# 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. 
# 
#######################################################################

data_ber1871
_database_code_depnum_ccdc_archive 'CCDC 981321'
_audit_update_record             
;
2014-01-13 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 Cl0 N O4 S Zn0'
_chemical_formula_weight         285.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   5.51320(10)
_cell_length_b                   11.8110(2)
_cell_length_c                   21.7712(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1417.66(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    2.127
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8482
_exptl_absorpt_correction_T_max  0.8482
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18602
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         70.98
_reflns_number_total             2718
_reflns_number_gt                2653
_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)+(0.0532P)²+0.4671P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(16)
_refine_ls_number_reflns         2718
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56360(7) 0.50878(3) 0.648606(18) 0.02048(12) Uani 1 1 d . . .
O1 O 0.3048(2) 0.49689(12) 0.65065(6) 0.0267(3) Uani 1 1 d . . .
O2 O 0.7123(3) 0.45778(12) 0.69445(6) 0.0285(3) Uani 1 1 d . . .
O3 O 0.7762(2) 0.73361(12) 0.54194(6) 0.0263(3) Uani 1 1 d . . .
O4 O 1.1611(2) 0.73334(12) 0.57518(5) 0.0243(3) Uani 1 1 d . . .
H4 H 1.1915 0.7495 0.5384 0.036 Uiso 1 1 calc R . .
N1 N 0.6102(3) 0.64538(12) 0.65057(6) 0.0197(3) Uani 1 1 d . . .
H1A H 0.4866 0.6923 0.6534 0.024 Uiso 1 1 calc R . .
C1 C 0.6647(3) 0.45991(15) 0.57595(8) 0.0208(4) Uani 1 1 d . . .
C2 C 0.5331(3) 0.48826(15) 0.52355(9) 0.0251(4) Uani 1 1 d . . .
H2 H 0.3875 0.5309 0.5268 0.030 Uiso 1 1 calc R . .
C3 C 0.6173(4) 0.45352(16) 0.46649(9) 0.0280(4) Uani 1 1 d . . .
H3 H 0.5283 0.4727 0.4306 0.034 Uiso 1 1 calc R . .
C4 C 0.8303(4) 0.39100(16) 0.46111(9) 0.0257(4) Uani 1 1 d . . .
C5 C 0.9190(4) 0.35146(19) 0.39900(9) 0.0358(5) Uani 1 1 d . . .
H5A H 0.8460 0.2779 0.3893 0.054 Uiso 1 1 calc R . .
H5B H 1.0960 0.3440 0.3998 0.054 Uiso 1 1 calc R . .
H5C H 0.8724 0.4068 0.3676 0.054 Uiso 1 1 calc R . .
C6 C 0.9574(4) 0.36342(16) 0.51433(9) 0.0279(4) Uani 1 1 d . . .
H6 H 1.1020 0.3201 0.5113 0.034 Uiso 1 1 calc R . .
C7 C 0.8770(3) 0.39792(15) 0.57165(9) 0.0248(4) Uani 1 1 d . . .
H7 H 0.9665 0.3793 0.6075 0.030 Uiso 1 1 calc R . .
C8 C 0.8561(3) 0.68913(14) 0.64770(8) 0.0192(3) Uani 1 1 d . . .
H8 H 0.9698 0.6291 0.6625 0.023 Uiso 1 1 calc R . .
C9 C 0.9244(3) 0.72017(14) 0.58219(7) 0.0191(3) Uani 1 1 d . . .
C10 C 0.8843(3) 0.79505(16) 0.68958(8) 0.0242(4) Uani 1 1 d . . .
H10 H 1.0493 0.8277 0.6825 0.029 Uiso 1 1 calc R . .
C11 C 0.6944(4) 0.88681(16) 0.67352(10) 0.0295(4) Uani 1 1 d . . .
H11A H 0.5319 0.8592 0.6839 0.044 Uiso 1 1 calc R . .
H11B H 0.7022 0.9036 0.6295 0.044 Uiso 1 1 calc R . .
H11C H 0.7289 0.9558 0.6970 0.044 Uiso 1 1 calc R . .
C12 C 0.8647(3) 0.76190(18) 0.75739(8) 0.0278(4) Uani 1 1 d . . .
H12A H 0.8659 0.8315 0.7827 0.033 Uiso 1 1 calc R . .
H12B H 0.7076 0.7233 0.7642 0.033 Uiso 1 1 calc R . .
C13 C 1.0682(4) 0.68472(19) 0.77868(9) 0.0365(5) Uani 1 1 d . . .
H13A H 1.0517 0.6106 0.7589 0.055 Uiso 1 1 calc R . .
H13B H 1.0594 0.6755 0.8234 0.055 Uiso 1 1 calc R . .
H13C H 1.2248 0.7182 0.7676 0.055 Uiso 1 1 calc R . .


_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 O2 1.4252(14) . ?
S1 O1 1.4344(13) . ?
S1 N1 1.6343(14) . ?
S1 C1 1.7736(18) . ?
O3 C9 1.209(2) . ?
O4 C9 1.323(2) . ?
O4 H4 0.8400 . ?
N1 C8 1.452(2) . ?
N1 H1A 0.8800 . ?
C1 C7 1.384(3) . ?
C1 C2 1.393(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C6 1.392(3) . ?
C4 C5 1.512(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.520(2) . ?
C8 C10 1.556(2) . ?
C8 H8 1.0000 . ?
C10 C12 1.531(2) . ?
C10 C11 1.547(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.518(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
O2 S1 O1 120.61(8) . . ?
O2 S1 N1 107.97(8) . . ?
O1 S1 N1 104.60(8) . . ?
O2 S1 C1 107.83(9) . . ?
O1 S1 C1 107.96(8) . . ?
N1 S1 C1 107.17(8) . . ?
C9 O4 H4 109.5 . . ?
C8 N1 S1 119.78(12) . . ?
C8 N1 H1A 120.1 . . ?
S1 N1 H1A 120.1 . . ?
C7 C1 C2 120.82(17) . . ?
C7 C1 S1 119.88(14) . . ?
C2 C1 S1 119.25(14) . . ?
C3 C2 C1 119.20(17) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.93(18) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C6 C4 C3 118.58(18) . . ?
C6 C4 C5 120.62(18) . . ?
C3 C4 C5 120.78(19) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.32(18) . . ?
C7 C6 H6 119.3 . . ?
C4 C6 H6 119.3 . . ?
C1 C7 C6 119.14(17) . . ?
C1 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N1 C8 C9 110.95(14) . . ?
N1 C8 C10 110.73(14) . . ?
C9 C8 C10 109.34(14) . . ?
N1 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C10 C8 H8 108.6 . . ?
O3 C9 O4 124.60(16) . . ?
O3 C9 C8 122.97(17) . . ?
O4 C9 C8 112.40(14) . . ?
C12 C10 C11 110.46(16) . . ?
C12 C10 C8 110.63(15) . . ?
C11 C10 C8 111.32(15) . . ?
C12 C10 H10 108.1 . . ?
C11 C10 H10 108.1 . . ?
C8 C10 H10 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 113.32(16) . . ?
C13 C12 H12A 108.9 . . ?
C10 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C10 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O2 S1 N1 C8 51.85(14) . . . . ?
O1 S1 N1 C8 -178.53(12) . . . . ?
C1 S1 N1 C8 -64.07(14) . . . . ?
O2 S1 C1 C7 -8.88(17) . . . . ?
O1 S1 C1 C7 -140.68(15) . . . . ?
N1 S1 C1 C7 107.14(15) . . . . ?
O2 S1 C1 C2 173.49(14) . . . . ?
O1 S1 C1 C2 41.69(17) . . . . ?
N1 S1 C1 C2 -70.49(16) . . . . ?
C7 C1 C2 C3 0.0(3) . . . . ?
S1 C1 C2 C3 177.63(14) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C6 0.3(3) . . . . ?
C2 C3 C4 C5 178.86(18) . . . . ?
C3 C4 C6 C7 -0.7(3) . . . . ?
C5 C4 C6 C7 -179.26(18) . . . . ?
C2 C1 C7 C6 -0.4(3) . . . . ?
S1 C1 C7 C6 -178.01(14) . . . . ?
C4 C6 C7 C1 0.8(3) . . . . ?
S1 N1 C8 C9 95.31(15) . . . . ?
S1 N1 C8 C10 -143.09(12) . . . . ?
N1 C8 C9 O3 17.3(2) . . . . ?
C10 C8 C9 O3 -105.12(19) . . . . ?
N1 C8 C9 O4 -164.34(15) . . . . ?
C10 C8 C9 O4 73.25(18) . . . . ?
N1 C8 C10 C12 68.35(19) . . . . ?
C9 C8 C10 C12 -169.10(15) . . . . ?
N1 C8 C10 C11 -54.86(19) . . . . ?
C9 C8 C10 C11 67.68(19) . . . . ?
C11 C10 C12 C13 -171.78(17) . . . . ?
C8 C10 C12 C13 64.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        70.98
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.049
