#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:46:44 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179154 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/15/4311501.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_4311501
loop_
_publ_author_name
'Michel Meyer'
'Laurent Frémond'
'Enrique Espinosa'
'Roger Guilard'
'Zhongping Ou'
'Karl M. Kadish'
_publ_contact_author
;
  Pr. Roger Guilard,
  LIMSAG, CNRS UMR 5633, 
  Universite de Bourgogne, Faculte des Sciences, 
  6 boulevard Gabriel, 21100 Dijon, 
  France 
;
_publ_contact_author_email       Roger.Guilard@u-bourgogne.fr
_publ_contact_author_fax         '+33 3 80 39 61 17'
_publ_contact_author_phone       '+33 3 80 39 61 11'
_publ_section_title
;
 Synthesis, Characterization, and X-ray Crystal Structures of Cyclam
 Derivatives. 5. Copper(II) Binding Studies of a Pyridine-Strapped
 5,12-Dioxocyclam-Based Macrobicycle1
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5572
_journal_page_last               5587
_journal_paper_doi               10.1021/ic049518k
_journal_volume                  43
_journal_year                    2004
_chemical_formula_moiety         'C17 H23 Cu N5 O2,4(H2 O)'
_chemical_formula_sum            'C17 H31 Cu N5 O6'
_chemical_formula_weight         465.01
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 91.303(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.0210(8)
_cell_length_b                   12.1560(5)
_cell_length_c                   16.5210(6)
_cell_measurement_reflns_used    11132
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      1.96
_cell_volume                     4019.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11132
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    1.132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         5858
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0304P)²+18.5091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                4351
_reflns_number_total             5858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic049518ksi20040616_110903_2.cif
_cod_data_source_block           lf156hb
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4311501
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.609805(17) 0.10603(3) 0.64467(2) 0.01610(10) Uani 1 1 d . . .
OW1 O 0.49669(13) -0.3699(2) 0.66550(14) 0.0345(6) Uani 1 1 d D . .
HW11 H 0.4829(19) -0.2951(13) 0.6607(19) 0.041 Uiso 1 1 d D . .
HW12 H 0.5104(19) -0.383(2) 0.7198(9) 0.041 Uiso 1 1 d D . .
OW2 O 0.60396(12) 0.5108(2) 0.90514(15) 0.0354(6) Uani 1 1 d D . .
HW21 H 0.6169(17) 0.453(2) 0.8696(17) 0.042 Uiso 1 1 d D . .
HW22 H 0.5663(13) 0.548(3) 0.8815(19) 0.042 Uiso 1 1 d D . .
OW3 O 0.68154(13) -0.2610(2) 0.48298(16) 0.0370(6) Uani 1 1 d D . .
HW31 H 0.6750(19) -0.278(3) 0.4274(7) 0.044 Uiso 1 1 d D . .
HW32 H 0.6534(16) -0.307(3) 0.5138(16) 0.044 Uiso 1 1 d D . .
OW4 O 0.60391(13) 0.5795(2) 0.56024(16) 0.0400(6) Uani 1 1 d D . .
HW41 H 0.5671(12) 0.599(3) 0.5922(18) 0.048 Uiso 1 1 d D . .
HW42 H 0.5884(16) 0.546(3) 0.5119(14) 0.048 Uiso 1 1 d D . .
N1A N 0.53400(18) 0.0053(3) 0.6448(2) 0.0183(7) Uani 0.765(4) 1 d PU A 1
C2A C 0.4721(2) 0.0656(7) 0.6216(4) 0.0226(12) Uani 0.765(4) 1 d PU A 1
H2A1 H 0.4534 0.1004 0.6688 0.027 Uiso 0.765(4) 1 calc PR A 1
H2A2 H 0.4392 0.0151 0.5987 0.027 Uiso 0.765(4) 1 calc PR A 1
C3A C 0.49019(15) 0.1519(3) 0.55951(18) 0.0235(6) Uani 0.765(4) 1 d PU A 1
H3A1 H 0.5009 0.1164 0.5089 0.028 Uiso 0.765(4) 1 calc PR A 1
H3A2 H 0.4523 0.2002 0.5496 0.028 Uiso 0.765(4) 1 calc PR A 1
N4A N 0.54883(12) 0.2179(2) 0.58944(14) 0.0209(5) Uani 0.765(4) 1 d PU A 1
C5A C 0.52860(15) 0.3028(3) 0.64901(18) 0.0225(6) Uani 0.765(4) 1 d PU A 1
H5A1 H 0.4982 0.2685 0.6864 0.027 Uiso 0.765(4) 1 calc PR A 1
H5A2 H 0.5036 0.3592 0.6199 0.027 Uiso 0.765(4) 1 calc PR A 1
C6A C 0.5856(3) 0.3613(4) 0.7004(4) 0.0192(11) Uani 0.765(4) 1 d PU A 1
H6A1 H 0.6140 0.3994 0.6627 0.023 Uiso 0.765(4) 1 calc PR A 1
H6A2 H 0.5646 0.4171 0.7331 0.023 Uiso 0.765(4) 1 calc PR A 1
C7A C 0.63113(19) 0.2944(3) 0.7566(2) 0.0188(8) Uani 0.765(4) 1 d PU A 1
O7A O 0.6508(3) 0.3399(5) 0.8219(4) 0.0252(11) Uani 0.765(4) 1 d PU A 1
N8A N 0.64857(17) 0.1971(3) 0.7318(2) 0.0190(7) Uani 0.765(4) 1 d PU A 1
C9A C 0.6986(3) 0.1333(5) 0.7791(3) 0.0196(11) Uani 0.765(4) 1 d PU A 1
H9A1 H 0.7302 0.1826 0.8059 0.024 Uiso 0.765(4) 1 calc PR A 1
H9A2 H 0.6768 0.0898 0.8200 0.024 Uiso 0.765(4) 1 calc PR A 1
C10A C 0.73356(15) 0.0610(3) 0.72254(19) 0.0245(6) Uani 0.765(4) 1 d PU A 1
H10A H 0.7614 0.0094 0.7529 0.029 Uiso 0.765(4) 1 calc PR A 1
H10B H 0.7623 0.1048 0.6888 0.029 Uiso 0.765(4) 1 calc PR A 1
N11A N 0.68467(13) -0.0009(2) 0.67036(15) 0.0222(5) Uani 0.765(4) 1 d PU A 1
C12A C 0.65702(15) -0.0971(3) 0.71464(18) 0.0230(6) Uani 0.765(4) 1 d PU A 1
H12A H 0.6422 -0.0715 0.7669 0.028 Uiso 0.765(4) 1 calc PR A 1
H12B H 0.6931 -0.1488 0.7247 0.028 Uiso 0.765(4) 1 calc PR A 1
C13A C 0.5976(3) -0.1610(4) 0.6725(4) 0.0222(11) Uani 0.765(4) 1 d PU A 1
H13A H 0.6133 -0.1885 0.6212 0.027 Uiso 0.765(4) 1 calc PR A 1
H13B H 0.5880 -0.2246 0.7058 0.027 Uiso 0.765(4) 1 calc PR A 1
C14A C 0.53142(19) -0.1013(3) 0.6556(2) 0.0204(8) Uani 0.765(4) 1 d PU A 1
O14A O 0.47941(19) -0.1603(3) 0.6489(3) 0.0236(8) Uani 0.765(4) 1 d PU A 1
C15A C 0.7145(5) -0.0358(13) 0.5908(9) 0.0235(17) Uani 0.765(4) 1 d PU A 1
H15A H 0.7610 -0.0558 0.5998 0.028 Uiso 0.765(4) 1 calc PR A 1
H15B H 0.6910 -0.1002 0.5703 0.028 Uiso 0.765(4) 1 calc PR A 1
C22A C 0.5855(6) 0.2719(12) 0.5218(7) 0.0191(16) Uani 0.765(4) 1 d PU A 1
H22A H 0.6044 0.3409 0.5410 0.023 Uiso 0.765(4) 1 calc PR A 1
H22B H 0.5542 0.2885 0.4778 0.023 Uiso 0.765(4) 1 calc PR A 1
N1B N 0.5571(6) -0.0280(11) 0.6534(8) 0.0182(16) Uani 0.235(4) 1 d PU A 2
C2B C 0.5976(12) -0.1262(15) 0.6746(14) 0.023(2) Uani 0.235(4) 1 d PU A 2
H2B1 H 0.5720 -0.1743 0.7090 0.027 Uiso 0.235(4) 1 calc PR A 2
H2B2 H 0.6077 -0.1663 0.6256 0.027 Uiso 0.235(4) 1 calc PR A 2
C3B C 0.65702(15) -0.0971(3) 0.71464(18) 0.0230(6) Uani 0.235(4) 1 d PU A 2
H3B1 H 0.6883 -0.1579 0.7143 0.028 Uiso 0.235(4) 1 calc PR A 2
H3B2 H 0.6486 -0.0775 0.7704 0.028 Uiso 0.235(4) 1 calc PR A 2
N4B N 0.68467(13) -0.0009(2) 0.67036(15) 0.0222(5) Uani 0.235(4) 1 d PU A 2
C5B C 0.73356(15) 0.0610(3) 0.72254(19) 0.0245(6) Uani 0.235(4) 1 d PU A 2
H5B1 H 0.7581 0.1102 0.6879 0.029 Uiso 0.235(4) 1 calc PR A 2
H5B2 H 0.7654 0.0084 0.7449 0.029 Uiso 0.235(4) 1 calc PR A 2
C6B C 0.7034(11) 0.1380(19) 0.8021(10) 0.0181(19) Uani 0.235(4) 1 d PU A 2
H6B1 H 0.6772 0.0896 0.8356 0.022 Uiso 0.235(4) 1 calc PR A 2
H6B2 H 0.7414 0.1625 0.8348 0.022 Uiso 0.235(4) 1 calc PR A 2
C7B C 0.6616(6) 0.2366(11) 0.7815(7) 0.0182(15) Uani 0.235(4) 1 d PU A 2
O7B O 0.6626(12) 0.3155(18) 0.8341(15) 0.023(3) Uani 0.235(4) 1 d PU A 2
N8B N 0.6264(6) 0.2385(10) 0.7146(7) 0.0177(15) Uani 0.235(4) 1 d PU A 2
C9B C 0.5840(13) 0.3332(17) 0.6886(15) 0.020(2) Uani 0.235(4) 1 d PU A 2
H9B1 H 0.5720 0.3753 0.7360 0.024 Uiso 0.235(4) 1 calc PR A 2
H9B2 H 0.6097 0.3808 0.6540 0.024 Uiso 0.235(4) 1 calc PR A 2
C10B C 0.52860(15) 0.3028(3) 0.64901(18) 0.0225(6) Uani 0.235(4) 1 d PU A 2
H10C H 0.5083 0.3653 0.6214 0.027 Uiso 0.235(4) 1 calc PR A 2
H10D H 0.4966 0.2725 0.6862 0.027 Uiso 0.235(4) 1 calc PR A 2
N11B N 0.54883(12) 0.2179(2) 0.58944(14) 0.0209(5) Uani 0.235(4) 1 d PU A 2
C12B C 0.49019(15) 0.1519(3) 0.55951(18) 0.0235(6) Uani 0.235(4) 1 d PU A 2
H12C H 0.5037 0.1158 0.5101 0.028 Uiso 0.235(4) 1 calc PR A 2
H12D H 0.4554 0.2040 0.5442 0.028 Uiso 0.235(4) 1 calc PR A 2
C13B C 0.4558(11) 0.059(2) 0.6145(16) 0.0223(19) Uani 0.235(4) 1 d PU A 2
H13C H 0.4426 0.0945 0.6644 0.027 Uiso 0.235(4) 1 calc PR A 2
H13D H 0.4151 0.0361 0.5865 0.027 Uiso 0.235(4) 1 calc PR A 2
C14B C 0.4933(7) -0.0400(11) 0.6367(7) 0.0201(15) Uani 0.235(4) 1 d PU A 2
O14B O 0.4615(7) -0.1300(12) 0.6430(10) 0.0231(13) Uani 0.235(4) 1 d PU A 2
C15B C 0.727(2) -0.033(5) 0.601(3) 0.023(2) Uani 0.235(4) 1 d PU A 2
H15C H 0.7159 -0.1069 0.5829 0.027 Uiso 0.235(4) 1 calc PR A 2
H15D H 0.7736 -0.0296 0.6158 0.027 Uiso 0.235(4) 1 calc PR A 2
C22B C 0.575(2) 0.266(4) 0.510(3) 0.019(2) Uani 0.235(4) 1 d PU A 2
H22C H 0.5853 0.3437 0.5171 0.022 Uiso 0.235(4) 1 calc PR A 2
H22D H 0.5422 0.2580 0.4669 0.022 Uiso 0.235(4) 1 calc PR A 2
C16 C 0.70999(14) 0.0536(2) 0.52946(17) 0.0199(6) Uani 1 1 d . . .
N17 N 0.65794(12) 0.1201(2) 0.54061(14) 0.0179(5) Uani 1 1 d . A .
C18 C 0.64067(14) 0.2002(2) 0.49028(17) 0.0189(6) Uani 1 1 d . . .
C19 C 0.67692(15) 0.2181(3) 0.42076(17) 0.0231(6) Uani 1 1 d . A .
H19 H 0.6647 0.2728 0.3839 0.028 Uiso 1 1 calc R . .
C20 C 0.73184(15) 0.1517(3) 0.40828(18) 0.0244(6) Uani 1 1 d . . .
H20 H 0.7575 0.1634 0.3629 0.029 Uiso 1 1 calc R A .
C21 C 0.74970(15) 0.0678(3) 0.46198(18) 0.0240(6) Uani 1 1 d . A .
H21 H 0.7865 0.0232 0.4532 0.029 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'
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
N1B Cu1 N1A 18.5(3) . . ?
N1B Cu1 N8A 128.6(4) . . ?
N1A Cu1 N8A 130.42(15) . . ?
N1B Cu1 N17 114.1(4) . . ?
N1A Cu1 N17 116.46(13) . . ?
N8A Cu1 N17 113.12(12) . . ?
N1B Cu1 N8B 135.4(5) . . ?
N1A Cu1 N8B 128.5(3) . . ?
N8A Cu1 N8B 21.0(3) . . ?
N17 Cu1 N8B 110.5(3) . . ?
N1B Cu1 N11A 81.2(4) . . ?
N1A Cu1 N11A 99.76(14) . . ?
N8A Cu1 N11A 85.97(13) . . ?
N17 Cu1 N11A 82.29(10) . . ?
N8B Cu1 N11A 106.4(4) . . ?
N1B Cu1 N4A 105.8(4) . . ?
N1A Cu1 N4A 87.76(13) . . ?
N8A Cu1 N4A 100.11(13) . . ?
N17 Cu1 N4A 81.53(9) . . ?
N8B Cu1 N4A 79.1(4) . . ?
N11A Cu1 N4A 163.82(10) . . ?
C14A N1A C2A 119.3(4) . . ?
C14A N1A Cu1 130.9(3) . . ?
C2A N1A Cu1 109.6(3) . . ?
N1A C2A C3A 107.8(4) . . ?
N4A C3A C2A 110.2(3) . . ?
C5A N4A C3A 111.5(2) . . ?
C5A N4A C22A 109.5(6) . . ?
C3A N4A C22A 112.4(4) . . ?
C5A N4A Cu1 109.70(18) . . ?
C3A N4A Cu1 104.40(18) . . ?
C22A N4A Cu1 109.2(5) . . ?
N4A C5A C6A 117.6(3) . . ?
C7A C6A C5A 120.3(4) . . ?
O7A C7A N8A 125.7(4) . . ?
O7A C7A C6A 117.2(4) . . ?
N8A C7A C6A 117.0(4) . . ?
C7A N8A C9A 119.6(4) . . ?
C7A N8A Cu1 129.7(3) . . ?
C9A N8A Cu1 110.1(3) . . ?
C10A C9A N8A 107.8(3) . . ?
C9A C10A N11A 110.6(3) . . ?
C12A N11A C10A 110.9(2) . . ?
C12A N11A C15A 111.3(7) . . ?
C10A N11A C15A 112.1(4) . . ?
C12A N11A Cu1 108.97(18) . . ?
C10A N11A Cu1 105.71(18) . . ?
C15A N11A Cu1 107.6(5) . . ?
N11A C12A C13A 117.1(3) . . ?
C14A C13A C12A 119.4(3) . . ?
O14A C14A N1A 125.7(4) . . ?
O14A C14A C13A 117.0(4) . . ?
N1A C14A C13A 117.2(4) . . ?
C16 C15A N11A 111.5(10) . . ?
N4A C22A C18 112.2(9) . . ?
C14B N1B C2B 119.1(14) . . ?
C14B N1B Cu1 127.3(11) . . ?
C2B N1B Cu1 113.4(11) . . ?
O7B C7B N8B 123.9(14) . . ?
O7B C7B C6B 116.2(14) . . ?
N8B C7B C6B 119.9(13) . . ?
C7B N8B C9B 123.8(13) . . ?
C7B N8B Cu1 123.8(10) . . ?
C9B N8B Cu1 111.6(10) . . ?
O14B C14B N1B 124.5(13) . . ?
O14B C14B C13B 118.4(14) . . ?
N1B C14B C13B 117.0(14) . . ?
N17 C16 C21 119.7(3) . . ?
N17 C16 C15A 112.6(6) . . ?
C21 C16 C15A 127.5(6) . . ?
N17 C16 C15B 116.4(19) . . ?
C21 C16 C15B 123.7(19) . . ?
C15A C16 C15B 9.9(19) . . ?
C18 N17 C16 123.6(2) . . ?
C18 N17 Cu1 118.71(19) . . ?
C16 N17 Cu1 117.40(19) . . ?
N17 C18 C19 120.1(3) . . ?
N17 C18 C22A 113.1(6) . . ?
C19 C18 C22A 126.5(6) . . ?
N17 C18 C22B 116.6(19) . . ?
C19 C18 C22B 123.1(18) . . ?
C22A C18 C22B 10.2(17) . . ?
C20 C19 C18 117.6(3) . . ?
C19 C20 C21 121.7(3) . . ?
C20 C21 C16 117.2(3) . . ?
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 N1B 1.949(14) . ?
Cu1 N1A 1.950(4) . ?
Cu1 N8A 1.962(3) . ?
Cu1 N17 1.997(2) . ?
Cu1 N8B 2.006(12) . ?
Cu1 N11A 2.022(2) . ?
Cu1 N4A 2.030(2) . ?
N1A C14A 1.309(6) . ?
N1A C2A 1.482(7) . ?
C2A C3A 1.517(8) . ?
C3A N4A 1.497(4) . ?
N4A C5A 1.489(4) . ?
N4A C22A 1.503(15) . ?
C5A C6A 1.577(7) . ?
C6A C7A 1.521(8) . ?
C7A O7A 1.266(8) . ?
C7A N8A 1.302(5) . ?
N8A C9A 1.476(7) . ?
C9A C10A 1.471(7) . ?
C10A N11A 1.493(4) . ?
N11A C12A 1.492(4) . ?
N11A C15A 1.517(16) . ?
C12A C13A 1.570(7) . ?
C13A C14A 1.531(7) . ?
C14A O14A 1.267(6) . ?
C15A C16 1.487(16) . ?
C22A C18 1.508(15) . ?
N1B C14B 1.308(18) . ?
N1B C2B 1.48(2) . ?
C6B C7B 1.50(3) . ?
C7B O7B 1.29(3) . ?
C7B N8B 1.298(17) . ?
N8B C9B 1.49(3) . ?
C13B C14B 1.46(3) . ?
C14B O14B 1.27(2) . ?
C15B C16 1.60(6) . ?
C22B C18 1.58(5) . ?
C16 N17 1.335(4) . ?
C16 C21 1.395(4) . ?
N17 C18 1.321(4) . ?
C18 C19 1.390(4) . ?
C19 C20 1.383(4) . ?
C20 C21 1.393(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
OW1 HW11 O14A 0.954(10) 1.652(15) 2.586(5) 165(4) .
OW1 HW11 O14B 0.954(10) 2.071(17) 3.021(14) 174(4) .
OW1 HW12 OW1 0.946(10) 1.910(18) 2.792(5) 154(3) 2_656
OW2 HW21 O7A 0.952(10) 1.735(13) 2.673(7) 168(3) .
OW2 HW21 O7B 0.952(10) 2.00(3) 2.91(2) 158(3) .
OW2 HW22 OW1 0.953(10) 1.776(11) 2.724(3) 173(4) 2_666
OW3 HW31 O7B 0.947(10) 1.62(3) 2.57(2) 176(3) 6
OW3 HW31 O7A 0.947(10) 1.952(15) 2.883(7) 167(3) 6
OW3 HW32 OW4 0.947(10) 1.876(14) 2.810(4) 168(3) 1_545
OW4 HW41 OW1 0.947(10) 1.916(11) 2.860(4) 174(4) 1_565
OW4 HW42 OW2 0.944(10) 1.924(17) 2.788(4) 151(3) 6_565
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
N1B Cu1 N1A C14A -2.8(12) . . . . ?
N8A Cu1 N1A C14A -95.0(4) . . . . ?
N17 Cu1 N1A C14A 84.2(4) . . . . ?
N8B Cu1 N1A C14A -122.2(6) . . . . ?
N11A Cu1 N1A C14A -2.0(4) . . . . ?
N4A Cu1 N1A C14A 163.6(4) . . . . ?
N1B Cu1 N1A C2A -177.2(15) . . . . ?
N8A Cu1 N1A C2A 90.6(4) . . . . ?
N17 Cu1 N1A C2A -90.2(4) . . . . ?
N8B Cu1 N1A C2A 63.4(6) . . . . ?
N11A Cu1 N1A C2A -176.4(3) . . . . ?
N4A Cu1 N1A C2A -10.8(4) . . . . ?
C14A N1A C2A C3A -140.2(4) . . . . ?
Cu1 N1A C2A C3A 34.9(5) . . . . ?
N1A C2A C3A N4A -50.3(5) . . . . ?
C2A C3A N4A C5A -79.0(4) . . . . ?
C2A C3A N4A C22A 157.6(7) . . . . ?
C2A C3A N4A Cu1 39.4(4) . . . . ?
N1B Cu1 N4A C5A 108.2(4) . . . . ?
N1A Cu1 N4A C5A 103.8(2) . . . . ?
N8A Cu1 N4A C5A -26.9(2) . . . . ?
N17 Cu1 N4A C5A -139.0(2) . . . . ?
N8B Cu1 N4A C5A -26.1(4) . . . . ?
N11A Cu1 N4A C5A -137.9(4) . . . . ?
N1B Cu1 N4A C3A -11.4(4) . . . . ?
N1A Cu1 N4A C3A -15.83(19) . . . . ?
N8A Cu1 N4A C3A -146.53(19) . . . . ?
N17 Cu1 N4A C3A 101.35(18) . . . . ?
N8B Cu1 N4A C3A -145.7(4) . . . . ?
N11A Cu1 N4A C3A 102.5(4) . . . . ?
N1B Cu1 N4A C22A -131.8(6) . . . . ?
N1A Cu1 N4A C22A -136.2(5) . . . . ?
N8A Cu1 N4A C22A 93.1(5) . . . . ?
N17 Cu1 N4A C22A -19.1(5) . . . . ?
N8B Cu1 N4A C22A 93.9(6) . . . . ?
N11A Cu1 N4A C22A -17.9(7) . . . . ?
C3A N4A C5A C6A 166.8(3) . . . . ?
C22A N4A C5A C6A -68.1(5) . . . . ?
Cu1 N4A C5A C6A 51.7(4) . . . . ?
N4A C5A C6A C7A -61.1(6) . . . . ?
C5A C6A C7A O7A -145.4(5) . . . . ?
C5A C6A C7A N8A 37.3(6) . . . . ?
O7A C7A N8A C9A -4.0(7) . . . . ?
C6A C7A N8A C9A 173.1(4) . . . . ?
O7A C7A N8A Cu1 166.8(5) . . . . ?
C6A C7A N8A Cu1 -16.1(6) . . . . ?
N1B Cu1 N8A C7A -108.2(6) . . . . ?
N1A Cu1 N8A C7A -84.3(4) . . . . ?
N17 Cu1 N8A C7A 96.5(3) . . . . ?
N8B Cu1 N8A C7A 9.3(9) . . . . ?
N11A Cu1 N8A C7A 176.3(4) . . . . ?
N4A Cu1 N8A C7A 11.5(4) . . . . ?
N1B Cu1 N8A C9A 63.3(6) . . . . ?
N1A Cu1 N8A C9A 87.2(3) . . . . ?
N17 Cu1 N8A C9A -92.0(3) . . . . ?
N8B Cu1 N8A C9A -179.2(11) . . . . ?
N11A Cu1 N8A C9A -12.1(3) . . . . ?
N4A Cu1 N8A C9A -177.0(3) . . . . ?
C7A N8A C9A C10A -151.4(4) . . . . ?
Cu1 N8A C9A C10A 36.1(5) . . . . ?
N8A C9A C10A N11A -49.7(5) . . . . ?
C9A C10A N11A C12A -79.7(4) . . . . ?
C9A C10A N11A C15A 155.2(7) . . . . ?
C9A C10A N11A Cu1 38.2(3) . . . . ?
N1B Cu1 N11A C12A -24.7(4) . . . . ?
N1A Cu1 N11A C12A -25.0(2) . . . . ?
N8A Cu1 N11A C12A 105.4(2) . . . . ?
N17 Cu1 N11A C12A -140.6(2) . . . . ?
N8B Cu1 N11A C12A 110.2(4) . . . . ?
N4A Cu1 N11A C12A -141.7(4) . . . . ?
N1B Cu1 N11A C10A -144.0(4) . . . . ?
N1A Cu1 N11A C10A -144.2(2) . . . . ?
N8A Cu1 N11A C10A -13.90(19) . . . . ?
N17 Cu1 N11A C10A 100.10(18) . . . . ?
N8B Cu1 N11A C10A -9.1(4) . . . . ?
N4A Cu1 N11A C10A 99.0(4) . . . . ?
N1B Cu1 N11A C15A 96.1(7) . . . . ?
N1A Cu1 N11A C15A 95.8(6) . . . . ?
N8A Cu1 N11A C15A -133.8(6) . . . . ?
N17 Cu1 N11A C15A -19.8(6) . . . . ?
N8B Cu1 N11A C15A -129.0(7) . . . . ?
N4A Cu1 N11A C15A -21.0(7) . . . . ?
C10A N11A C12A C13A 171.7(3) . . . . ?
C15A N11A C12A C13A -62.8(5) . . . . ?
Cu1 N11A C12A C13A 55.7(3) . . . . ?
N11A C12A C13A C14A -62.7(5) . . . . ?
C2A N1A C14A O14A -0.8(7) . . . . ?
Cu1 N1A C14A O14A -174.7(3) . . . . ?
C2A N1A C14A C13A 175.0(4) . . . . ?
Cu1 N1A C14A C13A 1.1(6) . . . . ?
C12A C13A C14A O14A -156.0(4) . . . . ?
C12A C13A C14A N1A 27.8(6) . . . . ?
C12A N11A C15A C16 150.7(5) . . . . ?
C10A N11A C15A C16 -84.4(6) . . . . ?
Cu1 N11A C15A C16 31.4(7) . . . . ?
C5A N4A C22A C18 145.0(5) . . . . ?
C3A N4A C22A C18 -90.5(5) . . . . ?
Cu1 N4A C22A C18 24.9(6) . . . . ?
N1A Cu1 N1B C14B 6.3(8) . . . . ?
N8A Cu1 N1B C14B 109.5(12) . . . . ?
N17 Cu1 N1B C14B -95.4(12) . . . . ?
N8B Cu1 N1B C14B 82.6(14) . . . . ?
N11A Cu1 N1B C14B -172.9(12) . . . . ?
N4A Cu1 N1B C14B -7.8(13) . . . . ?
N1A Cu1 N1B C2B -179(2) . . . . ?
N8A Cu1 N1B C2B -76.2(13) . . . . ?
N17 Cu1 N1B C2B 78.9(12) . . . . ?
N8B Cu1 N1B C2B -103.1(13) . . . . ?
N11A Cu1 N1B C2B 1.5(11) . . . . ?
N4A Cu1 N1B C2B 166.5(11) . . . . ?
O7B C7B N8B C9B 2(3) . . . . ?
C6B C7B N8B C9B -179.3(16) . . . . ?
O7B C7B N8B Cu1 -166.9(17) . . . . ?
C6B C7B N8B Cu1 12.0(18) . . . . ?
N1B Cu1 N8B C7B 71.2(13) . . . . ?
N1A Cu1 N8B C7B 94.4(10) . . . . ?
N8A Cu1 N8B C7B -9.5(7) . . . . ?
N17 Cu1 N8B C7B -110.8(10) . . . . ?
N11A Cu1 N8B C7B -23.0(11) . . . . ?
N4A Cu1 N8B C7B 172.7(11) . . . . ?
N1B Cu1 N8B C9B -98.7(14) . . . . ?
N1A Cu1 N8B C9B -75.5(13) . . . . ?
N8A Cu1 N8B C9B -179.4(19) . . . . ?
N17 Cu1 N8B C9B 79.3(13) . . . . ?
N11A Cu1 N8B C9B 167.1(12) . . . . ?
N4A Cu1 N8B C9B 2.7(12) . . . . ?
C2B N1B C14B O14B 5(2) . . . . ?
Cu1 N1B C14B O14B 179.5(12) . . . . ?
C2B N1B C14B C13B -178.9(16) . . . . ?
Cu1 N1B C14B C13B -5(2) . . . . ?
N11A C15A C16 N17 -28.7(7) . . . . ?
N11A C15A C16 C21 156.6(4) . . . . ?
N11A C15A C16 C15B 86(15) . . . . ?
C21 C16 N17 C18 0.6(5) . . . . ?
C15A C16 N17 C18 -174.6(5) . . . . ?
C15B C16 N17 C18 175.4(19) . . . . ?
C21 C16 N17 Cu1 -173.2(2) . . . . ?
C15A C16 N17 Cu1 11.7(6) . . . . ?
C15B C16 N17 Cu1 1.6(19) . . . . ?
N1B Cu1 N17 C18 114.5(5) . . . . ?
N1A Cu1 N17 C18 94.2(3) . . . . ?
N8A Cu1 N17 C18 -86.5(3) . . . . ?
N8B Cu1 N17 C18 -64.0(4) . . . . ?
N11A Cu1 N17 C18 -168.7(2) . . . . ?
N4A Cu1 N17 C18 10.9(2) . . . . ?
N1B Cu1 N17 C16 -71.4(5) . . . . ?
N1A Cu1 N17 C16 -91.8(2) . . . . ?
N8A Cu1 N17 C16 87.6(2) . . . . ?
N8B Cu1 N17 C16 110.1(4) . . . . ?
N11A Cu1 N17 C16 5.3(2) . . . . ?
N4A Cu1 N17 C16 -175.0(2) . . . . ?
C16 N17 C18 C19 0.8(5) . . . . ?
Cu1 N17 C18 C19 174.5(2) . . . . ?
C16 N17 C18 C22A -172.9(5) . . . . ?
Cu1 N17 C18 C22A 0.8(5) . . . . ?
C16 N17 C18 C22B 176.5(17) . . . . ?
Cu1 N17 C18 C22B -9.8(17) . . . . ?
N4A C22A C18 N17 -17.3(7) . . . . ?
N4A C22A C18 C19 169.5(4) . . . . ?
N4A C22A C18 C22B 95(14) . . . . ?
N17 C18 C19 C20 -1.8(5) . . . . ?
C22A C18 C19 C20 170.9(5) . . . . ?
C22B C18 C19 C20 -177.3(19) . . . . ?
C18 C19 C20 C21 1.6(5) . . . . ?
C19 C20 C21 C16 -0.3(5) . . . . ?
N17 C16 C21 C20 -0.8(4) . . . . ?
C15A C16 C21 C20 173.6(6) . . . . ?
C15B C16 C21 C20 -175(2) . . . . ?
