# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_l1
_database_code_depnum_ccdc_archive 'CCDC 1418962'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;
_audit_creation_date             2015-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H28 N6 S2'
_chemical_formula_sum            'C22 H28 N6 S2'
_chemical_formula_weight         440.62
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.831(6)
_cell_length_b                   10.956(8)
_cell_length_c                   14.357(11)
_cell_angle_alpha                75.594(18)
_cell_angle_beta                 89.60(3)
_cell_angle_gamma                72.16(2)
_cell_volume                     1132.5(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12690
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.128
_diffrn_reflns_theta_min         3.187
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4225
_reflns_number_total             4299
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.8495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1011
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N5(H5), N6(H6), C4(H4), C5(H5A), C6(H6A), C7(H7), C8(H8), C11(H11),
 C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.57463(5) 0.20289(4) 0.18256(3) 0.01933(12) Uani 1 1 d . . . . .
S2 S 0.20253(6) 0.31742(4) 0.53960(3) 0.02315(12) Uani 1 1 d . . . . .
N1 N 0.75571(18) 0.22926(13) 0.32742(10) 0.0169(3) Uani 1 1 d . . . . .
N2 N 0.58463(18) 0.42578(13) 0.23508(9) 0.0153(3) Uani 1 1 d . . . . .
N3 N 0.35257(18) 0.48572(13) 0.11273(9) 0.0148(3) Uani 1 1 d . . . . .
H3 H 0.3908 0.4079 0.1028 0.018 Uiso 1 1 calc R . . . .
N4 N 0.11899(18) 0.50465(13) 0.26774(9) 0.0157(3) Uani 1 1 d . . . . .
N5 N 0.12747(19) 0.48318(14) 0.36643(9) 0.0177(3) Uani 1 1 d . . . . .
H5 H 0.0837 0.5470 0.3932 0.021 Uiso 1 1 calc R . . . .
N6 N 0.28999(18) 0.26980(14) 0.37141(10) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.2864 0.2958 0.3096 0.022 Uiso 1 1 calc R . . . .
C1 C 0.6374(2) 0.29133(16) 0.25058(11) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.4565(2) 0.51259(16) 0.17284(11) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.4357(2) 0.65310(16) 0.16977(11) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.3925(2) 0.75177(17) 0.08386(12) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.3698 0.7317 0.0269 0.024 Uiso 1 1 calc R . . . .
C5 C 0.3831(3) 0.88041(18) 0.08305(14) 0.0270(4) Uani 1 1 d . . . . .
H5A H 0.3527 0.9469 0.0256 0.032 Uiso 1 1 calc R . . . .
C6 C 0.4189(3) 0.90990(18) 0.16737(15) 0.0294(4) Uani 1 1 d . . . . .
H6A H 0.4131 0.9962 0.1666 0.035 Uiso 1 1 calc R . . . .
C7 C 0.4633(2) 0.81181(18) 0.25288(14) 0.0265(4) Uani 1 1 d . . . . .
H7 H 0.4867 0.8322 0.3096 0.032 Uiso 1 1 calc R . . . .
C8 C 0.4729(2) 0.68370(17) 0.25424(12) 0.0205(3) Uani 1 1 d . . . . .
H8 H 0.5044 0.6175 0.3118 0.025 Uiso 1 1 calc R . . . .
C9 C 0.1861(2) 0.57081(15) 0.06327(11) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.0472(2) 0.63890(16) 0.11039(11) 0.0161(3) Uani 1 1 d . . . . .
C11 C -0.1099(2) 0.72291(17) 0.05598(13) 0.0209(3) Uani 1 1 d . . . . .
H11 H -0.2021 0.7720 0.0857 0.025 Uiso 1 1 calc R . . . .
C12 C -0.1310(2) 0.73450(17) -0.04141(13) 0.0245(4) Uani 1 1 d . . . . .
H12 H -0.2374 0.7906 -0.0767 0.029 Uiso 1 1 calc R . . . .
C13 C 0.0052(3) 0.66312(18) -0.08664(12) 0.0231(4) Uani 1 1 d . . . . .
H13 H -0.0099 0.6695 -0.1521 0.028 Uiso 1 1 calc R . . . .
C14 C 0.1638(2) 0.58229(17) -0.03431(12) 0.0190(3) Uani 1 1 d . . . . .
H14 H 0.2565 0.5351 -0.0649 0.023 Uiso 1 1 calc R . . . .
C15 C 0.0571(2) 0.62353(16) 0.21573(11) 0.0155(3) Uani 1 1 d . . . . .
C16 C -0.0064(3) 0.74616(17) 0.25078(13) 0.0238(4) Uani 1 1 d . . . . .
H16A H -0.1336 0.7681 0.2573 0.036 Uiso 1 1 calc GR . . . .
H16B H 0.0184 0.8181 0.2053 0.036 Uiso 1 1 calc GR . . . .
H16C H 0.0551 0.7310 0.3122 0.036 Uiso 1 1 calc GR . . . .
C17 C 0.2077(2) 0.35713(16) 0.41944(11) 0.0167(3) Uani 1 1 d . . . . .
C18 C 0.3852(2) 0.13320(17) 0.41816(13) 0.0231(4) Uani 1 1 d . . . . .
H18A H 0.4305 0.0863 0.3703 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.3049 0.0934 0.4556 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.4837 0.1287 0.4597 0.035 Uiso 1 1 calc GR . . . .
C19 C 0.8412(2) 0.08593(17) 0.35513(13) 0.0223(4) Uani 1 1 d . . . . .
H19A H 0.7599 0.0432 0.3367 0.027 Uiso 1 1 calc R . . . .
H19B H 0.8653 0.0557 0.4246 0.027 Uiso 1 1 calc R . . . .
C20 C 1.0154(3) 0.04619(19) 0.30755(16) 0.0301(4) Uani 1 1 d . . . . .
H20A H 0.9899 0.0652 0.2392 0.045 Uiso 1 1 calc GR . . . .
H20B H 1.0755 -0.0471 0.3330 0.045 Uiso 1 1 calc GR . . . .
H20C H 1.0912 0.0953 0.3203 0.045 Uiso 1 1 calc GR . . . .
C21 C 0.8147(2) 0.30277(17) 0.38657(12) 0.0200(3) Uani 1 1 d . . . . .
H21A H 0.8201 0.3862 0.3454 0.024 Uiso 1 1 calc R . . . .
H21B H 0.9350 0.2518 0.4157 0.024 Uiso 1 1 calc R . . . .
C22 C 0.6910(3) 0.3308(2) 0.46509(13) 0.0291(4) Uani 1 1 d . . . . .
H22A H 0.5715 0.3807 0.4367 0.044 Uiso 1 1 calc GR . . . .
H22B H 0.7330 0.3811 0.5005 0.044 Uiso 1 1 calc GR . . . .
H22C H 0.6898 0.2485 0.5080 0.044 Uiso 1 1 calc GR . . . .


_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
S1 C1 1.7042(18) . ?
S2 C17 1.674(2) . ?
N1 C1 1.339(2) . ?
N1 C19 1.456(2) . ?
N1 C21 1.469(2) . ?
N2 C1 1.362(2) . ?
N2 C2 1.309(2) . ?
N3 H3 0.8600 . ?
N3 C2 1.333(2) . ?
N3 C9 1.419(2) . ?
N4 N5 1.376(2) . ?
N4 C15 1.274(2) . ?
N5 H5 0.8600 . ?
N5 C17 1.354(2) . ?
N6 H6 0.8600 . ?
N6 C17 1.323(2) . ?
N6 C18 1.439(2) . ?
C2 C3 1.487(2) . ?
C3 C4 1.387(2) . ?
C3 C8 1.391(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(3) . ?
C5 H5A 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6A 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(2) . ?
C9 C14 1.382(2) . ?
C10 C11 1.390(2) . ?
C10 C15 1.479(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.493(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.513(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.509(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C1 N1 C19 122.62(14) . . ?
C1 N1 C21 121.78(14) . . ?
C19 N1 C21 115.52(14) . . ?
C2 N2 C1 126.69(14) . . ?
C2 N3 H3 116.3 . . ?
C2 N3 C9 127.39(14) . . ?
C9 N3 H3 116.3 . . ?
C15 N4 N5 118.54(14) . . ?
N4 N5 H5 121.5 . . ?
C17 N5 N4 117.03(13) . . ?
C17 N5 H5 121.5 . . ?
C17 N6 H6 118.6 . . ?
C17 N6 C18 122.83(15) . . ?
C18 N6 H6 118.6 . . ?
N1 C1 S1 120.47(13) . . ?
N1 C1 N2 112.20(14) . . ?
N2 C1 S1 127.29(13) . . ?
N2 C2 N3 126.30(15) . . ?
N2 C2 C3 114.10(14) . . ?
N3 C2 C3 119.56(14) . . ?
C4 C3 C2 121.51(15) . . ?
C4 C3 C8 119.58(16) . . ?
C8 C3 C2 118.76(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.89(17) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 C4 120.05(17) . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 H6A 119.9 . . ?
C5 C6 C7 120.25(18) . . ?
C7 C6 H6A 119.9 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.03(17) . . ?
C8 C7 H7 120.0 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.19(16) . . ?
C7 C8 H8 119.9 . . ?
C10 C9 N3 122.06(15) . . ?
C14 C9 N3 117.50(14) . . ?
C14 C9 C10 120.42(15) . . ?
C9 C10 C15 123.18(15) . . ?
C11 C10 C9 118.31(16) . . ?
C11 C10 C15 118.49(15) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.96(17) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.16(16) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.61(16) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.47(16) . . ?
C13 C14 H14 119.8 . . ?
N4 C15 C10 115.61(14) . . ?
N4 C15 C16 126.50(16) . . ?
C10 C15 C16 117.89(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 S2 120.60(13) . . ?
N6 C17 S2 122.84(13) . . ?
N6 C17 N5 116.55(15) . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.3 . . ?
N1 C19 H19B 109.3 . . ?
N1 C19 C20 111.40(15) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.1 . . ?
N1 C21 H21B 109.1 . . ?
N1 C21 C22 112.56(15) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
N3 H3 S1 0.86 2.28 2.968(2) 137.2 .
N5 H5 S2 0.86 2.61 3.351(2) 145.2 2_566
N6 H6 N4 0.86 2.19 2.577(2) 106.9 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nil1
_database_code_depnum_ccdc_archive 'CCDC 1418963'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;
_audit_creation_date             2015-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H26 N6 Ni S2'
_chemical_formula_sum            'C22 H26 N6 Ni S2'
_chemical_formula_weight         497.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni1 S2 N6 C22 H20'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2007(7)
_cell_length_b                   17.5298(9)
_cell_length_c                   20.1722(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4668.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6237
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.2340
_cell_measurement_theta_min      4.1050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.032
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16086
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         3.445
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   47.00   1.0000   34.8800
omega____ theta____ kappa____ phi______ frames
    -       10.0590  -99.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega   32.00   77.00   1.0000   34.8800
omega____ theta____ kappa____ phi______ frames
    -       10.0590   57.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -54.00   14.00   1.0000   34.8800
omega____ theta____ kappa____ phi______ frames
    -       10.0590  -77.0000 -120.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0471558000
_diffrn_orient_matrix_UB_12      -0.0059411000
_diffrn_orient_matrix_UB_13      -0.0160728000
_diffrn_orient_matrix_UB_21      0.0197314000
_diffrn_orient_matrix_UB_22      -0.0331607000
_diffrn_orient_matrix_UB_23      -0.0154622000
_diffrn_orient_matrix_UB_31      -0.0167039000
_diffrn_orient_matrix_UB_32      -0.0224136000
_diffrn_orient_matrix_UB_33      0.0271442000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3247
_reflns_number_total             4122
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.2310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1180
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.22786(3) 0.10653(2) 0.47195(2) 0.03439(15) Uani 1 1 d . . . . .
S1 S 0.08285(6) 0.11086(5) 0.52030(4) 0.0443(2) Uani 1 1 d . . . . .
S2 S 0.28739(6) 0.15247(5) 0.56320(4) 0.0490(2) Uani 1 1 d . . . . .
N1 N -0.10448(19) 0.11731(12) 0.47488(11) 0.0383(6) Uani 1 1 d . . . . .
N2 N 0.01424(18) 0.14631(12) 0.39750(11) 0.0385(6) Uani 1 1 d . . . . .
N3 N 0.17571(18) 0.08718(12) 0.38733(11) 0.0373(5) Uani 1 1 d . . . . .
N4 N 0.36402(18) 0.08903(12) 0.44542(13) 0.0417(6) Uani 1 1 d . . . . .
N5 N 0.44355(19) 0.11797(14) 0.48395(15) 0.0494(7) Uani 1 1 d . . . . .
N6 N 0.4842(2) 0.17478(15) 0.58185(16) 0.0604(8) Uani 1 1 d . . . . .
H6 H 0.4657 0.1916 0.6200 0.072 Uiso 1 1 calc R . . . .
C1 C -0.0069(2) 0.12363(15) 0.45967(14) 0.0351(6) Uani 1 1 d . . . . .
C2 C -0.1387(2) 0.10152(17) 0.54219(15) 0.0450(7) Uani 1 1 d . . . . .
H2A H -0.0910 0.0675 0.5636 0.054 Uiso 1 1 calc R . . . .
H2B H -0.2039 0.0760 0.5405 0.054 Uiso 1 1 calc R . . . .
C3 C -0.1483(3) 0.1737(2) 0.58235(17) 0.0616(9) Uani 1 1 d . . . . .
H3A H -0.1924 0.2087 0.5599 0.092 Uiso 1 1 calc GR . . . .
H3B H -0.0827 0.1965 0.5876 0.092 Uiso 1 1 calc GR . . . .
H3C H -0.1759 0.1619 0.6252 0.092 Uiso 1 1 calc GR . . . .
C4 C -0.1841(2) 0.13024(17) 0.42495(16) 0.0457(7) Uani 1 1 d . . . . .
H4A H -0.1634 0.1713 0.3958 0.055 Uiso 1 1 calc R . . . .
H4B H -0.2459 0.1460 0.4472 0.055 Uiso 1 1 calc R . . . .
C5 C -0.2053(3) 0.0608(2) 0.3845(2) 0.0707(11) Uani 1 1 d . . . . .
H5A H -0.2559 0.0724 0.3518 0.106 Uiso 1 1 calc GR . . . .
H5B H -0.2295 0.0208 0.4129 0.106 Uiso 1 1 calc GR . . . .
H5C H -0.1443 0.0446 0.3629 0.106 Uiso 1 1 calc GR . . . .
C6 C 0.0964(2) 0.12868(14) 0.36483(14) 0.0362(6) Uani 1 1 d . . . . .
C7 C 0.1010(2) 0.16416(14) 0.29752(14) 0.0410(7) Uani 1 1 d . . . . .
C8 C 0.0127(3) 0.1768(2) 0.26197(17) 0.0612(9) Uani 1 1 d . . . . .
H8 H -0.0491 0.1603 0.2790 0.073 Uiso 1 1 calc R . . . .
C9 C 0.0157(3) 0.2135(2) 0.20167(18) 0.0745(11) Uani 1 1 d . . . . .
H9 H -0.0437 0.2209 0.1777 0.089 Uiso 1 1 calc R . . . .
C10 C 0.1062(3) 0.23925(19) 0.17694(18) 0.0685(11) Uani 1 1 d . . . . .
H10 H 0.1079 0.2645 0.1364 0.082 Uiso 1 1 calc R . . . .
C11 C 0.1930(3) 0.22805(17) 0.21135(17) 0.0574(9) Uani 1 1 d . . . . .
H11 H 0.2541 0.2458 0.1943 0.069 Uiso 1 1 calc R . . . .
C12 C 0.1917(3) 0.19041(15) 0.27167(16) 0.0481(8) Uani 1 1 d . . . . .
H12 H 0.2518 0.1827 0.2948 0.058 Uiso 1 1 calc R . . . .
C13 C 0.2216(2) 0.03547(15) 0.34310(14) 0.0417(7) Uani 1 1 d . . . . .
C14 C 0.3243(3) 0.01653(15) 0.34680(15) 0.0478(8) Uani 1 1 d . . . . .
C15 C 0.3612(3) -0.03778(18) 0.30106(18) 0.0663(10) Uani 1 1 d . . . . .
H15 H 0.4293 -0.0512 0.3023 0.080 Uiso 1 1 calc R . . . .
C16 C 0.2991(4) -0.0712(2) 0.2549(2) 0.0782(13) Uani 1 1 d . . . . .
H16 H 0.3257 -0.1061 0.2249 0.094 Uiso 1 1 calc R . . . .
C17 C 0.1986(3) -0.05356(18) 0.25279(18) 0.0672(11) Uani 1 1 d . . . . .
H17 H 0.1567 -0.0767 0.2216 0.081 Uiso 1 1 calc R . . . .
C18 C 0.1591(3) -0.00146(16) 0.29683(15) 0.0533(8) Uani 1 1 d . . . . .
H18 H 0.0902 0.0094 0.2959 0.064 Uiso 1 1 calc R . . . .
C19 C 0.3961(2) 0.05011(16) 0.39357(16) 0.0470(8) Uani 1 1 d . . . . .
C20 C 0.5075(3) 0.0388(2) 0.38332(19) 0.0718(11) Uani 1 1 d . . . . .
H20A H 0.5436 0.0824 0.3999 0.108 Uiso 1 1 calc GR . . . .
H20B H 0.5212 0.0329 0.3369 0.108 Uiso 1 1 calc GR . . . .
H20C H 0.5292 -0.0061 0.4066 0.108 Uiso 1 1 calc GR . . . .
C21 C 0.4130(2) 0.14747(15) 0.53927(17) 0.0440(7) Uani 1 1 d . . . . .
C22 C 0.5898(3) 0.1761(2) 0.5643(2) 0.0738(11) Uani 1 1 d . . . . .
H22A H 0.5995 0.2087 0.5266 0.111 Uiso 1 1 calc GR . . . .
H22B H 0.6117 0.1253 0.5535 0.111 Uiso 1 1 calc GR . . . .
H22C H 0.6287 0.1950 0.6010 0.111 Uiso 1 1 calc GR . . . .


_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 S1 2.1498(9) . ?
Ni1 S2 2.1576(9) . ?
Ni1 N3 1.871(2) . ?
Ni1 N4 1.900(2) . ?
S1 C1 1.717(3) . ?
S2 C21 1.729(3) . ?
N1 C1 1.329(4) . ?
N1 C2 1.458(4) . ?
N1 C4 1.474(4) . ?
N2 C1 1.345(4) . ?
N2 C6 1.306(4) . ?
N3 C6 1.354(4) . ?
N3 C13 1.409(3) . ?
N4 N5 1.401(4) . ?
N4 C19 1.319(4) . ?
N5 C21 1.294(4) . ?
N6 H6 0.8600 . ?
N6 C21 1.360(4) . ?
N6 C22 1.438(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.508(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.491(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.495(4) . ?
C7 C8 1.387(4) . ?
C7 C12 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.355(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(4) . ?
C13 C18 1.403(4) . ?
C14 C15 1.413(4) . ?
C14 C19 1.462(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.363(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.498(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
S1 Ni1 S2 85.64(3) . . ?
N3 Ni1 S1 95.32(8) . . ?
N3 Ni1 S2 168.47(7) . . ?
N3 Ni1 N4 93.55(11) . . ?
N4 Ni1 S1 167.34(8) . . ?
N4 Ni1 S2 87.48(8) . . ?
C1 S1 Ni1 107.19(10) . . ?
C21 S2 Ni1 95.29(11) . . ?
C1 N1 C2 122.1(2) . . ?
C1 N1 C4 121.4(2) . . ?
C2 N1 C4 116.4(2) . . ?
C6 N2 C1 124.9(2) . . ?
C6 N3 Ni1 119.55(18) . . ?
C6 N3 C13 117.8(2) . . ?
C13 N3 Ni1 122.43(19) . . ?
N5 N4 Ni1 119.61(19) . . ?
C19 N4 Ni1 127.7(2) . . ?
C19 N4 N5 112.7(3) . . ?
C21 N5 N4 112.9(3) . . ?
C21 N6 H6 119.4 . . ?
C21 N6 C22 121.3(3) . . ?
C22 N6 H6 119.4 . . ?
N1 C1 S1 119.6(2) . . ?
N1 C1 N2 116.2(2) . . ?
N2 C1 S1 124.0(2) . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
N1 C2 C3 111.5(3) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
N1 C4 C5 112.5(2) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 N3 126.9(3) . . ?
N2 C6 C7 113.2(2) . . ?
N3 C6 C7 119.8(3) . . ?
C8 C7 C6 120.1(3) . . ?
C12 C7 C6 121.1(3) . . ?
C12 C7 C8 118.6(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C14 C13 N3 122.4(3) . . ?
C14 C13 C18 119.7(3) . . ?
C18 C13 N3 117.8(3) . . ?
C13 C14 C15 117.4(3) . . ?
C13 C14 C19 124.6(2) . . ?
C15 C14 C19 117.9(3) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.6 . . ?
N4 C19 C14 120.8(3) . . ?
N4 C19 C20 119.6(3) . . ?
C14 C19 C20 119.7(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 S2 124.0(2) . . ?
N5 C21 N6 118.0(3) . . ?
N6 C21 S2 117.9(3) . . ?
N6 C22 H22A 109.5 . . ?
N6 C22 H22B 109.5 . . ?
N6 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C2 H2A S1 0.97 2.57 2.963(3) 104.3 .
C20 H20A N5 0.96 2.24 2.600(5) 101.2 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cul1
_database_code_depnum_ccdc_archive 'CCDC 1418964'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;
_audit_creation_date             2015-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H26 Cu N6 S2'
_chemical_formula_sum            'C22 H26 Cu N6 S2'
_chemical_formula_weight         502.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu1 S2 N6 C23 H27'
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'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3637(4)
_cell_length_b                   17.6802(7)
_cell_length_c                   19.9696(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4718.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4768
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.6960
_cell_measurement_theta_min      4.2850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13366
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         3.608
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   84.00   1.0000   19.7600
omega____ theta____ kappa____ phi______ frames
    -       10.3715   38.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00   -1.00   1.0000   19.7600
omega____ theta____ kappa____ phi______ frames
    -      -11.3090  -19.0000  -60.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0468983000
_diffrn_orient_matrix_UB_12      -0.0132987000
_diffrn_orient_matrix_UB_13      0.0117668000
_diffrn_orient_matrix_UB_21      0.0175987000
_diffrn_orient_matrix_UB_22      0.0377716000
_diffrn_orient_matrix_UB_23      0.0020682000
_diffrn_orient_matrix_UB_31      -0.0175415000
_diffrn_orient_matrix_UB_32      0.0023416000
_diffrn_orient_matrix_UB_33      0.0334566000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3346
_reflns_number_total             4158
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+1.8410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0968
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C4(H4), C5(H5), C6(H6A), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
  C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.72278(2) 0.10527(2) 0.52520(2) 0.03504(12) Uani 1 1 d . . . . .
S1 S 0.57251(5) 0.10462(5) 0.47497(3) 0.0460(2) Uani 1 1 d . . . . .
S2 S 0.78845(5) 0.16026(5) 0.43482(4) 0.0517(2) Uani 1 1 d . . . . .
N1 N 0.39069(16) 0.11522(12) 0.52513(10) 0.0373(5) Uani 1 1 d . . . . .
N2 N 0.51115(15) 0.14229(12) 0.60131(10) 0.0384(5) Uani 1 1 d . . . . .
N3 N 0.67068(16) 0.08402(12) 0.61344(10) 0.0384(5) Uani 1 1 d . . . . .
N4 N 0.86219(16) 0.08583(12) 0.55418(11) 0.0423(5) Uani 1 1 d . . . . .
N5 N 0.94008(17) 0.11527(14) 0.51595(12) 0.0505(6) Uani 1 1 d . . . . .
N6 N 0.98264(17) 0.17952(15) 0.42189(14) 0.0644(7) Uani 1 1 d . . . . .
H6 H 0.9656 0.1989 0.3841 0.077 Uiso 1 1 calc R . . . .
C1 C 0.48793(19) 0.11939(14) 0.53855(12) 0.0346(6) Uani 1 1 d . . . . .
C2 C 0.59200(19) 0.12551(14) 0.63512(11) 0.0366(6) Uani 1 1 d . . . . .
C3 C 0.5965(2) 0.16214(15) 0.70256(12) 0.0421(6) Uani 1 1 d . . . . .
C4 C 0.5086(3) 0.17502(19) 0.73780(14) 0.0629(9) Uani 1 1 d . . . . .
H4 H 0.4479 0.1584 0.7206 0.075 Uiso 1 1 calc R . . . .
C5 C 0.5113(3) 0.2126(2) 0.79858(17) 0.0826(11) Uani 1 1 d . . . . .
H5 H 0.4525 0.2201 0.8226 0.099 Uiso 1 1 calc R . . . .
C6 C 0.6001(3) 0.2389(2) 0.82347(16) 0.0751(11) Uani 1 1 d . . . . .
H6A H 0.6013 0.2651 0.8638 0.090 Uiso 1 1 calc R . . . .
C7 C 0.6870(3) 0.22658(18) 0.78921(16) 0.0628(9) Uani 1 1 d . . . . .
H7 H 0.7474 0.2439 0.8066 0.075 Uiso 1 1 calc R . . . .
C8 C 0.6857(2) 0.18837(16) 0.72864(14) 0.0499(7) Uani 1 1 d . . . . .
H8 H 0.7451 0.1804 0.7055 0.060 Uiso 1 1 calc R . . . .
C9 C 0.7170(2) 0.03373(15) 0.65785(12) 0.0432(7) Uani 1 1 d . . . . .
C10 C 0.8188(2) 0.01441(15) 0.65353(13) 0.0478(7) Uani 1 1 d . . . . .
C11 C 0.8541(3) -0.04082(18) 0.69915(15) 0.0661(9) Uani 1 1 d . . . . .
H11 H 0.9209 -0.0552 0.6970 0.079 Uiso 1 1 calc R . . . .
C12 C 0.7941(3) -0.0738(2) 0.74606(18) 0.0786(11) Uani 1 1 d . . . . .
H12 H 0.8208 -0.1088 0.7759 0.094 Uiso 1 1 calc R . . . .
C13 C 0.6953(3) -0.05547(18) 0.74937(16) 0.0703(10) Uani 1 1 d . . . . .
H13 H 0.6541 -0.0781 0.7811 0.084 Uiso 1 1 calc R . . . .
C14 C 0.6571(2) -0.00325(16) 0.70531(13) 0.0529(7) Uani 1 1 d . . . . .
H14 H 0.5892 0.0080 0.7070 0.064 Uiso 1 1 calc R . . . .
C15 C 0.8914(2) 0.04701(16) 0.60641(14) 0.0486(7) Uani 1 1 d . . . . .
C16 C 1.0015(2) 0.0353(2) 0.61793(17) 0.0749(10) Uani 1 1 d . . . . .
H16A H 1.0146 0.0340 0.6652 0.112 Uiso 1 1 calc GR . . . .
H16B H 1.0382 0.0762 0.5980 0.112 Uiso 1 1 calc GR . . . .
H16C H 1.0219 -0.0116 0.5980 0.112 Uiso 1 1 calc GR . . . .
C17 C 0.91127(19) 0.14964(16) 0.46202(15) 0.0452(7) Uani 1 1 d . . . . .
C18 C 1.0873(2) 0.1796(2) 0.4413(2) 0.0816(11) Uani 1 1 d . . . . .
H18A H 1.1272 0.1985 0.4050 0.122 Uiso 1 1 calc GR . . . .
H18B H 1.1078 0.1290 0.4520 0.122 Uiso 1 1 calc GR . . . .
H18C H 1.0961 0.2114 0.4798 0.122 Uiso 1 1 calc GR . . . .
C19 C 0.3534(2) 0.10039(16) 0.45764(13) 0.0446(7) Uani 1 1 d . . . . .
H19A H 0.2880 0.0769 0.4605 0.054 Uiso 1 1 calc R . . . .
H19B H 0.3981 0.0653 0.4353 0.054 Uiso 1 1 calc R . . . .
C20 C 0.3457(2) 0.1717(2) 0.41706(15) 0.0615(9) Uani 1 1 d . . . . .
H20A H 0.3165 0.1604 0.3743 0.092 Uiso 1 1 calc GR . . . .
H20B H 0.4113 0.1927 0.4107 0.092 Uiso 1 1 calc GR . . . .
H20C H 0.3044 0.2076 0.4403 0.092 Uiso 1 1 calc GR . . . .
C21 C 0.3149(2) 0.12892(17) 0.57732(14) 0.0464(7) Uani 1 1 d . . . . .
H21A H 0.2544 0.1481 0.5565 0.056 Uiso 1 1 calc R . . . .
H21B H 0.3395 0.1673 0.6079 0.056 Uiso 1 1 calc R . . . .
C22 C 0.2903(3) 0.0589(2) 0.61607(19) 0.0773(11) Uani 1 1 d . . . . .
H22A H 0.2637 0.0213 0.5863 0.116 Uiso 1 1 calc GR . . . .
H22B H 0.2416 0.0706 0.6498 0.116 Uiso 1 1 calc GR . . . .
H22C H 0.3499 0.0398 0.6369 0.116 Uiso 1 1 calc GR . . . .


_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
Cu1 S1 2.2447(7) . ?
Cu1 S2 2.2300(8) . ?
Cu1 N3 1.932(2) . ?
Cu1 N4 1.981(2) . ?
S1 C1 1.720(2) . ?
S2 C17 1.739(3) . ?
N1 C1 1.329(3) . ?
N1 C19 1.461(3) . ?
N1 C21 1.473(3) . ?
N2 C1 1.353(3) . ?
N2 C2 1.308(3) . ?
N3 C2 1.353(3) . ?
N3 C9 1.400(3) . ?
N4 N5 1.392(3) . ?
N4 C15 1.308(3) . ?
N5 C17 1.295(4) . ?
N6 H6 0.8600 . ?
N6 C17 1.353(4) . ?
N6 C18 1.451(4) . ?
C2 C3 1.496(3) . ?
C3 C4 1.387(4) . ?
C3 C8 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(5) . ?
C6 H6A 0.9300 . ?
C6 C7 1.366(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.405(4) . ?
C9 C14 1.403(4) . ?
C10 C11 1.416(4) . ?
C10 C15 1.469(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.363(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.503(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.502(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.497(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
S2 Cu1 S1 89.58(3) . . ?
N3 Cu1 S1 94.83(7) . . ?
N3 Cu1 S2 164.80(7) . . ?
N3 Cu1 N4 92.22(9) . . ?
N4 Cu1 S1 166.18(7) . . ?
N4 Cu1 S2 86.67(7) . . ?
C1 S1 Cu1 104.91(9) . . ?
C17 S2 Cu1 94.10(10) . . ?
C1 N1 C19 122.0(2) . . ?
C1 N1 C21 121.4(2) . . ?
C19 N1 C21 116.6(2) . . ?
C2 N2 C1 126.8(2) . . ?
C2 N3 Cu1 117.80(16) . . ?
C2 N3 C9 119.0(2) . . ?
C9 N3 Cu1 122.80(17) . . ?
N5 N4 Cu1 118.57(16) . . ?
C15 N4 Cu1 127.2(2) . . ?
C15 N4 N5 114.2(2) . . ?
C17 N5 N4 114.2(2) . . ?
C17 N6 H6 119.3 . . ?
C17 N6 C18 121.4(3) . . ?
C18 N6 H6 119.3 . . ?
N1 C1 S1 119.04(18) . . ?
N1 C1 N2 115.3(2) . . ?
N2 C1 S1 125.35(19) . . ?
N2 C2 N3 126.8(2) . . ?
N2 C2 C3 113.5(2) . . ?
N3 C2 C3 119.5(2) . . ?
C4 C3 C2 119.6(3) . . ?
C8 C3 C2 121.3(3) . . ?
C8 C3 C4 118.9(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6A 119.9 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 120.3(3) . . ?
C3 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
N3 C9 C10 122.9(2) . . ?
N3 C9 C14 118.1(2) . . ?
C14 C9 C10 118.7(2) . . ?
C9 C10 C11 116.8(3) . . ?
C9 C10 C15 125.7(2) . . ?
C11 C10 C15 117.6(3) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 C10 122.8(3) . . ?
C12 C11 H11 118.6 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 H14 118.9 . . ?
C13 C14 C9 122.3(3) . . ?
C13 C14 H14 118.9 . . ?
N4 C15 C10 121.3(2) . . ?
N4 C15 C16 119.1(3) . . ?
C10 C15 C16 119.6(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 S2 126.2(2) . . ?
N5 C17 N6 117.8(2) . . ?
N6 C17 S2 116.0(2) . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.3 . . ?
N1 C19 H19B 109.3 . . ?
N1 C19 C20 111.8(2) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.1 . . ?
N1 C21 H21B 109.1 . . ?
N1 C21 C22 112.4(2) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C16 H16B N5 0.96 2.21 2.611(4) 103.9 .
C19 H19B S1 0.97 2.56 2.949(3) 104.2 .

_olex2_submission_special_instructions 'No special instructions were received'
