# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1417241'
_audit_update_record             
;
2015-08-06 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
N-(4-fluoro-3-oxoisochroman-4-yl)-N-(phenylsulfonyl)benzenesulfonamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 F N O6 S2'
_chemical_formula_weight         461.47

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.045(2)
_cell_length_b                   12.916(3)
_cell_length_c                   14.840(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.48(3)
_cell_angle_gamma                90.00
_cell_volume                     1970.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4414
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9098
_exptl_absorpt_correction_T_max  0.9098
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15330
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4414
_reflns_number_gt                2778
_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)+(0.0681P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4414
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C1 C -0.1085(3) 0.4010(2) 0.3681(3) 0.0603(9) Uani 1 1 d . . .
H1A H -0.1526 0.4542 0.3906 0.072 Uiso 1 1 calc R . .
H1B H -0.1645 0.3814 0.3031 0.072 Uiso 1 1 calc R . .
C2 C 0.0164(3) 0.4427(2) 0.3664(2) 0.0480(7) Uani 1 1 d . . .
C3 C 0.0486(3) 0.5469(2) 0.3759(2) 0.0588(8) Uani 1 1 d . . .
H3B H -0.0120 0.5954 0.3788 0.071 Uiso 1 1 calc R . .
C4 C 0.1688(3) 0.5789(3) 0.3810(2) 0.0602(8) Uani 1 1 d . . .
H4B H 0.1884 0.6491 0.3845 0.072 Uiso 1 1 calc R . .
C5 C 0.2616(3) 0.5064(2) 0.3810(2) 0.0606(8) Uani 1 1 d . . .
H5B H 0.3445 0.5281 0.3870 0.073 Uiso 1 1 calc R . .
C6 C 0.2315(3) 0.4018(2) 0.3722(2) 0.0521(8) Uani 1 1 d . . .
H6A H 0.2942 0.3531 0.3735 0.062 Uiso 1 1 calc R . .
C7 C 0.1073(3) 0.3710(2) 0.3613(2) 0.0436(7) Uani 1 1 d . . .
C8 C 0.0614(3) 0.2586(2) 0.3479(2) 0.0447(7) Uani 1 1 d . . .
C9 C -0.0046(3) 0.2387(3) 0.4231(2) 0.0547(8) Uani 1 1 d . . .
C10 C -0.0266(3) 0.3981(2) 0.1259(2) 0.0483(7) Uani 1 1 d . . .
C11 C -0.1601(3) 0.4133(2) 0.0859(2) 0.0561(8) Uani 1 1 d . . .
H11A H -0.2173 0.3582 0.0780 0.067 Uiso 1 1 calc R . .
C12 C -0.2063(4) 0.5129(3) 0.0579(3) 0.0689(9) Uani 1 1 d . . .
H12A H -0.2954 0.5255 0.0319 0.083 Uiso 1 1 calc R . .
C13 C -0.1194(4) 0.5929(3) 0.0690(3) 0.0722(11) Uani 1 1 d . . .
H13A H -0.1508 0.6595 0.0506 0.087 Uiso 1 1 calc R . .
C14 C 0.0125(4) 0.5764(3) 0.1066(3) 0.0669(10) Uani 1 1 d . . .
H14A H 0.0694 0.6312 0.1123 0.080 Uiso 1 1 calc R . .
C15 C 0.0607(3) 0.4784(2) 0.1361(2) 0.0552(8) Uani 1 1 d . . .
H15A H 0.1499 0.4665 0.1622 0.066 Uiso 1 1 calc R . .
C16 C -0.0839(3) 0.0255(2) 0.2227(2) 0.0485(7) Uani 1 1 d . . .
C17 C -0.0891(3) -0.0198(2) 0.1372(2) 0.0524(8) Uani 1 1 d . . .
H17A H -0.1203 0.0167 0.0792 0.063 Uiso 1 1 calc R . .
C18 C -0.0471(3) -0.1207(2) 0.1398(3) 0.0577(8) Uani 1 1 d . . .
H18A H -0.0486 -0.1523 0.0831 0.069 Uiso 1 1 calc R . .
C19 C -0.0031(3) -0.1745(3) 0.2248(3) 0.0695(10) Uani 1 1 d . . .
H19A H 0.0220 -0.2432 0.2251 0.083 Uiso 1 1 calc R . .
C20 C 0.0045(4) -0.1281(3) 0.3102(3) 0.0780(11) Uani 1 1 d . . .
H20A H 0.0380 -0.1644 0.3683 0.094 Uiso 1 1 calc R . .
C21 C -0.0380(3) -0.0277(2) 0.3092(2) 0.0668(9) Uani 1 1 d . . .
H21A H -0.0356 0.0038 0.3661 0.080 Uiso 1 1 calc R . .
O1 O -0.0849(2) 0.31206(18) 0.43116(17) 0.0659(6) Uani 1 1 d . . .
O2 O 0.0253(2) 0.16650(19) 0.47744(17) 0.0722(7) Uani 1 1 d . . .
O3 O 0.17185(19) 0.27416(16) 0.20061(16) 0.0581(6) Uani 1 1 d . . .
O4 O -0.0253(2) 0.20335(15) 0.07881(15) 0.0612(6) Uani 1 1 d . . .
O5 O -0.2377(2) 0.17266(16) 0.12396(16) 0.0621(6) Uani 1 1 d . . .
O6 O -0.1945(2) 0.15893(16) 0.29802(16) 0.0587(6) Uani 1 1 d . . .
N1 N -0.0235(2) 0.23699(17) 0.24680(16) 0.0439(6) Uani 1 1 d . . .
S1 S 0.03428(8) 0.27175(6) 0.15748(6) 0.0485(2) Uani 1 1 d . . .
S2 S -0.15013(7) 0.15013(6) 0.21960(6) 0.0489(2) Uani 1 1 d . . .
F1 F 0.16535(16) 0.19177(13) 0.37332(13) 0.0588(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.444(4) . ?
C1 C2 1.490(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.387(4) . ?
C2 C7 1.388(4) . ?
C3 C4 1.365(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4B 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5B 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.526(4) . ?
C8 F1 1.375(3) . ?
C8 N1 1.476(4) . ?
C8 C9 1.561(4) . ?
C9 O2 1.198(4) . ?
C9 O1 1.332(4) . ?
C10 C15 1.386(4) . ?
C10 C11 1.387(4) . ?
C10 S1 1.761(3) . ?
C11 C12 1.391(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.379(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.373(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.380(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C21 1.379(4) . ?
C16 C17 1.379(4) . ?
C16 S2 1.761(3) . ?
C17 C18 1.379(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.365(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.376(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.377(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
O3 S1 1.417(2) . ?
O4 S1 1.419(2) . ?
O5 S2 1.425(2) . ?
O6 S2 1.423(2) . ?
N1 S2 1.722(2) . ?
N1 S1 1.728(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 C2 110.5(2) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C7 119.3(3) . . ?
C3 C2 C1 123.7(3) . . ?
C7 C2 C1 116.9(3) . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3B 119.7 . . ?
C2 C3 H3B 119.7 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4B 120.0 . . ?
C5 C4 H4B 120.0 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5B 119.8 . . ?
C4 C5 H5B 119.8 . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
C6 C7 C2 120.6(3) . . ?
C6 C7 C8 123.9(2) . . ?
C2 C7 C8 115.4(2) . . ?
F1 C8 N1 108.4(2) . . ?
F1 C8 C7 110.9(2) . . ?
N1 C8 C7 111.7(2) . . ?
F1 C8 C9 105.2(2) . . ?
N1 C8 C9 114.0(2) . . ?
C7 C8 C9 106.5(2) . . ?
O2 C9 O1 121.4(3) . . ?
O2 C9 C8 121.6(3) . . ?
O1 C9 C8 116.6(3) . . ?
C15 C10 C11 121.9(3) . . ?
C15 C10 S1 118.8(3) . . ?
C11 C10 S1 119.2(2) . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 H11A 120.8 . . ?
C12 C11 H11A 120.8 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C10 118.7(3) . . ?
C14 C15 H15A 120.7 . . ?
C10 C15 H15A 120.7 . . ?
C21 C16 C17 121.4(3) . . ?
C21 C16 S2 119.2(2) . . ?
C17 C16 S2 119.2(2) . . ?
C18 C17 C16 118.4(3) . . ?
C18 C17 H17A 120.8 . . ?
C16 C17 H17A 120.8 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C19 C20 120.7(3) . . ?
C18 C19 H19A 119.6 . . ?
C20 C19 H19A 119.6 . . ?
C19 C20 C21 119.6(3) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C20 C21 C16 119.2(3) . . ?
C20 C21 H21A 120.4 . . ?
C16 C21 H21A 120.4 . . ?
C9 O1 C1 118.4(2) . . ?
C8 N1 S2 121.39(18) . . ?
C8 N1 S1 117.08(18) . . ?
S2 N1 S1 119.07(13) . . ?
O3 S1 O4 118.89(13) . . ?
O3 S1 N1 107.18(12) . . ?
O4 S1 N1 106.20(12) . . ?
O3 S1 C10 109.96(14) . . ?
O4 S1 C10 109.94(14) . . ?
N1 S1 C10 103.44(12) . . ?
O6 S2 O5 119.17(14) . . ?
O6 S2 N1 104.44(12) . . ?
O5 S2 N1 107.30(12) . . ?
O6 S2 C16 108.40(14) . . ?
O5 S2 C16 109.67(14) . . ?
N1 S2 C16 107.17(13) . . ?

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 -133.2(3) . . . . ?
O1 C1 C2 C7 42.4(4) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C4 175.0(3) . . . . ?
C2 C3 C4 C5 -2.8(5) . . . . ?
C3 C4 C5 C6 2.4(5) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C5 C6 C7 C2 -4.7(4) . . . . ?
C5 C6 C7 C8 178.1(3) . . . . ?
C3 C2 C7 C6 4.4(4) . . . . ?
C1 C2 C7 C6 -171.5(3) . . . . ?
C3 C2 C7 C8 -178.3(3) . . . . ?
C1 C2 C7 C8 5.9(4) . . . . ?
C6 C7 C8 F1 16.0(4) . . . . ?
C2 C7 C8 F1 -161.3(2) . . . . ?
C6 C7 C8 N1 -105.1(3) . . . . ?
C2 C7 C8 N1 77.6(3) . . . . ?
C6 C7 C8 C9 129.9(3) . . . . ?
C2 C7 C8 C9 -47.4(3) . . . . ?
F1 C8 C9 O2 -10.6(4) . . . . ?
N1 C8 C9 O2 108.0(3) . . . . ?
C7 C8 C9 O2 -128.4(3) . . . . ?
F1 C8 C9 O1 162.1(2) . . . . ?
N1 C8 C9 O1 -79.3(3) . . . . ?
C7 C8 C9 O1 44.3(3) . . . . ?
C15 C10 C11 C12 -1.8(5) . . . . ?
S1 C10 C11 C12 -177.5(2) . . . . ?
C10 C11 C12 C13 1.1(5) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C12 C13 C14 C15 -1.3(5) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
C11 C10 C15 C14 1.0(4) . . . . ?
S1 C10 C15 C14 176.7(2) . . . . ?
C21 C16 C17 C18 0.0(4) . . . . ?
S2 C16 C17 C18 -174.5(2) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C17 C18 C19 C20 -2.3(5) . . . . ?
C18 C19 C20 C21 2.8(6) . . . . ?
C19 C20 C21 C16 -1.8(6) . . . . ?
C17 C16 C21 C20 0.5(5) . . . . ?
S2 C16 C21 C20 175.0(3) . . . . ?
O2 C9 O1 C1 175.1(3) . . . . ?
C8 C9 O1 C1 2.5(4) . . . . ?
C2 C1 O1 C9 -47.1(4) . . . . ?
F1 C8 N1 S2 91.1(2) . . . . ?
C7 C8 N1 S2 -146.36(19) . . . . ?
C9 C8 N1 S2 -25.7(3) . . . . ?
F1 C8 N1 S1 -70.9(2) . . . . ?
C7 C8 N1 S1 51.6(3) . . . . ?
C9 C8 N1 S1 172.31(19) . . . . ?
C8 N1 S1 O3 24.4(2) . . . . ?
S2 N1 S1 O3 -138.10(14) . . . . ?
C8 N1 S1 O4 152.43(19) . . . . ?
S2 N1 S1 O4 -10.05(19) . . . . ?
C8 N1 S1 C10 -91.8(2) . . . . ?
S2 N1 S1 C10 105.72(17) . . . . ?
C15 C10 S1 O3 6.6(3) . . . . ?
C11 C10 S1 O3 -177.5(2) . . . . ?
C15 C10 S1 O4 -126.1(2) . . . . ?
C11 C10 S1 O4 49.7(3) . . . . ?
C15 C10 S1 N1 120.8(2) . . . . ?
C11 C10 S1 N1 -63.3(3) . . . . ?
C8 N1 S2 O6 32.7(2) . . . . ?
S1 N1 S2 O6 -165.65(14) . . . . ?
C8 N1 S2 O5 160.1(2) . . . . ?
S1 N1 S2 O5 -38.25(18) . . . . ?
C8 N1 S2 C16 -82.2(2) . . . . ?
S1 N1 S2 C16 79.47(18) . . . . ?
C21 C16 S2 O6 -24.1(3) . . . . ?
C17 C16 S2 O6 150.5(2) . . . . ?
C21 C16 S2 O5 -155.7(3) . . . . ?
C17 C16 S2 O5 18.9(3) . . . . ?
C21 C16 S2 N1 88.1(3) . . . . ?
C17 C16 S2 N1 -97.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.055
