# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_HAMH205_0m
_database_code_depnum_ccdc_archive 'CCDC 1514742'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            HAMH205
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H5 F3 N2 O3 S'
_chemical_formula_sum            'C11 H5 F3 N2 O3 S'
_chemical_formula_weight         302.23

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.5438(4)
_cell_length_b                   13.1859(7)
_cell_length_c                   12.5014(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.862(2)
_cell_angle_gamma                90
_cell_volume                     1076.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.2476
_cell_measurement_theta_max      25.2028

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.354
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
; 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            29062
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         25.294
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1953
_reflns_number_gt                1760
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  ?
_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)+(0.0305P)²+1.1028P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1953
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
F1 F 0.78608(16) 0.65192(8) 0.86814(9) 0.0199(3) Uani 1 1 d . . . . .
O1 O 0.23096(17) 0.53534(9) 0.60531(9) 0.0111(3) Uani 1 1 d . . . . .
C1 C 0.3956(2) 0.50284(12) 0.64513(13) 0.0091(3) Uani 1 1 d . . . . .
C2 C 0.5208(3) 0.54876(13) 0.72984(13) 0.0103(4) Uani 1 1 d . . . . .
H2 H 0.4753 0.6085 0.7634 0.012 Uiso 1 1 calc R U . . .
F2 F 0.79903(18) 0.50637(9) 0.94638(8) 0.0260(3) Uani 1 1 d . . . . .
F3 F 1.03202(15) 0.54882(8) 0.84132(8) 0.0171(2) Uani 1 1 d . . . . .
C3 C 0.7034(3) 0.50762(13) 0.76242(13) 0.0099(3) Uani 1 1 d . . . . .
N4 N 0.7843(2) 0.42160(11) 0.72207(11) 0.0101(3) Uani 1 1 d . . . . .
C5 C 0.6681(2) 0.37833(12) 0.64534(13) 0.0088(3) Uani 1 1 d . . . . .
S6 S 0.74119(6) 0.26897(3) 0.58172(3) 0.01109(13) Uani 1 1 d . . . . .
C7 C 0.5157(3) 0.27104(13) 0.49852(13) 0.0096(3) Uani 1 1 d . . . . .
C8 C 0.4574(3) 0.20102(13) 0.41909(13) 0.0108(3) Uani 1 1 d . . . . .
H8 H 0.5471 0.1478 0.4016 0.013 Uiso 1 1 calc R U . . .
O9 O 0.2100(2) 0.14335(9) 0.28729(10) 0.0134(3) Uani 1 1 d . . . . .
H9 H 0.086(4) 0.1426(17) 0.2747(18) 0.024(6) Uiso 1 1 d . . . . .
C9 C 0.2659(3) 0.21057(13) 0.36611(13) 0.0099(3) Uani 1 1 d . . . . .
O10 O -0.05252(18) 0.29090(10) 0.33795(10) 0.0123(3) Uani 1 1 d . . . . .
H10 H -0.114(4) 0.3434(19) 0.3529(19) 0.029(6) Uiso 1 1 d . . . . .
C10 C 0.1337(3) 0.28956(13) 0.39319(13) 0.0093(3) Uani 1 1 d . . . . .
C11 C 0.1931(3) 0.36061(12) 0.47093(13) 0.0088(3) Uani 1 1 d . . . . .
H11 H 0.1044 0.4143 0.4882 0.011 Uiso 1 1 calc R U . . .
C12 C 0.3873(3) 0.35064(12) 0.52288(13) 0.0085(3) Uani 1 1 d . . . . .
N13 N 0.4795(2) 0.41299(10) 0.60534(11) 0.0077(3) Uani 1 1 d . . . . .
C14 C 0.8325(3) 0.55413(14) 0.85443(14) 0.0131(4) 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
F1 C14 1.338(2) . ?
O1 C1 1.233(2) . ?
C1 N13 1.411(2) . ?
C1 C2 1.429(2) . ?
C2 C3 1.350(2) . ?
C2 H2 0.9500 . ?
F2 C14 1.342(2) . ?
F3 C14 1.328(2) . ?
C3 N4 1.363(2) . ?
C3 C14 1.511(2) . ?
N4 C5 1.314(2) . ?
C5 N13 1.378(2) . ?
C5 S6 1.7298(17) . ?
S6 C7 1.7473(17) . ?
C7 C8 1.390(2) . ?
C7 C12 1.391(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
O9 C9 1.357(2) . ?
O9 H9 0.82(2) . ?
C9 C10 1.410(2) . ?
O10 C10 1.359(2) . ?
O10 H10 0.83(3) . ?
C10 C11 1.387(2) . ?
C11 C12 1.394(2) . ?
C11 H11 0.9500 . ?
C12 N13 1.421(2) . ?

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 N13 120.01(15) . . ?
O1 C1 C2 126.41(15) . . ?
N13 C1 C2 113.56(14) . . ?
C3 C2 C1 120.32(16) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 N4 125.51(16) . . ?
C2 C3 C14 120.33(15) . . ?
N4 C3 C14 114.10(15) . . ?
C5 N4 C3 114.31(14) . . ?
N4 C5 N13 125.52(15) . . ?
N4 C5 S6 122.25(13) . . ?
N13 C5 S6 112.23(12) . . ?
C5 S6 C7 90.69(8) . . ?
C8 C7 C12 121.11(16) . . ?
C8 C7 S6 126.51(13) . . ?
C12 C7 S6 112.32(13) . . ?
C9 C8 C7 118.55(15) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C9 O9 H9 111.3(16) . . ?
O9 C9 C8 118.66(15) . . ?
O9 C9 C10 121.12(15) . . ?
C8 C9 C10 120.21(15) . . ?
C10 O10 H10 109.1(17) . . ?
O10 C10 C11 123.16(15) . . ?
O10 C10 C9 115.54(15) . . ?
C11 C10 C9 121.30(15) . . ?
C10 C11 C12 117.83(15) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C7 C12 C11 120.95(15) . . ?
C7 C12 N13 111.24(14) . . ?
C11 C12 N13 127.78(15) . . ?
C5 N13 C1 120.74(14) . . ?
C5 N13 C12 113.42(14) . . ?
C1 N13 C12 125.83(14) . . ?
F3 C14 F1 107.47(14) . . ?
F3 C14 F2 107.43(14) . . ?
F1 C14 F2 106.91(14) . . ?
F3 C14 C3 112.87(14) . . ?
F1 C14 C3 111.61(14) . . ?
F2 C14 C3 110.27(14) . . ?

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 C3 -176.67(16) . . . . ?
N13 C1 C2 C3 1.9(2) . . . . ?
C1 C2 C3 N4 -1.0(3) . . . . ?
C1 C2 C3 C14 -177.95(15) . . . . ?
C2 C3 N4 C5 0.0(2) . . . . ?
C14 C3 N4 C5 177.04(14) . . . . ?
C3 N4 C5 N13 0.1(2) . . . . ?
C3 N4 C5 S6 179.43(12) . . . . ?
N4 C5 S6 C7 -178.61(14) . . . . ?
N13 C5 S6 C7 0.83(13) . . . . ?
C5 S6 C7 C8 -179.59(16) . . . . ?
C5 S6 C7 C12 -2.47(13) . . . . ?
C12 C7 C8 C9 -1.6(2) . . . . ?
S6 C7 C8 C9 175.34(13) . . . . ?
C7 C8 C9 O9 178.89(15) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
O9 C9 C10 O10 2.1(2) . . . . ?
C8 C9 C10 O10 -178.64(15) . . . . ?
O9 C9 C10 C11 -177.59(15) . . . . ?
C8 C9 C10 C11 1.6(2) . . . . ?
O10 C10 C11 C12 179.35(15) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C8 C7 C12 C11 2.3(2) . . . . ?
S6 C7 C12 C11 -175.04(13) . . . . ?
C8 C7 C12 N13 -179.27(15) . . . . ?
S6 C7 C12 N13 3.43(17) . . . . ?
C10 C11 C12 C7 -1.0(2) . . . . ?
C10 C11 C12 N13 -179.15(15) . . . . ?
N4 C5 N13 C1 1.0(2) . . . . ?
S6 C5 N13 C1 -178.42(11) . . . . ?
N4 C5 N13 C12 -179.61(15) . . . . ?
S6 C5 N13 C12 0.97(17) . . . . ?
O1 C1 N13 C5 176.78(15) . . . . ?
C2 C1 N13 C5 -1.9(2) . . . . ?
O1 C1 N13 C12 -2.5(2) . . . . ?
C2 C1 N13 C12 178.79(14) . . . . ?
C7 C12 N13 C5 -2.84(19) . . . . ?
C11 C12 N13 C5 175.50(16) . . . . ?
C7 C12 N13 C1 176.51(14) . . . . ?
C11 C12 N13 C1 -5.1(3) . . . . ?
C2 C3 C14 F3 -144.19(16) . . . . ?
N4 C3 C14 F3 38.6(2) . . . . ?
C2 C3 C14 F1 -23.0(2) . . . . ?
N4 C3 C14 F1 159.73(14) . . . . ?
C2 C3 C14 F2 95.66(19) . . . . ?
N4 C3 C14 F2 -81.60(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 N4 0.82(2) 2.21(2) 2.9755(19) 157(2) 4_465
O10 H10 O1 0.83(3) 1.86(3) 2.6884(17) 175(2) 3_566

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_HAMH285_0m
_database_code_depnum_ccdc_archive 'CCDC 1514743'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            HAMH285
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O3 S'
_chemical_formula_sum            'C15 H18 N2 O3 S'
_chemical_formula_weight         306.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6208(4)
_cell_length_b                   11.6290(4)
_cell_length_c                   15.4798(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.090(1)
_cell_angle_gamma                90
_cell_volume                     1498.36(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.4469
_cell_measurement_theta_max      27.5103

_exptl_crystal_description       nugget
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
; 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            17300
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.219
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3446
_reflns_number_gt                3141
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  ?
_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)+(0.0361P)²+0.9710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3446
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_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
C1 C 0.97569(14) 0.45179(11) 0.86949(8) 0.0119(2) Uani 1 1 d . . . . .
O1 O 1.08011(10) 0.40653(8) 0.93228(6) 0.01420(19) Uani 1 1 d . . . . .
S1 S 0.63605(4) 0.68547(3) 0.85691(2) 0.01396(9) Uani 1 1 d . . . . .
N2 N 0.87441(12) 0.53441(9) 0.88780(7) 0.0114(2) Uani 1 1 d . . . . .
H2 H 0.888(2) 0.5564(15) 0.9420(12) 0.023(4) Uiso 1 1 d . . . . .
C3 C 0.75698(14) 0.58266(10) 0.82136(8) 0.0114(2) Uani 1 1 d . . . . .
N4 N 0.73394(13) 0.55871(9) 0.73711(7) 0.0138(2) Uani 1 1 d . . . . .
C5 C 0.83472(14) 0.48023(11) 0.71432(8) 0.0132(2) Uani 1 1 d . . . . .
C6 C 0.95203(15) 0.42540(11) 0.77726(8) 0.0139(2) Uani 1 1 d . . . . .
H6 H 1.0179 0.3696 0.7594 0.017 Uiso 1 1 calc R U . . .
C7 C 0.80307(15) 0.46060(12) 0.61412(8) 0.0163(3) Uani 1 1 d . . . . .
C8 C 0.63692(16) 0.40373(12) 0.58114(9) 0.0185(3) Uani 1 1 d . . . . .
H8A H 0.6102 0.3953 0.5159 0.028 Uiso 1 1 calc R U . . .
H8B H 0.5558 0.4519 0.5976 0.028 Uiso 1 1 calc R U . . .
H8C H 0.6389 0.3278 0.6088 0.028 Uiso 1 1 calc R U . . .
C9 C 0.80038(19) 0.57840(14) 0.56840(9) 0.0244(3) Uani 1 1 d . . . . .
H9A H 0.7779 0.5677 0.5035 0.037 Uiso 1 1 calc R U . . .
H9B H 0.9050 0.6159 0.5905 0.037 Uiso 1 1 calc R U . . .
H9C H 0.7166 0.6266 0.5821 0.037 Uiso 1 1 calc R U . . .
C10 C 0.93132(17) 0.38429(15) 0.59155(9) 0.0260(3) Uani 1 1 d . . . . .
H10A H 0.9106 0.3775 0.5264 0.039 Uiso 1 1 calc R U . . .
H10B H 0.9281 0.3078 0.6176 0.039 Uiso 1 1 calc R U . . .
H10C H 1.0375 0.4186 0.6161 0.039 Uiso 1 1 calc R U . . .
C11 C 0.53034(15) 0.74128(11) 0.75100(8) 0.0124(2) Uani 1 1 d . . . . .
C12 C 0.61421(15) 0.81379(11) 0.70716(8) 0.0136(2) Uani 1 1 d . . . . .
H12 H 0.7223 0.8339 0.7354 0.016 Uiso 1 1 calc R U . . .
O13 O 0.61629(11) 0.92574(8) 0.57479(6) 0.01583(19) Uani 1 1 d . . . . .
H13 H 0.715(3) 0.9073(18) 0.5807(14) 0.039(6) Uiso 1 1 d . . . . .
C13 C 0.54135(15) 0.85648(10) 0.62316(8) 0.0124(2) Uani 1 1 d . . . . .
O14 O 0.30213(11) 0.87370(8) 0.50263(6) 0.0158(2) Uani 1 1 d . . . . .
H14 H 0.365(2) 0.9153(17) 0.4851(13) 0.030(5) Uiso 1 1 d . . . . .
C14 C 0.37943(15) 0.83102(10) 0.58429(8) 0.0120(2) Uani 1 1 d . . . . .
C15 C 0.29604(15) 0.76099(10) 0.62907(8) 0.0129(2) Uani 1 1 d . . . . .
H15 H 0.1858 0.7453 0.6024 0.015 Uiso 1 1 calc R U . . .
C16 C 0.36994(15) 0.71280(11) 0.71252(8) 0.0125(2) Uani 1 1 d . . . . .
C17 C 0.27557(16) 0.63194(12) 0.75540(9) 0.0192(3) Uani 1 1 d . . . . .
H17A H 0.1650 0.6265 0.7180 0.029 Uiso 1 1 calc R U . . .
H17B H 0.2748 0.6610 0.8147 0.029 Uiso 1 1 calc R U . . .
H17C H 0.3255 0.5556 0.7614 0.029 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
C1 O1 1.2556(15) . ?
C1 N2 1.3765(16) . ?
C1 C6 1.4220(16) . ?
S1 C3 1.7658(12) . ?
S1 C11 1.7781(12) . ?
N2 C3 1.3621(15) . ?
N2 H2 0.857(18) . ?
C3 N4 1.2973(15) . ?
N4 C5 1.3681(16) . ?
C5 C6 1.3658(17) . ?
C5 C7 1.5205(16) . ?
C6 H6 0.9500 . ?
C7 C10 1.5275(19) . ?
C7 C8 1.5391(18) . ?
C7 C9 1.539(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.3957(17) . ?
C11 C12 1.3964(17) . ?
C12 C13 1.3808(17) . ?
C12 H12 0.9500 . ?
O13 C13 1.3707(15) . ?
O13 H13 0.86(2) . ?
C13 C14 1.4003(17) . ?
O14 C14 1.3600(14) . ?
O14 H14 0.82(2) . ?
C14 C15 1.3857(17) . ?
C15 C16 1.4000(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.5059(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O1 C1 N2 119.90(11) . . ?
O1 C1 C6 124.98(11) . . ?
N2 C1 C6 115.12(11) . . ?
C3 S1 C11 99.34(6) . . ?
C3 N2 C1 121.24(10) . . ?
C3 N2 H2 120.0(12) . . ?
C1 N2 H2 118.7(12) . . ?
N4 C3 N2 124.05(11) . . ?
N4 C3 S1 120.69(9) . . ?
N2 C3 S1 115.25(9) . . ?
C3 N4 C5 117.45(11) . . ?
C6 C5 N4 121.97(11) . . ?
C6 C5 C7 124.09(11) . . ?
N4 C5 C7 113.94(11) . . ?
C5 C6 C1 120.10(11) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C7 C10 111.85(11) . . ?
C5 C7 C8 107.89(10) . . ?
C10 C7 C8 109.94(11) . . ?
C5 C7 C9 108.22(11) . . ?
C10 C7 C9 109.69(12) . . ?
C8 C7 C9 109.18(11) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.12(11) . . ?
C16 C11 S1 121.33(9) . . ?
C12 C11 S1 117.56(9) . . ?
C13 C12 C11 120.57(11) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C13 O13 H13 112.9(14) . . ?
O13 C13 C12 124.20(11) . . ?
O13 C13 C14 116.64(11) . . ?
C12 C13 C14 119.13(11) . . ?
C14 O14 H14 108.5(13) . . ?
O14 C14 C15 119.14(11) . . ?
O14 C14 C13 120.97(11) . . ?
C15 C14 C13 119.88(11) . . ?
C14 C15 C16 121.75(11) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C15 117.46(11) . . ?
C11 C16 C17 123.30(11) . . ?
C15 C16 C17 119.23(11) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C1 N2 C3 -178.09(11) . . . . ?
C6 C1 N2 C3 2.46(17) . . . . ?
C1 N2 C3 N4 -2.31(19) . . . . ?
C1 N2 C3 S1 179.02(9) . . . . ?
C11 S1 C3 N4 -8.64(12) . . . . ?
C11 S1 C3 N2 170.08(9) . . . . ?
N2 C3 N4 C5 -0.15(18) . . . . ?
S1 C3 N4 C5 178.45(9) . . . . ?
C3 N4 C5 C6 2.28(18) . . . . ?
C3 N4 C5 C7 -177.88(11) . . . . ?
N4 C5 C6 C1 -1.97(19) . . . . ?
C7 C5 C6 C1 178.20(12) . . . . ?
O1 C1 C6 C5 -179.83(12) . . . . ?
N2 C1 C6 C5 -0.42(18) . . . . ?
C6 C5 C7 C10 -7.39(18) . . . . ?
N4 C5 C7 C10 172.78(12) . . . . ?
C6 C5 C7 C8 113.65(14) . . . . ?
N4 C5 C7 C8 -66.19(14) . . . . ?
C6 C5 C7 C9 -128.33(14) . . . . ?
N4 C5 C7 C9 51.83(14) . . . . ?
C3 S1 C11 C16 105.25(11) . . . . ?
C3 S1 C11 C12 -74.07(11) . . . . ?
C16 C11 C12 C13 -1.91(19) . . . . ?
S1 C11 C12 C13 177.41(9) . . . . ?
C11 C12 C13 O13 -178.37(11) . . . . ?
C11 C12 C13 C14 3.30(18) . . . . ?
O13 C13 C14 O14 -0.08(17) . . . . ?
C12 C13 C14 O14 178.37(11) . . . . ?
O13 C13 C14 C15 179.64(11) . . . . ?
C12 C13 C14 C15 -1.90(18) . . . . ?
O14 C14 C15 C16 178.79(11) . . . . ?
C13 C14 C15 C16 -0.94(18) . . . . ?
C12 C11 C16 C15 -0.90(18) . . . . ?
S1 C11 C16 C15 179.80(9) . . . . ?
C12 C11 C16 C17 177.87(12) . . . . ?
S1 C11 C16 C17 -1.43(17) . . . . ?
C14 C15 C16 C11 2.31(18) . . . . ?
C14 C15 C16 C17 -176.51(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.857(18) 1.941(18) 2.7954(13) 175.4(17) 3_767
O13 H13 O1 0.86(2) 1.83(2) 2.6572(13) 161(2) 2_756
O14 H14 O13 0.82(2) 2.255(19) 2.7155(13) 115.9(16) .
O14 H14 O13 0.82(2) 2.09(2) 2.7944(13) 143.3(18) 3_676

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.050

