# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_z
_database_code_depnum_ccdc_archive 'CCDC 1439365'
_audit_update_record             
;
2015-11-28 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 F N O5 S'
_chemical_formula_weight         389.39

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   10.342(2)
_cell_length_b                   12.672(3)
_cell_length_c                   13.549(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1775.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9040
_exptl_absorpt_correction_T_max  0.9441
_exptl_absorpt_process_details   sadabs

_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  'Bruker Smart Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20679
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3128
_reflns_number_gt                2973
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.3396P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3128
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.92042(5) 0.94071(4) 0.07628(4) 0.04166(13) Uani 1 1 d . . .
O1 O 0.98244(17) 0.87467(12) 0.00526(14) 0.0663(5) Uani 1 1 d . . .
O2 O 0.96270(16) 0.93116(14) 0.17623(12) 0.0647(5) Uani 1 1 d . . .
O3 O 0.77612(13) 1.18653(10) 0.17687(9) 0.0388(3) Uani 1 1 d . . .
O4 O 0.81904(14) 1.29977(10) 0.05369(9) 0.0431(3) Uani 1 1 d . . .
O5 O 1.01996(13) 1.19824(12) -0.10928(11) 0.0509(4) Uani 1 1 d . . .
N1 N 0.92730(15) 1.06379(12) 0.03904(11) 0.0378(3) Uani 1 1 d . . .
H1A H 0.9993 1.0969 0.0322 0.045 Uiso 1 1 calc R . .
F1 F 0.80588(12) 1.05378(8) -0.14646(8) 0.0460(3) Uani 1 1 d . . .
C1 C 0.75167(17) 0.93488(14) 0.07067(13) 0.0360(4) Uani 1 1 d . . .
C2 C 0.6766(2) 0.84742(15) 0.09266(14) 0.0465(5) Uani 1 1 d . . .
H2A H 0.7144 0.7840 0.1117 0.056 Uiso 1 1 calc R . .
C3 C 0.5449(2) 0.85716(17) 0.08556(16) 0.0504(5) Uani 1 1 d . . .
H3A H 0.4921 0.7995 0.0990 0.060 Uiso 1 1 calc R . .
C4 C 0.4902(2) 0.95273(18) 0.05839(16) 0.0497(5) Uani 1 1 d . . .
H4A H 0.4007 0.9585 0.0544 0.060 Uiso 1 1 calc R . .
C5 C 0.56611(19) 1.03971(15) 0.03701(14) 0.0410(4) Uani 1 1 d . . .
H5A H 0.5282 1.1035 0.0192 0.049 Uiso 1 1 calc R . .
C6 C 0.69943(18) 1.03042(13) 0.04254(12) 0.0332(4) Uani 1 1 d . . .
C7 C 0.80105(17) 1.11373(13) 0.01811(12) 0.0311(4) Uani 1 1 d . . .
C8 C 0.79315(17) 1.14674(13) -0.09159(12) 0.0328(4) Uani 1 1 d . . .
C9 C 0.67076(18) 1.20501(15) -0.12354(14) 0.0380(4) Uani 1 1 d . . .
H9A H 0.6134 1.1584 -0.1597 0.046 Uiso 1 1 calc R . .
H9B H 0.6250 1.2329 -0.0668 0.046 Uiso 1 1 calc R . .
C10 C 0.71873(19) 1.29323(14) -0.18889(13) 0.0368(4) Uani 1 1 d . . .
C11 C 0.6457(2) 1.36406(17) -0.24317(15) 0.0490(5) Uani 1 1 d . . .
H11A H 0.5559 1.3615 -0.2420 0.059 Uiso 1 1 calc R . .
C12 C 0.7103(3) 1.43898(18) -0.29932(16) 0.0582(6) Uani 1 1 d . . .
H12A H 0.6627 1.4869 -0.3365 0.070 Uiso 1 1 calc R . .
C13 C 0.8438(3) 1.44402(17) -0.30124(16) 0.0561(6) Uani 1 1 d . . .
H13A H 0.8844 1.4948 -0.3399 0.067 Uiso 1 1 calc R . .
C14 C 0.9176(2) 1.37469(16) -0.24660(14) 0.0460(5) Uani 1 1 d . . .
H14A H 1.0074 1.3780 -0.2473 0.055 Uiso 1 1 calc R . .
C15 C 0.85235(18) 1.29938(14) -0.19023(13) 0.0366(4) Uani 1 1 d . . .
C16 C 0.90678(18) 1.21680(14) -0.12795(13) 0.0356(4) Uani 1 1 d . . .
C17 C 0.79702(16) 1.21239(13) 0.08398(13) 0.0311(4) Uani 1 1 d . . .
C18 C 0.7855(2) 1.27158(15) 0.24944(14) 0.0447(4) Uani 1 1 d . . .
H18A H 0.7122 1.3190 0.2432 0.054 Uiso 1 1 calc R . .
H18B H 0.8642 1.3118 0.2392 0.054 Uiso 1 1 calc R . .
C19 C 0.7865(2) 1.22159(19) 0.34941(15) 0.0556(6) Uani 1 1 d . . .
H19B H 0.7923 1.2755 0.3990 0.083 Uiso 1 1 calc R . .
H19C H 0.8595 1.1752 0.3548 0.083 Uiso 1 1 calc R . .
H19D H 0.7082 1.1820 0.3586 0.083 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 O1 1.4275(17) . ?
S1 O2 1.4282(16) . ?
S1 N1 1.6408(16) . ?
S1 C1 1.7484(19) . ?
O3 C17 1.318(2) . ?
O3 C18 1.462(2) . ?
O4 C17 1.203(2) . ?
O5 C16 1.220(2) . ?
N1 C7 1.478(2) . ?
N1 H1A 0.8600 . ?
F1 C8 1.399(2) . ?
C1 C6 1.379(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.371(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.526(2) . ?
C7 C17 1.537(2) . ?
C7 C8 1.546(2) . ?
C8 C9 1.528(3) . ?
C8 C16 1.553(2) . ?
C9 C10 1.510(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.384(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.388(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.383(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.379(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.396(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.457(3) . ?
C18 C19 1.495(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19D 0.9600 . ?

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 116.87(11) . . ?
O1 S1 N1 109.30(10) . . ?
O2 S1 N1 111.03(10) . . ?
O1 S1 C1 113.23(10) . . ?
O2 S1 C1 110.08(10) . . ?
N1 S1 C1 94.02(9) . . ?
C17 O3 C18 116.61(14) . . ?
C7 N1 S1 115.31(12) . . ?
C7 N1 H1A 122.3 . . ?
S1 N1 H1A 122.3 . . ?
C6 C1 C2 122.82(18) . . ?
C6 C1 S1 111.46(14) . . ?
C2 C1 S1 125.71(15) . . ?
C3 C2 C1 118.00(18) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 120.16(19) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 119.04(19) . . ?
C4 C5 H5A 120.5 . . ?
C6 C5 H5A 120.5 . . ?
C1 C6 C5 118.63(16) . . ?
C1 C6 C7 113.42(16) . . ?
C5 C6 C7 127.93(17) . . ?
N1 C7 C6 105.69(13) . . ?
N1 C7 C17 105.12(13) . . ?
C6 C7 C17 114.73(14) . . ?
N1 C7 C8 110.29(14) . . ?
C6 C7 C8 111.05(14) . . ?
C17 C7 C8 109.67(14) . . ?
F1 C8 C9 109.53(14) . . ?
F1 C8 C7 106.14(13) . . ?
C9 C8 C7 116.54(14) . . ?
F1 C8 C16 103.98(13) . . ?
C9 C8 C16 105.11(14) . . ?
C7 C8 C16 114.82(15) . . ?
C10 C9 C8 104.58(15) . . ?
C10 C9 H9A 110.8 . . ?
C8 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C15 C10 C11 120.07(18) . . ?
C15 C10 C9 112.17(16) . . ?
C11 C10 C9 127.76(18) . . ?
C10 C11 C12 118.2(2) . . ?
C10 C11 H11A 120.9 . . ?
C12 C11 H11A 120.9 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12A 119.3 . . ?
C11 C12 H12A 119.3 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 117.5(2) . . ?
C13 C14 H14A 121.2 . . ?
C15 C14 H14A 121.2 . . ?
C10 C15 C14 121.87(19) . . ?
C10 C15 C16 109.73(16) . . ?
C14 C15 C16 128.38(19) . . ?
O5 C16 C15 128.96(17) . . ?
O5 C16 C8 123.35(16) . . ?
C15 C16 C8 107.58(15) . . ?
O4 C17 O3 125.85(16) . . ?
O4 C17 C7 123.08(16) . . ?
O3 C17 C7 110.89(14) . . ?
O3 C18 C19 107.29(17) . . ?
O3 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O3 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C19 H19D 109.5 . . ?
H19B C19 H19D 109.5 . . ?
H19C C19 H19D 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 S1 N1 C7 116.24(14) . . . . ?
O2 S1 N1 C7 -113.40(14) . . . . ?
C1 S1 N1 C7 -0.09(13) . . . . ?
O1 S1 C1 C6 -114.89(15) . . . . ?
O2 S1 C1 C6 112.23(14) . . . . ?
N1 S1 C1 C6 -1.90(14) . . . . ?
O1 S1 C1 C2 66.09(19) . . . . ?
O2 S1 C1 C2 -66.79(19) . . . . ?
N1 S1 C1 C2 179.09(17) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
S1 C1 C2 C3 179.14(16) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
S1 C1 C6 C5 -178.36(14) . . . . ?
C2 C1 C6 C7 -177.67(16) . . . . ?
S1 C1 C6 C7 3.28(18) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 C7 177.14(17) . . . . ?
S1 N1 C7 C6 1.79(17) . . . . ?
S1 N1 C7 C17 123.53(13) . . . . ?
S1 N1 C7 C8 -118.32(13) . . . . ?
C1 C6 C7 N1 -3.20(19) . . . . ?
C5 C6 C7 N1 178.63(17) . . . . ?
C1 C6 C7 C17 -118.52(17) . . . . ?
C5 C6 C7 C17 63.3(2) . . . . ?
C1 C6 C7 C8 116.42(16) . . . . ?
C5 C6 C7 C8 -61.8(2) . . . . ?
N1 C7 C8 F1 60.91(17) . . . . ?
C6 C7 C8 F1 -55.92(17) . . . . ?
C17 C7 C8 F1 176.23(13) . . . . ?
N1 C7 C8 C9 -176.84(14) . . . . ?
C6 C7 C8 C9 66.32(19) . . . . ?
C17 C7 C8 C9 -61.53(19) . . . . ?
N1 C7 C8 C16 -53.34(19) . . . . ?
C6 C7 C8 C16 -170.17(14) . . . . ?
C17 C7 C8 C16 61.97(18) . . . . ?
F1 C8 C9 C10 -102.46(16) . . . . ?
C7 C8 C9 C10 137.09(15) . . . . ?
C16 C8 C9 C10 8.72(18) . . . . ?
C8 C9 C10 C15 -6.1(2) . . . . ?
C8 C9 C10 C11 174.37(18) . . . . ?
C15 C10 C11 C12 1.1(3) . . . . ?
C9 C10 C11 C12 -179.5(2) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C11 C10 C15 C14 -1.1(3) . . . . ?
C9 C10 C15 C14 179.40(17) . . . . ?
C11 C10 C15 C16 -179.88(17) . . . . ?
C9 C10 C15 C16 0.6(2) . . . . ?
C13 C14 C15 C10 0.3(3) . . . . ?
C13 C14 C15 C16 178.88(19) . . . . ?
C10 C15 C16 O5 -178.55(19) . . . . ?
C14 C15 C16 O5 2.8(3) . . . . ?
C10 C15 C16 C8 5.2(2) . . . . ?
C14 C15 C16 C8 -173.50(18) . . . . ?
F1 C8 C16 O5 -70.2(2) . . . . ?
C9 C8 C16 O5 174.75(18) . . . . ?
C7 C8 C16 O5 45.3(2) . . . . ?
F1 C8 C16 C15 106.35(15) . . . . ?
C9 C8 C16 C15 -8.74(18) . . . . ?
C7 C8 C16 C15 -138.14(15) . . . . ?
C18 O3 C17 O4 -2.4(3) . . . . ?
C18 O3 C17 C7 172.85(15) . . . . ?
N1 C7 C17 O4 100.68(19) . . . . ?
C6 C7 C17 O4 -143.66(17) . . . . ?
C8 C7 C17 O4 -17.9(2) . . . . ?
N1 C7 C17 O3 -74.72(16) . . . . ?
C6 C7 C17 O3 40.9(2) . . . . ?
C8 C7 C17 O3 166.72(14) . . . . ?
C17 O3 C18 C19 -168.24(17) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1439366'
_audit_update_record             
;
2015-11-28 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 F2 N2 O4 S'
_chemical_formula_weight         380.36

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'
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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.1956(3)
_cell_length_b                   9.6833(3)
_cell_length_c                   23.2873(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1622.59(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9049
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_process_details   sadabs

_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  'Bruker Smart Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18989
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2871
_reflns_number_gt                2733
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.6517P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.19522(8) 0.54507(5) 0.03045(2) 0.03442(14) Uani 1 1 d . . .
F1 F 0.3297(2) 0.5852(2) -0.14053(7) 0.0713(5) Uani 1 1 d . . .
F2 F 0.3229(3) 0.7570(2) -0.08190(7) 0.0943(8) Uani 1 1 d . . .
O1 O 0.3828(2) 0.59641(17) 0.03530(7) 0.0484(4) Uani 1 1 d . . .
O2 O 0.0989(3) 0.5282(2) 0.08309(7) 0.0538(5) Uani 1 1 d . . .
O3 O 0.0719(3) 0.89242(16) -0.13911(8) 0.0505(5) Uani 1 1 d . . .
H3B H 0.0164 0.8961 -0.1084 0.076 Uiso 1 1 calc R . .
O4 O -0.2518(2) 0.5587(2) -0.08562(8) 0.0640(6) Uani 1 1 d . . .
N1 N 0.0738(3) 0.63677(19) -0.01434(7) 0.0415(5) Uani 1 1 d . . .
H1A H 0.0106 0.7080 -0.0041 0.050 Uiso 1 1 calc R . .
N2 N -0.0828(3) 0.68022(18) -0.15166(7) 0.0332(4) Uani 1 1 d . . .
C1 C 0.1914(3) 0.3997(2) -0.01403(9) 0.0337(5) Uani 1 1 d . . .
C2 C 0.2386(3) 0.2658(3) 0.00120(13) 0.0484(6) Uani 1 1 d . . .
H2A H 0.2774 0.2438 0.0382 0.058 Uiso 1 1 calc R . .
C3 C 0.2251(4) 0.1669(3) -0.04111(16) 0.0616(8) Uani 1 1 d . . .
H3A H 0.2534 0.0755 -0.0326 0.074 Uiso 1 1 calc R . .
C4 C 0.1703(4) 0.2017(3) -0.09578(15) 0.0618(8) Uani 1 1 d . . .
H4A H 0.1649 0.1335 -0.1238 0.074 Uiso 1 1 calc R . .
C5 C 0.1233(4) 0.3354(3) -0.10996(12) 0.0500(6) Uani 1 1 d . . .
H5A H 0.0855 0.3573 -0.1470 0.060 Uiso 1 1 calc R . .
C6 C 0.1331(3) 0.4360(2) -0.06816(9) 0.0342(5) Uani 1 1 d . . .
C7 C 0.0815(3) 0.5879(2) -0.07326(9) 0.0307(5) Uani 1 1 d . . .
C8 C -0.1079(3) 0.6062(2) -0.10296(9) 0.0368(5) Uani 1 1 d . . .
C9 C 0.0930(3) 0.7543(2) -0.15557(9) 0.0316(4) Uani 1 1 d . . .
C10 C 0.2142(3) 0.6717(3) -0.11216(9) 0.0400(5) Uani 1 1 d . . .
C11 C 0.1790(3) 0.7551(2) -0.21491(9) 0.0332(5) Uani 1 1 d . . .
C12 C 0.3041(4) 0.8583(3) -0.22907(10) 0.0472(6) Uani 1 1 d . . .
H12A H 0.3270 0.9301 -0.2035 0.057 Uiso 1 1 calc R . .
C13 C 0.3953(4) 0.8542(3) -0.28155(13) 0.0644(8) Uani 1 1 d . . .
H13A H 0.4788 0.9237 -0.2912 0.077 Uiso 1 1 calc R . .
C14 C 0.3626(5) 0.7477(4) -0.31942(12) 0.0679(9) Uani 1 1 d . . .
H14A H 0.4243 0.7450 -0.3545 0.081 Uiso 1 1 calc R . .
C15 C 0.2393(4) 0.6461(4) -0.30520(11) 0.0640(8) Uani 1 1 d . . .
H15A H 0.2167 0.5747 -0.3310 0.077 Uiso 1 1 calc R . .
C16 C 0.1481(4) 0.6480(3) -0.25335(10) 0.0481(6) Uani 1 1 d . . .
H16A H 0.0657 0.5775 -0.2440 0.058 Uiso 1 1 calc R . .
C17 C -0.2431(4) 0.7242(3) -0.18590(11) 0.0467(6) Uani 1 1 d . . .
H17A H -0.3465 0.6642 -0.1783 0.070 Uiso 1 1 calc R . .
H17B H -0.2122 0.7198 -0.2260 0.070 Uiso 1 1 calc R . .
H17C H -0.2757 0.8173 -0.1759 0.070 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4176(18) . ?
S1 O1 1.4431(18) . ?
S1 N1 1.6247(19) . ?
S1 C1 1.748(2) . ?
F1 C10 1.352(3) . ?
F2 C10 1.338(3) . ?
O3 C9 1.399(3) . ?
O3 H3B 0.8200 . ?
O4 C8 1.203(3) . ?
N1 C7 1.453(3) . ?
N1 H1A 0.8600 . ?
N2 C8 1.353(3) . ?
N2 C9 1.457(3) . ?
N2 C17 1.466(3) . ?
C1 C6 1.374(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.377(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.522(3) . ?
C7 C8 1.539(3) . ?
C7 C10 1.546(3) . ?
C9 C11 1.514(3) . ?
C9 C10 1.556(3) . ?
C11 C12 1.384(3) . ?
C11 C16 1.388(3) . ?
C12 C13 1.388(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.377(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.366(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 115.41(11) . . ?
O2 S1 N1 110.81(11) . . ?
O1 S1 N1 111.41(11) . . ?
O2 S1 C1 114.34(11) . . ?
O1 S1 C1 109.79(10) . . ?
N1 S1 C1 92.93(10) . . ?
C9 O3 H3B 109.5 . . ?
C7 N1 S1 114.06(15) . . ?
C7 N1 H1A 123.0 . . ?
S1 N1 H1A 123.0 . . ?
C8 N2 C9 115.40(18) . . ?
C8 N2 C17 120.30(19) . . ?
C9 N2 C17 120.42(17) . . ?
C6 C1 C2 123.2(2) . . ?
C6 C1 S1 110.05(16) . . ?
C2 C1 S1 126.71(19) . . ?
C3 C2 C1 116.7(3) . . ?
C3 C2 H2A 121.6 . . ?
C1 C2 H2A 121.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 C7 113.14(18) . . ?
C5 C6 C7 128.0(2) . . ?
N1 C7 C6 104.53(17) . . ?
N1 C7 C8 110.69(18) . . ?
C6 C7 C8 111.29(18) . . ?
N1 C7 C10 113.94(18) . . ?
C6 C7 C10 113.72(18) . . ?
C8 C7 C10 102.87(17) . . ?
O4 C8 N2 126.8(2) . . ?
O4 C8 C7 124.56(19) . . ?
N2 C8 C7 108.65(19) . . ?
O3 C9 N2 111.05(18) . . ?
O3 C9 C11 106.82(17) . . ?
N2 C9 C11 114.49(17) . . ?
O3 C9 C10 111.98(19) . . ?
N2 C9 C10 101.10(16) . . ?
C11 C9 C10 111.49(18) . . ?
F2 C10 F1 106.3(2) . . ?
F2 C10 C7 112.11(18) . . ?
F1 C10 C7 109.93(19) . . ?
F2 C10 C9 110.6(2) . . ?
F1 C10 C9 110.21(17) . . ?
C7 C10 C9 107.72(18) . . ?
C12 C11 C16 119.3(2) . . ?
C12 C11 C9 119.1(2) . . ?
C16 C11 C9 121.3(2) . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 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
O2 S1 N1 C7 -139.92(17) . . . . ?
O1 S1 N1 C7 90.13(18) . . . . ?
C1 S1 N1 C7 -22.47(18) . . . . ?
O2 S1 C1 C6 128.45(17) . . . . ?
O1 S1 C1 C6 -99.99(17) . . . . ?
N1 S1 C1 C6 14.02(17) . . . . ?
O2 S1 C1 C2 -51.4(2) . . . . ?
O1 S1 C1 C2 80.1(2) . . . . ?
N1 S1 C1 C2 -165.9(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
S1 C1 C2 C3 180.00(19) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
S1 C1 C6 C5 179.09(18) . . . . ?
C2 C1 C6 C7 177.4(2) . . . . ?
S1 C1 C6 C7 -2.4(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -177.5(2) . . . . ?
S1 N1 C7 C6 23.3(2) . . . . ?
S1 N1 C7 C8 143.21(17) . . . . ?
S1 N1 C7 C10 -101.4(2) . . . . ?
C1 C6 C7 N1 -12.2(2) . . . . ?
C5 C6 C7 N1 166.1(2) . . . . ?
C1 C6 C7 C8 -131.67(19) . . . . ?
C5 C6 C7 C8 46.6(3) . . . . ?
C1 C6 C7 C10 112.7(2) . . . . ?
C5 C6 C7 C10 -69.0(3) . . . . ?
C9 N2 C8 O4 165.3(2) . . . . ?
C17 N2 C8 O4 7.4(4) . . . . ?
C9 N2 C8 C7 -16.4(3) . . . . ?
C17 N2 C8 C7 -174.4(2) . . . . ?
N1 C7 C8 O4 -56.5(3) . . . . ?
C6 C7 C8 O4 59.3(3) . . . . ?
C10 C7 C8 O4 -178.6(2) . . . . ?
N1 C7 C8 N2 125.20(19) . . . . ?
C6 C7 C8 N2 -119.0(2) . . . . ?
C10 C7 C8 N2 3.1(2) . . . . ?
C8 N2 C9 O3 -97.3(2) . . . . ?
C17 N2 C9 O3 60.5(3) . . . . ?
C8 N2 C9 C11 141.59(19) . . . . ?
C17 N2 C9 C11 -60.5(3) . . . . ?
C8 N2 C9 C10 21.6(2) . . . . ?
C17 N2 C9 C10 179.50(19) . . . . ?
N1 C7 C10 F2 11.7(3) . . . . ?
C6 C7 C10 F2 -108.0(2) . . . . ?
C8 C7 C10 F2 131.6(2) . . . . ?
N1 C7 C10 F1 129.66(19) . . . . ?
C6 C7 C10 F1 10.0(3) . . . . ?
C8 C7 C10 F1 -110.5(2) . . . . ?
N1 C7 C10 C9 -110.2(2) . . . . ?
C6 C7 C10 C9 130.11(19) . . . . ?
C8 C7 C10 C9 9.6(2) . . . . ?
O3 C9 C10 F2 -22.4(3) . . . . ?
N2 C9 C10 F2 -140.7(2) . . . . ?
C11 C9 C10 F2 97.2(2) . . . . ?
O3 C9 C10 F1 -139.62(19) . . . . ?
N2 C9 C10 F1 102.09(19) . . . . ?
C11 C9 C10 F1 -20.0(2) . . . . ?
O3 C9 C10 C7 100.4(2) . . . . ?
N2 C9 C10 C7 -17.8(2) . . . . ?
C11 C9 C10 C7 -139.93(18) . . . . ?
O3 C9 C11 C12 33.8(3) . . . . ?
N2 C9 C11 C12 157.2(2) . . . . ?
C10 C9 C11 C12 -88.8(2) . . . . ?
O3 C9 C11 C16 -152.1(2) . . . . ?
N2 C9 C11 C16 -28.7(3) . . . . ?
C10 C9 C11 C16 85.3(3) . . . . ?
C16 C11 C12 C13 0.7(4) . . . . ?
C9 C11 C12 C13 174.9(2) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C11 0.8(4) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
C9 C11 C16 C15 -175.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.037
