# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_yjc_h1_161025_2
_database_code_depnum_ccdc_archive 'CCDC 1817567'
_audit_update_record             
;
2018-01-17 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O3 S'
_chemical_formula_sum            'C15 H19 N O3 S'
_chemical_formula_weight         293.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0093(2)
_cell_length_b                   14.3918(3)
_cell_length_c                   10.7208(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.176(2)
_cell_angle_gamma                90
_cell_volume                     1497.33(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4075
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.8690
_cell_measurement_theta_min      3.0530
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.505
_exptl_absorpt_coefficient_mu    1.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6258
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.556
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  53.00   1.00    3.00    --   44.40 -57.00  60.00   52
  2  ω     89.00 114.00   1.00    3.00    --   44.40  57.00  30.00   25
  3  ω     74.00 111.00   1.00    3.00    --   44.40 125.00  30.00   37
  4  ω    107.00 170.00   1.00    8.00    --  100.00  61.00   0.00   63
  5  ω     36.00 117.00   1.00    8.00    --  100.00-125.00-120.00   81
  6  ω     94.00 120.00   1.00    8.00    --  100.00-125.00-180.00   26
  7  ω     28.00 129.00   1.00    8.00    --  100.00 -77.00-120.00  101
  8  ω     27.00  90.00   1.00    8.00    --  100.00-125.00-180.00   63
  9  ω     19.00  46.00   1.00    3.00    --   44.40  57.00  30.00   27
 10  ω    -55.00 -18.00   1.00    8.00    --  -90.00 125.00 -60.00   37
 11  ω   -115.00 -90.00   1.00    8.00    --  -90.00 125.00 -60.00   25
 12  ω   -160.00-107.00   1.00    8.00    --  -90.00 -61.00  30.00   53
 13  ω   -117.00 -77.00   1.00    3.00    --  -44.40-125.00 -90.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0230452000
_diffrn_orient_matrix_UB_12      0.0459827000
_diffrn_orient_matrix_UB_13      -0.1228276000
_diffrn_orient_matrix_UB_21      0.0394183000
_diffrn_orient_matrix_UB_22      0.0915593000
_diffrn_orient_matrix_UB_23      0.0742349000
_diffrn_orient_matrix_UB_31      0.1520452000
_diffrn_orient_matrix_UB_32      -0.0308070000
_diffrn_orient_matrix_UB_33      0.0372873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2520
_reflns_number_total             2663
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.5750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0756
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C12(H12), C16(H16), C17(H17), C19(H19)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.89393(3) -0.21655(2) -0.14661(3) 0.02293(11) Uani 1 1 d . . . . .
O1 O -0.84113(9) -0.11514(6) -0.33301(8) 0.0206(2) Uani 1 1 d . . . . .
O2 O -0.55016(9) -0.13228(6) 0.09432(8) 0.0211(2) Uani 1 1 d . . . . .
H2 H -0.529874 -0.174472 0.149891 0.032 Uiso 1 1 calc GR . . . .
O3 O -0.54512(9) -0.20464(6) -0.26313(9) 0.0209(2) Uani 1 1 d . . . . .
N4 N -0.57515(10) -0.06373(7) -0.18003(10) 0.0165(2) Uani 1 1 d . . . . .
H4 H -0.546628 -0.005720 -0.170891 0.020 Uiso 1 1 calc R . . . .
C5 C -0.51429(13) -0.12141(9) -0.24869(12) 0.0171(3) Uani 1 1 d . . . . .
C6 C -0.64079(13) -0.16828(9) -0.01847(12) 0.0177(3) Uani 1 1 d . . . . .
H6 H -0.592617 -0.218546 -0.054842 0.021 Uiso 1 1 calc R . . . .
C7 C -0.68493(12) -0.09114(9) -0.12005(11) 0.0163(3) Uani 1 1 d . . . . .
C8 C -0.41098(16) 0.01461(10) -0.34116(14) 0.0278(3) Uani 1 1 d . . . . .
H8 H -0.485581 0.052588 -0.331893 0.033 Uiso 1 1 calc R . . . .
C9 C -0.84359(13) 0.05872(10) -0.14788(13) 0.0216(3) Uani 1 1 d . . . . .
H9 H -0.928170 0.020992 -0.183752 0.026 Uiso 1 1 calc R . . . .
C10 C -0.80648(13) -0.13461(9) -0.22047(12) 0.0178(3) Uani 1 1 d . . . . .
C11 C -0.73628(13) -0.00420(9) -0.06035(12) 0.0181(3) Uani 1 1 d . . . . .
H11A H -0.775504 -0.025463 0.011004 0.022 Uiso 1 1 calc R . . . .
H11B H -0.654849 0.034509 -0.021878 0.022 Uiso 1 1 calc R . . . .
C12 C -0.29729(15) -0.13327(10) -0.32094(14) 0.0276(3) Uani 1 1 d . . . . .
H12 H -0.294079 -0.197150 -0.298077 0.033 Uiso 1 1 calc R . . . .
C13 C -0.40549(13) -0.07845(9) -0.30439(12) 0.0185(3) Uani 1 1 d . . . . .
C14 C -0.77227(14) -0.20772(9) 0.00919(12) 0.0213(3) Uani 1 1 d . . . . .
H14A H -0.807906 -0.165766 0.066730 0.026 Uiso 1 1 calc R . . . .
H14B H -0.754710 -0.269569 0.050366 0.026 Uiso 1 1 calc R . . . .
C15 C -0.79512(14) 0.10079(10) -0.26016(13) 0.0236(3) Uani 1 1 d . . . . .
H15A H -0.777420 0.050930 -0.316278 0.035 Uiso 1 1 calc GR . . . .
H15B H -0.710235 0.136201 -0.226885 0.035 Uiso 1 1 calc GR . . . .
H15C H -0.866625 0.142204 -0.309302 0.035 Uiso 1 1 calc GR . . . .
C16 C -0.19830(15) -0.00310(12) -0.40499(13) 0.0310(3) Uani 1 1 d . . . . .
H16 H -0.126779 0.022965 -0.437998 0.037 Uiso 1 1 calc R . . . .
C17 C -0.19375(15) -0.09564(12) -0.37058(15) 0.0323(3) Uani 1 1 d . . . . .
H17 H -0.119565 -0.133603 -0.380917 0.039 Uiso 1 1 calc R . . . .
C18 C -0.88071(17) 0.13555(11) -0.06353(15) 0.0327(3) Uani 1 1 d . . . . .
H18A H -0.798692 0.172950 -0.026819 0.049 Uiso 1 1 calc GR . . . .
H18B H -0.914788 0.107570 0.006097 0.049 Uiso 1 1 calc GR . . . .
H18C H -0.952432 0.175314 -0.115873 0.049 Uiso 1 1 calc GR . . . .
C19 C -0.30755(17) 0.05160(11) -0.39122(15) 0.0347(4) Uani 1 1 d . . . . .
H19 H -0.311555 0.115042 -0.416337 0.042 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 C10 1.7673(13) . ?
S1 C14 1.8146(13) . ?
O1 C10 1.2040(16) . ?
O2 H2 0.8400 . ?
O2 C6 1.4199(15) . ?
O3 C5 1.2373(16) . ?
N4 H4 0.8800 . ?
N4 C5 1.3496(16) . ?
N4 C7 1.4570(16) . ?
C5 C13 1.4978(18) . ?
C6 H6 1.0000 . ?
C6 C7 1.5421(17) . ?
C6 C14 1.5275(18) . ?
C7 C10 1.5457(17) . ?
C7 C11 1.5494(17) . ?
C8 H8 0.9500 . ?
C8 C13 1.393(2) . ?
C8 C19 1.384(2) . ?
C9 H9 1.0000 . ?
C9 C11 1.5364(18) . ?
C9 C15 1.5287(19) . ?
C9 C18 1.5307(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C12 C17 1.386(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.380(2) . ?
C16 C19 1.384(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 0.9500 . ?

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
C10 S1 C14 94.09(6) . . ?
C6 O2 H2 109.5 . . ?
C5 N4 H4 117.8 . . ?
C5 N4 C7 124.34(11) . . ?
C7 N4 H4 117.8 . . ?
O3 C5 N4 122.12(12) . . ?
O3 C5 C13 122.22(11) . . ?
N4 C5 C13 115.65(11) . . ?
O2 C6 H6 109.1 . . ?
O2 C6 C7 110.58(10) . . ?
O2 C6 C14 111.81(10) . . ?
C7 C6 H6 109.1 . . ?
C14 C6 H6 109.1 . . ?
C14 C6 C7 107.05(10) . . ?
N4 C7 C6 112.96(10) . . ?
N4 C7 C10 110.62(10) . . ?
N4 C7 C11 109.03(10) . . ?
C6 C7 C10 103.95(10) . . ?
C6 C7 C11 110.88(10) . . ?
C10 C7 C11 109.30(10) . . ?
C13 C8 H8 120.1 . . ?
C19 C8 H8 120.1 . . ?
C19 C8 C13 119.87(14) . . ?
C11 C9 H9 108.3 . . ?
C15 C9 H9 108.3 . . ?
C15 C9 C11 113.90(11) . . ?
C15 C9 C18 110.42(12) . . ?
C18 C9 H9 108.3 . . ?
C18 C9 C11 107.42(11) . . ?
O1 C10 S1 123.47(10) . . ?
O1 C10 C7 126.04(11) . . ?
C7 C10 S1 110.47(9) . . ?
C7 C11 H11A 107.7 . . ?
C7 C11 H11B 107.7 . . ?
C9 C11 C7 118.47(10) . . ?
C9 C11 H11A 107.7 . . ?
C9 C11 H11B 107.7 . . ?
H11A C11 H11B 107.1 . . ?
C13 C12 H12 119.7 . . ?
C17 C12 H12 119.7 . . ?
C17 C12 C13 120.53(14) . . ?
C8 C13 C5 121.83(12) . . ?
C12 C13 C5 118.90(12) . . ?
C12 C13 C8 119.27(12) . . ?
S1 C14 H14A 110.7 . . ?
S1 C14 H14B 110.7 . . ?
C6 C14 S1 105.26(9) . . ?
C6 C14 H14A 110.7 . . ?
C6 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C19 119.71(14) . . ?
C19 C16 H16 120.1 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.07(14) . . ?
C16 C17 H17 120.0 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 C16 120.54(14) . . ?
C8 C19 H19 119.7 . . ?
C16 C19 H19 119.7 . . ?

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 C6 C7 N4 72.89(13) . . . . ?
O2 C6 C7 C10 -167.16(10) . . . . ?
O2 C6 C7 C11 -49.83(13) . . . . ?
O2 C6 C14 S1 162.97(8) . . . . ?
O3 C5 C13 C8 150.03(13) . . . . ?
O3 C5 C13 C12 -29.26(18) . . . . ?
N4 C5 C13 C8 -30.93(17) . . . . ?
N4 C5 C13 C12 149.78(12) . . . . ?
N4 C7 C10 S1 150.76(8) . . . . ?
N4 C7 C10 O1 -30.94(17) . . . . ?
N4 C7 C11 C9 83.47(13) . . . . ?
C5 N4 C7 C6 61.12(15) . . . . ?
C5 N4 C7 C10 -54.92(15) . . . . ?
C5 N4 C7 C11 -175.14(11) . . . . ?
C6 C7 C10 S1 29.24(11) . . . . ?
C6 C7 C10 O1 -152.46(12) . . . . ?
C6 C7 C11 C9 -151.57(11) . . . . ?
C7 N4 C5 O3 -2.18(19) . . . . ?
C7 N4 C5 C13 178.77(10) . . . . ?
C7 C6 C14 S1 41.72(11) . . . . ?
C10 S1 C14 C6 -20.97(10) . . . . ?
C10 C7 C11 C9 -37.56(15) . . . . ?
C11 C7 C10 S1 -89.19(10) . . . . ?
C11 C7 C10 O1 89.12(15) . . . . ?
C13 C8 C19 C16 -0.1(2) . . . . ?
C13 C12 C17 C16 -0.5(2) . . . . ?
C14 S1 C10 O1 176.54(11) . . . . ?
C14 S1 C10 C7 -5.11(9) . . . . ?
C14 C6 C7 N4 -165.10(10) . . . . ?
C14 C6 C7 C10 -45.14(12) . . . . ?
C14 C6 C7 C11 72.19(12) . . . . ?
C15 C9 C11 C7 -60.16(15) . . . . ?
C17 C12 C13 C5 -179.13(13) . . . . ?
C17 C12 C13 C8 1.6(2) . . . . ?
C17 C16 C19 C8 1.1(2) . . . . ?
C18 C9 C11 C7 177.22(11) . . . . ?
C19 C8 C13 C5 179.46(13) . . . . ?
C19 C8 C13 C12 -1.3(2) . . . . ?
C19 C16 C17 C12 -0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.951
_oxdiff_exptl_absorpt_empirical_full_min 0.593
####################################################################### 
# 
# 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_yjc_h2_161018
_database_code_depnum_ccdc_archive 'CCDC 1817568'
_audit_update_record             
;
2018-01-17 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O3 S'
_chemical_formula_sum            'C15 H19 N O3 S'
_chemical_formula_weight         293.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.54242(11)
_cell_length_b                   22.4359(3)
_cell_length_c                   10.03319(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.1649(17)
_cell_angle_gamma                90
_cell_volume                     1439.65(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4455
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.0450
_cell_measurement_theta_min      6.0210
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.577
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6007
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         5.993
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  45.00   1.00    3.00    --   44.52  57.00 -30.00   25
  2  ω     83.00 109.00   1.00    3.00    --   44.52  57.00 -30.00   26
  3  ω    122.00 171.00   1.00    8.00    --  100.00  30.00-150.00   49
  4  ω     68.00 126.00   1.00    8.00    --  100.00  77.00 150.00   58
  5  ω     19.00 107.00   1.00    8.00    --  100.00 -94.00 120.00   88
  6  ω     26.00 119.00   1.00    8.00    --  100.00-125.00  60.00   93
  7  ω    -70.00  23.00   1.00    3.00    --  -44.52  57.00 -90.00   93
  8  ω   -126.00 -85.00   1.00    3.00    --  -44.52 -99.00-180.00   41
  9  ω   -149.00 -74.00   1.00    8.00    --  -90.00-125.00-180.00   75
 10  ω   -163.00 -89.00   1.00    8.00    --  -90.00-125.00 -60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0649995000
_diffrn_orient_matrix_UB_12      0.0087418000
_diffrn_orient_matrix_UB_13      -0.1555063000
_diffrn_orient_matrix_UB_21      0.0028521000
_diffrn_orient_matrix_UB_22      0.0681419000
_diffrn_orient_matrix_UB_23      0.0201246000
_diffrn_orient_matrix_UB_31      0.2317183000
_diffrn_orient_matrix_UB_32      0.0015617000
_diffrn_orient_matrix_UB_33      -0.0094666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2441
_reflns_number_total             2540
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.4649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0940
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C8(H8), C12(H12), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25185(5) 0.44151(2) 0.64076(3) 0.02232(14) Uani 1 1 d . . . . .
O1 O 0.17806(15) 0.46309(5) 0.94254(10) 0.0224(2) Uani 1 1 d . . . . .
H1 H 0.089349 0.439324 0.961786 0.034 Uiso 1 1 calc GR . . . .
O2 O 0.10196(15) 0.61651(4) 0.98019(10) 0.0232(2) Uani 1 1 d . . . . .
N3 N 0.37567(18) 0.57048(5) 0.91640(12) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.510109 0.562486 0.940321 0.023 Uiso 1 1 calc R . . . .
O4 O 0.58597(15) 0.50221(5) 0.75914(10) 0.0267(3) Uani 1 1 d . . . . .
C5 C 0.2523(2) 0.54043(6) 0.79748(14) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.3823(2) 0.67237(6) 1.20072(15) 0.0230(3) Uani 1 1 d . . . . .
H6 H 0.248984 0.662612 1.218017 0.028 Uiso 1 1 calc R . . . .
C7 C 0.1471(2) 0.58557(6) 0.68612(14) 0.0213(3) Uani 1 1 d . . . . .
H7A H 0.113607 0.564054 0.598057 0.026 Uiso 1 1 calc R . . . .
H7B H 0.012561 0.597992 0.707829 0.026 Uiso 1 1 calc R . . . .
C8 C 0.6381(2) 0.66407(6) 1.06101(15) 0.0225(3) Uani 1 1 d . . . . .
H8 H 0.680174 0.648804 0.982666 0.027 Uiso 1 1 calc R . . . .
C9 C 0.2676(2) 0.64211(7) 0.66510(15) 0.0252(3) Uani 1 1 d . . . . .
H9 H 0.294884 0.665276 0.752201 0.030 Uiso 1 1 calc R . . . .
C10 C 0.2930(2) 0.60993(6) 0.99124(14) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.4440(2) 0.64876(6) 1.08666(14) 0.0201(3) Uani 1 1 d . . . . .
C12 C 0.7704(2) 0.70167(7) 1.14979(16) 0.0278(3) Uani 1 1 d . . . . .
H12 H 0.903495 0.711723 1.132519 0.033 Uiso 1 1 calc R . . . .
C13 C 0.0155(2) 0.45953(6) 0.70036(15) 0.0224(3) Uani 1 1 d . . . . .
H13A H -0.083674 0.481669 0.629376 0.027 Uiso 1 1 calc R . . . .
H13B H -0.053639 0.422690 0.722577 0.027 Uiso 1 1 calc R . . . .
C14 C 0.3986(2) 0.49822(6) 0.73979(13) 0.0203(3) Uani 1 1 d . . . . .
C15 C 0.1278(3) 0.67974(7) 0.55523(17) 0.0321(4) Uani 1 1 d . . . . .
H15A H 0.112015 0.659768 0.466779 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.191794 0.718984 0.550688 0.048 Uiso 1 1 calc GR . . . .
H15C H -0.009817 0.684584 0.577831 0.048 Uiso 1 1 calc GR . . . .
C16 C 0.0837(2) 0.49816(6) 0.82828(14) 0.0195(3) Uani 1 1 d . . . . .
H16 H -0.037465 0.521172 0.848018 0.023 Uiso 1 1 calc R . . . .
C17 C 0.5148(3) 0.71007(7) 1.28908(15) 0.0274(3) Uani 1 1 d . . . . .
H17 H 0.472598 0.725895 1.366871 0.033 Uiso 1 1 calc R . . . .
C18 C 0.7089(3) 0.72453(7) 1.26343(16) 0.0293(4) Uani 1 1 d . . . . .
H18 H 0.799944 0.750192 1.323949 0.035 Uiso 1 1 calc R . . . .
C19 C 0.4760(3) 0.63022(8) 0.62586(18) 0.0349(4) Uani 1 1 d . . . . .
H19A H 0.570965 0.610636 0.701829 0.052 Uiso 1 1 calc GR . . . .
H19B H 0.537356 0.668044 0.605001 0.052 Uiso 1 1 calc GR . . . .
H19C H 0.454064 0.604316 0.545448 0.052 Uiso 1 1 calc GR . . . .


_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 C13 1.8171(15) . ?
S1 C14 1.7680(14) . ?
O1 H1 0.8400 . ?
O1 C16 1.4200(16) . ?
O2 C10 1.2398(17) . ?
N3 H3 0.8800 . ?
N3 C5 1.4573(17) . ?
N3 C10 1.3458(18) . ?
O4 C14 1.2035(17) . ?
C5 C7 1.5569(19) . ?
C5 C14 1.5431(19) . ?
C5 C16 1.5349(19) . ?
C6 H6 0.9500 . ?
C6 C11 1.396(2) . ?
C6 C17 1.389(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C9 1.531(2) . ?
C8 H8 0.9500 . ?
C8 C11 1.391(2) . ?
C8 C12 1.389(2) . ?
C9 H9 1.0000 . ?
C9 C15 1.529(2) . ?
C9 C19 1.521(2) . ?
C10 C11 1.5009(19) . ?
C12 H12 0.9500 . ?
C12 C18 1.385(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C16 1.5350(19) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C14 S1 C13 93.09(6) . . ?
C16 O1 H1 109.5 . . ?
C5 N3 H3 118.6 . . ?
C10 N3 H3 118.6 . . ?
C10 N3 C5 122.86(12) . . ?
N3 C5 C7 111.81(11) . . ?
N3 C5 C14 108.11(11) . . ?
N3 C5 C16 114.74(11) . . ?
C14 C5 C7 110.21(11) . . ?
C16 C5 C7 108.56(11) . . ?
C16 C5 C14 103.01(11) . . ?
C11 C6 H6 119.8 . . ?
C17 C6 H6 119.8 . . ?
C17 C6 C11 120.34(14) . . ?
C5 C7 H7A 107.7 . . ?
C5 C7 H7B 107.7 . . ?
H7A C7 H7B 107.1 . . ?
C9 C7 C5 118.35(12) . . ?
C9 C7 H7A 107.7 . . ?
C9 C7 H7B 107.7 . . ?
C11 C8 H8 119.9 . . ?
C12 C8 H8 119.9 . . ?
C12 C8 C11 120.10(14) . . ?
C7 C9 H9 108.2 . . ?
C15 C9 C7 108.04(12) . . ?
C15 C9 H9 108.2 . . ?
C19 C9 C7 113.97(13) . . ?
C19 C9 H9 108.2 . . ?
C19 C9 C15 110.04(13) . . ?
O2 C10 N3 123.00(13) . . ?
O2 C10 C11 120.23(12) . . ?
N3 C10 C11 116.72(12) . . ?
C6 C11 C10 118.57(12) . . ?
C8 C11 C6 119.40(13) . . ?
C8 C11 C10 121.96(12) . . ?
C8 C12 H12 119.9 . . ?
C18 C12 C8 120.18(14) . . ?
C18 C12 H12 119.9 . . ?
S1 C13 H13A 110.4 . . ?
S1 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C16 C13 S1 106.46(10) . . ?
C16 C13 H13A 110.4 . . ?
C16 C13 H13B 110.4 . . ?
O4 C14 S1 123.93(11) . . ?
O4 C14 C5 125.80(13) . . ?
C5 C14 S1 110.26(9) . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 C5 107.23(11) . . ?
O1 C16 C13 111.25(11) . . ?
O1 C16 H16 110.7 . . ?
C5 C16 C13 105.96(11) . . ?
C5 C16 H16 110.7 . . ?
C13 C16 H16 110.7 . . ?
C6 C17 H17 120.1 . . ?
C18 C17 C6 119.81(14) . . ?
C18 C17 H17 120.1 . . ?
C12 C18 C17 120.17(14) . . ?
C12 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
S1 C13 C16 O1 -76.03(12) . . . . ?
S1 C13 C16 C5 40.20(13) . . . . ?
O2 C10 C11 C6 27.57(19) . . . . ?
O2 C10 C11 C8 -149.22(14) . . . . ?
N3 C5 C7 C9 36.21(16) . . . . ?
N3 C5 C14 S1 158.02(9) . . . . ?
N3 C5 C14 O4 -21.36(19) . . . . ?
N3 C5 C16 O1 -46.22(15) . . . . ?
N3 C5 C16 C13 -165.13(11) . . . . ?
N3 C10 C11 C6 -155.16(13) . . . . ?
N3 C10 C11 C8 28.06(19) . . . . ?
C5 N3 C10 O2 12.6(2) . . . . ?
C5 N3 C10 C11 -164.59(12) . . . . ?
C5 C7 C9 C15 -177.73(12) . . . . ?
C5 C7 C9 C19 59.64(17) . . . . ?
C6 C17 C18 C12 0.2(2) . . . . ?
C7 C5 C14 S1 -79.50(12) . . . . ?
C7 C5 C14 O4 101.12(16) . . . . ?
C7 C5 C16 O1 -172.12(10) . . . . ?
C7 C5 C16 C13 68.97(13) . . . . ?
C8 C12 C18 C17 -0.1(2) . . . . ?
C10 N3 C5 C7 59.31(17) . . . . ?
C10 N3 C5 C14 -179.19(12) . . . . ?
C10 N3 C5 C16 -64.89(17) . . . . ?
C11 C6 C17 C18 0.3(2) . . . . ?
C11 C8 C12 C18 -0.6(2) . . . . ?
C12 C8 C11 C6 1.2(2) . . . . ?
C12 C8 C11 C10 177.95(13) . . . . ?
C13 S1 C14 O4 167.52(13) . . . . ?
C13 S1 C14 C5 -11.89(10) . . . . ?
C14 S1 C13 C16 -16.29(10) . . . . ?
C14 C5 C7 C9 -84.07(15) . . . . ?
C14 C5 C16 O1 71.03(12) . . . . ?
C14 C5 C16 C13 -47.88(13) . . . . ?
C16 C5 C7 C9 163.80(12) . . . . ?
C16 C5 C14 S1 36.18(12) . . . . ?
C16 C5 C14 O4 -143.20(14) . . . . ?
C17 C6 C11 C8 -1.0(2) . . . . ?
C17 C6 C11 C10 -177.90(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.558
_oxdiff_exptl_absorpt_empirical_full_min 0.580
