# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_6555
_database_code_depnum_ccdc_archive 'CCDC 1945309'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2019-10-07 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         'C46 H58 N6 Zn2'
_chemical_formula_sum            'C46 H58 N6 Zn2'
_chemical_formula_weight         825.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Zn Zn -1.5491 0.6778 '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'
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'

_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                   10.3684(3)
_cell_length_b                   18.0523(6)
_cell_length_c                   11.7948(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.385(3)
_cell_angle_gamma                90
_cell_volume                     2203.82(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4222
_cell_measurement_theta_min      3.7510
_cell_measurement_theta_max      71.1339

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.615
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80551
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8719
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.483
_diffrn_reflns_theta_max         71.273
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4166
_reflns_number_gt                3387
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_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)+(0.0781P)²+0.1464P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4166
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
Zn1 Zn 0.07241(3) 0.06176(2) 0.04867(3) 0.03198(14) Uani 1 1 d . . . . .
N1 N -0.0501(2) 0.04443(12) -0.08314(18) 0.0344(5) Uani 1 1 d . . . . .
N2 N -0.1302(2) 0.06851(12) -0.27510(18) 0.0375(5) Uani 1 1 d . . . . .
N3 N -0.1355(2) 0.16075(11) -0.15433(17) 0.0341(5) Uani 1 1 d . . . . .
C1 C -0.0995(2) 0.08617(14) -0.1615(2) 0.0331(5) Uani 1 1 d . . . . .
C2 C -0.1830(3) 0.12994(16) -0.3322(2) 0.0437(7) Uani 1 1 d . . . . .
H2 H -0.2112 0.1314 -0.4085 0.052 Uiso 1 1 calc R U . . .
C3 C -0.1864(3) 0.18595(16) -0.2596(2) 0.0416(6) Uani 1 1 d . . . . .
H3 H -0.2172 0.2334 -0.2759 0.050 Uiso 1 1 calc R U . . .
C4 C -0.0984(3) -0.00010(14) -0.3258(2) 0.0377(6) Uani 1 1 d . . . . .
C5 C -0.1974(3) -0.04628(15) -0.3698(2) 0.0379(6) Uani 1 1 d . . . . .
C6 C -0.1635(3) -0.11404(16) -0.4156(2) 0.0423(6) Uani 1 1 d . . . . .
H6 H -0.2283 -0.1449 -0.4465 0.051 Uiso 1 1 calc R U . . .
C7 C -0.0361(3) -0.13705(16) -0.4167(2) 0.0435(6) Uani 1 1 d . . . . .
C8 C 0.0590(3) -0.08898(17) -0.3752(2) 0.0458(7) Uani 1 1 d . . . . .
H8 H 0.1449 -0.1036 -0.3768 0.055 Uiso 1 1 calc R U . . .
C9 C 0.0322(3) -0.02021(16) -0.3313(2) 0.0408(6) Uani 1 1 d . . . . .
C10 C 0.1393(3) 0.03181(18) -0.2929(2) 0.0493(7) Uani 1 1 d . . . . .
H10A H 0.1499 0.0313 -0.2115 0.074 Uiso 1 1 calc R U . . .
H10B H 0.1182 0.0811 -0.3185 0.074 Uiso 1 1 calc R U . . .
H10C H 0.2183 0.0163 -0.3243 0.074 Uiso 1 1 calc R U . . .
C11 C -0.3374(3) -0.02475(17) -0.3671(3) 0.0506(7) Uani 1 1 d . . . . .
H11A H -0.3619 0.0045 -0.4328 0.076 Uiso 1 1 calc R U . . .
H11B H -0.3500 0.0036 -0.2997 0.076 Uiso 1 1 calc R U . . .
H11C H -0.3898 -0.0686 -0.3670 0.076 Uiso 1 1 calc R U . . .
C12 C -0.0048(3) -0.21234(18) -0.4635(3) 0.0591(8) Uani 1 1 d . . . . .
H12A H 0.0864 -0.2211 -0.4530 0.089 Uiso 1 1 calc R U . . .
H12B H -0.0304 -0.2141 -0.5430 0.089 Uiso 1 1 calc R U . . .
H12C H -0.0506 -0.2497 -0.4242 0.089 Uiso 1 1 calc R U . . .
C13 C -0.1151(2) 0.20560(14) -0.0547(2) 0.0326(5) Uani 1 1 d . . . . .
C14 C -0.0256(2) 0.26333(15) -0.0570(2) 0.0346(5) Uani 1 1 d . . . . .
C15 C -0.0110(2) 0.30995(16) 0.0366(2) 0.0388(6) Uani 1 1 d . . . . .
H15 H 0.0467 0.3493 0.0350 0.047 Uiso 1 1 calc R U . . .
C16 C -0.0805(3) 0.29930(16) 0.1326(2) 0.0431(7) Uani 1 1 d . . . . .
C17 C -0.1650(3) 0.24013(17) 0.1327(2) 0.0444(7) Uani 1 1 d . . . . .
H17 H -0.2102 0.2317 0.1973 0.053 Uiso 1 1 calc R U . . .
C18 C -0.1855(2) 0.19247(15) 0.0402(2) 0.0388(6) Uani 1 1 d . . . . .
C19 C -0.2811(3) 0.12947(17) 0.0443(3) 0.0511(7) Uani 1 1 d . . . . .
H19A H -0.3330 0.1277 -0.0258 0.077 Uiso 1 1 calc R U . . .
H19B H -0.3358 0.1372 0.1061 0.077 Uiso 1 1 calc R U . . .
H19C H -0.2353 0.0836 0.0552 0.077 Uiso 1 1 calc R U . . .
C20 C 0.0563(3) 0.27472(17) -0.1572(2) 0.0461(7) Uani 1 1 d . . . . .
H20A H 0.0041 0.2951 -0.2195 0.069 Uiso 1 1 calc R U . . .
H20B H 0.0914 0.2280 -0.1794 0.069 Uiso 1 1 calc R U . . .
H20C H 0.1256 0.3083 -0.1364 0.069 Uiso 1 1 calc R U . . .
C21 C -0.0630(3) 0.35186(19) 0.2321(2) 0.0598(9) Uani 1 1 d . . . . .
H21A H 0.0228 0.3468 0.2664 0.090 Uiso 1 1 calc R U . . .
H21B H -0.1248 0.3403 0.2871 0.090 Uiso 1 1 calc R U . . .
H21C H -0.0761 0.4018 0.2061 0.090 Uiso 1 1 calc R U . . .
C22 C 0.2060(3) 0.13510(16) 0.0930(2) 0.0478(7) Uani 1 1 d . . . . .
H22A H 0.1869 0.1810 0.0527 0.057 Uiso 1 1 calc R U . . .
H22B H 0.2032 0.1451 0.1737 0.057 Uiso 1 1 calc R U . . .
C23 C 0.3421(3) 0.1099(2) 0.0682(3) 0.0788(12) Uani 1 1 d . . . . .
H23A H 0.3590 0.0624 0.1027 0.118 Uiso 1 1 calc R U . . .
H23B H 0.4039 0.1452 0.0988 0.118 Uiso 1 1 calc R U . . .
H23C H 0.3489 0.1061 -0.0124 0.118 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
Zn1 C22 1.965(3) . ?
Zn1 N1 1.974(2) . ?
Zn1 N1 1.976(2) 3 ?
Zn1 Zn1 2.8882(6) 3 ?
N1 C1 1.276(3) . ?
N1 Zn1 1.976(2) 3 ?
N2 C2 1.393(3) . ?
N2 C1 1.396(3) . ?
N2 C4 1.422(3) . ?
N3 C3 1.397(3) . ?
N3 C1 1.401(3) . ?
N3 C13 1.432(3) . ?
C2 C3 1.327(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.398(4) . ?
C4 C9 1.407(4) . ?
C5 C6 1.391(4) . ?
C5 C11 1.506(4) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(4) . ?
C7 C12 1.509(4) . ?
C8 C9 1.379(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.504(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.392(3) . ?
C13 C14 1.397(3) . ?
C14 C15 1.390(3) . ?
C14 C20 1.510(3) . ?
C15 C16 1.391(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 C21 1.512(4) . ?
C17 C18 1.396(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.512(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.528(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C22 Zn1 N1 136.68(11) . . ?
C22 Zn1 N1 133.48(10) . 3 ?
N1 Zn1 N1 86.02(9) . 3 ?
C22 Zn1 Zn1 165.47(10) . 3 ?
N1 Zn1 Zn1 43.04(6) . 3 ?
N1 Zn1 Zn1 42.99(6) 3 3 ?
C1 N1 Zn1 133.53(19) . . ?
C1 N1 Zn1 132.48(18) . 3 ?
Zn1 N1 Zn1 93.98(9) . 3 ?
C2 N2 C1 110.1(2) . . ?
C2 N2 C4 125.8(2) . . ?
C1 N2 C4 123.8(2) . . ?
C3 N3 C1 110.3(2) . . ?
C3 N3 C13 125.1(2) . . ?
C1 N3 C13 124.5(2) . . ?
N1 C1 N2 128.3(3) . . ?
N1 C1 N3 128.4(2) . . ?
N2 C1 N3 103.3(2) . . ?
C3 C2 N2 108.6(2) . . ?
C3 C2 H2 125.7 . . ?
N2 C2 H2 125.7 . . ?
C2 C3 N3 107.6(2) . . ?
C2 C3 H3 126.2 . . ?
N3 C3 H3 126.2 . . ?
C5 C4 C9 121.1(3) . . ?
C5 C4 N2 119.5(3) . . ?
C9 C4 N2 119.5(2) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C11 120.1(3) . . ?
C4 C5 C11 121.7(3) . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C8 C7 C6 118.0(3) . . ?
C8 C7 C12 122.1(3) . . ?
C6 C7 C12 119.9(3) . . ?
C9 C8 C7 122.9(3) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C8 C9 C4 117.7(3) . . ?
C8 C9 C10 120.9(3) . . ?
C4 C9 C10 121.4(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 121.5(2) . . ?
C18 C13 N3 120.3(2) . . ?
C14 C13 N3 118.1(2) . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 C20 120.0(2) . . ?
C13 C14 C20 121.5(2) . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 117.8(3) . . ?
C17 C16 C21 122.1(3) . . ?
C15 C16 C21 120.1(3) . . ?
C16 C17 C18 122.9(2) . . ?
C16 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
C13 C18 C17 117.4(2) . . ?
C13 C18 C19 122.0(2) . . ?
C17 C18 C19 120.6(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 Zn1 113.1(2) . . ?
C23 C22 H22A 109.0 . . ?
Zn1 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
Zn1 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
Zn1 N1 C1 N2 144.9(2) . . . . ?
Zn1 N1 C1 N2 -36.5(4) 3 . . . ?
Zn1 N1 C1 N3 -34.9(4) . . . . ?
Zn1 N1 C1 N3 143.7(2) 3 . . . ?
C2 N2 C1 N1 179.7(3) . . . . ?
C4 N2 C1 N1 -6.5(4) . . . . ?
C2 N2 C1 N3 -0.5(3) . . . . ?
C4 N2 C1 N3 173.4(2) . . . . ?
C3 N3 C1 N1 -179.7(3) . . . . ?
C13 N3 C1 N1 3.9(4) . . . . ?
C3 N3 C1 N2 0.5(3) . . . . ?
C13 N3 C1 N2 -176.0(2) . . . . ?
C1 N2 C2 C3 0.3(3) . . . . ?
C4 N2 C2 C3 -173.4(3) . . . . ?
N2 C2 C3 N3 0.0(3) . . . . ?
C1 N3 C3 C2 -0.3(3) . . . . ?
C13 N3 C3 C2 176.1(2) . . . . ?
C2 N2 C4 C5 -69.1(4) . . . . ?
C1 N2 C4 C5 118.0(3) . . . . ?
C2 N2 C4 C9 110.5(3) . . . . ?
C1 N2 C4 C9 -62.3(4) . . . . ?
C9 C4 C5 C6 2.4(4) . . . . ?
N2 C4 C5 C6 -178.0(2) . . . . ?
C9 C4 C5 C11 -178.5(3) . . . . ?
N2 C4 C5 C11 1.1(4) . . . . ?
C4 C5 C6 C7 1.2(4) . . . . ?
C11 C5 C6 C7 -178.0(3) . . . . ?
C5 C6 C7 C8 -2.9(4) . . . . ?
C5 C6 C7 C12 177.7(3) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C12 C7 C8 C9 -179.5(3) . . . . ?
C7 C8 C9 C4 2.2(4) . . . . ?
C7 C8 C9 C10 -176.6(3) . . . . ?
C5 C4 C9 C8 -4.0(4) . . . . ?
N2 C4 C9 C8 176.4(2) . . . . ?
C5 C4 C9 C10 174.9(3) . . . . ?
N2 C4 C9 C10 -4.7(4) . . . . ?
C3 N3 C13 C18 114.4(3) . . . . ?
C1 N3 C13 C18 -69.7(3) . . . . ?
C3 N3 C13 C14 -64.1(3) . . . . ?
C1 N3 C13 C14 111.8(3) . . . . ?
C18 C13 C14 C15 -2.4(4) . . . . ?
N3 C13 C14 C15 176.1(2) . . . . ?
C18 C13 C14 C20 176.3(2) . . . . ?
N3 C13 C14 C20 -5.2(4) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C20 C14 C15 C16 -177.1(2) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C14 C15 C16 C21 -179.2(3) . . . . ?
C15 C16 C17 C18 -1.7(4) . . . . ?
C21 C16 C17 C18 177.9(3) . . . . ?
C14 C13 C18 C17 1.1(4) . . . . ?
N3 C13 C18 C17 -177.3(2) . . . . ?
C14 C13 C18 C19 -179.1(2) . . . . ?
N3 C13 C18 C19 2.4(4) . . . . ?
C16 C17 C18 C13 1.0(4) . . . . ?
C16 C17 C18 C19 -178.8(2) . . . . ?

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_9138
_database_code_depnum_ccdc_archive 'CCDC 1945343'
loop_
_audit_author_name
_audit_author_address
'Tarun Kanti Panda'
;IIT Hyderabad
India
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2019-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Cl N S'
_chemical_formula_sum            'C8 H12 Cl N S'
_chemical_formula_weight         189.70

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'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 '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'

_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                   4.3870(3)
_cell_length_b                   5.6906(3)
_cell_length_c                   19.2566(14)
_cell_angle_alpha                86.981(5)
_cell_angle_beta                 85.060(6)
_cell_angle_gamma                85.181(5)
_cell_volume                     476.76(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1476
_cell_measurement_theta_min      4.6350
_cell_measurement_theta_max      69.7150

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    5.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.25201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3213
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         69.941
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1786
_reflns_number_gt                1563
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_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)+(0.0849P)²+0.0219P] 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         1786
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 -0.0830(2) 0.52321(16) 0.40929(4) 0.0773(3) Uani 1 1 d . . . . .
N1 N 0.4138(5) 0.7282(3) 0.06649(9) 0.0454(5) Uani 1 1 d . . . . .
H1A H 0.320070 0.594803 0.070513 0.068 Uiso 1 1 calc R U . . .
H1B H 0.542072 0.727968 0.028076 0.068 Uiso 1 1 calc R U . . .
H1C H 0.274516 0.850660 0.063800 0.068 Uiso 1 1 calc R U . . .
C2 C 0.4052(5) 0.6946(4) 0.19624(11) 0.0439(5) Uani 1 1 d . . . . .
C1 C 0.5887(5) 0.7467(4) 0.12837(12) 0.0487(5) Uani 1 1 d . . . . .
H1AA H 0.655402 0.904980 0.128438 0.058 Uiso 1 1 calc R U . . .
H1BB H 0.770676 0.637345 0.124743 0.058 Uiso 1 1 calc R U . . .
C5 C 0.0917(6) 0.6013(5) 0.32611(12) 0.0531(6) Uani 1 1 d . . . . .
C7 C 0.1964(6) 0.8635(4) 0.22669(12) 0.0493(5) Uani 1 1 d . . . . .
H7 H 0.161198 1.009625 0.203596 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4511(7) 0.4777(5) 0.23111(13) 0.0560(6) Uani 1 1 d . . . . .
H3 H 0.586874 0.361024 0.211111 0.067 Uiso 1 1 calc R U . . .
C6 C 0.0395(6) 0.8181(5) 0.29096(12) 0.0542(6) Uani 1 1 d . . . . .
H6 H -0.100711 0.932849 0.310476 0.065 Uiso 1 1 calc R U . . .
C4 C 0.2969(8) 0.4327(5) 0.29545(14) 0.0615(7) Uani 1 1 d . . . . .
H4 H 0.332091 0.286338 0.318448 0.074 Uiso 1 1 calc R U . . .
C8 C -0.3068(9) 0.7843(7) 0.43496(17) 0.0884(11) Uani 1 1 d . . . . .
H8A H -0.175309 0.910179 0.436536 0.133 Uiso 1 1 calc R U . . .
H8B H -0.409812 0.756555 0.480321 0.133 Uiso 1 1 calc R U . . .
H8C H -0.455919 0.826939 0.401891 0.133 Uiso 1 1 calc R U . . .
Cl1 Cl 0.08111(12) 0.24368(9) 0.06418(3) 0.0465(2) Uani 1 1 d . . . . .


_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 C5 1.767(2) . ?
S1 C8 1.779(4) . ?
N1 C1 1.485(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 C3 1.382(3) . ?
C2 C7 1.387(3) . ?
C2 C1 1.504(3) . ?
C1 H1AA 0.9700 . ?
C1 H1BB 0.9700 . ?
C5 C4 1.380(4) . ?
C5 C6 1.387(4) . ?
C7 C6 1.386(3) . ?
C7 H7 0.9300 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C5 S1 C8 104.19(16) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 C2 C7 118.4(2) . . ?
C3 C2 C1 120.0(2) . . ?
C7 C2 C1 121.5(2) . . ?
N1 C1 C2 113.04(18) . . ?
N1 C1 H1AA 109.0 . . ?
C2 C1 H1AA 109.0 . . ?
N1 C1 H1BB 109.0 . . ?
C2 C1 H1BB 109.0 . . ?
H1AA C1 H1BB 107.8 . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 S1 116.4(2) . . ?
C6 C5 S1 124.7(2) . . ?
C6 C7 C2 121.1(2) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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 C2 C1 N1 101.9(3) . . . . ?
C7 C2 C1 N1 -80.7(3) . . . . ?
C8 S1 C5 C4 176.0(2) . . . . ?
C8 S1 C5 C6 -3.1(3) . . . . ?
C3 C2 C7 C6 0.8(4) . . . . ?
C1 C2 C7 C6 -176.7(2) . . . . ?
C7 C2 C3 C4 -1.3(4) . . . . ?
C1 C2 C3 C4 176.2(2) . . . . ?
C2 C7 C6 C5 0.4(4) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
S1 C5 C6 C7 178.0(2) . . . . ?
C6 C5 C4 C3 0.6(4) . . . . ?
S1 C5 C4 C3 -178.6(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.063

