#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:43:21 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179074 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/36/4303648.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_4303648
loop_
_publ_author_name
'Raquel Ferreirós-Martínez'
'David Esteban-Gómez'
'Carlos Platas-Iglesias'
'Andrés de Blas'
'Teresa Rodríguez-Blas'
_publ_contact_author_address
;
Departamento de Quimica Fundamental
Facultade de Ciencias
Universidade da Coruna
Campus da Zapateira s/n
15071 A Coruna
Spain
;
_publ_contact_author_email       ucambv@udc.es
_publ_contact_author_fax         '+ 34 981 167065'
_publ_contact_author_name        'De Blas, Andres'
_publ_contact_author_phone       '+ 34 981 167000'
_publ_section_title
;
Selective Chelation of Cd(II) and Pb(II) versus Ca(II) and Zn(II) by Using
Octadentate Ligands Containing Pyridinecarboxylate and Pyridyl Pendants
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10976
_journal_page_last               10987
_journal_paper_doi               10.1021/ic900838j
_journal_volume                  48
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H26 N6 O4 Zn, 3.83(H2 O) '
_chemical_formula_sum            'C28 H33.65 N6 O7.83 Zn'
_chemical_formula_weight         644.83
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2009-02-16T18:01:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                103.007(1)
_cell_angle_beta                 94.263(1)
_cell_angle_gamma                109.660(1)
_cell_formula_units_Z            2
_cell_length_a                   10.7910(6)
_cell_length_b                   11.8384(7)
_cell_length_c                   12.6031(7)
_cell_measurement_reflns_used    8450
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.2635
_cell_measurement_theta_min      2.6775
_cell_measurement_wavelength     0.71073
_cell_volume                     1457.38(14)
_computing_cell_refinement       'SAINT V7.12A'
_computing_data_collection       'SMART BRUKER'
_computing_data_reduction
'XPREP Version 6.14 COPYRIGHT(c) 2003 Bruker-AXS'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD'
_diffrn_measurement_method       'omega and  phi rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20424
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SABADS, Bruker-AXS  Version 2004/1
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             673
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.06
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         7198
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0399P)²+0.6465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                6313
_reflns_number_total             7198
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic900838j_si_003_2.cif
_cod_data_source_block           compound1
_cod_database_code               4303648
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O5W O 0.81417(14) 0.04246(13) 0.11379(11) 0.0322(3) Uani 1 1 d . A 1
H1W H 0.775 -0.0167 0.0491 0.039 Uiso 1 1 d . B 1
H2W H 0.9016 0.0717 0.1127 0.039 Uiso 1 1 d . C 1
O6W O 0.60261(14) 0.56981(12) 0.15813(10) 0.0313(3) Uani 1 1 d D D 1
H3W H 0.5315 0.5076 0.1352 0.047 Uiso 1 1 d D E 1
H4W H 0.5995 0.6156 0.2193 0.038 Uiso 1 1 d . F 1
O7A O 1.3654(2) 0.3819(2) 0.04775(19) 0.0289(5) Uani 0.826(3) 1 d PD G 1
O7B O 1.4032(13) 0.3589(9) 0.0195(9) 0.033(2) Uani 0.174(3) 1 d PD G 2
H6W H 1.357(3) 0.3103(19) 0.055(2) 0.04 Uiso 0.826(3) 1 d PD G 1
H5W H 1.3664 0.3854 -0.0195 0.04 Uiso 0.826(3) 1 d PD G 1
H61W H 1.4493 0.4116 0.0831 0.04 Uiso 0.174(3) 1 d P G 2
H62W H 1.3856 0.2841 0.0243 0.04 Uiso 0.174(3) 1 d PD G 2
O8W O 1.07634(18) 0.18670(16) 0.14136(16) 0.0362(5) Uani 0.826(3) 1 d PD G 1
H7W H 1.150(2) 0.191(3) 0.114(2) 0.043 Uiso 0.826(3) 1 d PD G 1
H8W H 1.064(3) 0.255(2) 0.151(2) 0.043 Uiso 0.826(3) 1 d PD G 1
Zn1 Zn 0.593377(17) 0.241046(15) 0.363374(14) 0.01252(6) Uani 1 1 d . G .
O1 O 0.46480(10) 0.19861(10) 0.48107(9) 0.0152(2) Uani 1 1 d . . .
O2 O 0.40762(11) 0.28590(10) 0.63755(9) 0.0176(2) Uani 1 1 d . . .
O3 O 0.46908(11) 0.25460(10) 0.23208(9) 0.0164(2) Uani 1 1 d . G .
O4 O 0.32348(12) 0.14225(11) 0.07823(10) 0.0216(2) Uani 1 1 d . G .
N1 N 0.64290(12) 0.40928(11) 0.47427(10) 0.0125(2) Uani 1 1 d . G .
N2 N 0.78600(12) 0.36459(12) 0.31423(10) 0.0135(2) Uani 1 1 d . . .
N4 N 0.73501(12) 0.15821(11) 0.42679(10) 0.0133(2) Uani 1 1 d . . .
N5 N 0.98906(13) 0.20754(13) 0.60572(12) 0.0188(3) Uani 1 1 d . G .
N6 N 0.53402(12) 0.06817(11) 0.25623(10) 0.0125(2) Uani 1 1 d . . .
C15 C 0.85309(15) 0.20352(14) 0.37267(13) 0.0143(3) Uani 1 1 d . G .
H15A H 0.8333 0.156 0.2959 0.017 Uiso 1 1 calc R . .
H15B H 0.9278 0.1903 0.4084 0.017 Uiso 1 1 calc R . .
C27 C 0.44883(15) 0.04505(14) 0.16407(12) 0.0138(3) Uani 1 1 d . G .
C23 C 0.58231(15) -0.01639(14) 0.27563(13) 0.0143(3) Uani 1 1 d . G .
C3 C 0.60680(15) 0.52447(14) 0.64129(13) 0.0151(3) Uani 1 1 d . G .
H3 H 0.5623 0.5274 0.7017 0.018 Uiso 1 1 calc R . .
C16 C 0.76496(15) 0.19843(14) 0.54961(12) 0.0150(3) Uani 1 1 d . G .
H16A H 0.6813 0.1733 0.5776 0.018 Uiso 1 1 calc R . .
H16B H 0.8033 0.2886 0.5726 0.018 Uiso 1 1 calc R . .
C1 C 0.47426(14) 0.28945(14) 0.56115(12) 0.0134(3) Uani 1 1 d . G .
C28 C 0.40940(15) 0.15565(14) 0.15676(12) 0.0143(3) Uani 1 1 d . . .
C26 C 0.40671(16) -0.06779(14) 0.08500(13) 0.0180(3) Uani 1 1 d . . .
H26 H 0.3458 -0.0843 0.0221 0.022 Uiso 1 1 calc R G .
C14 C 0.89149(14) 0.34140(14) 0.37884(13) 0.0143(3) Uani 1 1 d . G .
H14A H 0.9059 0.3884 0.4553 0.017 Uiso 1 1 calc R . .
H14B H 0.9744 0.3701 0.3505 0.017 Uiso 1 1 calc R . .
C18 C 0.81008(17) 0.05191(16) 0.65228(14) 0.0223(3) Uani 1 1 d . G .
H18 H 0.7188 0.0112 0.6474 0.027 Uiso 1 1 calc R . .
C17 C 0.85817(15) 0.14921(14) 0.60393(12) 0.0148(3) Uani 1 1 d . . .
N3A N 1.03028(17) 0.41783(17) 0.17348(14) 0.0219(4) Uani 0.826(3) 1 d PU G 1
C22 C 0.67132(15) 0.02103(14) 0.38605(13) 0.0157(3) Uani 1 1 d . G .
H22A H 0.6188 -0.0111 0.4392 0.019 Uiso 1 1 calc R . .
H22B H 0.7397 -0.0151 0.3785 0.019 Uiso 1 1 calc R . .
C7 C 0.79287(15) 0.49428(14) 0.35641(13) 0.0152(3) Uani 1 1 d . G .
H7A H 0.7442 0.5155 0.3009 0.018 Uiso 1 1 calc R . .
H7B H 0.8852 0.5504 0.3701 0.018 Uiso 1 1 calc R . .
C6 C 0.73498(14) 0.51111(13) 0.46133(12) 0.0130(3) Uani 1 1 d . . .
C24 C 0.54717(16) -0.13093(14) 0.19851(14) 0.0190(3) Uani 1 1 d . . .
H24 H 0.5822 -0.1896 0.2108 0.023 Uiso 1 1 calc R G .
C2 C 0.57871(14) 0.41451(13) 0.56176(12) 0.0125(3) Uani 1 1 d . . .
C5 C 0.76853(15) 0.62555(14) 0.53802(13) 0.0155(3) Uani 1 1 d . G .
H5 H 0.8328 0.6964 0.5285 0.019 Uiso 1 1 calc R . .
C8A C 0.7942(9) 0.3411(4) 0.1947(7) 0.0146(8) Uani 0.826(3) 1 d PU G 1
H81A H 0.7132 0.3408 0.1554 0.018 Uiso 0.826(3) 1 calc PR G 1
H82A H 0.7983 0.2591 0.1684 0.018 Uiso 0.826(3) 1 calc PR G 1
C20 C 1.03506(17) 0.07694(16) 0.71200(14) 0.0227(3) Uani 1 1 d . G .
H20 H 1.0978 0.0559 0.7497 0.027 Uiso 1 1 calc R . .
C4 C 0.70412(15) 0.63174(14) 0.62885(13) 0.0163(3) Uani 1 1 d . . .
H4 H 0.7255 0.7072 0.6816 0.02 Uiso 1 1 calc R G .
C12A C 1.1346(3) 0.6153(3) 0.1349(2) 0.0332(6) Uani 0.826(3) 1 d PU G 1
H12A H 1.2121 0.6761 0.1272 0.04 Uiso 0.826(3) 1 calc PR G 1
C21 C 1.07412(17) 0.17014(17) 0.65816(15) 0.0231(3) Uani 1 1 d . . .
H21 H 1.1648 0.209 0.6585 0.028 Uiso 1 1 calc R G .
C25 C 0.45924(17) -0.15613(15) 0.10316(14) 0.0210(3) Uani 1 1 d . G .
H25 H 0.4349 -0.2323 0.0508 0.025 Uiso 1 1 calc R . .
C10A C 0.9016(2) 0.5403(2) 0.13980(18) 0.0229(5) Uani 0.826(3) 1 d PU G 1
H10A H 0.8192 0.5491 0.1325 0.027 Uiso 0.826(3) 1 calc PR G 1
C13A C 1.1381(3) 0.5069(3) 0.1575(2) 0.0300(6) Uani 0.826(3) 1 d PU G 1
H13A H 1.2191 0.4952 0.1618 0.036 Uiso 0.826(3) 1 calc PR G 1
C11A C 1.0147(3) 0.6308(2) 0.12425(19) 0.0305(5) Uani 0.826(3) 1 d PU G 1
H11A H 1.009 0.7013 0.1067 0.037 Uiso 0.826(3) 1 calc PR G 1
C19 C 0.90001(18) 0.01620(17) 0.70796(15) 0.0267(4) Uani 1 1 d . . .
H19 H 0.8699 -0.0477 0.7421 0.032 Uiso 1 1 calc R G .
C9A C 0.9137(3) 0.4361(3) 0.1665(2) 0.0171(5) Uani 0.826(3) 1 d PU G 1
N3B N 0.9867(9) 0.3113(9) 0.1285(8) 0.029(2) Uani 0.174(3) 1 d PU G 2
C10B C 0.9608(15) 0.5086(13) 0.1582(9) 0.033(3) Uani 0.174(3) 1 d PU G 2
H10B H 0.9069 0.5557 0.1709 0.04 Uiso 0.174(3) 1 calc PR G 2
C13B C 1.1084(12) 0.3591(12) 0.1035(11) 0.038(3) Uani 0.174(3) 1 d PU G 2
H13B H 1.156 0.3074 0.083 0.045 Uiso 0.174(3) 1 calc PR G 2
C12B C 1.1649(14) 0.4838(12) 0.1076(13) 0.039(3) Uani 0.174(3) 1 d PU G 2
H12B H 1.2496 0.5132 0.0891 0.046 Uiso 0.174(3) 1 calc PR G 2
C9B C 0.9172(15) 0.3867(15) 0.1574(12) 0.025(3) Uani 0.174(3) 1 d PU G 2
C11B C 1.1029(15) 0.5638(13) 0.1371(11) 0.0305(5) Uani 0.174(3) 1 d PU G 2
H11B H 1.1444 0.6485 0.1444 0.037 Uiso 0.174(3) 1 calc PR G 2
C8B C 0.789(5) 0.320(3) 0.189(4) 0.0146(8) Uani 0.174(3) 1 d PU G 2
H81B H 0.7722 0.2318 0.1688 0.018 Uiso 0.174(3) 1 calc PR G 2
H82B H 0.7178 0.3331 0.1469 0.018 Uiso 0.174(3) 1 calc PR G 2
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
H1W O5W H2W 107.2 . . ?
H3W O6W H4W 111.3 . . ?
H6W O7A H5W 112.7(18) . . ?
H6W O7A H61W 89(2) . . ?
H5W O7A H61W 108.8(2) . . ?
H5W O7A H62W 89.90(19) . . ?
H61W O7A H62W 82.76(17) . . ?
H6W O7B H5W 119(3) . . ?
H6W O7B H61W 89(2) . . ?
H5W O7B H61W 116.4(11) . . ?
H5W O7B H62W 130.3(15) . . ?
H61W O7B H62W 109.2(11) . . ?
H7W O8W H8W 112(2) . . ?
N1 Zn1 N6 176.63(5) . . yes
N1 Zn1 O3 102.65(5) . . yes
N6 Zn1 O3 77.33(5) . . yes
N1 Zn1 O1 77.61(4) . . yes
N6 Zn1 O1 99.09(4) . . yes
O3 Zn1 O1 103.94(4) . . yes
N1 Zn1 N4 103.95(5) . . yes
N6 Zn1 N4 76.84(5) . . yes
O3 Zn1 N4 150.66(4) . . yes
O1 Zn1 N4 93.69(4) . . yes
N1 Zn1 N2 76.16(5) . . yes
N6 Zn1 N2 107.21(5) . . yes
O3 Zn1 N2 92.55(4) . . yes
O1 Zn1 N2 151.50(4) . . yes
N4 Zn1 N2 82.03(4) . . yes
C1 O1 Zn1 115.92(9) . . ?
C28 O3 Zn1 116.12(10) . . ?
C6 N1 C2 120.88(13) . . ?
C6 N1 Zn1 121.63(10) . . ?
C2 N1 Zn1 117.49(10) . . ?
C7 N2 C8A 108.6(2) . . ?
C7 N2 C14 110.85(12) . . ?
C8A N2 C14 112.8(3) . . ?
C7 N2 C8B 116.5(13) . . ?
C14 N2 C8B 109.6(17) . . ?
C7 N2 Zn1 105.51(9) . . ?
C8A N2 Zn1 116.8(3) . . ?
C14 N2 Zn1 101.91(8) . . ?
C8B N2 Zn1 111.5(16) . . ?
C22 N4 C15 109.90(12) . . ?
C22 N4 C16 111.02(11) . . ?
C15 N4 C16 113.85(12) . . ?
C22 N4 Zn1 107.69(9) . . ?
C15 N4 Zn1 103.33(9) . . ?
C16 N4 Zn1 110.64(9) . . ?
C21 N5 C17 117.55(14) . . ?
C23 N6 C27 121.58(13) . . ?
C23 N6 Zn1 120.98(10) . . ?
C27 N6 Zn1 117.40(10) . . ?
N4 C15 C14 111.49(12) . . ?
N4 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
N4 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108 . . ?
N6 C27 C26 121.50(14) . . ?
N6 C27 C28 113.00(13) . . ?
C26 C27 C28 125.48(14) . . ?
N6 C23 C24 120.21(14) . . ?
N6 C23 C22 115.26(13) . . ?
C24 C23 C22 124.50(14) . . ?
C2 C3 C4 118.20(14) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
N4 C16 C17 116.54(12) . . ?
N4 C16 H16A 108.2 . . ?
C17 C16 H16A 108.2 . . ?
N4 C16 H16B 108.2 . . ?
C17 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
O2 C1 O1 126.49(14) . . ?
O2 C1 C2 118.01(13) . . ?
O1 C1 C2 115.49(13) . . ?
O4 C28 O3 125.56(14) . . ?
O4 C28 C27 118.69(13) . . ?
O3 C28 C27 115.74(13) . . ?
C27 C26 C25 117.44(15) . . ?
C27 C26 H26 121.3 . . ?
C25 C26 H26 121.3 . . ?
N2 C14 C15 111.38(12) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108 . . ?
C19 C18 C17 119.11(15) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
N5 C17 C18 122.37(15) . . ?
N5 C17 C16 116.27(13) . . ?
C18 C17 C16 121.32(14) . . ?
C13A N3A C9A 117.5(2) . . ?
N4 C22 C23 110.87(12) . . ?
N4 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
N2 C7 C6 111.48(12) . . ?
N2 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108 . . ?
N1 C6 C5 121.13(14) . . ?
N1 C6 C7 115.59(13) . . ?
C5 C6 C7 123.20(13) . . ?
C25 C24 C23 118.83(15) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
N1 C2 C3 121.32(13) . . ?
N1 C2 C1 113.46(13) . . ?
C3 C2 C1 125.21(13) . . ?
C4 C5 C6 118.47(14) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N2 C8A C9A 114.2(5) . . ?
N2 C8A H81A 108.7 . . ?
C9A C8A H81A 108.7 . . ?
N2 C8A H82A 108.7 . . ?
C9A C8A H82A 108.7 . . ?
H81A C8A H82A 107.6 . . ?
C19 C20 C21 117.98(16) . . ?
C19 C20 H20 121 . . ?
C21 C20 H20 121 . . ?
C5 C4 C3 119.99(14) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
C11A C12A C13A 118.5(2) . . ?
C11A C12A H12A 120.7 . . ?
C13A C12A H12A 120.7 . . ?
N5 C21 C20 123.89(16) . . ?
N5 C21 H21 118.1 . . ?
C20 C21 H21 118.1 . . ?
C24 C25 C26 120.41(15) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C11A C10A C9A 118.8(2) . . ?
C11A C10A H10A 120.6 . . ?
C9A C10A H10A 120.6 . . ?
N3A C13A C12A 123.4(3) . . ?
N3A C13A H13A 118.3 . . ?
C12A C13A H13A 118.3 . . ?
C12A C11A C10A 119.4(2) . . ?
C12A C11A H11A 120.3 . . ?
C10A C11A H11A 120.3 . . ?
C20 C19 C18 119.04(16) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
N3A C9A C10A 122.2(2) . . ?
N3A C9A C8A 117.6(4) . . ?
C10A C9A C8A 120.1(3) . . ?
C13B N3B C9B 119.1(11) . . ?
C13B N3B H8W 66.9(14) . . ?
C9B N3B H8W 152.9(17) . . ?
C9B C10B C11B 116.1(14) . . ?
C9B C10B H10B 122 . . ?
C11B C10B H10B 122 . . ?
N3B C13B C12B 121.3(13) . . ?
N3B C13B H8W 54.6(11) . . ?
C12B C13B H8W 154.6(17) . . ?
N3B C13B H13B 119.4 . . ?
C12B C13B H13B 119.4 . . ?
H8W C13B H13B 70.7 . . ?
C11B C12B C13B 122.7(15) . . ?
C11B C12B H12B 118.6 . . ?
C13B C12B H12B 118.6 . . ?
N3B C9B C10B 124.1(13) . . ?
N3B C9B C8B 111.8(17) . . ?
C10B C9B C8B 124.1(18) . . ?
C12B C11B C10B 116.3(13) . . ?
C12B C11B H11B 121.9 . . ?
C10B C11B H11B 121.9 . . ?
C9B C8B N2 113(3) . . ?
C9B C8B H81B 109.1 . . ?
N2 C8B H81B 109.1 . . ?
C9B C8B H82B 109 . . ?
N2 C8B H82B 109.1 . . ?
H81B C8B H82B 107.8 . . ?
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
O5W H1W 0.91 . ?
O5W H2W 0.89 . ?
O6W H3W 0.84 . ?
O6W H4W 0.85 . ?
O7A H6W 0.851(15) . ?
O7A H5W 0.858(2) . ?
O7A H61W 0.893(2) . ?
O7A H62W 1.225(2) . ?
O7B H6W 0.86(2) . ?
O7B H5W 0.788(11) . ?
O7B H61W 0.886(12) . ?
O7B H62W 0.859(9) . ?
O8W H7W 0.885(16) . ?
O8W H8W 0.849(16) . ?
Zn1 N1 2.0311(13) . yes
Zn1 N6 2.0415(12) . yes
Zn1 O3 2.1207(11) . yes
Zn1 O1 2.1330(11) . yes
Zn1 N4 2.2618(13) . yes
Zn1 N2 2.3231(13) . yes
O1 C1 1.2680(18) . ?
O2 C1 1.2437(18) . ?
O3 C28 1.2606(18) . ?
O4 C28 1.2483(19) . ?
N1 C6 1.3317(19) . ?
N1 C2 1.3459(19) . ?
N2 C7 1.4817(19) . ?
N2 C8A 1.485(9) . ?
N2 C14 1.4857(19) . ?
N2 C8B 1.56(5) . ?
N4 C22 1.4815(19) . ?
N4 C15 1.4869(19) . ?
N4 C16 1.4891(19) . ?
N5 C21 1.338(2) . ?
N5 C17 1.3433(19) . ?
N6 C23 1.3325(19) . ?
N6 C27 1.341(2) . ?
C15 C14 1.525(2) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C27 C26 1.382(2) . ?
C27 C28 1.526(2) . ?
C23 C24 1.390(2) . ?
C23 C22 1.514(2) . ?
C3 C2 1.376(2) . ?
C3 C4 1.399(2) . ?
C3 H3 0.93 . ?
C16 C17 1.514(2) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C1 C2 1.527(2) . ?
C26 C25 1.398(2) . ?
C26 H26 0.93 . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C18 C19 1.386(2) . ?
C18 C17 1.389(2) . ?
C18 H18 0.93 . ?
N3A C13A 1.346(3) . ?
N3A C9A 1.346(3) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C7 C6 1.506(2) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C6 C5 1.389(2) . ?
C24 C25 1.383(2) . ?
C24 H24 0.93 . ?
C5 C4 1.383(2) . ?
C5 H5 0.93 . ?
C8A C9A 1.525(8) . ?
C8A H81A 0.97 . ?
C8A H82A 0.97 . ?
C20 C19 1.382(3) . ?
C20 C21 1.386(2) . ?
C20 H20 0.93 . ?
C4 H4 0.93 . ?
C12A C11A 1.368(4) . ?
C12A C13A 1.387(4) . ?
C12A H12A 0.93 . ?
C21 H21 0.93 . ?
C25 H25 0.93 . ?
C10A C11A 1.387(3) . ?
C10A C9A 1.393(3) . ?
C10A H10A 0.93 . ?
C13A H13A 0.93 . ?
C11A H11A 0.93 . ?
C19 H19 0.93 . ?
N3B C13B 1.337(14) . ?
N3B C9B 1.355(18) . ?
N3B H8W 1.28(2) . ?
C10B C9B 1.356(17) . ?
C10B C11B 1.52(2) . ?
C10B H10B 0.93 . ?
C13B C12B 1.381(18) . ?
C13B H13B 0.93 . ?
C12B C11B 1.34(2) . ?
C12B H12B 0.93 . ?
C9B C8B 1.48(5) . ?
C11B H11B 0.93 . ?
C8B H81B 0.97 . ?
C8B H82B 0.97 . ?
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
O5W H1W O4 0.91 1.88 2.7825(17) 173.71(10) 2_655
O7A H6W O4 0.851(15) 1.989(15) 2.838(2) 175(3) 1_655
O7A H5W O6W 0.858(2) 1.9572(13) 2.801(3) 167.44(16) 2_765
O6W H3W O7A 0.84 1.953(2) 2.772(3) 164.44(11) 1_455
O6W H4W O2 0.84 1.94 2.7839(17) 177.27(10) 2_666
O8W H7W O4 0.885(16) 2.179(17) 3.016(2) 157(3) 1_655
O8W H8W N3A 0.849(16) 2.040(17) 2.889(3) 179(3) .
O7B H62W O4 0.859(9) 1.8854(12) 2.708(9) 159.8(7) 1_655
O5W H2W O8W 0.89 1.8681(17) 2.716(2) 158.23(10) .
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
N1 Zn1 O1 C1 0.50(10) . . . . ?
N6 Zn1 O1 C1 -178.77(10) . . . . ?
O3 Zn1 O1 C1 -99.67(10) . . . . ?
N4 Zn1 O1 C1 103.98(10) . . . . ?
N2 Zn1 O1 C1 23.91(15) . . . . ?
N1 Zn1 O3 C28 -171.14(10) . . . . ?
N6 Zn1 O3 C28 5.41(10) . . . . ?
O1 Zn1 O3 C28 -90.97(11) . . . . ?
N4 Zn1 O3 C28 34.24(15) . . . . ?
N2 Zn1 O3 C28 112.48(11) . . . . ?
O3 Zn1 N1 C6 -77.54(12) . . . . ?
O1 Zn1 N1 C6 -179.28(12) . . . . ?
N4 Zn1 N1 C6 89.96(12) . . . . ?
N2 Zn1 N1 C6 11.98(11) . . . . ?
O3 Zn1 N1 C2 102.24(11) . . . . ?
O1 Zn1 N1 C2 0.51(10) . . . . ?
N4 Zn1 N1 C2 -90.25(11) . . . . ?
N2 Zn1 N1 C2 -168.23(11) . . . . ?
N1 Zn1 N2 C7 -24.01(9) . . . . ?
N6 Zn1 N2 C7 155.93(9) . . . . ?
O3 Zn1 N2 C7 78.40(9) . . . . ?
O1 Zn1 N2 C7 -47.57(14) . . . . ?
N4 Zn1 N2 C7 -130.57(10) . . . . ?
N1 Zn1 N2 C8A -144.7(3) . . . . ?
N6 Zn1 N2 C8A 35.2(3) . . . . ?
O3 Zn1 N2 C8A -42.3(3) . . . . ?
O1 Zn1 N2 C8A -168.3(3) . . . . ?
N4 Zn1 N2 C8A 108.7(3) . . . . ?
N1 Zn1 N2 C14 91.84(9) . . . . ?
N6 Zn1 N2 C14 -88.23(9) . . . . ?
O3 Zn1 N2 C14 -165.75(9) . . . . ?
O1 Zn1 N2 C14 68.28(13) . . . . ?
N4 Zn1 N2 C14 -14.73(9) . . . . ?
N1 Zn1 N2 C8B -151.3(16) . . . . ?
N6 Zn1 N2 C8B 28.6(16) . . . . ?
O3 Zn1 N2 C8B -48.9(16) . . . . ?
O1 Zn1 N2 C8B -174.9(16) . . . . ?
N4 Zn1 N2 C8B 102.1(16) . . . . ?
N1 Zn1 N4 C22 154.63(9) . . . . ?
N6 Zn1 N4 C22 -22.00(9) . . . . ?
O3 Zn1 N4 C22 -50.89(14) . . . . ?
O1 Zn1 N4 C22 76.49(9) . . . . ?
N2 Zn1 N4 C22 -131.85(10) . . . . ?
N1 Zn1 N4 C15 -89.09(9) . . . . ?
N6 Zn1 N4 C15 94.28(9) . . . . ?
O3 Zn1 N4 C15 65.39(13) . . . . ?
O1 Zn1 N4 C15 -167.23(9) . . . . ?
N2 Zn1 N4 C15 -15.57(9) . . . . ?
N1 Zn1 N4 C16 33.13(10) . . . . ?
N6 Zn1 N4 C16 -143.49(10) . . . . ?
O3 Zn1 N4 C16 -172.38(9) . . . . ?
O1 Zn1 N4 C16 -45.01(9) . . . . ?
N2 Zn1 N4 C16 106.66(9) . . . . ?
O3 Zn1 N6 C23 175.38(12) . . . . ?
O1 Zn1 N6 C23 -82.26(11) . . . . ?
N4 Zn1 N6 C23 9.43(11) . . . . ?
N2 Zn1 N6 C23 86.63(11) . . . . ?
O3 Zn1 N6 C27 -2.17(10) . . . . ?
O1 Zn1 N6 C27 100.19(11) . . . . ?
N4 Zn1 N6 C27 -168.13(11) . . . . ?
N2 Zn1 N6 C27 -90.92(11) . . . . ?
C22 N4 C15 C14 159.67(12) . . . . ?
C16 N4 C15 C14 -75.08(15) . . . . ?
Zn1 N4 C15 C14 44.97(13) . . . . ?
C23 N6 C27 C26 0.2(2) . . . . ?
Zn1 N6 C27 C26 177.77(11) . . . . ?
C23 N6 C27 C28 -178.23(13) . . . . ?
Zn1 N6 C27 C28 -0.69(16) . . . . ?
C27 N6 C23 C24 1.4(2) . . . . ?
Zn1 N6 C23 C24 -176.01(11) . . . . ?
C27 N6 C23 C22 -176.78(13) . . . . ?
Zn1 N6 C23 C22 5.77(17) . . . . ?
C22 N4 C16 C17 60.08(16) . . . . ?
C15 N4 C16 C17 -64.56(16) . . . . ?
Zn1 N4 C16 C17 179.59(10) . . . . ?
Zn1 O1 C1 O2 178.74(12) . . . . ?
Zn1 O1 C1 C2 -1.28(16) . . . . ?
Zn1 O3 C28 O4 173.30(12) . . . . ?
Zn1 O3 C28 C27 -7.31(16) . . . . ?
N6 C27 C28 O4 -175.17(13) . . . . ?
C26 C27 C28 O4 6.4(2) . . . . ?
N6 C27 C28 O3 5.40(19) . . . . ?
C26 C27 C28 O3 -172.99(14) . . . . ?
N6 C27 C26 C25 -1.8(2) . . . . ?
C28 C27 C26 C25 176.50(14) . . . . ?
C7 N2 C14 C15 155.66(12) . . . . ?
C8A N2 C14 C15 -82.3(3) . . . . ?
C8B N2 C14 C15 -74.4(15) . . . . ?
Zn1 N2 C14 C15 43.77(13) . . . . ?
N4 C15 C14 N2 -65.45(16) . . . . ?
C21 N5 C17 C18 -1.2(2) . . . . ?
C21 N5 C17 C16 176.67(15) . . . . ?
C19 C18 C17 N5 2.4(3) . . . . ?
C19 C18 C17 C16 -175.34(16) . . . . ?
N4 C16 C17 N5 79.85(17) . . . . ?
N4 C16 C17 C18 -102.29(17) . . . . ?
C15 N4 C22 C23 -81.07(15) . . . . ?
C16 N4 C22 C23 152.09(12) . . . . ?
Zn1 N4 C22 C23 30.83(14) . . . . ?
N6 C23 C22 N4 -25.83(18) . . . . ?
C24 C23 C22 N4 156.04(14) . . . . ?
C8A N2 C7 C6 158.6(4) . . . . ?
C14 N2 C7 C6 -76.94(15) . . . . ?
C8B N2 C7 C6 156.9(19) . . . . ?
Zn1 N2 C7 C6 32.62(14) . . . . ?
C2 N1 C6 C5 0.6(2) . . . . ?
Zn1 N1 C6 C5 -179.66(11) . . . . ?
C2 N1 C6 C7 -176.20(13) . . . . ?
Zn1 N1 C6 C7 3.58(17) . . . . ?
N2 C7 C6 N1 -26.63(18) . . . . ?
N2 C7 C6 C5 156.68(14) . . . . ?
N6 C23 C24 C25 -1.5(2) . . . . ?
C22 C23 C24 C25 176.55(15) . . . . ?
C6 N1 C2 C3 -0.7(2) . . . . ?
Zn1 N1 C2 C3 179.49(11) . . . . ?
C6 N1 C2 C1 178.52(12) . . . . ?
Zn1 N1 C2 C1 -1.27(16) . . . . ?
C4 C3 C2 N1 0.2(2) . . . . ?
C4 C3 C2 C1 -178.94(14) . . . . ?
O2 C1 C2 N1 -178.34(13) . . . . ?
O1 C1 C2 N1 1.69(19) . . . . ?
O2 C1 C2 C3 0.9(2) . . . . ?
O1 C1 C2 C3 -179.10(14) . . . . ?
N1 C6 C5 C4 0.1(2) . . . . ?
C7 C6 C5 C4 176.61(14) . . . . ?
C7 N2 C8A C9A 53.1(5) . . . . ?
C14 N2 C8A C9A -70.2(4) . . . . ?
C8B N2 C8A C9A -138(15) . . . . ?
Zn1 N2 C8A C9A 172.1(3) . . . . ?
C6 C5 C4 C3 -0.6(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C17 N5 C21 C20 -1.2(3) . . . . ?
C19 C20 C21 N5 2.3(3) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C27 C26 C25 C24 1.7(2) . . . . ?
C9A N3A C13A C12A 0.3(4) . . . . ?
C11A C12A C13A N3A -2.5(4) . . . . ?
C13A C12A C11A C10A 2.1(4) . . . . ?
C9A C10A C11A C12A 0.3(3) . . . . ?
C21 C20 C19 C18 -1.0(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C13A N3A C9A C10A 2.4(4) . . . . ?
C13A N3A C9A C8A -174.7(4) . . . . ?
C11A C10A C9A N3A -2.7(4) . . . . ?
C11A C10A C9A C8A 174.3(4) . . . . ?
N2 C8A C9A N3A 84.9(5) . . . . ?
N2 C8A C9A C10A -92.2(6) . . . . ?
C9B N3B C13B C12B 0.6(19) . . . . ?
N3B C13B C12B C11B 0(2) . . . . ?
C13B N3B C9B C10B 3(2) . . . . ?
C13B N3B C9B C8B -177(2) . . . . ?
C11B C10B C9B N3B -7(2) . . . . ?
C11B C10B C9B C8B 173(3) . . . . ?
C13B C12B C11B C10B -4(2) . . . . ?
C9B C10B C11B C12B 7.4(19) . . . . ?
N3B C9B C8B N2 111(2) . . . . ?
C10B C9B C8B N2 -69(4) . . . . ?
C7 N2 C8B C9B 66(3) . . . . ?
C8A N2 C8B C9B 54(13) . . . . ?
C14 N2 C8B C9B -61(3) . . . . ?
Zn1 N2 C8B C9B -172.8(18) . . . . ?
