# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1022848'
_audit_update_record             
;
2014-09-03 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl F N4 O3'
_chemical_formula_weight         418.85

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   22.318(4)
_cell_length_b                   10.108(3)
_cell_length_c                   9.029(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2036.9(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4092
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01

_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.225

_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)



_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25820
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4092
_reflns_number_gt                3252
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'BRUKER APEX2 (Bruker, 2005)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 3.0'
_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 > 2σ(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)+(0.1698P)²+0.3375P] 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   0.1(2)
_refine_ls_number_reflns         4092
_refine_ls_number_parameters     270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.2366
_refine_ls_wR_factor_gt          0.2212
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C12 C 0.29077(13) 0.8949(3) 0.4881(4) 0.0467(7) Uani 1 1 d . . .
N3 N 0.31927(16) 0.6874(3) 0.3750(4) 0.0544(7) Uani 1 1 d . . .
O1 O 0.37006(13) 0.7563(3) 0.5731(4) 0.0716(8) Uani 1 1 d . . .
C16 C 0.40508(17) 0.4025(4) 0.3602(4) 0.0564(9) Uani 1 1 d . . .
N2 N 0.25285(13) 1.0850(3) 0.6243(4) 0.0579(8) Uani 1 1 d . . .
C8 C 0.29139(13) 0.9828(4) 0.6144(4) 0.0518(8) Uani 1 1 d . . .
N4 N 0.35282(13) 0.5750(3) 0.3701(3) 0.0511(7) Uani 1 1 d . . .
C15 C 0.39889(17) 0.5345(4) 0.2748(4) 0.0576(9) Uani 1 1 d . . .
N1 N 0.32975(17) 0.9647(5) 0.7264(5) 0.0787(13) Uani 1 1 d . . .
O3 O 0.32341(19) 0.4257(4) 0.5569(4) 0.0922(11) Uani 1 1 d . . .
C13 C 0.32983(13) 0.7759(3) 0.4846(4) 0.0473(7) Uani 1 1 d . . .
C6 C 0.39070(16) 1.0499(4) 0.9275(4) 0.0581(9) Uani 1 1 d . . .
O2 O 0.42184(17) 0.5863(4) 0.1734(4) 0.1001(14) Uani 1 1 d . . .
C11 C 0.25140(16) 0.9241(3) 0.3741(4) 0.0544(8) Uani 1 1 d . . .
H11 H 0.2501 0.8699 0.2908 0.065 Uiso 1 1 calc R . .
C10 C 0.2136(2) 1.0343(5) 0.3829(5) 0.0703(11) Uani 1 1 d . . .
H10 H 0.1880 1.0568 0.3054 0.084 Uiso 1 1 calc R . .
C14 C 0.35432(18) 0.4588(4) 0.4549(4) 0.0559(8) Uani 1 1 d . . .
C9 C 0.2157(2) 1.1077(5) 0.5105(5) 0.0675(10) Uani 1 1 d . . .
H9 H 0.1893 1.1786 0.5188 0.081 Uiso 1 1 calc R . .
C7 C 0.3295(2) 1.0479(7) 0.8600(6) 0.098(2) Uani 1 1 d . . .
H7A H 0.3009 1.0132 0.9309 0.117 Uiso 1 1 calc R . .
H7B H 0.3175 1.1372 0.8343 0.117 Uiso 1 1 calc R . .
C17 C 0.4650(2) 0.3890(6) 0.4363(5) 0.0768(12) Uani 1 1 d . . .
H17A H 0.4623 0.3183 0.5086 0.092 Uiso 1 1 calc R . .
H17B H 0.4732 0.4703 0.4897 0.092 Uiso 1 1 calc R . .
C1 C 0.4355(2) 1.1417(5) 0.9113(5) 0.0751(12) Uani 1 1 d . . .
C4 C 0.4600(4) 0.9358(8) 1.0948(10) 0.127(3) Uani 1 1 d . . .
H4 H 0.4680 0.8650 1.1577 0.152 Uiso 1 1 calc R . .
C2 C 0.4907(2) 1.1290(7) 0.9815(8) 0.0934(18) Uani 1 1 d . . .
H2 H 0.5201 1.1928 0.9672 0.112 Uiso 1 1 calc R . .
C19 C 0.3862(3) 0.2791(7) 0.2755(8) 0.106(2) Uani 1 1 d . . .
H19A H 0.4157 0.2653 0.1981 0.127 Uiso 1 1 calc R . .
H19B H 0.3898 0.2051 0.3434 0.127 Uiso 1 1 calc R . .
C18 C 0.5173(2) 0.3605(7) 0.3338(6) 0.0893(15) Uani 1 1 d . . .
H18A H 0.5535 0.3545 0.3907 0.134 Uiso 1 1 calc R . .
H18B H 0.5210 0.4307 0.2626 0.134 Uiso 1 1 calc R . .
H18C H 0.5105 0.2784 0.2831 0.134 Uiso 1 1 calc R . .
C3 C 0.5011(3) 1.0289(8) 1.0665(9) 0.104(2) Uani 1 1 d . . .
H3 H 0.5388 1.0211 1.1098 0.125 Uiso 1 1 calc R . .
C5 C 0.4056(3) 0.9499(5) 1.0267(9) 0.099(2) Uani 1 1 d . . .
Cl1 Cl 0.42138(15) 1.2773(3) 0.8025(3) 0.1844(14) Uani 1 1 d . . .
F1 F 0.3619(3) 0.8605(4) 1.0574(13) 0.215(4) Uani 1 1 d . . .
C20 C 0.3297(3) 0.2692(8) 0.2088(11) 0.121(3) Uani 1 1 d . . .
H20A H 0.3255 0.1836 0.1641 0.181 Uiso 1 1 calc R . .
H29B H 0.3257 0.3364 0.1343 0.181 Uiso 1 1 calc R . .
H20C H 0.2991 0.2809 0.2825 0.181 Uiso 1 1 calc R . .
H1N H 0.351(2) 0.904(4) 0.728(5) 0.048(10) Uiso 1 1 d . . .
H3N H 0.2917(19) 0.686(4) 0.335(5) 0.044(11) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C12 C11 1.385(5) . ?
C12 C8 1.446(4) . ?
C12 C13 1.486(5) . ?
N3 C13 1.355(5) . ?
N3 N4 1.361(4) . ?
O1 C13 1.218(4) . ?
C16 C17 1.509(6) . ?
C16 C19 1.522(7) . ?
C16 C14 1.529(5) . ?
C16 C15 1.547(6) . ?
N2 C9 1.340(5) . ?
N2 C8 1.347(5) . ?
C8 N1 1.337(5) . ?
N4 C14 1.401(5) . ?
N4 C15 1.402(4) . ?
C15 O2 1.172(5) . ?
N1 C7 1.470(5) . ?
O3 C14 1.199(5) . ?
C6 C1 1.372(7) . ?
C6 C5 1.390(8) . ?
C6 C7 1.495(6) . ?
C11 C10 1.400(6) . ?
C10 C9 1.371(6) . ?
C17 C18 1.518(7) . ?
C1 C2 1.390(8) . ?
C1 Cl1 1.716(5) . ?
C4 C3 1.340(12) . ?
C4 C5 1.369(10) . ?
C2 C3 1.292(11) . ?
C19 C20 1.401(10) . ?
C5 F1 1.358(8) . ?

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
C11 C12 C8 117.5(3) . . ?
C11 C12 C13 121.9(3) . . ?
C8 C12 C13 120.6(3) . . ?
C13 N3 N4 118.6(3) . . ?
C17 C16 C19 113.6(4) . . ?
C17 C16 C14 115.8(3) . . ?
C19 C16 C14 112.4(4) . . ?
C17 C16 C15 112.6(4) . . ?
C19 C16 C15 115.6(4) . . ?
C14 C16 C15 83.8(3) . . ?
C9 N2 C8 118.4(3) . . ?
N1 C8 N2 117.6(3) . . ?
N1 C8 C12 121.2(3) . . ?
N2 C8 C12 121.1(3) . . ?
N3 N4 C14 134.0(3) . . ?
N3 N4 C15 131.8(3) . . ?
C14 N4 C15 94.2(3) . . ?
O2 C15 N4 132.0(4) . . ?
O2 C15 C16 137.3(4) . . ?
N4 C15 C16 90.6(3) . . ?
C8 N1 C7 122.7(4) . . ?
O1 C13 N3 120.0(3) . . ?
O1 C13 C12 123.4(3) . . ?
N3 C13 C12 116.6(3) . . ?
C1 C6 C5 112.7(4) . . ?
C1 C6 C7 129.1(5) . . ?
C5 C6 C7 118.1(5) . . ?
C12 C11 C10 120.7(3) . . ?
C9 C10 C11 117.2(4) . . ?
O3 C14 N4 129.8(4) . . ?
O3 C14 C16 138.7(4) . . ?
N4 C14 C16 91.4(3) . . ?
N2 C9 C10 125.0(4) . . ?
N1 C7 C6 109.8(3) . . ?
C16 C17 C18 114.9(4) . . ?
C6 C1 C2 122.3(5) . . ?
C6 C1 Cl1 117.9(4) . . ?
C2 C1 Cl1 119.8(5) . . ?
C3 C4 C5 116.7(6) . . ?
C3 C2 C1 120.2(6) . . ?
C20 C19 C16 121.5(6) . . ?
C2 C3 C4 122.7(6) . . ?
F1 C5 C4 118.4(7) . . ?
F1 C5 C6 116.4(6) . . ?
C4 C5 C6 125.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1022849'
_audit_update_record             
;
2014-09-03 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N2 O4 S'
_chemical_formula_weight         310.36

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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                   6.702(3)
_cell_length_b                   11.902(6)
_cell_length_c                   18.892(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1507.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5265
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      32.22

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01

_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.232

_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)



_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19864
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         32.22
_reflns_number_total             5262
_reflns_number_gt                4357
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       'BRUKER APEX2 (Bruker, 2005)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 3.0'
_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 > 2σ(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)+(0.0427P)²+0.1076P] 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   -0.04(6)
_refine_ls_number_reflns         5262
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
S1 S 0.82783(6) 0.87717(3) 0.07858(2) 0.01620(8) Uani 1 1 d . . .
O1 O 0.76540(19) 0.88978(11) 0.15056(6) 0.0242(3) Uani 1 1 d . . .
O2 O 0.69146(17) 0.89073(10) 0.02079(6) 0.0199(2) Uani 1 1 d . . .
O3 O 1.38131(18) 0.75196(10) 0.08805(7) 0.0211(3) Uani 1 1 d . . .
N1 N 0.9077(2) 0.74482(11) 0.07015(8) 0.0160(3) Uani 1 1 d . . .
O4 O 0.87298(19) 0.61513(12) 0.21248(7) 0.0294(3) Uani 1 1 d . . .
N2 N 1.0455(2) 0.71014(12) 0.12040(7) 0.0165(3) Uani 1 1 d . . .
C4 C 1.3612(3) 1.10594(14) 0.04182(10) 0.0227(3) Uani 1 1 d . . .
C11 C 1.3482(3) 0.53460(15) 0.19537(10) 0.0255(4) Uani 1 1 d . . .
H9A H 1.3332 0.5001 0.2416 0.031 Uiso 1 1 calc R . .
H9B H 1.4898 0.5453 0.1871 0.031 Uiso 1 1 calc R . .
C1 C 1.0344(3) 0.96577(14) 0.06466(9) 0.0179(3) Uani 1 1 d . . .
C6 C 1.1024(3) 1.03394(15) 0.11910(10) 0.0222(4) Uani 1 1 d . . .
H11 H 1.0400 1.0331 0.1631 0.027 Uiso 1 1 calc R . .
C12 C 1.2672(3) 0.45330(16) 0.13925(11) 0.0305(4) Uani 1 1 d . . .
H12A H 1.3389 0.3836 0.1418 0.046 Uiso 1 1 calc R . .
H12B H 1.2841 0.4856 0.0931 0.046 Uiso 1 1 calc R . .
H12C H 1.1280 0.4398 0.1478 0.046 Uiso 1 1 calc R . .
C2 C 1.1283(3) 0.96596(14) -0.00167(9) 0.0199(3) Uani 1 1 d . . .
H13 H 1.0827 0.9199 -0.0380 0.024 Uiso 1 1 calc R . .
C3 C 1.2901(3) 1.03616(15) -0.01186(10) 0.0228(4) Uani 1 1 d . . .
H14 H 1.3532 1.0369 -0.0557 0.027 Uiso 1 1 calc R . .
C5 C 1.2656(3) 1.10370(14) 0.10680(10) 0.0261(4) Uani 1 1 d . . .
H15 H 1.3114 1.1498 0.1431 0.031 Uiso 1 1 calc R . .
C8 C 1.2557(2) 0.71380(13) 0.12594(8) 0.0162(3) Uani 1 1 d . . .
C13 C 1.3178(3) 0.71914(16) 0.26054(10) 0.0272(4) Uani 1 1 d . . .
H17A H 1.2840 0.6788 0.3035 0.033 Uiso 1 1 calc R . .
H17B H 1.4620 0.7254 0.2586 0.033 Uiso 1 1 calc R . .
C10 C 1.0196(3) 0.64960(14) 0.18396(9) 0.0189(3) Uani 1 1 d . . .
C9 C 1.2475(3) 0.64961(14) 0.19683(9) 0.0191(3) Uani 1 1 d . . .
C7 C 1.5387(3) 1.18141(17) 0.02924(12) 0.0343(5) Uani 1 1 d . . .
H20A H 1.5848 1.1722 -0.0185 0.051 Uiso 1 1 calc R . .
H20B H 1.6437 1.1618 0.0615 0.051 Uiso 1 1 calc R . .
H20C H 1.5004 1.2582 0.0367 0.051 Uiso 1 1 calc R . .
C14 C 1.2295(4) 0.83701(19) 0.26498(12) 0.0396(5) Uani 1 1 d . . .
H21A H 1.2814 0.8747 0.3060 0.059 Uiso 1 1 calc R . .
H21B H 1.0869 0.8320 0.2685 0.059 Uiso 1 1 calc R . .
H21C H 1.2647 0.8786 0.2233 0.059 Uiso 1 1 calc R . .
H1N H 0.939(4) 0.729(2) 0.0310(12) 0.036(7) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.4308(13) . ?
S1 O2 1.4328(12) . ?
S1 N1 1.6714(16) . ?
S1 C1 1.7602(18) . ?
O3 C8 1.1948(19) . ?
N1 N2 1.3871(19) . ?
O4 C10 1.194(2) . ?
N2 C10 1.411(2) . ?
N2 C8 1.413(2) . ?
C4 C5 1.385(3) . ?
C4 C3 1.395(2) . ?
C4 C7 1.509(3) . ?
C11 C9 1.526(3) . ?
C11 C12 1.535(3) . ?
C1 C6 1.387(2) . ?
C1 C2 1.402(2) . ?
C6 C5 1.393(3) . ?
C2 C3 1.382(2) . ?
C8 C9 1.543(2) . ?
C13 C14 1.525(3) . ?
C13 C9 1.535(2) . ?
C10 C9 1.546(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
O1 S1 O2 121.72(8) . . ?
O1 S1 N1 106.45(8) . . ?
O2 S1 N1 103.77(7) . . ?
O1 S1 C1 108.00(8) . . ?
O2 S1 C1 108.69(8) . . ?
N1 S1 C1 107.36(8) . . ?
N2 N1 S1 115.37(11) . . ?
N1 N2 C10 130.74(14) . . ?
N1 N2 C8 134.83(14) . . ?
C10 N2 C8 94.31(13) . . ?
C5 C4 C3 118.34(16) . . ?
C5 C4 C7 121.04(17) . . ?
C3 C4 C7 120.62(17) . . ?
C9 C11 C12 114.94(15) . . ?
C6 C1 C2 120.97(16) . . ?
C6 C1 S1 119.87(13) . . ?
C2 C1 S1 119.16(13) . . ?
C1 C6 C5 118.87(17) . . ?
C3 C2 C1 118.51(16) . . ?
C2 C3 C4 121.78(17) . . ?
C4 C5 C6 121.52(16) . . ?
O3 C8 N2 132.05(16) . . ?
O3 C8 C9 137.16(16) . . ?
N2 C8 C9 90.78(13) . . ?
C14 C13 C9 114.84(16) . . ?
O4 C10 N2 131.36(16) . . ?
O4 C10 C9 137.92(16) . . ?
N2 C10 C9 90.71(13) . . ?
C11 C9 C13 111.22(15) . . ?
C11 C9 C8 114.38(14) . . ?
C13 C9 C8 113.75(15) . . ?
C11 C9 C10 115.70(15) . . ?
C13 C9 C10 115.25(15) . . ?
C8 C9 C10 84.18(12) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        32.22
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.057

