# Electronic Supplementary Material (ESI) for ChemComm.
# 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 
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data_4a
_database_code_depnum_ccdc_archive 'CCDC 1815452'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-06-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H22 N2 O3 S'
_chemical_formula_sum            'C19 H22 N2 O3 S'
_chemical_formula_weight         358.44
_chemical_absolute_configuration syn
_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 0.0033 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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   9.389(3)
_cell_length_b                   12.021(4)
_cell_length_c                   17.402(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1964.1(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1693
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.285
_cell_measurement_theta_min      2.341
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0613 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.9305.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.144
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12293
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.920
_diffrn_reflns_theta_min         2.341
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2549
_reflns_number_total             4633
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      0.968
_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)+(0.0531P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1234
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C17(H17), C19(H19), C18(H18), C9(H9), C13(H13), C11(H11),
 C12(H12), C10(H10)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C3(H3A,H3B,H3C)
;
_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 1.12101(10) 0.51823(8) 0.54349(6) 0.0660(3) Uani 1 1 d . . . . .
N2 N 0.9791(3) 0.4096(2) 0.69396(18) 0.0585(8) Uani 1 1 d . . . . .
O1 O 0.8526(3) 0.2788(2) 0.54026(16) 0.0725(7) Uani 1 1 d . . . . .
N1 N 1.0230(3) 0.4081(2) 0.51933(17) 0.0609(8) Uani 1 1 d . . . . .
O2 O 1.1111(3) 0.3835(2) 0.68458(15) 0.0766(8) Uani 1 1 d . . . . .
C2 C 0.8832(4) 0.4020(3) 0.6402(2) 0.0573(9) Uani 1 1 d . . . . .
C8 C 0.7299(4) 0.4259(4) 0.6546(2) 0.0654(10) Uani 1 1 d . . . . .
C14 C 0.9437(3) 0.4534(3) 0.7699(2) 0.0546(9) Uani 1 1 d . . . . .
C16 C 0.8962(4) 0.6087(4) 0.8487(3) 0.0790(12) Uani 1 1 d . . . . .
H16 H 0.8836 0.6850 0.8548 0.095 Uiso 1 1 calc R . . . .
C15 C 0.9259(4) 0.5656(3) 0.7774(2) 0.0682(11) Uani 1 1 d . . . . .
H15 H 0.9337 0.6121 0.7349 0.082 Uiso 1 1 calc R . . . .
C17 C 0.8853(4) 0.5399(4) 0.9104(2) 0.0789(12) Uani 1 1 d . . . . .
H17 H 0.8649 0.5695 0.9585 0.095 Uiso 1 1 calc R . . . .
C1 C 0.9292(4) 0.3663(3) 0.5631(2) 0.0583(9) Uani 1 1 d . . . . .
C6 C 1.1983(5) 0.4897(4) 0.3930(2) 0.0866(13) Uani 1 1 d . . . . .
H6A H 1.2858 0.4644 0.4155 0.130 Uiso 1 1 calc GR . . . .
H6B H 1.2175 0.5228 0.3439 0.130 Uiso 1 1 calc GR . . . .
H6C H 1.1349 0.4278 0.3865 0.130 Uiso 1 1 calc GR . . . .
C19 C 0.9344(4) 0.3833(3) 0.8315(2) 0.0700(11) Uani 1 1 d . . . . .
H19 H 0.9483 0.3071 0.8260 0.084 Uiso 1 1 calc R . . . .
C18 C 0.9034(4) 0.4300(4) 0.9028(3) 0.0810(12) Uani 1 1 d . . . . .
H18 H 0.8951 0.3843 0.9457 0.097 Uiso 1 1 calc R . . . .
C4 C 1.1296(4) 0.5755(3) 0.4455(2) 0.0716(10) Uani 1 1 d . . . . .
C9 C 0.6462(5) 0.3503(5) 0.6918(2) 0.0965(15) Uani 1 1 d . . . . .
H9 H 0.6841 0.2834 0.7090 0.116 Uiso 1 1 calc R . . . .
C13 C 0.6714(5) 0.5217(5) 0.6271(3) 0.0924(15) Uani 1 1 d . . . . .
H13 H 0.7276 0.5723 0.6004 0.111 Uiso 1 1 calc R . . . .
C11 C 0.4461(6) 0.4705(8) 0.6761(3) 0.136(3) Uani 1 1 d . . . . .
H11 H 0.3498 0.4857 0.6831 0.164 Uiso 1 1 calc R . . . .
C12 C 0.5274(6) 0.5438(6) 0.6389(4) 0.125(2) Uani 1 1 d . . . . .
H12 H 0.4880 0.6097 0.6208 0.150 Uiso 1 1 calc R . . . .
C10 C 0.5004(6) 0.3757(7) 0.7036(3) 0.120(2) Uani 1 1 d . . . . .
H10 H 0.4425 0.3264 0.7305 0.143 Uiso 1 1 calc R . . . .
C5 C 0.9810(5) 0.6056(4) 0.4187(3) 0.1086(18) Uani 1 1 d . . . . .
H5A H 0.9269 0.5389 0.4106 0.163 Uiso 1 1 calc GR . . . .
H5B H 0.9868 0.6466 0.3715 0.163 Uiso 1 1 calc GR . . . .
H5C H 0.9352 0.6504 0.4571 0.163 Uiso 1 1 calc GR . . . .
C7 C 1.2258(6) 0.6762(4) 0.4533(3) 0.1094(17) Uani 1 1 d . . . . .
H7A H 1.1805 0.7308 0.4852 0.164 Uiso 1 1 calc GR . . . .
H7B H 1.2435 0.7073 0.4034 0.164 Uiso 1 1 calc GR . . . .
H7C H 1.3144 0.6541 0.4762 0.164 Uiso 1 1 calc GR . . . .
O3 O 1.0390(3) 0.5996(2) 0.58921(16) 0.0812(8) Uani 1 1 d . . . . .
C3 C 0.8851(5) 0.2360(3) 0.4649(2) 0.0813(12) Uani 1 1 d . . . . .
H3A H 0.8773 0.2947 0.4278 0.122 Uiso 1 1 calc GR . . . .
H3B H 0.8193 0.1777 0.4523 0.122 Uiso 1 1 calc GR . . . .
H3C H 0.9804 0.2070 0.4645 0.122 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 N1 1.666(3) . ?
S1 C4 1.842(4) . ?
S1 O3 1.477(3) . ?
N2 O2 1.289(3) . ?
N2 C2 1.302(4) . ?
N2 C14 1.460(4) . ?
O1 C1 1.335(4) . ?
O1 C3 1.441(4) . ?
N1 C1 1.267(4) . ?
C2 C8 1.488(5) . ?
C2 C1 1.474(5) . ?
C8 C9 1.365(6) . ?
C8 C13 1.362(6) . ?
C14 C15 1.365(5) . ?
C14 C19 1.367(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.373(5) . ?
C16 C17 1.359(6) . ?
C15 H15 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.338(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C6 C4 1.522(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.393(6) . ?
C18 H18 0.9300 . ?
C4 C5 1.514(5) . ?
C4 C7 1.516(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.417(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.393(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.333(9) . ?
C11 C10 1.338(8) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
N1 S1 C4 95.02(17) . . ?
O3 S1 N1 111.94(15) . . ?
O3 S1 C4 105.90(17) . . ?
O2 N2 C2 123.9(3) . . ?
O2 N2 C14 114.9(3) . . ?
C2 N2 C14 121.2(3) . . ?
C1 O1 C3 116.0(3) . . ?
C1 N1 S1 123.2(3) . . ?
N2 C2 C8 122.3(3) . . ?
N2 C2 C1 118.1(3) . . ?
C1 C2 C8 119.5(3) . . ?
C9 C8 C2 120.5(4) . . ?
C13 C8 C2 119.6(4) . . ?
C13 C8 C9 119.8(4) . . ?
C15 C14 N2 118.1(3) . . ?
C15 C14 C19 121.7(4) . . ?
C19 C14 N2 120.1(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.9(4) . . ?
C14 C15 C16 119.0(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.5 . . ?
O1 C1 C2 110.0(3) . . ?
N1 C1 O1 120.5(3) . . ?
N1 C1 C2 129.4(3) . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
C14 C19 H19 121.2 . . ?
C14 C19 C18 117.6(4) . . ?
C18 C19 H19 121.2 . . ?
C17 C18 C19 120.8(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C6 C4 S1 108.7(3) . . ?
C5 C4 S1 109.5(3) . . ?
C5 C4 C6 111.6(4) . . ?
C5 C4 C7 112.7(4) . . ?
C7 C4 S1 104.0(3) . . ?
C7 C4 C6 110.0(3) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.9(6) . . ?
C10 C9 H9 120.6 . . ?
C8 C13 H13 120.0 . . ?
C8 C13 C12 120.1(6) . . ?
C12 C13 H13 120.0 . . ?
C12 C11 H11 119.4 . . ?
C12 C11 C10 121.3(6) . . ?
C10 C11 H11 119.4 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.1(7) . . ?
C11 C12 H12 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10 120.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 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 N1 C1 O1 179.2(2) . . . . ?
S1 N1 C1 C2 1.2(5) . . . . ?
N2 C2 C8 C9 -76.7(5) . . . . ?
N2 C2 C8 C13 106.5(5) . . . . ?
N2 C2 C1 O1 125.4(3) . . . . ?
N2 C2 C1 N1 -56.5(5) . . . . ?
N2 C14 C15 C16 -178.3(3) . . . . ?
N2 C14 C19 C18 178.6(3) . . . . ?
N1 S1 C4 C6 -59.2(3) . . . . ?
N1 S1 C4 C5 63.0(3) . . . . ?
N1 S1 C4 C7 -176.3(3) . . . . ?
O2 N2 C2 C8 175.9(4) . . . . ?
O2 N2 C2 C1 -2.8(5) . . . . ?
O2 N2 C14 C15 102.4(4) . . . . ?
O2 N2 C14 C19 -75.2(4) . . . . ?
C2 N2 C14 C15 -75.4(4) . . . . ?
C2 N2 C14 C19 107.0(4) . . . . ?
C2 C8 C9 C10 -179.3(4) . . . . ?
C2 C8 C13 C12 178.7(4) . . . . ?
C8 C2 C1 O1 -53.4(4) . . . . ?
C8 C2 C1 N1 124.7(4) . . . . ?
C8 C9 C10 C11 2.4(8) . . . . ?
C8 C13 C12 C11 -1.0(8) . . . . ?
C14 N2 C2 C8 -6.5(5) . . . . ?
C14 N2 C2 C1 174.7(3) . . . . ?
C14 C19 C18 C17 -0.8(6) . . . . ?
C16 C17 C18 C19 0.2(7) . . . . ?
C15 C14 C19 C18 1.1(6) . . . . ?
C15 C16 C17 C18 0.2(7) . . . . ?
C17 C16 C15 C14 0.1(6) . . . . ?
C1 C2 C8 C9 102.1(5) . . . . ?
C1 C2 C8 C13 -74.8(5) . . . . ?
C19 C14 C15 C16 -0.7(6) . . . . ?
C4 S1 N1 C1 -145.5(3) . . . . ?
C9 C8 C13 C12 1.9(7) . . . . ?
C13 C8 C9 C10 -2.5(6) . . . . ?
C12 C11 C10 C9 -1.6(9) . . . . ?
C10 C11 C12 C13 0.9(10) . . . . ?
O3 S1 N1 C1 -36.1(3) . . . . ?
O3 S1 C4 C6 -173.7(3) . . . . ?
O3 S1 C4 C5 -51.5(4) . . . . ?
O3 S1 C4 C7 69.2(3) . . . . ?
C3 O1 C1 N1 0.8(5) . . . . ?
C3 O1 C1 C2 179.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4k'
_database_code_depnum_ccdc_archive 'CCDC 1815453'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H21 F N2 O3 S'
_chemical_formula_sum            'C19 H21 F N2 O3 S'
_chemical_formula_weight         376.44
_chemical_absolute_configuration syn
_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 0.0033 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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   11.4001(18)
_cell_length_b                   12.5665(19)
_cell_length_c                   14.190(2)
_cell_angle_alpha                76.975(2)
_cell_angle_beta                 89.282(2)
_cell_angle_gamma                79.014(2)
_cell_volume                     1943.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2060
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.116
_cell_measurement_theta_min      2.306
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0540 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9174.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.183
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11861
_diffrn_reflns_point_group_measured_fraction_full 0.604
_diffrn_reflns_point_group_measured_fraction_max 0.575
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.423
_diffrn_reflns_theta_min         2.306
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.199
_reflns_Friedel_fraction_full    0.225
_reflns_Friedel_fraction_max     0.191
_reflns_number_gt                5911
_reflns_number_total             10200
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.15(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     953
_refine_ls_number_reflns         10200
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      0.998
_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)+(0.0545P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1366
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C38(H38), C64(H64), C61(H61), C62(H62), C76(H76), C72(H72), C27(H27),
 C34(H34), C24(H24), C36(H36), C26(H26), C74(H74), C65(H65), C23(H23), C73(H73),
  C35(H35), C75(H75), C37(H37), C4(H4), C8(H8), C7(H7), C17(H17), C19(H19),
 C5(H5), C15(H15), C18(H18), C16(H16), C53(H53), C46(H46), C55(H55), C45(H45),
 C42(H42), C54(H54), C57(H57), C56(H56), C43(H43)
2.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C66(H66A,H66B,H66C), C32(H32A,H32B,H32C), C69(H69A,H69B,
 H69C), C68(H68A,H68B,H68C), C28(H28A,H28B,H28C), C70(H70A,H70B,H70C), C31(H31A,
 H31B,H31C), C12(H12A,H12B,H12C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C11(H11A,H11B,H11C), C50(H50A,H50B,H50C), C47(H47A,H47B,H47C), C49(H49A,H49B,
 H49C), C51(H51A,H51B,H51C)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S -0.34424(14) -0.05251(12) -0.93441(10) 0.0614(4) Uani 1 1 d . . .
S4 S -0.81585(14) -0.17240(12) -0.78231(10) 0.0630(4) Uani 1 1 d . . .
O4 O -0.3575(4) 0.2577(3) -0.9442(3) 0.0665(11) Uani 1 1 d . . .
O12 O -0.8689(3) -0.4266(3) -0.5110(3) 0.0695(11) Uani 1 1 d . . .
N4 N -0.4219(4) 0.1807(4) -1.1291(3) 0.0565(12) Uani 1 1 d . . .
O6 O -0.4824(4) 0.1949(4) -1.2090(3) 0.0851(14) Uani 1 1 d . . .
N8 N -0.8090(4) -0.4112(4) -0.5890(3) 0.0496(11) Uani 1 1 d . . .
O5 O -0.4477(4) -0.0426(3) -0.9993(3) 0.0741(12) Uani 1 1 d . . .
C20 C -0.3787(5) 0.1618(5) -0.9627(4) 0.0508(13) Uani 1 1 d . . .
N3 N -0.3304(4) 0.0687(4) -0.9107(3) 0.0559(12) Uani 1 1 d . . .
O10 O -0.7071(3) -0.4836(3) -0.7743(3) 0.0648(11) Uani 1 1 d . . .
C71 C -0.6898(5) -0.3914(5) -0.5744(4) 0.0509(13) Uani 1 1 d . . .
C33 C -0.2919(5) 0.1551(5) -1.1415(3) 0.0549(14) Uani 1 1 d . . .
C63 C -1.1792(5) -0.4819(5) -0.7452(5) 0.0652(16) Uani 1 1 d . . .
C59 C -0.8495(5) -0.4106(4) -0.6756(4) 0.0467(12) Uani 1 1 d . . .
C22 C -0.5918(5) 0.2162(4) -1.0288(4) 0.0540(14) Uani 1 1 d . . .
C38 C -0.2431(7) 0.0557(5) -1.1630(4) 0.0701(17) Uani 1 1 d . . .
H38 H -0.2902 0.0037 -1.1664 0.084 Uiso 1 1 calc R . .
C60 C -0.9652(5) -0.4348(4) -0.6965(4) 0.0484(13) Uani 1 1 d . . .
C58 C -0.7654(5) -0.3872(5) -0.7564(4) 0.0485(13) Uani 1 1 d . . .
N7 N -0.7530(4) -0.2945(4) -0.8069(3) 0.0557(12) Uani 1 1 d . . .
F4 F -1.2854(3) -0.5074(3) -0.7676(3) 0.0950(12) Uani 1 1 d . . .
C64 C -1.1603(6) -0.4731(5) -0.6544(5) 0.0722(18) Uani 1 1 d . . .
H64 H -1.2188 -0.4830 -0.6087 0.087 Uiso 1 1 calc R . .
C21 C -0.4668(5) 0.1880(4) -1.0462(3) 0.0476(13) Uani 1 1 d . . .
C61 C -0.9892(5) -0.4461(5) -0.7884(4) 0.0646(16) Uani 1 1 d . . .
H61 H -0.9314 -0.4385 -0.8350 0.078 Uiso 1 1 calc R . .
F2 F -0.9477(3) 0.2929(4) -0.9672(3) 0.1086(14) Uani 1 1 d . . .
C25 C -0.8302(5) 0.2685(5) -0.9889(6) 0.078(2) Uani 1 1 d . . .
C62 C -1.0968(6) -0.4684(5) -0.8123(5) 0.0725(18) Uani 1 1 d . . .
H62 H -1.1123 -0.4741 -0.8750 0.087 Uiso 1 1 calc R . .
C76 C -0.5935(5) -0.4724(5) -0.5775(4) 0.0643(16) Uani 1 1 d . . .
H76 H -0.6032 -0.5390 -0.5916 0.077 Uiso 1 1 calc R . .
C72 C -0.6792(6) -0.2919(5) -0.5528(4) 0.0628(16) Uani 1 1 d . . .
H72 H -0.7462 -0.2378 -0.5492 0.075 Uiso 1 1 calc R . .
C27 C -0.6283(5) 0.2292(5) -0.9372(4) 0.0664(16) Uani 1 1 d . . .
H27 H -0.5702 0.2201 -0.8892 0.080 Uiso 1 1 calc R . .
C34 C -0.2268(6) 0.2335(5) -1.1385(4) 0.0632(16) Uani 1 1 d . . .
H34 H -0.2623 0.3011 -1.1246 0.076 Uiso 1 1 calc R . .
C24 C -0.8010(6) 0.2561(6) -1.0788(6) 0.0792(19) Uani 1 1 d . . .
H24 H -0.8601 0.2633 -1.1257 0.095 Uiso 1 1 calc R . .
C36 C -0.0556(6) 0.1113(7) -1.1754(5) 0.082(2) Uani 1 1 d . . .
H36 H 0.0260 0.0959 -1.1856 0.098 Uiso 1 1 calc R . .
C26 C -0.7452(6) 0.2543(6) -0.9151(5) 0.083(2) Uani 1 1 d . . .
H26 H -0.7676 0.2618 -0.8534 0.099 Uiso 1 1 calc R . .
C74 C -0.4671(6) -0.3570(6) -0.5389(4) 0.0707(18) Uani 1 1 d . . .
H74 H -0.3912 -0.3456 -0.5263 0.085 Uiso 1 1 calc R . .
C65 C -1.0530(5) -0.4492(5) -0.6296(4) 0.0636(16) Uani 1 1 d . . .
H65 H -1.0397 -0.4428 -0.5668 0.076 Uiso 1 1 calc R . .
C23 C -0.6819(6) 0.2324(5) -1.0997(5) 0.0677(17) Uani 1 1 d . . .
H23 H -0.6608 0.2271 -1.1622 0.081 Uiso 1 1 calc R . .
C73 C -0.5652(7) -0.2755(6) -0.5367(4) 0.0737(18) Uani 1 1 d . . .
H73 H -0.5550 -0.2083 -0.5242 0.088 Uiso 1 1 calc R . .
C35 C -0.1057(6) 0.2111(6) -1.1566(5) 0.0762(18) Uani 1 1 d . . .
H35 H -0.0591 0.2641 -1.1557 0.091 Uiso 1 1 calc R . .
C30 C -0.4125(8) -0.2291(6) -0.8236(5) 0.105(3) Uani 1 1 d . . .
H30A H -0.4784 -0.2159 -0.8689 0.158 Uiso 1 1 calc R . .
H30B H -0.4326 -0.2702 -0.7620 0.158 Uiso 1 1 calc R . .
H30C H -0.3433 -0.2711 -0.8468 0.158 Uiso 1 1 calc R . .
C67 C -0.8809(6) -0.1049(6) -0.9046(4) 0.0744(18) Uani 1 1 d . . .
C75 C -0.4811(6) -0.4551(6) -0.5596(5) 0.0763(19) Uani 1 1 d . . .
H75 H -0.4145 -0.5102 -0.5615 0.092 Uiso 1 1 calc R . .
C29 C -0.3854(6) -0.1172(5) -0.8127(4) 0.0692(17) Uani 1 1 d . . .
C66 C -0.6221(7) -0.4772(7) -0.8486(5) 0.110(3) Uani 1 1 d . . .
H66A H -0.6576 -0.4247 -0.9057 0.165 Uiso 1 1 calc R . .
H66B H -0.5977 -0.5492 -0.8630 0.165 Uiso 1 1 calc R . .
H66C H -0.5538 -0.4536 -0.8273 0.165 Uiso 1 1 calc R . .
C32 C -0.2756(8) -0.1349(7) -0.7465(5) 0.121(3) Uani 1 1 d . . .
H32A H -0.2090 -0.1791 -0.7708 0.182 Uiso 1 1 calc R . .
H32B H -0.2918 -0.1727 -0.6824 0.182 Uiso 1 1 calc R . .
H32C H -0.2568 -0.0641 -0.7446 0.182 Uiso 1 1 calc R . .
C69 C -0.7776(8) -0.0879(9) -0.9700(6) 0.137(4) Uani 1 1 d . . .
H69A H -0.7225 -0.0555 -0.9400 0.206 Uiso 1 1 calc R . .
H69B H -0.8069 -0.0390 -1.0307 0.206 Uiso 1 1 calc R . .
H69C H -0.7375 -0.1583 -0.9809 0.206 Uiso 1 1 calc R . .
C37 C -0.1218(7) 0.0341(6) -1.1798(4) 0.0735(18) Uani 1 1 d . . .
H37 H -0.0862 -0.0333 -1.1940 0.088 Uiso 1 1 calc R . .
C68 C -0.9514(8) 0.0057(6) -0.8935(5) 0.105(3) Uani 1 1 d . . .
H68A H -1.0078 -0.0062 -0.8432 0.158 Uiso 1 1 calc R . .
H68B H -0.9935 0.0442 -0.9534 0.158 Uiso 1 1 calc R . .
H68C H -0.8980 0.0496 -0.8770 0.158 Uiso 1 1 calc R . .
C28 C -0.2740(8) 0.2447(6) -0.8641(5) 0.106(3) Uani 1 1 d . . .
H28A H -0.1989 0.2010 -0.8758 0.159 Uiso 1 1 calc R . .
H28B H -0.3056 0.2078 -0.8053 0.159 Uiso 1 1 calc R . .
H28C H -0.2625 0.3166 -0.8581 0.159 Uiso 1 1 calc R . .
C70 C -0.9624(7) -0.1718(6) -0.9342(5) 0.101(2) Uani 1 1 d . . .
H70A H -0.9160 -0.2352 -0.9533 0.151 Uiso 1 1 calc R . .
H70B H -1.0131 -0.1268 -0.9877 0.151 Uiso 1 1 calc R . .
H70C H -1.0107 -0.1964 -0.8808 0.151 Uiso 1 1 calc R . .
C31 C -0.4931(7) -0.0474(6) -0.7819(5) 0.099(2) Uani 1 1 d . . .
H31A H -0.4719 0.0181 -0.7682 0.148 Uiso 1 1 calc R . .
H31B H -0.5234 -0.0891 -0.7248 0.148 Uiso 1 1 calc R . .
H31C H -0.5534 -0.0260 -0.8329 0.148 Uiso 1 1 calc R . .
S1 S -0.53087(13) 0.00219(12) -0.37416(10) 0.0593(4) Uani 1 1 d . . .
N2 N -0.6003(4) 0.2080(4) -0.6258(3) 0.0598(12) Uani 1 1 d . . .
C3 C -0.4397(5) 0.2292(4) -0.5226(4) 0.0465(12) Uani 1 1 d . . .
C2 C -0.5577(5) 0.2110(4) -0.5406(4) 0.0474(13) Uani 1 1 d . . .
F1 F -0.1077(3) 0.2802(4) -0.4583(3) 0.0957(12) Uani 1 1 d . . .
O3 O -0.5432(4) 0.2221(4) -0.7042(3) 0.0867(14) Uani 1 1 d . . .
C14 C -0.7199(5) 0.1841(5) -0.6362(4) 0.0526(13) Uani 1 1 d . . .
C1 C -0.6419(5) 0.1969(5) -0.4578(4) 0.0505(13) Uani 1 1 d . . .
N1 N -0.6391(4) 0.1159(4) -0.3867(3) 0.0543(11) Uani 1 1 d . . .
O1 O -0.7214(4) 0.2928(3) -0.4656(3) 0.0683(11) Uani 1 1 d . . .
O2 O -0.5128(4) -0.0341(3) -0.4654(3) 0.0721(12) Uani 1 1 d . . .
C4 C -0.4090(6) 0.2383(5) -0.4299(4) 0.0652(16) Uani 1 1 d . . .
H4 H -0.4646 0.2322 -0.3814 0.078 Uiso 1 1 calc R . .
C6 C -0.2186(5) 0.2638(5) -0.4804(5) 0.0610(15) Uani 1 1 d . . .
C8 C -0.3516(5) 0.2389(5) -0.5911(4) 0.0615(15) Uani 1 1 d . . .
H8 H -0.3685 0.2331 -0.6535 0.074 Uiso 1 1 calc R . .
C7 C -0.2416(6) 0.2566(5) -0.5702(5) 0.0669(17) Uani 1 1 d . . .
H7 H -0.1843 0.2634 -0.6173 0.080 Uiso 1 1 calc R . .
C17 C -0.9385(6) 0.1403(6) -0.6703(5) 0.0731(17) Uani 1 1 d . . .
H17 H -1.0135 0.1255 -0.6807 0.088 Uiso 1 1 calc R . .
C19 C -0.7301(5) 0.0751(5) -0.6270(4) 0.0643(16) Uani 1 1 d . . .
H19 H -0.6644 0.0174 -0.6096 0.077 Uiso 1 1 calc R . .
C5 C -0.2975(6) 0.2562(5) -0.4099(4) 0.0691(17) Uani 1 1 d . . .
H5 H -0.2775 0.2629 -0.3485 0.083 Uiso 1 1 calc R . .
C15 C -0.8154(6) 0.2692(5) -0.6631(5) 0.0728(18) Uani 1 1 d . . .
H15 H -0.8063 0.3424 -0.6696 0.087 Uiso 1 1 calc R . .
C18 C -0.8412(6) 0.0544(5) -0.6445(5) 0.0775(19) Uani 1 1 d . . .
H18 H -0.8508 -0.0186 -0.6389 0.093 Uiso 1 1 calc R . .
C10 C -0.6142(7) -0.0910(5) -0.2964(4) 0.0775(19) Uani 1 1 d . . .
C12 C -0.5330(8) -0.2051(6) -0.2790(5) 0.114(3) Uani 1 1 d . . .
H12A H -0.5291 -0.2318 -0.3375 0.171 Uiso 1 1 calc R . .
H12B H -0.5643 -0.2559 -0.2287 0.171 Uiso 1 1 calc R . .
H12C H -0.4542 -0.1995 -0.2600 0.171 Uiso 1 1 calc R . .
C16 C -0.9230(6) 0.2469(6) -0.6804(5) 0.085(2) Uani 1 1 d . . .
H16 H -0.9877 0.3053 -0.6994 0.102 Uiso 1 1 calc R . .
C9 C -0.8125(7) 0.2928(6) -0.3945(5) 0.102(3) Uani 1 1 d . . .
H9A H -0.8622 0.3655 -0.4050 0.154 Uiso 1 1 calc R . .
H9B H -0.7756 0.2736 -0.3309 0.154 Uiso 1 1 calc R . .
H9C H -0.8604 0.2394 -0.4002 0.154 Uiso 1 1 calc R . .
C13 C -0.6344(10) -0.0510(7) -0.2025(5) 0.136(4) Uani 1 1 d . . .
H13A H -0.5612 -0.0355 -0.1811 0.204 Uiso 1 1 calc R . .
H13B H -0.6598 -0.1078 -0.1538 0.204 Uiso 1 1 calc R . .
H13C H -0.6949 0.0155 -0.2136 0.204 Uiso 1 1 calc R . .
C11 C -0.7279(7) -0.0931(7) -0.3473(6) 0.115(3) Uani 1 1 d . . .
H11A H -0.7873 -0.0297 -0.3416 0.172 Uiso 1 1 calc R . .
H11B H -0.7558 -0.1601 -0.3184 0.172 Uiso 1 1 calc R . .
H11C H -0.7133 -0.0909 -0.4144 0.172 Uiso 1 1 calc R . .
S3 S -0.97953(12) -0.23013(12) -0.34661(10) 0.0569(4) Uani 1 1 d . . .
C40 C -0.9215(5) -0.4376(4) -0.1793(4) 0.0477(13) Uani 1 1 d . . .
O8 O -0.9796(3) -0.1941(3) -0.2549(3) 0.0623(10) Uani 1 1 d . . .
N5 N -1.0357(4) -0.3465(4) -0.3333(3) 0.0521(11) Uani 1 1 d . . .
N6 N -0.9697(4) -0.4288(4) -0.0973(3) 0.0590(12) Uani 1 1 d . . .
O7 O -1.0415(4) -0.5245(3) -0.2570(3) 0.0753(13) Uani 1 1 d . . .
C41 C -0.7945(5) -0.4607(4) -0.1957(4) 0.0504(13) Uani 1 1 d . . .
O9 O -0.9107(4) -0.4338(4) -0.0187(3) 0.0910(15) Uani 1 1 d . . .
F3 F -0.4342(3) -0.5357(4) -0.2476(3) 0.1085(14) Uani 1 1 d . . .
C52 C -1.0991(5) -0.4063(5) -0.0862(4) 0.0545(14) Uani 1 1 d . . .
C39 C -1.0045(5) -0.4287(4) -0.2622(4) 0.0486(13) Uani 1 1 d . . .
C53 C -1.1556(6) -0.2996(5) -0.0904(4) 0.0672(16) Uani 1 1 d . . .
H53 H -1.1137 -0.2416 -0.1056 0.081 Uiso 1 1 calc R . .
C46 C -0.7526(5) -0.4691(5) -0.2871(4) 0.0634(16) Uani 1 1 d . . .
H46 H -0.8077 -0.4565 -0.3380 0.076 Uiso 1 1 calc R . .
C55 C -1.3375(6) -0.3647(6) -0.0525(5) 0.0735(18) Uani 1 1 d . . .
H55 H -1.4193 -0.3494 -0.0429 0.088 Uiso 1 1 calc R . .
C45 C -0.6349(6) -0.4949(5) -0.3042(5) 0.0772(19) Uani 1 1 d . . .
H45 H -0.6104 -0.5005 -0.3660 0.093 Uiso 1 1 calc R . .
C44 C -0.5532(6) -0.5124(5) -0.2319(5) 0.0714(17) Uani 1 1 d . . .
C42 C -0.7058(5) -0.4783(5) -0.1226(5) 0.0663(16) Uani 1 1 d . . .
H42 H -0.7283 -0.4724 -0.0604 0.080 Uiso 1 1 calc R . .
C54 C -1.2741(6) -0.2789(5) -0.0720(5) 0.0735(18) Uani 1 1 d . . .
H54 H -1.3128 -0.2066 -0.0727 0.088 Uiso 1 1 calc R . .
C57 C -1.1565(6) -0.4918(5) -0.0672(5) 0.0696(17) Uani 1 1 d . . .
H57 H -1.1160 -0.5634 -0.0671 0.084 Uiso 1 1 calc R . .
C56 C -1.2795(6) -0.4722(6) -0.0471(5) 0.0779(19) Uani 1 1 d . . .
H56 H -1.3202 -0.5309 -0.0307 0.093 Uiso 1 1 calc R . .
C43 C -0.5870(6) -0.5041(6) -0.1416(5) 0.079(2) Uani 1 1 d . . .
H43 H -0.5295 -0.5159 -0.0925 0.095 Uiso 1 1 calc R . .
C50 C -1.1046(9) -0.1789(7) -0.5159(5) 0.136(4) Uani 1 1 d . . .
H50A H -1.0244 -0.1951 -0.5376 0.204 Uiso 1 1 calc R . .
H50B H -1.1521 -0.1218 -0.5645 0.204 Uiso 1 1 calc R . .
H50C H -1.1383 -0.2449 -0.5047 0.204 Uiso 1 1 calc R . .
C48 C -1.1029(6) -0.1387(5) -0.4218(4) 0.078(2) Uani 1 1 d . . .
C47 C -1.1246(8) -0.5254(7) -0.3330(5) 0.117(3) Uani 1 1 d . . .
H47A H -1.0868 -0.5121 -0.3943 0.176 Uiso 1 1 calc R . .
H47B H -1.1939 -0.4681 -0.3340 0.176 Uiso 1 1 calc R . .
H47C H -1.1481 -0.5965 -0.3212 0.176 Uiso 1 1 calc R . .
C49 C -1.0652(10) -0.0250(6) -0.4405(6) 0.134(4) Uani 1 1 d . . .
H49A H -1.0735 0.0028 -0.3825 0.201 Uiso 1 1 calc R . .
H49B H -1.1151 0.0263 -0.4914 0.201 Uiso 1 1 calc R . .
H49C H -0.9833 -0.0329 -0.4592 0.201 Uiso 1 1 calc R . .
C51 C -1.2187(6) -0.1420(8) -0.3696(7) 0.131(4) Uani 1 1 d . . .
H51A H -1.2345 -0.2162 -0.3571 0.197 Uiso 1 1 calc R . .
H51B H -1.2827 -0.0916 -0.4090 0.197 Uiso 1 1 calc R . .
H51C H -1.2125 -0.1204 -0.3094 0.197 Uiso 1 1 calc R . .
O11 O -0.9171(4) -0.1818(3) -0.7178(3) 0.0720(11) 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
S2 O5 1.474(4) . ?
S2 N3 1.668(5) . ?
S2 C29 1.833(6) . ?
S4 O11 1.469(4) . ?
S4 N7 1.675(5) . ?
S4 C67 1.846(6) . ?
O4 C20 1.354(6) . ?
O4 C28 1.453(7) . ?
O12 N8 1.290(5) . ?
N4 C21 1.292(6) . ?
N4 O6 1.294(5) . ?
N4 C33 1.472(7) . ?
N8 C59 1.315(6) . ?
N8 C71 1.453(7) . ?
C20 N3 1.262(7) . ?
C20 C21 1.500(7) . ?
O10 C58 1.342(6) . ?
O10 C66 1.422(7) . ?
C71 C76 1.355(7) . ?
C71 C72 1.380(8) . ?
C33 C34 1.350(8) . ?
C33 C38 1.366(8) . ?
C63 C62 1.336(9) . ?
C63 C64 1.341(9) . ?
C63 F4 1.369(7) . ?
C59 C60 1.458(7) . ?
C59 C58 1.500(7) . ?
C22 C27 1.394(8) . ?
C22 C23 1.401(8) . ?
C22 C21 1.433(7) . ?
C38 C37 1.386(9) . ?
C60 C65 1.379(7) . ?
C60 C61 1.380(7) . ?
C58 N7 1.254(6) . ?
C64 C65 1.382(9) . ?
C61 C62 1.371(8) . ?
F2 C25 1.364(7) . ?
C25 C24 1.350(9) . ?
C25 C26 1.394(9) . ?
C76 C75 1.376(8) . ?
C72 C73 1.384(8) . ?
C27 C26 1.360(8) . ?
C34 C35 1.389(8) . ?
C24 C23 1.377(9) . ?
C36 C37 1.350(9) . ?
C36 C35 1.358(9) . ?
C74 C75 1.368(8) . ?
C74 C73 1.370(9) . ?
C30 C29 1.536(9) . ?
C67 C70 1.487(9) . ?
C67 C68 1.507(9) . ?
C67 C69 1.508(10) . ?
C29 C31 1.489(9) . ?
C29 C32 1.526(9) . ?
S1 O2 1.466(4) . ?
S1 N1 1.677(5) . ?
S1 C10 1.819(6) . ?
N2 O3 1.276(6) . ?
N2 C2 1.319(6) . ?
N2 C14 1.467(7) . ?
C3 C8 1.392(7) . ?
C3 C4 1.400(7) . ?
C3 C2 1.442(7) . ?
C2 C1 1.509(7) . ?
F1 C6 1.370(6) . ?
C14 C15 1.363(8) . ?
C14 C19 1.373(8) . ?
C1 N1 1.258(6) . ?
C1 O1 1.346(6) . ?
O1 C9 1.438(7) . ?
C4 C5 1.376(8) . ?
C6 C7 1.330(8) . ?
C6 C5 1.336(8) . ?
C8 C7 1.362(8) . ?
C17 C16 1.359(9) . ?
C17 C18 1.380(9) . ?
C19 C18 1.376(8) . ?
C15 C16 1.346(9) . ?
C10 C11 1.499(10) . ?
C10 C12 1.521(10) . ?
C10 C13 1.527(9) . ?
S3 O8 1.471(4) . ?
S3 N5 1.677(5) . ?
S3 C48 1.818(6) . ?
C40 N6 1.299(6) . ?
C40 C41 1.448(7) . ?
C40 C39 1.489(7) . ?
N5 C39 1.270(6) . ?
N6 O9 1.293(5) . ?
N6 C52 1.461(7) . ?
O7 C39 1.337(6) . ?
O7 C47 1.447(7) . ?
C41 C46 1.396(7) . ?
C41 C42 1.409(7) . ?
F3 C44 1.359(7) . ?
C52 C57 1.337(8) . ?
C52 C53 1.361(7) . ?
C53 C54 1.359(8) . ?
C46 C45 1.351(8) . ?
C55 C56 1.372(9) . ?
C55 C54 1.385(9) . ?
C45 C44 1.347(8) . ?
C44 C43 1.354(9) . ?
C42 C43 1.370(9) . ?
C57 C56 1.413(9) . ?
C50 C48 1.532(9) . ?
C48 C51 1.508(10) . ?
C48 C49 1.536(11) . ?

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
O5 S2 N3 112.9(2) . . ?
O5 S2 C29 106.5(3) . . ?
N3 S2 C29 96.8(3) . . ?
O11 S4 N7 112.4(2) . . ?
O11 S4 C67 106.3(3) . . ?
N7 S4 C67 96.9(3) . . ?
C20 O4 C28 115.5(5) . . ?
C21 N4 O6 125.6(5) . . ?
C21 N4 C33 121.8(4) . . ?
O6 N4 C33 112.6(4) . . ?
O12 N8 C59 124.9(4) . . ?
O12 N8 C71 113.9(4) . . ?
C59 N8 C71 121.2(4) . . ?
N3 C20 O4 120.8(5) . . ?
N3 C20 C21 129.5(5) . . ?
O4 C20 C21 109.6(5) . . ?
C20 N3 S2 123.2(4) . . ?
C58 O10 C66 117.2(5) . . ?
C76 C71 C72 122.1(6) . . ?
C76 C71 N8 119.6(5) . . ?
C72 C71 N8 118.2(5) . . ?
C34 C33 C38 122.3(6) . . ?
C34 C33 N4 119.0(5) . . ?
C38 C33 N4 118.5(6) . . ?
C62 C63 C64 121.7(6) . . ?
C62 C63 F4 120.2(7) . . ?
C64 C63 F4 118.1(6) . . ?
N8 C59 C60 125.1(5) . . ?
N8 C59 C58 115.6(5) . . ?
C60 C59 C58 119.3(4) . . ?
C27 C22 C23 116.9(6) . . ?
C27 C22 C21 119.6(5) . . ?
C23 C22 C21 123.5(5) . . ?
C33 C38 C37 118.4(6) . . ?
C65 C60 C61 117.0(5) . . ?
C65 C60 C59 124.3(5) . . ?
C61 C60 C59 118.7(5) . . ?
N7 C58 O10 122.3(5) . . ?
N7 C58 C59 128.1(5) . . ?
O10 C58 C59 109.4(5) . . ?
C58 N7 S4 123.8(4) . . ?
C63 C64 C65 119.2(6) . . ?
N4 C21 C22 125.3(5) . . ?
N4 C21 C20 115.8(5) . . ?
C22 C21 C20 118.9(4) . . ?
C62 C61 C60 121.2(6) . . ?
C24 C25 F2 119.4(7) . . ?
C24 C25 C26 122.9(6) . . ?
F2 C25 C26 117.6(7) . . ?
C63 C62 C61 119.7(6) . . ?
C71 C76 C75 119.4(6) . . ?
C71 C72 C73 117.5(6) . . ?
C26 C27 C22 122.8(6) . . ?
C33 C34 C35 118.5(6) . . ?
C25 C24 C23 118.6(6) . . ?
C37 C36 C35 121.4(7) . . ?
C27 C26 C25 117.2(6) . . ?
C75 C74 C73 119.9(6) . . ?
C60 C65 C64 121.1(6) . . ?
C24 C23 C22 121.4(6) . . ?
C74 C73 C72 121.0(6) . . ?
C36 C35 C34 119.6(6) . . ?
C70 C67 C68 109.9(6) . . ?
C70 C67 C69 115.1(7) . . ?
C68 C67 C69 110.2(7) . . ?
C70 C67 S4 110.2(5) . . ?
C68 C67 S4 104.1(4) . . ?
C69 C67 S4 106.7(5) . . ?
C74 C75 C76 120.1(6) . . ?
C31 C29 C32 113.5(6) . . ?
C31 C29 C30 110.9(6) . . ?
C32 C29 C30 110.9(6) . . ?
C31 C29 S2 110.6(4) . . ?
C32 C29 S2 106.7(5) . . ?
C30 C29 S2 103.7(4) . . ?
C36 C37 C38 119.6(6) . . ?
O2 S1 N1 111.2(2) . . ?
O2 S1 C10 107.6(3) . . ?
N1 S1 C10 95.5(3) . . ?
O3 N2 C2 124.7(5) . . ?
O3 N2 C14 114.4(4) . . ?
C2 N2 C14 120.9(4) . . ?
C8 C3 C4 116.2(5) . . ?
C8 C3 C2 124.9(5) . . ?
C4 C3 C2 118.9(5) . . ?
N2 C2 C3 124.9(5) . . ?
N2 C2 C1 116.2(5) . . ?
C3 C2 C1 118.9(4) . . ?
C15 C14 C19 121.5(6) . . ?
C15 C14 N2 120.1(5) . . ?
C19 C14 N2 118.1(5) . . ?
N1 C1 O1 122.0(5) . . ?
N1 C1 C2 129.2(5) . . ?
O1 C1 C2 108.6(5) . . ?
C1 N1 S1 120.7(4) . . ?
C1 O1 C9 116.2(5) . . ?
C5 C4 C3 120.7(6) . . ?
C7 C6 C5 123.8(5) . . ?
C7 C6 F1 118.5(6) . . ?
C5 C6 F1 117.7(6) . . ?
C7 C8 C3 122.5(5) . . ?
C6 C7 C8 118.0(6) . . ?
C16 C17 C18 119.1(6) . . ?
C14 C19 C18 117.6(6) . . ?
C6 C5 C4 118.8(6) . . ?
C16 C15 C14 119.8(6) . . ?
C19 C18 C17 121.0(6) . . ?
C11 C10 C12 109.8(6) . . ?
C11 C10 C13 113.4(7) . . ?
C12 C10 C13 111.3(6) . . ?
C11 C10 S1 110.0(5) . . ?
C12 C10 S1 104.9(5) . . ?
C13 C10 S1 107.1(5) . . ?
C15 C16 C17 121.0(6) . . ?
O8 S3 N5 111.1(2) . . ?
O8 S3 C48 107.0(3) . . ?
N5 S3 C48 96.1(3) . . ?
N6 C40 C41 125.6(5) . . ?
N6 C40 C39 116.9(5) . . ?
C41 C40 C39 117.4(4) . . ?
C39 N5 S3 121.6(4) . . ?
O9 N6 C40 124.7(5) . . ?
O9 N6 C52 112.8(4) . . ?
C40 N6 C52 122.5(5) . . ?
C39 O7 C47 116.0(5) . . ?
C46 C41 C42 115.6(5) . . ?
C46 C41 C40 120.8(5) . . ?
C42 C41 C40 123.6(5) . . ?
C57 C52 C53 122.4(6) . . ?
C57 C52 N6 118.9(5) . . ?
C53 C52 N6 118.6(6) . . ?
N5 C39 O7 121.0(5) . . ?
N5 C39 C40 128.0(5) . . ?
O7 C39 C40 111.0(4) . . ?
C54 C53 C52 119.2(6) . . ?
C45 C46 C41 122.5(6) . . ?
C56 C55 C54 119.9(6) . . ?
C44 C45 C46 119.9(6) . . ?
C45 C44 C43 121.0(6) . . ?
C45 C44 F3 121.2(7) . . ?
C43 C44 F3 117.7(6) . . ?
C43 C42 C41 121.0(6) . . ?
C53 C54 C55 120.5(6) . . ?
C52 C57 C56 119.3(6) . . ?
C55 C56 C57 118.6(6) . . ?
C44 C43 C42 120.0(6) . . ?
C51 C48 C50 112.0(7) . . ?
C51 C48 C49 113.9(6) . . ?
C50 C48 C49 110.6(7) . . ?
C51 C48 S3 110.2(5) . . ?
C50 C48 S3 106.7(4) . . ?
C49 C48 S3 102.8(5) . . ?


####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1815457'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H16 N2 O2 S'
_chemical_formula_sum            'C16 H16 N2 O2 S'
_chemical_formula_weight         300.37
_chemical_absolute_configuration syn
_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 0.0033 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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   7.8609(12)
_cell_length_b                   10.9333(17)
_cell_length_c                   17.847(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1533.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1043
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.755
_cell_measurement_theta_min      2.283
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0601 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9347.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.108
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9463
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.184
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1856
_reflns_number_total             3516
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 558 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      0.985
_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)+(0.0431P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C8(H8), C7(H7), C12(H12), C13(H13), C6(H6), C16(H16),
 C15(H15), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C3(H3A,H3B,H3C)
;
_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
N2 N -0.2288(4) -0.6814(3) -0.1812(2) 0.0594(10) Uani 1 1 d . . . . .
C2 C -0.3611(4) -0.5981(3) -0.2078(2) 0.0461(10) Uani 1 1 d . . . . .
O1 O -0.3854(3) -0.4953(3) -0.32470(17) 0.0627(8) Uani 1 1 d . . . . .
N1 N -0.1408(5) -0.6015(3) -0.3031(2) 0.0698(11) Uani 1 1 d . . . . .
C1 C -0.2880(5) -0.5645(4) -0.2825(2) 0.0519(11) Uani 1 1 d . . . . .
C11 C -0.3775(6) -0.4817(3) -0.1601(2) 0.0558(11) Uani 1 1 d . . . . .
C4 C -0.2460(5) -0.7627(4) -0.1195(2) 0.0504(10) Uani 1 1 d . . . . .
C5 C -0.1763(5) -0.8786(4) -0.1237(3) 0.0663(13) Uani 1 1 d . . . . .
H5 H -0.1230 -0.9049 -0.1673 0.080 Uiso 1 1 calc R . . . .
C9 C -0.3307(5) -0.7285(4) -0.0554(2) 0.0581(11) Uani 1 1 d . . . . .
H9 H -0.3793 -0.6511 -0.0525 0.070 Uiso 1 1 calc R . . . .
C10 C -0.5290(4) -0.6668(4) -0.2174(2) 0.0600(11) Uani 1 1 d . . . . .
H10A H -0.5080 -0.7440 -0.2414 0.090 Uiso 1 1 calc GR . . . .
H10B H -0.6050 -0.6191 -0.2478 0.090 Uiso 1 1 calc GR . . . .
H10C H -0.5795 -0.6805 -0.1692 0.090 Uiso 1 1 calc GR . . . .
C8 C -0.3445(6) -0.8063(4) 0.0042(3) 0.0664(12) Uani 1 1 d . . . . .
H8 H -0.4032 -0.7822 0.0469 0.080 Uiso 1 1 calc R . . . .
C7 C -0.2715(6) -0.9202(5) 0.0008(3) 0.0791(15) Uani 1 1 d . . . . .
H7 H -0.2798 -0.9734 0.0413 0.095 Uiso 1 1 calc R . . . .
C12 C -0.5336(7) -0.4299(4) -0.1460(3) 0.0679(13) Uani 1 1 d . . . . .
H12 H -0.6315 -0.4661 -0.1651 0.081 Uiso 1 1 calc R . . . .
C13 C -0.5464(9) -0.3230(5) -0.1031(3) 0.0942(18) Uani 1 1 d . . . . .
H13 H -0.6515 -0.2873 -0.0935 0.113 Uiso 1 1 calc R . . . .
C3 C -0.3155(7) -0.4561(5) -0.3962(3) 0.0872(17) Uani 1 1 d . . . . .
H3A H -0.4033 -0.4181 -0.4255 0.131 Uiso 1 1 calc GR . . . .
H3B H -0.2717 -0.5258 -0.4226 0.131 Uiso 1 1 calc GR . . . .
H3C H -0.2253 -0.3986 -0.3877 0.131 Uiso 1 1 calc GR . . . .
C6 C -0.1869(6) -0.9545(4) -0.0622(4) 0.0836(17) Uani 1 1 d . . . . .
H6 H -0.1350 -1.0309 -0.0639 0.100 Uiso 1 1 calc R . . . .
C16 C -0.2331(7) -0.4260(5) -0.1335(3) 0.0928(18) Uani 1 1 d . . . . .
H16 H -0.1271 -0.4600 -0.1436 0.111 Uiso 1 1 calc R . . . .
C15 C -0.2442(10) -0.3194(6) -0.0918(4) 0.120(2) Uani 1 1 d . . . . .
H15 H -0.1463 -0.2803 -0.0750 0.144 Uiso 1 1 calc R . . . .
C14 C -0.3999(14) -0.2729(5) -0.0759(4) 0.118(3) Uani 1 1 d . . . . .
H14 H -0.4072 -0.2044 -0.0452 0.141 Uiso 1 1 calc R . . . .
S1 S -0.05149(15) -0.68475(15) -0.23433(8) 0.0911(5) Uani 1 1 d . . . . .
O2 O 0.0792(4) -0.6066(5) -0.1994(2) 0.1368(19) 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
N2 C2 1.462(5) . ?
N2 C4 1.421(5) . ?
N2 S1 1.686(3) . ?
C2 C1 1.497(5) . ?
C2 C11 1.537(5) . ?
C2 C10 1.528(5) . ?
O1 C1 1.314(4) . ?
O1 C3 1.454(5) . ?
N1 C1 1.279(5) . ?
N1 S1 1.681(4) . ?
C11 C12 1.374(6) . ?
C11 C16 1.373(6) . ?
C4 C5 1.382(5) . ?
C4 C9 1.376(5) . ?
C5 C6 1.379(7) . ?
C9 C8 1.366(5) . ?
C8 C7 1.372(6) . ?
C7 C6 1.360(7) . ?
C12 C13 1.401(6) . ?
C13 C14 1.365(9) . ?
C16 C15 1.386(8) . ?
C15 C14 1.355(8) . ?
S1 O2 1.474(5) . ?

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
C2 N2 S1 114.7(3) . . ?
C4 N2 C2 125.0(3) . . ?
C4 N2 S1 120.0(3) . . ?
N2 C2 C1 99.7(3) . . ?
N2 C2 C11 113.3(3) . . ?
N2 C2 C10 110.2(3) . . ?
C1 C2 C11 108.8(3) . . ?
C1 C2 C10 110.6(3) . . ?
C10 C2 C11 113.4(3) . . ?
C1 O1 C3 116.9(3) . . ?
C1 N1 S1 109.9(3) . . ?
O1 C1 C2 115.3(3) . . ?
N1 C1 C2 121.7(4) . . ?
N1 C1 O1 123.0(4) . . ?
C12 C11 C2 121.1(4) . . ?
C16 C11 C2 119.3(4) . . ?
C16 C11 C12 119.5(4) . . ?
C5 C4 N2 119.6(4) . . ?
C9 C4 N2 121.3(4) . . ?
C9 C4 C5 119.1(4) . . ?
C6 C5 C4 119.0(5) . . ?
C8 C9 C4 121.1(4) . . ?
C9 C8 C7 119.9(4) . . ?
C6 C7 C8 119.4(5) . . ?
C11 C12 C13 120.5(5) . . ?
C14 C13 C12 118.0(6) . . ?
C7 C6 C5 121.5(5) . . ?
C11 C16 C15 120.4(6) . . ?
C14 C15 C16 119.0(6) . . ?
C15 C14 C13 122.4(6) . . ?
N1 S1 N2 93.06(18) . . ?
O2 S1 N2 109.0(2) . . ?
O2 S1 N1 106.6(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1815455'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 N2 O3 S'
_chemical_formula_sum            'C19 H22 N2 O3 S'
_chemical_formula_weight         358.44
_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 0.0033 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'
S S 0.1246 0.1234 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   11.0074(4)
_cell_length_b                   11.0674(4)
_cell_length_c                   15.1861(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.889(3)
_cell_angle_gamma                90
_cell_volume                     1849.02(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6119
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1990
_cell_measurement_theta_min      2.6160
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13948
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.472
_diffrn_reflns_theta_min         2.250
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  82.00   1.00    1.70    --   11.74  57.00 120.00   97
  2  ω    -15.00  79.00   1.00    1.70    --   11.74  77.00-120.00   94
  3  ω    -58.00  35.00   1.00    1.70    --   11.74 -57.00 -30.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0347649000
_diffrn_orient_matrix_UB_12      -0.0044959000
_diffrn_orient_matrix_UB_13      0.0383547000
_diffrn_orient_matrix_UB_21      -0.0541884000
_diffrn_orient_matrix_UB_22      0.0001228000
_diffrn_orient_matrix_UB_23      -0.0265607000
_diffrn_orient_matrix_UB_31      0.0023714000
_diffrn_orient_matrix_UB_32      -0.0639764000
_diffrn_orient_matrix_UB_33      -0.0027523000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3682
_reflns_number_total             4492
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0087(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.040
_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)+(0.0448P)²+0.6185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C9(H9), C11(H11), C6(H6), C4(H4), C12(H12), C10(H10),
 C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C)
;
_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 0.70036(3) 0.83098(3) 0.86751(2) 0.01883(11) Uani 1 1 d . . . . .
O1 O 0.53722(9) 0.59130(9) 0.72819(7) 0.0219(2) Uani 1 1 d . . . . .
O2 O 0.74135(9) 0.90423(9) 0.79601(7) 0.0248(2) Uani 1 1 d . . . . .
O3 O 0.62395(9) 0.88650(9) 0.93056(7) 0.0261(2) Uani 1 1 d . . . . .
N1 N 0.63081(10) 0.70682(11) 0.83250(8) 0.0192(3) Uani 1 1 d . . . . .
N006 N 0.50679(11) 0.86324(11) 0.66923(8) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.69001(13) 0.77723(13) 0.61450(9) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.58997(13) 0.78401(13) 0.67758(9) 0.0196(3) Uani 1 1 d . . . . .
C14 C 0.59124(12) 0.69351(13) 0.75310(9) 0.0186(3) Uani 1 1 d . . . . .
C15 C 0.83068(13) 0.76638(14) 0.92546(10) 0.0229(3) Uani 1 1 d . . . . .
C8 C 0.41313(13) 0.87079(14) 0.73162(9) 0.0222(3) Uani 1 1 d . . . . .
C19 C 0.52423(15) 0.49953(13) 0.79612(10) 0.0259(3) Uani 1 1 d . . . . .
H19A H 0.480501 0.431585 0.771823 0.039 Uiso 1 1 calc GR . . . .
H19B H 0.480374 0.532760 0.844068 0.039 Uiso 1 1 calc GR . . . .
H19C H 0.603250 0.473834 0.817194 0.039 Uiso 1 1 calc GR . . . .
C13 C 0.40927(14) 0.97258(14) 0.78497(11) 0.0272(3) Uani 1 1 d . . . . .
H13 H 0.467050 1.033270 0.779867 0.033 Uiso 1 1 calc R . . . .
C2 C 0.69737(14) 0.86508(14) 0.54919(10) 0.0258(3) Uani 1 1 d . . . . .
H2 H 0.637728 0.924359 0.543622 0.031 Uiso 1 1 calc R . . . .
C9 C 0.32408(13) 0.78228(15) 0.73704(10) 0.0259(3) Uani 1 1 d . . . . .
H9 H 0.325974 0.714627 0.700779 0.031 Uiso 1 1 calc R . . . .
C11 C 0.23003(15) 0.89544(17) 0.85135(12) 0.0346(4) Uani 1 1 d . . . . .
H11 H 0.168731 0.903542 0.891645 0.041 Uiso 1 1 calc R . . . .
C6 C 0.77849(14) 0.68744(14) 0.62122(10) 0.0242(3) Uani 1 1 d . . . . .
H6 H 0.773540 0.627855 0.664131 0.029 Uiso 1 1 calc R . . . .
C4 C 0.88203(15) 0.77564(15) 0.50009(11) 0.0312(4) Uani 1 1 d . . . . .
H4 H 0.946793 0.775906 0.462270 0.037 Uiso 1 1 calc R . . . .
C16 C 0.90412(14) 0.87494(16) 0.96095(11) 0.0322(4) Uani 1 1 d . . . . .
H16A H 0.930632 0.922877 0.912525 0.048 Uiso 1 1 calc GR . . . .
H16B H 0.973620 0.846615 0.994779 0.048 Uiso 1 1 calc GR . . . .
H16C H 0.853999 0.923176 0.997725 0.048 Uiso 1 1 calc GR . . . .
C12 C 0.31845(15) 0.98320(16) 0.84607(11) 0.0322(4) Uani 1 1 d . . . . .
H12 H 0.317361 1.049693 0.883486 0.039 Uiso 1 1 calc R . . . .
C10 C 0.23234(14) 0.79540(17) 0.79683(11) 0.0322(4) Uani 1 1 d . . . . .
H10 H 0.172198 0.736723 0.800253 0.039 Uiso 1 1 calc R . . . .
C5 C 0.87424(14) 0.68693(14) 0.56371(11) 0.0285(4) Uani 1 1 d . . . . .
H5 H 0.933135 0.626789 0.568079 0.034 Uiso 1 1 calc R . . . .
C18 C 0.90371(14) 0.69187(15) 0.86130(11) 0.0298(4) Uani 1 1 d . . . . .
H18A H 0.856593 0.623356 0.841789 0.045 Uiso 1 1 calc GR . . . .
H18B H 0.977534 0.664568 0.890266 0.045 Uiso 1 1 calc GR . . . .
H18C H 0.922967 0.740799 0.811455 0.045 Uiso 1 1 calc GR . . . .
C17 C 0.78524(15) 0.68895(15) 1.00051(10) 0.0285(4) Uani 1 1 d . . . . .
H17A H 0.739531 0.738279 1.039513 0.043 Uiso 1 1 calc GR . . . .
H17B H 0.853346 0.654117 1.032425 0.043 Uiso 1 1 calc GR . . . .
H17C H 0.734197 0.625663 0.976889 0.043 Uiso 1 1 calc GR . . . .
C3 C 0.79324(15) 0.86422(15) 0.49269(11) 0.0313(4) Uani 1 1 d . . . . .
H3 H 0.798215 0.923376 0.449462 0.038 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 1.4395(11) . ?
S1 O3 1.4334(10) . ?
S1 N1 1.6523(12) . ?
S1 C15 1.8056(15) . ?
O1 C14 1.3273(17) . ?
O1 C19 1.4580(17) . ?
N1 C14 1.2770(18) . ?
N006 C7 1.2711(19) . ?
N006 C8 1.4254(18) . ?
C1 C7 1.4851(19) . ?
C1 C2 1.393(2) . ?
C1 C6 1.393(2) . ?
C7 C14 1.522(2) . ?
C15 C16 1.536(2) . ?
C15 C18 1.526(2) . ?
C15 C17 1.524(2) . ?
C8 C13 1.389(2) . ?
C8 C9 1.390(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C12 1.391(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C11 C10 1.383(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.391(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(2) . ?
C4 C3 1.386(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C5 H5 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 H3 0.9300 . ?

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 N1 112.27(6) . . ?
O2 S1 C15 109.08(7) . . ?
O3 S1 O2 117.90(7) . . ?
O3 S1 N1 107.19(6) . . ?
O3 S1 C15 108.57(7) . . ?
N1 S1 C15 100.35(6) . . ?
C14 O1 C19 116.46(11) . . ?
C14 N1 S1 122.67(10) . . ?
C7 N006 C8 120.56(13) . . ?
C2 C1 C7 119.06(13) . . ?
C6 C1 C7 121.36(13) . . ?
C6 C1 C2 119.55(13) . . ?
N006 C7 C1 121.17(13) . . ?
N006 C7 C14 121.18(13) . . ?
C1 C7 C14 117.65(12) . . ?
O1 C14 C7 110.68(12) . . ?
N1 C14 O1 120.21(13) . . ?
N1 C14 C7 129.04(13) . . ?
C16 C15 S1 105.17(11) . . ?
C18 C15 S1 109.25(10) . . ?
C18 C15 C16 111.39(13) . . ?
C17 C15 S1 108.19(10) . . ?
C17 C15 C16 111.07(13) . . ?
C17 C15 C18 111.51(13) . . ?
C13 C8 N006 118.15(14) . . ?
C13 C8 C9 120.12(14) . . ?
C9 C8 N006 121.66(14) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C13 H13 120.2 . . ?
C8 C13 C12 119.60(15) . . ?
C12 C13 H13 120.2 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.05(14) . . ?
C3 C2 H2 120.0 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.65(15) . . ?
C10 C9 H9 120.2 . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.13(15) . . ?
C10 C11 H11 119.9 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.97(14) . . ?
C5 C6 H6 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 119.94(14) . . ?
C3 C4 H4 120.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.22(16) . . ?
C11 C12 H12 119.9 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.24(16) . . ?
C11 C10 H10 119.9 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.13(15) . . ?
C4 C5 H5 119.9 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C3 C4 120.35(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1815456'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N2 O3 S'
_chemical_formula_sum            'C20 H26 N2 O3 S'
_chemical_formula_weight         374.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   9.546(18)
_cell_length_b                   8.931(17)
_cell_length_c                   12.96(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.93(2)
_cell_angle_gamma                90
_cell_volume                     1051(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    478
_cell_measurement_theta_min      2.3399
_cell_measurement_theta_max      16.3456

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7928
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0709 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.7928.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5330
_diffrn_reflns_av_unetI/netI     0.1118
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_point_group_measured_fraction_full 0.798
_reflns_number_total             2971
_reflns_number_gt                1473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.492
_reflns_Friedel_fraction_max     0.567
_reflns_Friedel_fraction_full    0.567

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0223P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0138(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(17)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2971
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.002
_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_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 0.16026(14) 0.27989(16) -0.52215(10) 0.0658(4) Uani 1 1 d . . . . .
O1 O 0.1273(3) 0.1155(4) -0.5216(2) 0.0785(12) Uani 1 1 d . . . . .
O2 O 0.5734(3) 0.3348(4) -0.3676(2) 0.0754(12) Uani 1 1 d . . . . .
O3 O 0.2825(4) 0.0779(4) -0.3120(3) 0.0701(11) Uani 1 1 d . . . . .
H3 H 0.2325 0.0461 -0.3713 0.105 Uiso 1 1 d R U . . .
N1 N 0.3464(4) 0.2970(5) -0.4859(3) 0.0612(11) Uani 1 1 d . . . . .
N2 N 0.2490(4) 0.2344(4) -0.3024(3) 0.0612(14) Uani 1 1 d . . . . .
C1 C -0.0335(5) 0.2978(7) -0.7202(4) 0.099(2) Uani 1 1 d . . . . .
H1A H -0.0523 0.1921 -0.7227 0.148 Uiso 1 1 calc R U . . .
H1B H -0.0609 0.3369 -0.7927 0.148 Uiso 1 1 calc R U . . .
H1C H -0.0901 0.3466 -0.6803 0.148 Uiso 1 1 calc R U . . .
C2 C 0.1593(6) 0.4939(7) -0.6670(4) 0.092(2) Uani 1 1 d . . . . .
H2A H 0.1069 0.5461 -0.6256 0.138 Uiso 1 1 calc R U . . .
H2B H 0.1270 0.5289 -0.7406 0.138 Uiso 1 1 calc R U . . .
H2C H 0.2630 0.5121 -0.6362 0.138 Uiso 1 1 calc R U . . .
C3 C 0.2259(6) 0.2344(7) -0.7155(4) 0.095(2) Uani 1 1 d . . . . .
H3A H 0.3267 0.2650 -0.6852 0.143 Uiso 1 1 calc R U . . .
H3B H 0.1948 0.2505 -0.7925 0.143 Uiso 1 1 calc R U . . .
H3C H 0.2170 0.1301 -0.7008 0.143 Uiso 1 1 calc R U . . .
C4 C 0.1294(6) 0.3261(6) -0.6648(4) 0.0700(18) Uani 1 1 d . . . . .
C5 C 0.6257(5) 0.3469(7) -0.4616(4) 0.091(2) Uani 1 1 d . . . . .
H5A H 0.7292 0.3691 -0.4381 0.136 Uiso 1 1 calc R U . . .
H5B H 0.5735 0.4257 -0.5081 0.136 Uiso 1 1 calc R U . . .
H5C H 0.6091 0.2539 -0.5007 0.136 Uiso 1 1 calc R U . . .
C6 C 0.4281(5) 0.3108(6) -0.3881(4) 0.0619(15) Uani 1 1 d . . . . .
C7 C 0.3906(5) 0.3197(6) -0.2810(4) 0.0585(15) Uani 1 1 d . . . . .
C8 C 0.3515(6) 0.4872(6) -0.2739(4) 0.0789(19) Uani 1 1 d . . . . .
H8A H 0.2776 0.5164 -0.3397 0.118 Uiso 1 1 calc R U . . .
H8B H 0.4380 0.5473 -0.2641 0.118 Uiso 1 1 calc R U . . .
H8C H 0.3145 0.5017 -0.2137 0.118 Uiso 1 1 calc R U . . .
C9 C 0.5086(5) 0.2594(6) -0.1837(4) 0.0629(16) Uani 1 1 d . . . . .
C10 C 0.5764(5) 0.1279(7) -0.1888(4) 0.0806(19) Uani 1 1 d . . . . .
H10 H 0.5572 0.0781 -0.2548 0.097 Uiso 1 1 calc R U . . .
C11 C 0.6753(6) 0.0664(7) -0.0952(4) 0.091(2) Uani 1 1 d . . . . .
H11 H 0.7211 -0.0242 -0.0998 0.109 Uiso 1 1 calc R U . . .
C12 C 0.7062(6) 0.1376(8) 0.0034(4) 0.094(2) Uani 1 1 d . . . . .
H12 H 0.7721 0.0956 0.0650 0.112 Uiso 1 1 calc R U . . .
C13 C 0.6393(6) 0.2698(8) 0.0097(4) 0.095(2) Uani 1 1 d . . . . .
H13 H 0.6591 0.3188 0.0760 0.114 Uiso 1 1 calc R U . . .
C14 C 0.5402(6) 0.3329(7) -0.0835(4) 0.083(2) Uani 1 1 d . . . . .
H14 H 0.4951 0.4238 -0.0788 0.100 Uiso 1 1 calc R U . . .
C15 C 0.1769(5) 0.2471(6) -0.2191(4) 0.0635(17) Uani 1 1 d . . . . .
C16 C 0.0572(6) 0.3398(6) -0.2389(4) 0.0760(18) Uani 1 1 d . . . . .
H16 H 0.0252 0.3937 -0.3033 0.091 Uiso 1 1 calc R U . . .
C17 C -0.0158(6) 0.3522(7) -0.1617(5) 0.096(2) Uani 1 1 d . . . . .
H17 H -0.0955 0.4170 -0.1738 0.115 Uiso 1 1 calc R U . . .
C18 C 0.0276(6) 0.2712(8) -0.0693(4) 0.104(2) Uani 1 1 d . . . . .
H18 H -0.0226 0.2805 -0.0184 0.125 Uiso 1 1 calc R U . . .
C19 C 0.1430(7) 0.1772(8) -0.0503(4) 0.100(2) Uani 1 1 d . . . . .
H19 H 0.1715 0.1221 0.0137 0.120 Uiso 1 1 calc R U . . .
C20 C 0.2208(6) 0.1610(7) -0.1255(4) 0.0758(18) Uani 1 1 d . . . . .
H20 H 0.2993 0.0945 -0.1130 0.091 Uiso 1 1 calc R U . . .


_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 1.502(5) . ?
S1 N1 1.699(5) . ?
S1 C4 1.827(6) . ?
O2 C6 1.347(6) . ?
O2 C5 1.457(6) . ?
O3 N2 1.448(5) . ?
O3 H3 0.8200 . ?
N1 C6 1.273(5) . ?
N2 C15 1.452(6) . ?
N2 C7 1.501(6) . ?
C1 C4 1.519(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.527(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.525(7) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.539(7) . ?
C7 C9 1.508(6) . ?
C7 C8 1.551(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.353(7) . ?
C9 C14 1.403(7) . ?
C10 C11 1.400(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.357(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.370(7) . ?
C15 C20 1.388(7) . ?
C16 C17 1.388(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.346(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.403(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 N1 106.8(2) . . ?
O1 S1 C4 104.9(2) . . ?
N1 S1 C4 95.1(2) . . ?
C6 O2 C5 116.4(4) . . ?
N2 O3 H3 109.6 . . ?
C6 N1 S1 123.5(3) . . ?
O3 N2 C15 107.9(4) . . ?
O3 N2 C7 107.2(4) . . ?
C15 N2 C7 115.4(4) . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 C3 111.9(4) . . ?
C1 C4 C2 109.0(4) . . ?
C3 C4 C2 112.2(5) . . ?
C1 C4 S1 105.3(4) . . ?
C3 C4 S1 112.6(3) . . ?
C2 C4 S1 105.5(4) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 O2 119.3(4) . . ?
N1 C6 C7 131.4(4) . . ?
O2 C6 C7 109.0(4) . . ?
N2 C7 C9 111.8(4) . . ?
N2 C7 C6 104.7(4) . . ?
C9 C7 C6 114.5(4) . . ?
N2 C7 C8 106.3(4) . . ?
C9 C7 C8 115.3(4) . . ?
C6 C7 C8 103.3(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 118.8(5) . . ?
C10 C9 C7 121.0(5) . . ?
C14 C9 C7 119.9(5) . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 121.2(6) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.2(5) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.2(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.4(6) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C16 C15 C20 120.5(5) . . ?
C16 C15 N2 117.8(4) . . ?
C20 C15 N2 121.5(5) . . ?
C15 C16 C17 119.3(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 120.7(6) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.4(6) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.1(6) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 117.9(5) . . ?
C15 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?

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 C6 -89.6(5) . . . . ?
C4 S1 N1 C6 163.1(5) . . . . ?
O1 S1 C4 C1 63.7(4) . . . . ?
N1 S1 C4 C1 172.6(4) . . . . ?
O1 S1 C4 C3 -58.5(4) . . . . ?
N1 S1 C4 C3 50.4(4) . . . . ?
O1 S1 C4 C2 178.9(4) . . . . ?
N1 S1 C4 C2 -72.2(4) . . . . ?
S1 N1 C6 O2 -175.1(4) . . . . ?
S1 N1 C6 C7 -1.6(9) . . . . ?
C5 O2 C6 N1 1.4(7) . . . . ?
C5 O2 C6 C7 -173.4(4) . . . . ?
O3 N2 C7 C9 -54.8(5) . . . . ?
C15 N2 C7 C9 65.3(5) . . . . ?
O3 N2 C7 C6 69.6(4) . . . . ?
C15 N2 C7 C6 -170.2(4) . . . . ?
O3 N2 C7 C8 178.6(3) . . . . ?
C15 N2 C7 C8 -61.2(5) . . . . ?
N1 C6 C7 N2 27.9(8) . . . . ?
O2 C6 C7 N2 -158.2(4) . . . . ?
N1 C6 C7 C9 150.6(6) . . . . ?
O2 C6 C7 C9 -35.4(6) . . . . ?
N1 C6 C7 C8 -83.2(7) . . . . ?
O2 C6 C7 C8 90.7(5) . . . . ?
N2 C7 C9 C10 73.6(6) . . . . ?
C6 C7 C9 C10 -45.1(7) . . . . ?
C8 C7 C9 C10 -164.8(5) . . . . ?
N2 C7 C9 C14 -100.5(6) . . . . ?
C6 C7 C9 C14 140.7(5) . . . . ?
C8 C7 C9 C14 21.0(7) . . . . ?
C14 C9 C10 C11 0.4(8) . . . . ?
C7 C9 C10 C11 -173.8(5) . . . . ?
C9 C10 C11 C12 -0.1(9) . . . . ?
C10 C11 C12 C13 0.0(9) . . . . ?
C11 C12 C13 C14 -0.1(9) . . . . ?
C12 C13 C14 C9 0.4(9) . . . . ?
C10 C9 C14 C13 -0.6(8) . . . . ?
C7 C9 C14 C13 173.7(5) . . . . ?
O3 N2 C15 C16 -137.2(4) . . . . ?
C7 N2 C15 C16 103.0(5) . . . . ?
O3 N2 C15 C20 38.5(6) . . . . ?
C7 N2 C15 C20 -81.3(6) . . . . ?
C20 C15 C16 C17 3.1(8) . . . . ?
N2 C15 C16 C17 178.8(4) . . . . ?
C15 C16 C17 C18 -1.8(8) . . . . ?
C16 C17 C18 C19 0.2(10) . . . . ?
C17 C18 C19 C20 0.1(10) . . . . ?
C16 C15 C20 C19 -2.8(8) . . . . ?
N2 C15 C20 C19 -178.4(5) . . . . ?
C18 C19 C20 C15 1.2(9) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_4r
_database_code_depnum_ccdc_archive 'CCDC 1815454'
_audit_update_record             
;
2018-01-08 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N2 O3 S'
_chemical_formula_sum            'C21 H26 N2 O3 S'
_chemical_formula_weight         386.50
_chemical_absolute_configuration ?
_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 0.0033 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'
S S 0.1246 0.1234 '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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   11.1348(2)
_cell_length_b                   11.1348(2)
_cell_length_c                   16.3745(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2030.17(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6203
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.0980
_cell_measurement_theta_min      2.5700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16972
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.472
_diffrn_reflns_theta_min         2.212
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  57.00   1.00    2.50    --  -11.59  57.00   0.00   93
  2  ω    -16.00  75.00   1.00    2.50    --   11.74  57.00 150.00   91
  3  ω      3.00  29.00   1.00    2.50    --  -11.59 -99.00 -30.00   26
  4  ω    -83.00  13.00   1.00    2.50    --  -11.59 -57.00-150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0345141000
_diffrn_orient_matrix_UB_12      0.0291024000
_diffrn_orient_matrix_UB_13      0.0305678000
_diffrn_orient_matrix_UB_21      0.0415934000
_diffrn_orient_matrix_UB_22      0.0191366000
_diffrn_orient_matrix_UB_23      -0.0301014000
_diffrn_orient_matrix_UB_31      -0.0337634000
_diffrn_orient_matrix_UB_32      0.0533236000
_diffrn_orient_matrix_UB_33      -0.0059133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.772
_reflns_number_gt                4285
_reflns_number_total             4854
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4854
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.053
_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)+(0.0321P)²+0.2203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0828
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C21(H21), C6(H6), C20(H20), C3(H3), C5(H5), C17(H17), C18(H18),
 C4(H4), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C15(H15A,H15B,
 H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.74217(6) 0.90388(6) 0.62306(4) 0.02024(15) Uani 1 1 d . . . . .
O3 O 0.81848(16) 0.87414(17) 0.55162(11) 0.0248(4) Uani 1 1 d . . . . .
O2 O 0.47855(16) 0.69308(17) 0.57327(11) 0.0226(4) Uani 1 1 d . . . . .
O1 O 0.58764(18) 0.98847(16) 0.49279(11) 0.0269(5) Uani 1 1 d . . . . .
N1 N 0.61211(19) 0.89359(19) 0.45053(13) 0.0186(5) Uani 1 1 d . . . . .
N2 N 0.62042(18) 0.81431(19) 0.62925(13) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.7977(2) 0.4764(2) 0.33867(16) 0.0215(6) Uani 1 1 d . . . . .
H2 H 0.838582 0.545261 0.322484 0.026 Uiso 1 1 calc R . . . .
C10 C 0.5712(2) 0.7703(2) 0.56641(16) 0.0193(5) Uani 1 1 d . . . . .
C16 C 0.6552(2) 0.9169(2) 0.36783(16) 0.0190(5) Uani 1 1 d . . . . .
C21 C 0.5787(3) 0.9691(2) 0.31226(16) 0.0233(6) Uani 1 1 d . . . . .
H21 H 0.500249 0.988333 0.326795 0.028 Uiso 1 1 calc R . . . .
C1 C 0.7276(2) 0.4780(2) 0.40907(15) 0.0175(5) Uani 1 1 d . . . . .
C9 C 0.6028(2) 0.7842(2) 0.47889(15) 0.0179(5) Uani 1 1 d . . . . .
C6 C 0.6649(2) 0.3749(2) 0.43133(16) 0.0217(6) Uani 1 1 d . . . . .
H6 H 0.615729 0.376048 0.477224 0.026 Uiso 1 1 calc R . . . .
C20 C 0.6208(3) 0.9925(2) 0.23395(18) 0.0283(7) Uani 1 1 d . . . . .
H20 H 0.570437 1.027468 0.195376 0.034 Uiso 1 1 calc R . . . .
C3 C 0.8066(3) 0.3724(3) 0.29279(17) 0.0272(6) Uani 1 1 d . . . . .
H3 H 0.853370 0.371762 0.245724 0.033 Uiso 1 1 calc R . . . .
C5 C 0.6750(3) 0.2709(2) 0.38600(17) 0.0277(6) Uani 1 1 d . . . . .
H5 H 0.634152 0.201941 0.401982 0.033 Uiso 1 1 calc R . . . .
C8 C 0.6175(2) 0.6736(2) 0.42783(15) 0.0186(5) Uani 1 1 d . . . . .
H8A H 0.635117 0.697079 0.372053 0.022 Uiso 1 1 calc R . . . .
H8B H 0.542449 0.629354 0.427500 0.022 Uiso 1 1 calc R . . . .
C17 C 0.7726(2) 0.8878(2) 0.34853(17) 0.0231(6) Uani 1 1 d . . . . .
H17 H 0.822760 0.852891 0.387236 0.028 Uiso 1 1 calc R . . . .
C7 C 0.7184(2) 0.5910(2) 0.45913(16) 0.0215(6) Uani 1 1 d . . . . .
H7A H 0.794272 0.633627 0.456980 0.026 Uiso 1 1 calc R . . . .
H7B H 0.702798 0.569989 0.515637 0.026 Uiso 1 1 calc R . . . .
C18 C 0.8141(3) 0.9118(3) 0.27042(17) 0.0277(6) Uani 1 1 d . . . . .
H18 H 0.892804 0.893295 0.256197 0.033 Uiso 1 1 calc R . . . .
C12 C 0.8204(2) 0.8340(2) 0.71141(16) 0.0223(6) Uani 1 1 d . . . . .
C13 C 0.9381(2) 0.9044(2) 0.71777(18) 0.0271(6) Uani 1 1 d . . . . .
H13A H 0.982268 0.896379 0.667729 0.041 Uiso 1 1 calc GR . . . .
H13B H 0.985040 0.873270 0.762150 0.041 Uiso 1 1 calc GR . . . .
H13C H 0.920721 0.987629 0.727428 0.041 Uiso 1 1 calc GR . . . .
C14 C 0.7440(3) 0.8528(3) 0.78719(17) 0.0294(6) Uani 1 1 d . . . . .
H14A H 0.727846 0.936932 0.793949 0.044 Uiso 1 1 calc GR . . . .
H14B H 0.786200 0.823295 0.834198 0.044 Uiso 1 1 calc GR . . . .
H14C H 0.669571 0.810120 0.781323 0.044 Uiso 1 1 calc GR . . . .
C4 C 0.7464(3) 0.2694(3) 0.31648(17) 0.0300(7) Uani 1 1 d . . . . .
H4 H 0.753753 0.199420 0.285914 0.036 Uiso 1 1 calc R . . . .
C11 C 0.4375(3) 0.6687(3) 0.65542(17) 0.0272(6) Uani 1 1 d . . . . .
H11A H 0.374181 0.610222 0.653781 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.407990 0.741512 0.679602 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.502992 0.638240 0.687404 0.041 Uiso 1 1 calc GR . . . .
C15 C 0.8434(3) 0.7021(2) 0.69320(18) 0.0269(6) Uani 1 1 d . . . . .
H15A H 0.768594 0.659123 0.693793 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.896005 0.669309 0.733934 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.879958 0.694439 0.640367 0.040 Uiso 1 1 calc GR . . . .
C19 C 0.7377(3) 0.9635(2) 0.21363(18) 0.0289(7) Uani 1 1 d . . . . .
H19 H 0.765480 0.978942 0.161108 0.035 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 O3 1.4832(19) . ?
S1 N2 1.686(2) . ?
S1 C12 1.859(3) . ?
O2 C10 1.348(3) . ?
O2 C11 1.446(3) . ?
O1 N1 1.292(3) . ?
N1 C16 1.460(3) . ?
N1 C9 1.308(3) . ?
N2 C10 1.265(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.393(4) . ?
C2 C3 1.384(4) . ?
C10 C9 1.483(4) . ?
C16 C21 1.376(4) . ?
C16 C17 1.383(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(4) . ?
C1 C6 1.392(4) . ?
C1 C7 1.505(4) . ?
C9 C8 1.497(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.540(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.386(4) . ?
C12 C13 1.530(4) . ?
C12 C14 1.519(4) . ?
C12 C15 1.521(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 H4 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C19 H19 0.9300 . ?

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
O3 S1 N2 112.08(11) . . ?
O3 S1 C12 104.59(11) . . ?
N2 S1 C12 94.73(12) . . ?
C10 O2 C11 116.1(2) . . ?
O1 N1 C16 114.9(2) . . ?
O1 N1 C9 123.7(2) . . ?
C9 N1 C16 121.4(2) . . ?
C10 N2 S1 121.91(18) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
O2 C10 C9 109.2(2) . . ?
N2 C10 O2 120.7(2) . . ?
N2 C10 C9 130.0(2) . . ?
C21 C16 N1 119.0(2) . . ?
C21 C16 C17 122.2(2) . . ?
C17 C16 N1 118.7(2) . . ?
C16 C21 H21 120.6 . . ?
C16 C21 C20 118.7(3) . . ?
C20 C21 H21 120.6 . . ?
C2 C1 C7 120.0(2) . . ?
C6 C1 C2 119.2(2) . . ?
C6 C1 C7 120.9(2) . . ?
N1 C9 C10 117.3(2) . . ?
N1 C9 C8 124.0(2) . . ?
C10 C9 C8 118.7(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 H6 119.7 . . ?
C21 C20 H20 120.1 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C6 C5 H5 120.1 . . ?
C6 C5 C4 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C9 C8 C7 112.7(2) . . ?
H8A C8 H8B 107.8 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.7(3) . . ?
C18 C17 H17 120.6 . . ?
C1 C7 C8 111.6(2) . . ?
C1 C7 H7A 109.3 . . ?
C1 C7 H7B 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C13 C12 S1 103.88(18) . . ?
C14 C12 S1 108.39(19) . . ?
C14 C12 C13 110.7(2) . . ?
C14 C12 C15 112.8(2) . . ?
C15 C12 S1 109.29(19) . . ?
C15 C12 C13 111.4(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.717
