# 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_a
_database_code_depnum_ccdc_archive 'CCDC 933691'
_audit_update_record             
;
2013-04-11 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;
#TrackingRef 'A.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 Cl N O5 Si'
_chemical_formula_sum            'C20 H22 Cl N O5 Si'
_chemical_formula_weight         419.93

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'
Si Si 0.0817 0.0704 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   7.145(5)
_cell_length_b                   35.461(16)
_cell_length_c                   10.506(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 133.00(11)
_cell_angle_gamma                90.00
_cell_volume                     1947(2)
_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       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16740
_diffrn_reflns_av_R_equivalents  0.1717
_diffrn_reflns_av_sigmaI/netI    0.1385
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3434
_reflns_number_gt                2288
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0746P)²+72.7646P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3434
_refine_ls_number_parameters     254
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.2226
_refine_ls_R_factor_gt           0.1825
_refine_ls_wR_factor_ref         0.4339
_refine_ls_wR_factor_gt          0.4127
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.100
_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
Cl1 Cl 0.7661(7) 0.63646(11) 0.6511(5) 0.0336(10) Uani 1 1 d . . .
Si1 Si 0.3363(8) 0.30406(12) -0.0164(5) 0.0296(11) Uani 1 1 d . . .
O1 O 1.0456(19) 0.5683(3) 0.7991(11) 0.035(3) Uani 1 1 d . . .
O2 O 0.3955(17) 0.4830(3) 0.2178(12) 0.032(2) Uani 1 1 d . . .
O3 O 0.3548(18) 0.2585(3) -0.0081(12) 0.033(2) Uani 1 1 d . . .
O4 O 0.356(2) 0.3220(3) -0.1488(13) 0.037(3) Uani 1 1 d . . .
O5 O 0.057(2) 0.3136(3) -0.0900(15) 0.041(3) Uani 1 1 d . . .
N1 N 0.7012(19) 0.4242(3) 0.3800(13) 0.021(2) Uani 1 1 d U . .
H1 H 0.5682 0.4341 0.2795 0.025 Uiso 1 1 calc R . .
C1 C 0.593(2) 0.6047(4) 0.4794(16) 0.022(3) Uani 1 1 d U . .
C2 C 0.374(3) 0.6195(4) 0.3157(19) 0.033(3) Uani 1 1 d U . .
H2 H 0.3278 0.6453 0.3037 0.039 Uiso 1 1 calc R . .
C3 C 0.233(3) 0.5957(4) 0.1758(18) 0.031(3) Uani 1 1 d U . .
H3 H 0.0907 0.6057 0.0646 0.037 Uiso 1 1 calc R . .
C4 C 0.286(2) 0.5580(4) 0.1893(16) 0.023(3) Uani 1 1 d U . .
H4 H 0.1766 0.5422 0.0900 0.028 Uiso 1 1 calc R . .
C5 C 0.501(2) 0.5429(4) 0.3479(15) 0.018(3) Uani 1 1 d U . .
C6 C 0.549(2) 0.5023(4) 0.3537(16) 0.019(3) Uani 1 1 d U . .
C7 C 0.782(2) 0.4857(4) 0.5137(15) 0.017(3) Uani 1 1 d U . .
C8 C 0.849(2) 0.4473(4) 0.5269(15) 0.019(3) Uani 1 1 d U . .
C9 C 1.071(3) 0.4320(4) 0.6868(18) 0.027(3) Uani 1 1 d U . .
H9 H 1.1170 0.4063 0.6954 0.033 Uiso 1 1 calc R . .
C10 C 1.220(2) 0.4555(4) 0.8305(16) 0.021(3) Uani 1 1 d U . .
H10 H 1.3681 0.4452 0.9385 0.025 Uiso 1 1 calc R . .
C11 C 1.166(3) 0.4930(4) 0.8258(17) 0.027(3) Uani 1 1 d U . .
H11 H 1.2734 0.5079 0.9283 0.032 Uiso 1 1 calc R . .
C12 C 0.947(2) 0.5089(4) 0.6665(15) 0.018(3) Uani 1 1 d U . .
C13 C 0.898(2) 0.5491(4) 0.6657(15) 0.020(3) Uani 1 1 d U . .
C14 C 0.659(2) 0.5664(4) 0.4974(15) 0.020(3) Uani 1 1 d U . .
C15 C 0.754(3) 0.3856(4) 0.3844(16) 0.026(3) Uani 1 1 d U . .
H15A H 0.7403 0.3717 0.4595 0.031 Uiso 1 1 calc R . .
H15B H 0.9310 0.3826 0.4341 0.031 Uiso 1 1 calc R . .
C16 C 0.563(3) 0.3691(4) 0.1986(19) 0.033(3) Uani 1 1 d U . .
H16A H 0.3867 0.3755 0.1437 0.039 Uiso 1 1 calc R . .
H16B H 0.5933 0.3809 0.1285 0.039 Uiso 1 1 calc R . .
C17 C 0.587(3) 0.3264(4) 0.1968(17) 0.028(3) Uani 1 1 d U . .
H17A H 0.5829 0.3151 0.2812 0.033 Uiso 1 1 calc R . .
H17B H 0.7555 0.3204 0.2370 0.033 Uiso 1 1 calc R . .
C18 C 0.573(3) 0.2387(5) 0.038(2) 0.046(4) Uani 1 1 d U . .
H18A H 0.5504 0.2114 0.0378 0.070 Uiso 1 1 calc R . .
H18B H 0.7308 0.2466 0.1539 0.070 Uiso 1 1 calc R . .
H18C H 0.5853 0.2447 -0.0475 0.070 Uiso 1 1 calc R . .
C19 C 0.202(3) 0.3087(5) -0.323(2) 0.045(4) Uani 1 1 d U . .
H19A H 0.2422 0.3232 -0.3817 0.068 Uiso 1 1 calc R . .
H19B H 0.0211 0.3119 -0.3861 0.068 Uiso 1 1 calc R . .
H19C H 0.2387 0.2820 -0.3215 0.068 Uiso 1 1 calc R . .
C20 C -0.040(3) 0.2974(5) -0.018(2) 0.038(4) Uani 1 1 d U . .
H20A H -0.2132 0.3067 -0.0829 0.057 Uiso 1 1 calc R . .
H20B H 0.0720 0.3045 0.1043 0.057 Uiso 1 1 calc R . .
H20C H -0.0434 0.2699 -0.0280 0.057 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
Cl1 C1 1.736(13) . ?
Si1 O5 1.612(11) . ?
Si1 O3 1.618(11) . ?
Si1 O4 1.621(10) . ?
Si1 C17 1.838(14) . ?
O1 C13 1.235(15) . ?
O2 C6 1.253(16) . ?
O3 C18 1.463(19) . ?
O4 C19 1.429(19) . ?
O5 C20 1.441(17) . ?
N1 C8 1.395(16) . ?
N1 C15 1.412(17) . ?
N1 H1 0.8800 . ?
C1 C14 1.404(19) . ?
C1 C2 1.42(2) . ?
C2 C3 1.37(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(17) . ?
C4 H4 0.9500 . ?
C5 C14 1.421(17) . ?
C5 C6 1.473(18) . ?
C6 C7 1.457(17) . ?
C7 C12 1.436(17) . ?
C7 C8 1.420(18) . ?
C8 C9 1.414(19) . ?
C9 C10 1.385(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.412(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.466(19) . ?
C13 C14 1.517(17) . ?
C15 C16 1.543(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.53(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O5 Si1 O3 105.3(6) . . ?
O5 Si1 O4 108.1(6) . . ?
O3 Si1 O4 112.8(5) . . ?
O5 Si1 C17 110.6(6) . . ?
O3 Si1 C17 112.8(6) . . ?
O4 Si1 C17 107.1(6) . . ?
C18 O3 Si1 121.8(10) . . ?
C19 O4 Si1 122.1(10) . . ?
C20 O5 Si1 122.9(10) . . ?
C8 N1 C15 123.4(11) . . ?
C8 N1 H1 118.3 . . ?
C15 N1 H1 118.3 . . ?
C14 C1 C2 120.9(12) . . ?
C14 C1 Cl1 123.5(10) . . ?
C2 C1 Cl1 115.6(11) . . ?
C3 C2 C1 118.0(14) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 122.8(14) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 120.1(12) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C14 119.6(12) . . ?
C4 C5 C6 117.5(11) . . ?
C14 C5 C6 122.8(11) . . ?
O2 C6 C7 121.2(12) . . ?
O2 C6 C5 119.2(11) . . ?
C7 C6 C5 119.4(11) . . ?
C12 C7 C6 118.7(11) . . ?
C12 C7 C8 118.3(11) . . ?
C6 C7 C8 122.9(11) . . ?
N1 C8 C9 118.6(12) . . ?
N1 C8 C7 120.4(11) . . ?
C9 C8 C7 121.0(11) . . ?
C10 C9 C8 118.0(13) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 123.7(12) . . ?
C9 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 119.0(12) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C7 119.9(12) . . ?
C11 C12 C13 117.5(11) . . ?
C7 C12 C13 122.6(11) . . ?
O1 C13 C12 121.0(11) . . ?
O1 C13 C14 120.6(12) . . ?
C12 C13 C14 118.3(11) . . ?
C1 C14 C5 118.5(11) . . ?
C1 C14 C13 123.7(11) . . ?
C5 C14 C13 117.7(11) . . ?
N1 C15 C16 109.8(11) . . ?
N1 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
N1 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 112.4(12) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 Si1 114.7(10) . . ?
C16 C17 H17A 108.6 . . ?
Si1 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
Si1 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O5 Si1 O3 C18 174.4(10) . . . . ?
O4 Si1 O3 C18 56.7(12) . . . . ?
C17 Si1 O3 C18 -64.9(12) . . . . ?
O5 Si1 O4 C19 -66.0(12) . . . . ?
O3 Si1 O4 C19 50.0(13) . . . . ?
C17 Si1 O4 C19 174.7(11) . . . . ?
O3 Si1 O5 C20 50.0(12) . . . . ?
O4 Si1 O5 C20 170.8(11) . . . . ?
C17 Si1 O5 C20 -72.2(13) . . . . ?
C14 C1 C2 C3 -1.1(19) . . . . ?
Cl1 C1 C2 C3 179.6(10) . . . . ?
C1 C2 C3 C4 3(2) . . . . ?
C2 C3 C4 C5 -4(2) . . . . ?
C3 C4 C5 C14 2.3(18) . . . . ?
C3 C4 C5 C6 -179.8(11) . . . . ?
C4 C5 C6 O2 -0.4(16) . . . . ?
C14 C5 C6 O2 177.3(11) . . . . ?
C4 C5 C6 C7 175.4(11) . . . . ?
C14 C5 C6 C7 -6.8(16) . . . . ?
O2 C6 C7 C12 -178.5(11) . . . . ?
C5 C6 C7 C12 5.8(16) . . . . ?
O2 C6 C7 C8 -0.5(17) . . . . ?
C5 C6 C7 C8 -176.3(10) . . . . ?
C15 N1 C8 C9 3.6(17) . . . . ?
C15 N1 C8 C7 -178.8(11) . . . . ?
C12 C7 C8 N1 -176.8(10) . . . . ?
C6 C7 C8 N1 5.3(17) . . . . ?
C12 C7 C8 C9 0.7(16) . . . . ?
C6 C7 C8 C9 -177.2(11) . . . . ?
N1 C8 C9 C10 178.2(11) . . . . ?
C7 C8 C9 C10 0.7(17) . . . . ?
C8 C9 C10 C11 -0.9(19) . . . . ?
C9 C10 C11 C12 -0.3(19) . . . . ?
C10 C11 C12 C7 1.7(18) . . . . ?
C10 C11 C12 C13 -178.7(11) . . . . ?
C6 C7 C12 C11 176.1(11) . . . . ?
C8 C7 C12 C11 -1.9(17) . . . . ?
C6 C7 C12 C13 -3.4(16) . . . . ?
C8 C7 C12 C13 178.6(10) . . . . ?
C11 C12 C13 O1 1.2(17) . . . . ?
C7 C12 C13 O1 -179.3(11) . . . . ?
C11 C12 C13 C14 -177.9(11) . . . . ?
C7 C12 C13 C14 1.6(16) . . . . ?
C2 C1 C14 C5 -0.2(17) . . . . ?
Cl1 C1 C14 C5 179.0(9) . . . . ?
C2 C1 C14 C13 176.6(11) . . . . ?
Cl1 C1 C14 C13 -4.2(16) . . . . ?
C4 C5 C14 C1 -0.4(17) . . . . ?
C6 C5 C14 C1 -178.1(10) . . . . ?
C4 C5 C14 C13 -177.4(11) . . . . ?
C6 C5 C14 C13 4.9(16) . . . . ?
O1 C13 C14 C1 1.8(18) . . . . ?
C12 C13 C14 C1 -179.1(11) . . . . ?
O1 C13 C14 C5 178.6(11) . . . . ?
C12 C13 C14 C5 -2.3(15) . . . . ?
C8 N1 C15 C16 -176.9(11) . . . . ?
N1 C15 C16 C17 -172.3(11) . . . . ?
C15 C16 C17 Si1 171.9(9) . . . . ?
O5 Si1 C17 C16 -57.1(11) . . . . ?
O3 Si1 C17 C16 -174.8(9) . . . . ?
O4 Si1 C17 C16 60.5(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.164


####################################################################### 
# 
# 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_f:\solution\d62\khd62
_database_code_depnum_ccdc_archive 'CCDC 1409263'
_audit_update_record             
;
2015-06-27 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H16 Cl2 N2 O6 S1'
_chemical_formula_weight         579.40

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pcnb

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

_cell_length_a                   10.6317(8)
_cell_length_b                   14.5110(10)
_cell_length_c                   16.1526(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2492.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    11048
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      29.19

_exptl_crystal_description       Needle
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS IIT'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11048
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         29.19
_reflns_number_total             3355
_reflns_number_gt                1795
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0849P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3355
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.003
_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
C1 C 0.5775(2) 0.0104(2) 0.42576(15) 0.0412(6) Uani 1 1 d . . .
C2 C 0.6354(2) 0.02253(19) 0.50863(14) 0.0346(5) Uani 1 1 d . . .
C3 C 0.7634(2) 0.04388(19) 0.51890(15) 0.0383(6) Uani 1 1 d . . .
C4 C 0.8146(2) 0.0544(2) 0.59712(17) 0.0503(8) Uani 1 1 d . . .
H4 H 0.8992 0.0694 0.6028 0.060 Uiso 1 1 calc R . .
C5 C 0.7415(3) 0.0430(2) 0.66613(17) 0.0552(8) Uani 1 1 d . . .
H5 H 0.7760 0.0495 0.7187 0.066 Uiso 1 1 calc R . .
C6 C 0.6171(2) 0.0219(2) 0.65673(16) 0.0443(7) Uani 1 1 d . . .
C7 C 0.5607(2) 0.01176(19) 0.57937(14) 0.0359(6) Uani 1 1 d . . .
C8 C 0.3876(4) 0.2327(3) 0.4731(3) 0.0839(13) Uani 1 1 d . . .
C9 C 0.4340(4) 0.2395(2) 0.5562(3) 0.0849(14) Uani 1 1 d . . .
C10 C 0.3526(5) 0.2246(4) 0.6185(4) 0.1161(19) Uani 1 1 d . . .
H10 H 0.3807 0.2286 0.6729 0.139 Uiso 1 1 calc R . .
C11 C 0.2295(6) 0.2038(4) 0.6032(6) 0.149(3) Uani 1 1 d . . .
H11 H 0.1756 0.1924 0.6474 0.179 Uiso 1 1 calc R . .
C12 C 0.1840(6) 0.1992(4) 0.5239(8) 0.164(5) Uani 1 1 d . . .
H12 H 0.0991 0.1866 0.5157 0.197 Uiso 1 1 calc R . .
C13 C 0.2599(6) 0.2128(3) 0.4562(5) 0.124(2) Uani 1 1 d . . .
C14 C 0.2123(7) 0.2092(4) 0.3711(6) 0.192(4) Uani 1 1 d . . .
H14A H 0.2573 0.1630 0.3406 0.231 Uiso 1 1 calc R . .
H14B H 0.2241 0.2681 0.3451 0.231 Uiso 1 1 calc R . .
H14C H 0.1243 0.1943 0.3717 0.231 Uiso 1 1 calc R . .
O1 O 0.63712(19) 0.0164(2) 0.36270(13) 0.0811(9) Uani 1 1 d . . .
O2 O 0.5047(2) 0.0784(2) 0.76761(14) 0.0760(8) Uani 1 1 d . . .
O3 O 0.5410(2) -0.0674(2) 0.76351(15) 0.0747(7) Uani 1 1 d . . .
N1 N 0.5462(2) 0.0095(2) 0.73462(15) 0.0544(7) Uani 1 1 d . . .
S1 S 0.5000 0.2500 0.39831(14) 0.1115(7) Uani 1 2 d S . .
Cl1 Cl 0.86638(6) 0.05790(6) 0.43736(4) 0.0529(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
C1 O1 1.203(3) . ?
C1 C2 1.484(3) . ?
C1 C7 1.506(3) 5_656 ?
C2 C7 1.400(3) . ?
C2 C3 1.406(3) . ?
C3 C4 1.384(4) . ?
C3 Cl1 1.725(2) . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(3) . ?
C6 N1 1.478(4) . ?
C7 C1 1.506(3) 5_656 ?
C8 C13 1.416(7) . ?
C8 C9 1.433(7) . ?
C8 S1 1.718(5) . ?
C9 C10 1.345(7) . ?
C9 C9 1.436(8) 2_655 ?
C10 C11 1.366(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.466(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O2 N1 1.214(3) . ?
O3 N1 1.211(4) . ?
S1 C8 1.717(5) 2_655 ?

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
O1 C1 C2 122.5(2) . . ?
O1 C1 C7 118.9(2) . 5_656 ?
C2 C1 C7 118.6(2) . 5_656 ?
C7 C2 C3 118.5(2) . . ?
C7 C2 C1 119.2(2) . . ?
C3 C2 C1 122.3(2) . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 Cl1 115.74(19) . . ?
C2 C3 Cl1 123.41(19) . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 122.7(2) . . ?
C5 C6 N1 115.3(2) . . ?
C7 C6 N1 122.0(2) . . ?
C6 C7 C2 118.4(2) . . ?
C6 C7 C1 119.5(2) . 5_656 ?
C2 C7 C1 122.1(2) . 5_656 ?
C13 C8 C9 121.7(5) . . ?
C13 C8 S1 124.2(5) . . ?
C9 C8 S1 114.2(3) . . ?
C10 C9 C8 118.0(5) . . ?
C10 C9 C9 131.5(4) . 2_655 ?
C8 C9 C9 110.5(2) . 2_655 ?
C9 C10 C11 121.1(7) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 121.2(7) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 122.0(6) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C8 116.1(7) . . ?
C12 C13 C14 122.6(7) . . ?
C8 C13 C14 121.3(8) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 N1 O2 124.9(3) . . ?
O3 N1 C6 117.6(3) . . ?
O2 N1 C6 117.3(3) . . ?
C8 S1 C8 90.6(3) 2_655 . ?

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
O1 C1 C2 C7 -178.1(3) . . . . ?
C7 C1 C2 C7 0.9(4) 5_656 . . . ?
O1 C1 C2 C3 1.4(5) . . . . ?
C7 C1 C2 C3 -179.6(3) 5_656 . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C7 C2 C3 Cl1 179.3(2) . . . . ?
C1 C2 C3 Cl1 -0.2(4) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
Cl1 C3 C4 C5 -178.7(3) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C4 C5 C6 N1 179.2(3) . . . . ?
C5 C6 C7 C2 0.8(4) . . . . ?
N1 C6 C7 C2 -178.5(3) . . . . ?
C5 C6 C7 C1 -179.2(3) . . . 5_656 ?
N1 C6 C7 C1 1.4(4) . . . 5_656 ?
C3 C2 C7 C6 -0.6(4) . . . . ?
C1 C2 C7 C6 178.9(3) . . . . ?
C3 C2 C7 C1 179.5(3) . . . 5_656 ?
C1 C2 C7 C1 -1.0(4) . . . 5_656 ?
C13 C8 C9 C10 1.3(6) . . . . ?
S1 C8 C9 C10 -178.4(3) . . . . ?
C13 C8 C9 C9 -179.8(4) . . . 2_655 ?
S1 C8 C9 C9 0.5(5) . . . 2_655 ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C9 C9 C10 C11 -178.7(6) 2_655 . . . ?
C9 C10 C11 C12 -1.4(10) . . . . ?
C10 C11 C12 C13 1.8(11) . . . . ?
C11 C12 C13 C8 -0.6(9) . . . . ?
C11 C12 C13 C14 -179.3(6) . . . . ?
C9 C8 C13 C12 -0.9(7) . . . . ?
S1 C8 C13 C12 178.8(4) . . . . ?
C9 C8 C13 C14 177.7(4) . . . . ?
S1 C8 C13 C14 -2.6(7) . . . . ?
C5 C6 N1 O3 -90.7(4) . . . . ?
C7 C6 N1 O3 88.7(3) . . . . ?
C5 C6 N1 O2 84.5(3) . . . . ?
C7 C6 N1 O2 -96.2(4) . . . . ?
C13 C8 S1 C8 -179.9(5) . . . 2_655 ?
C9 C8 S1 C8 -0.17(18) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.19
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.057
