# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_3f
_database_code_depnum_ccdc_archive 'CCDC 1831373'
_audit_update_record             
;
2018-03-21 deposited with the CCDC.
2018-07-06 downloaded from the CCDC.
;
#============================================================================== 
_audit_creation_date             2018-03-21
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 014djd16
_chemical_name_systematic        .
_chemical_melting_point          'not measured'


_cell_length_a                   9.3819(2)
_cell_length_b                   10.3076(2)
_cell_length_c                   10.6318(3)
_cell_angle_alpha                90.7648(7)
_cell_angle_beta                 114.2115(9)
_cell_angle_gamma                100.1376(10)
_cell_volume                     918.87(4)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C22 H21 N1 O3 S1 
# Dc =      1.37 Fooo =    400.00 Mu =      1.99 M =    379.48
# Found Formula = C22 H21 N1 O3 S1 
# Dc =      1.37 FOOO =    400.00 Mu =      1.99 M =    379.48

_chemical_formula_sum            'C22 H21 N1 O3 S1'
_chemical_formula_moiety         'C22 H21 N1 O3 S1'
_chemical_compound_source        .
_chemical_formula_weight         379.48


_cell_measurement_reflns_used    3821
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.199

# Sheldrick geometric approximatio 0.96 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            14240
_reflns_number_total             4183
_diffrn_reflns_av_R_equivalents  0.019
# Number of reflections without Friedels Law is 7259 
# Number of reflections with Friedels Law is 4183 
# Theoretical number of reflections is about 4228 


_diffrn_reflns_theta_min         5.442
_diffrn_reflns_theta_max         27.515
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        26.690
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -12
_reflns_limit_h_max              10
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   1.97
_oxford_diffrn_Wilson_scale      0.69

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.29


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     4
_refine_ls_number_parameters     248
_oxford_refine_ls_R_factor_ref   0.0449
_refine_ls_wR_factor_ref         0.0982
_refine_ls_goodness_of_fit_ref   1.0045
_refine_ls_shift/su_max          0.0007955
_refine_ls_shift/su_mean         0.0000275


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4183
_refine_ls_R_factor_all          0.0449
_refine_ls_wR_factor_all         0.0982

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3634
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_gt          0.0923

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.39P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.03691(4) 0.74565(3) 0.26465(4) 0.0243 1.0000 Uani . . . . . .
O2 O 0.10321(12) 0.73935(10) 0.41235(10) 0.0319 1.0000 Uani . . . . . .
O3 O 0.14523(12) 0.78865(10) 0.20171(12) 0.0349 1.0000 Uani . . . . . .
C4 C -0.07760(15) 0.58399(12) 0.17541(14) 0.0233 1.0000 Uani . . . . . .
C5 C 0.03919(16) 0.48880(13) 0.20232(15) 0.0264 1.0000 Uani . . . . . .
C6 C 0.06604(16) 0.42335(13) 0.33601(15) 0.0268 1.0000 Uani D . . . . .
N7 N -0.08719(14) 0.35156(12) 0.32497(14) 0.0299 1.0000 Uani D . . . . .
C8 C -0.21663(16) 0.41484(13) 0.27811(14) 0.0249 1.0000 Uani D . . . . .
C9 C -0.21708(15) 0.52904(13) 0.20871(13) 0.0228 1.0000 Uani . . . . . .
C10 C -0.35557(15) 0.58285(13) 0.15526(14) 0.0242 1.0000 Uani . . . . . .
C11 C -0.49048(15) 0.52519(13) 0.17207(14) 0.0244 1.0000 Uani . . . . . .
O12 O -0.62928(11) 0.57366(10) 0.12596(10) 0.0290 1.0000 Uani . . . . . .
C13 C -0.62245(17) 0.70091(14) 0.07535(16) 0.0308 1.0000 Uani . . . . . .
C14 C -0.49175(16) 0.40899(14) 0.23759(14) 0.0272 1.0000 Uani . . . . . .
C15 C -0.35673(16) 0.35560(14) 0.29055(15) 0.0272 1.0000 Uani . . . . . .
C16 C 0.17854(16) 0.32719(13) 0.36350(15) 0.0275 1.0000 Uani . . . . . .
C17 C 0.13677(19) 0.21064(15) 0.27826(19) 0.0388 1.0000 Uani . . . . . .
C18 C 0.2413(2) 0.12385(16) 0.3064(2) 0.0495 1.0000 Uani . . . . . .
C19 C 0.3875(2) 0.15246(18) 0.4203(2) 0.0511 1.0000 Uani . . . . . .
C20 C 0.4294(2) 0.2676(2) 0.50613(19) 0.0471 1.0000 Uani . . . . . .
C21 C 0.32478(19) 0.35463(17) 0.47700(16) 0.0353 1.0000 Uani . . . . . .
C22 C -0.09840(15) 0.85439(13) 0.22413(14) 0.0247 1.0000 Uani . . . . . .
C23 C -0.14219(17) 0.89761(14) 0.32465(16) 0.0295 1.0000 Uani . . . . . .
C24 C -0.24386(18) 0.98776(15) 0.29230(18) 0.0364 1.0000 Uani . . . . . .
C25 C -0.30067(18) 1.03107(15) 0.16173(19) 0.0401 1.0000 Uani . . . . . .
C26 C -0.25824(19) 0.98600(16) 0.06134(18) 0.0397 1.0000 Uani . . . . . .
C27 C -0.15518(18) 0.89752(14) 0.09214(16) 0.0327 1.0000 Uani . . . . . .
H41 H -0.1173 0.6003 0.0785 0.0278 1.0000 Uiso R . . . . .
H52 H 0.1406 0.5333 0.2039 0.0319 1.0000 Uiso R . . . . .
H51 H -0.0103 0.4191 0.1238 0.0324 1.0000 Uiso R . . . . .
H61 H 0.1125 0.4936 0.4145 0.0321 1.0000 Uiso R . . . . .
H101 H -0.3548 0.6592 0.1059 0.0291 1.0000 Uiso R . . . . .
H133 H -0.7254 0.7229 0.0551 0.0453 1.0000 Uiso R . . . . .
H132 H -0.5381 0.7669 0.1459 0.0436 1.0000 Uiso R . . . . .
H131 H -0.6043 0.6971 -0.0087 0.0441 1.0000 Uiso R . . . . .
H141 H -0.5847 0.3680 0.2480 0.0327 1.0000 Uiso R . . . . .
H151 H -0.3572 0.2774 0.3368 0.0323 1.0000 Uiso R . . . . .
H171 H 0.0343 0.1877 0.2014 0.0470 1.0000 Uiso R . . . . .
H181 H 0.2125 0.0460 0.2489 0.0597 1.0000 Uiso R . . . . .
H191 H 0.4582 0.0941 0.4388 0.0615 1.0000 Uiso R . . . . .
H201 H 0.5282 0.2871 0.5838 0.0571 1.0000 Uiso R . . . . .
H211 H 0.3533 0.4342 0.5354 0.0428 1.0000 Uiso R . . . . .
H231 H -0.1054 0.8659 0.4125 0.0360 1.0000 Uiso R . . . . .
H241 H -0.2731 1.0175 0.3602 0.0457 1.0000 Uiso R . . . . .
H251 H -0.3680 1.0929 0.1387 0.0485 1.0000 Uiso R . . . . .
H261 H -0.2971 1.0153 -0.0277 0.0486 1.0000 Uiso R . . . . .
H271 H -0.1220 0.8678 0.0262 0.0382 1.0000 Uiso R . . . . .
H71 H -0.0798(17) 0.3073(16) 0.3955(15) 0.0369(18) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.282(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O2 . 1.4398(10) yes
S1 . O3 . 1.4436(10) yes
S1 . C4 . 1.8228(13) yes
S1 . C22 . 1.7659(13) yes
C4 . C5 . 1.5408(18) yes
C4 . C9 . 1.5110(17) yes
C4 . H41 . 0.969 no
C5 . C6 . 1.5267(19) yes
C5 . H52 . 0.974 no
C5 . H51 . 0.988 no
C6 . N7 . 1.4535(17) yes
C6 . C16 . 1.5182(18) yes
C6 . H61 . 0.993 no
N7 . C8 . 1.3927(17) yes
N7 . H71 . 0.868(14) no
C8 . C9 . 1.3973(18) yes
C8 . C15 . 1.4071(18) yes
C9 . C10 . 1.4054(18) yes
C10 . C11 . 1.3823(18) yes
C10 . H101 . 0.953 no
C11 . O12 . 1.3776(16) yes
C11 . C14 . 1.3943(19) yes
O12 . C13 . 1.4253(17) yes
C13 . H133 . 0.968 no
C13 . H132 . 0.981 no
C13 . H131 . 0.978 no
C14 . C15 . 1.3759(19) yes
C14 . H141 . 0.949 no
C15 . H151 . 0.950 no
C16 . C17 . 1.390(2) yes
C16 . C21 . 1.384(2) yes
C17 . C18 . 1.388(2) yes
C17 . H171 . 0.958 no
C18 . C19 . 1.386(3) yes
C18 . H181 . 0.930 no
C19 . C20 . 1.381(3) yes
C19 . H191 . 0.937 no
C20 . C21 . 1.390(2) yes
C20 . H201 . 0.940 no
C21 . H211 . 0.950 no
C22 . C23 . 1.386(2) yes
C22 . C27 . 1.392(2) yes
C23 . C24 . 1.394(2) yes
C23 . H231 . 0.940 no
C24 . C25 . 1.380(2) yes
C24 . H241 . 0.936 no
C25 . C26 . 1.383(2) yes
C25 . H251 . 0.941 no
C26 . C27 . 1.390(2) yes
C26 . H261 . 0.940 no
C27 . H271 . 0.943 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . S1 . O3 . 118.07(7) yes
O2 . S1 . C4 . 110.33(6) yes
O3 . S1 . C4 . 105.93(6) yes
O2 . S1 . C22 . 107.69(6) yes
O3 . S1 . C22 . 107.41(6) yes
C4 . S1 . C22 . 106.88(6) yes
S1 . C4 . C5 . 108.01(9) yes
S1 . C4 . C9 . 115.15(9) yes
C5 . C4 . C9 . 112.54(10) yes
S1 . C4 . H41 . 103.1 no
C5 . C4 . H41 . 108.4 no
C9 . C4 . H41 . 109.0 no
C4 . C5 . C6 . 111.74(11) yes
C4 . C5 . H52 . 111.6 no
C6 . C5 . H52 . 110.4 no
C4 . C5 . H51 . 106.7 no
C6 . C5 . H51 . 108.5 no
H52 . C5 . H51 . 107.8 no
C5 . C6 . N7 . 108.26(11) yes
C5 . C6 . C16 . 112.72(11) yes
N7 . C6 . C16 . 108.69(11) yes
C5 . C6 . H61 . 108.5 no
N7 . C6 . H61 . 110.2 no
C16 . C6 . H61 . 108.5 no
C6 . N7 . C8 . 118.71(11) yes
C6 . N7 . H71 . 113.2(9) no
C8 . N7 . H71 . 113.5(9) no
N7 . C8 . C9 . 122.25(12) yes
N7 . C8 . C15 . 118.82(12) yes
C9 . C8 . C15 . 118.71(12) yes
C4 . C9 . C8 . 120.09(11) yes
C4 . C9 . C10 . 119.94(11) yes
C8 . C9 . C10 . 119.52(12) yes
C9 . C10 . C11 . 120.82(12) yes
C9 . C10 . H101 . 118.4 no
C11 . C10 . H101 . 120.8 no
C10 . C11 . O12 . 124.36(12) yes
C10 . C11 . C14 . 119.67(12) yes
O12 . C11 . C14 . 115.96(11) yes
C11 . O12 . C13 . 116.25(10) yes
O12 . C13 . H133 . 105.5 no
O12 . C13 . H132 . 110.8 no
H133 . C13 . H132 . 109.8 no
O12 . C13 . H131 . 110.1 no
H133 . C13 . H131 . 110.4 no
H132 . C13 . H131 . 110.2 no
C11 . C14 . C15 . 119.93(12) yes
C11 . C14 . H141 . 120.1 no
C15 . C14 . H141 . 119.9 no
C8 . C15 . C14 . 121.28(12) yes
C8 . C15 . H151 . 118.9 no
C14 . C15 . H151 . 119.8 no
C6 . C16 . C17 . 121.39(13) yes
C6 . C16 . C21 . 119.53(13) yes
C17 . C16 . C21 . 119.08(14) yes
C16 . C17 . C18 . 120.24(16) yes
C16 . C17 . H171 . 120.6 no
C18 . C17 . H171 . 119.2 no
C17 . C18 . C19 . 120.14(17) yes
C17 . C18 . H181 . 119.7 no
C19 . C18 . H181 . 120.1 no
C18 . C19 . C20 . 119.97(15) yes
C18 . C19 . H191 . 120.0 no
C20 . C19 . H191 . 120.0 no
C19 . C20 . C21 . 119.68(17) yes
C19 . C20 . H201 . 120.2 no
C21 . C20 . H201 . 120.1 no
C20 . C21 . C16 . 120.89(16) yes
C20 . C21 . H211 . 120.0 no
C16 . C21 . H211 . 119.1 no
S1 . C22 . C23 . 119.66(11) yes
S1 . C22 . C27 . 118.75(11) yes
C23 . C22 . C27 . 121.56(13) yes
C22 . C23 . C24 . 118.75(14) yes
C22 . C23 . H231 . 120.7 no
C24 . C23 . H231 . 120.5 no
C23 . C24 . C25 . 120.07(15) yes
C23 . C24 . H241 . 118.9 no
C25 . C24 . H241 . 121.0 no
C24 . C25 . C26 . 120.83(14) yes
C24 . C25 . H251 . 121.1 no
C26 . C25 . H251 . 118.0 no
C25 . C26 . C27 . 119.97(15) yes
C25 . C26 . H261 . 120.9 no
C27 . C26 . H261 . 119.1 no
C22 . C27 . C26 . 118.81(14) yes
C22 . C27 . H271 . 119.9 no
C26 . C27 . H271 . 121.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H52 . O12 1_655 156 0.97 2.59 3.497(2) yes
C6 . H61 . O2 . 129 0.99 2.55 3.269(2) yes
C13 . H133 . O3 1_455 134 0.97 2.49 3.230(2) yes
C21 . H211 . C14 2_566 157 0.95 2.59 3.487(2) yes
N7 . H71 . O2 2_566 157.0(14) 0.868 2.193 3.011(2) yes


