#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/24/2222406.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_2222406
loop_
_publ_author_name
'Ou, Guang-Chuan'
'Zhang, Min'
'Yuan, Xian-You'
_publ_section_title
;(2-Carboxybenzoato-κ²O¹,O^1'^)(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ⁴N)nickel(II)
 perchlorate monohydrate
;
_journal_coeditor_code           NG2586
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m726
_journal_paper_doi               10.1107/S1600536809020169
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Ni (C8 H5 O4) (C16 H36 N4)] Cl O4, H2 O'
_chemical_formula_moiety         'C24 H41 N4 Ni O4 +, Cl O4 -, H2 O1'
_chemical_formula_sum            'C24 H43 Cl N4 Ni O9'
_chemical_formula_weight         625.78
_chemical_name_systematic
;
(2-Carboxybenzoato-κ²O¹,O^1'^)(5,5,7,12,12,14-hexamethyl-
1,4,8,11-tetraazacyclotetradecane-κ⁴N)nickel(II) perchlorate
monohydrate
;
_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                 102.105(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7941(12)
_cell_length_b                   17.354(2)
_cell_length_c                   17.619(2)
_cell_measurement_reflns_used    5283
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.35
_cell_volume                     2928.1(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14639
_diffrn_reflns_theta_full        27.06
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  0.8681
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.419
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         6322
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0858P)²+1.13P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                4597
_reflns_number_total             6322
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2586.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        2928.2(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222406
_cod_database_fobs_code          2222406
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.32081(4) 0.21532(2) 0.13185(2) 0.02393(14) Uani d . 1 . .
O O1 0.1559(2) 0.29722(12) 0.13918(12) 0.0279(5) Uani d . 1 . .
O O2 0.2165(2) 0.27282(12) 0.02880(13) 0.0277(5) Uani d . 1 . .
N N1 0.4733(3) 0.30047(15) 0.17667(16) 0.0292(6) Uani d . 1 . .
H H1C 0.4229 0.3432 0.1871 0.035 Uiso calc R 1 . .
O O3 -0.0163(3) 0.18524(14) -0.05475(14) 0.0379(6) Uani d . 1 . .
N N3 0.1821(3) 0.12179(15) 0.09356(16) 0.0307(6) Uani d . 1 . .
H H3A 0.1206 0.1395 0.0495 0.037 Uiso calc R 1 . .
N N4 0.4586(3) 0.15922(15) 0.07460(16) 0.0291(6) Uani d . 1 . .
H H4D 0.5215 0.1309 0.1109 0.035 Uiso calc R 1 . .
C C17 0.1329(3) 0.30254(17) 0.06606(19) 0.0257(7) Uani d . 1 . .
C C18 0.0067(3) 0.34386(17) 0.02248(18) 0.0251(6) Uani d . 1 . .
N N2 0.3653(3) 0.17186(16) 0.24485(16) 0.0313(6) Uani d . 1 . .
H H2C 0.4281 0.1314 0.2465 0.038 Uiso calc R 1 . .
C C23 -0.0603(3) 0.32076(19) -0.05238(19) 0.0282(7) Uani d . 1 . .
O O4 -0.0144(3) 0.25603(16) -0.15998(15) 0.0474(7) Uani d . 1 . .
H H4 0.0042 0.2136 -0.1784 0.071 Uiso calc R 1 . .
C C11 0.5392(4) 0.2112(2) 0.0331(2) 0.0342(8) Uani d . 1 . .
H H11 0.4714 0.2448 -0.0025 0.041 Uiso calc R 1 . .
C C24 -0.0246(3) 0.2465(2) -0.08727(19) 0.0306(7) Uani d . 1 . .
C C3 0.2428(4) 0.1426(2) 0.2747(2) 0.0381(8) Uani d . 1 . .
H H3 0.1712 0.1845 0.2687 0.046 Uiso calc R 1 . .
C C1 0.5447(4) 0.2708(2) 0.2534(2) 0.0387(8) Uani d . 1 . .
H H1A 0.5936 0.3134 0.2854 0.046 Uiso calc R 1 . .
H H1B 0.6150 0.2317 0.2468 0.046 Uiso calc R 1 . .
C C2 0.4381(4) 0.2353(2) 0.2933(2) 0.0395(9) Uani d . 1 . .
H H2A 0.4850 0.2150 0.3447 0.047 Uiso calc R 1 . .
H H2B 0.3697 0.2748 0.3013 0.047 Uiso calc R 1 . .
C C22 -0.1695(4) 0.3647(2) -0.0938(2) 0.0392(8) Uani d . 1 . .
H H22 -0.2133 0.3500 -0.1451 0.047 Uiso calc R 1 . .
C C9 0.2719(4) 0.0646(2) 0.0655(2) 0.0399(8) Uani d . 1 . .
H H9A 0.2131 0.0271 0.0308 0.048 Uiso calc R 1 . .
H H9B 0.3274 0.0360 0.1101 0.048 Uiso calc R 1 . .
C C13 0.6348(4) 0.2627(2) 0.0907(2) 0.0358(8) Uani d . 1 . .
H H13A 0.7054 0.2845 0.0639 0.043 Uiso calc R 1 . .
H H13B 0.6854 0.2294 0.1330 0.043 Uiso calc R 1 . .
C C19 -0.0391(4) 0.40969(19) 0.0544(2) 0.0337(8) Uani d . 1 . .
H H19 0.0059 0.4259 0.1050 0.040 Uiso calc R 1 . .
C C14 0.5715(4) 0.3301(2) 0.1285(2) 0.0355(8) Uani d . 1 . .
C C4 0.2814(6) 0.1203(3) 0.3605(2) 0.0602(12) Uani d . 1 . .
H H4A 0.3532 0.0800 0.3679 0.090 Uiso calc R 1 . .
H H4B 0.1983 0.1009 0.3771 0.090 Uiso calc R 1 . .
H H4C 0.3174 0.1655 0.3916 0.090 Uiso calc R 1 . .
C C7 -0.0259(4) 0.1456(2) 0.1469(2) 0.0433(9) Uani d . 1 . .
H H7A 0.0142 0.1958 0.1648 0.065 Uiso calc R 1 . .
H H7B -0.0835 0.1270 0.1823 0.065 Uiso calc R 1 . .
H H7C -0.0837 0.1509 0.0946 0.065 Uiso calc R 1 . .
C C20 -0.1508(4) 0.4520(2) 0.0127(2) 0.0415(9) Uani d . 1 . .
H H20 -0.1829 0.4964 0.0353 0.050 Uiso calc R 1 . .
C C10 0.3674(4) 0.1046(2) 0.0226(2) 0.0363(8) Uani d . 1 . .
H H10A 0.4255 0.0662 0.0024 0.044 Uiso calc R 1 . .
H H10B 0.3117 0.1329 -0.0222 0.044 Uiso calc R 1 . .
C C15 0.4879(4) 0.3840(2) 0.0673(2) 0.0425(9) Uani d . 1 . .
H H15A 0.4044 0.3572 0.0392 0.064 Uiso calc R 1 . .
H H15B 0.5457 0.3994 0.0307 0.064 Uiso calc R 1 . .
H H15C 0.4601 0.4299 0.0928 0.064 Uiso calc R 1 . .
C C21 -0.2147(4) 0.4296(2) -0.0612(2) 0.0446(9) Uani d . 1 . .
H H21 -0.2901 0.4590 -0.0898 0.053 Uiso calc R 1 . .
C C5 0.1784(4) 0.0737(2) 0.2264(2) 0.0419(9) Uani d . 1 . .
H H5A 0.2552 0.0383 0.2213 0.050 Uiso calc R 1 . .
H H5B 0.1186 0.0460 0.2564 0.050 Uiso calc R 1 . .
C C6 0.0915(4) 0.0883(2) 0.1453(2) 0.0378(8) Uani d . 1 . .
C C16 0.6912(4) 0.3766(3) 0.1778(3) 0.0499(10) Uani d . 1 . .
H H16A 0.6527 0.4155 0.2078 0.075 Uiso calc R 1 . .
H H16B 0.7446 0.4020 0.1438 0.075 Uiso calc R 1 . .
H H16C 0.7527 0.3419 0.2134 0.075 Uiso calc R 1 . .
C C12 0.6241(4) 0.1662(3) -0.0161(2) 0.0482(10) Uani d . 1 . .
H H12A 0.6838 0.1286 0.0168 0.072 Uiso calc R 1 . .
H H12B 0.6823 0.2020 -0.0384 0.072 Uiso calc R 1 . .
H H12C 0.5603 0.1392 -0.0579 0.072 Uiso calc R 1 . .
C C8 0.0254(5) 0.0123(2) 0.1121(3) 0.0574(12) Uani d . 1 . .
H H8A -0.0166 0.0190 0.0569 0.086 Uiso calc R 1 . .
H H8B -0.0470 -0.0030 0.1400 0.086 Uiso calc R 1 . .
H H8C 0.0973 -0.0278 0.1181 0.086 Uiso calc R 1 . .
O O1W 0.0544(3) 0.14387(16) -0.23970(16) 0.0481(7) Uani d D 1 . .
H H2W 0.118(3) 0.111(2) -0.221(2) 0.058 Uiso d D 1 . .
H H1W 0.072(4) 0.161(2) -0.2823(14) 0.058 Uiso d D 1 . .
Cl Cl1 0.3438(6) -0.0040(3) -0.2176(3) 0.0381(10) Uani d PD 0.639(8) A 1
Cl Cl1' 0.3673(10) 0.0103(6) -0.2158(6) 0.0362(18) Uani d PD 0.361(8) A 2
O O5 0.4344(13) 0.0455(7) -0.2420(9) 0.203(6) Uani d PDU 0.639(8) A 1
O O6 0.3623(8) -0.0075(5) -0.1357(3) 0.110(3) Uani d PDU 0.639(8) A 1
O O7 0.3697(8) -0.0818(3) -0.2264(4) 0.073(2) Uani d PD 0.639(8) A 1
O O8 0.2001(5) 0.0061(3) -0.2550(3) 0.0588(18) Uani d PD 0.639(8) A 1
O O5' 0.2976(14) 0.0479(5) -0.2866(5) 0.088(5) Uani d PD 0.361(8) A 2
O O6' 0.4169(15) -0.0535(8) -0.2485(9) 0.101(5) Uani d PDU 0.361(8) A 2
O O7' 0.4898(15) 0.0527(8) -0.1817(8) 0.152(8) Uani d PD 0.361(8) A 2
O O8' 0.2850(14) 0.0248(7) -0.1601(7) 0.098(4) Uani d PDU 0.361(8) A 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 0.0000 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'
Cl Cl 0.1484 0.1585 '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'
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
N4 Ni1 N2 . . 105.40(11) ?
N4 Ni1 N1 . . 91.66(10) ?
N2 Ni1 N1 . . 84.67(11) ?
N4 Ni1 N3 . . 85.73(11) ?
N2 Ni1 N3 . . 91.06(11) ?
N1 Ni1 N3 . . 174.23(11) ?
N4 Ni1 O2 . . 92.84(10) ?
N2 Ni1 O2 . . 161.23(10) ?
N1 Ni1 O2 . . 99.45(10) ?
N3 Ni1 O2 . . 85.83(10) ?
N4 Ni1 O1 . . 153.72(10) ?
N2 Ni1 O1 . . 100.86(10) ?
N1 Ni1 O1 . . 89.79(10) ?
N3 Ni1 O1 . . 94.84(10) ?
O2 Ni1 O1 . . 61.07(8) ?
N4 Ni1 C17 . . 123.46(11) ?
N2 Ni1 C17 . . 130.81(11) ?
N1 Ni1 C17 . . 98.26(10) ?
N3 Ni1 C17 . . 87.46(10) ?
O2 Ni1 C17 . . 30.65(9) ?
O1 Ni1 C17 . . 30.68(9) ?
C17 O1 Ni1 . . 87.86(18) ?
C17 O2 Ni1 . . 89.74(19) ?
C1 N1 C14 . . 113.5(3) ?
C1 N1 Ni1 . . 104.9(2) ?
C14 N1 Ni1 . . 120.7(2) ?
C1 N1 H1C . . 105.5 ?
C14 N1 H1C . . 105.5 ?
Ni1 N1 H1C . . 105.5 ?
C9 N3 C6 . . 114.1(3) ?
C9 N3 Ni1 . . 103.5(2) ?
C6 N3 Ni1 . . 121.1(2) ?
C9 N3 H3A . . 105.7 ?
C6 N3 H3A . . 105.7 ?
Ni1 N3 H3A . . 105.7 ?
C10 N4 C11 . . 113.4(3) ?
C10 N4 Ni1 . . 103.3(2) ?
C11 N4 Ni1 . . 114.7(2) ?
C10 N4 H4D . . 108.4 ?
C11 N4 H4D . . 108.4 ?
Ni1 N4 H4D . . 108.4 ?
O2 C17 O1 . . 120.3(3) ?
O2 C17 C18 . . 119.1(3) ?
O1 C17 C18 . . 120.6(3) ?
O2 C17 Ni1 . . 59.61(16) ?
O1 C17 Ni1 . . 61.46(16) ?
C18 C17 Ni1 . . 171.0(2) ?
C19 C18 C23 . . 119.3(3) ?
C19 C18 C17 . . 119.3(3) ?
C23 C18 C17 . . 121.3(3) ?
C2 N2 C3 . . 112.0(3) ?
C2 N2 Ni1 . . 105.1(2) ?
C3 N2 Ni1 . . 115.8(2) ?
C2 N2 H2C . . 107.9 ?
C3 N2 H2C . . 107.9 ?
Ni1 N2 H2C . . 107.9 ?
C22 C23 C18 . . 119.6(3) ?
C22 C23 C24 . . 118.4(3) ?
C18 C23 C24 . . 121.8(3) ?
C24 O4 H4 . . 109.5 ?
N4 C11 C13 . . 110.2(3) ?
N4 C11 C12 . . 112.0(3) ?
C13 C11 C12 . . 110.2(3) ?
N4 C11 H11 . . 108.1 ?
C13 C11 H11 . . 108.1 ?
C12 C11 H11 . . 108.1 ?
O3 C24 O4 . . 124.3(3) ?
O3 C24 C23 . . 124.2(3) ?
O4 C24 C23 . . 111.3(3) ?
N2 C3 C5 . . 109.8(3) ?
N2 C3 C4 . . 112.5(3) ?
C5 C3 C4 . . 109.8(3) ?
N2 C3 H3 . . 108.2 ?
C5 C3 H3 . . 108.2 ?
C4 C3 H3 . . 108.2 ?
N1 C1 C2 . . 109.1(3) ?
N1 C1 H1A . . 109.9 ?
C2 C1 H1A . . 109.9 ?
N1 C1 H1B . . 109.9 ?
C2 C1 H1B . . 109.9 ?
H1A C1 H1B . . 108.3 ?
N2 C2 C1 . . 109.4(3) ?
N2 C2 H2A . . 109.8 ?
C1 C2 H2A . . 109.8 ?
N2 C2 H2B . . 109.8 ?
C1 C2 H2B . . 109.8 ?
H2A C2 H2B . . 108.2 ?
C21 C22 C23 . . 120.5(3) ?
C21 C22 H22 . . 119.7 ?
C23 C22 H22 . . 119.7 ?
N3 C9 C10 . . 109.7(3) ?
N3 C9 H9A . . 109.7 ?
C10 C9 H9A . . 109.7 ?
N3 C9 H9B . . 109.7 ?
C10 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
C11 C13 C14 . . 119.2(3) ?
C11 C13 H13A . . 107.5 ?
C14 C13 H13A . . 107.5 ?
C11 C13 H13B . . 107.5 ?
C14 C13 H13B . . 107.5 ?
H13A C13 H13B . . 107.0 ?
C18 C19 C20 . . 120.3(3) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
N1 C14 C15 . . 107.2(3) ?
N1 C14 C16 . . 111.4(3) ?
C15 C14 C16 . . 108.1(3) ?
N1 C14 C13 . . 110.4(3) ?
C15 C14 C13 . . 111.4(3) ?
C16 C14 C13 . . 108.4(3) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C21 C20 C19 . . 120.1(3) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
N4 C10 C9 . . 110.2(3) ?
N4 C10 H10A . . 109.6 ?
C9 C10 H10A . . 109.6 ?
N4 C10 H10B . . 109.6 ?
C9 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.1 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C20 C21 C22 . . 120.2(3) ?
C20 C21 H21 . . 119.9 ?
C22 C21 H21 . . 119.9 ?
C6 C5 C3 . . 118.4(3) ?
C6 C5 H5A . . 107.7 ?
C3 C5 H5A . . 107.7 ?
C6 C5 H5B . . 107.7 ?
C3 C5 H5B . . 107.7 ?
H5A C5 H5B . . 107.1 ?
N3 C6 C5 . . 110.2(3) ?
N3 C6 C7 . . 107.5(3) ?
C5 C6 C7 . . 111.5(3) ?
N3 C6 C8 . . 110.7(3) ?
C5 C6 C8 . . 108.9(3) ?
C7 C6 C8 . . 108.0(3) ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C6 C8 H8A . . 109.5 ?
C6 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C6 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
H2W O1W H1W . . 108.1(17) ?
O5 Cl1 O7 . . 115.5(8) ?
O5 Cl1 O6 . . 113.2(8) ?
O7 Cl1 O6 . . 94.8(6) ?
O5 Cl1 O8 . . 114.8(7) ?
O7 Cl1 O8 . . 104.5(5) ?
O6 Cl1 O8 . . 112.1(6) ?
O6' Cl1' O8' . . 137.0(11) ?
O6' Cl1' O7' . . 104.5(10) ?
O8' Cl1' O7' . . 99.6(9) ?
O6' Cl1' O5' . . 98.4(9) ?
O8' Cl1' O5' . . 106.4(9) ?
O7' Cl1' O5' . . 109.5(9) ?
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
Ni1 N4 . 2.087(3) ?
Ni1 N2 . 2.088(3) ?
Ni1 N1 . 2.131(3) ?
Ni1 N3 . 2.133(3) ?
Ni1 O2 . 2.135(2) ?
Ni1 O1 . 2.176(2) ?
Ni1 C17 . 2.475(3) ?
O1 C17 . 1.264(4) ?
O2 C17 . 1.262(4) ?
N1 C1 . 1.478(4) ?
N1 C14 . 1.501(4) ?
N1 H1C . 0.9300 ?
O3 C24 . 1.202(4) ?
N3 C9 . 1.479(4) ?
N3 C6 . 1.516(4) ?
N3 H3A . 0.9300 ?
N4 C10 . 1.480(4) ?
N4 C11 . 1.488(4) ?
N4 H4D . 0.9300 ?
C17 C18 . 1.495(4) ?
C18 C19 . 1.389(4) ?
C18 C23 . 1.403(4) ?
N2 C2 . 1.481(4) ?
N2 C3 . 1.496(4) ?
N2 H2C . 0.9300 ?
C23 C22 . 1.389(5) ?
C23 C24 . 1.501(5) ?
O4 C24 . 1.316(4) ?
O4 H4 . 0.8400 ?
C11 C13 . 1.520(5) ?
C11 C12 . 1.534(5) ?
C11 H11 . 1.0000 ?
C3 C5 . 1.527(5) ?
C3 C4 . 1.530(5) ?
C3 H3 . 1.0000 ?
C1 C2 . 1.508(5) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C22 C21 . 1.379(5) ?
C22 H22 . 0.9500 ?
C9 C10 . 1.492(5) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C13 C14 . 1.539(5) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C19 C20 . 1.393(5) ?
C19 H19 . 0.9500 ?
C14 C15 . 1.529(5) ?
C14 C16 . 1.533(5) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C7 C6 . 1.524(5) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C20 C21 . 1.378(6) ?
C20 H20 . 0.9500 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C21 H21 . 0.9500 ?
C5 C6 . 1.523(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C8 . 1.531(5) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
O1W H2W . 0.855(11) ?
O1W H1W . 0.860(11) ?
Cl1 O5 . 1.367(7) ?
Cl1 O7 . 1.390(7) ?
Cl1 O6 . 1.418(7) ?
Cl1 O8 . 1.434(6) ?
Cl1' O6' . 1.383(9) ?
Cl1' O8' . 1.416(9) ?
Cl1' O7' . 1.428(9) ?
Cl1' O5' . 1.446(9) ?
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
N1 H1C O5 4_566 0.93 2.29 3.094(9) 144.4
N2 H2C O6' 3_655 0.93 2.03 2.952(10) 172.7
O4 H4 O1W . 0.84 1.76 2.572(4) 162.1
O1W H2W O8 . 0.855(11) 2.13(3) 2.827(5) 138(4)
O1W H1W O1 4_565 0.860(11) 1.892(16) 2.734(3) 166(4)
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
N4 Ni1 O1 C17 . . . . 13.4(3) ?
N2 Ni1 O1 C17 . . . . -168.73(18) ?
N1 Ni1 O1 C17 . . . . 106.74(19) ?
N3 Ni1 O1 C17 . . . . -76.71(19) ?
O2 Ni1 O1 C17 . . . . 5.81(17) ?
N4 Ni1 O2 C17 . . . . 177.56(18) ?
N2 Ni1 O2 C17 . . . . 11.1(4) ?
N1 Ni1 O2 C17 . . . . -90.29(19) ?
N3 Ni1 O2 C17 . . . . 92.06(19) ?
O1 Ni1 O2 C17 . . . . -5.81(17) ?
N4 Ni1 N1 C1 . . . . -92.5(2) ?
N2 Ni1 N1 C1 . . . . 12.8(2) ?
N3 Ni1 N1 C1 . . . . -29.6(12) ?
O2 Ni1 N1 C1 . . . . 174.4(2) ?
O1 Ni1 N1 C1 . . . . 113.8(2) ?
C17 Ni1 N1 C1 . . . . 143.4(2) ?
N4 Ni1 N1 C14 . . . . 37.3(2) ?
N2 Ni1 N1 C14 . . . . 142.6(2) ?
N3 Ni1 N1 C14 . . . . 100.2(11) ?
O2 Ni1 N1 C14 . . . . -55.9(2) ?
O1 Ni1 N1 C14 . . . . -116.5(2) ?
C17 Ni1 N1 C14 . . . . -86.9(2) ?
N4 Ni1 N3 C9 . . . . 12.3(2) ?
N2 Ni1 N3 C9 . . . . -93.1(2) ?
N1 Ni1 N3 C9 . . . . -50.9(11) ?
O2 Ni1 N3 C9 . . . . 105.5(2) ?
O1 Ni1 N3 C9 . . . . 165.9(2) ?
C17 Ni1 N3 C9 . . . . 136.1(2) ?
N4 Ni1 N3 C6 . . . . 141.7(3) ?
N2 Ni1 N3 C6 . . . . 36.3(3) ?
N1 Ni1 N3 C6 . . . . 78.5(11) ?
O2 Ni1 N3 C6 . . . . -125.2(2) ?
O1 Ni1 N3 C6 . . . . -64.7(2) ?
C17 Ni1 N3 C6 . . . . -94.5(3) ?
N2 Ni1 N4 C10 . . . . 107.1(2) ?
N1 Ni1 N4 C10 . . . . -167.9(2) ?
N3 Ni1 N4 C10 . . . . 17.2(2) ?
O2 Ni1 N4 C10 . . . . -68.4(2) ?
O1 Ni1 N4 C10 . . . . -75.1(3) ?
C17 Ni1 N4 C10 . . . . -66.9(2) ?
N2 Ni1 N4 C11 . . . . -128.9(2) ?
N1 Ni1 N4 C11 . . . . -44.0(2) ?
N3 Ni1 N4 C11 . . . . 141.1(2) ?
O2 Ni1 N4 C11 . . . . 55.5(2) ?
O1 Ni1 N4 C11 . . . . 48.9(3) ?
C17 Ni1 N4 C11 . . . . 57.0(2) ?
Ni1 O2 C17 O1 . . . . 10.2(3) ?
Ni1 O2 C17 C18 . . . . -169.7(2) ?
Ni1 O1 C17 O2 . . . . -10.0(3) ?
Ni1 O1 C17 C18 . . . . 169.9(3) ?
N4 Ni1 C17 O2 . . . . -2.9(2) ?
N2 Ni1 C17 O2 . . . . -175.31(17) ?
N1 Ni1 C17 O2 . . . . 94.60(18) ?
N3 Ni1 C17 O2 . . . . -86.11(18) ?
O1 Ni1 C17 O2 . . . . 170.0(3) ?
N4 Ni1 C17 O1 . . . . -172.92(16) ?
N2 Ni1 C17 O1 . . . . 14.7(2) ?
N1 Ni1 C17 O1 . . . . -75.39(18) ?
N3 Ni1 C17 O1 . . . . 103.90(18) ?
O2 Ni1 C17 O1 . . . . -170.0(3) ?
N4 Ni1 C17 C18 . . . . 81.2(15) ?
N2 Ni1 C17 C18 . . . . -91.2(14) ?
N1 Ni1 C17 C18 . . . . 18E1(10) ?
N3 Ni1 C17 C18 . . . . -2.0(14) ?
O2 Ni1 C17 C18 . . . . 84.1(14) ?
O1 Ni1 C17 C18 . . . . -105.9(15) ?
O2 C17 C18 C19 . . . . -143.1(3) ?
O1 C17 C18 C19 . . . . 37.1(4) ?
Ni1 C17 C18 C19 . . . . 138.0(13) ?
O2 C17 C18 C23 . . . . 32.3(4) ?
O1 C17 C18 C23 . . . . -147.6(3) ?
Ni1 C17 C18 C23 . . . . -46.7(16) ?
N4 Ni1 N2 C2 . . . . 107.1(2) ?
N1 Ni1 N2 C2 . . . . 16.9(2) ?
N3 Ni1 N2 C2 . . . . -167.0(2) ?
O2 Ni1 N2 C2 . . . . -86.9(4) ?
O1 Ni1 N2 C2 . . . . -71.9(2) ?
C17 Ni1 N2 C2 . . . . -79.5(3) ?
N4 Ni1 N2 C3 . . . . -128.8(2) ?
N1 Ni1 N2 C3 . . . . 141.0(2) ?
N3 Ni1 N2 C3 . . . . -42.9(2) ?
O2 Ni1 N2 C3 . . . . 37.2(4) ?
O1 Ni1 N2 C3 . . . . 52.2(2) ?
C17 Ni1 N2 C3 . . . . 44.6(3) ?
C19 C18 C23 C22 . . . . 1.2(5) ?
C17 C18 C23 C22 . . . . -174.2(3) ?
C19 C18 C23 C24 . . . . -174.3(3) ?
C17 C18 C23 C24 . . . . 10.3(5) ?
C10 N4 C11 C13 . . . . -177.4(3) ?
Ni1 N4 C11 C13 . . . . 64.2(3) ?
C10 N4 C11 C12 . . . . -54.3(4) ?
Ni1 N4 C11 C12 . . . . -172.7(2) ?
C22 C23 C24 O3 . . . . -126.8(4) ?
C18 C23 C24 O3 . . . . 48.7(5) ?
C22 C23 C24 O4 . . . . 48.2(4) ?
C18 C23 C24 O4 . . . . -136.3(3) ?
C2 N2 C3 C5 . . . . -175.8(3) ?
Ni1 N2 C3 C5 . . . . 63.8(3) ?
C2 N2 C3 C4 . . . . -53.1(4) ?
Ni1 N2 C3 C4 . . . . -173.6(3) ?
C14 N1 C1 C2 . . . . -174.3(3) ?
Ni1 N1 C1 C2 . . . . -40.4(3) ?
C3 N2 C2 C1 . . . . -170.7(3) ?
Ni1 N2 C2 C1 . . . . -44.2(3) ?
N1 C1 C2 N2 . . . . 59.3(4) ?
C18 C23 C22 C21 . . . . -1.7(5) ?
C24 C23 C22 C21 . . . . 174.0(3) ?
C6 N3 C9 C10 . . . . -173.9(3) ?
Ni1 N3 C9 C10 . . . . -40.4(3) ?
N4 C11 C13 C14 . . . . -74.1(4) ?
C12 C11 C13 C14 . . . . 161.7(3) ?
C23 C18 C19 C20 . . . . 0.3(5) ?
C17 C18 C19 C20 . . . . 175.7(3) ?
C1 N1 C14 C15 . . . . -159.6(3) ?
Ni1 N1 C14 C15 . . . . 74.6(3) ?
C1 N1 C14 C16 . . . . -41.5(4) ?
Ni1 N1 C14 C16 . . . . -167.3(2) ?
C1 N1 C14 C13 . . . . 79.0(3) ?
Ni1 N1 C14 C13 . . . . -46.9(3) ?
C11 C13 C14 N1 . . . . 62.9(4) ?
C11 C13 C14 C15 . . . . -56.1(4) ?
C11 C13 C14 C16 . . . . -174.9(3) ?
C18 C19 C20 C21 . . . . -1.3(6) ?
C11 N4 C10 C9 . . . . -169.9(3) ?
Ni1 N4 C10 C9 . . . . -45.1(3) ?
N3 C9 C10 N4 . . . . 61.0(4) ?
C19 C20 C21 C22 . . . . 0.7(6) ?
C23 C22 C21 C20 . . . . 0.8(6) ?
N2 C3 C5 C6 . . . . -74.9(4) ?
C4 C3 C5 C6 . . . . 160.9(4) ?
C9 N3 C6 C5 . . . . 76.9(4) ?
Ni1 N3 C6 C5 . . . . -47.7(4) ?
C9 N3 C6 C7 . . . . -161.4(3) ?
Ni1 N3 C6 C7 . . . . 74.1(3) ?
C9 N3 C6 C8 . . . . -43.6(4) ?
Ni1 N3 C6 C8 . . . . -168.2(3) ?
C3 C5 C6 N3 . . . . 64.5(4) ?
C3 C5 C6 C7 . . . . -54.8(4) ?
C3 C5 C6 C8 . . . . -173.9(3) ?
