#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:57:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178413 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023400.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_4023400
loop_
_publ_author_name
'Jacob M. Plummer'
'Jeremy A. Weitgenant'
'Bruce C. Noll'
'Joseph W. Lauher'
'Olaf Wiest'
'Paul Helquist'
_publ_contact_author_address
;University of Notre Dame
Department of Chemistry and Biochemistry
251 Nieuwland Science Hall
Notre Dame, IN 46556-5670
USA
;
_publ_contact_author_email       Paul.Helquist.1@nd.edu
_publ_contact_author_fax         1(574)6316652
_publ_contact_author_name        'Professor Paul Helquist'
_publ_contact_author_phone       1(574)6317822
_publ_section_title
;
 Synthesis, Structure, and Metal Complexation Behavior of
 a New Type of Functionalized Chiral Phenanthroline Derivative
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3911
_journal_page_last               3914
_journal_paper_doi               10.1021/jo702566m
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        synthesized
_chemical_formula_moiety         '2(C20 H22 Cu N2 O2), 2(C F3 O3 S)'
_chemical_formula_sum            'C22 H22 Cu F6 N2 O8 S2'
_chemical_formula_weight         684.07
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.636(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4152(8)
_cell_length_b                   11.3319(7)
_cell_length_c                   17.8696(10)
_cell_measurement_reflns_used    9544
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.802
_cell_measurement_theta_min      2.181
_cell_volume                     2694.2(3)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XCIF (Sheldrick, 2001)/enCIFer (CCDC, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker SMART Apex CCD diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25621
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_T_max  0.8325
_exptl_absorpt_correction_T_min  0.6593
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'translucent light blue'
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       wedge
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.090(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     744
_refine_ls_number_reflns         10535
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0346P)²+7.0356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                9084
_reflns_number_total             10535
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702566m-File005.cif
_cod_data_source_block           bcn244_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023400
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.45910(6) -0.08632(6) 0.74206(4) 0.02698(18) Uani 1 1 d . . .
N1 N 0.5675(4) -0.0812(6) 0.8516(3) 0.0304(12) Uani 1 1 d . . .
N2 N 0.5473(4) 0.0214(5) 0.7117(3) 0.0284(12) Uani 1 1 d . . .
O1 O 0.3738(4) -0.1875(5) 0.7795(3) 0.0365(12) Uani 1 1 d . . .
O2 O 0.3543(3) -0.0818(5) 0.6320(2) 0.0285(9) Uani 1 1 d . . .
C1 C 0.5722(5) -0.1327(7) 0.9194(4) 0.0325(14) Uani 1 1 d . . .
C2 C 0.6572(6) -0.1133(7) 0.9927(4) 0.0379(17) Uani 1 1 d . . .
H2 H 0.6619 -0.1533 1.0407 0.045 Uiso 1 1 calc R . .
C3 C 0.7320(6) -0.0377(8) 0.9946(4) 0.0429(18) Uani 1 1 d . . .
H3 H 0.7880 -0.0247 1.0439 0.051 Uiso 1 1 calc R . .
C4 C 0.7259(5) 0.0205(8) 0.9238(4) 0.0373(16) Uani 1 1 d . . .
C5 C 0.7988(6) 0.1005(9) 0.9195(4) 0.0470(19) Uani 1 1 d . . .
H5 H 0.8556 0.1180 0.9674 0.056 Uiso 1 1 calc R . .
C6 C 0.7900(6) 0.1524(8) 0.8494(5) 0.0460(18) Uani 1 1 d . . .
H6 H 0.8406 0.2054 0.8485 0.055 Uiso 1 1 calc R . .
C7 C 0.7046(5) 0.1285(7) 0.7756(4) 0.0353(16) Uani 1 1 d . . .
C8 C 0.6881(6) 0.1796(7) 0.6995(5) 0.0393(17) Uani 1 1 d . . .
H8 H 0.7347 0.2353 0.6946 0.047 Uiso 1 1 calc R . .
C9 C 0.6062(6) 0.1495(7) 0.6337(4) 0.0350(15) Uani 1 1 d . . .
H9 H 0.5963 0.1833 0.5825 0.042 Uiso 1 1 calc R . .
C10 C 0.5349(5) 0.0681(6) 0.6399(4) 0.0307(14) Uani 1 1 d . . .
C11 C 0.6314(5) 0.0486(6) 0.7778(4) 0.0305(14) Uani 1 1 d . . .
C12 C 0.6429(5) -0.0050(7) 0.8535(4) 0.0321(15) Uani 1 1 d . . .
C13 C 0.4850(5) -0.2024(6) 0.9204(4) 0.0379(15) Uani 1 1 d . . .
H13A H 0.4383 -0.1473 0.9313 0.045 Uiso 1 1 calc R . .
H13B H 0.5101 -0.2580 0.9666 0.045 Uiso 1 1 calc R . .
C14 C 0.4251(5) -0.2725(6) 0.8450(4) 0.0385(14) Uani 1 1 d . . .
H14 H 0.4719 -0.3223 0.8293 0.046 Uiso 1 1 calc R . .
C15 C 0.3467(7) -0.3504(7) 0.8567(4) 0.0512(19) Uani 1 1 d . . .
H15A H 0.3815 -0.4129 0.8963 0.061 Uiso 1 1 calc R . .
H15B H 0.3077 -0.3896 0.8045 0.061 Uiso 1 1 calc R . .
C16 C 0.2723(7) -0.2868(8) 0.8864(5) 0.058(2) Uani 1 1 d . . .
H16A H 0.3068 -0.2652 0.9436 0.087 Uiso 1 1 calc R . .
H16B H 0.2159 -0.3394 0.8803 0.087 Uiso 1 1 calc R . .
H16C H 0.2470 -0.2153 0.8541 0.087 Uiso 1 1 calc R . .
C17 C 0.4461(6) 0.0286(6) 0.5671(4) 0.0372(16) Uani 1 1 d . . .
H17A H 0.4615 -0.0497 0.5502 0.045 Uiso 1 1 calc R . .
H17B H 0.4370 0.0844 0.5222 0.045 Uiso 1 1 calc R . .
C18 C 0.3470(5) 0.0198(5) 0.5789(3) 0.0332(13) Uani 1 1 d . . .
H18 H 0.3372 0.0932 0.6061 0.040 Uiso 1 1 calc R . .
C19 C 0.2568(6) 0.0033(7) 0.4989(4) 0.0454(17) Uani 1 1 d . . .
H19A H 0.2488 0.0757 0.4660 0.055 Uiso 1 1 calc R . .
H19B H 0.1956 -0.0054 0.5109 0.055 Uiso 1 1 calc R . .
C20 C 0.2637(7) -0.1032(8) 0.4479(5) 0.055(2) Uani 1 1 d . . .
H20A H 0.3199 -0.0919 0.4306 0.083 Uiso 1 1 calc R . .
H20B H 0.2010 -0.1103 0.4000 0.083 Uiso 1 1 calc R . .
H20C H 0.2746 -0.1753 0.4804 0.083 Uiso 1 1 calc R . .
Cu2 Cu 0.03897(6) 0.09014(6) 0.75894(4) 0.02769(18) Uani 1 1 d . . .
N3 N -0.0438(5) -0.0241(5) 0.7918(3) 0.0331(13) Uani 1 1 d . . .
N4 N -0.0738(4) 0.0855(6) 0.6538(3) 0.0270(11) Uani 1 1 d . . .
O3 O 0.1458(4) 0.0877(6) 0.8688(3) 0.0395(12) Uani 1 1 d . . .
O4 O 0.1194(4) 0.1890(5) 0.7179(3) 0.0331(11) Uani 1 1 d . . .
C21 C -0.0226(6) -0.0783(7) 0.8632(4) 0.0389(17) Uani 1 1 d . . .
C22 C -0.0923(8) -0.1570(8) 0.8730(5) 0.052(2) Uani 1 1 d . . .
H22 H -0.0799 -0.1896 0.9250 0.062 Uiso 1 1 calc R . .
C23 C -0.1774(7) -0.1872(8) 0.8090(5) 0.052(2) Uani 1 1 d . . .
H23 H -0.2235 -0.2415 0.8163 0.063 Uiso 1 1 calc R . .
C24 C -0.1977(6) -0.1380(7) 0.7311(5) 0.0429(18) Uani 1 1 d . . .
C25 C -0.2817(6) -0.1649(8) 0.6583(5) 0.048(2) Uani 1 1 d . . .
H25 H -0.3298 -0.2210 0.6600 0.057 Uiso 1 1 calc R . .
C26 C -0.2941(6) -0.1139(7) 0.5888(5) 0.048(2) Uani 1 1 d . . .
H26 H -0.3498 -0.1366 0.5415 0.057 Uiso 1 1 calc R . .
C27 C -0.2264(5) -0.0251(8) 0.5819(5) 0.0410(17) Uani 1 1 d . . .
C28 C -0.2362(6) 0.0354(8) 0.5118(5) 0.0433(18) Uani 1 1 d . . .
H28 H -0.2899 0.0173 0.4620 0.052 Uiso 1 1 calc R . .
C29 C -0.1686(6) 0.1206(7) 0.5145(4) 0.0415(18) Uani 1 1 d . . .
H29 H -0.1777 0.1641 0.4667 0.050 Uiso 1 1 calc R . .
C30 C -0.0863(5) 0.1457(6) 0.5857(4) 0.0329(14) Uani 1 1 d . . .
C31 C -0.1425(5) 0.0035(6) 0.6530(4) 0.0334(15) Uani 1 1 d . . .
C32 C -0.1269(6) -0.0534(6) 0.7279(4) 0.0337(16) Uani 1 1 d . . .
C33 C 0.0732(7) -0.0543(7) 0.9309(4) 0.050(2) Uani 1 1 d . . .
H33A H 0.1239 -0.1102 0.9269 0.060 Uiso 1 1 calc R . .
H33B H 0.0644 -0.0721 0.9820 0.060 Uiso 1 1 calc R . .
C34 C 0.1159(6) 0.0695(6) 0.9375(4) 0.0417(15) Uani 1 1 d . . .
H34 H 0.0612 0.1269 0.9326 0.050 Uiso 1 1 calc R . .
C35 C 0.2062(7) 0.0956(8) 1.0171(5) 0.058(2) Uani 1 1 d . . .
H35A H 0.2273 0.1785 1.0158 0.070 Uiso 1 1 calc R . .
H35B H 0.1840 0.0880 1.0628 0.070 Uiso 1 1 calc R . .
C36 C 0.2974(8) 0.0153(11) 1.0332(5) 0.076(3) Uani 1 1 d . . .
H36A H 0.2793 -0.0662 1.0401 0.114 Uiso 1 1 calc R . .
H36B H 0.3528 0.0412 1.0826 0.114 Uiso 1 1 calc R . .
H36C H 0.3184 0.0194 0.9872 0.114 Uiso 1 1 calc R . .
C37 C -0.0114(5) 0.2414(6) 0.5923(4) 0.0340(14) Uani 1 1 d . . .
H37A H -0.0226 0.3074 0.6241 0.041 Uiso 1 1 calc R . .
H37B H -0.0241 0.2716 0.5372 0.041 Uiso 1 1 calc R . .
C38 C 0.0988(5) 0.2030(6) 0.6318(3) 0.0340(13) Uani 1 1 d . . .
H38 H 0.1074 0.1253 0.6088 0.041 Uiso 1 1 calc R . .
C39 C 0.1711(5) 0.2921(6) 0.6206(4) 0.0361(13) Uani 1 1 d . . .
H39A H 0.2406 0.2625 0.6487 0.043 Uiso 1 1 calc R . .
H39B H 0.1580 0.2974 0.5621 0.043 Uiso 1 1 calc R . .
C40 C 0.1644(6) 0.4150(6) 0.6518(4) 0.0448(16) Uani 1 1 d . . .
H40A H 0.0977 0.4481 0.6211 0.067 Uiso 1 1 calc R . .
H40B H 0.2158 0.4656 0.6451 0.067 Uiso 1 1 calc R . .
H40C H 0.1754 0.4108 0.7094 0.067 Uiso 1 1 calc R . .
S1 S 0.47695(13) -0.34068(15) 0.65090(9) 0.0296(3) Uani 1 1 d . . .
O5 O 0.5365(4) -0.2551(4) 0.7105(3) 0.0315(10) Uani 1 1 d . . .
O6 O 0.3854(4) -0.3731(5) 0.6591(3) 0.0435(12) Uani 1 1 d . . .
O7 O 0.4709(4) -0.3215(5) 0.5704(3) 0.0440(12) Uani 1 1 d . . .
C41 C 0.5537(7) -0.4728(7) 0.6812(4) 0.0455(18) Uani 1 1 d . . .
F1 F 0.6433(4) -0.4567(5) 0.6762(3) 0.0558(12) Uani 1 1 d . . .
F2 F 0.5725(4) -0.5026(5) 0.7580(3) 0.0637(13) Uani 1 1 d . . .
F3 F 0.5091(4) -0.5648(4) 0.6349(3) 0.0679(14) Uani 1 1 d . . .
S2 S 0.01229(15) 0.36029(18) 0.84034(10) 0.0378(4) Uani 1 1 d . . .
O8 O -0.0416(4) 0.2654(5) 0.7863(3) 0.0413(13) Uani 1 1 d . . .
O9 O 0.0152(6) 0.3501(6) 0.9200(3) 0.0701(19) Uani 1 1 d . . .
O10 O 0.1049(5) 0.3962(9) 0.8328(4) 0.095(3) Uani 1 1 d . . .
C42 C -0.0657(10) 0.4863(8) 0.7996(6) 0.071(3) Uani 1 1 d . . .
F4 F 0.5465(4) 0.2636(5) 0.8270(3) 0.0600(14) Uani 1 1 d . . .
F5 F 0.4053(4) 0.3485(5) 0.7621(3) 0.0603(13) Uani 1 1 d . . .
F6 F 0.4767(4) 0.3646(4) 0.8909(3) 0.0514(11) Uani 1 1 d . . .
S3 S 0.39380(13) 0.15760(16) 0.84169(10) 0.0318(4) Uani 1 1 d . . .
O11 O 0.3784(4) 0.0917(5) 0.7684(3) 0.0336(10) Uani 1 1 d . . .
O12 O 0.3013(4) 0.2070(5) 0.8436(3) 0.0397(12) Uani 1 1 d . . .
O13 O 0.4600(4) 0.1068(5) 0.9162(3) 0.0419(12) Uani 1 1 d . . .
C43 C 0.4587(6) 0.2900(7) 0.8294(4) 0.0391(16) Uani 1 1 d . . .
F7 F -0.0514(4) -0.2562(5) 0.6609(4) 0.0731(18) Uani 1 1 d . . .
F8 F 0.0903(5) -0.3456(5) 0.7142(3) 0.0656(15) Uani 1 1 d . . .
F9 F 0.0120(4) -0.3449(4) 0.5858(3) 0.0509(11) Uani 1 1 d . . .
S4 S 0.09933(13) -0.14477(16) 0.64712(10) 0.0319(4) Uani 1 1 d . . .
O14 O 0.1917(4) -0.1879(5) 0.6430(3) 0.0428(12) Uani 1 1 d . . .
O15 O 0.0332(4) -0.0889(5) 0.5746(3) 0.0390(11) Uani 1 1 d . . .
O16 O 0.1138(4) -0.0832(6) 0.7218(3) 0.0447(13) Uani 1 1 d . . .
C44 C 0.0341(6) -0.2804(7) 0.6520(5) 0.0439(18) Uani 1 1 d . . .
F10 F -0.0798(7) 0.5071(7) 0.7240(4) 0.134(4) Uani 1 1 d . . .
F11 F -0.1552(6) 0.4714(8) 0.8019(5) 0.126(3) Uani 1 1 d . . .
F12 F -0.0227(7) 0.5824(6) 0.8437(4) 0.133(3) 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'
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
_geom_angle_publ_flag
O2 Cu1 O1 90.90(19) . . ?
O2 Cu1 N1 176.4(3) . . ?
O1 Cu1 N1 92.2(2) . . ?
O2 Cu1 N2 92.1(2) . . ?
O1 Cu1 N2 176.0(2) . . ?
N1 Cu1 N2 84.7(2) . . ?
O2 Cu1 O5 91.92(19) . . ?
O1 Cu1 O5 91.3(2) . . ?
N1 Cu1 O5 89.7(2) . . ?
N2 Cu1 O5 91.2(2) . . ?
C1 N1 C12 119.4(6) . . ?
C1 N1 Cu1 129.4(5) . . ?
C12 N1 Cu1 111.0(4) . . ?
C10 N2 C11 119.3(6) . . ?
C10 N2 Cu1 130.2(5) . . ?
C11 N2 Cu1 110.6(4) . . ?
C14 O1 Cu1 117.4(4) . . ?
C18 O2 Cu1 120.2(4) . . ?
N1 C1 C2 119.8(7) . . ?
N1 C1 C13 119.9(6) . . ?
C2 C1 C13 120.1(6) . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C12 C4 C3 116.8(7) . . ?
C12 C4 C5 119.0(7) . . ?
C3 C4 C5 124.2(7) . . ?
C6 C5 C4 121.7(7) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.8(8) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C11 C7 C8 116.3(7) . . ?
C11 C7 C6 118.8(7) . . ?
C8 C7 C6 124.9(7) . . ?
C9 C8 C7 120.1(7) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.9(6) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N2 C10 C9 120.1(6) . . ?
N2 C10 C17 118.0(6) . . ?
C9 C10 C17 121.9(6) . . ?
N2 C11 C7 123.3(6) . . ?
N2 C11 C12 117.6(6) . . ?
C7 C11 C12 119.1(6) . . ?
N1 C12 C4 123.3(6) . . ?
N1 C12 C11 116.0(6) . . ?
C4 C12 C11 120.7(7) . . ?
C1 C13 C14 117.4(5) . . ?
C1 C13 H13A 107.9 . . ?
C14 C13 H13A 107.9 . . ?
C1 C13 H13B 107.9 . . ?
C14 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
O1 C14 C15 108.5(6) . . ?
O1 C14 C13 107.7(5) . . ?
C15 C14 C13 112.6(5) . . ?
O1 C14 H14 109.3 . . ?
C15 C14 H14 109.3 . . ?
C13 C14 H14 109.3 . . ?
C14 C15 C16 115.4(7) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 C18 115.6(5) . . ?
C10 C17 H17A 108.4 . . ?
C18 C17 H17A 108.4 . . ?
C10 C17 H17B 108.4 . . ?
C18 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
O2 C18 C17 107.6(5) . . ?
O2 C18 C19 109.4(5) . . ?
C17 C18 C19 112.5(5) . . ?
O2 C18 H18 109.1 . . ?
C17 C18 H18 109.1 . . ?
C19 C18 H18 109.1 . . ?
C18 C19 C20 115.1(6) . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 Cu2 N4 92.8(2) . . ?
O4 Cu2 O3 91.9(2) . . ?
N4 Cu2 O3 175.3(2) . . ?
O4 Cu2 N3 173.7(2) . . ?
N4 Cu2 N3 84.0(2) . . ?
O3 Cu2 N3 91.4(2) . . ?
C32 N3 C21 120.0(6) . . ?
C32 N3 Cu2 110.4(4) . . ?
C21 N3 Cu2 129.3(5) . . ?
C30 N4 C31 119.7(6) . . ?
C30 N4 Cu2 128.9(5) . . ?
C31 N4 Cu2 111.3(4) . . ?
C34 O3 Cu2 117.8(4) . . ?
C38 O4 Cu2 123.4(4) . . ?
N3 C21 C22 119.9(8) . . ?
N3 C21 C33 119.7(7) . . ?
C22 C21 C33 120.4(7) . . ?
C23 C22 C21 120.7(7) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.3(7) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C32 C24 C23 115.2(8) . . ?
C32 C24 C25 118.6(7) . . ?
C23 C24 C25 126.2(7) . . ?
C26 C25 C24 121.7(7) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C27 122.4(8) . . ?
C25 C26 H26 118.8 . . ?
C27 C26 H26 118.8 . . ?
C28 C27 C31 117.0(7) . . ?
C28 C27 C26 125.9(7) . . ?
C31 C27 C26 117.2(7) . . ?
C29 C28 C27 119.8(7) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 121.6(7) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
N4 C30 C29 119.5(7) . . ?
N4 C30 C37 116.9(6) . . ?
C29 C30 C37 123.5(6) . . ?
N4 C31 C27 122.4(7) . . ?
N4 C31 C32 116.8(6) . . ?
C27 C31 C32 120.8(7) . . ?
N3 C32 C24 123.6(6) . . ?
N3 C32 C31 117.1(6) . . ?
C24 C32 C31 119.3(7) . . ?
C21 C33 C34 117.4(6) . . ?
C21 C33 H33A 108.0 . . ?
C34 C33 H33A 108.0 . . ?
C21 C33 H33B 108.0 . . ?
C34 C33 H33B 108.0 . . ?
H33A C33 H33B 107.2 . . ?
O3 C34 C33 107.8(5) . . ?
O3 C34 C35 109.3(6) . . ?
C33 C34 C35 115.0(6) . . ?
O3 C34 H34 108.2 . . ?
C33 C34 H34 108.2 . . ?
C35 C34 H34 108.2 . . ?
C36 C35 C34 114.7(7) . . ?
C36 C35 H35A 108.6 . . ?
C34 C35 H35A 108.6 . . ?
C36 C35 H35B 108.6 . . ?
C34 C35 H35B 108.6 . . ?
H35A C35 H35B 107.6 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C30 C37 C38 114.7(5) . . ?
C30 C37 H37A 108.6 . . ?
C38 C37 H37A 108.6 . . ?
C30 C37 H37B 108.6 . . ?
C38 C37 H37B 108.6 . . ?
H37A C37 H37B 107.6 . . ?
O4 C38 C39 109.9(5) . . ?
O4 C38 C37 105.7(5) . . ?
C39 C38 C37 113.1(5) . . ?
O4 C38 H38 109.3 . . ?
C39 C38 H38 109.3 . . ?
C37 C38 H38 109.3 . . ?
C40 C39 C38 114.7(5) . . ?
C40 C39 H39A 108.6 . . ?
C38 C39 H39A 108.6 . . ?
C40 C39 H39B 108.6 . . ?
C38 C39 H39B 108.6 . . ?
H39A C39 H39B 107.6 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O7 S1 O6 116.2(3) . . ?
O7 S1 O5 115.3(3) . . ?
O6 S1 O5 113.9(3) . . ?
O7 S1 C41 102.7(3) . . ?
O6 S1 C41 103.8(4) . . ?
O5 S1 C41 102.2(3) . . ?
S1 O5 Cu1 120.7(3) . . ?
F3 C41 F2 107.4(7) . . ?
F3 C41 F1 108.1(6) . . ?
F2 C41 F1 106.4(7) . . ?
F3 C41 S1 111.6(6) . . ?
F2 C41 S1 112.0(5) . . ?
F1 C41 S1 111.1(5) . . ?
O9 S2 O10 116.4(4) . . ?
O9 S2 O8 114.2(4) . . ?
O10 S2 O8 114.9(4) . . ?
O9 S2 C42 104.2(5) . . ?
O10 S2 C42 101.2(6) . . ?
O8 S2 C42 103.2(4) . . ?
F10 C42 F11 106.9(10) . . ?
F10 C42 F12 108.2(9) . . ?
F11 C42 F12 108.7(11) . . ?
F10 C42 S2 112.8(9) . . ?
F11 C42 S2 110.7(8) . . ?
F12 C42 S2 109.4(7) . . ?
O13 S3 O11 116.7(3) . . ?
O13 S3 O12 115.0(3) . . ?
O11 S3 O12 113.3(3) . . ?
O13 S3 C43 104.7(3) . . ?
O11 S3 C43 102.9(3) . . ?
O12 S3 C43 101.7(3) . . ?
F4 C43 F5 108.2(6) . . ?
F4 C43 F6 106.8(6) . . ?
F5 C43 F6 107.0(7) . . ?
F4 C43 S3 111.1(6) . . ?
F5 C43 S3 111.9(5) . . ?
F6 C43 S3 111.6(5) . . ?
O15 S4 O14 114.1(3) . . ?
O15 S4 O16 115.6(3) . . ?
O14 S4 O16 113.6(3) . . ?
O15 S4 C44 104.0(4) . . ?
O14 S4 C44 102.7(4) . . ?
O16 S4 C44 104.9(3) . . ?
F8 C44 F9 107.6(7) . . ?
F8 C44 F7 108.2(6) . . ?
F9 C44 F7 107.8(7) . . ?
F8 C44 S4 110.6(6) . . ?
F9 C44 S4 112.0(5) . . ?
F7 C44 S4 110.5(6) . . ?
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 O2 1.967(4) . ?
Cu1 O1 1.977(5) . ?
Cu1 N1 1.980(6) . ?
Cu1 N2 1.983(5) . ?
Cu1 O5 2.389(5) . ?
N1 C1 1.324(8) . ?
N1 C12 1.378(9) . ?
N2 C10 1.334(8) . ?
N2 C11 1.364(9) . ?
O1 C14 1.475(8) . ?
O2 C18 1.468(7) . ?
C1 C2 1.424(10) . ?
C1 C13 1.491(10) . ?
C2 C3 1.367(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(10) . ?
C3 H3 0.9500 . ?
C4 C12 1.392(10) . ?
C4 C5 1.412(11) . ?
C5 C6 1.345(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.442(11) . ?
C6 H6 0.9500 . ?
C7 C11 1.402(10) . ?
C7 C8 1.411(10) . ?
C8 C9 1.352(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(10) . ?
C9 H9 0.9500 . ?
C10 C17 1.500(9) . ?
C11 C12 1.433(9) . ?
C13 C14 1.515(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.511(9) . ?
C14 H14 1.0000 . ?
C15 C16 1.545(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.526(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.529(9) . ?
C18 H18 1.0000 . ?
C19 C20 1.540(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
Cu2 O4 1.948(5) . ?
Cu2 N4 1.955(6) . ?
Cu2 O3 1.974(4) . ?
Cu2 N3 1.996(6) . ?
N3 C32 1.340(10) . ?
N3 C21 1.341(9) . ?
N4 C30 1.346(8) . ?
N4 C31 1.354(9) . ?
O3 C34 1.464(7) . ?
O4 C38 1.458(7) . ?
C21 C22 1.404(11) . ?
C21 C33 1.469(12) . ?
C22 C23 1.361(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.422(11) . ?
C23 H23 0.9500 . ?
C24 C32 1.417(10) . ?
C24 C25 1.428(12) . ?
C25 C26 1.318(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.440(11) . ?
C26 H26 0.9500 . ?
C27 C28 1.387(11) . ?
C27 C31 1.414(10) . ?
C28 C29 1.359(11) . ?
C28 H28 0.9500 . ?
C29 C30 1.396(10) . ?
C29 H29 0.9500 . ?
C30 C37 1.502(10) . ?
C31 C32 1.422(9) . ?
C33 C34 1.518(10) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.543(11) . ?
C34 H34 1.0000 . ?
C35 C36 1.533(13) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.533(9) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.519(9) . ?
C38 H38 1.0000 . ?
C39 C40 1.518(9) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
S1 O7 1.424(5) . ?
S1 O6 1.431(5) . ?
S1 O5 1.452(5) . ?
S1 C41 1.815(9) . ?
C41 F3 1.332(9) . ?
C41 F2 1.337(9) . ?
C41 F1 1.341(9) . ?
S2 O9 1.413(6) . ?
S2 O10 1.451(7) . ?
S2 O8 1.454(6) . ?
S2 C42 1.790(10) . ?
C42 F10 1.307(12) . ?
C42 F11 1.317(14) . ?
C42 F12 1.347(11) . ?
F4 C43 1.317(9) . ?
F5 C43 1.329(9) . ?
F6 C43 1.330(8) . ?
S3 O13 1.428(5) . ?
S3 O11 1.448(5) . ?
S3 O12 1.458(5) . ?
S3 C43 1.826(8) . ?
F7 C44 1.330(9) . ?
F8 C44 1.320(9) . ?
F9 C44 1.321(9) . ?
S4 O15 1.428(5) . ?
S4 O14 1.447(5) . ?
S4 O16 1.447(5) . ?
S4 C44 1.822(9) . ?
