 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H29 N5 Ni O3 S2'
_chemical_formula_weight          558.35
 
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'
 'Ni'  'Ni'   0.3393   1.1124
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
_symmetry_space_group_name_hall   'P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    11.6146(2)
_cell_length_b                    13.3420(4)
_cell_length_c                    16.3699(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2536.71(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     17051
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.60
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.462
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1168
_exptl_absorpt_coefficient_mu     0.966
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.5950
_exptl_absorpt_correction_T_max   0.9443
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             22904
_diffrn_reflns_av_R_equivalents   0.0803
_diffrn_reflns_av_sigmaI/netI     0.0498
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          27.49
_reflns_number_total              5787
_reflns_number_gt                 5450
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ?
_computing_publication_material   SHELXL-97
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0283P)²+1.9155P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_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    -0.006(10)
_refine_ls_number_reflns          5787
_refine_ls_number_parameters      322
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0367
_refine_ls_R_factor_gt            0.0334
_refine_ls_wR_factor_ref          0.0781
_refine_ls_wR_factor_gt           0.0757
_refine_ls_goodness_of_fit_ref    0.993
_refine_ls_restrained_S_all       0.993
_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
C22 C 0.2996(3) 0.6070(2) 0.9679(2) 0.0364(7) Uani 1 1 d . . .
H22 H 0.2669 0.5455 0.9857 0.044 Uiso 1 1 calc R . .
C23 C 0.2745(2) 0.7822(2) 0.9382(2) 0.0323(6) Uani 1 1 d . . .
H23A H 0.3585 0.7834 0.9435 0.049 Uiso 1 1 calc R . .
H23B H 0.2410 0.8349 0.9725 0.049 Uiso 1 1 calc R . .
H23C H 0.2533 0.7939 0.8810 0.049 Uiso 1 1 calc R . .
C24 C 0.1087(3) 0.6806(3) 0.9848(3) 0.0747(16) Uani 1 1 d . . .
H24A H 0.0923 0.6163 1.0112 0.112 Uiso 1 1 calc R . .
H24B H 0.0627 0.6867 0.9349 0.112 Uiso 1 1 calc R . .
H24C H 0.0893 0.7355 1.0222 0.112 Uiso 1 1 calc R . .
N5 N 0.2314(2) 0.68579(19) 0.96405(16) 0.0339(6) Uani 1 1 d . . .
O3 O 0.40271(17) 0.60727(15) 0.95025(13) 0.0359(5) Uani 1 1 d . . .
C1 C 0.3403(2) 0.30669(18) 0.99502(15) 0.0165(5) Uani 1 1 d . . .
H1 H 0.4154 0.2861 1.0108 0.020 Uiso 1 1 calc R . .
C2 C 0.3239(2) 0.32792(18) 0.90900(15) 0.0167(5) Uani 1 1 d . . .
C3 C 0.4220(2) 0.32415(18) 0.85851(15) 0.0181(5) Uani 1 1 d . . .
H3 H 0.4959 0.3202 0.8831 0.022 Uiso 1 1 calc R . .
C4 C 0.4141(2) 0.32601(17) 0.77403(15) 0.0171(5) Uani 1 1 d . . .
C5 C 0.5186(2) 0.3201(2) 0.71961(15) 0.0211(5) Uani 1 1 d . . .
H5A H 0.5877 0.3354 0.7516 0.032 Uiso 1 1 calc R . .
H5B H 0.5110 0.3687 0.6750 0.032 Uiso 1 1 calc R . .
H5C H 0.5250 0.2524 0.6969 0.032 Uiso 1 1 calc R . .
C6 C 0.3035(2) 0.32658(18) 0.73968(15) 0.0183(5) Uani 1 1 d . . .
H6 H 0.2959 0.3242 0.6819 0.022 Uiso 1 1 calc R . .
C7 C 0.2050(2) 0.33045(17) 0.78728(14) 0.0159(5) Uani 1 1 d . . .
C8 C 0.2136(2) 0.33478(18) 0.87358(14) 0.0164(5) Uani 1 1 d . . .
C9 C 0.0907(2) 0.32821(18) 0.74903(15) 0.0180(5) Uani 1 1 d . . .
H9 H 0.0304 0.2915 0.7744 0.022 Uiso 1 1 calc R . .
C10 C 0.2959(2) 0.26164(19) 1.12976(15) 0.0192(5) Uani 1 1 d . . .
H10A H 0.3615 0.2159 1.1198 0.023 Uiso 1 1 calc R . .
H10B H 0.2299 0.2207 1.1486 0.023 Uiso 1 1 calc R . .
C11 C 0.3282(2) 0.3359(2) 1.19601(16) 0.0226(5) Uani 1 1 d . . .
H11A H 0.4106 0.3534 1.1903 0.027 Uiso 1 1 calc R . .
H11B H 0.3177 0.3038 1.2500 0.027 Uiso 1 1 calc R . .
C12 C 0.2567(2) 0.4313(2) 1.19273(16) 0.0213(5) Uani 1 1 d . . .
H12A H 0.2583 0.4641 1.2470 0.026 Uiso 1 1 calc R . .
H12B H 0.2914 0.4780 1.1527 0.026 Uiso 1 1 calc R . .
C13 C 0.0601(2) 0.42832(18) 1.22515(15) 0.0171(5) Uani 1 1 d . . .
H13 H 0.0899 0.4439 1.2777 0.021 Uiso 1 1 calc R . .
C14 C -0.0641(2) 0.42678(18) 1.21842(15) 0.0171(5) Uani 1 1 d . . .
C15 C -0.1270(2) 0.43242(18) 1.29187(14) 0.0200(5) Uani 1 1 d . . .
H15 H -0.0865 0.4321 1.3423 0.024 Uiso 1 1 calc R . .
C16 C -0.2457(2) 0.4384(2) 1.29284(15) 0.0226(5) Uani 1 1 d . . .
C17 C -0.3124(3) 0.4423(3) 1.37141(17) 0.0359(7) Uani 1 1 d . . .
H17A H -0.3430 0.3756 1.3839 0.054 Uiso 1 1 calc R . .
H17B H -0.3762 0.4899 1.3658 0.054 Uiso 1 1 calc R . .
H17C H -0.2615 0.4641 1.4158 0.054 Uiso 1 1 calc R . .
C18 C -0.3032(2) 0.43824(19) 1.21802(15) 0.0202(5) Uani 1 1 d . . .
H18 H -0.3849 0.4417 1.2175 0.024 Uiso 1 1 calc R . .
C19 C -0.2442(2) 0.43314(18) 1.14432(15) 0.0177(5) Uani 1 1 d . . .
C20 C -0.1223(2) 0.42909(17) 1.14337(14) 0.0154(4) Uani 1 1 d . . .
C21 C -0.30816(19) 0.42858(17) 1.06645(14) 0.0175(5) Uani 1 1 d . . .
H21 H -0.2830 0.3850 1.0242 0.021 Uiso 1 1 calc R . .
N1 N 0.26484(16) 0.31247(14) 1.05275(13) 0.0157(4) Uani 1 1 d . . .
N2 N 0.13529(17) 0.41130(14) 1.16932(12) 0.0170(4) Uani 1 1 d . . .
N3 N 0.07091(18) 0.37432(17) 0.68280(12) 0.0206(4) Uani 1 1 d . . .
N4 N -0.39721(16) 0.48311(15) 1.05584(13) 0.0182(4) Uani 1 1 d . . .
O1 O -0.04242(15) 0.35620(14) 0.65647(11) 0.0232(4) Uani 1 1 d . . .
H1A H -0.0638 0.4029 0.6256 0.035 Uiso 1 1 calc R . .
O2 O -0.44921(16) 0.46193(14) 0.98045(11) 0.0234(4) Uani 1 1 d . . .
H2 H -0.5042 0.5017 0.9727 0.035 Uiso 1 1 calc R . .
S1 S 0.08608(5) 0.34817(5) 0.92842(4) 0.01930(13) Uani 1 1 d . . .
S2 S -0.05405(5) 0.43847(4) 1.04894(4) 0.01747(12) Uani 1 1 d . . .
Ni1 Ni 0.11734(2) 0.37532(2) 1.056096(18) 0.01442(8) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C22 O3 1.232(4) . ?
C22 N5 1.318(4) . ?
C22 H22 0.9500 . ?
C23 N5 1.444(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 N5 1.466(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C1 N1 1.291(3) . ?
C1 C2 1.449(3) . ?
C1 H1 0.9500 . ?
C2 C8 1.409(3) . ?
C2 C3 1.409(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C6 1.402(3) . ?
C4 C5 1.508(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.417(3) . ?
C7 C9 1.469(3) . ?
C8 S1 1.741(2) . ?
C9 N3 1.268(3) . ?
C9 H9 0.9500 . ?
C10 N1 1.476(3) . ?
C10 C11 1.516(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N2 1.486(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.284(3) . ?
C13 C14 1.446(3) . ?
C13 H13 0.9500 . ?
C14 C20 1.403(3) . ?
C14 C15 1.409(3) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 C18 1.396(4) . ?
C16 C17 1.503(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.416(3) . ?
C19 C21 1.477(3) . ?
C20 S2 1.742(2) . ?
C21 N4 1.276(3) . ?
C21 H21 0.9500 . ?
N1 Ni1 1.9082(19) . ?
N2 Ni1 1.926(2) . ?
N3 O1 1.406(3) . ?
N4 O2 1.403(3) . ?
O1 H1A 0.8400 . ?
O2 H2 0.8400 . ?
S1 Ni1 2.1520(6) . ?
S2 Ni1 2.1647(6) . ?
 
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
O3 C22 N5 124.8(3) . . ?
O3 C22 H22 117.6 . . ?
N5 C22 H22 117.6 . . ?
N5 C23 H23A 109.5 . . ?
N5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N5 C24 H24A 109.5 . . ?
N5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 N5 C23 121.1(2) . . ?
C22 N5 C24 122.4(3) . . ?
C23 N5 C24 116.5(3) . . ?
N1 C1 C2 127.6(2) . . ?
N1 C1 H1 116.2 . . ?
C2 C1 H1 116.2 . . ?
C8 C2 C3 119.8(2) . . ?
C8 C2 C1 122.1(2) . . ?
C3 C2 C1 117.2(2) . . ?
C4 C3 C2 122.1(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C6 117.5(2) . . ?
C3 C4 C5 122.3(2) . . ?
C6 C4 C5 120.1(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 122.1(2) . . ?
C7 C6 H6 119.0 . . ?
C4 C6 H6 119.0 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 C9 120.4(2) . . ?
C8 C7 C9 119.3(2) . . ?
C2 C8 C7 118.1(2) . . ?
C2 C8 S1 124.59(18) . . ?
C7 C8 S1 117.31(18) . . ?
N3 C9 C7 121.2(2) . . ?
N3 C9 H9 119.4 . . ?
C7 C9 H9 119.4 . . ?
N1 C10 C11 111.8(2) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C12 112.7(2) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N2 C12 C11 112.2(2) . . ?
N2 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N2 C13 C14 128.4(2) . . ?
N2 C13 H13 115.8 . . ?
C14 C13 H13 115.8 . . ?
C20 C14 C15 119.7(2) . . ?
C20 C14 C13 123.2(2) . . ?
C15 C14 C13 116.8(2) . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C18 117.9(2) . . ?
C15 C16 C17 121.8(2) . . ?
C18 C16 C17 120.3(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C16 121.7(2) . . ?
C19 C18 H18 119.1 . . ?
C16 C18 H18 119.1 . . ?
C18 C19 C20 120.3(2) . . ?
C18 C19 C21 120.2(2) . . ?
C20 C19 C21 119.5(2) . . ?
C14 C20 C19 118.2(2) . . ?
C14 C20 S2 123.98(19) . . ?
C19 C20 S2 117.52(18) . . ?
N4 C21 C19 120.1(2) . . ?
N4 C21 H21 119.9 . . ?
C19 C21 H21 119.9 . . ?
C1 N1 C10 115.6(2) . . ?
C1 N1 Ni1 131.03(17) . . ?
C10 N1 Ni1 113.36(15) . . ?
C13 N2 C12 115.5(2) . . ?
C13 N2 Ni1 130.94(17) . . ?
C12 N2 Ni1 113.31(16) . . ?
C9 N3 O1 110.4(2) . . ?
C21 N4 O2 110.72(19) . . ?
N3 O1 H1A 109.5 . . ?
N4 O2 H2 109.5 . . ?
C8 S1 Ni1 112.01(8) . . ?
C20 S2 Ni1 110.05(8) . . ?
N1 Ni1 N2 92.29(9) . . ?
N1 Ni1 S1 92.84(6) . . ?
N2 Ni1 S1 174.19(6) . . ?
N1 Ni1 S2 174.31(6) . . ?
N2 Ni1 S2 93.13(6) . . ?
S1 Ni1 S2 81.83(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.327
_refine_diff_density_min   -0.298
_refine_diff_density_rms    0.062
