#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226997.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_2226997
loop_
_publ_author_name
'Li, Ke'
'Sun, Tao'
'Yang, Yang'
'Jia, Beibei'
'Wu, Huilu'
_publ_section_title
;
 Aqua(dimethylformamide){tris[(1-methyl-1H-benzimidazol-2-yl)methyl]amine}nickel(II)
 dipicrate
;
_journal_coeditor_code           LH5085
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1025
_journal_paper_doi               10.1107/S1600536810029181
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Ni (C27 H27 N7) (C3 H7 N O) (H2 O)] (C6 H2 N3 O7)2'
_chemical_formula_moiety         'C30 H36 N8 Ni O2 2+, 2(C6 H2 N3 O7 -)'
_chemical_formula_sum            'C42 H40 N14 Ni O16'
_chemical_formula_weight         1055.57
_chemical_name_systematic
;
Aqua(dimethylformamide){tris[(1-methyl-1H-benzimidazol-2-
yl)methyl]amine}nickel(II) dipicrate
;
_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                108.5830(10)
_cell_angle_beta                 95.7030(10)
_cell_angle_gamma                99.5060(10)
_cell_formula_units_Z            2
_cell_length_a                   12.0768(3)
_cell_length_b                   13.2619(4)
_cell_length_c                   15.3544(4)
_cell_measurement_reflns_used    8420
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.2386
_cell_measurement_theta_min      2.4172
_cell_volume                     2268.37(11)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'APEX2 (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
'SHElXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       'ω scans'
_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  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18738
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_T_max  0.9452
_exptl_absorpt_correction_T_min  0.8815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.006
_refine_diff_density_min         -1.237
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         8420
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0499
_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)+(0.0452P)²+5.4011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                5743
_reflns_number_total             8420
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5085.cif
_cod_data_source_block           I
_cod_original_cell_volume        2268.36(11)
_cod_database_code               2226997
_cod_database_fobs_code          2226997
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
Ni Ni 0.46074(4) 0.67214(4) 0.72572(4) 0.02153(16) Uani d . 1 . .
O O1 0.3577(2) 0.7136(2) 0.63281(19) 0.0281(7) Uani d . 1 . .
O O2 0.5213(3) 0.5564(3) 0.6231(2) 0.0274(7) Uani d D 1 . .
O O3 0.6467(3) 0.6084(3) 0.5008(2) 0.0476(10) Uani d . 1 . .
O O4 0.5367(3) 0.6964(4) 0.3971(3) 0.0792(14) Uani d . 1 . .
O O5 0.5862(5) 0.8686(5) 0.4310(4) 0.108(2) Uani d . 1 . .
O O6 0.9546(4) 1.0643(3) 0.5816(3) 0.0661(13) Uani d . 1 . .
O O7 1.0726(4) 0.9877(4) 0.6429(3) 0.0731(14) Uani d . 1 . .
O O8 0.9680(4) 0.6105(4) 0.5949(4) 0.0919(17) Uani d . 1 . .
O O9 0.7967(4) 0.5556(4) 0.6107(4) 0.0843(15) Uani d . 1 . .
O O10 0.2350(3) 0.3427(3) 0.9903(2) 0.0412(8) Uani d . 1 . .
O O11 0.3778(3) 0.5213(3) 0.9850(2) 0.0486(10) Uani d . 1 . .
O O12 0.2960(3) 0.6577(4) 1.0118(3) 0.0670(12) Uani d . 1 . .
O O13 -0.0696(3) 0.6005(3) 0.8309(3) 0.0503(9) Uani d . 1 . .
O O14 -0.1952(3) 0.4559(3) 0.8155(2) 0.0456(9) Uani d . 1 . .
O O15 -0.0703(4) 0.2009(4) 0.9669(3) 0.0758(14) Uani d . 1 . .
O O16 0.0677(4) 0.1511(3) 0.8988(4) 0.0825(16) Uani d . 1 . .
N N1 0.6052(3) 0.7868(3) 0.7367(2) 0.0237(7) Uani d . 1 . .
N N2 0.7876(3) 0.8539(3) 0.7984(2) 0.0234(8) Uani d . 1 . .
N N3 0.3619(3) 0.5380(3) 0.7390(2) 0.0237(8) Uani d . 1 . .
N N4 0.3585(3) 0.3892(3) 0.7762(2) 0.0248(8) Uani d . 1 . .
N N5 0.4158(3) 0.7756(3) 0.8396(2) 0.0237(8) Uani d . 1 . .
N N6 0.4450(3) 0.8522(3) 0.9935(2) 0.0251(8) Uani d . 1 . .
N N7 0.5741(3) 0.6426(3) 0.8305(2) 0.0206(7) Uani d . 1 . .
N N8 0.2926(3) 0.7234(3) 0.4929(2) 0.0321(9) Uani d . 1 . .
N N9 0.6035(4) 0.7845(5) 0.4381(3) 0.0539(13) Uani d . 1 . .
N N10 0.9804(4) 0.9860(4) 0.5993(3) 0.0495(12) Uani d . 1 . .
N N11 0.8678(4) 0.6177(4) 0.5921(3) 0.0481(11) Uani d . 1 . .
N N12 0.2919(3) 0.5600(4) 0.9830(3) 0.0397(10) Uani d . 1 . .
N N13 -0.0966(3) 0.5105(3) 0.8384(3) 0.0349(9) Uani d . 1 . .
N N14 0.0128(4) 0.2193(4) 0.9307(3) 0.0484(12) Uani d . 1 . .
C C1 0.6383(3) 0.8840(3) 0.7211(3) 0.0231(9) Uani d . 1 . .
C C2 0.5753(4) 0.9402(3) 0.6782(3) 0.0281(10) Uani d . 1 . .
H H2B 0.4972 0.9119 0.6520 0.034 Uiso calc R 1 . .
C C3 0.6314(4) 1.0377(4) 0.6758(3) 0.0357(11) Uani d . 1 . .
H H3A 0.5911 1.0781 0.6477 0.043 Uiso calc R 1 . .
C C4 0.7468(4) 1.0795(4) 0.7138(4) 0.0380(11) Uani d . 1 . .
H H4A 0.7826 1.1472 0.7103 0.046 Uiso calc R 1 . .
C C5 0.8102(4) 1.0252(4) 0.7563(3) 0.0339(11) Uani d . 1 . .
H H5A 0.8883 1.0535 0.7822 0.041 Uiso calc R 1 . .
C C6 0.7524(3) 0.9264(3) 0.7589(3) 0.0255(9) Uani d . 1 . .
C C7 0.6969(3) 0.7732(3) 0.7840(3) 0.0232(9) Uani d . 1 . .
C C8 0.6925(3) 0.6766(3) 0.8150(3) 0.0250(9) Uani d . 1 . .
H H8A 0.7136 0.6163 0.7667 0.030 Uiso calc R 1 . .
H H8B 0.7468 0.6956 0.8733 0.030 Uiso calc R 1 . .
C C9 0.5451(3) 0.5244(3) 0.8168(3) 0.0262(9) Uani d . 1 . .
H H9A 0.5623 0.5127 0.8768 0.031 Uiso calc R 1 . .
H H9B 0.5903 0.4844 0.7727 0.031 Uiso calc R 1 . .
C C10 0.4205(3) 0.4843(3) 0.7788(3) 0.0248(9) Uani d . 1 . .
C C11 0.2494(3) 0.3800(3) 0.7303(3) 0.0230(9) Uani d . 1 . .
C C12 0.1523(4) 0.2984(4) 0.7074(3) 0.0305(10) Uani d . 1 . .
H H12A 0.1515 0.2337 0.7218 0.037 Uiso calc R 1 . .
C C13 0.0562(4) 0.3171(4) 0.6622(3) 0.0318(10) Uani d . 1 . .
H H13A -0.0127 0.2640 0.6453 0.038 Uiso calc R 1 . .
C C14 0.0588(4) 0.4132(4) 0.6410(3) 0.0318(10) Uani d . 1 . .
H H14A -0.0084 0.4232 0.6100 0.038 Uiso calc R 1 . .
C C15 0.1555(3) 0.4924(3) 0.6637(3) 0.0265(9) Uani d . 1 . .
H H15A 0.1565 0.5572 0.6496 0.032 Uiso calc R 1 . .
C C16 0.2530(3) 0.4742(3) 0.7088(3) 0.0232(9) Uani d . 1 . .
C C17 0.5556(4) 0.7092(4) 0.9249(3) 0.0279(10) Uani d . 1 . .
H H17A 0.5276 0.6601 0.9585 0.033 Uiso calc R 1 . .
H H17B 0.6291 0.7560 0.9610 0.033 Uiso calc R 1 . .
C C18 0.4724(3) 0.7786(3) 0.9191(3) 0.0221(9) Uani d . 1 . .
C C19 0.3643(3) 0.8988(3) 0.9595(3) 0.0263(9) Uani d . 1 . .
C C20 0.3085(4) 0.9796(4) 1.0048(3) 0.0350(11) Uani d . 1 . .
H H20A 0.3210 1.0117 1.0707 0.042 Uiso calc R 1 . .
C C21 0.2339(4) 1.0103(4) 0.9487(3) 0.0344(11) Uani d . 1 . .
H H21A 0.1947 1.0658 0.9765 0.041 Uiso calc R 1 . .
C C22 0.2151(4) 0.9617(4) 0.8520(3) 0.0360(11) Uani d . 1 . .
H H22A 0.1627 0.9845 0.8158 0.043 Uiso calc R 1 . .
C C23 0.2704(3) 0.8811(4) 0.8072(3) 0.0313(10) Uani d . 1 . .
H H23A 0.2569 0.8482 0.7413 0.038 Uiso calc R 1 . .
C C24 0.3464(3) 0.8508(3) 0.8632(3) 0.0233(9) Uani d . 1 . .
C C25 0.9037(4) 0.8644(4) 0.8443(3) 0.0360(11) Uani d . 1 . .
H H25A 0.9067 0.8029 0.8661 0.054 Uiso calc R 1 . .
H H25B 0.9253 0.9326 0.8975 0.054 Uiso calc R 1 . .
H H25C 0.9567 0.8648 0.7999 0.054 Uiso calc R 1 . .
C C26 0.3955(4) 0.3098(4) 0.8132(3) 0.0334(10) Uani d . 1 . .
H H26A 0.4758 0.3358 0.8419 0.050 Uiso calc R 1 . .
H H26B 0.3863 0.2402 0.7625 0.050 Uiso calc R 1 . .
H H26C 0.3494 0.2999 0.8600 0.050 Uiso calc R 1 . .
C C27 0.4860(4) 0.8732(4) 1.0919(3) 0.0327(10) Uani d . 1 . .
H H27A 0.5429 0.8297 1.0971 0.049 Uiso calc R 1 . .
H H27B 0.4221 0.8534 1.1220 0.049 Uiso calc R 1 . .
H H27C 0.5205 0.9506 1.1226 0.049 Uiso calc R 1 . .
C C28 0.3449(3) 0.6785(3) 0.5465(3) 0.0247(9) Uani d . 1 . .
H H28A 0.3740 0.6161 0.5172 0.030 Uiso calc R 1 . .
C C29 0.2483(7) 0.8196(6) 0.5310(4) 0.088(3) Uani d . 1 . .
H H29A 0.2621 0.8427 0.5992 0.132 Uiso calc R 1 . .
H H29B 0.1662 0.8037 0.5087 0.132 Uiso calc R 1 . .
H H29C 0.2862 0.8778 0.5112 0.132 Uiso calc R 1 . .
C C30 0.2785(4) 0.6789(4) 0.3916(3) 0.0319(10) Uani d . 1 . .
H H30A 0.3109 0.6136 0.3730 0.048 Uiso calc R 1 . .
H H30B 0.3177 0.7333 0.3682 0.048 Uiso calc R 1 . .
H H30C 0.1973 0.6598 0.3656 0.048 Uiso calc R 1 . .
C C31 0.7227(4) 0.6930(4) 0.5180(3) 0.0322(10) Uani d . 1 . .
C C32 0.7101(4) 0.7865(4) 0.4924(3) 0.0310(10) Uani d . 1 . .
C C33 0.7918(4) 0.8803(4) 0.5177(3) 0.0354(11) Uani d . 1 . .
H H33A 0.7775 0.9406 0.5010 0.042 Uiso calc R 1 . .
C C34 0.8956(4) 0.8854(4) 0.5681(3) 0.0311(10) Uani d . 1 . .
C C35 0.9189(4) 0.7981(4) 0.5902(3) 0.0323(10) Uani d . 1 . .
H H35A 0.9920 0.8014 0.6216 0.039 Uiso calc R 1 . .
C C36 0.8360(4) 0.7063(4) 0.5667(3) 0.0302(10) Uani d . 1 . .
C C37 0.1626(4) 0.3812(4) 0.9551(3) 0.0298(10) Uani d . 1 . .
C C38 0.1809(3) 0.4884(4) 0.9463(3) 0.0313(10) Uani d . 1 . .
C C39 0.0991(4) 0.5297(4) 0.9091(3) 0.0294(10) Uani d . 1 . .
H H39A 0.1170 0.6003 0.9048 0.035 Uiso calc R 1 . .
C C40 -0.0101(3) 0.4675(4) 0.8779(3) 0.0275(10) Uani d . 1 . .
C C41 -0.0389(4) 0.3658(4) 0.8866(3) 0.0326(11) Uani d . 1 . .
H H41A -0.1149 0.3250 0.8678 0.039 Uiso calc R 1 . .
C C42 0.0447(4) 0.3260(4) 0.9229(3) 0.0291(10) Uani d . 1 . .
H H2D 0.569(4) 0.575(5) 0.590(4) 0.07(2) Uiso d D 1 . .
H H2C 0.479(5) 0.496(3) 0.590(4) 0.10(3) Uiso d D 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'
Ni Ni 0.3393 1.1124 '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'
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
N5 Ni N3 . . 92.81(14) ?
N5 Ni O1 . . 93.80(12) ?
N3 Ni O1 . . 104.09(12) ?
N5 Ni N1 . . 90.52(13) ?
N3 Ni N1 . . 158.76(13) ?
O1 Ni N1 . . 96.60(13) ?
N5 Ni O2 . . 170.87(13) ?
N3 Ni O2 . . 84.00(13) ?
O1 Ni O2 . . 95.28(12) ?
N1 Ni O2 . . 89.44(13) ?
N5 Ni N7 . . 82.85(13) ?
N3 Ni N7 . . 79.47(12) ?
O1 Ni N7 . . 175.27(12) ?
N1 Ni N7 . . 80.16(13) ?
O2 Ni N7 . . 88.15(12) ?
C28 O1 Ni . . 128.2(3) ?
Ni O2 H2D . . 122(4) ?
Ni O2 H2C . . 121(5) ?
H2D O2 H2C . . 108(6) ?
O3 O3 C31 1 . 0(10) ?
C7 N1 C1 . . 105.8(3) ?
C7 N1 Ni . . 112.8(3) ?
C1 N1 Ni . . 140.8(3) ?
C7 N2 C6 . . 106.9(3) ?
C7 N2 C25 . . 127.8(4) ?
C6 N2 C25 . . 125.3(4) ?
C10 N3 C16 . . 105.7(4) ?
C10 N3 Ni . . 113.2(3) ?
C16 N3 Ni . . 140.4(3) ?
C10 N4 C11 . . 106.6(3) ?
C10 N4 C26 . . 127.6(3) ?
C11 N4 C26 . . 125.8(3) ?
C18 N5 C24 . . 106.2(3) ?
C18 N5 Ni . . 113.2(3) ?
C24 N5 Ni . . 140.6(3) ?
C18 N6 C19 . . 107.2(3) ?
C18 N6 C27 . . 126.9(4) ?
C19 N6 C27 . . 125.8(3) ?
C9 N7 C8 . . 111.9(3) ?
C9 N7 C17 . . 110.7(3) ?
C8 N7 C17 . . 111.3(3) ?
C9 N7 Ni . . 107.7(2) ?
C8 N7 Ni . . 106.6(2) ?
C17 N7 Ni . . 108.4(2) ?
C28 N8 C29 . . 122.1(4) ?
C28 N8 C30 . . 121.8(4) ?
C29 N8 C30 . . 116.0(4) ?
O5 N9 O4 . . 122.3(5) ?
O5 N9 C32 . . 118.3(5) ?
O4 N9 C32 . . 119.3(5) ?
O6 N10 O7 . . 124.6(5) ?
O6 N10 C34 . . 117.6(5) ?
O7 N10 C34 . . 117.7(5) ?
O9 N11 O8 . . 122.9(5) ?
O9 N11 C36 . . 119.7(5) ?
O8 N11 C36 . . 117.4(5) ?
O12 N12 O11 . . 122.3(4) ?
O12 N12 C38 . . 117.8(4) ?
O11 N12 C38 . . 119.9(4) ?
O13 N13 O14 . . 123.1(4) ?
O13 N13 C40 . . 118.5(4) ?
O14 N13 C40 . . 118.4(4) ?
O16 N14 O15 . . 122.8(5) ?
O16 N14 C42 . . 118.8(5) ?
O15 N14 C42 . . 118.4(5) ?
N1 C1 C6 . . 108.8(4) ?
N1 C1 C2 . . 130.5(4) ?
C6 C1 C2 . . 120.8(4) ?
C3 C2 C1 . . 117.0(4) ?
C3 C2 H2B . . 121.5 ?
C1 C2 H2B . . 121.5 ?
C2 C3 C4 . . 121.7(4) ?
C2 C3 H3A . . 119.1 ?
C4 C3 H3A . . 119.1 ?
C5 C4 C3 . . 122.0(4) ?
C5 C4 H4A . . 119.0 ?
C3 C4 H4A . . 119.0 ?
C4 C5 C6 . . 115.9(4) ?
C4 C5 H5A . . 122.0 ?
C6 C5 H5A . . 122.0 ?
N2 C6 C1 . . 106.2(4) ?
N2 C6 C5 . . 131.1(4) ?
C1 C6 C5 . . 122.6(4) ?
N1 C7 N2 . . 112.3(4) ?
N1 C7 C8 . . 120.9(4) ?
N2 C7 C8 . . 126.8(3) ?
N7 C8 C7 . . 108.1(3) ?
N7 C8 H8A . . 110.1 ?
C7 C8 H8A . . 110.1 ?
N7 C8 H8B . . 110.1 ?
C7 C8 H8B . . 110.1 ?
H8A C8 H8B . . 108.4 ?
N7 C9 C10 . . 107.8(3) ?
N7 C9 H9A . . 110.1 ?
C10 C9 H9A . . 110.1 ?
N7 C9 H9B . . 110.1 ?
C10 C9 H9B . . 110.1 ?
H9A C9 H9B . . 108.5 ?
N3 C10 N4 . . 112.9(4) ?
N3 C10 C9 . . 122.2(4) ?
N4 C10 C9 . . 124.8(4) ?
C16 C11 C12 . . 123.0(4) ?
C16 C11 N4 . . 105.7(3) ?
C12 C11 N4 . . 131.3(4) ?
C11 C12 C13 . . 115.9(4) ?
C11 C12 H12A . . 122.0 ?
C13 C12 H12A . . 122.0 ?
C12 C13 C14 . . 121.4(4) ?
C12 C13 H13A . . 119.3 ?
C14 C13 H13A . . 119.3 ?
C15 C14 C13 . . 121.8(4) ?
C15 C14 H14A . . 119.1 ?
C13 C14 H14A . . 119.1 ?
C14 C15 C16 . . 117.4(4) ?
C14 C15 H15A . . 121.3 ?
C16 C15 H15A . . 121.3 ?
C11 C16 N3 . . 109.2(4) ?
C11 C16 C15 . . 120.5(4) ?
N3 C16 C15 . . 130.3(4) ?
C18 C17 N7 . . 112.0(3) ?
C18 C17 H17A . . 109.2 ?
N7 C17 H17A . . 109.2 ?
C18 C17 H17B . . 109.2 ?
N7 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
N5 C18 N6 . . 111.8(3) ?
N5 C18 C17 . . 123.5(4) ?
N6 C18 C17 . . 124.7(3) ?
N6 C19 C24 . . 106.3(3) ?
N6 C19 C20 . . 131.3(4) ?
C24 C19 C20 . . 122.3(4) ?
C21 C20 C19 . . 116.4(4) ?
C21 C20 H20A . . 121.8 ?
C19 C20 H20A . . 121.8 ?
C20 C21 C22 . . 121.4(4) ?
C20 C21 H21A . . 119.3 ?
C22 C21 H21A . . 119.3 ?
C23 C22 C21 . . 122.1(4) ?
C23 C22 H22A . . 119.0 ?
C21 C22 H22A . . 119.0 ?
C22 C23 C24 . . 116.8(4) ?
C22 C23 H23A . . 121.6 ?
C24 C23 H23A . . 121.6 ?
C19 C24 C23 . . 121.0(4) ?
C19 C24 N5 . . 108.5(3) ?
C23 C24 N5 . . 130.5(4) ?
N2 C25 H25A . . 109.5 ?
N2 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
N2 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
N4 C26 H26A . . 109.5 ?
N4 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
N4 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
N6 C27 H27A . . 109.5 ?
N6 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
N6 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
O1 C28 N8 . . 123.7(4) ?
O1 C28 H28A . . 118.2 ?
N8 C28 H28A . . 118.2 ?
N8 C29 H29A . . 109.5 ?
N8 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
N8 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
N8 C30 H30A . . 109.5 ?
N8 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
N8 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
O3 C31 O3 1 . 0.0(4) ?
O3 C31 C32 1 . 125.8(4) ?
O3 C31 C32 . . 125.8(4) ?
O3 C31 C36 1 . 122.6(4) ?
O3 C31 C36 . . 122.6(4) ?
C32 C31 C36 . . 111.6(4) ?
C33 C32 C31 . . 124.4(4) ?
C33 C32 N9 . . 116.6(5) ?
C31 C32 N9 . . 119.0(4) ?
C32 C33 C34 . . 118.7(4) ?
C32 C33 H33A . . 120.7 ?
C34 C33 H33A . . 120.7 ?
C35 C34 C33 . . 121.4(4) ?
C35 C34 N10 . . 119.4(4) ?
C33 C34 N10 . . 119.1(4) ?
C36 C35 C34 . . 119.2(4) ?
C36 C35 H35A . . 120.4 ?
C34 C35 H35A . . 120.4 ?
C35 C36 N11 . . 115.7(4) ?
C35 C36 C31 . . 124.5(4) ?
N11 C36 C31 . . 119.8(4) ?
O10 C37 C42 . . 123.3(4) ?
O10 C37 C38 . . 125.8(4) ?
C42 C37 C38 . . 110.7(4) ?
C39 C38 N12 . . 116.6(4) ?
C39 C38 C37 . . 124.7(4) ?
N12 C38 C37 . . 118.7(4) ?
C38 C39 C40 . . 119.2(4) ?
C38 C39 H39A . . 120.4 ?
C40 C39 H39A . . 120.4 ?
C39 C40 C41 . . 121.3(4) ?
C39 C40 N13 . . 119.4(4) ?
C41 C40 N13 . . 119.3(4) ?
C42 C41 C40 . . 118.3(4) ?
C42 C41 H41A . . 120.8 ?
C40 C41 H41A . . 120.8 ?
C41 C42 C37 . . 125.8(4) ?
C41 C42 N14 . . 117.4(4) ?
C37 C42 N14 . . 116.9(4) ?
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
Ni N5 . 2.035(3) ?
Ni N3 . 2.052(4) ?
Ni O1 . 2.063(3) ?
Ni N1 . 2.071(3) ?
Ni O2 . 2.106(3) ?
Ni N7 . 2.181(3) ?
O1 C28 . 1.240(5) ?
O2 H2D . 0.86(2) ?
O2 H2C . 0.85(2) ?
O3 O3 1 0.000(9) ?
O3 C31 . 1.263(5) ?
O4 N9 . 1.237(6) ?
O5 N9 . 1.204(7) ?
O6 N10 . 1.232(6) ?
O7 N10 . 1.234(6) ?
O8 N11 . 1.227(6) ?
O9 N11 . 1.209(6) ?
O10 C37 . 1.244(5) ?
O11 N12 . 1.233(5) ?
O12 N12 . 1.219(6) ?
O13 N13 . 1.230(5) ?
O14 N13 . 1.239(5) ?
O15 N14 . 1.221(6) ?
O16 N14 . 1.216(6) ?
N1 C7 . 1.333(5) ?
N1 C1 . 1.387(5) ?
N2 C7 . 1.345(5) ?
N2 C6 . 1.388(5) ?
N2 C25 . 1.470(5) ?
N3 C10 . 1.318(5) ?
N3 C16 . 1.387(5) ?
N4 C10 . 1.343(5) ?
N4 C11 . 1.399(5) ?
N4 C26 . 1.455(5) ?
N5 C18 . 1.324(5) ?
N5 C24 . 1.390(5) ?
N6 C18 . 1.355(5) ?
N6 C19 . 1.381(5) ?
N6 C27 . 1.465(5) ?
N7 C9 . 1.490(5) ?
N7 C8 . 1.493(5) ?
N7 C17 . 1.498(5) ?
N8 C28 . 1.329(5) ?
N8 C29 . 1.438(7) ?
N8 C30 . 1.457(5) ?
N9 C32 . 1.454(6) ?
N10 C34 . 1.450(6) ?
N11 C36 . 1.446(6) ?
N12 C38 . 1.450(6) ?
N13 C40 . 1.441(5) ?
N14 C42 . 1.450(6) ?
C1 C6 . 1.388(6) ?
C1 C2 . 1.403(6) ?
C2 C3 . 1.371(6) ?
C2 H2B . 0.9500 ?
C3 C4 . 1.403(7) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.383(7) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.394(6) ?
C5 H5A . 0.9500 ?
C7 C8 . 1.498(6) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.500(6) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C11 C16 . 1.384(6) ?
C11 C12 . 1.388(6) ?
C12 C13 . 1.391(6) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.409(6) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.366(6) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.401(6) ?
C15 H15A . 0.9500 ?
C17 C18 . 1.485(6) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C19 C24 . 1.389(6) ?
C19 C20 . 1.394(6) ?
C20 C21 . 1.382(6) ?
C20 H20A . 0.9500 ?
C21 C22 . 1.395(6) ?
C21 H21A . 0.9500 ?
C22 C23 . 1.385(6) ?
C22 H22A . 0.9500 ?
C23 C24 . 1.390(6) ?
C23 H23A . 0.9500 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
C28 H28A . 0.9500 ?
C29 H29A . 0.9800 ?
C29 H29B . 0.9800 ?
C29 H29C . 0.9800 ?
C30 H30A . 0.9800 ?
C30 H30B . 0.9800 ?
C30 H30C . 0.9800 ?
C31 O3 1 1.263(5) ?
C31 C32 . 1.441(7) ?
C31 C36 . 1.447(6) ?
C32 C33 . 1.372(7) ?
C33 C34 . 1.386(7) ?
C33 H33A . 0.9500 ?
C34 C35 . 1.369(6) ?
C35 C36 . 1.364(6) ?
C35 H35A . 0.9500 ?
C37 C42 . 1.446(6) ?
C37 C38 . 1.454(7) ?
C38 C39 . 1.367(6) ?
C39 C40 . 1.382(6) ?
C39 H39A . 0.9500 ?
C40 C41 . 1.388(7) ?
C41 C42 . 1.363(6) ?
C41 H41A . 0.9500 ?
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
O2 H2D O3 1 0.86(2) 1.86(2) 2.708(4) 169(6)
O2 H2C O3 2_666 0.85(2) 1.95(3) 2.763(4) 160(7)
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
N5 Ni O1 C28 . . . . 179.5(3) ?
N3 Ni O1 C28 . . . . -86.7(4) ?
N1 Ni O1 C28 . . . . 88.5(4) ?
O2 Ni O1 C28 . . . . -1.6(4) ?
N7 Ni O1 C28 . . . . 134.9(14) ?
N5 Ni N1 C7 . . . . 94.7(3) ?
N3 Ni N1 C7 . . . . -4.4(5) ?
O1 Ni N1 C7 . . . . -171.4(3) ?
O2 Ni N1 C7 . . . . -76.2(3) ?
N7 Ni N1 C7 . . . . 12.1(3) ?
N5 Ni N1 C1 . . . . -74.3(4) ?
N3 Ni N1 C1 . . . . -173.4(4) ?
O1 Ni N1 C1 . . . . 19.6(4) ?
O2 Ni N1 C1 . . . . 114.8(4) ?
N7 Ni N1 C1 . . . . -156.9(5) ?
N5 Ni N3 C10 . . . . -100.0(3) ?
O1 Ni N3 C10 . . . . 165.4(3) ?
N1 Ni N3 C10 . . . . -1.3(6) ?
O2 Ni N3 C10 . . . . 71.4(3) ?
N7 Ni N3 C10 . . . . -17.8(3) ?
N5 Ni N3 C16 . . . . 91.7(4) ?
O1 Ni N3 C16 . . . . -2.9(4) ?
N1 Ni N3 C16 . . . . -169.6(4) ?
O2 Ni N3 C16 . . . . -96.9(4) ?
N7 Ni N3 C16 . . . . 173.9(4) ?
N3 Ni N5 C18 . . . . 79.7(3) ?
O1 Ni N5 C18 . . . . -175.9(3) ?
N1 Ni N5 C18 . . . . -79.3(3) ?
O2 Ni N5 C18 . . . . 10.5(10) ?
N7 Ni N5 C18 . . . . 0.7(3) ?
N3 Ni N5 C24 . . . . -104.1(4) ?
O1 Ni N5 C24 . . . . 0.2(4) ?
N1 Ni N5 C24 . . . . 96.9(4) ?
O2 Ni N5 C24 . . . . -173.4(7) ?
N7 Ni N5 C24 . . . . 176.9(4) ?
N5 Ni N7 C9 . . . . 121.3(3) ?
N3 Ni N7 C9 . . . . 27.1(2) ?
O1 Ni N7 C9 . . . . 166.3(14) ?
N1 Ni N7 C9 . . . . -146.9(3) ?
O2 Ni N7 C9 . . . . -57.1(3) ?
N5 Ni N7 C8 . . . . -118.4(3) ?
N3 Ni N7 C8 . . . . 147.3(3) ?
O1 Ni N7 C8 . . . . -73.5(15) ?
N1 Ni N7 C8 . . . . -26.6(2) ?
O2 Ni N7 C8 . . . . 63.1(2) ?
N5 Ni N7 C17 . . . . 1.5(3) ?
N3 Ni N7 C17 . . . . -92.8(3) ?
O1 Ni N7 C17 . . . . 46.4(16) ?
N1 Ni N7 C17 . . . . 93.2(3) ?
O2 Ni N7 C17 . . . . -177.0(3) ?
C7 N1 C1 C6 . . . . 1.1(4) ?
Ni N1 C1 C6 . . . . 170.6(3) ?
C7 N1 C1 C2 . . . . -177.1(4) ?
Ni N1 C1 C2 . . . . -7.6(8) ?
N1 C1 C2 C3 . . . . 177.8(4) ?
C6 C1 C2 C3 . . . . -0.2(6) ?
C1 C2 C3 C4 . . . . 0.4(7) ?
C2 C3 C4 C5 . . . . -0.5(8) ?
C3 C4 C5 C6 . . . . 0.2(7) ?
C7 N2 C6 C1 . . . . -0.2(4) ?
C25 N2 C6 C1 . . . . 178.2(4) ?
C7 N2 C6 C5 . . . . 177.5(4) ?
C25 N2 C6 C5 . . . . -4.1(7) ?
N1 C1 C6 N2 . . . . -0.6(5) ?
C2 C1 C6 N2 . . . . 177.8(4) ?
N1 C1 C6 C5 . . . . -178.5(4) ?
C2 C1 C6 C5 . . . . -0.1(6) ?
C4 C5 C6 N2 . . . . -177.2(4) ?
C4 C5 C6 C1 . . . . 0.1(7) ?
C1 N1 C7 N2 . . . . -1.3(5) ?
Ni N1 C7 N2 . . . . -174.1(3) ?
C1 N1 C7 C8 . . . . 178.9(4) ?
Ni N1 C7 C8 . . . . 6.1(5) ?
C6 N2 C7 N1 . . . . 1.0(5) ?
C25 N2 C7 N1 . . . . -177.4(4) ?
C6 N2 C7 C8 . . . . -179.3(4) ?
C25 N2 C7 C8 . . . . 2.4(7) ?
C9 N7 C8 C7 . . . . 152.8(3) ?
C17 N7 C8 C7 . . . . -82.8(4) ?
Ni N7 C8 C7 . . . . 35.2(4) ?
N1 C7 C8 N7 . . . . -29.5(5) ?
N2 C7 C8 N7 . . . . 150.7(4) ?
C8 N7 C9 C10 . . . . -147.5(3) ?
C17 N7 C9 C10 . . . . 87.8(4) ?
Ni N7 C9 C10 . . . . -30.6(4) ?
C16 N3 C10 N4 . . . . 0.6(5) ?
Ni N3 C10 N4 . . . . -171.7(3) ?
C16 N3 C10 C9 . . . . 177.0(4) ?
Ni N3 C10 C9 . . . . 4.7(5) ?
C11 N4 C10 N3 . . . . 0.2(5) ?
C26 N4 C10 N3 . . . . -180.0(4) ?
C11 N4 C10 C9 . . . . -176.2(4) ?
C26 N4 C10 C9 . . . . 3.7(7) ?
N7 C9 C10 N3 . . . . 19.0(5) ?
N7 C9 C10 N4 . . . . -165.0(4) ?
C10 N4 C11 C16 . . . . -0.9(4) ?
C26 N4 C11 C16 . . . . 179.3(4) ?
C10 N4 C11 C12 . . . . 179.2(4) ?
C26 N4 C11 C12 . . . . -0.6(7) ?
C16 C11 C12 C13 . . . . -1.0(6) ?
N4 C11 C12 C13 . . . . 178.9(4) ?
C11 C12 C13 C14 . . . . 0.3(7) ?
C12 C13 C14 C15 . . . . -0.1(7) ?
C13 C14 C15 C16 . . . . 0.4(7) ?
C12 C11 C16 N3 . . . . -178.8(4) ?
N4 C11 C16 N3 . . . . 1.3(4) ?
C12 C11 C16 C15 . . . . 1.4(6) ?
N4 C11 C16 C15 . . . . -178.5(4) ?
C10 N3 C16 C11 . . . . -1.1(5) ?
Ni N3 C16 C11 . . . . 167.7(3) ?
C10 N3 C16 C15 . . . . 178.6(4) ?
Ni N3 C16 C15 . . . . -12.5(7) ?
C14 C15 C16 C11 . . . . -1.0(6) ?
C14 C15 C16 N3 . . . . 179.2(4) ?
C9 N7 C17 C18 . . . . -121.2(4) ?
C8 N7 C17 C18 . . . . 113.8(4) ?
Ni N7 C17 C18 . . . . -3.2(4) ?
C24 N5 C18 N6 . . . . -0.6(5) ?
Ni N5 C18 N6 . . . . 176.9(3) ?
C24 N5 C18 C17 . . . . 179.4(4) ?
Ni N5 C18 C17 . . . . -3.1(5) ?
C19 N6 C18 N5 . . . . 0.7(5) ?
C27 N6 C18 N5 . . . . 176.5(4) ?
C19 N6 C18 C17 . . . . -179.3(4) ?
C27 N6 C18 C17 . . . . -3.6(7) ?
N7 C17 C18 N5 . . . . 4.4(6) ?
N7 C17 C18 N6 . . . . -175.5(4) ?
C18 N6 C19 C24 . . . . -0.5(5) ?
C27 N6 C19 C24 . . . . -176.3(4) ?
C18 N6 C19 C20 . . . . -178.9(5) ?
C27 N6 C19 C20 . . . . 5.2(8) ?
N6 C19 C20 C21 . . . . 177.9(5) ?
C24 C19 C20 C21 . . . . -0.3(7) ?
C19 C20 C21 C22 . . . . 0.8(7) ?
C20 C21 C22 C23 . . . . -0.6(8) ?
C21 C22 C23 C24 . . . . -0.2(7) ?
N6 C19 C24 C23 . . . . -179.1(4) ?
C20 C19 C24 C23 . . . . -0.5(7) ?
N6 C19 C24 N5 . . . . 0.1(5) ?
C20 C19 C24 N5 . . . . 178.8(4) ?
C22 C23 C24 C19 . . . . 0.7(7) ?
C22 C23 C24 N5 . . . . -178.3(4) ?
C18 N5 C24 C19 . . . . 0.3(5) ?
Ni N5 C24 C19 . . . . -176.0(3) ?
C18 N5 C24 C23 . . . . 179.4(5) ?
Ni N5 C24 C23 . . . . 3.1(8) ?
Ni O1 C28 N8 . . . . -167.6(3) ?
C29 N8 C28 O1 . . . . 1.6(8) ?
C30 N8 C28 O1 . . . . -179.4(4) ?
O3 O3 C31 C32 1 . . . 0.00(4) ?
O3 O3 C31 C36 1 . . . 0.00(17) ?
O3 C31 C32 C33 1 . . . 175.3(4) ?
O3 C31 C32 C33 . . . . 175.3(4) ?
C36 C31 C32 C33 . . . . -5.2(6) ?
O3 C31 C32 N9 1 . . . -3.0(7) ?
O3 C31 C32 N9 . . . . -3.0(7) ?
C36 C31 C32 N9 . . . . 176.5(4) ?
O5 N9 C32 C33 . . . . -11.2(7) ?
O4 N9 C32 C33 . . . . 165.0(5) ?
O5 N9 C32 C31 . . . . 167.2(5) ?
O4 N9 C32 C31 . . . . -16.6(7) ?
C31 C32 C33 C34 . . . . 2.7(7) ?
N9 C32 C33 C34 . . . . -178.9(4) ?
C32 C33 C34 C35 . . . . 2.1(7) ?
C32 C33 C34 N10 . . . . -176.9(4) ?
O6 N10 C34 C35 . . . . -176.9(4) ?
O7 N10 C34 C35 . . . . 2.0(7) ?
O6 N10 C34 C33 . . . . 2.1(7) ?
O7 N10 C34 C33 . . . . -179.0(4) ?
C33 C34 C35 C36 . . . . -3.8(7) ?
N10 C34 C35 C36 . . . . 175.2(4) ?
C34 C35 C36 N11 . . . . 179.7(4) ?
C34 C35 C36 C31 . . . . 0.7(7) ?
O9 N11 C36 C35 . . . . 149.3(5) ?
O8 N11 C36 C35 . . . . -29.7(7) ?
O9 N11 C36 C31 . . . . -31.7(7) ?
O8 N11 C36 C31 . . . . 149.3(5) ?
O3 C31 C36 C35 1 . . . -177.0(4) ?
O3 C31 C36 C35 . . . . -177.0(4) ?
C32 C31 C36 C35 . . . . 3.5(6) ?
O3 C31 C36 N11 1 . . . 4.1(7) ?
O3 C31 C36 N11 . . . . 4.1(7) ?
C32 C31 C36 N11 . . . . -175.4(4) ?
O12 N12 C38 C39 . . . . 27.7(6) ?
O11 N12 C38 C39 . . . . -152.9(4) ?
O12 N12 C38 C37 . . . . -149.4(5) ?
O11 N12 C38 C37 . . . . 29.9(6) ?
O10 C37 C38 C39 . . . . -178.5(4) ?
C42 C37 C38 C39 . . . . -2.4(6) ?
O10 C37 C38 N12 . . . . -1.6(7) ?
C42 C37 C38 N12 . . . . 174.5(4) ?
N12 C38 C39 C40 . . . . -176.3(4) ?
C37 C38 C39 C40 . . . . 0.7(7) ?
C38 C39 C40 C41 . . . . 2.3(6) ?
C38 C39 C40 N13 . . . . -179.8(4) ?
O13 N13 C40 C39 . . . . 2.2(6) ?
O14 N13 C40 C39 . . . . -176.2(4) ?
O13 N13 C40 C41 . . . . -179.8(4) ?
O14 N13 C40 C41 . . . . 1.8(6) ?
C39 C40 C41 C42 . . . . -3.0(6) ?
N13 C40 C41 C42 . . . . 179.0(4) ?
C40 C41 C42 C37 . . . . 1.0(7) ?
C40 C41 C42 N14 . . . . -179.6(4) ?
O10 C37 C42 C41 . . . . 177.8(4) ?
C38 C37 C42 C41 . . . . 1.6(6) ?
O10 C37 C42 N14 . . . . -1.6(7) ?
C38 C37 C42 N14 . . . . -177.8(4) ?
O16 N14 C42 C41 . . . . 128.6(5) ?
O15 N14 C42 C41 . . . . -49.3(6) ?
O16 N14 C42 C37 . . . . -51.9(6) ?
O15 N14 C42 C37 . . . . 130.2(5) ?
