# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_x-2-16
_database_code_depnum_ccdc_archive 'CCDC 2309003'
loop_
_audit_author_name
_audit_author_address
'Martin Banwell'
;Jinan University
China
;
_audit_update_record             
;
2023-11-20 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3178(10)
_cell_length_b                   13.776(3)
_cell_length_c                   16.414(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1654.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    399
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      59.7610
_cell_measurement_theta_min      6.5890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58680
_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            'light colourless'
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.1701
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4102
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.365
_diffrn_reflns_theta_min         4.190
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  80.00   1.00    8.00    --   40.73 -99.00 150.00   48
  2  ω     32.00 132.00   1.00   10.00    --  107.58 -30.00   0.00  100
  3  ω     68.00 102.00   1.00   10.00    --  107.58 -94.00 -30.00   34
  4  ω     27.00  65.00   1.00   10.00    --  107.58 -94.00 -30.00   38
  5  ω     36.00  64.00   1.00    8.00    --   40.73  38.00-180.00   28
  6  ω    114.00 148.00   1.00   10.00    --  107.58  45.00-150.00   34
  7  ω    106.00 133.00   1.00   10.00    --  107.58 125.00 -90.00   27
  8  ω    123.00 176.00   1.00   10.00    --  107.58 125.00  30.00   53
  9  ω   -108.00 -21.00   1.00    8.00    --  -40.73 -38.00-180.00   87
;
_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      0.0223224000
_diffrn_orient_matrix_UB_12      -0.0701277000
_diffrn_orient_matrix_UB_13      0.0726165000
_diffrn_orient_matrix_UB_21      -0.0152956000
_diffrn_orient_matrix_UB_22      -0.0872604000
_diffrn_orient_matrix_UB_23      -0.0581176000
_diffrn_orient_matrix_UB_31      0.2087357000
_diffrn_orient_matrix_UB_32      0.0009038000
_diffrn_orient_matrix_UB_33      -0.0122522000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.446
_reflns_Friedel_fraction_full    0.641
_reflns_Friedel_fraction_max     0.584
_reflns_number_gt                1898
_reflns_number_total             2704
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(8)
_refine_ls_extinction_coef       0.00103(12)
_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   0.803
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1732
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      0.805
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1704
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C14, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C13 \\sim C14: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C6(H6), C9(H9), C11(H11), C16(H16)
4.b X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
4.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_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
O3 O -0.0216(3) 0.44617(19) 0.6444(2) 0.0587(10) Uani 1 1 d . . . . .
O2 O 0.6321(2) 0.7914(2) 0.6122(2) 0.0643(11) Uani 1 1 d . . . . .
N1 N 0.0096(3) 0.7942(2) 0.6040(2) 0.0487(11) Uani 1 1 d . . . . .
H1 H -0.103625 0.809955 0.599326 0.058 Uiso 1 1 calc R U . . .
C1 C 0.2661(5) 0.5324(3) 0.6427(3) 0.0519(14) Uani 1 1 d . . . . .
C2 C 0.3545(6) 0.4427(3) 0.6658(3) 0.0668(17) Uani 1 1 d . . . . .
H2 H 0.476728 0.443487 0.681360 0.080 Uiso 1 1 calc R U . . .
C3 C 0.2629(6) 0.3583(3) 0.6652(4) 0.0699(19) Uani 1 1 d . . . . .
H3 H 0.318523 0.302481 0.685127 0.084 Uiso 1 1 calc R U . . .
C4 C 0.0744(5) 0.3534(3) 0.6331(3) 0.0582(16) Uani 1 1 d . . . . .
C5 C 0.0732(4) 0.5316(3) 0.6328(3) 0.0459(13) Uani 1 1 d . . . . .
C6 C -0.0226(4) 0.6141(3) 0.6207(3) 0.0465(14) Uani 1 1 d . . . . .
H6 H -0.149500 0.613132 0.617992 0.056 Uiso 1 1 calc R U . . .
C7 C 0.0734(4) 0.7004(3) 0.6123(3) 0.0435(12) Uani 1 1 d . . . . .
C8 C 0.2657(4) 0.7047(3) 0.6181(3) 0.0435(13) Uani 1 1 d . . . . .
C9 C 0.3598(4) 0.6197(3) 0.6336(3) 0.0545(15) Uani 1 1 d . . . . .
H9 H 0.486459 0.620878 0.637997 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3120(4) 0.8067(3) 0.6101(3) 0.0457(12) Uani 1 1 d . . . . .
C11 C 0.4968(4) 0.8420(3) 0.6090(3) 0.0610(16) Uani 1 1 d . . . . .
H11 H 0.513880 0.908736 0.605483 0.073 Uiso 1 1 calc R U . . .
C12 C 0.1512(4) 0.8580(3) 0.6043(3) 0.0458(13) Uani 1 1 d . . . . .
C13 C 0.1175(4) 0.9675(3) 0.6019(3) 0.0493(10) Uani 1 1 d . U . . .
C14 C 0.1755(5) 1.0071(3) 0.5190(3) 0.0578(11) Uani 1 1 d . U . . .
H14A H 0.304969 0.999105 0.512422 0.087 Uiso 1 1 calc R U . . .
H14B H 0.145075 1.074741 0.515648 0.087 Uiso 1 1 calc R U . . .
H14C H 0.112828 0.972262 0.476696 0.087 Uiso 1 1 calc R U . . .
C15 C -0.0898(4) 0.9879(3) 0.6110(3) 0.0665(17) Uani 1 1 d . . . . .
H15A H -0.153500 0.962940 0.564350 0.100 Uiso 1 1 calc R U . . .
H15B H -0.109616 1.056631 0.614903 0.100 Uiso 1 1 calc R U . . .
H15C H -0.134670 0.956792 0.659351 0.100 Uiso 1 1 calc R U . . .
C16 C 0.2134(5) 1.0125(3) 0.6725(3) 0.0530(14) Uani 1 1 d . . . . .
H16 H 0.184312 0.989773 0.724267 0.064 Uiso 1 1 calc R U . . .
C17 C 0.3403(6) 1.0843(3) 0.6670(3) 0.0745(18) Uani 1 1 d . . . . .
H17A H 0.372959 1.108854 0.616249 0.089 Uiso 1 1 calc R U . . .
H17B H 0.394466 1.108826 0.713917 0.089 Uiso 1 1 calc R U . . .
C18 C -0.0484(6) 0.2804(3) 0.6761(3) 0.0790(19) Uani 1 1 d . . . . .
H18A H -0.048933 0.293420 0.733548 0.119 Uiso 1 1 calc R U . . .
H18B H -0.003278 0.215898 0.666657 0.119 Uiso 1 1 calc R U . . .
H18C H -0.170538 0.285675 0.655186 0.119 Uiso 1 1 calc R U . . .
C19 C 0.0796(6) 0.3333(3) 0.5418(3) 0.0698(17) Uani 1 1 d . . . . .
H19A H -0.042988 0.328584 0.521347 0.105 Uiso 1 1 calc R U . . .
H19B H 0.142907 0.273461 0.531967 0.105 Uiso 1 1 calc R U . . .
H19C H 0.142053 0.385365 0.514632 0.105 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
O3 C4 1.470(5) . ?
O3 C5 1.380(5) . ?
O2 C11 1.212(4) . ?
N1 H1 0.8600 . ?
N1 C7 1.381(5) . ?
N1 C12 1.359(4) . ?
C1 C2 1.445(6) . ?
C1 C5 1.421(5) . ?
C1 C9 1.393(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.342(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.478(6) . ?
C4 C18 1.523(6) . ?
C4 C19 1.524(7) . ?
C5 C6 1.350(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(5) . ?
C7 C8 1.412(4) . ?
C8 C9 1.382(5) . ?
C8 C10 1.451(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.437(5) . ?
C10 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.529(5) . ?
C13 C14 1.526(6) . ?
C13 C15 1.550(4) . ?
C13 C16 1.490(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.360(6) . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C5 O3 C4 119.0(3) . . ?
C7 N1 H1 124.8 . . ?
C12 N1 H1 124.8 . . ?
C12 N1 C7 110.3(3) . . ?
C5 C1 C2 117.9(4) . . ?
C9 C1 C2 123.1(3) . . ?
C9 C1 C5 118.9(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
O3 C4 C3 111.2(4) . . ?
O3 C4 C18 103.5(3) . . ?
O3 C4 C19 107.1(4) . . ?
C3 C4 C18 114.6(4) . . ?
C3 C4 C19 109.6(4) . . ?
C18 C4 C19 110.5(4) . . ?
O3 C5 C1 119.3(4) . . ?
C6 C5 O3 118.5(3) . . ?
C6 C5 C1 121.8(4) . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.2(3) . . ?
C7 C6 H6 120.9 . . ?
N1 C7 C6 129.8(3) . . ?
N1 C7 C8 107.7(3) . . ?
C6 C7 C8 122.3(4) . . ?
C7 C8 C10 105.5(3) . . ?
C9 C8 C7 118.2(3) . . ?
C9 C8 C10 136.1(3) . . ?
C1 C9 H9 119.8 . . ?
C8 C9 C1 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C8 123.2(3) . . ?
C12 C10 C8 107.7(3) . . ?
C12 C10 C11 129.1(4) . . ?
O2 C11 C10 125.0(4) . . ?
O2 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
N1 C12 C10 108.7(3) . . ?
N1 C12 C13 121.0(3) . . ?
C10 C12 C13 130.2(3) . . ?
C12 C13 C15 109.5(3) . . ?
C14 C13 C12 109.3(4) . . ?
C14 C13 C15 107.0(4) . . ?
C16 C13 C12 108.4(4) . . ?
C16 C13 C14 114.5(3) . . ?
C16 C13 C15 108.1(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16 117.5 . . ?
C17 C16 C13 124.9(5) . . ?
C17 C16 H16 117.5 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C5 C6 C7 177.4(4) . . . . ?
N1 C7 C8 C9 174.7(4) . . . . ?
N1 C7 C8 C10 -1.8(5) . . . . ?
N1 C12 C13 C14 -109.5(4) . . . . ?
N1 C12 C13 C15 7.5(6) . . . . ?
N1 C12 C13 C16 125.2(4) . . . . ?
C1 C2 C3 C4 6.1(8) . . . . ?
C1 C5 C6 C7 4.5(7) . . . . ?
C2 C1 C5 O3 -0.8(7) . . . . ?
C2 C1 C5 C6 172.2(5) . . . . ?
C2 C1 C9 C8 -174.6(5) . . . . ?
C2 C3 C4 O3 -29.5(7) . . . . ?
C2 C3 C4 C18 -146.4(5) . . . . ?
C2 C3 C4 C19 88.7(6) . . . . ?
C4 O3 C5 C1 -25.1(6) . . . . ?
C4 O3 C5 C6 161.8(4) . . . . ?
C5 O3 C4 C3 39.0(6) . . . . ?
C5 O3 C4 C18 162.5(4) . . . . ?
C5 O3 C4 C19 -80.7(5) . . . . ?
C5 C1 C2 C3 10.5(8) . . . . ?
C5 C1 C9 C8 2.3(7) . . . . ?
C5 C6 C7 N1 -176.1(5) . . . . ?
C5 C6 C7 C8 -1.6(7) . . . . ?
C6 C7 C8 C9 -0.8(7) . . . . ?
C6 C7 C8 C10 -177.3(4) . . . . ?
C7 N1 C12 C10 2.0(5) . . . . ?
C7 N1 C12 C13 -175.7(4) . . . . ?
C7 C8 C9 C1 0.4(7) . . . . ?
C7 C8 C10 C11 -177.0(4) . . . . ?
C7 C8 C10 C12 2.9(5) . . . . ?
C8 C10 C11 O2 2.1(8) . . . . ?
C8 C10 C12 N1 -3.0(5) . . . . ?
C8 C10 C12 C13 174.4(5) . . . . ?
C9 C1 C2 C3 -172.6(5) . . . . ?
C9 C1 C5 O3 -177.8(4) . . . . ?
C9 C1 C5 C6 -4.9(8) . . . . ?
C9 C8 C10 C11 7.4(9) . . . . ?
C9 C8 C10 C12 -172.6(6) . . . . ?
C10 C8 C9 C1 175.5(5) . . . . ?
C10 C12 C13 C14 73.4(6) . . . . ?
C10 C12 C13 C15 -169.6(5) . . . . ?
C10 C12 C13 C16 -51.9(6) . . . . ?
C11 C10 C12 N1 177.0(5) . . . . ?
C11 C10 C12 C13 -5.7(9) . . . . ?
C12 N1 C7 C6 175.0(5) . . . . ?
C12 N1 C7 C8 0.0(5) . . . . ?
C12 C10 C11 O2 -177.9(5) . . . . ?
C12 C13 C16 C17 123.5(4) . . . . ?
C14 C13 C16 C17 1.2(6) . . . . ?
C15 C13 C16 C17 -117.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.549
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.8782 3824 333 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.1218 3916 333 nmt -0.8445 -0.2226 0.1474 -0.2593 -0.3862 -0.7604 1.1400
-0.9693 0.2553

_twin_special_details            
;
Component 2 rotated by 169.6148° 
 around [0.13 -0.49 0.86] (reciprocal) or [0.49 -0.55 0.67] (direct)
;
####################################################################### 
# 
# 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_x-1-145
_database_code_depnum_ccdc_archive 'CCDC 2309004'
loop_
_audit_author_name
_audit_author_address
'Martin Banwell'
;Jinan University
China
;
_audit_update_record             
;
2023-11-20 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-05-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O3 S'
_chemical_formula_sum            'C14 H15 N O3 S'
_chemical_formula_weight         277.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.8280(5)
_cell_length_b                   9.9624(4)
_cell_length_c                   10.6981(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.793(4)
_cell_angle_gamma                90
_cell_volume                     1354.57(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3687
_cell_measurement_temperature    169.91(16)
_cell_measurement_theta_max      73.4250
_cell_measurement_theta_min      3.4480
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66699
_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            'light yellow'
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5201
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.746
_diffrn_reflns_theta_min         3.478
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.91(16)
_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 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  41.00   1.00    1.00    --   40.73 -99.00 -60.00   38
  2  ω     24.00  96.00   1.00    1.00    --   40.73-125.00 -60.00   72
  3  ω     37.00 109.00   1.00    1.00    --  107.58 -94.00 -60.00   72
  4  ω     52.00 126.00   1.00    1.00    --  107.58 -61.00   0.00   74
  5  ω     52.00 119.00   1.00    1.00    --  107.58-125.00 -60.00   67
  6  ω     40.00 122.00   1.00    1.00    --  107.58 -45.00  60.00   82
  7  ω     23.00  59.00   1.00    1.00    --   40.73-125.00-150.00   36
  8  ω     75.00 143.00   1.00    1.00    --  107.58  77.00-150.00   68
  9  ω    103.00 128.00   1.00    1.00    --  107.58 125.00-180.00   25
 10  ω     95.00 135.00   1.00    1.00    --  107.58 125.00  30.00   40
 11  ω   -121.00 -26.00   1.00    1.00    --  -40.73 -19.00  30.00   95
;
_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      -0.0824404000
_diffrn_orient_matrix_UB_12      -0.0721106000
_diffrn_orient_matrix_UB_13      0.0680089000
_diffrn_orient_matrix_UB_21      -0.0849461000
_diffrn_orient_matrix_UB_22      0.0989775000
_diffrn_orient_matrix_UB_23      -0.0593197000
_diffrn_orient_matrix_UB_31      -0.0259419000
_diffrn_orient_matrix_UB_32      -0.0946487000
_diffrn_orient_matrix_UB_33      -0.1138155000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2432
_reflns_number_total             2665
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.058
_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)+(0.0622P)²+0.2468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1083
_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. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
 Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(2)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(2)
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(3)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(3)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C8(H8), C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C13A(H13D,H13E,
 H13F), C14A(H14D,H14E,H14F)
;
_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
S001 S 0.57687(3) 0.62195(4) 0.29883(3) 0.03682(16) Uani 1 1 d . . . . .
C1 C 0.78270(14) 0.68699(17) 0.29779(16) 0.0431(4) Uani 1 1 d . . . . .
H1 H 0.773557 0.722819 0.216770 0.052 Uiso 1 1 calc R U . . .
N1 N 0.70280(10) 0.63229(13) 0.35961(12) 0.0374(3) Uani 1 1 d . . . . .
O1 O 0.7205(3) 0.4580(15) 0.7887(9) 0.042(2) Uani 0.50(3) 1 d . . P A 1
O2 O 0.57347(10) 0.64695(14) 0.16764(11) 0.0513(3) Uani 1 1 d . . . . .
C2 C 0.87453(13) 0.67930(18) 0.37448(16) 0.0448(4) Uani 1 1 d . . . . .
H2 H 0.939330 0.708814 0.355413 0.054 Uiso 1 1 calc R U . . .
O3 O 0.53907(9) 0.49782(13) 0.34098(12) 0.0486(3) Uani 1 1 d . . . . .
C3 C 0.85589(12) 0.61790(15) 0.49071(15) 0.0361(3) Uani 1 1 d . . . . .
C4 C 0.74753(11) 0.59035(15) 0.48023(14) 0.0337(3) Uani 1 1 d . . . . .
C5 C 0.70125(11) 0.52908(18) 0.57534(15) 0.0407(4) Uani 1 1 d . . . . .
H5 H 0.629037 0.514745 0.567857 0.049 Uiso 1 1 calc R U . . .
C6 C 0.76767(12) 0.49047(19) 0.68157(16) 0.0431(4) Uani 1 1 d . . . . .
C7 C 0.87732(11) 0.51371(17) 0.69514(15) 0.0378(3) Uani 1 1 d . . . . .
C8 C 0.92006(11) 0.57862(17) 0.60014(15) 0.0384(3) Uani 1 1 d . . . . .
H8 H 0.991893 0.596186 0.609172 0.046 Uiso 1 1 calc R U . . .
C9 C 0.93996(13) 0.4672(2) 0.81066(17) 0.0499(4) Uani 1 1 d . . . . .
H9 H 1.012284 0.481343 0.822874 0.060 Uiso 1 1 calc R U . . .
C10 C 0.89478(14) 0.4049(2) 0.89838(17) 0.0502(4) Uani 1 1 d . . . . .
H10 H 0.936811 0.376306 0.971220 0.060 Uiso 1 1 calc R U . . .
C11 C 0.77871(14) 0.37821(18) 0.88554(16) 0.0448(4) Uani 1 1 d . . . . .
C12 C 0.51656(16) 0.7524(2) 0.36926(17) 0.0549(5) Uani 1 1 d . . . . .
H12A H 0.528989 0.742279 0.459289 0.082 Uiso 1 1 calc R U . . .
H12B H 0.442229 0.750674 0.341317 0.082 Uiso 1 1 calc R U . . .
H12C H 0.545119 0.836513 0.346131 0.082 Uiso 1 1 calc R U . . .
C13 C 0.7495(4) 0.2395(4) 0.9187(6) 0.0670(16) Uani 0.563(10) 1 d . . P A 1
H13A H 0.674594 0.234027 0.917269 0.100 Uiso 0.563(10) 1 calc R U P A 1
H13B H 0.783715 0.217552 1.001585 0.100 Uiso 0.563(10) 1 calc R U P A 1
H13C H 0.771192 0.177437 0.858636 0.100 Uiso 0.563(10) 1 calc R U P A 1
C14 C 0.7326(3) 0.4819(6) 0.9719(5) 0.0610(14) Uani 0.591(10) 1 d . . P A 1
H14A H 0.750555 0.570995 0.948290 0.092 Uiso 0.591(10) 1 calc R U P A 1
H14B H 0.761251 0.465748 1.058223 0.092 Uiso 0.591(10) 1 calc R U P A 1
H14C H 0.657404 0.472795 0.962537 0.092 Uiso 0.591(10) 1 calc R U P A 1
O1A O 0.7248(4) 0.3974(16) 0.7573(8) 0.044(2) Uani 0.50(3) 1 d . . P A 2
C13A C 0.7719(4) 0.2305(5) 0.8344(9) 0.066(2) Uani 0.437(10) 1 d . . P A 2
H13D H 0.700688 0.199188 0.828991 0.099 Uiso 0.437(10) 1 calc R U P A 2
H13E H 0.816947 0.173770 0.890746 0.099 Uiso 0.437(10) 1 calc R U P A 2
H13F H 0.794019 0.228123 0.752225 0.099 Uiso 0.437(10) 1 calc R U P A 2
C14A C 0.7287(5) 0.3898(12) 1.0019(5) 0.074(3) Uani 0.409(10) 1 d . . P A 2
H14D H 0.740598 0.478145 1.036702 0.112 Uiso 0.409(10) 1 calc R U P A 2
H14E H 0.758551 0.324365 1.062222 0.112 Uiso 0.409(10) 1 calc R U P A 2
H14F H 0.654382 0.374379 0.982127 0.112 Uiso 0.409(10) 1 calc R U P A 2


_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
S001 N1 1.6608(13) . ?
S001 O2 1.4202(12) . ?
S001 O3 1.4237(12) . ?
S001 C12 1.7362(18) . ?
C1 H1 0.9300 . ?
C1 N1 1.4031(19) . ?
C1 C2 1.343(3) . ?
N1 C4 1.4029(19) . ?
O1 C6 1.404(5) . ?
O1 C11 1.433(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.435(2) . ?
C3 C4 1.406(2) . ?
C3 C8 1.393(2) . ?
C4 C5 1.387(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(2) . ?
C6 C7 1.413(2) . ?
C6 O1A 1.392(5) . ?
C7 C8 1.379(2) . ?
C7 C9 1.456(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.323(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.500(2) . ?
C11 C13 1.487(4) . ?
C11 C14 1.555(4) . ?
C11 O1A 1.463(5) . ?
C11 C13A 1.568(6) . ?
C11 C14A 1.480(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 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 S001 C12 104.51(8) . . ?
O2 S001 N1 105.90(7) . . ?
O2 S001 O3 119.95(8) . . ?
O2 S001 C12 109.99(9) . . ?
O3 S001 N1 106.55(7) . . ?
O3 S001 C12 108.78(9) . . ?
N1 C1 H1 125.5 . . ?
C2 C1 H1 125.5 . . ?
C2 C1 N1 109.04(14) . . ?
C1 N1 S001 125.00(11) . . ?
C4 N1 S001 126.62(10) . . ?
C4 N1 C1 108.38(13) . . ?
C6 O1 C11 118.5(4) . . ?
C1 C2 H2 125.7 . . ?
C1 C2 C3 108.55(14) . . ?
C3 C2 H2 125.7 . . ?
C4 C3 C2 107.05(14) . . ?
C8 C3 C2 134.37(15) . . ?
C8 C3 C4 118.51(14) . . ?
N1 C4 C3 106.97(13) . . ?
C5 C4 N1 130.04(13) . . ?
C5 C4 C3 122.96(14) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 C4 116.68(14) . . ?
C6 C5 H5 121.7 . . ?
O1 C6 C7 119.1(3) . . ?
C5 C6 O1 116.74(19) . . ?
C5 C6 C7 122.26(14) . . ?
C5 C6 O1A 114.62(19) . . ?
O1A C6 C7 121.0(3) . . ?
C6 C7 C9 117.52(15) . . ?
C8 C7 C6 119.38(14) . . ?
C8 C7 C9 123.10(14) . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.15(14) . . ?
C7 C8 H8 119.9 . . ?
C7 C9 H9 119.8 . . ?
C10 C9 C7 120.49(15) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 118.6 . . ?
C9 C10 C11 122.89(15) . . ?
C11 C10 H10 118.6 . . ?
O1 C11 C10 112.4(2) . . ?
O1 C11 C13 124.4(6) . . ?
O1 C11 C14 81.8(6) . . ?
C10 C11 C14 106.3(2) . . ?
C10 C11 C13A 101.9(2) . . ?
C13 C11 C10 115.0(2) . . ?
C13 C11 C14 110.3(4) . . ?
O1A C11 C10 113.6(2) . . ?
O1A C11 C13A 78.4(7) . . ?
O1A C11 C14A 125.1(5) . . ?
C14A C11 C10 116.6(3) . . ?
C14A C11 C13A 110.9(6) . . ?
S001 C12 H12A 109.5 . . ?
S001 C12 H12B 109.5 . . ?
S001 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 O1A C11 117.3(5) . . ?
C11 C13A H13D 109.5 . . ?
C11 C13A H13E 109.5 . . ?
C11 C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C11 C14A H14D 109.5 . . ?
C11 C14A H14E 109.5 . . ?
C11 C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 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
S001 N1 C4 C3 179.77(11) . . . . ?
S001 N1 C4 C5 1.6(3) . . . . ?
C1 N1 C4 C3 -0.98(17) . . . . ?
C1 N1 C4 C5 -179.10(17) . . . . ?
C1 C2 C3 C4 -0.60(19) . . . . ?
C1 C2 C3 C8 176.26(18) . . . . ?
N1 C1 C2 C3 0.0(2) . . . . ?
N1 C4 C5 C6 175.41(17) . . . . ?
O1 C6 C7 C8 -163.2(7) . . . . ?
O1 C6 C7 C9 16.7(8) . . . . ?
O2 S001 N1 C1 14.01(16) . . . . ?
O2 S001 N1 C4 -166.86(13) . . . . ?
C2 C1 N1 S001 179.89(13) . . . . ?
C2 C1 N1 C4 0.61(19) . . . . ?
C2 C3 C4 N1 0.96(17) . . . . ?
C2 C3 C4 C5 179.25(16) . . . . ?
C2 C3 C8 C7 -176.32(17) . . . . ?
O3 S001 N1 C1 142.77(14) . . . . ?
O3 S001 N1 C4 -38.09(15) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C3 C8 C7 0.3(2) . . . . ?
C4 C5 C6 O1 165.5(8) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C4 C5 C6 O1A -162.5(8) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C5 C6 C7 C9 -179.26(17) . . . . ?
C5 C6 O1A C11 -164.6(8) . . . . ?
C6 O1 C11 C10 33.1(14) . . . . ?
C6 O1 C11 C13 -113.5(9) . . . . ?
C6 O1 C11 C14 137.4(12) . . . . ?
C6 C7 C8 C3 -1.5(2) . . . . ?
C6 C7 C9 C10 0.4(3) . . . . ?
C7 C6 O1A C11 31.6(16) . . . . ?
C7 C9 C10 C11 0.0(3) . . . . ?
C8 C3 C4 N1 -176.49(14) . . . . ?
C8 C3 C4 C5 1.8(2) . . . . ?
C8 C7 C9 C10 -179.67(18) . . . . ?
C9 C7 C8 C3 178.57(16) . . . . ?
C9 C10 C11 O1 -16.3(8) . . . . ?
C9 C10 C11 C13 133.6(3) . . . . ?
C9 C10 C11 C14 -104.1(3) . . . . ?
C9 C10 C11 O1A 13.9(8) . . . . ?
C9 C10 C11 C13A 96.3(4) . . . . ?
C9 C10 C11 C14A -142.9(5) . . . . ?
C10 C11 O1A C6 -28.8(14) . . . . ?
C11 O1 C6 C5 160.3(8) . . . . ?
C11 O1 C6 C7 -34.8(15) . . . . ?
C12 S001 N1 C1 -102.15(15) . . . . ?
C12 S001 N1 C4 76.99(15) . . . . ?
O1A C6 C7 C8 163.4(8) . . . . ?
O1A C6 C7 C9 -16.7(9) . . . . ?
C13A C11 O1A C6 -126.9(12) . . . . ?
C14A C11 O1A C6 125.7(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.693
