# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_chiru
_database_code_depnum_ccdc_archive 'CCDC 1425924'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H26 N2 O4 S2 Zn'
_chemical_formula_sum            'C32 H26 N2 O4 S2 Zn'
_chemical_formula_weight         632.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   25.7165(8)
_cell_length_b                   7.5044(2)
_cell_length_c                   16.1890(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.067(2)
_cell_angle_gamma                90.00
_cell_volume                     2874.47(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23176
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.01
_reflns_number_total             3474
_reflns_number_gt                2593
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3448
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_restrained_S_all      0.857
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.00909(8) 0.7510(2) 0.38313(13) 0.0402(4) Uani 1 1 d . . .
Zn1 Zn 0.0000 0.71844(5) 0.2500 0.03950(15) Uani 1 2 d S . .
O333 O 0.06624(7) 0.5610(2) 0.28978(11) 0.0488(4) Uani 1 1 d . . .
O111 O 0.20881(11) 0.3567(5) 0.29158(18) 0.1113(10) Uani 1 1 d . . .
C00 C -0.07945(9) 0.9160(3) 0.33577(15) 0.0445(5) Uani 1 1 d . . .
C01 C 0.16187(10) 0.4984(4) 0.37364(18) 0.0529(6) Uani 1 1 d . . .
C03 C -0.03878(9) 0.8070(3) 0.39972(15) 0.0414(5) Uani 1 1 d . . .
C04 C 0.10917(9) 0.5728(3) 0.36618(15) 0.0433(5) Uani 1 1 d . . .
C31E C 0.16688(14) 0.4274(5) 0.2927(2) 0.0758(9) Uani 1 1 d . . .
S1 S -0.07092(2) 0.98838(9) 0.23754(4) 0.04684(18) Uani 1 1 d . . .
C41E C 0.25655(11) 0.5652(5) 0.6210(2) 0.0840(10) Uani 1 1 d . . .
H41A H 0.2558 0.4580 0.6528 0.126 Uiso 1 1 calc R . .
H41B H 0.2556 0.6667 0.6566 0.126 Uiso 1 1 calc R . .
H41C H 0.2905 0.5682 0.6098 0.126 Uiso 1 1 calc R . .
C42E C -0.09858(12) 0.7919(4) 0.4823(2) 0.0602(7) Uani 1 1 d . . .
H42E H -0.1046 0.7531 0.5324 0.072 Uiso 1 1 calc R . .
C43E C 0.20569(10) 0.5698(4) 0.53268(18) 0.0585(7) Uani 1 1 d . . .
C44E C 0.20782(10) 0.4984(4) 0.4558(2) 0.0622(7) Uani 1 1 d . . .
H44E H 0.2415 0.4477 0.4590 0.075 Uiso 1 1 calc R . .
C45E C -0.13855(11) 0.8944(4) 0.4186(2) 0.0633(7) Uani 1 1 d . . .
H45E H -0.1722 0.9212 0.4245 0.076 Uiso 1 1 calc R . .
C46E C -0.12902(10) 0.9579(4) 0.34599(19) 0.0554(6) Uani 1 1 d . . .
H46E H -0.1560 1.0292 0.3036 0.066 Uiso 1 1 calc R . .
C47E C -0.01781(11) 1.1637(4) 0.27772(18) 0.0523(6) Uani 1 1 d . . .
H47A H -0.0362 1.2785 0.2727 0.063 Uiso 1 1 calc R . .
H47B H 0.0060 1.1436 0.3404 0.063 Uiso 1 1 calc R . .
C48E C 0.15530(10) 0.6442(4) 0.52589(17) 0.0529(6) Uani 1 1 d . . .
H48E H 0.1530 0.6931 0.5771 0.063 Uiso 1 1 calc R . .
C49E C -0.04911(11) 0.7460(3) 0.47233(19) 0.0512(6) Uani 1 1 d . . .
H49E H -0.0227 0.6735 0.5149 0.061 Uiso 1 1 calc R . .
C1 C 0.10687(9) 0.6498(3) 0.44464(15) 0.0428(5) Uani 1 1 d . . .
C444 C 0.05667(10) 0.7257(3) 0.44950(16) 0.0422(5) Uani 1 1 d . . .
H212 H 0.1269(13) 0.439(5) 0.221(2) 0.095(11) Uiso 1 1 d . . .
H444 H 0.0617(11) 0.759(3) 0.5059(19) 0.045(7) Uiso 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
N2 C444 1.287(3) . ?
N2 C03 1.423(3) . ?
N2 Zn1 2.089(2) . ?
Zn1 O333 1.9628(16) 2 ?
Zn1 O333 1.9628(16) . ?
Zn1 N2 2.089(2) 2 ?
Zn1 S1 2.6800(7) 2 ?
Zn1 S1 2.6801(7) . ?
O333 C04 1.299(3) . ?
O111 C31E 1.209(3) . ?
C00 C46E 1.385(3) . ?
C00 C03 1.409(3) . ?
C00 S1 1.773(2) . ?
C01 C44E 1.391(4) . ?
C01 C04 1.427(3) . ?
C01 C31E 1.466(4) . ?
C03 C49E 1.381(4) . ?
C04 C1 1.417(3) . ?
C31E H212 1.22(3) . ?
S1 C47E 1.823(3) . ?
C41E C43E 1.514(4) . ?
C41E H41A 0.9600 . ?
C41E H41B 0.9600 . ?
C41E H41C 0.9600 . ?
C42E C45E 1.372(4) . ?
C42E C49E 1.387(4) . ?
C42E H42E 0.9300 . ?
C43E C44E 1.375(4) . ?
C43E C48E 1.376(3) . ?
C44E H44E 0.9300 . ?
C45E C46E 1.377(4) . ?
C45E H45E 0.9300 . ?
C46E H46E 0.9300 . ?
C47E C47E 1.513(5) 2 ?
C47E H47A 0.9700 . ?
C47E H47B 0.9700 . ?
C48E C1 1.414(3) . ?
C48E H48E 0.9300 . ?
C49E H49E 0.9300 . ?
C1 C444 1.441(3) . ?
C444 H444 0.91(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
C444 N2 C03 119.7(2) . . ?
C444 N2 Zn1 121.96(17) . . ?
C03 N2 Zn1 118.30(14) . . ?
O333 Zn1 O333 105.98(10) 2 . ?
O333 Zn1 N2 98.09(7) 2 . ?
O333 Zn1 N2 90.00(7) . . ?
O333 Zn1 N2 90.00(7) 2 2 ?
O333 Zn1 N2 98.10(7) . 2 ?
N2 Zn1 N2 166.57(10) . 2 ?
O333 Zn1 S1 163.18(5) 2 2 ?
O333 Zn1 S1 87.29(5) . 2 ?
N2 Zn1 S1 92.07(5) . 2 ?
N2 Zn1 S1 77.70(5) 2 2 ?
O333 Zn1 S1 87.29(5) 2 . ?
O333 Zn1 S1 163.18(5) . . ?
N2 Zn1 S1 77.70(5) . . ?
N2 Zn1 S1 92.08(5) 2 . ?
S1 Zn1 S1 81.80(3) 2 . ?
C04 O333 Zn1 125.18(15) . . ?
C46E C00 C03 119.8(2) . . ?
C46E C00 S1 118.73(19) . . ?
C03 C00 S1 121.31(18) . . ?
C44E C01 C04 120.2(2) . . ?
C44E C01 C31E 121.1(3) . . ?
C04 C01 C31E 118.7(2) . . ?
C49E C03 C00 118.9(2) . . ?
C49E C03 N2 122.1(2) . . ?
C00 C03 N2 118.7(2) . . ?
O333 C04 C1 124.3(2) . . ?
O333 C04 C01 118.6(2) . . ?
C1 C04 C01 117.1(2) . . ?
O111 C31E C01 124.4(3) . . ?
O111 C31E H212 116.4(16) . . ?
C01 C31E H212 119.2(16) . . ?
C00 S1 C47E 103.87(12) . . ?
C00 S1 Zn1 91.18(8) . . ?
C47E S1 Zn1 97.24(9) . . ?
C43E C41E H41A 109.5 . . ?
C43E C41E H41B 109.5 . . ?
H41A C41E H41B 109.5 . . ?
C43E C41E H41C 109.5 . . ?
H41A C41E H41C 109.5 . . ?
H41B C41E H41C 109.5 . . ?
C45E C42E C49E 120.2(3) . . ?
C45E C42E H42E 119.9 . . ?
C49E C42E H42E 119.9 . . ?
C44E C43E C48E 117.1(2) . . ?
C44E C43E C41E 121.4(3) . . ?
C48E C43E C41E 121.5(3) . . ?
C43E C44E C01 123.1(2) . . ?
C43E C44E H44E 118.5 . . ?
C01 C44E H44E 118.5 . . ?
C42E C45E C46E 120.3(2) . . ?
C42E C45E H45E 119.9 . . ?
C46E C45E H45E 119.9 . . ?
C45E C46E C00 120.2(2) . . ?
C45E C46E H46E 119.9 . . ?
C00 C46E H46E 119.9 . . ?
C47E C47E S1 109.36(18) 2 . ?
C47E C47E H47A 109.8 2 . ?
S1 C47E H47A 109.8 . . ?
C47E C47E H47B 109.8 2 . ?
S1 C47E H47B 109.8 . . ?
H47A C47E H47B 108.3 . . ?
C43E C48E C1 123.0(3) . . ?
C43E C48E H48E 118.5 . . ?
C1 C48E H48E 118.5 . . ?
C03 C49E C42E 120.5(2) . . ?
C03 C49E H49E 119.7 . . ?
C42E C49E H49E 119.7 . . ?
C48E C1 C04 119.4(2) . . ?
C48E C1 C444 116.2(2) . . ?
C04 C1 C444 124.2(2) . . ?
N2 C444 C1 126.3(2) . . ?
N2 C444 H444 121.1(17) . . ?
C1 C444 H444 112.7(17) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.01
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.055
