#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/02/2220217.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_2220217
loop_
_publ_author_name
'Zhai, Cuiping'
'Yan, Feng-mei'
'Zhao, Pei-zheng'
_publ_section_title
(2,9-Dimethyl-1,10-phenanthroline-κ²N,N')bis(2-hydroxybenzoato-κO)copper(II)
_journal_coeditor_code           HG2438
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1526
_journal_page_last               m1527
_journal_paper_doi               10.1107/S1600536808036283
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C7 H5 O3)2 (C14 H12 N2)]'
_chemical_formula_moiety         'C28 H22 Cu N2 O6'
_chemical_formula_sum            'C28 H22 Cu N2 O6'
_chemical_formula_weight         546.02
_chemical_name_systematic
;
(2,9-Dimethyl-1,10-phenanthroline-
κ²N,N')bis(2-hydroxybenzoato-κO)copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 112.0230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.819(2)
_cell_length_b                   12.2576(11)
_cell_length_c                   17.9084(17)
_cell_measurement_reflns_used    3270
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      19.24
_cell_measurement_theta_min      2.44
_cell_volume                     4847.1(8)
_computing_cell_refinement
'APEX2 (Bruker, 2004) and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30637
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  0.8366
_exptl_absorpt_correction_T_min  0.7652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2248
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.448
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         8932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0450
_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)+(0.051P)²+0.2481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                5274
_reflns_number_total             8932
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2438.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4847.0(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220217
_cod_database_fobs_code          2220217
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cu Cu1 0.416752(19) 0.76816(4) 0.34347(3) 0.04372(14) Uani d . 1
Cu Cu2 0.91833(2) 0.24372(4) 0.06488(3) 0.04679(15) Uani d . 1
O O1 0.42604(14) 0.5478(3) 0.36158(18) 0.0828(10) Uani d . 1
O O2 0.37117(12) 0.6601(2) 0.26599(15) 0.0537(7) Uani d . 1
O O3 0.4003(2) 0.3447(3) 0.3513(2) 0.1039(13) Uani d . 1
H H3 0.4177 0.4014 0.3714 0.156 Uiso calc R 1
O O4 0.42450(12) 0.8580(2) 0.25824(15) 0.0525(7) Uani d . 1
O O5 0.33691(13) 0.9202(2) 0.25654(16) 0.0636(8) Uani d . 1
O O6 0.26673(13) 1.0250(3) 0.13213(18) 0.0715(8) Uani d . 1
H H6 0.2774 0.9978 0.1772 0.107 Uiso calc R 1
O O7 0.92602(13) 0.4499(2) 0.07908(17) 0.0690(8) Uani d . 1
O O8 0.85069(12) 0.3372(2) 0.06067(17) 0.0611(7) Uani d . 1
O O9 0.90651(19) 0.6548(3) 0.0833(3) 0.1015(12) Uani d . 1
H H9 0.9264 0.5995 0.0853 0.152 Uiso calc R 1
O O10 0.92554(11) 0.1888(2) 0.16999(15) 0.0540(7) Uani d . 1
O O11 0.84406(12) 0.0976(2) 0.09313(15) 0.0568(7) Uani d . 1
O O12 0.79075(13) -0.0325(2) 0.15603(18) 0.0675(8) Uani d . 1
H H12 0.7973 -0.0009 0.1198 0.101 Uiso calc R 1
N N1 0.38290(13) 0.7629(2) 0.43145(16) 0.0390(7) Uani d . 1
N N2 0.49111(13) 0.8211(2) 0.43227(17) 0.0404(7) Uani d . 1
N N3 0.90189(14) 0.1985(2) -0.05127(18) 0.0461(8) Uani d . 1
N N4 1.00369(13) 0.2094(2) 0.08003(19) 0.0456(8) Uani d . 1
C C1 0.35133(17) 0.4709(3) 0.2453(2) 0.0479(10) Uani d . 1
C C2 0.3600(2) 0.3653(4) 0.2763(3) 0.0668(12) Uani d . 1
C C3 0.3263(3) 0.2798(4) 0.2294(4) 0.0814(16) Uani d . 1
H H3A 0.3305 0.2098 0.2509 0.098 Uiso calc R 1
C C4 0.2874(2) 0.2979(4) 0.1529(4) 0.0787(15) Uani d . 1
H H4 0.2660 0.2397 0.1220 0.094 Uiso calc R 1
C C5 0.27904(19) 0.4010(4) 0.1202(3) 0.0681(12) Uani d . 1
H H5 0.2524 0.4125 0.0675 0.082 Uiso calc R 1
C C6 0.31061(17) 0.4865(3) 0.1665(2) 0.0543(10) Uani d . 1
H H6A 0.3047 0.5564 0.1448 0.065 Uiso calc R 1
C C7 0.38553(18) 0.5648(4) 0.2941(2) 0.0521(10) Uani d . 1
C C8 0.36927(17) 0.9750(3) 0.1521(2) 0.0444(9) Uani d . 1
C C9 0.3138(2) 1.0240(3) 0.1071(2) 0.0552(11) Uani d . 1
C C10 0.3058(2) 1.0737(4) 0.0339(3) 0.0713(13) Uani d . 1
H H10 0.2688 1.1055 0.0037 0.086 Uiso calc R 1
C C11 0.3519(3) 1.0761(4) 0.0061(3) 0.0842(16) Uani d . 1
H H11 0.3459 1.1088 -0.0431 0.101 Uiso calc R 1
C C12 0.4071(2) 1.0306(4) 0.0503(3) 0.0806(14) Uani d . 1
H H12A 0.4386 1.0337 0.0317 0.097 Uiso calc R 1
C C13 0.4154(2) 0.9797(3) 0.1232(2) 0.0606(11) Uani d . 1
H H13 0.4527 0.9483 0.1529 0.073 Uiso calc R 1
C C14 0.37703(19) 0.9146(3) 0.2272(2) 0.0474(10) Uani d . 1
C C15 0.32818(16) 0.7343(3) 0.4286(2) 0.0445(9) Uani d . 1
C C16 0.31365(18) 0.7396(3) 0.4971(2) 0.0535(10) Uani d . 1
H H16 0.2753 0.7183 0.4938 0.064 Uiso calc R 1
C C17 0.35443(19) 0.7751(3) 0.5680(3) 0.0545(11) Uani d . 1
H H17 0.3446 0.7770 0.6136 0.065 Uiso calc R 1
C C18 0.41203(17) 0.8093(3) 0.5725(2) 0.0452(9) Uani d . 1
C C19 0.45829(19) 0.8514(3) 0.6437(2) 0.0568(11) Uani d . 1
H H19 0.4510 0.8555 0.6912 0.068 Uiso calc R 1
C C20 0.5121(2) 0.8852(3) 0.6438(2) 0.0603(11) Uani d . 1
H H20 0.5408 0.9140 0.6905 0.072 Uiso calc R 1
C C21 0.52535(16) 0.8772(3) 0.5721(2) 0.0467(10) Uani d . 1
C C22 0.58051(18) 0.9085(3) 0.5682(2) 0.0587(11) Uani d . 1
H H22 0.6104 0.9403 0.6125 0.070 Uiso calc R 1
C C23 0.59019(17) 0.8921(3) 0.4987(2) 0.0579(11) Uani d . 1
H H23 0.6272 0.9118 0.4962 0.069 Uiso calc R 1
C C24 0.54513(16) 0.8458(3) 0.4307(2) 0.0479(10) Uani d . 1
C C25 0.48185(16) 0.8339(3) 0.5027(2) 0.0389(8) Uani d . 1
C C26 0.42421(16) 0.8003(3) 0.5022(2) 0.0374(8) Uani d . 1
C C27 0.28159(17) 0.6985(4) 0.3492(2) 0.0632(12) Uani d . 1
H H27A 0.2888 0.7348 0.3061 0.095 Uiso calc R 1
H H27B 0.2419 0.7169 0.3473 0.095 Uiso calc R 1
H H27C 0.2843 0.6210 0.3435 0.095 Uiso calc R 1
C C28 0.55725(18) 0.8220(4) 0.3559(2) 0.0657(12) Uani d . 1
H H28A 0.5362 0.7567 0.3311 0.099 Uiso calc R 1
H H28B 0.6000 0.8122 0.3698 0.099 Uiso calc R 1
H H28C 0.5433 0.8819 0.3190 0.099 Uiso calc R 1
C C29 0.83703(17) 0.5201(3) 0.0916(2) 0.0480(10) Uani d . 1
C C30 0.8550(2) 0.6281(4) 0.0941(2) 0.0621(12) Uani d . 1
C C31 0.8204(3) 0.7101(4) 0.1074(3) 0.0879(18) Uani d . 1
H H31 0.8314 0.7825 0.1055 0.105 Uiso calc R 1
C C32 0.7707(3) 0.6867(5) 0.1229(3) 0.097(2) Uani d . 1
H H32 0.7484 0.7430 0.1330 0.117 Uiso calc R 1
C C33 0.7525(2) 0.5796(5) 0.1242(3) 0.0843(16) Uani d . 1
H H33 0.7186 0.5639 0.1364 0.101 Uiso calc R 1
C C34 0.78519(19) 0.4953(4) 0.1070(2) 0.0644(12) Uani d . 1
H H34 0.7725 0.4233 0.1057 0.077 Uiso calc R 1
C C35 0.87370(19) 0.4315(3) 0.0756(2) 0.0495(10) Uani d . 1
C C36 0.87985(16) 0.0701(3) 0.2347(2) 0.0441(9) Uani d . 1
C C37 0.83292(18) -0.0038(3) 0.2274(3) 0.0509(10) Uani d . 1
C C38 0.8293(2) -0.0506(4) 0.2951(3) 0.0703(13) Uani d . 1
H H38 0.7979 -0.0984 0.2906 0.084 Uiso calc R 1
C C39 0.8722(2) -0.0267(4) 0.3695(3) 0.0769(14) Uani d . 1
H H39 0.8692 -0.0588 0.4150 0.092 Uiso calc R 1
C C40 0.9200(2) 0.0443(4) 0.3788(3) 0.0710(13) Uani d . 1
H H40 0.9492 0.0587 0.4294 0.085 Uiso calc R 1
C C41 0.92263(18) 0.0929(3) 0.3104(2) 0.0570(11) Uani d . 1
H H41 0.9537 0.1417 0.3153 0.068 Uiso calc R 1
C C42 0.88268(18) 0.1215(3) 0.1610(2) 0.0460(9) Uani d . 1
C C43 0.84987(19) 0.1941(3) -0.1155(2) 0.0556(11) Uani d . 1
C C44 0.8485(2) 0.1465(4) -0.1871(3) 0.0698(13) Uani d . 1
H H44 0.8120 0.1430 -0.2311 0.084 Uiso calc R 1
C C45 0.8992(2) 0.1054(4) -0.1936(3) 0.0722(13) Uani d . 1
H H45 0.8973 0.0744 -0.2419 0.087 Uiso calc R 1
C C46 0.9546(2) 0.1095(3) -0.1280(2) 0.0569(11) Uani d . 1
C C47 1.0111(3) 0.0680(3) -0.1272(3) 0.0724(14) Uani d . 1
H H47 1.0125 0.0359 -0.1735 0.087 Uiso calc R 1
C C48 1.0621(2) 0.0744(3) -0.0611(3) 0.0724(14) Uani d . 1
H H48 1.0980 0.0468 -0.0627 0.087 Uiso calc R 1
C C49 1.0621(2) 0.1227(3) 0.0115(3) 0.0582(11) Uani d . 1
C C50 1.1135(2) 0.1331(3) 0.0828(3) 0.0708(13) Uani d . 1
H H50 1.1506 0.1060 0.0852 0.085 Uiso calc R 1
C C51 1.1092(2) 0.1825(4) 0.1482(3) 0.0721(13) Uani d . 1
H H51 1.1435 0.1902 0.1950 0.087 Uiso calc R 1
C C52 1.05307(18) 0.2222(3) 0.1457(3) 0.0544(11) Uani d . 1
C C53 1.00751(17) 0.1630(3) 0.0127(2) 0.0458(9) Uani d . 1
C C54 0.95339(18) 0.1572(3) -0.0572(2) 0.0472(10) Uani d . 1
C C55 0.7945(2) 0.2406(4) -0.1093(3) 0.0784(14) Uani d . 1
H H55A 0.7885 0.2097 -0.0636 0.118 Uiso calc R 1
H H55B 0.7602 0.2239 -0.1574 0.118 Uiso calc R 1
H H55C 0.7987 0.3183 -0.1030 0.118 Uiso calc R 1
C C56 1.04876(19) 0.2811(4) 0.2161(2) 0.0688(13) Uani d . 1
H H56A 1.0179 0.3361 0.1976 0.103 Uiso calc R 1
H H56B 1.0870 0.3148 0.2463 0.103 Uiso calc R 1
H H56C 1.0386 0.2303 0.2499 0.103 Uiso calc 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
_geom_angle_publ_flag
O2 Cu1 O4 91.00(11) y
O2 Cu1 N2 152.67(12) y
O4 Cu1 N2 97.15(11) y
O2 Cu1 N1 104.90(11) y
O4 Cu1 N1 144.27(11) y
N2 Cu1 N1 83.30(11) y
O10 Cu2 O8 90.72(11) y
O10 Cu2 N4 94.59(12) y
O8 Cu2 N4 155.88(12) y
O10 Cu2 N3 143.61(12) y
O8 Cu2 N3 106.20(12) y
N4 Cu2 N3 82.98(13) y
C7 O2 Cu1 110.6(2) ?
C2 O3 H3 109.5 ?
C14 O4 Cu1 108.9(2) ?
C9 O6 H6 109.5 ?
C35 O8 Cu2 104.0(3) ?
C30 O9 H9 109.5 ?
C42 O10 Cu2 109.0(2) ?
C37 O12 H12 109.5 ?
C15 N1 C26 118.7(3) ?
C15 N1 Cu1 130.4(2) ?
C26 N1 Cu1 110.8(2) ?
C24 N2 C25 118.9(3) ?
C24 N2 Cu1 129.3(3) ?
C25 N2 Cu1 111.8(2) ?
C43 N3 C54 119.1(3) ?
C43 N3 Cu2 130.4(3) ?
C54 N3 Cu2 110.1(2) ?
C52 N4 C53 120.1(3) ?
C52 N4 Cu2 128.1(3) ?
C53 N4 Cu2 111.7(2) ?
C2 C1 C6 118.3(4) ?
C2 C1 C7 121.2(4) ?
C6 C1 C7 120.5(4) ?
O3 C2 C1 121.0(4) ?
O3 C2 C3 119.5(5) ?
C1 C2 C3 119.5(5) ?
C4 C3 C2 120.5(5) ?
C4 C3 H3A 119.8 ?
C2 C3 H3A 119.8 ?
C3 C4 C5 121.1(5) ?
C3 C4 H4 119.5 ?
C5 C4 H4 119.5 ?
C6 C5 C4 119.1(5) ?
C6 C5 H5 120.5 ?
C4 C5 H5 120.5 ?
C5 C6 C1 121.5(4) ?
C5 C6 H6A 119.3 ?
C1 C6 H6A 119.3 ?
O1 C7 O2 122.3(4) ?
O1 C7 C1 119.5(4) ?
O2 C7 C1 118.2(4) ?
C13 C8 C9 118.6(4) ?
C13 C8 C14 120.9(4) ?
C9 C8 C14 120.4(4) ?
O6 C9 C10 118.0(4) ?
O6 C9 C8 122.2(4) ?
C10 C9 C8 119.8(4) ?
C11 C10 C9 120.5(4) ?
C11 C10 H10 119.7 ?
C9 C10 H10 119.7 ?
C10 C11 C12 120.5(4) ?
C10 C11 H11 119.7 ?
C12 C11 H11 119.7 ?
C11 C12 C13 119.6(5) ?
C11 C12 H12A 120.2 ?
C13 C12 H12A 120.2 ?
C8 C13 C12 121.0(4) ?
C8 C13 H13 119.5 ?
C12 C13 H13 119.5 ?
O5 C14 O4 122.8(4) ?
O5 C14 C8 119.8(4) ?
O4 C14 C8 117.4(4) ?
N1 C15 C16 121.0(3) ?
N1 C15 C27 118.5(3) ?
C16 C15 C27 120.4(3) ?
C17 C16 C15 121.0(4) ?
C17 C16 H16 119.5 ?
C15 C16 H16 119.5 ?
C16 C17 C18 119.5(4) ?
C16 C17 H17 120.3 ?
C18 C17 H17 120.3 ?
C26 C18 C17 116.9(3) ?
C26 C18 C19 118.7(4) ?
C17 C18 C19 124.5(4) ?
C20 C19 C18 121.7(4) ?
C20 C19 H19 119.2 ?
C18 C19 H19 119.2 ?
C19 C20 C21 120.5(4) ?
C19 C20 H20 119.8 ?
C21 C20 H20 119.8 ?
C25 C21 C22 117.4(4) ?
C25 C21 C20 119.0(3) ?
C22 C21 C20 123.6(4) ?
C23 C22 C21 119.3(4) ?
C23 C22 H22 120.3 ?
C21 C22 H22 120.3 ?
C22 C23 C24 121.0(4) ?
C22 C23 H23 119.5 ?
C24 C23 H23 119.5 ?
N2 C24 C23 120.2(4) ?
N2 C24 C28 119.0(3) ?
C23 C24 C28 120.7(3) ?
N2 C25 C21 123.0(3) ?
N2 C25 C26 116.6(3) ?
C21 C25 C26 120.5(3) ?
N1 C26 C18 123.0(3) ?
N1 C26 C25 117.4(3) ?
C18 C26 C25 119.6(3) ?
C15 C27 H27A 109.5 ?
C15 C27 H27B 109.5 ?
H27A C27 H27B 109.5 ?
C15 C27 H27C 109.5 ?
H27A C27 H27C 109.5 ?
H27B C27 H27C 109.5 ?
C24 C28 H28A 109.5 ?
C24 C28 H28B 109.5 ?
H28A C28 H28B 109.5 ?
C24 C28 H28C 109.5 ?
H28A C28 H28C 109.5 ?
H28B C28 H28C 109.5 ?
C30 C29 C34 119.2(4) ?
C30 C29 C35 120.4(4) ?
C34 C29 C35 120.4(4) ?
O9 C30 C31 118.9(5) ?
O9 C30 C29 120.9(4) ?
C31 C30 C29 120.3(5) ?
C32 C31 C30 120.8(5) ?
C32 C31 H31 119.6 ?
C30 C31 H31 119.6 ?
C31 C32 C33 120.7(5) ?
C31 C32 H32 119.6 ?
C33 C32 H32 119.6 ?
C32 C33 C34 119.5(5) ?
C32 C33 H33 120.2 ?
C34 C33 H33 120.2 ?
C29 C34 C33 119.4(5) ?
C29 C34 H34 120.3 ?
C33 C34 H34 120.3 ?
O7 C35 O8 121.5(4) ?
O7 C35 C29 120.5(4) ?
O8 C35 C29 118.0(4) ?
C41 C36 C37 119.2(4) ?
C41 C36 C42 121.5(4) ?
C37 C36 C42 119.3(4) ?
O12 C37 C38 117.3(4) ?
O12 C37 C36 122.8(4) ?
C38 C37 C36 119.9(4) ?
C39 C38 C37 119.9(5) ?
C39 C38 H38 120.1 ?
C37 C38 H38 120.1 ?
C38 C39 C40 121.7(4) ?
C38 C39 H39 119.1 ?
C40 C39 H39 119.1 ?
C41 C40 C39 118.0(4) ?
C41 C40 H40 121.0 ?
C39 C40 H40 121.0 ?
C40 C41 C36 121.2(4) ?
C40 C41 H41 119.4 ?
C36 C41 H41 119.4 ?
O11 C42 O10 122.4(4) ?
O11 C42 C36 120.1(4) ?
O10 C42 C36 117.6(4) ?
N3 C43 C44 120.1(4) ?
N3 C43 C55 119.0(4) ?
C44 C43 C55 120.9(4) ?
C45 C44 C43 121.3(4) ?
C45 C44 H44 119.3 ?
C43 C44 H44 119.3 ?
C44 C45 C46 120.3(4) ?
C44 C45 H45 119.9 ?
C46 C45 H45 119.9 ?
C45 C46 C54 116.2(4) ?
C45 C46 C47 125.5(4) ?
C54 C46 C47 118.3(4) ?
C48 C47 C46 121.6(4) ?
C48 C47 H47 119.2 ?
C46 C47 H47 119.2 ?
C47 C48 C49 121.2(4) ?
C47 C48 H48 119.4 ?
C49 C48 H48 119.4 ?
C53 C49 C50 116.9(4) ?
C53 C49 C48 118.4(4) ?
C50 C49 C48 124.7(4) ?
C51 C50 C49 120.2(4) ?
C51 C50 H50 119.9 ?
C49 C50 H50 119.9 ?
C50 C51 C52 120.3(4) ?
C50 C51 H51 119.8 ?
C52 C51 H51 119.8 ?
N4 C52 C51 120.3(4) ?
N4 C52 C56 119.3(4) ?
C51 C52 C56 120.4(4) ?
N4 C53 C49 122.0(4) ?
N4 C53 C54 117.3(3) ?
C49 C53 C54 120.7(4) ?
N3 C54 C46 123.1(4) ?
N3 C54 C53 117.2(3) ?
C46 C54 C53 119.7(4) ?
C43 C55 H55A 109.5 ?
C43 C55 H55B 109.5 ?
H55A C55 H55B 109.5 ?
C43 C55 H55C 109.5 ?
H55A C55 H55C 109.5 ?
H55B C55 H55C 109.5 ?
C52 C56 H56A 109.5 ?
C52 C56 H56B 109.5 ?
H56A C56 H56B 109.5 ?
C52 C56 H56C 109.5 ?
H56A C56 H56C 109.5 ?
H56B C56 H56C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 1.931(2) y
Cu1 O4 1.946(2) y
Cu1 N2 1.994(3) y
Cu1 N1 2.022(3) y
Cu2 O10 1.945(2) y
Cu2 O8 1.956(3) y
Cu2 N4 1.992(3) y
Cu2 N3 2.044(3) y
O1 C7 1.249(4) ?
O2 C7 1.267(4) ?
O3 C2 1.350(5) ?
O3 H3 0.8200 ?
O4 C14 1.264(4) ?
O5 C14 1.254(4) ?
O6 C9 1.355(5) ?
O6 H6 0.8200 ?
O7 C35 1.245(4) ?
O8 C35 1.264(4) ?
O9 C30 1.351(5) ?
O9 H9 0.8200 ?
O10 C42 1.275(4) ?
O11 C42 1.254(4) ?
O12 C37 1.343(4) ?
O12 H12 0.8200 ?
N1 C15 1.332(4) ?
N1 C26 1.360(4) ?
N2 C24 1.332(4) ?
N2 C25 1.369(4) ?
N3 C43 1.339(5) ?
N3 C54 1.367(4) ?
N4 C52 1.324(5) ?
N4 C53 1.367(4) ?
C1 C2 1.392(5) ?
C1 C6 1.394(5) ?
C1 C7 1.490(5) ?
C2 C3 1.394(6) ?
C3 C4 1.354(6) ?
C3 H3A 0.9300 ?
C4 C5 1.375(6) ?
C4 H4 0.9300 ?
C5 C6 1.373(5) ?
C5 H5 0.9300 ?
C6 H6A 0.9300 ?
C8 C13 1.381(5) ?
C8 C9 1.399(5) ?
C8 C14 1.484(5) ?
C9 C10 1.392(6) ?
C10 C11 1.364(6) ?
C10 H10 0.9300 ?
C11 C12 1.373(6) ?
C11 H11 0.9300 ?
C12 C13 1.391(5) ?
C12 H12A 0.9300 ?
C13 H13 0.9300 ?
C15 C16 1.396(5) ?
C15 C27 1.504(5) ?
C16 C17 1.350(5) ?
C16 H16 0.9300 ?
C17 C18 1.408(5) ?
C17 H17 0.9300 ?
C18 C26 1.399(5) ?
C18 C19 1.433(5) ?
C19 C20 1.346(5) ?
C19 H19 0.9300 ?
C20 C21 1.436(5) ?
C20 H20 0.9300 ?
C21 C25 1.390(5) ?
C21 C22 1.396(5) ?
C22 C23 1.363(5) ?
C22 H22 0.9300 ?
C23 C24 1.405(5) ?
C23 H23 0.9300 ?
C24 C28 1.501(5) ?
C25 C26 1.431(5) ?
C27 H27A 0.9600 ?
C27 H27B 0.9600 ?
C27 H27C 0.9600 ?
C28 H28A 0.9600 ?
C28 H28B 0.9600 ?
C28 H28C 0.9600 ?
C29 C30 1.387(6) ?
C29 C34 1.395(5) ?
C29 C35 1.487(5) ?
C30 C31 1.377(6) ?
C31 C32 1.344(7) ?
C31 H31 0.9300 ?
C32 C33 1.386(8) ?
C32 H32 0.9300 ?
C33 C34 1.396(6) ?
C33 H33 0.9300 ?
C34 H34 0.9300 ?
C36 C41 1.384(5) ?
C36 C37 1.407(5) ?
C36 C42 1.487(5) ?
C37 C38 1.372(5) ?
C38 C39 1.372(6) ?
C38 H38 0.9300 ?
C39 C40 1.393(6) ?
C39 H39 0.9300 ?
C40 C41 1.384(5) ?
C40 H40 0.9300 ?
C41 H41 0.9300 ?
C43 C44 1.397(5) ?
C43 C55 1.479(6) ?
C44 C45 1.355(6) ?
C44 H44 0.9300 ?
C45 C46 1.400(6) ?
C45 H45 0.9300 ?
C46 C54 1.407(5) ?
C46 C47 1.434(6) ?
C47 C48 1.343(6) ?
C47 H47 0.9300 ?
C48 C49 1.429(6) ?
C48 H48 0.9300 ?
C49 C53 1.399(5) ?
C49 C50 1.404(6) ?
C50 C51 1.356(6) ?
C50 H50 0.9300 ?
C51 C52 1.407(6) ?
C51 H51 0.9300 ?
C52 C56 1.490(6) ?
C53 C54 1.423(5) ?
C55 H55A 0.9600 ?
C55 H55B 0.9600 ?
C55 H55C 0.9600 ?
C56 H56A 0.9600 ?
C56 H56B 0.9600 ?
C56 H56C 0.9600 ?
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
O12 H12 O11 0.82 1.82 2.549(4) 146.8
O9 H9 O7 0.82 1.84 2.561(4) 146.4
O6 H6 O5 0.82 1.85 2.572(4) 146.0
O3 H3 O1 0.82 1.82 2.553(5) 147.9
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
O4 Cu1 O2 C7 141.8(3)
N2 Cu1 O2 C7 34.1(4)
N1 Cu1 O2 C7 -70.5(3)
O2 Cu1 O4 C14 83.0(2)
N2 Cu1 O4 C14 -123.1(2)
N1 Cu1 O4 C14 -34.7(3)
O10 Cu2 O8 C35 104.0(2)
N4 Cu2 O8 C35 1.0(4)
N3 Cu2 O8 C35 -108.7(2)
O8 Cu2 O10 C42 75.4(2)
N4 Cu2 O10 C42 -128.2(2)
N3 Cu2 O10 C42 -43.8(3)
O2 Cu1 N1 C15 -27.3(3)
O4 Cu1 N1 C15 86.4(3)
N2 Cu1 N1 C15 179.3(3)
O2 Cu1 N1 C26 155.9(2)
O4 Cu1 N1 C26 -90.4(3)
N2 Cu1 N1 C26 2.5(2)
O2 Cu1 N2 C24 67.7(4)
O4 Cu1 N2 C24 -38.6(3)
N1 Cu1 N2 C24 177.4(3)
O2 Cu1 N2 C25 -113.6(3)
O4 Cu1 N2 C25 140.1(2)
N1 Cu1 N2 C25 -3.9(2)
O10 Cu2 N3 C43 91.7(4)
O8 Cu2 N3 C43 -22.9(4)
N4 Cu2 N3 C43 179.9(3)
O10 Cu2 N3 C54 -81.1(3)
O8 Cu2 N3 C54 164.3(2)
N4 Cu2 N3 C54 7.1(2)
O10 Cu2 N4 C52 -40.7(3)
O8 Cu2 N4 C52 61.4(5)
N3 Cu2 N4 C52 175.8(3)
O10 Cu2 N4 C53 136.2(2)
O8 Cu2 N4 C53 -121.6(3)
N3 Cu2 N4 C53 -7.3(2)
C6 C1 C2 O3 177.9(4)
C7 C1 C2 O3 -0.8(6)
C6 C1 C2 C3 -2.7(6)
C7 C1 C2 C3 178.7(4)
O3 C2 C3 C4 -177.4(5)
C1 C2 C3 C4 3.2(7)
C2 C3 C4 C5 -1.7(7)
C3 C4 C5 C6 -0.3(7)
C4 C5 C6 C1 0.7(6)
C2 C1 C6 C5 0.7(6)
C7 C1 C6 C5 179.4(4)
Cu1 O2 C7 O1 -3.1(5)
Cu1 O2 C7 C1 175.1(3)
C2 C1 C7 O1 5.6(6)
C6 C1 C7 O1 -173.1(4)
C2 C1 C7 O2 -172.7(4)
C6 C1 C7 O2 8.7(5)
C13 C8 C9 O6 -178.6(4)
C14 C8 C9 O6 4.4(5)
C13 C8 C9 C10 1.6(6)
C14 C8 C9 C10 -175.5(3)
O6 C9 C10 C11 179.4(4)
C8 C9 C10 C11 -0.8(6)
C9 C10 C11 C12 -0.7(8)
C10 C11 C12 C13 1.4(8)
C9 C8 C13 C12 -1.0(6)
C14 C8 C13 C12 176.1(4)
C11 C12 C13 C8 -0.5(7)
Cu1 O4 C14 O5 9.1(4)
Cu1 O4 C14 C8 -170.0(2)
C13 C8 C14 O5 173.0(4)
C9 C8 C14 O5 -9.9(5)
C13 C8 C14 O4 -7.8(5)
C9 C8 C14 O4 169.2(3)
C26 N1 C15 C16 -1.6(5)
Cu1 N1 C15 C16 -178.2(3)
C26 N1 C15 C27 176.9(3)
Cu1 N1 C15 C27 0.3(5)
N1 C15 C16 C17 0.7(6)
C27 C15 C16 C17 -177.7(4)
C15 C16 C17 C18 1.3(6)
C16 C17 C18 C26 -2.3(5)
C16 C17 C18 C19 178.1(4)
C26 C18 C19 C20 2.0(6)
C17 C18 C19 C20 -178.4(4)
C18 C19 C20 C21 -1.7(6)
C19 C20 C21 C25 0.0(6)
C19 C20 C21 C22 -178.7(4)
C25 C21 C22 C23 -2.4(6)
C20 C21 C22 C23 176.3(4)
C21 C22 C23 C24 1.1(6)
C25 N2 C24 C23 -4.8(5)
Cu1 N2 C24 C23 173.8(3)
C25 N2 C24 C28 174.4(3)
Cu1 N2 C24 C28 -7.0(5)
C22 C23 C24 N2 2.6(6)
C22 C23 C24 C28 -176.5(4)
C24 N2 C25 C21 3.4(5)
Cu1 N2 C25 C21 -175.4(3)
C24 N2 C25 C26 -176.5(3)
Cu1 N2 C25 C26 4.6(4)
C22 C21 C25 N2 0.2(5)
C20 C21 C25 N2 -178.6(3)
C22 C21 C25 C26 -179.8(3)
C20 C21 C25 C26 1.4(5)
C15 N1 C26 C18 0.5(5)
Cu1 N1 C26 C18 177.7(3)
C15 N1 C26 C25 -177.9(3)
Cu1 N1 C26 C25 -0.7(4)
C17 C18 C26 N1 1.5(5)
C19 C18 C26 N1 -178.9(3)
C17 C18 C26 C25 179.8(3)
C19 C18 C26 C25 -0.6(5)
N2 C25 C26 N1 -2.7(5)
C21 C25 C26 N1 177.4(3)
N2 C25 C26 C18 178.9(3)
C21 C25 C26 C18 -1.1(5)
C34 C29 C30 O9 176.9(4)
C35 C29 C30 O9 -1.1(6)
C34 C29 C30 C31 -3.3(6)
C35 C29 C30 C31 178.7(4)
O9 C30 C31 C32 -176.1(5)
C29 C30 C31 C32 4.0(7)
C30 C31 C32 C33 -1.5(8)
C31 C32 C33 C34 -1.6(8)
C30 C29 C34 C33 0.2(6)
C35 C29 C34 C33 178.1(4)
C32 C33 C34 C29 2.3(7)
Cu2 O8 C35 O7 8.9(4)
Cu2 O8 C35 C29 -169.2(3)
C30 C29 C35 O7 13.4(6)
C34 C29 C35 O7 -164.5(4)
C30 C29 C35 O8 -168.4(4)
C34 C29 C35 O8 13.7(5)
C41 C36 C37 O12 -178.0(3)
C42 C36 C37 O12 1.6(5)
C41 C36 C37 C38 1.4(5)
C42 C36 C37 C38 -179.0(3)
O12 C37 C38 C39 178.1(4)
C36 C37 C38 C39 -1.3(6)
C37 C38 C39 C40 -0.1(7)
C38 C39 C40 C41 1.4(7)
C39 C40 C41 C36 -1.3(6)
C37 C36 C41 C40 -0.1(6)
C42 C36 C41 C40 -179.6(4)
Cu2 O10 C42 O11 0.7(4)
Cu2 O10 C42 C36 -179.8(2)
C41 C36 C42 O11 178.5(3)
C37 C36 C42 O11 -1.1(5)
C41 C36 C42 O10 -1.0(5)
C37 C36 C42 O10 179.4(3)
C54 N3 C43 C44 0.8(6)
Cu2 N3 C43 C44 -171.4(3)
C54 N3 C43 C55 -178.9(4)
Cu2 N3 C43 C55 8.8(6)
N3 C43 C44 C45 -0.8(7)
C55 C43 C44 C45 178.9(4)
C43 C44 C45 C46 0.3(7)
C44 C45 C46 C54 0.3(6)
C44 C45 C46 C47 179.4(4)
C45 C46 C47 C48 -179.4(4)
C54 C46 C47 C48 -0.3(6)
C46 C47 C48 C49 0.2(7)
C47 C48 C49 C53 0.4(6)
C47 C48 C49 C50 -179.6(4)
C53 C49 C50 C51 -1.4(6)
C48 C49 C50 C51 178.5(4)
C49 C50 C51 C52 1.0(7)
C53 N4 C52 C51 -3.6(6)
Cu2 N4 C52 C51 173.1(3)
C53 N4 C52 C56 175.1(3)
Cu2 N4 C52 C56 -8.2(5)
C50 C51 C52 N4 1.6(6)
C50 C51 C52 C56 -177.2(4)
C52 N4 C53 C49 3.2(5)
Cu2 N4 C53 C49 -174.0(3)
C52 N4 C53 C54 -176.5(3)
Cu2 N4 C53 C54 6.2(4)
C50 C49 C53 N4 -0.6(5)
C48 C49 C53 N4 179.4(3)
C50 C49 C53 C54 179.1(3)
C48 C49 C53 C54 -0.9(5)
C43 N3 C54 C46 -0.2(5)
Cu2 N3 C54 C46 173.5(3)
C43 N3 C54 C53 -179.6(3)
Cu2 N3 C54 C53 -5.9(4)
C45 C46 C54 N3 -0.4(5)
C47 C46 C54 N3 -179.5(3)
C45 C46 C54 C53 179.0(4)
C47 C46 C54 C53 -0.2(5)
N4 C53 C54 N3 -0.1(5)
C49 C53 C54 N3 -179.9(3)
N4 C53 C54 C46 -179.5(3)
C49 C53 C54 C46 0.7(5)
