# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_0507
_database_code_depnum_ccdc_archive 'CCDC 2155547'
loop_
_audit_author_name
_audit_author_address
'Tosifumi Maruyama'
;gifu university
Japan
;
_audit_update_record             
;
2022-03-01 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 N4 S'
_chemical_formula_sum            'C28 H24 N4 S'
_chemical_formula_weight         448.57

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.407(3)
_cell_length_b                   11.689(4)
_cell_length_c                   12.393(4)
_cell_angle_alpha                115.971(4)
_cell_angle_beta                 102.307(2)
_cell_angle_gamma                91.501(2)
_cell_volume                     1185.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3580
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      31.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury CCD (2x2 bin mode)'
_diffrn_measurement_method       'profile data from φ-scans'
_diffrn_detector_area_resol_mean 14.6306
_diffrn_reflns_number            10688
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.888
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5374
_reflns_number_gt                3854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0786P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5374
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_refine_ls_shift/su_max          0.000
_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_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 0.79535(5) 0.14189(4) 0.76555(4) 0.05082(15) Uani 1 1 d . . . . .
N1 N 1.03698(14) 0.10303(12) 0.69807(12) 0.0423(3) Uani 1 1 d . . . . .
N2 N 0.73697(15) -0.11708(12) 0.67996(12) 0.0445(3) Uani 1 1 d . . . . .
N3 N 0.90479(17) 0.40738(14) 0.83516(15) 0.0582(4) Uani 1 1 d . . . . .
N4 N 1.01136(18) -0.23219(14) 0.63041(15) 0.0585(4) Uani 1 1 d . . . . .
C1 C 0.95890(17) 0.19314(15) 0.74748(15) 0.0424(4) Uani 1 1 d . . . . .
C2 C 0.97096(16) -0.01653(14) 0.67253(14) 0.0401(4) Uani 1 1 d . . . . .
C3 C 0.83797(17) -0.01420(15) 0.70291(14) 0.0425(4) Uani 1 1 d . . . . .
C4 C 0.66546(16) -0.20227(15) 0.55540(14) 0.0415(4) Uani 1 1 d . . . . .
C5 C 0.62060(17) -0.15562(16) 0.46943(15) 0.0454(4) Uani 1 1 d . . . . .
H5 H 0.6362 -0.0659 0.4951 0.054 Uiso 1 1 calc R U . . .
C6 C 0.55382(18) -0.23838(18) 0.34758(16) 0.0500(4) Uani 1 1 d . . . . .
H6 H 0.5265 -0.2044 0.2903 0.060 Uiso 1 1 calc R U . . .
C7 C 0.52520(18) -0.36985(18) 0.30590(15) 0.0509(4) Uani 1 1 d . . . . .
C8 C 0.5681(2) -0.41512(17) 0.39307(16) 0.0543(4) Uani 1 1 d . . . . .
H8 H 0.5481 -0.5044 0.3681 0.065 Uiso 1 1 calc R U . . .
C9 C 0.6388(2) -0.33384(16) 0.51492(16) 0.0513(4) Uani 1 1 d . . . . .
H9 H 0.6695 -0.3682 0.5715 0.062 Uiso 1 1 calc R U . . .
C10 C 0.4545(2) -0.4590(2) 0.17150(17) 0.0699(6) Uani 1 1 d . . . . .
H10 H 0.3663 -0.4266 0.1436 0.105 Uiso 1 1 calc R U . . .
H10A H 0.4273 -0.5449 0.1622 0.105 Uiso 1 1 calc R U . . .
H10B H 0.5239 -0.4634 0.1215 0.105 Uiso 1 1 calc R U . . .
C11 C 0.69750(16) -0.12472(14) 0.78134(14) 0.0383(3) Uani 1 1 d . . . . .
C12 C 0.55758(18) -0.17836(17) 0.76888(16) 0.0509(4) Uani 1 1 d . . . . .
H12 H 0.4865 -0.2109 0.6917 0.061 Uiso 1 1 calc R U . . .
C13 C 0.5222(2) -0.18425(18) 0.86949(17) 0.0563(5) Uani 1 1 d . . . . .
H13 H 0.4263 -0.2214 0.8595 0.068 Uiso 1 1 calc R U . . .
C14 C 0.6208(2) -0.13830(16) 0.98325(15) 0.0499(4) Uani 1 1 d . . . . .
C15 C 0.7585(2) -0.08334(18) 0.99476(16) 0.0540(4) Uani 1 1 d . . . . .
H15 H 0.8285 -0.0491 1.0726 0.065 Uiso 1 1 calc R U . . .
C16 C 0.79713(18) -0.07689(16) 0.89503(14) 0.0468(4) Uani 1 1 d . . . . .
H16 H 0.8929 -0.0392 0.9055 0.056 Uiso 1 1 calc R U . . .
C17 C 0.5810(3) -0.1466(2) 1.09235(18) 0.0748(6) Uani 1 1 d . . . . .
H17 H 0.4942 -0.1038 1.1086 0.112 Uiso 1 1 calc R U . . .
H17A H 0.6634 -0.1044 1.1659 0.112 Uiso 1 1 calc R U . . .
H17B H 0.5596 -0.2370 1.0729 0.112 Uiso 1 1 calc R U . . .
C18 C 0.9382(2) 0.53158(17) 0.86866(19) 0.0612(5) Uani 1 1 d . . . . .
H18 H 0.8719 0.5877 0.9049 0.073 Uiso 1 1 calc R U . . .
C19 C 1.0616(2) 0.58555(16) 0.85490(17) 0.0520(4) Uani 1 1 d . . . . .
C20 C 1.1538(2) 0.50225(17) 0.80055(19) 0.0592(5) Uani 1 1 d . . . . .
H20 H 1.2394 0.5342 0.7878 0.071 Uiso 1 1 calc R U . . .
C21 C 1.12410(19) 0.37251(17) 0.76389(19) 0.0568(5) Uani 1 1 d . . . . .
H21 H 1.1880 0.3146 0.7260 0.068 Uiso 1 1 calc R U . . .
C22 C 0.99812(18) 0.32902(15) 0.78397(15) 0.0441(4) Uani 1 1 d . . . . .
C23 C 1.0883(3) 0.72667(18) 0.8966(2) 0.0728(6) Uani 1 1 d . . . . .
H23 H 1.1939 0.7567 0.9299 0.109 Uiso 1 1 calc R U . . .
H23A H 1.0368 0.7715 0.9611 0.109 Uiso 1 1 calc R U . . .
H23B H 1.0517 0.7444 0.8260 0.109 Uiso 1 1 calc R U . . .
C24 C 1.04742(17) -0.12748(15) 0.61816(14) 0.0415(4) Uani 1 1 d . . . . .
C25 C 1.15631(18) -0.12182(16) 0.55916(15) 0.0481(4) Uani 1 1 d . . . . .
H25 H 1.1823 -0.0454 0.5543 0.058 Uiso 1 1 calc R U . . .
C26 C 1.2256(2) -0.22757(18) 0.50812(17) 0.0575(5) Uani 1 1 d . . . . .
H26 H 1.2978 -0.2261 0.4654 0.069 Uiso 1 1 calc R U . . .
C27 C 1.1891(2) -0.33546(18) 0.51973(18) 0.0631(5) Uani 1 1 d . . . . .
H27 H 1.2356 -0.4099 0.4860 0.076 Uiso 1 1 calc R U . . .
C28 C 1.0827(2) -0.33230(18) 0.5820(2) 0.0684(6) Uani 1 1 d . . . . .
H28 H 1.0587 -0.4066 0.5909 0.082 Uiso 1 1 calc R U . . .


_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 1.7299(15) . ?
S1 C3 1.7386(18) . ?
N1 C1 1.300(2) . ?
N1 C2 1.3865(18) . ?
N2 C3 1.3983(18) . ?
N2 C4 1.415(2) . ?
N2 C11 1.4212(17) . ?
N3 C18 1.331(2) . ?
N3 C22 1.335(2) . ?
N4 C28 1.334(3) . ?
N4 C24 1.3413(18) . ?
C1 C22 1.460(2) . ?
C2 C3 1.379(2) . ?
C2 C24 1.464(2) . ?
C4 C9 1.389(2) . ?
C4 C5 1.393(2) . ?
C5 C6 1.377(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.391(2) . ?
C7 C10 1.508(2) . ?
C8 C9 1.381(2) . ?
C11 C16 1.377(2) . ?
C11 C12 1.391(2) . ?
C12 C13 1.386(2) . ?
C13 C14 1.375(2) . ?
C14 C15 1.381(2) . ?
C14 C17 1.519(2) . ?
C15 C16 1.392(2) . ?
C18 C19 1.384(2) . ?
C19 C20 1.368(3) . ?
C19 C23 1.493(2) . ?
C20 C21 1.380(2) . ?
C21 C22 1.389(2) . ?
C24 C25 1.395(2) . ?
C25 C26 1.373(2) . ?
C26 C27 1.373(2) . ?
C27 C28 1.380(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
C1 S1 C3 88.79(7) . . ?
C1 N1 C2 111.72(13) . . ?
C3 N2 C4 118.34(11) . . ?
C3 N2 C11 119.26(13) . . ?
C4 N2 C11 122.02(11) . . ?
C18 N3 C22 117.08(15) . . ?
C28 N4 C24 117.12(15) . . ?
N1 C1 C22 124.94(13) . . ?
N1 C1 S1 115.27(11) . . ?
C22 C1 S1 119.77(12) . . ?
C3 C2 N1 113.88(14) . . ?
C3 C2 C24 128.17(13) . . ?
N1 C2 C24 117.95(13) . . ?
C2 C3 N2 128.95(15) . . ?
C2 C3 S1 110.33(10) . . ?
N2 C3 S1 120.45(12) . . ?
C9 C4 C5 118.11(15) . . ?
C9 C4 N2 121.52(13) . . ?
C5 C4 N2 120.37(14) . . ?
C6 C5 C4 120.58(15) . . ?
C5 C6 C7 122.03(15) . . ?
C6 C7 C8 116.88(16) . . ?
C6 C7 C10 121.12(16) . . ?
C8 C7 C10 121.98(18) . . ?
C9 C8 C7 121.84(16) . . ?
C8 C9 C4 120.53(15) . . ?
C16 C11 C12 118.58(13) . . ?
C16 C11 N2 120.32(13) . . ?
C12 C11 N2 121.09(14) . . ?
C13 C12 C11 119.77(15) . . ?
C14 C13 C12 122.41(15) . . ?
C13 C14 C15 117.14(14) . . ?
C13 C14 C17 121.82(16) . . ?
C15 C14 C17 121.03(17) . . ?
C14 C15 C16 121.61(16) . . ?
C11 C16 C15 120.47(15) . . ?
N3 C18 C19 125.22(18) . . ?
C20 C19 C18 116.14(16) . . ?
C20 C19 C23 123.27(17) . . ?
C18 C19 C23 120.59(17) . . ?
C19 C20 C21 120.95(16) . . ?
C20 C21 C22 118.07(17) . . ?
N3 C22 C21 122.54(15) . . ?
N3 C22 C1 116.10(14) . . ?
C21 C22 C1 121.35(15) . . ?
N4 C24 C25 121.88(15) . . ?
N4 C24 C2 117.46(13) . . ?
C25 C24 C2 120.63(13) . . ?
C26 C25 C24 119.48(14) . . ?
C25 C26 C27 119.08(17) . . ?
C26 C27 C28 117.87(18) . . ?
N4 C28 C27 124.53(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
C2 N1 C1 C22 -179.49(14) . . . . ?
C2 N1 C1 S1 -1.15(17) . . . . ?
C3 S1 C1 N1 0.86(13) . . . . ?
C3 S1 C1 C22 179.30(13) . . . . ?
C1 N1 C2 C3 0.88(18) . . . . ?
C1 N1 C2 C24 -179.12(12) . . . . ?
N1 C2 C3 N2 173.78(14) . . . . ?
C24 C2 C3 N2 -6.2(3) . . . . ?
N1 C2 C3 S1 -0.24(16) . . . . ?
C24 C2 C3 S1 179.77(12) . . . . ?
C4 N2 C3 C2 -65.4(2) . . . . ?
C11 N2 C3 C2 121.51(17) . . . . ?
C4 N2 C3 S1 108.11(15) . . . . ?
C11 N2 C3 S1 -65.00(18) . . . . ?
C1 S1 C3 C2 -0.32(12) . . . . ?
C1 S1 C3 N2 -174.92(12) . . . . ?
C3 N2 C4 C9 140.79(16) . . . . ?
C11 N2 C4 C9 -46.3(2) . . . . ?
C3 N2 C4 C5 -38.7(2) . . . . ?
C11 N2 C4 C5 134.16(15) . . . . ?
C9 C4 C5 C6 -0.9(2) . . . . ?
N2 C4 C5 C6 178.60(14) . . . . ?
C4 C5 C6 C7 1.6(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C5 C6 C7 C10 -178.85(16) . . . . ?
C6 C7 C8 C9 -1.4(2) . . . . ?
C10 C7 C8 C9 177.01(17) . . . . ?
C7 C8 C9 C4 2.1(3) . . . . ?
C5 C4 C9 C8 -0.8(2) . . . . ?
N2 C4 C9 C8 179.62(15) . . . . ?
C3 N2 C11 C16 -31.1(2) . . . . ?
C4 N2 C11 C16 156.06(15) . . . . ?
C3 N2 C11 C12 147.84(16) . . . . ?
C4 N2 C11 C12 -25.0(2) . . . . ?
C16 C11 C12 C13 -0.9(2) . . . . ?
N2 C11 C12 C13 -179.87(16) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C12 C13 C14 C17 -179.38(18) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C17 C14 C15 C16 179.00(18) . . . . ?
C12 C11 C16 C15 0.6(2) . . . . ?
N2 C11 C16 C15 179.51(15) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C22 N3 C18 C19 -0.2(3) . . . . ?
N3 C18 C19 C20 1.1(3) . . . . ?
N3 C18 C19 C23 -179.68(19) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
C23 C19 C20 C21 179.88(18) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C18 N3 C22 C21 -0.9(3) . . . . ?
C18 N3 C22 C1 -179.74(15) . . . . ?
C20 C21 C22 N3 1.1(3) . . . . ?
C20 C21 C22 C1 179.82(16) . . . . ?
N1 C1 C22 N3 -178.94(15) . . . . ?
S1 C1 C22 N3 2.8(2) . . . . ?
N1 C1 C22 C21 2.2(3) . . . . ?
S1 C1 C22 C21 -176.04(14) . . . . ?
C28 N4 C24 C25 -1.0(3) . . . . ?
C28 N4 C24 C2 -179.20(16) . . . . ?
C3 C2 C24 N4 -21.2(2) . . . . ?
N1 C2 C24 N4 158.83(14) . . . . ?
C3 C2 C24 C25 160.57(16) . . . . ?
N1 C2 C24 C25 -19.4(2) . . . . ?
N4 C24 C25 C26 2.3(2) . . . . ?
C2 C24 C25 C26 -179.52(15) . . . . ?
C24 C25 C26 C27 -2.0(3) . . . . ?
C25 C26 C27 C28 0.5(3) . . . . ?
C24 N4 C28 C27 -0.6(3) . . . . ?
C26 C27 C28 N4 0.9(3) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_0613
_database_code_depnum_ccdc_archive 'CCDC 2155549'
loop_
_audit_author_name
_audit_author_address
'Tosifumi Maruyama'
;Gifu University
Japan
;
_audit_update_record             
;
2022-03-01 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 Cl2 N4 Ni S'
_chemical_formula_sum            'C28 H24 Cl2 N4 Ni S'
_chemical_formula_weight         578.18

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   15.9050(11)
_cell_length_b                   8.6642(4)
_cell_length_c                   20.5670(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.528(6)
_cell_angle_gamma                90
_cell_volume                     2702.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7193
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      31.0

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.017
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Mercury CCD (2x2 bin mode)'
_diffrn_measurement_method       'profile data from φ-scans'
_diffrn_detector_area_resol_mean 14.6306
_diffrn_reflns_number            23061
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.929
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6205
_reflns_number_gt                4449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0997P)²+0.9050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6205
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1997
_refine_ls_wR_factor_gt          0.1722
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_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 0.42856(3) 0.03335(6) 0.91484(2) 0.03147(18) Uani 1 1 d . . . . .
Cl1 Cl 0.42328(6) 0.07961(12) 1.02679(4) 0.0374(3) Uani 1 1 d . . . . .
Cl2 Cl 0.28708(7) 0.13184(13) 0.86274(5) 0.0443(3) Uani 1 1 d . . . . .
N1 N 0.4471(2) -0.0140(4) 0.82650(14) 0.0336(7) Uani 1 1 d . . . . .
N2 N 0.37630(19) -0.1973(4) 0.89289(14) 0.0319(7) Uani 1 1 d . . . . .
N3 N 0.4924(2) 0.2403(4) 0.88962(14) 0.0343(7) Uani 1 1 d . . . . .
S1 S 0.45223(8) -0.16756(13) 0.72411(5) 0.0442(3) Uani 1 1 d . . . . .
N4 N 0.5401(2) 0.0770(4) 0.69056(17) 0.0453(9) Uani 1 1 d . . . . .
C1 C 0.4231(3) -0.1458(5) 0.79748(17) 0.0362(9) Uani 1 1 d . . . . .
C2 C 0.5022(3) 0.0162(5) 0.73758(18) 0.0394(9) Uani 1 1 d . . . . .
C3 C 0.4906(2) 0.0819(5) 0.79526(16) 0.0353(9) Uani 1 1 d . . . . .
C4 C 0.3355(2) -0.2837(5) 0.92809(19) 0.0384(9) Uani 1 1 d . . . . .
H4 H 0.3332 -0.2464 0.9699 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2962(3) -0.4257(5) 0.90634(19) 0.0404(9) Uani 1 1 d . . . . .
C6 C 0.2996(3) -0.4780(5) 0.8431(2) 0.0441(10) Uani 1 1 d . . . . .
H6 H 0.2744 -0.5725 0.8265 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3398(3) -0.3914(5) 0.80527(19) 0.0417(10) Uani 1 1 d . . . . .
H7 H 0.3414 -0.4255 0.7628 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3778(2) -0.2527(5) 0.83139(17) 0.0335(8) Uani 1 1 d . . . . .
C9 C 0.2539(3) -0.5158(6) 0.9496(2) 0.0531(12) Uani 1 1 d . . . . .
H9 H 0.1921 -0.5271 0.9263 0.080 Uiso 1 1 calc R U . . .
H9A H 0.2616 -0.4626 0.9920 0.080 Uiso 1 1 calc R U . . .
H9B H 0.2808 -0.6160 0.9586 0.080 Uiso 1 1 calc R U . . .
C10 C 0.5153(2) 0.2295(5) 0.83073(17) 0.0344(8) Uani 1 1 d . . . . .
C11 C 0.5559(3) 0.3503(5) 0.8084(2) 0.0446(10) Uani 1 1 d . . . . .
H11 H 0.5710 0.3415 0.7682 0.054 Uiso 1 1 calc R U . . .
C12 C 0.5738(3) 0.4848(5) 0.8464(2) 0.0483(11) Uani 1 1 d . . . . .
H12 H 0.6022 0.5666 0.8325 0.058 Uiso 1 1 calc R U . . .
C13 C 0.5493(3) 0.4961(6) 0.9048(2) 0.0477(11) Uani 1 1 d . . . . .
H13 H 0.5592 0.5863 0.9305 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5095(3) 0.3701(5) 0.92444(19) 0.0403(9) Uani 1 1 d . . . . .
H14 H 0.4940 0.3774 0.9644 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5928(3) -0.0245(5) 0.66377(19) 0.0430(10) Uani 1 1 d . . . . .
C16 C 0.6587(3) -0.1116(6) 0.7087(2) 0.0512(12) Uani 1 1 d . . . . .
H16 H 0.6698 -0.0999 0.7554 0.061 Uiso 1 1 calc R U . . .
C17 C 0.7074(3) -0.2146(6) 0.6842(2) 0.0568(13) Uani 1 1 d . . . . .
H17 H 0.7509 -0.2723 0.7149 0.068 Uiso 1 1 calc R U . . .
C18 C 0.6935(3) -0.2348(6) 0.6151(2) 0.0517(12) Uani 1 1 d . . . . .
C19 C 0.6277(3) -0.1465(7) 0.5707(2) 0.0576(13) Uani 1 1 d . . . . .
H19 H 0.6171 -0.1575 0.5239 0.069 Uiso 1 1 calc R U . . .
C20 C 0.5777(3) -0.0427(6) 0.5946(2) 0.0507(12) Uani 1 1 d . . . . .
H20 H 0.5340 0.0147 0.5639 0.061 Uiso 1 1 calc R U . . .
C21 C 0.7458(4) -0.3511(8) 0.5878(3) 0.0732(17) Uani 1 1 d . . . . .
H21 H 0.7987 -0.3033 0.5842 0.110 Uiso 1 1 calc R U . . .
H21A H 0.7109 -0.3860 0.5437 0.110 Uiso 1 1 calc R U . . .
H21B H 0.7610 -0.4375 0.6184 0.110 Uiso 1 1 calc R U . . .
C22 C 0.5032(3) 0.2138(5) 0.65396(17) 0.0416(10) Uani 1 1 d . . . . .
C23 C 0.5558(3) 0.3107(6) 0.6285(2) 0.0520(11) Uani 1 1 d . . . . .
H23 H 0.6140 0.2837 0.6332 0.062 Uiso 1 1 calc R U . . .
C24 C 0.5217(4) 0.4466(6) 0.5962(2) 0.0559(13) Uani 1 1 d . . . . .
H24 H 0.5574 0.5109 0.5797 0.067 Uiso 1 1 calc R U . . .
C25 C 0.4340(3) 0.4895(6) 0.5880(2) 0.0471(11) Uani 1 1 d . . . . .
C26 C 0.3830(3) 0.3925(6) 0.6139(2) 0.0468(10) Uani 1 1 d . . . . .
H26 H 0.3251 0.4197 0.6097 0.056 Uiso 1 1 calc R U . . .
C27 C 0.4166(3) 0.2554(5) 0.64597(19) 0.0431(10) Uani 1 1 d . . . . .
H27 H 0.3807 0.1908 0.6622 0.052 Uiso 1 1 calc R U . . .
C28 C 0.3978(4) 0.6399(6) 0.5533(2) 0.0628(14) Uani 1 1 d . . . . .
H28 H 0.3444 0.6658 0.5635 0.094 Uiso 1 1 calc R U . . .
H28A H 0.3854 0.6289 0.5048 0.094 Uiso 1 1 calc R U . . .
H28B H 0.4404 0.7204 0.5694 0.094 Uiso 1 1 calc R U . . .


_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 1.970(3) . ?
Ni1 N2 2.159(3) . ?
Ni1 N3 2.199(3) . ?
Ni1 Cl2 2.3425(11) . ?
Ni1 Cl1 2.3632(9) . ?
Ni1 Cl1 2.4996(11) 3_657 ?
Cl1 Ni1 2.4996(10) 3_657 ?
N1 C1 1.292(5) . ?
N1 C3 1.360(5) . ?
N2 C4 1.337(5) . ?
N2 C8 1.359(5) . ?
N3 C14 1.317(5) . ?
N3 C10 1.369(5) . ?
S1 C1 1.717(4) . ?
S1 C2 1.764(5) . ?
N4 C2 1.388(5) . ?
N4 C22 1.432(5) . ?
N4 C15 1.435(6) . ?
C1 C8 1.472(6) . ?
C2 C3 1.377(5) . ?
C3 C10 1.466(6) . ?
C4 C5 1.392(6) . ?
C5 C6 1.394(6) . ?
C5 C9 1.488(6) . ?
C6 C7 1.369(6) . ?
C7 C8 1.380(6) . ?
C10 C11 1.379(6) . ?
C11 C12 1.384(6) . ?
C12 C13 1.374(6) . ?
C13 C14 1.382(6) . ?
C15 C20 1.379(5) . ?
C15 C16 1.392(6) . ?
C16 C17 1.372(7) . ?
C17 C18 1.380(6) . ?
C18 C19 1.393(7) . ?
C18 C21 1.518(7) . ?
C19 C20 1.384(7) . ?
C22 C27 1.385(6) . ?
C22 C23 1.394(6) . ?
C23 C24 1.380(7) . ?
C24 C25 1.404(7) . ?
C25 C26 1.381(7) . ?
C25 C28 1.514(7) . ?
C26 C27 1.386(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
N1 Ni1 N2 76.67(13) . . ?
N1 Ni1 N3 75.18(12) . . ?
N2 Ni1 N3 151.85(12) . . ?
N1 Ni1 Cl2 92.51(10) . . ?
N2 Ni1 Cl2 89.16(8) . . ?
N3 Ni1 Cl2 92.48(8) . . ?
N1 Ni1 Cl1 173.31(10) . . ?
N2 Ni1 Cl1 103.67(8) . . ?
N3 Ni1 Cl1 104.24(8) . . ?
Cl2 Ni1 Cl1 94.17(4) . . ?
N1 Ni1 Cl1 88.87(10) . 3_657 ?
N2 Ni1 Cl1 89.19(8) . 3_657 ?
N3 Ni1 Cl1 89.84(8) . 3_657 ?
Cl2 Ni1 Cl1 177.55(4) . 3_657 ?
Cl1 Ni1 Cl1 84.46(4) . 3_657 ?
Ni1 Cl1 Ni1 95.54(4) . 3_657 ?
C1 N1 C3 116.3(3) . . ?
C1 N1 Ni1 120.3(3) . . ?
C3 N1 Ni1 123.2(3) . . ?
C4 N2 C8 117.0(3) . . ?
C4 N2 Ni1 128.6(3) . . ?
C8 N2 Ni1 114.1(3) . . ?
C14 N3 C10 118.2(3) . . ?
C14 N3 Ni1 127.1(3) . . ?
C10 N3 Ni1 114.7(3) . . ?
C1 S1 C2 89.48(19) . . ?
C2 N4 C22 119.1(4) . . ?
C2 N4 C15 117.5(4) . . ?
C22 N4 C15 120.0(3) . . ?
N1 C1 C8 117.1(3) . . ?
N1 C1 S1 112.5(3) . . ?
C8 C1 S1 130.4(3) . . ?
C3 C2 N4 130.0(4) . . ?
C3 C2 S1 109.7(3) . . ?
N4 C2 S1 120.2(3) . . ?
N1 C3 C2 111.9(4) . . ?
N1 C3 C10 113.3(3) . . ?
C2 C3 C10 134.7(4) . . ?
N2 C4 C5 124.4(4) . . ?
C4 C5 C6 116.6(4) . . ?
C4 C5 C9 120.8(4) . . ?
C6 C5 C9 122.7(4) . . ?
C7 C6 C5 120.5(4) . . ?
C6 C7 C8 118.7(4) . . ?
N2 C8 C7 122.8(4) . . ?
N2 C8 C1 111.5(3) . . ?
C7 C8 C1 125.7(3) . . ?
N3 C10 C11 121.3(4) . . ?
N3 C10 C3 113.4(3) . . ?
C11 C10 C3 125.3(4) . . ?
C10 C11 C12 119.2(4) . . ?
C13 C12 C11 119.3(4) . . ?
C12 C13 C14 118.4(4) . . ?
N3 C14 C13 123.6(4) . . ?
C20 C15 C16 119.0(4) . . ?
C20 C15 N4 121.7(4) . . ?
C16 C15 N4 119.2(3) . . ?
C17 C16 C15 120.3(4) . . ?
C16 C17 C18 121.8(4) . . ?
C17 C18 C19 117.5(4) . . ?
C17 C18 C21 121.9(5) . . ?
C19 C18 C21 120.6(4) . . ?
C20 C19 C18 121.4(4) . . ?
C15 C20 C19 120.0(4) . . ?
C27 C22 C23 119.1(4) . . ?
C27 C22 N4 120.8(4) . . ?
C23 C22 N4 119.9(4) . . ?
C24 C23 C22 120.0(4) . . ?
C23 C24 C25 121.1(5) . . ?
C26 C25 C24 118.0(4) . . ?
C26 C25 C28 121.4(5) . . ?
C24 C25 C28 120.5(5) . . ?
C25 C26 C27 121.2(4) . . ?
C22 C27 C26 120.4(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C8 178.6(3) . . . . ?
Ni1 N1 C1 C8 3.3(5) . . . . ?
C3 N1 C1 S1 -0.5(4) . . . . ?
Ni1 N1 C1 S1 -175.79(17) . . . . ?
C2 S1 C1 N1 1.4(3) . . . . ?
C2 S1 C1 C8 -177.5(4) . . . . ?
C22 N4 C2 C3 -59.4(6) . . . . ?
C15 N4 C2 C3 141.6(4) . . . . ?
C22 N4 C2 S1 115.6(4) . . . . ?
C15 N4 C2 S1 -43.3(5) . . . . ?
C1 S1 C2 C3 -1.9(3) . . . . ?
C1 S1 C2 N4 -177.9(3) . . . . ?
C1 N1 C3 C2 -1.0(5) . . . . ?
Ni1 N1 C3 C2 174.1(3) . . . . ?
C1 N1 C3 C10 179.6(3) . . . . ?
Ni1 N1 C3 C10 -5.2(4) . . . . ?
N4 C2 C3 N1 177.5(4) . . . . ?
S1 C2 C3 N1 2.0(4) . . . . ?
N4 C2 C3 C10 -3.4(8) . . . . ?
S1 C2 C3 C10 -178.9(4) . . . . ?
C8 N2 C4 C5 1.0(6) . . . . ?
Ni1 N2 C4 C5 173.3(3) . . . . ?
N2 C4 C5 C6 -0.8(6) . . . . ?
N2 C4 C5 C9 178.6(4) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C9 C5 C6 C7 -179.6(4) . . . . ?
C5 C6 C7 C8 0.9(6) . . . . ?
C4 N2 C8 C7 -0.3(5) . . . . ?
Ni1 N2 C8 C7 -173.7(3) . . . . ?
C4 N2 C8 C1 179.0(3) . . . . ?
Ni1 N2 C8 C1 5.6(4) . . . . ?
C6 C7 C8 N2 -0.7(6) . . . . ?
C6 C7 C8 C1 -179.8(4) . . . . ?
N1 C1 C8 N2 -5.9(5) . . . . ?
S1 C1 C8 N2 173.0(3) . . . . ?
N1 C1 C8 C7 173.3(4) . . . . ?
S1 C1 C8 C7 -7.8(6) . . . . ?
C14 N3 C10 C11 0.6(5) . . . . ?
Ni1 N3 C10 C11 -180.0(3) . . . . ?
C14 N3 C10 C3 -178.2(3) . . . . ?
Ni1 N3 C10 C3 1.2(4) . . . . ?
N1 C3 C10 N3 2.1(5) . . . . ?
C2 C3 C10 N3 -177.0(4) . . . . ?
N1 C3 C10 C11 -176.6(4) . . . . ?
C2 C3 C10 C11 4.2(7) . . . . ?
N3 C10 C11 C12 0.1(6) . . . . ?
C3 C10 C11 C12 178.7(4) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
C11 C12 C13 C14 1.7(6) . . . . ?
C10 N3 C14 C13 0.0(6) . . . . ?
Ni1 N3 C14 C13 -179.4(3) . . . . ?
C12 C13 C14 N3 -1.2(6) . . . . ?
C2 N4 C15 C20 127.1(5) . . . . ?
C22 N4 C15 C20 -31.6(7) . . . . ?
C2 N4 C15 C16 -50.3(6) . . . . ?
C22 N4 C15 C16 151.0(4) . . . . ?
C20 C15 C16 C17 -0.4(8) . . . . ?
N4 C15 C16 C17 177.1(5) . . . . ?
C15 C16 C17 C18 0.4(8) . . . . ?
C16 C17 C18 C19 -0.1(8) . . . . ?
C16 C17 C18 C21 -178.7(5) . . . . ?
C17 C18 C19 C20 -0.3(8) . . . . ?
C21 C18 C19 C20 178.3(5) . . . . ?
C16 C15 C20 C19 0.1(8) . . . . ?
N4 C15 C20 C19 -177.3(5) . . . . ?
C18 C19 C20 C15 0.3(8) . . . . ?
C2 N4 C22 C27 -22.6(6) . . . . ?
C15 N4 C22 C27 135.8(4) . . . . ?
C2 N4 C22 C23 154.5(4) . . . . ?
C15 N4 C22 C23 -47.1(6) . . . . ?
C27 C22 C23 C24 0.5(7) . . . . ?
N4 C22 C23 C24 -176.7(4) . . . . ?
C22 C23 C24 C25 -0.5(7) . . . . ?
C23 C24 C25 C26 0.8(7) . . . . ?
C23 C24 C25 C28 179.3(4) . . . . ?
C24 C25 C26 C27 -1.2(7) . . . . ?
C28 C25 C26 C27 -179.6(4) . . . . ?
C23 C22 C27 C26 -0.9(6) . . . . ?
N4 C22 C27 C26 176.3(4) . . . . ?
C25 C26 C27 C22 1.2(6) . . . . ?

_refine_diff_density_max         1.420
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.116

