# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2003



data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Jason Halfen'
'Young Junior,Victor, G.'

_publ_contact_author_name        'Dr Jason Halfen'
_publ_contact_author_address     
;
Department of Chemistry
University of Wisconsin-Eau Claire
105 Garfield Avenue
Eau Claire
WI
54702
UNITED STATES OF AMERICA
;

_publ_contact_author_email       HALFENJA@UWEC.EDU

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Efficient Preparation of 1,4,8-Trimethylcyclam and
its Conversion into a Thioalkyl-Pendant, Pentadentate Chelate
;

data_03202aa
_database_code_CSD               220192

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            03202aa
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H33 N4 S Ni, Cl O4'
_chemical_formula_sum            'C15 H33 Cl N4 Ni O4 S'
_chemical_formula_weight         459.67

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3748(15)
_cell_length_b                   14.505(3)
_cell_length_c                   8.9820(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.659(3)
_cell_angle_gamma                90.00
_cell_volume                     999.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1891
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Pyramid
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    1.237
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_T_max  0.7900
_exptl_absorpt_process_details   'TWINABS (Shedrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11765
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.58
_reflns_number_total             4729
_reflns_number_gt                4075
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.104(12)
_refine_ls_number_reflns         4729
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Ni1 Ni 0.34781(4) 0.24180(2) 0.13057(4) 0.01526(9) Uani 1 1 d . . .
N1 N 0.1545(3) 0.28066(18) -0.0979(3) 0.0204(6) Uani 1 1 d . . .
C1 C -0.0236(4) 0.2927(3) -0.1005(4) 0.0289(8) Uani 1 1 d . . .
H1A H -0.1042 0.3090 -0.2126 0.035 Uiso 1 1 calc R . .
H1B H -0.0207 0.3456 -0.0298 0.035 Uiso 1 1 calc R . .
C2 C -0.0981(4) 0.2104(2) -0.0466(4) 0.0310(9) Uani 1 1 d . . .
H2A H -0.0919 0.1559 -0.1103 0.037 Uiso 1 1 calc R . .
H2B H -0.2226 0.2223 -0.0716 0.037 Uiso 1 1 calc R . .
C3 C -0.0056(4) 0.1881(3) 0.1328(4) 0.0275(8) Uani 1 1 d . . .
H3A H -0.0008 0.2449 0.1958 0.033 Uiso 1 1 calc R . .
H3B H -0.0763 0.1424 0.1616 0.033 Uiso 1 1 calc R . .
N2 N 0.1754(3) 0.15119(18) 0.1848(3) 0.0205(6) Uani 1 1 d . . .
C4 C 0.2525(4) 0.1458(2) 0.3645(4) 0.0240(7) Uani 1 1 d . . .
H4A H 0.2023 0.0928 0.4002 0.029 Uiso 1 1 calc R . .
H4B H 0.2252 0.2027 0.4105 0.029 Uiso 1 1 calc R . .
C5 C 0.4491(4) 0.1344(2) 0.4253(4) 0.0238(7) Uani 1 1 d . . .
H5A H 0.5009 0.1299 0.5454 0.029 Uiso 1 1 calc R . .
H5B H 0.4761 0.0768 0.3810 0.029 Uiso 1 1 calc R . .
N3 N 0.5258(3) 0.21447(17) 0.3736(3) 0.0191(6) Uani 1 1 d . . .
C6 C 0.5409(4) 0.2927(2) 0.4841(4) 0.0249(7) Uani 1 1 d . . .
H6A H 0.6183 0.2741 0.5960 0.030 Uiso 1 1 calc R . .
H6B H 0.4243 0.3053 0.4832 0.030 Uiso 1 1 calc R . .
C7 C 0.6111(4) 0.3815(2) 0.4436(4) 0.0290(8) Uani 1 1 d . . .
H7A H 0.6435 0.4238 0.5376 0.035 Uiso 1 1 calc R . .
H7B H 0.7185 0.3672 0.4272 0.035 Uiso 1 1 calc R . .
C8 C 0.4856(4) 0.4303(2) 0.2950(4) 0.0286(8) Uani 1 1 d . . .
H8A H 0.3758 0.4410 0.3091 0.034 Uiso 1 1 calc R . .
H8B H 0.5351 0.4913 0.2883 0.034 Uiso 1 1 calc R . .
N4 N 0.4426(3) 0.38131(18) 0.1370(3) 0.0208(6) Uani 1 1 d . . .
C9 C 0.2924(4) 0.4297(2) 0.0126(4) 0.0257(7) Uani 1 1 d . . .
H9A H 0.3321 0.4890 -0.0156 0.031 Uiso 1 1 calc R . .
H9B H 0.2044 0.4434 0.0572 0.031 Uiso 1 1 calc R . .
C10 C 0.2113(4) 0.3716(2) -0.1376(4) 0.0270(8) Uani 1 1 d . . .
H10A H 0.1095 0.4043 -0.2181 0.032 Uiso 1 1 calc R . .
H10B H 0.2968 0.3617 -0.1866 0.032 Uiso 1 1 calc R . .
C11 C 0.1484(4) 0.2121(2) -0.2234(4) 0.0266(8) Uani 1 1 d . . .
H11A H 0.0818 0.2385 -0.3326 0.032 Uiso 1 1 calc R . .
H11B H 0.0860 0.1563 -0.2122 0.032 Uiso 1 1 calc R . .
C12 C 0.3286(5) 0.1848(3) -0.2096(4) 0.0330(9) Uani 1 1 d . . .
H12A H 0.3787 0.2364 -0.2491 0.040 Uiso 1 1 calc R . .
H12B H 0.3181 0.1310 -0.2807 0.040 Uiso 1 1 calc R . .
S1 S 0.47651(10) 0.15616(6) -0.00333(10) 0.02494(18) Uani 1 1 d . . .
C13 C 0.1679(5) 0.0575(2) 0.1163(4) 0.0305(8) Uani 1 1 d . . .
H13A H 0.0998 0.0170 0.1561 0.046 Uiso 1 1 calc R . .
H13B H 0.2863 0.0330 0.1503 0.046 Uiso 1 1 calc R . .
H13C H 0.1124 0.0605 -0.0026 0.046 Uiso 1 1 calc R . .
C14 C 0.7033(4) 0.1866(3) 0.3906(4) 0.0297(8) Uani 1 1 d . . .
H14A H 0.7733 0.1694 0.5038 0.044 Uiso 1 1 calc R . .
H14B H 0.7591 0.2382 0.3597 0.044 Uiso 1 1 calc R . .
H14C H 0.6944 0.1338 0.3196 0.044 Uiso 1 1 calc R . .
C15 C 0.5957(4) 0.3870(2) 0.0935(4) 0.0278(8) Uani 1 1 d . . .
H15A H 0.6217 0.4518 0.0820 0.042 Uiso 1 1 calc R . .
H15B H 0.5697 0.3547 -0.0094 0.042 Uiso 1 1 calc R . .
H15C H 0.6967 0.3582 0.1793 0.042 Uiso 1 1 calc R . .
Cl1 Cl 0.08490(10) 0.44897(6) 0.42691(10) 0.02687(18) Uani 1 1 d . . .
O1 O 0.0634(4) 0.4788(3) 0.2683(4) 0.0744(12) Uani 1 1 d . . .
O2 O 0.0306(3) 0.35503(19) 0.4217(3) 0.0518(8) Uani 1 1 d . . .
O3 O 0.2638(3) 0.45613(19) 0.5364(3) 0.0395(6) Uani 1 1 d . . .
O4 O -0.0199(4) 0.5045(2) 0.4823(4) 0.0505(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.01624(17) 0.01426(17) 0.01644(17) -0.00003(18) 0.00778(13) -0.00046(18)
N1 0.0223(13) 0.0210(14) 0.0180(14) 0.0004(10) 0.0083(11) -0.0005(11)
C1 0.0201(17) 0.033(2) 0.0270(18) 0.0015(16) 0.0023(15) 0.0036(15)
C2 0.0174(17) 0.041(2) 0.032(2) -0.0044(15) 0.0079(15) 0.0005(14)
C3 0.0209(17) 0.036(2) 0.0299(19) -0.0054(15) 0.0145(15) -0.0049(14)
N2 0.0221(13) 0.0198(14) 0.0225(13) -0.0010(11) 0.0121(11) -0.0017(11)
C4 0.0291(17) 0.0237(18) 0.0235(17) 0.0040(14) 0.0151(14) -0.0030(14)
C5 0.0306(18) 0.0181(17) 0.0216(16) 0.0058(13) 0.0093(14) 0.0016(14)
N3 0.0179(13) 0.0196(15) 0.0194(14) 0.0005(10) 0.0069(11) 0.0000(10)
C6 0.0250(17) 0.0257(19) 0.0224(17) -0.0024(14) 0.0081(15) -0.0025(15)
C7 0.0309(19) 0.027(2) 0.0282(18) -0.0097(15) 0.0110(15) -0.0088(15)
C8 0.0325(19) 0.0229(19) 0.0335(19) -0.0070(14) 0.0166(16) -0.0057(15)
N4 0.0207(14) 0.0169(14) 0.0259(14) 0.0009(11) 0.0106(11) -0.0014(11)
C9 0.0313(18) 0.0174(17) 0.0322(18) 0.0070(14) 0.0167(15) 0.0047(14)
C10 0.0299(18) 0.025(2) 0.0238(17) 0.0070(14) 0.0085(14) 0.0039(15)
C11 0.0325(19) 0.030(2) 0.0132(16) -0.0022(13) 0.0049(14) -0.0013(14)
C12 0.043(2) 0.032(2) 0.033(2) -0.0041(15) 0.0240(18) -0.0003(17)
S1 0.0264(4) 0.0232(4) 0.0298(4) -0.0033(4) 0.0160(4) 0.0025(3)
C13 0.041(2) 0.0214(19) 0.032(2) -0.0060(14) 0.0170(16) -0.0083(15)
C14 0.0238(18) 0.029(2) 0.035(2) 0.0052(15) 0.0099(16) 0.0056(14)
C15 0.0305(19) 0.0213(18) 0.0358(19) 0.0025(14) 0.0178(16) -0.0051(14)
Cl1 0.0276(4) 0.0277(4) 0.0291(4) 0.0039(3) 0.0153(4) 0.0048(3)
O1 0.057(2) 0.127(3) 0.0479(19) 0.0488(19) 0.0307(16) 0.0346(19)
O2 0.0458(17) 0.0276(15) 0.072(2) -0.0136(14) 0.0132(15) -0.0060(13)
O3 0.0282(13) 0.0441(17) 0.0447(15) -0.0045(13) 0.0131(12) -0.0057(12)
O4 0.0468(18) 0.0427(18) 0.076(2) -0.0076(15) 0.0394(16) 0.0084(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Ni1 N1 2.117(2) . ?
Ni1 N3 2.129(3) . ?
Ni1 N2 2.148(3) . ?
Ni1 N4 2.166(3) . ?
Ni1 S1 2.2785(9) . ?
N1 C11 1.489(4) . ?
N1 C1 1.492(4) . ?
N1 C10 1.494(4) . ?
C1 C2 1.513(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.517(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N2 1.495(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N2 C4 1.480(4) . ?
N2 C13 1.483(4) . ?
C4 C5 1.522(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.488(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N3 C6 1.479(4) . ?
N3 C14 1.488(4) . ?
C6 C7 1.519(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.504(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N4 1.495(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N4 C9 1.482(4) . ?
N4 C15 1.485(4) . ?
C9 C10 1.502(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.517(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 S1 1.816(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
Cl1 O4 1.420(3) . ?
Cl1 O1 1.429(3) . ?
Cl1 O3 1.429(2) . ?
Cl1 O2 1.431(3) . ?

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
N1 Ni1 N3 172.59(10) . . ?
N1 Ni1 N2 93.46(9) . . ?
N3 Ni1 N2 84.91(9) . . ?
N1 Ni1 N4 84.66(10) . . ?
N3 Ni1 N4 92.76(9) . . ?
N2 Ni1 N4 146.94(10) . . ?
N1 Ni1 S1 88.48(7) . . ?
N3 Ni1 S1 98.91(7) . . ?
N2 Ni1 S1 106.83(7) . . ?
N4 Ni1 S1 106.11(7) . . ?
C11 N1 C1 109.6(2) . . ?
C11 N1 C10 109.0(2) . . ?
C1 N1 C10 107.8(2) . . ?
C11 N1 Ni1 109.67(19) . . ?
C1 N1 Ni1 114.67(18) . . ?
C10 N1 Ni1 105.89(18) . . ?
N1 C1 C2 116.1(3) . . ?
N1 C1 H1A 108.3 . . ?
C2 C1 H1A 108.3 . . ?
N1 C1 H1B 108.3 . . ?
C2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 C3 114.1(3) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N2 C3 C2 115.5(3) . . ?
N2 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
N2 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C4 N2 C13 109.3(3) . . ?
C4 N2 C3 107.6(2) . . ?
C13 N2 C3 109.3(2) . . ?
C4 N2 Ni1 103.93(18) . . ?
C13 N2 Ni1 112.82(19) . . ?
C3 N2 Ni1 113.6(2) . . ?
N2 C4 C5 109.4(2) . . ?
N2 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N3 C5 C4 110.1(2) . . ?
N3 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N3 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C6 N3 C5 108.7(2) . . ?
C6 N3 C14 109.0(2) . . ?
C5 N3 C14 107.1(2) . . ?
C6 N3 Ni1 112.43(19) . . ?
C5 N3 Ni1 104.65(18) . . ?
C14 N3 Ni1 114.5(2) . . ?
N3 C6 C7 115.2(3) . . ?
N3 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
N3 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 114.3(3) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N4 C8 C7 115.8(3) . . ?
N4 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
N4 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C9 N4 C15 109.6(2) . . ?
C9 N4 C8 107.4(2) . . ?
C15 N4 C8 108.6(2) . . ?
C9 N4 Ni1 103.38(18) . . ?
C15 N4 Ni1 113.01(19) . . ?
C8 N4 Ni1 114.53(19) . . ?
N4 C9 C10 110.7(3) . . ?
N4 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C9 110.7(3) . . ?
N1 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N1 C11 C12 112.4(3) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 S1 113.1(2) . . ?
C11 C12 H12A 109.0 . . ?
S1 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
S1 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 S1 Ni1 98.06(12) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 Cl1 O1 109.20(19) . . ?
O4 Cl1 O3 110.03(18) . . ?
O1 Cl1 O3 110.00(17) . . ?
O4 Cl1 O2 108.60(18) . . ?
O1 Cl1 O2 110.1(2) . . ?
O3 Cl1 O2 108.88(16) . . ?

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
N3 Ni1 N1 C11 -162.2(7) . . . . ?
N2 Ni1 N1 C11 -85.2(2) . . . . ?
N4 Ni1 N1 C11 127.9(2) . . . . ?
S1 Ni1 N1 C11 21.59(19) . . . . ?
N3 Ni1 N1 C1 -38.4(9) . . . . ?
N2 Ni1 N1 C1 38.6(2) . . . . ?
N4 Ni1 N1 C1 -108.2(2) . . . . ?
S1 Ni1 N1 C1 145.4(2) . . . . ?
N3 Ni1 N1 C10 80.3(8) . . . . ?
N2 Ni1 N1 C10 157.33(19) . . . . ?
N4 Ni1 N1 C10 10.44(19) . . . . ?
S1 Ni1 N1 C10 -95.90(19) . . . . ?
C11 N1 C1 C2 67.4(3) . . . . ?
C10 N1 C1 C2 -174.1(3) . . . . ?
Ni1 N1 C1 C2 -56.5(3) . . . . ?
N1 C1 C2 C3 68.4(4) . . . . ?
C1 C2 C3 N2 -69.5(4) . . . . ?
C2 C3 N2 C4 172.4(3) . . . . ?
C2 C3 N2 C13 -69.0(4) . . . . ?
C2 C3 N2 Ni1 57.9(3) . . . . ?
N1 Ni1 N2 C4 -156.03(19) . . . . ?
N3 Ni1 N2 C4 16.72(19) . . . . ?
N4 Ni1 N2 C4 -70.5(3) . . . . ?
S1 Ni1 N2 C4 114.51(18) . . . . ?
N1 Ni1 N2 C13 85.6(2) . . . . ?
N3 Ni1 N2 C13 -101.6(2) . . . . ?
N4 Ni1 N2 C13 171.2(2) . . . . ?
S1 Ni1 N2 C13 -3.8(2) . . . . ?
N1 Ni1 N2 C3 -39.4(2) . . . . ?
N3 Ni1 N2 C3 133.4(2) . . . . ?
N4 Ni1 N2 C3 46.2(3) . . . . ?
S1 Ni1 N2 C3 -128.82(19) . . . . ?
C13 N2 C4 C5 77.0(3) . . . . ?
C3 N2 C4 C5 -164.5(3) . . . . ?
Ni1 N2 C4 C5 -43.7(3) . . . . ?
N2 C4 C5 N3 60.1(3) . . . . ?
C4 C5 N3 C6 79.4(3) . . . . ?
C4 C5 N3 C14 -162.9(3) . . . . ?
C4 C5 N3 Ni1 -40.9(3) . . . . ?
N1 Ni1 N3 C6 -27.3(9) . . . . ?
N2 Ni1 N3 C6 -104.8(2) . . . . ?
N4 Ni1 N3 C6 42.1(2) . . . . ?
S1 Ni1 N3 C6 148.90(18) . . . . ?
N1 Ni1 N3 C5 90.6(8) . . . . ?
N2 Ni1 N3 C5 12.99(19) . . . . ?
N4 Ni1 N3 C5 159.93(19) . . . . ?
S1 Ni1 N3 C5 -93.29(18) . . . . ?
N1 Ni1 N3 C14 -152.5(7) . . . . ?
N2 Ni1 N3 C14 130.0(2) . . . . ?
N4 Ni1 N3 C14 -83.1(2) . . . . ?
S1 Ni1 N3 C14 23.7(2) . . . . ?
C5 N3 C6 C7 -177.8(3) . . . . ?
C14 N3 C6 C7 65.8(3) . . . . ?
Ni1 N3 C6 C7 -62.4(3) . . . . ?
N3 C6 C7 C8 72.2(4) . . . . ?
C6 C7 C8 N4 -66.8(4) . . . . ?
C7 C8 N4 C9 168.4(3) . . . . ?
C7 C8 N4 C15 -73.1(3) . . . . ?
C7 C8 N4 Ni1 54.3(3) . . . . ?
N1 Ni1 N4 C9 17.63(18) . . . . ?
N3 Ni1 N4 C9 -155.40(18) . . . . ?
N2 Ni1 N4 C9 -70.5(3) . . . . ?
S1 Ni1 N4 C9 104.50(17) . . . . ?
N1 Ni1 N4 C15 -100.8(2) . . . . ?
N3 Ni1 N4 C15 86.2(2) . . . . ?
N2 Ni1 N4 C15 171.05(18) . . . . ?
S1 Ni1 N4 C15 -13.9(2) . . . . ?
N1 Ni1 N4 C8 134.1(2) . . . . ?
N3 Ni1 N4 C8 -38.9(2) . . . . ?
N2 Ni1 N4 C8 46.0(3) . . . . ?
S1 Ni1 N4 C8 -138.99(19) . . . . ?
C15 N4 C9 C10 77.1(3) . . . . ?
C8 N4 C9 C10 -165.1(3) . . . . ?
Ni1 N4 C9 C10 -43.7(3) . . . . ?
C11 N1 C10 C9 -155.6(3) . . . . ?
C1 N1 C10 C9 85.5(3) . . . . ?
Ni1 N1 C10 C9 -37.7(3) . . . . ?
N4 C9 C10 N1 57.7(3) . . . . ?
C1 N1 C11 C12 -170.7(3) . . . . ?
C10 N1 C11 C12 71.5(3) . . . . ?
Ni1 N1 C11 C12 -44.0(3) . . . . ?
N1 C11 C12 S1 47.8(4) . . . . ?
C11 C12 S1 Ni1 -25.8(3) . . . . ?
N1 Ni1 S1 C12 2.03(14) . . . . ?
N3 Ni1 S1 C12 -177.48(15) . . . . ?
N2 Ni1 S1 C12 95.18(14) . . . . ?
N4 Ni1 S1 C12 -81.97(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.070