# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_S3
_database_code_depnum_ccdc_archive 'CCDC 1506338'
_audit_update_record             
;
2017-01-08 deposited with the CCDC.
2017-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            S3
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N3 O S'
_chemical_formula_weight         401.52

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   26.886(3)
_cell_length_b                   10.6027(18)
_cell_length_c                   16.7359(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.293(2)
_cell_angle_gamma                90.00
_cell_volume                     4160.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5199
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.44

_exptl_crystal_description       ?
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.176
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14422
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3657
_reflns_number_gt                2829
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0604P)²+1.3973P] 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     SHELXL
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3657
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.07565(2) 0.32945(6) -0.24867(3) 0.0700(2) Uani 1 1 d . . .
O1 O 0.33943(7) 0.52293(13) 0.50943(9) 0.0784(5) Uani 1 1 d . . .
H1 H 0.3242 0.5031 0.4556 0.094 Uiso 1 1 d R . .
N1 N 0.43778(8) 0.33709(17) 0.80599(10) 0.0671(5) Uani 1 1 d . . .
N2 N 0.29005(6) 0.37459(15) 0.36705(9) 0.0515(4) Uani 1 1 d . . .
N3 N 0.05533(8) 0.2652(3) -0.07611(12) 0.0927(7) Uani 1 1 d . . .
C1 C 0.43845(11) 0.5301(3) 0.88852(17) 0.0932(8) Uani 1 1 d . . .
H1A H 0.4026 0.5601 0.8403 0.140 Uiso 1 1 calc R . .
H1B H 0.4619 0.6006 0.9218 0.140 Uiso 1 1 calc R . .
H1C H 0.4320 0.4776 0.9294 0.140 Uiso 1 1 calc R . .
C2 C 0.46790(10) 0.4552(2) 0.84815(14) 0.0782(7) Uani 1 1 d . . .
H2A H 0.4707 0.5058 0.8022 0.094 Uiso 1 1 calc R . .
H2B H 0.5063 0.4357 0.8959 0.094 Uiso 1 1 calc R . .
C3 C 0.50638(11) 0.1611(3) 0.87929(18) 0.0925(8) Uani 1 1 d . . .
H3A H 0.4989 0.1279 0.8211 0.139 Uiso 1 1 calc R . .
H3B H 0.5157 0.0932 0.9223 0.139 Uiso 1 1 calc R . .
H3C H 0.5378 0.2190 0.9014 0.139 Uiso 1 1 calc R . .
C4 C 0.45410(9) 0.2291(2) 0.86848(13) 0.0675(6) Uani 1 1 d . . .
H4A H 0.4225 0.1701 0.8457 0.081 Uiso 1 1 calc R . .
H4B H 0.4613 0.2583 0.9281 0.081 Uiso 1 1 calc R . .
C5 C 0.40164(8) 0.32602(19) 0.71360(12) 0.0525(5) Uani 1 1 d . . .
C6 C 0.38583(8) 0.43081(19) 0.65517(12) 0.0576(5) Uani 1 1 d . . .
H6 H 0.3984 0.5106 0.6800 0.069 Uiso 1 1 calc R . .
C7 C 0.35211(8) 0.41824(17) 0.56170(12) 0.0525(4) Uani 1 1 d . . .
C8 C 0.37917(8) 0.20733(19) 0.67325(12) 0.0562(5) Uani 1 1 d . . .
H8 H 0.3876 0.1361 0.7101 0.067 Uiso 1 1 calc R . .
C9 C 0.34529(8) 0.19698(18) 0.58104(13) 0.0555(5) Uani 1 1 d . . .
H9 H 0.3309 0.1179 0.5565 0.067 Uiso 1 1 calc R . .
C10 C 0.33105(7) 0.29975(17) 0.52126(11) 0.0477(4) Uani 1 1 d . . .
C11 C 0.29916(8) 0.28408(18) 0.42387(12) 0.0517(4) Uani 1 1 d . . .
H11 H 0.2843 0.2048 0.4006 0.062 Uiso 1 1 calc R . .
C12 C 0.25860(7) 0.35330(17) 0.27172(11) 0.0473(4) Uani 1 1 d . . .
C13 C 0.21207(7) 0.27260(18) 0.23073(11) 0.0504(4) Uani 1 1 d . . .
H13 H 0.2015 0.2255 0.2670 0.061 Uiso 1 1 calc R . .
C14 C 0.18129(7) 0.26172(17) 0.13644(11) 0.0484(4) Uani 1 1 d . . .
H14 H 0.1501 0.2077 0.1101 0.058 Uiso 1 1 calc R . .
C15 C 0.27357(8) 0.42178(17) 0.21571(12) 0.0521(4) Uani 1 1 d . . .
H15 H 0.3045 0.4766 0.2420 0.062 Uiso 1 1 calc R . .
C16 C 0.24317(7) 0.40942(17) 0.12158(11) 0.0501(4) Uani 1 1 d . . .
H16 H 0.2544 0.4548 0.0855 0.060 Uiso 1 1 calc R . .
C17 C 0.19600(7) 0.32994(16) 0.07995(11) 0.0444(4) Uani 1 1 d . . .
C18 C 0.16016(7) 0.32352(16) -0.02101(11) 0.0450(4) Uani 1 1 d . . .
C19 C 0.10169(8) 0.2903(2) -0.05331(12) 0.0593(5) Uani 1 1 d . . .
C20 C 0.17850(7) 0.35089(16) -0.08096(12) 0.0475(4) Uani 1 1 d . . .
H20 H 0.2174 0.3667 -0.0545 0.057 Uiso 1 1 calc R . .
C21 C 0.14753(7) 0.35959(16) -0.17914(12) 0.0479(4) Uani 1 1 d . . .
C22 C 0.17166(8) 0.39956(18) -0.23166(12) 0.0557(5) Uani 1 1 d . . .
H22 H 0.2100 0.4203 -0.2072 0.067 Uiso 1 1 calc R . .
C23 C 0.13210(9) 0.4052(2) -0.32534(13) 0.0655(5) Uani 1 1 d . . .
H23 H 0.1413 0.4305 -0.3697 0.079 Uiso 1 1 calc R . .
C24 C 0.07917(10) 0.3699(2) -0.34432(13) 0.0705(6) Uani 1 1 d . . .
H24 H 0.0480 0.3679 -0.4032 0.085 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 C24 1.704(2) . ?
S1 C21 1.7292(18) . ?
O1 C7 1.350(2) . ?
O1 H1 0.8147 . ?
N1 C5 1.371(2) . ?
N1 C4 1.466(3) . ?
N1 C2 1.471(3) . ?
N2 C11 1.287(2) . ?
N2 C12 1.411(2) . ?
N3 C19 1.142(2) . ?
C1 C2 1.496(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.510(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.402(3) . ?
C5 C8 1.416(3) . ?
C6 C7 1.378(2) . ?
C6 H6 0.9300 . ?
C7 C10 1.408(3) . ?
C8 C9 1.359(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.432(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(2) . ?
C12 C15 1.392(3) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9300 . ?
C14 C17 1.393(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.481(2) . ?
C18 C20 1.348(2) . ?
C18 C19 1.434(3) . ?
C20 C21 1.436(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(3) . ?
C22 C23 1.401(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.350(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C24 S1 C21 91.61(10) . . ?
C7 O1 H1 109.6 . . ?
C5 N1 C4 122.51(17) . . ?
C5 N1 C2 122.28(17) . . ?
C4 N1 C2 114.88(16) . . ?
C11 N2 C12 120.54(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 112.3(2) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C3 113.25(18) . . ?
N1 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N1 C5 C6 121.65(17) . . ?
N1 C5 C8 121.04(17) . . ?
C6 C5 C8 117.31(16) . . ?
C7 C6 C5 121.45(18) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O1 C7 C6 118.26(17) . . ?
O1 C7 C10 120.51(16) . . ?
C6 C7 C10 121.23(17) . . ?
C9 C8 C5 120.37(17) . . ?
C9 C8 H8 119.8 . . ?
C5 C8 H8 119.8 . . ?
C8 C9 C10 123.06(18) . . ?
C8 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
C9 C10 C7 116.48(16) . . ?
C9 C10 C11 121.67(17) . . ?
C7 C10 C11 121.78(16) . . ?
N2 C11 C10 123.07(17) . . ?
N2 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C13 C12 C15 118.44(15) . . ?
C13 C12 N2 123.63(16) . . ?
C15 C12 N2 117.86(16) . . ?
C14 C13 C12 120.46(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C17 121.43(16) . . ?
C13 C14 H14 119.3 . . ?
C17 C14 H14 119.3 . . ?
C16 C15 C12 120.93(16) . . ?
C16 C15 H15 119.5 . . ?
C12 C15 H15 119.5 . . ?
C15 C16 C17 120.93(17) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C14 117.79(15) . . ?
C16 C17 C18 121.55(16) . . ?
C14 C17 C18 120.54(15) . . ?
C20 C18 C19 120.33(15) . . ?
C20 C18 C17 124.63(15) . . ?
C19 C18 C17 114.99(15) . . ?
N3 C19 C18 177.6(2) . . ?
C18 C20 C21 130.29(16) . . ?
C18 C20 H20 114.9 . . ?
C21 C20 H20 114.9 . . ?
C22 C21 C20 123.66(16) . . ?
C22 C21 S1 110.16(13) . . ?
C20 C21 S1 126.12(14) . . ?
C21 C22 C23 112.77(17) . . ?
C21 C22 H22 123.6 . . ?
C23 C22 H22 123.6 . . ?
C24 C23 C22 112.79(18) . . ?
C24 C23 H23 123.6 . . ?
C22 C23 H23 123.6 . . ?
C23 C24 S1 112.67(15) . . ?
C23 C24 H24 123.7 . . ?
S1 C24 H24 123.7 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1506300'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.
2017-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        22
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 B F2 N3 O S'
_chemical_formula_weight         449.32

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   6.500(7)
_cell_length_b                   26.53(3)
_cell_length_c                   12.800(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.287(14)
_cell_angle_gamma                90.00
_cell_volume                     2139(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4426
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      25.91

_exptl_crystal_description       Particle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_T_max  0.9664
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11480
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3642
_reflns_number_gt                2599
_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)+(0.1593P)²+2.3297P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3642
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_ref         0.2566
_refine_ls_wR_factor_gt          0.2161
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_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 0.3882(3) 0.38682(6) -0.06193(13) 0.0859(6) Uani 1 1 d . . .
C8 C 0.4088(6) 0.55462(14) 0.4191(3) 0.0376(9) Uani 1 1 d . . .
C5 C 0.4421(6) 0.65456(15) 0.6790(3) 0.0395(9) Uani 1 1 d . . .
C7 C 0.5976(6) 0.59906(14) 0.5711(3) 0.0372(9) Uani 1 1 d . . .
H7 H 0.7194 0.5857 0.5561 0.045 Uiso 1 1 calc R . .
C4 C 0.6215(6) 0.63239(14) 0.6563(3) 0.0375(8) Uani 1 1 d . . .
C11 C 0.3997(6) 0.49432(14) 0.2418(3) 0.0395(9) Uani 1 1 d . . .
C6 C 0.4616(7) 0.68865(16) 0.7599(3) 0.0471(10) Uani 1 1 d . . .
H6 H 0.3402 0.7026 0.7742 0.057 Uiso 1 1 calc R . .
C10 C 0.5697(7) 0.52441(15) 0.2837(3) 0.0443(10) Uani 1 1 d . . .
H10 H 0.6853 0.5240 0.2530 0.053 Uiso 1 1 calc R . .
C14 C 0.3971(7) 0.46230(15) 0.1474(3) 0.0440(10) Uani 1 1 d . . .
C16 C 0.2224(8) 0.44761(17) 0.0758(3) 0.0510(11) Uani 1 1 d . . .
H16 H 0.0960 0.4583 0.0903 0.061 Uiso 1 1 calc R . .
C13 C 0.2364(6) 0.52447(14) 0.3778(3) 0.0411(9) Uani 1 1 d . . .
H13 H 0.1230 0.5241 0.4101 0.049 Uiso 1 1 calc R . .
C1 C 0.6601(7) 0.70314(16) 0.8216(3) 0.0479(10) Uani 1 1 d . . .
C12 C 0.2300(7) 0.49495(15) 0.2895(3) 0.0423(9) Uani 1 1 d . . .
H12 H 0.1111 0.4752 0.2613 0.051 Uiso 1 1 calc R . .
C9 C 0.5742(7) 0.55517(15) 0.3696(3) 0.0458(10) Uani 1 1 d . . .
H9 H 0.6892 0.5765 0.3948 0.055 Uiso 1 1 calc R . .
C2 C 0.8413(7) 0.68018(18) 0.7996(4) 0.0535(11) Uani 1 1 d . . .
H2 H 0.9759 0.6888 0.8404 0.064 Uiso 1 1 calc R . .
C3 C 0.8202(6) 0.64601(16) 0.7202(3) 0.0476(10) Uani 1 1 d . . .
H3 H 0.9412 0.6311 0.7075 0.057 Uiso 1 1 calc R . .
C17 C 0.1974(8) 0.41797(18) -0.0202(3) 0.0578(12) Uani 1 1 d . . .
C20 C 0.0012(9) 0.41274(18) -0.0987(3) 0.0584(12) Uani 1 1 d . . .
H20 H -0.1266 0.4267 -0.0926 0.070 Uiso 1 1 calc R . .
C15 C 0.5986(8) 0.4478(2) 0.1341(4) 0.0614(13) Uani 1 1 d . . .
C21 C 0.8878(9) 0.76074(19) 0.9514(4) 0.0670(14) Uani 1 1 d . . .
H21A H 0.8639 0.7954 0.9692 0.080 Uiso 1 1 calc R . .
H21B H 0.9750 0.7611 0.8999 0.080 Uiso 1 1 calc R . .
C23 C 0.4999(9) 0.75851(19) 0.9318(4) 0.0692(15) Uani 1 1 d . . .
H23A H 0.5430 0.7695 1.0063 0.083 Uiso 1 1 calc R . .
H23B H 0.3938 0.7324 0.9270 0.083 Uiso 1 1 calc R . .
C18 C 0.2194(15) 0.3681(3) -0.1745(5) 0.094(2) Uani 1 1 d . . .
H18 H 0.2583 0.3479 -0.2258 0.113 Uiso 1 1 calc R . .
C22 C 1.0044(13) 0.7346(3) 1.0501(5) 0.099(2) Uani 1 1 d . . .
H22A H 0.9209 0.7349 1.1024 0.149 Uiso 1 1 calc R . .
H22B H 1.1368 0.7515 1.0791 0.149 Uiso 1 1 calc R . .
H22C H 1.0313 0.7003 1.0329 0.149 Uiso 1 1 calc R . .
C24 C 0.4049(12) 0.8011(2) 0.8641(6) 0.093(2) Uani 1 1 d . . .
H24A H 0.5099 0.8269 0.8673 0.139 Uiso 1 1 calc R . .
H24B H 0.2890 0.8144 0.8898 0.139 Uiso 1 1 calc R . .
H24C H 0.3536 0.7900 0.7910 0.139 Uiso 1 1 calc R . .
C19 C 0.0252(15) 0.3846(3) -0.1839(5) 0.096(2) Uani 1 1 d . . .
H19 H -0.0860 0.3778 -0.2435 0.115 Uiso 1 1 calc R . .
N2 N 0.4149(5) 0.58538(11) 0.5110(2) 0.0362(7) Uani 1 1 d . . .
N1 N 0.6831(7) 0.73748(15) 0.9009(3) 0.0593(11) Uani 1 1 d . . .
N3 N 0.7597(8) 0.4359(3) 0.1259(5) 0.115(2) Uani 1 1 d . . .
O1 O 0.2515(5) 0.64350(11) 0.6178(2) 0.0519(8) Uani 1 1 d . . .
F2 F 0.0641(4) 0.61989(9) 0.45100(19) 0.0529(7) Uani 1 1 d . . .
F1 F 0.1206(4) 0.56340(9) 0.5839(2) 0.0582(8) Uani 1 1 d . . .
B1 B 0.2053(7) 0.60289(17) 0.5410(4) 0.0403(10) 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
S1 C18 1.657(7) . ?
S1 C17 1.683(5) . ?
C8 C13 1.372(6) . ?
C8 C9 1.375(5) . ?
C8 N2 1.424(5) . ?
C5 O1 1.325(5) . ?
C5 C6 1.357(5) . ?
C5 C4 1.398(5) . ?
C7 N2 1.297(5) . ?
C7 C4 1.382(5) . ?
C7 H7 0.9300 . ?
C4 C3 1.395(6) . ?
C11 C10 1.361(6) . ?
C11 C12 1.387(5) . ?
C11 C14 1.473(5) . ?
C6 C1 1.390(6) . ?
C6 H6 0.9300 . ?
C10 C9 1.364(5) . ?
C10 H10 0.9300 . ?
C14 C16 1.330(6) . ?
C14 C15 1.415(6) . ?
C16 C17 1.434(6) . ?
C16 H16 0.9300 . ?
C13 C12 1.367(5) . ?
C13 H13 0.9300 . ?
C1 N1 1.344(5) . ?
C1 C2 1.415(6) . ?
C12 H12 0.9300 . ?
C9 H9 0.9300 . ?
C2 C3 1.344(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C17 C20 1.422(7) . ?
C20 C19 1.362(8) . ?
C20 H20 0.9300 . ?
C15 N3 1.123(7) . ?
C21 N1 1.464(7) . ?
C21 C22 1.477(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23 N1 1.455(6) . ?
C23 C24 1.465(9) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C18 C19 1.314(11) . ?
C18 H18 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C19 H19 0.9300 . ?
N2 B1 1.574(5) . ?
O1 B1 1.439(5) . ?
F2 B1 1.360(5) . ?
F1 B1 1.361(5) . ?

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
C18 S1 C17 92.4(4) . . ?
C13 C8 C9 119.0(3) . . ?
C13 C8 N2 120.4(3) . . ?
C9 C8 N2 120.6(4) . . ?
O1 C5 C6 119.8(3) . . ?
O1 C5 C4 119.3(3) . . ?
C6 C5 C4 120.9(4) . . ?
N2 C7 C4 123.7(3) . . ?
N2 C7 H7 118.1 . . ?
C4 C7 H7 118.1 . . ?
C7 C4 C5 119.7(4) . . ?
C7 C4 C3 122.4(3) . . ?
C5 C4 C3 117.9(3) . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 C14 120.4(3) . . ?
C12 C11 C14 121.2(4) . . ?
C5 C6 C1 121.1(4) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C16 C14 C15 119.7(4) . . ?
C16 C14 C11 124.7(4) . . ?
C15 C14 C11 115.5(4) . . ?
C14 C16 C17 130.4(4) . . ?
C14 C16 H16 114.8 . . ?
C17 C16 H16 114.8 . . ?
C8 C13 C12 120.5(3) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N1 C1 C6 122.1(4) . . ?
N1 C1 C2 119.9(4) . . ?
C6 C1 C2 118.0(4) . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C20 C17 C16 123.4(5) . . ?
C20 C17 S1 109.3(3) . . ?
C16 C17 S1 127.2(4) . . ?
C19 C20 C17 111.0(6) . . ?
C19 C20 H20 124.5 . . ?
C17 C20 H20 124.5 . . ?
N3 C15 C14 178.5(7) . . ?
N1 C21 C22 113.5(5) . . ?
N1 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N1 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
N1 C23 C24 112.9(5) . . ?
N1 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
N1 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C19 C18 S1 113.2(5) . . ?
C19 C18 H18 123.4 . . ?
S1 C18 H18 123.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C19 C20 114.0(6) . . ?
C18 C19 H19 123.0 . . ?
C20 C19 H19 123.0 . . ?
C7 N2 C8 119.0(3) . . ?
C7 N2 B1 119.6(3) . . ?
C8 N2 B1 121.4(3) . . ?
C1 N1 C23 121.3(4) . . ?
C1 N1 C21 122.6(4) . . ?
C23 N1 C21 115.7(4) . . ?
C5 O1 B1 125.2(3) . . ?
F1 B1 F2 110.0(4) . . ?
F1 B1 O1 109.8(3) . . ?
F2 B1 O1 108.3(3) . . ?
F1 B1 N2 109.4(3) . . ?
F2 B1 N2 109.6(3) . . ?
O1 B1 N2 109.9(3) . . ?

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
N2 C7 C4 C5 -2.2(6) . . . . ?
N2 C7 C4 C3 179.4(4) . . . . ?
O1 C5 C4 C7 -0.5(6) . . . . ?
C6 C5 C4 C7 -177.8(4) . . . . ?
O1 C5 C4 C3 178.1(4) . . . . ?
C6 C5 C4 C3 0.7(6) . . . . ?
O1 C5 C6 C1 -176.4(4) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C12 C11 C10 C9 -0.9(6) . . . . ?
C14 C11 C10 C9 178.6(4) . . . . ?
C10 C11 C14 C16 -152.3(4) . . . . ?
C12 C11 C14 C16 27.2(6) . . . . ?
C10 C11 C14 C15 26.6(6) . . . . ?
C12 C11 C14 C15 -154.0(4) . . . . ?
C15 C14 C16 C17 -0.7(8) . . . . ?
C11 C14 C16 C17 178.1(4) . . . . ?
C9 C8 C13 C12 0.8(6) . . . . ?
N2 C8 C13 C12 179.9(4) . . . . ?
C5 C6 C1 N1 178.8(4) . . . . ?
C5 C6 C1 C2 -1.8(6) . . . . ?
C8 C13 C12 C11 1.3(6) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
C14 C11 C12 C13 179.3(4) . . . . ?
C11 C10 C9 C8 2.9(7) . . . . ?
C13 C8 C9 C10 -2.8(6) . . . . ?
N2 C8 C9 C10 178.0(4) . . . . ?
N1 C1 C2 C3 -179.6(4) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C7 C4 C3 C2 177.0(4) . . . . ?
C5 C4 C3 C2 -1.6(6) . . . . ?
C14 C16 C17 C20 -168.6(5) . . . . ?
C14 C16 C17 S1 8.2(8) . . . . ?
C18 S1 C17 C20 -0.3(4) . . . . ?
C18 S1 C17 C16 -177.5(5) . . . . ?
C16 C17 C20 C19 177.0(5) . . . . ?
S1 C17 C20 C19 -0.4(5) . . . . ?
C16 C14 C15 N3 -127(23) . . . . ?
C11 C14 C15 N3 54(23) . . . . ?
C17 S1 C18 C19 0.9(6) . . . . ?
S1 C18 C19 C20 -1.3(8) . . . . ?
C17 C20 C19 C18 1.1(8) . . . . ?
C4 C7 N2 C8 174.0(3) . . . . ?
C4 C7 N2 B1 -6.1(5) . . . . ?
C13 C8 N2 C7 155.7(4) . . . . ?
C9 C8 N2 C7 -25.2(5) . . . . ?
C13 C8 N2 B1 -24.2(5) . . . . ?
C9 C8 N2 B1 154.9(4) . . . . ?
C6 C1 N1 C23 4.9(7) . . . . ?
C2 C1 N1 C23 -174.5(4) . . . . ?
C6 C1 N1 C21 -167.1(4) . . . . ?
C2 C1 N1 C21 13.5(7) . . . . ?
C24 C23 N1 C1 -84.4(6) . . . . ?
C24 C23 N1 C21 88.1(6) . . . . ?
C22 C21 N1 C1 -93.7(6) . . . . ?
C22 C21 N1 C23 93.9(6) . . . . ?
C6 C5 O1 B1 -169.9(4) . . . . ?
C4 C5 O1 B1 12.7(6) . . . . ?
C5 O1 B1 F1 101.2(4) . . . . ?
C5 O1 B1 F2 -138.8(4) . . . . ?
C5 O1 B1 N2 -19.1(5) . . . . ?
C7 N2 B1 F1 -105.1(4) . . . . ?
C8 N2 B1 F1 74.7(4) . . . . ?
C7 N2 B1 F2 134.2(4) . . . . ?
C8 N2 B1 F2 -45.9(5) . . . . ?
C7 N2 B1 O1 15.4(5) . . . . ?
C8 N2 B1 O1 -164.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.088
