# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_2g
_database_code_depnum_ccdc_archive 'CCDC 2000237'
loop_
_audit_author_name
_audit_author_address
'Yao Shi'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
#============================================================================== 
_cell_length_a                   9.7260(2)
_cell_length_b                   11.7737(3)
_cell_length_c                   13.0343(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1492.57(3)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2

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 0.0181 0.0091 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 0.0311 0.0180 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'
S 0.3331 0.5567 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'
O 0.0492 0.0322 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'


_cell_formula_units_Z            4

# Given Formula = C16 H19 N1 O3 S1 
# Dc =      1.36 Fooo =    648.00 Mu =     20.12 M =    305.40
# Found Formula = C16 H19 N1 O3 S1 
# Dc =      1.36 FOOO =    648.00 Mu =     20.12 M =    305.40

_chemical_formula_sum            'C16 H19 N1 O3 S1'
_chemical_formula_moiety         'C16 H19 N1 O3 S1'
_chemical_compound_source        .
_chemical_formula_weight         305.40


_cell_measurement_reflns_used    4550
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.100

_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    2.012

# Sheldrick geometric approximatio 0.82 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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            8527
_reflns_number_total             3088
_diffrn_reflns_av_R_equivalents  0.037
# Number of reflections without Friedels Law is 3088 
# Number of reflections with Friedels Law is 1786 
# Theoretical number of reflections is about 1559 


_diffrn_reflns_theta_min         5.062
_diffrn_reflns_theta_max         76.039
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.518
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.22
_refine_diff_density_max         0.17


# 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         3087
_refine_ls_number_restraints     0
_refine_ls_number_parameters     191
_oxford_refine_ls_R_factor_ref   0.0328
_refine_ls_wR_factor_ref         0.0755
_refine_ls_goodness_of_fit_ref   0.9981
_refine_ls_shift/su_max          0.0004699
_refine_ls_shift/su_mean         0.0000427


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3088
_refine_ls_R_factor_all          0.0328
_refine_ls_wR_factor_all         0.0759

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2919
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_gt          0.0728

_refine_ls_abs_structure_Flack   -0.034(16)
_refine_ls_abs_structure_details 'Flack (1983), 1302 Friedel-pairs'
# 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 ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #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 + 0.16P] 
 ,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 0.43513(4) 0.30953(3) 0.74419(3) 0.0272 1.0000 Uani . . . . . .
O2 O 0.57095(12) 0.26414(12) 0.75491(11) 0.0380 1.0000 Uani . . . . . .
O3 O 0.40257(15) 0.41680(11) 0.78964(11) 0.0372 1.0000 Uani . . . . . .
N4 N 0.32979(14) 0.21737(11) 0.79341(11) 0.0248 1.0000 Uani . . . . . .
C5 C 0.18360(16) 0.24921(13) 0.80149(13) 0.0257 1.0000 Uani . . . . . .
C6 C 0.11325(17) 0.18421(15) 0.88877(13) 0.0276 1.0000 Uani . . . . . .
C7 C 0.14566(18) 0.05485(14) 0.88067(14) 0.0295 1.0000 Uani . . . . . .
C8 C 0.0734(2) 0.00641(14) 0.78694(14) 0.0315 1.0000 Uani . . . . . .
O9 O -0.05085(15) 0.00093(12) 0.78259(12) 0.0423 1.0000 Uani . . . . . .
C10 C 0.1649(2) -0.03524(16) 0.70164(16) 0.0377 1.0000 Uani . . . . . .
C11 C 0.28678(19) 0.04497(16) 0.68044(14) 0.0322 1.0000 Uani . . . . . .
C12 C 0.35520(18) 0.09396(14) 0.77866(14) 0.0287 1.0000 Uani . . . . . .
C13 C 0.30058(19) 0.03573(15) 0.87526(14) 0.0308 1.0000 Uani . . . . . .
C14 C 0.1440(2) 0.22610(16) 0.99534(14) 0.0335 1.0000 Uani . . . . . .
C15 C 0.2380(2) 0.30002(19) 1.02382(15) 0.0399 1.0000 Uani . . . . . .
C16 C 0.40258(16) 0.32038(15) 0.61069(13) 0.0279 1.0000 Uani . . . . . .
C17 C 0.3112(2) 0.40021(17) 0.57383(16) 0.0369 1.0000 Uani . . . . . .
C18 C 0.2875(3) 0.4043(2) 0.46863(19) 0.0488 1.0000 Uani . . . . . .
C19 C 0.3525(3) 0.3293(2) 0.40339(16) 0.0514 1.0000 Uani . . . . . .
C20 C 0.4433(3) 0.25068(19) 0.44143(16) 0.0476 1.0000 Uani . . . . . .
C21 C 0.4701(2) 0.24557(17) 0.54561(15) 0.0370 1.0000 Uani . . . . . .
H51 H 0.1762 0.3314 0.8152 0.0303 1.0000 Uiso R . . . . .
H52 H 0.1369 0.2297 0.7387 0.0295 1.0000 Uiso R . . . . .
H61 H 0.0128 0.1923 0.8763 0.0311 1.0000 Uiso R . . . . .
H71 H 0.1065 0.0193 0.9422 0.0348 1.0000 Uiso R . . . . .
H101 H 0.1072 -0.0472 0.6397 0.0435 1.0000 Uiso R . . . . .
H102 H 0.2031 -0.1086 0.7234 0.0456 1.0000 Uiso R . . . . .
H111 H 0.2554 0.1068 0.6370 0.0371 1.0000 Uiso R . . . . .
H112 H 0.3538 0.0031 0.6429 0.0395 1.0000 Uiso R . . . . .
H121 H 0.4533 0.0843 0.7744 0.0327 1.0000 Uiso R . . . . .
H131 H 0.3435 0.0689 0.9356 0.0352 1.0000 Uiso R . . . . .
H132 H 0.3196 -0.0452 0.8713 0.0365 1.0000 Uiso R . . . . .
H141 H 0.0854 0.1979 1.0470 0.0409 1.0000 Uiso R . . . . .
H152 H 0.2480 0.3181 1.0936 0.0479 1.0000 Uiso R . . . . .
H151 H 0.2934 0.3364 0.9747 0.0482 1.0000 Uiso R . . . . .
H171 H 0.2662 0.4503 0.6172 0.0437 1.0000 Uiso R . . . . .
H181 H 0.2284 0.4576 0.4432 0.0596 1.0000 Uiso R . . . . .
H191 H 0.3368 0.3334 0.3337 0.0628 1.0000 Uiso R . . . . .
H201 H 0.4924 0.1994 0.3960 0.0581 1.0000 Uiso R . . . . .
H211 H 0.5354 0.1917 0.5723 0.0451 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.03(19)
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 . 1.4318(13) yes
S1 . O3 . 1.4304(14) yes
S1 . N4 . 1.6244(14) yes
S1 . C16 . 1.7733(18) yes
N4 . C5 . 1.474(2) yes
N4 . C12 . 1.486(2) yes
C5 . C6 . 1.532(2) yes
C5 . H51 . 0.987 no
C5 . H52 . 0.963 no
C6 . C7 . 1.559(2) yes
C6 . C14 . 1.504(2) yes
C6 . H61 . 0.995 no
C7 . C8 . 1.520(3) yes
C7 . C13 . 1.525(2) yes
C7 . H71 . 0.981 no
C8 . O9 . 1.212(2) yes
C8 . C10 . 1.506(3) yes
C10 . C11 . 1.540(3) yes
C10 . H101 . 0.993 no
C10 . H102 . 0.982 no
C11 . C12 . 1.554(3) yes
C11 . H111 . 0.972 no
C11 . H112 . 0.953 no
C12 . C13 . 1.529(2) yes
C12 . H121 . 0.962 no
C13 . H131 . 0.972 no
C13 . H132 . 0.972 no
C14 . C15 . 1.316(3) yes
C14 . H141 . 0.942 no
C15 . H152 . 0.939 no
C15 . H151 . 0.940 no
C16 . C17 . 1.380(3) yes
C16 . C21 . 1.388(3) yes
C17 . C18 . 1.391(3) yes
C17 . H171 . 0.927 no
C18 . C19 . 1.379(4) yes
C18 . H181 . 0.914 no
C19 . C20 . 1.372(4) yes
C19 . H191 . 0.922 no
C20 . C21 . 1.384(3) yes
C20 . H201 . 0.971 no
C21 . H211 . 0.963 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 . 119.56(9) yes
O2 . S1 . N4 . 107.10(8) yes
O3 . S1 . N4 . 106.65(8) yes
O2 . S1 . C16 . 106.70(8) yes
O3 . S1 . C16 . 107.66(9) yes
N4 . S1 . C16 . 108.85(8) yes
S1 . N4 . C5 . 117.82(11) yes
S1 . N4 . C12 . 119.81(11) yes
C5 . N4 . C12 . 114.72(13) yes
N4 . C5 . C6 . 110.90(13) yes
N4 . C5 . H51 . 109.5 no
C6 . C5 . H51 . 108.8 no
N4 . C5 . H52 . 109.5 no
C6 . C5 . H52 . 107.5 no
H51 . C5 . H52 . 110.6 no
C5 . C6 . C7 . 110.33(13) yes
C5 . C6 . C14 . 115.67(15) yes
C7 . C6 . C14 . 110.05(15) yes
C5 . C6 . H61 . 105.6 no
C7 . C6 . H61 . 106.4 no
C14 . C6 . H61 . 108.3 no
C6 . C7 . C8 . 109.12(14) yes
C6 . C7 . C13 . 110.31(14) yes
C8 . C7 . C13 . 111.35(15) yes
C6 . C7 . H71 . 106.5 no
C8 . C7 . H71 . 108.5 no
C13 . C7 . H71 . 111.0 no
C7 . C8 . O9 . 121.24(17) yes
C7 . C8 . C10 . 116.24(16) yes
O9 . C8 . C10 . 122.52(18) yes
C8 . C10 . C11 . 112.80(15) yes
C8 . C10 . H101 . 108.2 no
C11 . C10 . H101 . 112.1 no
C8 . C10 . H102 . 107.3 no
C11 . C10 . H102 . 107.5 no
H101 . C10 . H102 . 108.8 no
C10 . C11 . C12 . 114.16(15) yes
C10 . C11 . H111 . 108.8 no
C12 . C11 . H111 . 109.7 no
C10 . C11 . H112 . 107.5 no
C12 . C11 . H112 . 108.8 no
H111 . C11 . H112 . 107.7 no
C11 . C12 . N4 . 113.47(14) yes
C11 . C12 . C13 . 111.30(15) yes
N4 . C12 . C13 . 105.90(14) yes
C11 . C12 . H121 . 109.4 no
N4 . C12 . H121 . 106.8 no
C13 . C12 . H121 . 109.8 no
C12 . C13 . C7 . 108.37(14) yes
C12 . C13 . H131 . 109.7 no
C7 . C13 . H131 . 109.1 no
C12 . C13 . H132 . 109.3 no
C7 . C13 . H132 . 109.6 no
H131 . C13 . H132 . 110.7 no
C6 . C14 . C15 . 127.98(17) yes
C6 . C14 . H141 . 115.1 no
C15 . C14 . H141 . 116.8 no
C14 . C15 . H152 . 119.7 no
C14 . C15 . H151 . 120.5 no
H152 . C15 . H151 . 119.8 no
S1 . C16 . C17 . 120.37(14) yes
S1 . C16 . C21 . 118.00(15) yes
C17 . C16 . C21 . 121.62(18) yes
C16 . C17 . C18 . 118.3(2) yes
C16 . C17 . H171 . 121.7 no
C18 . C17 . H171 . 120.0 no
C17 . C18 . C19 . 120.6(2) yes
C17 . C18 . H181 . 119.1 no
C19 . C18 . H181 . 120.3 no
C18 . C19 . C20 . 120.3(2) yes
C18 . C19 . H191 . 119.8 no
C20 . C19 . H191 . 119.9 no
C19 . C20 . C21 . 120.3(2) yes
C19 . C20 . H201 . 121.1 no
C21 . C20 . H201 . 118.6 no
C16 . C21 . C20 . 118.9(2) yes
C16 . C21 . H211 . 120.6 no
C20 . C21 . H211 . 120.5 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
C12 . H121 . O3 4_646 130.80(5) 0.962 2.559 3.270(3) yes
C17 . H171 . O9 4_556 148.53(6) 0.927 2.539 3.365(3) yes


