0.5836(10) 0.6022(12) 0.7478(8) 0.041(4) Uani 0.649(3) 1 d PGU A 1
C14 C 0.6196(9) 0.6307(11) 0.8627(8) 0.045(3) Uani 0.649(3) 1 d PGU A 1
H14 H 0.5434 0.6140 0.8906 0.053 Uiso 0.649(3) 1 calc PR A 1
C15 C 0.7659(10) 0.6835(10) 0.9374(8) 0.055(4) Uani 0.649(3) 1 d PGU A 1
H15 H 0.7909 0.7032 1.0168 0.066 Uiso 0.649(3) 1 calc PR A 1
C16 C 0.8762(10) 0.7077(9) 0.8971(8) 0.054(3) Uani 0.649(3) 1 d PGU A 1
H16 H 0.9773 0.7441 0.9487 0.065 Uiso 0.649(3) 1 calc PR A 1
C17 C 0.8402(10) 0.6791(9) 0.7822(9) 0.052(3) Uani 0.649(3) 1 d PGU A 1
H17 H 0.9163 0.6958 0.7543 0.063 Uiso 0.649(3) 1 calc PR A 1
C18 C 0.6938(10) 0.6264(11) 0.7075(8) 0.044(3) Uani 0.649(3) 1 d PGU A 1
H18 H 0.6689 0.6066 0.6281 0.053 Uiso 0.649(3) 1 calc PR A 1
C132 C 0.5840(16) 0.586(2) 0.7282(13) 0.034(6) Uani 0.351(3) 1 d PGU A 2
C142 C 0.6421(15) 0.6144(18) 0.8461(13) 0.042(6) Uani 0.351(3) 1 d PGU A 2
H142 H 0.5768 0.5925 0.8828 0.050 Uiso 0.351(3) 1 calc PR A 2
C152 C 0.7967(14) 0.6756(14) 0.9097(12) 0.028(4) Uani 0.351(3) 1 d PGU A 2
H152 H 0.8361 0.6950 0.9894 0.033 Uiso 0.351(3) 1 calc PR A 2
C162 C 0.8932(14) 0.7080(13) 0.8554(12) 0.029(4) Uani 0.351(3) 1 d PGU A 2
H162 H 0.9978 0.7494 0.8984 0.034 Uiso 0.351(3) 1 calc PR A 2
C172 C 0.8351(15) 0.6792(15) 0.7375(12) 0.036(5) Uani 0.351(3) 1 d PGU A 2
H172 H 0.9004 0.7012 0.7008 0.043 Uiso 0.351(3) 1 calc PR A 2
C182 C 0.6805(17) 0.6181(19) 0.6739(13) 0.038(5) Uani 0.351(3) 1 d PGU A 2
H182 H 0.6411 0.5987 0.5942 0.045 Uiso 0.351(3) 1 calc PR A 2
C19 C -0.0741(7) 0.2495(6) 0.4178(6) 0.0429(16) Uani 1 1 d . A .
C20 C -0.2617(8) 0.1431(7) 0.2487(6) 0.0485(17) Uani 1 1 d . A .
H20 H -0.3412 0.0774 0.1801 0.058 Uiso 1 1 calc R . .
C21 C -0.2053(7) 0.2637(7) 0.2732(7) 0.0487(17) Uani 1 1 d . A .
H21 H -0.2410 0.2987 0.2248 0.058 Uiso 1 1 calc R . .
C22 C -0.2204(9) 0.0146(8) 0.3525(8) 0.067(2) Uani 1 1 d . A .
H22A H -0.1591 -0.0209 0.3282 0.100 Uiso 1 1 calc R . .
H22B H -0.3257 -0.0422 0.3032 0.100 Uiso 1 1 calc R . .
H22C H -0.2027 0.0277 0.4323 0.100 Uiso 1 1 calc R . .
C23 C -0.0083(11) 0.2968(9) 0.6297(8) 0.033(3) Uani 0.649(3) 1 d PGU A 1
C24 C -0.0343(11) 0.2237(9) 0.6879(8) 0.053(3) Uani 0.649(3) 1 d PGU A 1
H24 H -0.0266 0.1492 0.6652 0.063 Uiso 0.649(3) 1 calc PR A 1
C25 C -0.0712(11) 0.2577(10) 0.7788(8) 0.056(4) Uani 0.649(3) 1 d PGU A 1
H25 H -0.0892 0.2069 0.8193 0.067 Uiso 0.649(3) 1 calc PR A 1
C26 C -0.0822(11) 0.3649(10) 0.8115(8) 0.063(4) Uani 0.649(3) 1 d PGU A 1
H26 H -0.1078 0.3886 0.8747 0.076 Uiso 0.649(3) 1 calc PR A 1
C27 C -0.0562(13) 0.4380(10) 0.7532(9) 0.070(4) Uani 0.649(3) 1 d PGU . 1
H27 H -0.0639 0.5125 0.7759 0.084 Uiso 0.649(3) 1 calc PR A 1
N5 N -0.0193(12) 0.4040(9) 0.6623(8) 0.050(4) Uani 0.649(3) 1 d PGU . 1
C232 C -0.005(2) 0.2789(17) 0.6129(15) 0.054(7) Uani 0.351(3) 1 d PGU A 2
C242 C -0.0153(19) 0.1981(15) 0.6648(14) 0.041(5) Uani 0.351(3) 1 d PGU A 2
H242 H 0.0083 0.1328 0.6389 0.049 Uiso 0.351(3) 1 calc PR A 2
C252 C -0.0599(15) 0.2121(14) 0.7542(13) 0.036(5) Uani 0.351(3) 1 d PGU A 2
H252 H -0.0673 0.1563 0.7899 0.044 Uiso 0.351(3) 1 calc PR A 2
C262 C -0.0940(15) 0.3068(14) 0.7917(12) 0.030(4) Uani 0.351(3) 1 d PGU A 2
H262 H -0.1248 0.3164 0.8534 0.037 Uiso 0.351(3) 1 calc PR A 2
C272 C -0.0834(17) 0.3876(15) 0.7399(12) 0.041(5) Uani 0.351(3) 1 d PGU A 2
H272 H -0.1069 0.4530 0.7658 0.049 Uiso 0.351(3) 1 calc PR A 2
N52 N -0.039(2) 0.3737(17) 0.6505(14) 0.034(5) Uani 0.351(3) 1 d PGU . 2
N1 N 0.2035(6) 0.4880(5) 0.5353(5) 0.0479(14) Uani 1 1 d . . .
N2 N 0.3202(6) 0.4233(5) 0.6477(4) 0.0390(13) Uani 1 1 d . A .
N3 N -0.0884(6) 0.3295(6) 0.3784(6) 0.0527(16) Uani 1 1 d . . .
N4 N -0.1814(6) 0.1328(5) 0.3431(5) 0.0484(15) Uani 1 1 d . . .
O1 O 0.0807(6) 0.1771(5) 0.5145(5) 0.0562(14) Uani 1 1 d . A .
O101 O 0.4643(14) 0.8526(12) 1.0248(12) 0.082(4) Uani 0.649(3) 1 d PDU A 1
O102 O 0.2382(10) 0.7733(10) 1.0295(9) 0.052(2) Uani 0.649(3) 1 d PDU A 1
O103 O 0.4310(10) 0.7906(9) 1.1903(7) 0.052(2) Uani 0.649(3) 1 d PDU A 1
S100 S 0.3855(9) 0.7763(8) 1.0736(7) 0.064(3) Uani 0.649(3) 1 d PDU A 1
C100 C 0.3232(12) 0.6127(9) 0.9970(9) 0.064(4) Uani 0.649(3) 1 d PDU A 1
F101 F 0.2781(12) 0.5741(10) 0.8848(7) 0.074(3) Uani 0.649(3) 1 d PDU A 1
F102 F 0.4374(12) 0.5878(10) 1.0297(8) 0.088(3) Uani 0.649(3) 1 d PDU A 1
F103 F 0.2169(12) 0.5393(8) 1.0161(9) 0.083(3) Uani 0.649(3) 1 d PDU A 1
O201 O 0.421(2) 0.8386(18) 1.1833(12) 0.059(5) Uani 0.351(3) 1 d PDU A 2
O202 O 0.4989(19) 0.826(2) 1.042(2) 0.075(7) Uani 0.351(3) 1 d PDU A 2
O203 O 0.2053(17) 0.716(3) 1.002(2) 0.108(10) Uani 0.351(3) 1 d PDU A 2
S200 S 0.3655(14) 0.7815(13) 1.0615(11) 0.047(3) Uani 0.351(3) 1 d PDU A 2
C200 C 0.3818(18) 0.6409(15) 1.0111(14) 0.058(7) Uani 0.351(3) 1 d PDU A 2
F201 F 0.5264(17) 0.6734(17) 1.0631(14) 0.076(4) Uani 0.351(3) 1 d PDU A 2
F202 F 0.302(2) 0.5643(18) 1.0491(18) 0.096(6) Uani 0.351(3) 1 d PDU A 2
F203 F 0.339(2) 0.602(2) 0.8968(14) 0.077(6) Uani 0.351(3) 1 d PDU A 2
N300 N 0.9642(12) 0.9761(9) 1.1570(8) 0.095(3) Uani 1 1 d . . .
C301 C 0.8807(12) 0.9754(8) 1.0820(8) 0.071(2) Uani 1 1 d . . .
C302 C 0.7751(10) 0.9726(9) 0.9869(8) 0.071(2) Uani 1 1 d . . .
H30A H 0.7929 0.9431 0.9180 0.107 Uiso 1 1 calc R . .
H30B H 0.7856 1.0560 1.0030 0.107 Uiso 1 1 calc R . .
H30C H 0.6743 0.9168 0.9743 0.107 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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
Cu2 Cu1 Cu2 180.00(8) 2_566 .
Cu2 Cu1 N3 71.5(2) 2_566 2_566
Cu2 Cu1 N3 108.5(2) . 2_566
Cu2 Cu1 N3 108.5(2) 2_566 .
Cu2 Cu1 N3 71.5(2) . .
N3 Cu1 N3 179.999(1) 2_566 .
Cu2 Cu1 N1 114.12(19) 2_566 .
Cu2 Cu1 N1 65.88(19) . .
N3 Cu1 N1 95.7(2) 2_566 .
N3 Cu1 N1 84.3(2) . .
Cu2 Cu1 N1 65.88(19) 2_566 2_566
Cu2 Cu1 N1 114.12(19) . 2_566
N3 Cu1 N1 84.3(2) 2_566 2_566
N3 Cu1 N1 95.7(2) . 2_566
N1 Cu1 N1 179.999(1) . 2_566
Cu1 Cu2 N5 118.1(12) . 2_566
Cu1 Cu2 N52 116.2(17) . 2_566
N5 Cu2 N52 8(3) 2_566 2_566
Cu1 Cu2 N1 74.8(2) . .
N5 Cu2 N1 149.4(14) 2_566 .
N52 Cu2 N1 142(2) 2_566 .
Cu1 Cu2 N3 67.9(2) . .
N5 Cu2 N3 124.2(13) 2_566 .
N52 Cu2 N3 132(2) 2_566 .
N1 Cu2 N3 86.1(3) . .
Cu1 Cu2 C27 147.9(10) . 2_566
N5 Cu2 C27 31.4(4) 2_566 2_566
N52 Cu2 C27 36(2) 2_566 2_566
N1 Cu2 C27 135.6(11) . 2_566
N3 Cu2 C27 116.1(10) . 2_566
Cu1 Cu2 Cu2 0.0 . 2_566
N5 Cu2 Cu2 118.1(12) 2_566 2_566
N52 Cu2 Cu2 116.2(17) 2_566 2_566
N1 Cu2 Cu2 74.8(2) . 2_566
N3 Cu2 Cu2 67.9(2) . 2_566
C27 Cu2 Cu2 147.9(10) 2_566 2_566
C232 C1 O1 102.7(9) . .
C232 C1 C3 111.4(10) . .
O1 C1 C3 109.9(5) . .
C232 C1 C19 110.0(10) . .
O1 C1 C19 109.6(5) . .
C3 C1 C19 112.8(6) . .
O1 C1 C23 109.4(6) . .
C3 C1 C23 106.0(6) . .
C19 C1 C23 109.2(6) . .
O1 C2 H2A 109.5 . .
O1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
O1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 N2 110.6(6) . .
N1 C3 C1 127.2(6) . .
N2 C3 C1 122.2(6) . .
C5 C4 N1 108.7(6) . .
C5 C4 C7 126.7(6) . .
N1 C4 C7 124.6(6) . .
C4 C5 N2 106.4(6) . .
C4 C5 C132 129.1(10) . .
N2 C5 C132 123.1(10) . .
C4 C5 C13 128.4(8) . .
N2 C5 C13 125.2(7) . .
N2 C6 H6A 109.5 . .
N2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 C12 120.0 . .
C8 C7 C4 120.8(4) . .
C12 C7 C4 119.1(4) . .
C7 C8 C9 120.0 . .
C7 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
C10 C9 C8 120.0 . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C9 C10 C11 120.0 . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
C12 C11 C10 120.0 . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C7 120.0 . .
C11 C12 H12 120.0 . .
C7 C12 H12 120.0 . .
C14 C13 C18 120.0 . .
C14 C13 C5 120.2(6) . .
C18 C13 C5 119.7(6) . .
C13 C14 C15 120.0 . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C14 C15 C16 120.0 . .
C14 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
C17 C16 C15 120.0 . .
C17 C16 H16 120.0 . .
C15 C16 H16 120.0 . .
C16 C17 C18 120.0 . .
C16 C17 H17 120.0 . .
C18 C17 H17 120.0 . .
C17 C18 C13 120.0 . .
C17 C18 H18 120.0 . .
C13 C18 H18 120.0 . .
C142 C132 C182 120.0 . .
C142 C132 C5 120.0(10) . .
C182 C132 C5 119.5(10) . .
C132 C142 C152 120.0 . .
C132 C142 H142 120.0 . .
C152 C142 H142 120.0 . .
C142 C152 C162 120.0 . .
C142 C152 H152 120.0 . .
C162 C152 H152 120.0 . .
C172 C162 C152 120.0 . .
C172 C162 H162 120.0 . .
C152 C162 H162 120.0 . .
C162 C172 C182 120.0 . .
C162 C172 H172 120.0 . .
C182 C172 H172 120.0 . .
C172 C182 C132 120.0 . .
C172 C182 H182 120.0 . .
C132 C182 H182 120.0 . .
N3 C19 N4 110.6(6) . .
N3 C19 C1 126.5(6) . .
N4 C19 C1 122.8(6) . .
C21 C20 N4 106.4(6) . .
C21 C20 H20 126.8 . .
N4 C20 H20 126.8 . .
C20 C21 N3 109.9(7) . .
C20 C21 H21 125.1 . .
N3 C21 H21 125.1 . .
N4 C22 H22A 109.5 . .
N4 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
N4 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C24 C23 N5 120.0 . .
C24 C23 C1 126.6(6) . .
N5 C23 C1 113.2(6) . .
C25 C24 C23 120.0 . .
C25 C24 H24 120.0 . .
C23 C24 H24 120.0 . .
C24 C25 C26 120.0 . .
C24 C25 H25 120.0 . .
C26 C25 H25 120.0 . .
C27 C26 C25 120.0 . .
C27 C26 H26 120.0 . .
C25 C26 H26 120.0 . .
C26 C27 N5 120.0 . .
C26 C27 Cu2 158.3(4) . 2_566
C26 C27 H27 120.0 . .
N5 C27 H27 120.0 . .
Cu2 C27 H27 77.9 2_566 .
C27 N5 C23 120.0 . .
C27 N5 Cu2 104.6(6) . 2_566
C23 N5 Cu2 131.8(6) . 2_566
C1 C232 C242 123.9(12) . .
C1 C232 N52 115.9(12) . .
C242 C232 N52 120.0 . .
C252 C242 C232 120.0 . .
C252 C242 H242 120.0 . .
C232 C242 H242 120.0 . .
C262 C252 C242 120.0 . .
C262 C252 H252 120.0 . .
C242 C252 H252 120.0 . .
C252 C262 C272 120.0 . .
C252 C262 H262 120.0 . .
C272 C262 H262 120.0 . .
C262 C272 N52 120.0 . .
C262 C272 H272 120.0 . .
N52 C272 H272 120.0 . .
C272 N52 C232 120.0 . .
C272 N52 Cu2 109.7(8) . 2_566
C232 N52 Cu2 129.9(8) . 2_566
C3 N1 C4 106.4(6) . .
C3 N1 Cu2 131.8(5) . .
C4 N1 Cu2 121.7(5) . .
C3 N1 Cu1 108.4(4) . .
C4 N1 Cu1 132.7(5) . .
C3 N2 C5 107.9(5) . .
C3 N2 C6 128.3(6) . .
C5 N2 C6 123.8(5) . .
C19 N3 C21 106.8(6) . .
C19 N3 Cu1 113.9(5) . .
C21 N3 Cu1 133.9(5) . .
C19 N3 Cu2 131.9(5) . .
C21 N3 Cu2 117.9(5) . .
C19 N4 C20 106.3(6) . .
C19 N4 C22 131.4(7) . .
C20 N4 C22 122.2(6) . .
C1 O1 C2 116.1(6) . .
O103 S100 O101 128.4(9) . .
O103 S100 O102 111.9(8) . .
O101 S100 O102 100.1(9) . .
O103 S100 C100 101.6(7) . .
O101 S100 C100 113.6(8) . .
O102 S100 C100 97.2(7) . .
F103 C100 F101 106.8(10) . .
F103 C100 F102 105.9(9) . .
F101 C100 F102 104.8(10) . .
F103 C100 S100 114.8(8) . .
F101 C100 S100 114.5(8) . .
F102 C100 S100 109.3(8) . .
O201 S200 O202 102.0(16) . .
O201 S200 O203 115.4(16) . .
O202 S200 O203 142.0(18) . .
O201 S200 C200 112.3(14) . .
O202 S200 C200 79.2(13) . .
O203 S200 C200 92.3(15) . .
F201 C200 F203 110.7(16) . .
F201 C200 F202 109.1(16) . .
F203 C200 F202 117.0(18) . .
F201 C200 S200 105.8(13) . .
F203 C200 S200 107.0(13) . .
F202 C200 S200 106.5(14) . .
N300 C301 C302 179.1(10) . .
C301 C302 H30A 109.5 . .
C301 C302 H30B 109.5 . .
H30A C302 H30B 109.5 . .
C301 C302 H30C 109.5 . .
H30A C302 H30C 109.5 . .
H30B C302 H30C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cu2 1.404(2) 2_566
Cu1 Cu2 1.404(2) .
Cu1 N3 1.997(6) 2_566
Cu1 N3 1.997(6) .
Cu1 N1 2.137(6) .
Cu1 N1 2.137(6) 2_566
Cu2 N5 1.82(3) 2_566
Cu2 N52 2.01(6) 2_566
Cu2 N1 2.021(6) .
Cu2 N3 2.044(7) .
Cu2 C27 2.54(4) 2_566
Cu2 Cu2 2.808(4) 2_566
C1 C232 1.367(17) .
C1 O1 1.408(9) .
C1 C3 1.524(9) .
C1 C19 1.531(10) .
C1 C23 1.593(11) .
C2 O1 1.433(10) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 N1 1.333(9) .
C3 N2 1.347(8) .
C4 C5 1.369(10) .
C4 N1 1.388(9) .
C4 C7 1.488(8) .
C5 N2 1.379(8) .
C5 C132 1.459(16) .
C5 C13 1.492(10) .
C6 N2 1.489(9) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.387(7) .
C7 C12 1.387(7) .
C8 C9 1.386(9) .
C8 H8 0.9500 .
C9 C10 1.386(9) .
C9 H9 0.9500 .
C10 C11 1.387(8) .
C10 H10 0.9500 .
C11 C12 1.386(8) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C14 1.375(6) .
C13 C18 1.375(6) .
C14 C15 1.375(6) .
C14 H14 0.9500 .
C15 C16 1.375(6) .
C15 H15 0.9500 .
C16 C17 1.375(6) .
C16 H16 0.9500 .
C17 C18 1.375(6) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C132 C142 1.404(10) .
C132 C182 1.404(10) .
C142 C152 1.404(10) .
C142 H142 0.9500 .
C152 C162 1.404(10) .
C152 H152 0.9500 .
C162 C172 1.404(10) .
C162 H162 0.9500 .
C172 C182 1.404(10) .
C172 H172 0.9500 .
C182 H182 0.9500 .
C19 N3 1.303(9) .
C19 N4 1.362(9) .
C20 C21 1.335(11) .
C20 N4 1.383(9) .
C20 H20 0.9500 .
C21 N3 1.368(9) .
C21 H21 0.9500 .
C22 N4 1.461(10) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 C24 1.367(6) .
C23 N5 1.367(6) .
C24 C25 1.367(6) .
C24 H24 0.9500 .
C25 C26 1.367(6) .
C25 H25 0.9500 .
C26 C27 1.367(6) .
C26 H26 0.9500 .
C27 N5 1.367(6) .
C27 Cu2 2.539(10) 2_566
C27 H27 0.9500 .
N5 Cu2 1.822(10) 2_566
C232 C242 1.377(10) .
C232 N52 1.377(10) .
C242 C252 1.377(10) .
C242 H242 0.9500 .
C252 C262 1.377(10) .
C252 H252 0.9500 .
C262 C272 1.377(10) .
C262 H262 0.9500 .
C272 N52 1.377(10) .
C272 H272 0.9500 .
N52 Cu2 2.007(17) 2_566
O101 S100 1.452(8) .
O102 S100 1.488(8) .
O103 S100 1.432(8) .
S100 C100 1.813(7) .
C100 F103 1.313(9) .
C100 F101 1.318(9) .
C100 F102 1.343(9) .
O201 S200 1.424(10) .
O202 S200 1.435(10) .
O203 S200 1.445(10) .
S200 C200 1.812(7) .
C200 F201 1.342(10) .
C200 F203 1.345(10) .
C200 F202 1.348(10) .
N300 C301 1.136(13) .
C301 C302 1.428(15) .
C302 H30A 0.9800 .
C302 H30B 0.9800 .
C302 H30C 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_4
N3 Cu1 Cu2 N5 -62.0(15) 2_566 2_566
N3 Cu1 Cu2 N5 118.0(15) . 2_566
N1 Cu1 Cu2 N5 -150.0(15) . 2_566
N1 Cu1 Cu2 N5 30.0(15) 2_566 2_566
N3 Cu1 Cu2 N52 -53(2) 2_566 2_566
N3 Cu1 Cu2 N52 127(2) . 2_566
N1 Cu1 Cu2 N52 -141(2) . 2_566
N1 Cu1 Cu2 N52 39(2) 2_566 2_566
N3 Cu1 Cu2 N1 88.0(3) 2_566 .
N3 Cu1 Cu2 N1 -92.0(3) . .
N1 Cu1 Cu2 N1 179.999(3) 2_566 .
N3 Cu1 Cu2 N3 179.999(2) 2_566 .
N1 Cu1 Cu2 N3 92.0(2) . .
N1 Cu1 Cu2 N3 -88.0(2) 2_566 .
N3 Cu1 Cu2 C27 -75.8(19) 2_566 2_566
N3 Cu1 Cu2 C27 104.2(19) . 2_566
N1 Cu1 Cu2 C27 -163.8(19) . 2_566
N1 Cu1 Cu2 C27 16.2(19) 2_566 2_566
C232 C1 C3 N1 -106.1(12) . .
O1 C1 C3 N1 140.8(7) . .
C19 C1 C3 N1 18.2(10) . .
C23 C1 C3 N1 -101.1(8) . .
C232 C1 C3 N2 70.9(12) . .
O1 C1 C3 N2 -42.2(8) . .
C19 C1 C3 N2 -164.8(6) . .
C23 C1 C3 N2 75.8(8) . .
N1 C4 C5 N2 0.8(7) . .
C7 C4 C5 N2 -178.0(6) . .
N1 C4 C5 C132 167.7(11) . .
C7 C4 C5 C132 -11.0(15) . .
N1 C4 C5 C13 -178.1(7) . .
C7 C4 C5 C13 3.1(12) . .
C5 C4 C7 C8 132.2(6) . .
N1 C4 C7 C8 -46.4(8) . .
C5 C4 C7 C12 -45.0(8) . .
N1 C4 C7 C12 136.4(6) . .
C12 C7 C8 C9 0.0 . .
C4 C7 C8 C9 -177.2(5) . .
C7 C8 C9 C10 0.0 . .
C8 C9 C10 C11 0.0 . .
C9 C10 C11 C12 0.0 . .
C10 C11 C12 C7 0.0 . .
C8 C7 C12 C11 0.0 . .
C4 C7 C12 C11 177.2(5) . .
C4 C5 C13 C14 120.0(8) . .
N2 C5 C13 C14 -58.7(11) . .
C132 C5 C13 C14 -142(7) . .
C4 C5 C13 C18 -64.2(11) . .
N2 C5 C13 C18 117.2(8) . .
C132 C5 C13 C18 34(6) . .
C18 C13 C14 C15 0.0 . .
C5 C13 C14 C15 175.8(11) . .
C13 C14 C15 C16 0.0 . .
C14 C15 C16 C17 0.0 . .
C15 C16 C17 C18 0.0 . .
C16 C17 C18 C13 0.0 . .
C14 C13 C18 C17 0.0 . .
C5 C13 C18 C17 -175.8(11) . .
C4 C5 C132 C142 129.0(10) . .
N2 C5 C132 C142 -66.0(15) . .
C13 C5 C132 C142 38(6) . .
C4 C5 C132 C182 -43.0(17) . .
N2 C5 C132 C182 122.0(11) . .
C13 C5 C132 C182 -134(7) . .
C182 C132 C142 C152 0.0 . .
C5 C132 C142 C152 -171.9(18) . .
C132 C142 C152 C162 0.0 . .
C142 C152 C162 C172 0.0 . .
C152 C162 C172 C182 0.0 . .
C162 C172 C182 C132 0.0 . .
C142 C132 C182 C172 0.0 . .
C5 C132 C182 C172 171.9(18) . .
C232 C1 C19 N3 100.9(11) . .
O1 C1 C19 N3 -146.9(7) . .
C3 C1 C19 N3 -24.2(9) . .
C23 C1 C19 N3 93.3(9) . .
C232 C1 C19 N4 -82.0(11) . .
O1 C1 C19 N4 30.1(9) . .
C3 C1 C19 N4 152.9(6) . .
C23 C1 C19 N4 -89.6(8) . .
N4 C20 C21 N3 2.2(8) . .
C232 C1 C23 C24 17(9) . .
O1 C1 C23 C24 -5.1(9) . .
C3 C1 C23 C24 -123.5(7) . .
C19 C1 C23 C24 114.8(7) . .
C232 C1 C23 N5 -168(10) . .
O1 C1 C23 N5 169.9(5) . .
C3 C1 C23 N5 51.5(7) . .
C19 C1 C23 N5 -70.2(7) . .
N5 C23 C24 C25 0.0 . .
C1 C23 C24 C25 174.7(9) . .
C23 C24 C25 C26 0.0 . .
C24 C25 C26 C27 0.0 . .
C25 C26 C27 N5 0.0 . .
C25 C26 C27 Cu2 37.2(13) . 2_566
C26 C27 N5 C23 0.0 . .
Cu2 C27 N5 C23 -161.2(7) 2_566 .
C26 C27 N5 Cu2 161.2(7) . 2_566
C24 C23 N5 C27 0.0 . .
C1 C23 N5 C27 -175.4(8) . .
C24 C23 N5 Cu2 -155.3(9) . 2_566
C1 C23 N5 Cu2 29.3(9) . 2_566
O1 C1 C232 C242 0.9(14) . .
C3 C1 C232 C242 -116.7(11) . .
C19 C1 C232 C242 117.5(11) . .
C23 C1 C232 C242 -158(10) . .
O1 C1 C232 N52 176.5(8) . .
C3 C1 C232 N52 59.0(12) . .
C19 C1 C232 N52 -66.9(11) . .
C23 C1 C232 N52 17(9) . .
C1 C232 C242 C252 175.5(18) . .
N52 C232 C242 C252 0.0 . .
C232 C242 C252 C262 0.0 . .
C242 C252 C262 C272 0.0 . .
C252 C262 C272 N52 0.0 . .
C262 C272 N52 C232 0.0 . .
C262 C272 N52 Cu2 173.6(11) . 2_566
C1 C232 N52 C272 -175.8(16) . .
C242 C232 N52 C272 0.0 . .
C1 C232 N52 Cu2 12.1(13) . 2_566
C242 C232 N52 Cu2 -172.1(14) . 2_566
N2 C3 N1 C4 2.0(8) . .
C1 C3 N1 C4 179.2(6) . .
N2 C3 N1 Cu2 177.3(5) . .
C1 C3 N1 Cu2 -5.4(11) . .
N2 C3 N1 Cu1 -145.5(4) . .
C1 C3 N1 Cu1 31.8(8) . .
C5 C4 N1 C3 -1.7(8) . .
C7 C4 N1 C3 177.1(6) . .
C5 C4 N1 Cu2 -177.6(5) . .
C7 C4 N1 Cu2 1.2(9) . .
C5 C4 N1 Cu1 134.3(6) . .
C7 C4 N1 Cu1 -46.9(10) . .
Cu1 Cu2 N1 C3 65.0(6) . .
N5 Cu2 N1 C3 -175(2) 2_566 .
N52 Cu2 N1 C3 178(3) 2_566 .
N3 Cu2 N1 C3 -3.2(7) . .
C27 Cu2 N1 C3 -127.2(14) 2_566 .
Cu2 Cu2 N1 C3 65.0(6) 2_566 .
Cu1 Cu2 N1 C4 -120.3(5) . .
N5 Cu2 N1 C4 0(2) 2_566 .
N52 Cu2 N1 C4 -7(3) 2_566 .
N3 Cu2 N1 C4 171.6(6) . .
C27 Cu2 N1 C4 47.5(14) 2_566 .
Cu2 Cu2 N1 C4 -120.3(5) 2_566 .
N5 Cu2 N1 Cu1 120(2) 2_566 .
N52 Cu2 N1 Cu1 113(3) 2_566 .
N3 Cu2 N1 Cu1 -68.1(2) . .
C27 Cu2 N1 Cu1 167.8(13) 2_566 .
Cu2 Cu2 N1 Cu1 0.001(4) 2_566 .
Cu2 Cu1 N1 C3 45.4(5) 2_566 .
Cu2 Cu1 N1 C3 -134.6(5) . .
N3 Cu1 N1 C3 117.7(5) 2_566 .
N3 Cu1 N1 C3 -62.3(5) . .
Cu2 Cu1 N1 C4 -89.9(7) 2_566 .
Cu2 Cu1 N1 C4 90.1(7) . .
N3 Cu1 N1 C4 -17.7(7) 2_566 .
N3 Cu1 N1 C4 162.3(7) . .
Cu2 Cu1 N1 Cu2 180.002(4) 2_566 .
N3 Cu1 N1 Cu2 -107.7(2) 2_566 .
N3 Cu1 N1 Cu2 72.3(2) . .
N1 C3 N2 C5 -1.5(7) . .
C1 C3 N2 C5 -178.9(6) . .
N1 C3 N2 C6 177.0(6) . .
C1 C3 N2 C6 -0.4(10) . .
C4 C5 N2 C3 0.4(7) . .
C132 C5 N2 C3 -167.5(10) . .
C13 C5 N2 C3 179.3(7) . .
C4 C5 N2 C6 -178.2(6) . .
C132 C5 N2 C6 13.9(12) . .
C13 C5 N2 C6 0.7(11) . .
N4 C19 N3 C21 -1.9(8) . .
C1 C19 N3 C21 175.4(6) . .
N4 C19 N3 Cu1 155.9(5) . .
C1 C19 N3 Cu1 -26.7(9) . .
N4 C19 N3 Cu2 -159.9(5) . .
C1 C19 N3 Cu2 17.4(11) . .
C20 C21 N3 C19 -0.2(8) . .
C20 C21 N3 Cu1 -151.6(6) . .
C20 C21 N3 Cu2 161.4(5) . .
Cu2 Cu1 N3 C19 -52.7(5) 2_566 .
Cu2 Cu1 N3 C19 127.3(5) . .
N1 Cu1 N3 C19 60.8(5) . .
N1 Cu1 N3 C19 -119.2(5) 2_566 .
Cu2 Cu1 N3 C21 97.2(7) 2_566 .
Cu2 Cu1 N3 C21 -82.8(7) . .
N1 Cu1 N3 C21 -149.3(7) . .
N1 Cu1 N3 C21 30.7(7) 2_566 .
Cu2 Cu1 N3 Cu2 179.999(2) 2_566 .
N1 Cu1 N3 Cu2 -66.5(2) . .
N1 Cu1 N3 Cu2 113.5(2) 2_566 .
Cu1 Cu2 N3 C19 -77.9(7) . .
N5 Cu2 N3 C19 172.4(15) 2_566 .
N52 Cu2 N3 C19 176(2) 2_566 .
N1 Cu2 N3 C19 -2.7(7) . .
C27 Cu2 N3 C19 137.1(13) 2_566 .
Cu2 Cu2 N3 C19 -77.9(7) 2_566 .
Cu1 Cu2 N3 C21 126.0(5) . .
N5 Cu2 N3 C21 16.3(15) 2_566 .
N52 Cu2 N3 C21 20(2) 2_566 .
N1 Cu2 N3 C21 -158.8(6) . .
C27 Cu2 N3 C21 -19.0(13) 2_566 .
Cu2 Cu2 N3 C21 126.0(5) 2_566 .
N5 Cu2 N3 Cu1 -109.8(14) 2_566 .
N52 Cu2 N3 Cu1 -106(2) 2_566 .
N1 Cu2 N3 Cu1 75.2(2) . .
C27 Cu2 N3 Cu1 -145.1(12) 2_566 .
Cu2 Cu2 N3 Cu1 -0.001(2) 2_566 .
N3 C19 N4 C20 3.2(8) . .
C1 C19 N4 C20 -174.2(6) . .
N3 C19 N4 C22 -173.7(8) . .
C1 C19 N4 C22 8.8(12) . .
C21 C20 N4 C19 -3.2(7) . .
C21 C20 N4 C22 174.1(7) . .
C232 C1 O1 C2 -176.2(10) . .
C3 C1 O1 C2 -57.5(8) . .
C19 C1 O1 C2 66.9(7) . .
C23 C1 O1 C2 -173.4(6) . .
O103 S100 C100 F103 57.8(10) . .
O101 S100 C100 F103 -160.8(10) . .
O102 S100 C100 F103 -56.4(10) . .
O103 S100 C100 F101 -178.1(9) . .
O101 S100 C100 F101 -36.7(13) . .
O102 S100 C100 F101 67.7(10) . .
O103 S100 C100 F102 -61.0(9) . .
O101 S100 C100 F102 80.4(11) . .
O102 S100 C100 F102 -175.2(8) . .
O201 S200 C200 F201 -56.4(17) . .
O202 S200 C200 F201 42.2(16) . .
O203 S200 C200 F201 -175.1(17) . .
O201 S200 C200 F203 -174.6(16) . .
O202 S200 C200 F203 -76.0(18) . .
O203 S200 C200 F203 66.7(19) . .
O201 S200 C200 F202 59.6(18) . .
O202 S200 C200 F202 158.2(17) . .
O203 S200 C200 F202 -59.1(19) . .
