#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/24/2222430.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222430
loop_
_publ_author_name
'Soleimannejad, Janet'
'Aghabozorg, Hossein'
'Manteghi, Faranak'
'Najafi, Shokoh'
_publ_section_title
;(2,9-Dimethyl-1,10-phenanthroline)(4-hydroxypyridine-2,6-dicarboxylato)copper(II)
 trihydrate
;
_journal_coeditor_code           PV2164
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m761
_journal_page_last               m762
_journal_paper_doi               10.1107/S1600536809021588
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C7 H3 N O5) (C14 H12 N2)], 3H2 O'
_chemical_formula_moiety         'C21 H15 Cu N3 O5, 3(H2 O)'
_chemical_formula_sum            'C21 H21 Cu N3 O8'
_chemical_formula_weight         506.95
_chemical_name_systematic
;
(2,9-Dimethyl-1,10-phenanthroline)(4-hydroxypyridine-2,6-
dicarboxylato)copper(II) trihydrate
;
_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                91.1930(10)
_cell_angle_beta                 106.8360(10)
_cell_angle_gamma                109.2630(10)
_cell_formula_units_Z            4
_cell_length_a                   10.0212(2)
_cell_length_b                   14.8645(3)
_cell_length_c                   15.4418(3)
_cell_measurement_reflns_used    10056
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.26
_cell_measurement_theta_min      2.25
_cell_volume                     2061.05(7)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            46562
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.68
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_T_max  0.8416
_exptl_absorpt_correction_T_min  0.8243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.875
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         12549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0696P)²+0.1969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                9400
_reflns_number_total             12549
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2164.cif
_cod_data_source_block           I
_cod_database_code               2222430
_cod_database_fobs_code          2222430
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.18000(3) 0.776157(17) 0.315608(16) 0.01236(7) Uani d . 1 . .
Cu Cu2 0.89377(3) 0.750300(18) 0.759838(16) 0.01373(7) Uani d . 1 . .
O O1 -0.02604(16) 0.67332(11) 0.27155(10) 0.0178(3) Uani d . 1 . .
O O2 -0.17402(17) 0.56098(11) 0.15312(10) 0.0217(3) Uani d . 1 . .
O O3 0.15699(18) 0.65953(12) -0.06028(10) 0.0229(3) Uani d . 1 . .
H H3C 0.2339 0.6929 -0.0720 0.034 Uiso calc R 1 . .
O O4 0.51539(17) 0.92317(11) 0.22333(11) 0.0221(3) Uani d . 1 . .
O O5 0.36783(16) 0.88012(10) 0.31126(9) 0.0150(3) Uani d . 1 . .
O O6 1.10226(17) 0.84891(11) 0.79318(10) 0.0186(3) Uani d . 1 . .
O O7 1.27334(17) 0.95980(12) 0.90676(10) 0.0214(3) Uani d . 1 . .
O O8 0.95793(17) 0.90993(11) 1.13195(10) 0.0196(3) Uani d . 1 . .
H H8C 0.8778 0.8871 1.1441 0.029 Uiso calc R 1 . .
O O9 0.57249(17) 0.62956(11) 0.87302(10) 0.0206(3) Uani d . 1 . .
O O10 0.70852(16) 0.65093(11) 0.77791(10) 0.0169(3) Uani d . 1 . .
N N1 0.17688(18) 0.82702(12) 0.43438(11) 0.0115(3) Uani d . 1 . .
N N2 0.28176(19) 0.68645(12) 0.40714(11) 0.0139(3) Uani d . 1 . .
N N3 0.16794(19) 0.74652(12) 0.19294(11) 0.0128(3) Uani d . 1 . .
N N4 0.75691(19) 0.81640(12) 0.65962(11) 0.0140(3) Uani d . 1 . .
N N5 0.89303(19) 0.68955(12) 0.64437(11) 0.0133(3) Uani d . 1 . .
N N6 0.91937(19) 0.79431(12) 0.88159(11) 0.0125(3) Uani d . 1 . .
C C1 0.3294(2) 0.61610(15) 0.39115(14) 0.0163(4) Uani d . 1 . .
C C2 0.3859(3) 0.56796(17) 0.46299(15) 0.0220(5) Uani d . 1 . .
H H2 0.4153 0.5160 0.4500 0.026 Uiso calc R 1 . .
C C3 0.3985(3) 0.59535(17) 0.55083(15) 0.0220(5) Uani d . 1 . .
H H3 0.4387 0.5637 0.5990 0.026 Uiso calc R 1 . .
C C4 0.3513(2) 0.67093(15) 0.56916(14) 0.0158(4) Uani d . 1 . .
C C5 0.3611(2) 0.70513(16) 0.65927(14) 0.0191(4) Uani d . 1 . .
H H5 0.4016 0.6764 0.7099 0.023 Uiso calc R 1 . .
C C6 0.3133(2) 0.77814(16) 0.67294(14) 0.0174(4) Uani d . 1 . .
H H6 0.3218 0.8005 0.7331 0.021 Uiso calc R 1 . .
C C7 0.2502(2) 0.82174(15) 0.59763(13) 0.0151(4) Uani d . 1 . .
C C8 0.1995(2) 0.89834(15) 0.60858(14) 0.0164(4) Uani d . 1 . .
H H8 0.2080 0.9241 0.6676 0.020 Uiso calc R 1 . .
C C9 0.1379(2) 0.93450(15) 0.53255(14) 0.0164(4) Uani d . 1 . .
H H9 0.1034 0.9858 0.5390 0.020 Uiso calc R 1 . .
C C10 0.1248(2) 0.89678(14) 0.44484(13) 0.0133(4) Uani d . 1 . .
C C11 0.2379(2) 0.78919(14) 0.50869(13) 0.0125(4) Uani d . 1 . .
C C12 0.2918(2) 0.71320(15) 0.49419(13) 0.0137(4) Uani d . 1 . .
C C13 0.0502(2) 0.93156(15) 0.36039(14) 0.0154(4) Uani d . 1 . .
H H13A 0.1012 0.9314 0.3151 0.023 Uiso calc R 1 . .
H H13B 0.0545 0.9970 0.3755 0.023 Uiso calc R 1 . .
H H13C -0.0541 0.8890 0.3354 0.023 Uiso calc R 1 . .
C C14 0.3228(3) 0.58905(17) 0.29559(15) 0.0211(5) Uani d . 1 . .
H H14A 0.2223 0.5775 0.2542 0.032 Uiso calc R 1 . .
H H14B 0.3469 0.5306 0.2926 0.032 Uiso calc R 1 . .
H H14C 0.3948 0.6414 0.2775 0.032 Uiso calc R 1 . .
C C15 -0.0619(2) 0.63130(15) 0.19051(14) 0.0153(4) Uani d . 1 . .
C C16 0.0507(2) 0.67360(15) 0.14055(13) 0.0141(4) Uani d . 1 . .
C C17 0.0453(2) 0.64275(15) 0.05485(14) 0.0162(4) Uani d . 1 . .
H H17 -0.0378 0.5905 0.0178 0.019 Uiso calc R 1 . .
C C18 0.1649(2) 0.68981(16) 0.02292(14) 0.0172(4) Uani d . 1 . .
C C19 0.2855(2) 0.76720(15) 0.07962(14) 0.0162(4) Uani d . 1 . .
H H19 0.3673 0.8008 0.0595 0.019 Uiso calc R 1 . .
C C20 0.2825(2) 0.79327(14) 0.16487(13) 0.0130(4) Uani d . 1 . .
C C21 0.4010(2) 0.87260(15) 0.23753(14) 0.0151(4) Uani d . 1 . .
C C22 0.6861(2) 0.87632(14) 0.66901(14) 0.0137(4) Uani d . 1 . .
C C23 0.6090(2) 0.91006(15) 0.59242(14) 0.0162(4) Uani d . 1 . .
H H23 0.5584 0.9520 0.6004 0.019 Uiso calc R 1 . .
C C24 0.6071(2) 0.88225(15) 0.50639(14) 0.0161(4) Uani d . 1 . .
H H24 0.5564 0.9055 0.4549 0.019 Uiso calc R 1 . .
C C25 0.6811(2) 0.81892(15) 0.49529(14) 0.0145(4) Uani d . 1 . .
C C26 0.6880(2) 0.78837(15) 0.40854(13) 0.0160(4) Uani d . 1 . .
H H26 0.6412 0.8111 0.3553 0.019 Uiso calc R 1 . .
C C27 0.7608(2) 0.72721(15) 0.40165(13) 0.0160(4) Uani d . 1 . .
H H27 0.7655 0.7083 0.3438 0.019 Uiso calc R 1 . .
C C28 0.8305(2) 0.69104(15) 0.48090(13) 0.0143(4) Uani d . 1 . .
C C29 0.9066(2) 0.62694(15) 0.47755(14) 0.0164(4) Uani d . 1 . .
H H29 0.9132 0.6054 0.4211 0.020 Uiso calc R 1 . .
C C30 0.9709(2) 0.59608(15) 0.55649(14) 0.0164(4) Uani d . 1 . .
H H30 1.0218 0.5527 0.5545 0.020 Uiso calc R 1 . .
C C31 0.9624(2) 0.62803(14) 0.64040(14) 0.0147(4) Uani d . 1 . .
C C32 0.8278(2) 0.72104(14) 0.56680(13) 0.0125(4) Uani d . 1 . .
C C33 0.7531(2) 0.78780(14) 0.57459(13) 0.0127(4) Uani d . 1 . .
C C34 1.0325(3) 0.59555(16) 0.72729(14) 0.0188(4) Uani d . 1 . .
H H34A 1.1303 0.6440 0.7588 0.028 Uiso calc R 1 . .
H H34B 1.0442 0.5344 0.7136 0.028 Uiso calc R 1 . .
H H34C 0.9688 0.5869 0.7664 0.028 Uiso calc R 1 . .
C C35 0.6941(3) 0.90849(16) 0.76295(14) 0.0191(4) Uani d . 1 . .
H H35A 0.6582 0.8522 0.7931 0.029 Uiso calc R 1 . .
H H35B 0.6318 0.9480 0.7597 0.029 Uiso calc R 1 . .
H H35C 0.7974 0.9464 0.7979 0.029 Uiso calc R 1 . .
C C35A 1.1514(2) 0.89664(15) 0.87318(14) 0.0157(4) Uani d . 1 . .
C C36 1.0421(2) 0.86719(14) 0.92753(13) 0.0133(4) Uani d . 1 . .
C C37 1.0587(2) 0.90636(15) 1.01326(13) 0.0146(4) Uani d . 1 . .
H H37 1.1471 0.9575 1.0465 0.018 Uiso calc R 1 . .
C C38 0.9421(2) 0.86912(15) 1.05067(13) 0.0147(4) Uani d . 1 . .
C C39 0.8153(2) 0.79024(15) 1.00122(14) 0.0145(4) Uani d . 1 . .
H H39 0.7363 0.7624 1.0256 0.017 Uiso calc R 1 . .
C C40 0.8096(2) 0.75499(14) 0.91681(13) 0.0128(4) Uani d . 1 . .
C C41 0.6861(2) 0.67159(15) 0.85124(14) 0.0155(4) Uani d . 1 . .
O O1S -0.36552(18) 0.52690(11) 0.25879(11) 0.0233(3) Uani d . 1 . .
H H1B -0.4325 0.4749 0.2290 0.028 Uiso d R 1 . .
H H1A -0.2950 0.5259 0.2391 0.028 Uiso d R 1 . .
O O2S 0.72446(18) 0.85157(12) 1.18104(11) 0.0242(4) Uani d . 1 . .
H H2A 0.6820 0.8915 1.1861 0.029 Uiso d R 1 . .
H H2B 0.6744 0.7933 1.1823 0.029 Uiso d R 1 . .
O O3S 0.40048(19) 0.73524(13) -0.09847(11) 0.0281(4) Uani d . 1 . .
H H3B 0.4591 0.7047 -0.0971 0.034 Uiso d R 1 . .
H H3A 0.4522 0.7936 -0.0772 0.034 Uiso d R 1 . .
O O4S 0.3462(3) 0.52186(14) 0.02695(14) 0.0551(7) Uani d . 1 . .
H H4A 0.3905 0.4814 0.0346 0.066 Uiso d R 1 . .
H H4B 0.2978 0.5028 -0.0292 0.066 Uiso d R 1 . .
O O5S 0.55325(19) 0.92630(12) -0.07300(11) 0.0282(4) Uani d . 1 . .
H H5B 0.6076 0.9614 -0.0227 0.034 Uiso d R 1 . .
H H5A 0.4795 0.9447 -0.0935 0.034 Uiso d R 1 . .
O O6S 0.5503(2) 0.66922(13) 0.16038(13) 0.0351(4) Uani d . 1 . .
H H6A 0.4896 0.6346 0.1111 0.042 Uiso d R 1 . .
H H6B 0.5865 0.6312 0.1911 0.042 Uiso d R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Cu1 N1 . . 168.68(7) ?
N3 Cu1 O5 . . 80.32(7) ?
N1 Cu1 O5 . . 97.54(6) ?
N3 Cu1 O1 . . 80.62(7) ?
N1 Cu1 O1 . . 99.73(6) ?
O5 Cu1 O1 . . 159.59(6) ?
N3 Cu1 N2 . . 111.53(7) ?
N1 Cu1 N2 . . 79.77(6) ?
O5 Cu1 N2 . . 99.28(6) ?
O1 Cu1 N2 . . 94.45(6) ?
N6 Cu2 N5 . . 168.36(7) ?
N6 Cu2 O6 . . 80.28(7) ?
N5 Cu2 O6 . . 96.98(7) ?
N6 Cu2 O10 . . 80.35(7) ?
N5 Cu2 O10 . . 100.13(7) ?
O6 Cu2 O10 . . 158.49(6) ?
N6 Cu2 N4 . . 111.71(7) ?
N5 Cu2 N4 . . 79.92(7) ?
O6 Cu2 N4 . . 103.56(6) ?
O10 Cu2 N4 . . 92.23(6) ?
C15 O1 Cu1 . . 114.37(13) ?
C18 O3 H3C . . 109.5 ?
C21 O5 Cu1 . . 114.81(13) ?
C35A O6 Cu2 . . 115.27(13) ?
C38 O8 H8C . . 109.5 ?
C41 O10 Cu2 . . 113.04(13) ?
C10 N1 C11 . . 119.81(17) ?
C10 N1 Cu1 . . 123.96(13) ?
C11 N1 Cu1 . . 116.18(13) ?
C1 N2 C12 . . 118.95(17) ?
C1 N2 Cu1 . . 132.37(14) ?
C12 N2 Cu1 . . 108.69(13) ?
C20 N3 C16 . . 122.35(18) ?
C20 N3 Cu1 . . 118.70(14) ?
C16 N3 Cu1 . . 118.67(14) ?
C22 N4 C33 . . 118.74(17) ?
C22 N4 Cu2 . . 132.73(14) ?
C33 N4 Cu2 . . 108.52(13) ?
C31 N5 C32 . . 120.07(17) ?
C31 N5 Cu2 . . 123.70(14) ?
C32 N5 Cu2 . . 115.96(13) ?
C36 N6 C40 . . 121.98(17) ?
C36 N6 Cu2 . . 119.09(14) ?
C40 N6 Cu2 . . 118.81(14) ?
N2 C1 C2 . . 120.68(19) ?
N2 C1 C14 . . 118.75(18) ?
C2 C1 C14 . . 120.56(19) ?
C3 C2 C1 . . 120.7(2) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 119.2(2) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C12 C4 C3 . . 116.91(19) ?
C12 C4 C5 . . 119.85(18) ?
C3 C4 C5 . . 123.25(19) ?
C6 C5 C4 . . 120.74(19) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C7 . . 120.63(19) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C11 C7 C8 . . 117.47(18) ?
C11 C7 C6 . . 119.89(18) ?
C8 C7 C6 . . 122.64(18) ?
C9 C8 C7 . . 118.74(18) ?
C9 C8 H8 . . 120.6 ?
C7 C8 H8 . . 120.6 ?
C8 C9 C10 . . 121.01(19) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
N1 C10 C9 . . 120.49(18) ?
N1 C10 C13 . . 117.63(17) ?
C9 C10 C13 . . 121.87(18) ?
N1 C11 C7 . . 122.41(18) ?
N1 C11 C12 . . 117.98(17) ?
C7 C11 C12 . . 119.60(18) ?
N2 C12 C4 . . 123.42(18) ?
N2 C12 C11 . . 117.32(17) ?
C4 C12 C11 . . 119.27(18) ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C1 C14 H14A . . 109.5 ?
C1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O2 C15 O1 . . 125.8(2) ?
O2 C15 C16 . . 119.72(18) ?
O1 C15 C16 . . 114.46(18) ?
N3 C16 C17 . . 120.63(19) ?
N3 C16 C15 . . 111.38(17) ?
C17 C16 C15 . . 127.92(19) ?
C16 C17 C18 . . 118.77(19) ?
C16 C17 H17 . . 120.6 ?
C18 C17 H17 . . 120.6 ?
O3 C18 C17 . . 117.9(2) ?
O3 C18 C19 . . 123.2(2) ?
C17 C18 C19 . . 118.94(19) ?
C20 C19 C18 . . 118.6(2) ?
C20 C19 H19 . . 120.7 ?
C18 C19 H19 . . 120.7 ?
N3 C20 C19 . . 120.70(19) ?
N3 C20 C21 . . 111.76(17) ?
C19 C20 C21 . . 127.53(19) ?
O4 C21 O5 . . 125.7(2) ?
O4 C21 C20 . . 120.64(18) ?
O5 C21 C20 . . 113.69(18) ?
N4 C22 C23 . . 121.14(18) ?
N4 C22 C35 . . 117.98(18) ?
C23 C22 C35 . . 120.86(18) ?
C24 C23 C22 . . 120.11(19) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 119.45(19) ?
C23 C24 H24 . . 120.3 ?
C25 C24 H24 . . 120.3 ?
C33 C25 C24 . . 116.83(18) ?
C33 C25 C26 . . 120.08(18) ?
C24 C25 C26 . . 123.07(18) ?
C27 C26 C25 . . 120.69(19) ?
C27 C26 H26 . . 119.7 ?
C25 C26 H26 . . 119.7 ?
C26 C27 C28 . . 120.59(19) ?
C26 C27 H27 . . 119.7 ?
C28 C27 H27 . . 119.7 ?
C32 C28 C29 . . 117.11(18) ?
C32 C28 C27 . . 119.93(18) ?
C29 C28 C27 . . 122.94(18) ?
C30 C29 C28 . . 119.35(19) ?
C30 C29 H29 . . 120.3 ?
C28 C29 H29 . . 120.3 ?
C29 C30 C31 . . 120.65(19) ?
C29 C30 H30 . . 119.7 ?
C31 C30 H30 . . 119.7 ?
N5 C31 C30 . . 120.39(18) ?
N5 C31 C34 . . 118.18(18) ?
C30 C31 C34 . . 121.43(18) ?
N5 C32 C28 . . 122.42(18) ?
N5 C32 C33 . . 118.02(17) ?
C28 C32 C33 . . 119.56(18) ?
N4 C33 C25 . . 123.71(18) ?
N4 C33 C32 . . 117.22(17) ?
C25 C33 C32 . . 119.07(17) ?
C31 C34 H34A . . 109.5 ?
C31 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C31 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C22 C35 H35A . . 109.5 ?
C22 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C22 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
O7 C35A O6 . . 126.1(2) ?
O7 C35A C36 . . 120.32(18) ?
O6 C35A C36 . . 113.61(18) ?
N6 C36 C37 . . 120.64(19) ?
N6 C36 C35A . . 111.47(17) ?
C37 C36 C35A . . 127.89(19) ?
C36 C37 C38 . . 118.71(19) ?
C36 C37 H37 . . 120.6 ?
C38 C37 H37 . . 120.6 ?
O8 C38 C37 . . 117.86(19) ?
O8 C38 C39 . . 122.96(19) ?
C37 C38 C39 . . 119.18(18) ?
C40 C39 C38 . . 117.95(19) ?
C40 C39 H39 . . 121.0 ?
C38 C39 H39 . . 121.0 ?
N6 C40 C39 . . 121.46(19) ?
N6 C40 C41 . . 110.82(17) ?
C39 C40 C41 . . 127.72(19) ?
O9 C41 O10 . . 125.6(2) ?
O9 C41 C40 . . 118.47(18) ?
O10 C41 C40 . . 115.93(18) ?
H1B O1S H1A . . 99.2 ?
H2A O2S H2B . . 115.2 ?
H3B O3S H3A . . 108.5 ?
H4A O4S H4B . . 96.6 ?
H5B O5S H5A . . 107.1 ?
H6A O6S H6B . . 104.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N3 . 1.8959(16) ?
Cu1 N1 . 1.9818(16) ?
Cu1 O5 . 2.0234(15) ?
Cu1 O1 . 2.0306(15) ?
Cu1 N2 . 2.2263(17) ?
Cu2 N6 . 1.8940(16) ?
Cu2 N5 . 1.9787(16) ?
Cu2 O6 . 2.0257(16) ?
Cu2 O10 . 2.0528(15) ?
Cu2 N4 . 2.2281(17) ?
O1 C15 . 1.282(2) ?
O2 C15 . 1.230(3) ?
O3 C18 . 1.324(2) ?
O3 H3C . 0.8400 ?
O4 C21 . 1.229(3) ?
O5 C21 . 1.287(2) ?
O6 C35A . 1.286(2) ?
O7 C35A . 1.224(3) ?
O8 C38 . 1.326(2) ?
O8 H8C . 0.8400 ?
O9 C41 . 1.250(3) ?
O10 C41 . 1.267(2) ?
N1 C10 . 1.331(3) ?
N1 C11 . 1.362(2) ?
N2 C1 . 1.330(3) ?
N2 C12 . 1.360(3) ?
N3 C20 . 1.328(3) ?
N3 C16 . 1.335(3) ?
N4 C22 . 1.338(3) ?
N4 C33 . 1.358(2) ?
N5 C31 . 1.328(3) ?
N5 C32 . 1.361(2) ?
N6 C36 . 1.332(3) ?
N6 C40 . 1.336(3) ?
C1 C2 . 1.414(3) ?
C1 C14 . 1.498(3) ?
C2 C3 . 1.366(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.407(3) ?
C3 H3 . 0.9500 ?
C4 C12 . 1.403(3) ?
C4 C5 . 1.436(3) ?
C5 C6 . 1.358(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.431(3) ?
C6 H6 . 0.9500 ?
C7 C11 . 1.404(3) ?
C7 C8 . 1.417(3) ?
C8 C9 . 1.369(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.408(3) ?
C9 H9 . 0.9500 ?
C10 C13 . 1.499(3) ?
C11 C12 . 1.442(3) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 C16 . 1.523(3) ?
C16 C17 . 1.372(3) ?
C17 C18 . 1.404(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.407(3) ?
C19 C20 . 1.376(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.519(3) ?
C22 C23 . 1.414(3) ?
C22 C35 . 1.489(3) ?
C23 C24 . 1.376(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.412(3) ?
C24 H24 . 0.9500 ?
C25 C33 . 1.402(3) ?
C25 C26 . 1.433(3) ?
C26 C27 . 1.360(3) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.433(3) ?
C27 H27 . 0.9500 ?
C28 C32 . 1.401(3) ?
C28 C29 . 1.412(3) ?
C29 C30 . 1.369(3) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.406(3) ?
C30 H30 . 0.9500 ?
C31 C34 . 1.494(3) ?
C32 C33 . 1.448(3) ?
C34 H34A . 0.9800 ?
C34 H34B . 0.9800 ?
C34 H34C . 0.9800 ?
C35 H35A . 0.9800 ?
C35 H35B . 0.9800 ?
C35 H35C . 0.9800 ?
C35A C36 . 1.525(3) ?
C36 C37 . 1.377(3) ?
C37 C38 . 1.408(3) ?
C37 H37 . 0.9500 ?
C38 C39 . 1.411(3) ?
C39 C40 . 1.373(3) ?
C39 H39 . 0.9500 ?
C40 C41 . 1.517(3) ?
O1S H1B . 0.8500 ?
O1S H1A . 0.8500 ?
O2S H2A . 0.8500 ?
O2S H2B . 0.8500 ?
O3S H3B . 0.8500 ?
O3S H3A . 0.8500 ?
O4S H4A . 0.8500 ?
O4S H4B . 0.8500 ?
O5S H5B . 0.8501 ?
O5S H5A . 0.8501 ?
O6S H6A . 0.8500 ?
O6S H6B . 0.8501 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3C O3S . 0.84 1.75 2.572(2) 165.9
O8 H8C O2S . 0.84 1.72 2.553(2) 172.6
O1S H1B O9 2_566 0.85 2.01 2.833(2) 162.6
O1S H1A O2 . 0.85 2.01 2.794(2) 152.5
O2S H2A O4 1_556 0.85 2.10 2.861(2) 148.9
O2S H2A O7 2_777 0.85 2.64 3.136(2) 118.2
O2S H2B O6S 1_556 0.85 1.81 2.649(2) 168.2
O3S H3B O9 1_554 0.85 1.97 2.798(2) 165.8
O3S H3A O5S . 0.85 1.89 2.702(2) 160.3
O4S H4A O9 2_666 0.85 2.26 2.957(3) 139.9
O4S H4B O2 2_565 0.85 1.97 2.811(2) 171.2
O5S H5B O7 2_776 0.85 1.94 2.787(2) 178.4
O5S H5A O7 1_454 0.85 2.15 2.938(2) 153.8
O6S H6A O4S . 0.85 1.95 2.764(3) 160.2
O6S H6B O1S 1_655 0.85 2.00 2.840(2) 170.0
C13 H13B Cg1 2_676 0.98 2.76 3.372(2) 121
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N3 Cu1 O1 C15 . . . . 6.39(14) ?
N1 Cu1 O1 C15 . . . . 174.92(14) ?
O5 Cu1 O1 C15 . . . . 27.6(3) ?
N2 Cu1 O1 C15 . . . . -104.72(15) ?
N3 Cu1 O5 C21 . . . . -7.58(14) ?
N1 Cu1 O5 C21 . . . . -176.34(14) ?
O1 Cu1 O5 C21 . . . . -28.8(3) ?
N2 Cu1 O5 C21 . . . . 102.87(14) ?
N6 Cu2 O6 C35A . . . . -3.25(15) ?
N5 Cu2 O6 C35A . . . . -171.81(15) ?
O10 Cu2 O6 C35A . . . . -29.3(3) ?
N4 Cu2 O6 C35A . . . . 106.93(15) ?
N6 Cu2 O10 C41 . . . . 9.37(14) ?
N5 Cu2 O10 C41 . . . . 177.56(14) ?
O6 Cu2 O10 C41 . . . . 35.4(2) ?
N4 Cu2 O10 C41 . . . . -102.29(14) ?
N3 Cu1 N1 C10 . . . . 3.2(5) ?
O5 Cu1 N1 C10 . . . . 81.50(16) ?
O1 Cu1 N1 C10 . . . . -87.56(16) ?
N2 Cu1 N1 C10 . . . . 179.63(17) ?
N3 Cu1 N1 C11 . . . . -174.1(3) ?
O5 Cu1 N1 C11 . . . . -95.83(14) ?
O1 Cu1 N1 C11 . . . . 95.11(14) ?
N2 Cu1 N1 C11 . . . . 2.30(14) ?
N3 Cu1 N2 C1 . . . . -2.5(2) ?
N1 Cu1 N2 C1 . . . . 178.3(2) ?
O5 Cu1 N2 C1 . . . . -85.68(19) ?
O1 Cu1 N2 C1 . . . . 79.16(19) ?
N3 Cu1 N2 C12 . . . . 178.01(13) ?
N1 Cu1 N2 C12 . . . . -1.23(13) ?
O5 Cu1 N2 C12 . . . . 94.83(14) ?
O1 Cu1 N2 C12 . . . . -100.33(14) ?
N1 Cu1 N3 C20 . . . . 87.4(4) ?
O5 Cu1 N3 C20 . . . . 7.40(14) ?
O1 Cu1 N3 C20 . . . . -179.94(16) ?
N2 Cu1 N3 C20 . . . . -88.83(15) ?
N1 Cu1 N3 C16 . . . . -98.6(4) ?
O5 Cu1 N3 C16 . . . . -178.60(16) ?
O1 Cu1 N3 C16 . . . . -5.94(15) ?
N2 Cu1 N3 C16 . . . . 85.17(16) ?
N6 Cu2 N4 C22 . . . . -3.4(2) ?
N5 Cu2 N4 C22 . . . . 177.0(2) ?
O6 Cu2 N4 C22 . . . . -88.16(19) ?
O10 Cu2 N4 C22 . . . . 77.12(19) ?
N6 Cu2 N4 C33 . . . . 175.18(13) ?
N5 Cu2 N4 C33 . . . . -4.43(13) ?
O6 Cu2 N4 C33 . . . . 90.39(14) ?
O10 Cu2 N4 C33 . . . . -104.33(13) ?
N6 Cu2 N5 C31 . . . . 1.4(5) ?
O6 Cu2 N5 C31 . . . . 76.98(17) ?
O10 Cu2 N5 C31 . . . . -89.94(17) ?
N4 Cu2 N5 C31 . . . . 179.58(18) ?
N6 Cu2 N5 C32 . . . . -172.7(3) ?
O6 Cu2 N5 C32 . . . . -97.06(15) ?
O10 Cu2 N5 C32 . . . . 96.02(15) ?
N4 Cu2 N5 C32 . . . . 5.54(14) ?
N5 Cu2 N6 C36 . . . . 82.3(4) ?
O6 Cu2 N6 C36 . . . . 5.06(14) ?
O10 Cu2 N6 C36 . . . . 175.67(16) ?
N4 Cu2 N6 C36 . . . . -95.77(15) ?
N5 Cu2 N6 C40 . . . . -101.6(4) ?
O6 Cu2 N6 C40 . . . . -178.89(16) ?
O10 Cu2 N6 C40 . . . . -8.27(14) ?
N4 Cu2 N6 C40 . . . . 80.28(16) ?
C12 N2 C1 C2 . . . . 1.7(3) ?
Cu1 N2 C1 C2 . . . . -177.74(16) ?
C12 N2 C1 C14 . . . . -178.02(19) ?
Cu1 N2 C1 C14 . . . . 2.5(3) ?
N2 C1 C2 C3 . . . . -2.8(3) ?
C14 C1 C2 C3 . . . . 176.9(2) ?
C1 C2 C3 C4 . . . . 1.5(4) ?
C2 C3 C4 C12 . . . . 0.7(3) ?
C2 C3 C4 C5 . . . . -179.6(2) ?
C12 C4 C5 C6 . . . . 0.0(3) ?
C3 C4 C5 C6 . . . . -179.7(2) ?
C4 C5 C6 C7 . . . . 0.8(3) ?
C5 C6 C7 C11 . . . . -0.2(3) ?
C5 C6 C7 C8 . . . . -179.7(2) ?
C11 C7 C8 C9 . . . . 1.8(3) ?
C6 C7 C8 C9 . . . . -178.7(2) ?
C7 C8 C9 C10 . . . . 0.0(3) ?
C11 N1 C10 C9 . . . . 2.6(3) ?
Cu1 N1 C10 C9 . . . . -174.66(15) ?
C11 N1 C10 C13 . . . . -176.24(18) ?
Cu1 N1 C10 C13 . . . . 6.5(3) ?
C8 C9 C10 N1 . . . . -2.2(3) ?
C8 C9 C10 C13 . . . . 176.5(2) ?
C10 N1 C11 C7 . . . . -0.7(3) ?
Cu1 N1 C11 C7 . . . . 176.72(15) ?
C10 N1 C11 C12 . . . . 179.48(18) ?
Cu1 N1 C11 C12 . . . . -3.1(2) ?
C8 C7 C11 N1 . . . . -1.5(3) ?
C6 C7 C11 N1 . . . . 178.99(19) ?
C8 C7 C11 C12 . . . . 178.31(19) ?
C6 C7 C11 C12 . . . . -1.2(3) ?
C1 N2 C12 C4 . . . . 0.6(3) ?
Cu1 N2 C12 C4 . . . . -179.87(16) ?
C1 N2 C12 C11 . . . . -179.53(18) ?
Cu1 N2 C12 C11 . . . . 0.0(2) ?
C3 C4 C12 N2 . . . . -1.8(3) ?
C5 C4 C12 N2 . . . . 178.5(2) ?
C3 C4 C12 C11 . . . . 178.3(2) ?
C5 C4 C12 C11 . . . . -1.4(3) ?
N1 C11 C12 N2 . . . . 1.9(3) ?
C7 C11 C12 N2 . . . . -177.88(18) ?
N1 C11 C12 C4 . . . . -178.17(18) ?
C7 C11 C12 C4 . . . . 2.0(3) ?
Cu1 O1 C15 O2 . . . . 172.45(17) ?
Cu1 O1 C15 C16 . . . . -5.7(2) ?
C20 N3 C16 C17 . . . . 1.1(3) ?
Cu1 N3 C16 C17 . . . . -172.68(15) ?
C20 N3 C16 C15 . . . . 178.32(17) ?
Cu1 N3 C16 C15 . . . . 4.5(2) ?
O2 C15 C16 N3 . . . . -177.16(18) ?
O1 C15 C16 N3 . . . . 1.1(3) ?
O2 C15 C16 C17 . . . . -0.2(3) ?
O1 C15 C16 C17 . . . . 178.1(2) ?
N3 C16 C17 C18 . . . . -0.5(3) ?
C15 C16 C17 C18 . . . . -177.25(19) ?
C16 C17 C18 O3 . . . . -179.41(19) ?
C16 C17 C18 C19 . . . . -0.3(3) ?
O3 C18 C19 C20 . . . . 179.71(19) ?
C17 C18 C19 C20 . . . . 0.7(3) ?
C16 N3 C20 C19 . . . . -0.7(3) ?
Cu1 N3 C20 C19 . . . . 173.04(15) ?
C16 N3 C20 C21 . . . . -179.77(17) ?
Cu1 N3 C20 C21 . . . . -6.0(2) ?
C18 C19 C20 N3 . . . . -0.2(3) ?
C18 C19 C20 C21 . . . . 178.70(19) ?
Cu1 O5 C21 O4 . . . . -174.05(17) ?
Cu1 O5 C21 C20 . . . . 6.4(2) ?
N3 C20 C21 O4 . . . . 179.77(18) ?
C19 C20 C21 O4 . . . . 0.8(3) ?
N3 C20 C21 O5 . . . . -0.7(2) ?
C19 C20 C21 O5 . . . . -179.62(19) ?
C33 N4 C22 C23 . . . . -0.3(3) ?
Cu2 N4 C22 C23 . . . . 178.15(15) ?
C33 N4 C22 C35 . . . . -178.77(18) ?
Cu2 N4 C22 C35 . . . . -0.3(3) ?
N4 C22 C23 C24 . . . . -0.7(3) ?
C35 C22 C23 C24 . . . . 177.7(2) ?
C22 C23 C24 C25 . . . . 0.8(3) ?
C23 C24 C25 C33 . . . . 0.1(3) ?
C23 C24 C25 C26 . . . . -178.3(2) ?
C33 C25 C26 C27 . . . . 1.7(3) ?
C24 C25 C26 C27 . . . . 180.0(2) ?
C25 C26 C27 C28 . . . . 0.8(3) ?
C26 C27 C28 C32 . . . . -2.0(3) ?
C26 C27 C28 C29 . . . . 179.6(2) ?
C32 C28 C29 C30 . . . . 1.2(3) ?
C27 C28 C29 C30 . . . . 179.7(2) ?
C28 C29 C30 C31 . . . . -0.4(3) ?
C32 N5 C31 C30 . . . . 0.9(3) ?
Cu2 N5 C31 C30 . . . . -172.86(15) ?
C32 N5 C31 C34 . . . . 179.94(19) ?
Cu2 N5 C31 C34 . . . . 6.1(3) ?
C29 C30 C31 N5 . . . . -0.7(3) ?
C29 C30 C31 C34 . . . . -179.7(2) ?
C31 N5 C32 C28 . . . . -0.1(3) ?
Cu2 N5 C32 C28 . . . . 174.19(15) ?
C31 N5 C32 C33 . . . . 179.80(19) ?
Cu2 N5 C32 C33 . . . . -5.9(2) ?
C29 C28 C32 N5 . . . . -1.0(3) ?
C27 C28 C32 N5 . . . . -179.53(18) ?
C29 C28 C32 C33 . . . . 179.15(19) ?
C27 C28 C32 C33 . . . . 0.6(3) ?
C22 N4 C33 C25 . . . . 1.2(3) ?
Cu2 N4 C33 C25 . . . . -177.56(16) ?
C22 N4 C33 C32 . . . . -178.47(18) ?
Cu2 N4 C33 C32 . . . . 2.7(2) ?
C24 C25 C33 N4 . . . . -1.1(3) ?
C26 C25 C33 N4 . . . . 177.31(19) ?
C24 C25 C33 C32 . . . . 178.58(19) ?
C26 C25 C33 C32 . . . . -3.0(3) ?
N5 C32 C33 N4 . . . . 1.7(3) ?
C28 C32 C33 N4 . . . . -178.42(18) ?
N5 C32 C33 C25 . . . . -178.02(18) ?
C28 C32 C33 C25 . . . . 1.9(3) ?
Cu2 O6 C35A O7 . . . . -179.46(18) ?
Cu2 O6 C35A C36 . . . . 1.2(2) ?
C40 N6 C36 C37 . . . . -1.5(3) ?
Cu2 N6 C36 C37 . . . . 174.45(15) ?
C40 N6 C36 C35A . . . . 178.38(17) ?
Cu2 N6 C36 C35A . . . . -5.7(2) ?
O7 C35A C36 N6 . . . . -176.72(19) ?
O6 C35A C36 N6 . . . . 2.7(2) ?
O7 C35A C36 C37 . . . . 3.1(3) ?
O6 C35A C36 C37 . . . . -177.47(19) ?
N6 C36 C37 C38 . . . . -1.2(3) ?
C35A C36 C37 C38 . . . . 178.94(19) ?
C36 C37 C38 O8 . . . . -177.71(18) ?
C36 C37 C38 C39 . . . . 2.9(3) ?
O8 C38 C39 C40 . . . . 178.69(19) ?
C37 C38 C39 C40 . . . . -1.9(3) ?
C36 N6 C40 C39 . . . . 2.5(3) ?
Cu2 N6 C40 C39 . . . . -173.44(15) ?
C36 N6 C40 C41 . . . . -178.16(17) ?
Cu2 N6 C40 C41 . . . . 5.9(2) ?
C38 C39 C40 N6 . . . . -0.7(3) ?
C38 C39 C40 C41 . . . . -179.95(19) ?
Cu2 O10 C41 O9 . . . . 171.00(17) ?
Cu2 O10 C41 C40 . . . . -8.8(2) ?
N6 C40 C41 O9 . . . . -177.29(18) ?
C39 C40 C41 O9 . . . . 2.0(3) ?
N6 C40 C41 O10 . . . . 2.5(3) ?
C39 C40 C41 O10 . . . . -178.16(19) ?
