# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_(rac)-3aa_exp_192_hp
_database_code_depnum_ccdc_archive 'CCDC 2087721'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_audit_creation_date             2019-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            (rac)-3aa
_chemical_name_systematic        
(E)-5-(hex-2-en-1-yl)-4,5-diphenyl-5H-1,2,3-oxathiazole-2,2,-dioxide
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H21NO3S
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9169(3)
_cell_length_b                   10.0932(3)
_cell_length_c                   10.9734(4)
_cell_angle_alpha                82.217(3)
_cell_angle_beta                 83.123(3)
_cell_angle_gamma                67.004(3)
_cell_volume                     898.33(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10939
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.6180
_cell_measurement_theta_min      2.4760
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.48a (Rigaku Oxford Diffraction, 2019)
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    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method 'Et2O evaporation'
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23029
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         2.202
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50    4.00    --   20.00  54.00 -26.84  368
  2  ω    -74.00 110.00   0.50    4.00    --   20.00  54.00 -26.84  368
  3  ω    -74.00 110.00   0.50    4.00    --   20.00  54.00-129.88  368
  4  ω    -74.00 110.00   0.50    4.00    --   20.00  54.00  30.00  368
  5  ω    -74.00 110.00   0.50    4.00    --   20.00  54.00  86.03  368
  6  ω    -74.00 110.00   0.50    4.00    --   20.00  54.00-180.00  368
  7  ω    -74.00 110.00   0.50    4.00    --   20.00  54.00 -90.00  368
  8  ω    -74.00 110.00   0.50    4.00    --   20.00  54.00 -60.00  368
  9  ω    -74.00 -66.50   0.50    4.00    --   20.00  54.00 -60.00   15
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0121738000
_diffrn_orient_matrix_UB_12      -0.0380026000
_diffrn_orient_matrix_UB_13      -0.0453000000
_diffrn_orient_matrix_UB_21      -0.0189544000
_diffrn_orient_matrix_UB_22      -0.0476543000
_diffrn_orient_matrix_UB_23      0.0471832000
_diffrn_orient_matrix_UB_31      -0.0836662000
_diffrn_orient_matrix_UB_32      0.0465642000
_diffrn_orient_matrix_UB_33      0.0008659000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4661
_reflns_number_total             5236
_reflns_odcompleteness_completeness 95.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.48a (Rigaku OD, 2019)'
_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         0.426
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.047
_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)+(0.0544P)²+0.2355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0981
_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:
 C1H(H1HA,H1HB), C4H(H4HA,H4HB), C5H(H5HA,H5HB)
2.b Aromatic/amide H refined with riding coordinates:
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C52(H52), C53(H53),
 C54(H54), C55(H55), C56(H56), C2H(H2H), C3H(H3H)
2.c Idealised Me refined as rotating group:
 C6H(H6HA,H6HB,H6HC)
;
_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
S2 S 0.34854(3) 0.67601(2) 0.31152(2) 0.02295(7) Uani 1 1 d . . . . .
O1 O 0.43369(9) 0.58583(7) 0.19632(6) 0.02097(14) Uani 1 1 d . . . . .
O2 O 0.21111(11) 0.79943(8) 0.27238(9) 0.0359(2) Uani 1 1 d . . . . .
O3 O 0.46854(11) 0.69827(9) 0.37166(8) 0.03366(19) Uani 1 1 d . . . . .
N3 N 0.28969(11) 0.55481(9) 0.39693(8) 0.02174(16) Uani 1 1 d . . . . .
C4 C 0.33904(11) 0.43744(9) 0.34331(8) 0.01664(16) Uani 1 1 d . . . . .
C5 C 0.43135(11) 0.43962(9) 0.21604(8) 0.01671(16) Uani 1 1 d . . . . .
C41 C 0.30130(11) 0.31269(10) 0.40078(8) 0.01777(17) Uani 1 1 d . . . . .
C42 C 0.18792(12) 0.33197(11) 0.50337(9) 0.02324(19) Uani 1 1 d . . . . .
H42 H 0.138724 0.423764 0.534795 0.028 Uiso 1 1 calc R . . . .
C43 C 0.14714(14) 0.21771(13) 0.55927(10) 0.0300(2) Uani 1 1 d . . . . .
H43 H 0.069806 0.231426 0.628641 0.036 Uiso 1 1 calc R . . . .
C44 C 0.21922(15) 0.08330(13) 0.51397(11) 0.0332(2) Uani 1 1 d . . . . .
H44 H 0.190741 0.005279 0.552309 0.040 Uiso 1 1 calc R . . . .
C45 C 0.33223(15) 0.06240(12) 0.41332(12) 0.0323(2) Uani 1 1 d . . . . .
H45 H 0.381634 -0.029997 0.382989 0.039 Uiso 1 1 calc R . . . .
C46 C 0.37379(13) 0.17643(11) 0.35635(10) 0.0249(2) Uani 1 1 d . . . . .
H46 H 0.451491 0.161775 0.287180 0.030 Uiso 1 1 calc R . . . .
C51 C 0.60834(11) 0.33385(10) 0.21569(9) 0.01888(17) Uani 1 1 d . . . . .
C52 C 0.70135(13) 0.33228(11) 0.31001(10) 0.0253(2) Uani 1 1 d . . . . .
H52 H 0.653427 0.396061 0.372549 0.030 Uiso 1 1 calc R . . . .
C53 C 0.86368(14) 0.23780(13) 0.31272(12) 0.0339(3) Uani 1 1 d . . . . .
H53 H 0.926675 0.237785 0.376682 0.041 Uiso 1 1 calc R . . . .
C54 C 0.93408(14) 0.14349(12) 0.22235(14) 0.0380(3) Uani 1 1 d . . . . .
H54 H 1.044635 0.077904 0.224953 0.046 Uiso 1 1 calc R . . . .
C55 C 0.84258(16) 0.14539(13) 0.12845(13) 0.0386(3) Uani 1 1 d . . . . .
H55 H 0.890878 0.081068 0.066345 0.046 Uiso 1 1 calc R . . . .
C56 C 0.68006(14) 0.24086(12) 0.12408(10) 0.0283(2) Uani 1 1 d . . . . .
H56 H 0.618457 0.242362 0.058650 0.034 Uiso 1 1 calc R . . . .
C1H C 0.33130(12) 0.42898(11) 0.11542(8) 0.02176(18) Uani 1 1 d . . . . .
H1HA H 0.386645 0.441809 0.033525 0.026 Uiso 1 1 calc R . . . .
H1HB H 0.328017 0.331168 0.125258 0.026 Uiso 1 1 calc R . . . .
C2H C 0.15934(12) 0.53975(11) 0.11987(9) 0.02315(19) Uani 1 1 d . . . . .
H2H H 0.143169 0.638028 0.095301 0.028 Uiso 1 1 calc R . . . .
C3H C 0.02866(13) 0.50788(11) 0.15627(9) 0.02333(19) Uani 1 1 d . . . . .
H3H H 0.047716 0.409307 0.182179 0.028 Uiso 1 1 calc R . . . .
C4H C -0.14589(13) 0.61226(12) 0.16045(9) 0.0248(2) Uani 1 1 d . . . . .
H4HA H -0.189782 0.616311 0.247709 0.030 Uiso 1 1 calc R . . . .
H4HB H -0.209215 0.573669 0.117328 0.030 Uiso 1 1 calc R . . . .
C5H C -0.17527(14) 0.76574(13) 0.10386(11) 0.0306(2) Uani 1 1 d . . . . .
H5HA H -0.137653 0.763968 0.015258 0.037 Uiso 1 1 calc R . . . .
H5HB H -0.110201 0.804826 0.144544 0.037 Uiso 1 1 calc R . . . .
C6H C -0.35504(16) 0.86479(15) 0.11737(14) 0.0421(3) Uani 1 1 d . . . . .
H6HA H -0.370210 0.960298 0.074367 0.063 Uiso 1 1 calc GR . . . .
H6HB H -0.389950 0.874288 0.204987 0.063 Uiso 1 1 calc GR . . . .
H6HC H -0.420563 0.823498 0.081454 0.063 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
S2 O1 1.5953(7) . ?
S2 O2 1.4235(8) . ?
S2 O3 1.4240(9) . ?
S2 N3 1.6503(9) . ?
O1 C5 1.4702(11) . ?
N3 C4 1.2894(11) . ?
C4 C5 1.5360(12) . ?
C4 C41 1.4702(12) . ?
C5 C51 1.5211(13) . ?
C5 C1H 1.5393(13) . ?
C41 C42 1.4001(13) . ?
C41 C46 1.3995(13) . ?
C42 H42 0.9500 . ?
C42 C43 1.3860(14) . ?
C43 H43 0.9500 . ?
C43 C44 1.3877(18) . ?
C44 H44 0.9500 . ?
C44 C45 1.3822(17) . ?
C45 H45 0.9500 . ?
C45 C46 1.3913(14) . ?
C46 H46 0.9500 . ?
C51 C52 1.3964(14) . ?
C51 C56 1.3904(13) . ?
C52 H52 0.9500 . ?
C52 C53 1.3891(15) . ?
C53 H53 0.9500 . ?
C53 C54 1.3868(19) . ?
C54 H54 0.9500 . ?
C54 C55 1.383(2) . ?
C55 H55 0.9500 . ?
C55 C56 1.3943(16) . ?
C56 H56 0.9500 . ?
C1H H1HA 0.9900 . ?
C1H H1HB 0.9900 . ?
C1H C2H 1.5037(14) . ?
C2H H2H 0.9500 . ?
C2H C3H 1.3295(14) . ?
C3H H3H 0.9500 . ?
C3H C4H 1.4998(14) . ?
C4H H4HA 0.9900 . ?
C4H H4HB 0.9900 . ?
C4H C5H 1.5216(16) . ?
C5H H5HA 0.9900 . ?
C5H H5HB 0.9900 . ?
C5H C6H 1.5239(17) . ?
C6H H6HA 0.9800 . ?
C6H H6HB 0.9800 . ?
C6H H6HC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S2 N3 98.46(4) . . ?
O2 S2 O1 108.75(5) . . ?
O2 S2 O3 118.11(5) . . ?
O2 S2 N3 110.80(5) . . ?
O3 S2 O1 109.60(5) . . ?
O3 S2 N3 109.32(5) . . ?
C5 O1 S2 111.84(5) . . ?
C4 N3 S2 110.15(7) . . ?
N3 C4 C5 116.10(8) . . ?
N3 C4 C41 120.70(8) . . ?
C41 C4 C5 123.15(7) . . ?
O1 C5 C4 103.37(7) . . ?
O1 C5 C51 106.92(7) . . ?
O1 C5 C1H 106.71(7) . . ?
C4 C5 C1H 110.31(7) . . ?
C51 C5 C4 112.36(7) . . ?
C51 C5 C1H 116.15(8) . . ?
C42 C41 C4 118.42(8) . . ?
C46 C41 C4 122.44(8) . . ?
C46 C41 C42 119.13(9) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 C41 120.29(10) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 120.0 . . ?
C42 C43 C44 120.04(10) . . ?
C44 C43 H43 120.0 . . ?
C43 C44 H44 119.8 . . ?
C45 C44 C43 120.31(10) . . ?
C45 C44 H44 119.8 . . ?
C44 C45 H45 119.9 . . ?
C44 C45 C46 120.12(10) . . ?
C46 C45 H45 119.9 . . ?
C41 C46 H46 119.9 . . ?
C45 C46 C41 120.11(10) . . ?
C45 C46 H46 119.9 . . ?
C52 C51 C5 118.44(8) . . ?
C56 C51 C5 122.15(9) . . ?
C56 C51 C52 119.40(9) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 C51 120.24(10) . . ?
C53 C52 H52 119.9 . . ?
C52 C53 H53 119.9 . . ?
C54 C53 C52 120.21(11) . . ?
C54 C53 H53 119.9 . . ?
C53 C54 H54 120.2 . . ?
C55 C54 C53 119.67(11) . . ?
C55 C54 H54 120.2 . . ?
C54 C55 H55 119.7 . . ?
C54 C55 C56 120.60(11) . . ?
C56 C55 H55 119.7 . . ?
C51 C56 C55 119.86(11) . . ?
C51 C56 H56 120.1 . . ?
C55 C56 H56 120.1 . . ?
C5 C1H H1HA 109.0 . . ?
C5 C1H H1HB 109.0 . . ?
H1HA C1H H1HB 107.8 . . ?
C2H C1H C5 112.83(8) . . ?
C2H C1H H1HA 109.0 . . ?
C2H C1H H1HB 109.0 . . ?
C1H C2H H2H 118.2 . . ?
C3H C2H C1H 123.68(9) . . ?
C3H C2H H2H 118.2 . . ?
C2H C3H H3H 116.8 . . ?
C2H C3H C4H 126.40(10) . . ?
C4H C3H H3H 116.8 . . ?
C3H C4H H4HA 108.3 . . ?
C3H C4H H4HB 108.3 . . ?
C3H C4H C5H 115.90(9) . . ?
H4HA C4H H4HB 107.4 . . ?
C5H C4H H4HA 108.3 . . ?
C5H C4H H4HB 108.3 . . ?
C4H C5H H5HA 109.2 . . ?
C4H C5H H5HB 109.2 . . ?
C4H C5H C6H 111.92(10) . . ?
H5HA C5H H5HB 107.9 . . ?
C6H C5H H5HA 109.2 . . ?
C6H C5H H5HB 109.2 . . ?
C5H C6H H6HA 109.5 . . ?
C5H C6H H6HB 109.5 . . ?
C5H C6H H6HC 109.5 . . ?
H6HA C6H H6HB 109.5 . . ?
H6HA C6H H6HC 109.5 . . ?
H6HB C6H H6HC 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
S2 O1 C5 C4 1.75(8) . . . . ?
S2 O1 C5 C51 -117.00(7) . . . . ?
S2 O1 C5 C1H 118.09(7) . . . . ?
S2 N3 C4 C5 -2.11(11) . . . . ?
S2 N3 C4 C41 -179.69(7) . . . . ?
O1 S2 N3 C4 2.84(8) . . . . ?
O1 C5 C51 C52 65.32(10) . . . . ?
O1 C5 C51 C56 -113.83(9) . . . . ?
O1 C5 C1H C2H -59.31(10) . . . . ?
O2 S2 O1 C5 -118.14(7) . . . . ?
O2 S2 N3 C4 116.67(8) . . . . ?
O3 S2 O1 C5 111.39(7) . . . . ?
O3 S2 N3 C4 -111.46(8) . . . . ?
N3 S2 O1 C5 -2.69(7) . . . . ?
N3 C4 C5 O1 0.29(11) . . . . ?
N3 C4 C5 C51 115.20(9) . . . . ?
N3 C4 C5 C1H -113.48(9) . . . . ?
N3 C4 C41 C42 10.87(13) . . . . ?
N3 C4 C41 C46 -169.44(9) . . . . ?
C4 C5 C51 C52 -47.41(11) . . . . ?
C4 C5 C51 C56 133.43(9) . . . . ?
C4 C5 C1H C2H 52.31(10) . . . . ?
C4 C41 C42 C43 179.11(9) . . . . ?
C4 C41 C46 C45 -179.23(10) . . . . ?
C5 C4 C41 C42 -166.54(9) . . . . ?
C5 C4 C41 C46 13.15(14) . . . . ?
C5 C51 C52 C53 -179.69(9) . . . . ?
C5 C51 C56 C55 -179.65(10) . . . . ?
C5 C1H C2H C3H -108.87(11) . . . . ?
C41 C4 C5 O1 177.80(8) . . . . ?
C41 C4 C5 C51 -67.28(11) . . . . ?
C41 C4 C5 C1H 64.04(11) . . . . ?
C41 C42 C43 C44 0.26(16) . . . . ?
C42 C41 C46 C45 0.46(15) . . . . ?
C42 C43 C44 C45 0.21(18) . . . . ?
C43 C44 C45 C46 -0.35(18) . . . . ?
C44 C45 C46 C41 0.01(17) . . . . ?
C46 C41 C42 C43 -0.60(15) . . . . ?
C51 C5 C1H C2H -178.39(8) . . . . ?
C51 C52 C53 C54 -0.56(16) . . . . ?
C52 C51 C56 C55 1.20(15) . . . . ?
C52 C53 C54 C55 0.94(17) . . . . ?
C53 C54 C55 C56 -0.24(18) . . . . ?
C54 C55 C56 C51 -0.83(18) . . . . ?
C56 C51 C52 C53 -0.51(15) . . . . ?
C1H C5 C51 C52 -175.72(8) . . . . ?
C1H C5 C51 C56 5.13(13) . . . . ?
C1H C2H C3H C4H -178.65(9) . . . . ?
C2H C3H C4H C5H 7.30(15) . . . . ?
C3H C4H C5H C6H -177.62(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen mount + Paratone'
_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 1.161
_oxdiff_exptl_absorpt_empirical_full_min 0.920
####################################################################### 
# 
# 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_4aa_exp_193_hp
_database_code_depnum_ccdc_archive 'CCDC 2087722'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_audit_creation_date             2021-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            4aa
_chemical_name_systematic        
'(E)-3-(hex-2-en-1-yl)-4,5-diphenyl-3H-1,2,3-oxathiazole 2,2-dioxide'
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H21N1O3S1
_chemical_oxdiff_usercomment     E39_N-allylated
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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.4602(2)
_cell_length_b                   10.8079(3)
_cell_length_c                   19.9865(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1827.51(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9401
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.2530
_cell_measurement_theta_min      2.6080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
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    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'n-hexane / Et2O'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25213
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         2.142
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 
'Hybrid Pixel Array Detector HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50    8.00    --   20.00  54.00-180.00  368
  2  ω    -74.00 110.00   0.50    8.00    --   20.00  54.00 -90.00  368
  3  ω    -74.00 110.00   0.50    8.00    --   20.00  54.00-150.00  368
  4  ω    -74.00 110.00   0.50    8.00    --   20.00  54.00  90.00  368
  5  ω    -74.00 -14.00   0.50    8.00    --   20.00  54.00   0.00  120
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0745310000
_diffrn_orient_matrix_UB_12      -0.0287696000
_diffrn_orient_matrix_UB_13      -0.0045899000
_diffrn_orient_matrix_UB_21      0.0124440000
_diffrn_orient_matrix_UB_22      0.0005320000
_diffrn_orient_matrix_UB_23      0.0350913000
_diffrn_orient_matrix_UB_31      -0.0362969000
_diffrn_orient_matrix_UB_32      -0.0590071000
_diffrn_orient_matrix_UB_33      0.0025531000
_diffrn_oxdiff_digest_frames     
;
01a1e9ca629c856e4e0eee49d0f02f582b015924c7d
;
_diffrn_oxdiff_digest_hkl        
;
013201017eaa2287495ce3a68e8db58a5ba2d7
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4349
_reflns_number_total             5129
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         -0.283
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5129
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.067
_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)+(0.0443P)²+0.1702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0906
_refine_special_details          'Refined as an inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.80(8)
 0.20(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C5-C4 = C5A-C4
 1.5 with sigma of 0.01
 C6-C5 = C6A-C5A
 1.53 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
5. Others
 Sof(H4BC)=Sof(H4BD)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=
 Sof(H6AC)=1-FVAR(1)
 Sof(H4AA)=Sof(H4AB)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=
 Sof(H6C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4AA,H4AB), C4(H4BC,H4BD), C5(H5A,H5B), C5A(H5AA,H5AB)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C52(H52),
 C53(H53), C54(H54), C55(H55), C56(H56)
6.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC)
;
_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
S2 S 0.24326(7) 0.52779(5) 0.85034(3) 0.03396(14) Uani 1 1 d . . . . .
O1 O 0.32887(17) 0.65032(13) 0.87631(7) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.2780(2) 0.43161(14) 0.89633(8) 0.0501(5) Uani 1 1 d . . . . .
O3 O 0.08326(19) 0.55569(19) 0.83568(9) 0.0560(5) Uani 1 1 d . . . . .
N3 N 0.3496(2) 0.51148(16) 0.78165(9) 0.0290(4) Uani 1 1 d . . . . .
C1 C 0.2682(3) 0.5173(2) 0.71556(10) 0.0355(5) Uani 1 1 d . . . . .
H1A H 0.332267 0.474510 0.682632 0.043 Uiso 1 1 calc R . . . .
H1B H 0.168086 0.473873 0.718861 0.043 Uiso 1 1 calc R . . . .
C2 C 0.2380(3) 0.6457(2) 0.69174(11) 0.0377(5) Uani 1 1 d . . . . .
H2 H 0.165771 0.694042 0.715130 0.045 Uiso 1 1 calc R . . . .
C3 C 0.3094(3) 0.6947(3) 0.63860(12) 0.0468(6) Uani 1 1 d . . . . .
H3 H 0.383094 0.645466 0.616648 0.056 Uiso 1 1 calc R . . . .
C4 C 0.2826(4) 0.8198(3) 0.61125(13) 0.0590(8) Uani 1 1 d D U . . .
H4AA H 0.381683 0.864533 0.608212 0.071 Uiso 0.576(7) 1 calc R . P A 1
H4AB H 0.211276 0.865881 0.639939 0.071 Uiso 0.576(7) 1 calc R . P A 1
H4BC H 0.369734 0.870561 0.626727 0.071 Uiso 0.424(7) 1 calc R . P A 3
H4BD H 0.188246 0.851357 0.632923 0.071 Uiso 0.424(7) 1 calc R . P A 3
C5 C 0.2084(9) 0.8031(6) 0.5401(3) 0.0540(17) Uani 0.576(7) 1 d D U P A 1
H5A H 0.276451 0.751849 0.512571 0.065 Uiso 0.576(7) 1 calc R . P A 1
H5B H 0.106115 0.763107 0.543606 0.065 Uiso 0.576(7) 1 calc R . P A 1
C5A C 0.2636(12) 0.8468(10) 0.5360(4) 0.064(3) Uani 0.424(7) 1 d D . P A 3
H5AA H 0.260617 0.935223 0.527812 0.077 Uiso 0.424(7) 1 calc R . P A 3
H5AB H 0.350026 0.811035 0.510711 0.077 Uiso 0.424(7) 1 calc R . P A 3
C6 C 0.1904(7) 0.9295(5) 0.5090(2) 0.0622(18) Uani 0.576(7) 1 d D U P A 1
H6A H 0.143316 0.921492 0.465502 0.093 Uiso 0.576(7) 1 calc GR . P A 1
H6B H 0.292449 0.967598 0.504816 0.093 Uiso 0.576(7) 1 calc GR . P A 1
H6C H 0.124025 0.979858 0.536842 0.093 Uiso 0.576(7) 1 calc GR . P A 1
C6A C 0.1062(10) 0.7864(7) 0.5169(3) 0.059(2) Uani 0.424(7) 1 d D . P A 3
H6AA H 0.088086 0.796883 0.469844 0.089 Uiso 0.424(7) 1 calc GR . P A 3
H6AB H 0.022002 0.824698 0.541562 0.089 Uiso 0.424(7) 1 calc GR . P A 3
H6AC H 0.109923 0.699748 0.527357 0.089 Uiso 0.424(7) 1 calc GR . P A 3
C7 C 0.4818(2) 0.65481(18) 0.84613(10) 0.0245(4) Uani 1 1 d . . . . .
C8 C 0.4901(2) 0.58289(18) 0.79145(9) 0.0249(4) Uani 1 1 d . . . . .
C41 C 0.6209(2) 0.56676(18) 0.74349(9) 0.0249(4) Uani 1 1 d . . . . .
C42 C 0.6920(3) 0.6694(2) 0.71395(11) 0.0313(4) Uani 1 1 d . . . . .
H42 H 0.657147 0.748605 0.724536 0.038 Uiso 1 1 calc R . . . .
C43 C 0.8149(3) 0.6534(2) 0.66865(11) 0.0360(5) Uani 1 1 d . . . . .
H43 H 0.862200 0.721942 0.648956 0.043 Uiso 1 1 calc R . . . .
C44 C 0.8671(2) 0.5353(2) 0.65274(11) 0.0351(5) Uani 1 1 d . . . . .
H44 H 0.950128 0.524871 0.622784 0.042 Uiso 1 1 calc R . . . .
C45 C 0.7956(3) 0.4331(2) 0.68146(11) 0.0337(5) Uani 1 1 d . . . . .
H45 H 0.830831 0.353997 0.670760 0.040 Uiso 1 1 calc R . . . .
C46 C 0.6715(2) 0.44807(19) 0.72615(10) 0.0295(4) Uani 1 1 d . . . . .
H46 H 0.622132 0.379128 0.744538 0.035 Uiso 1 1 calc R . . . .
C51 C 0.5968(3) 0.72900(18) 0.88336(10) 0.0270(4) Uani 1 1 d . . . . .
C52 C 0.5443(3) 0.82338(19) 0.92613(10) 0.0328(5) Uani 1 1 d . . . . .
H52 H 0.436841 0.839552 0.930492 0.039 Uiso 1 1 calc R . . . .
C53 C 0.6539(3) 0.8926(2) 0.96192(11) 0.0391(6) Uani 1 1 d . . . . .
H53 H 0.618802 0.955249 0.990120 0.047 Uiso 1 1 calc R . . . .
C54 C 0.8136(3) 0.8699(2) 0.95640(11) 0.0410(6) Uani 1 1 d . . . . .
H54 H 0.885700 0.917558 0.980270 0.049 Uiso 1 1 calc R . . . .
C55 C 0.8662(3) 0.7750(2) 0.91470(11) 0.0386(5) Uani 1 1 d . . . . .
H55 H 0.973726 0.758417 0.911189 0.046 Uiso 1 1 calc R . . . .
C56 C 0.7580(3) 0.70520(18) 0.87836(10) 0.0316(4) Uani 1 1 d . . . . .
H56 H 0.793686 0.642164 0.850522 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
S2 O1 1.5961(15) . ?
S2 O2 1.4183(17) . ?
S2 O3 1.4175(19) . ?
S2 N3 1.6507(17) . ?
O1 C7 1.428(2) . ?
N3 C1 1.491(3) . ?
N3 C8 1.431(3) . ?
C1 C2 1.490(3) . ?
C2 C3 1.332(4) . ?
C3 C4 1.475(4) . ?
C4 C5 1.565(6) . ?
C4 C5A 1.540(8) . ?
C5 C6 1.509(7) . ?
C5A C6A 1.531(9) . ?
C7 C8 1.343(3) . ?
C7 C51 1.464(3) . ?
C8 C41 1.474(3) . ?
C41 C42 1.393(3) . ?
C41 C46 1.396(3) . ?
C42 C43 1.389(3) . ?
C43 C44 1.387(3) . ?
C44 C45 1.385(3) . ?
C45 C46 1.388(3) . ?
C51 C52 1.403(3) . ?
C51 C56 1.392(3) . ?
C52 C53 1.389(3) . ?
C53 C54 1.377(4) . ?
C54 C55 1.394(3) . ?
C55 C56 1.391(3) . ?

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 S2 N3 96.42(8) . . ?
O2 S2 O1 107.67(10) . . ?
O2 S2 N3 110.36(10) . . ?
O3 S2 O1 108.91(10) . . ?
O3 S2 O2 119.18(13) . . ?
O3 S2 N3 111.78(10) . . ?
C7 O1 S2 107.57(11) . . ?
C1 N3 S2 118.72(14) . . ?
C8 N3 S2 106.34(13) . . ?
C8 N3 C1 118.85(17) . . ?
C2 C1 N3 113.66(16) . . ?
C3 C2 C1 123.2(2) . . ?
C2 C3 C4 126.2(3) . . ?
C3 C4 C5 107.0(3) . . ?
C3 C4 C5A 123.5(5) . . ?
C6 C5 C4 108.1(5) . . ?
C6A C5A C4 104.7(6) . . ?
O1 C7 C51 113.95(16) . . ?
C8 C7 O1 111.82(17) . . ?
C8 C7 C51 134.08(19) . . ?
N3 C8 C41 118.09(16) . . ?
C7 C8 N3 112.32(17) . . ?
C7 C8 C41 129.57(18) . . ?
C42 C41 C8 120.35(18) . . ?
C42 C41 C46 119.61(18) . . ?
C46 C41 C8 120.01(18) . . ?
C43 C42 C41 120.00(19) . . ?
C44 C43 C42 120.2(2) . . ?
C45 C44 C43 120.00(19) . . ?
C44 C45 C46 120.26(19) . . ?
C45 C46 C41 119.94(19) . . ?
C52 C51 C7 119.85(19) . . ?
C56 C51 C7 120.91(18) . . ?
C56 C51 C52 119.2(2) . . ?
C53 C52 C51 119.6(2) . . ?
C54 C53 C52 121.2(2) . . ?
C53 C54 C55 119.4(2) . . ?
C56 C55 C54 120.1(2) . . ?
C55 C56 C51 120.5(2) . . ?

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
S2 O1 C7 C8 19.72(19) . . . . ?
S2 O1 C7 C51 -156.45(14) . . . . ?
S2 N3 C1 C2 81.4(2) . . . . ?
S2 N3 C8 C7 -10.0(2) . . . . ?
S2 N3 C8 C41 168.59(14) . . . . ?
O1 S2 N3 C1 -118.01(16) . . . . ?
O1 S2 N3 C8 19.22(14) . . . . ?
O1 C7 C8 N3 -5.8(2) . . . . ?
O1 C7 C8 C41 175.73(18) . . . . ?
O1 C7 C51 C52 -24.5(2) . . . . ?
O1 C7 C51 C56 153.77(18) . . . . ?
O2 S2 O1 C7 91.22(14) . . . . ?
O2 S2 N3 C1 130.43(16) . . . . ?
O2 S2 N3 C8 -92.34(15) . . . . ?
O3 S2 O1 C7 -138.23(13) . . . . ?
O3 S2 N3 C1 -4.67(19) . . . . ?
O3 S2 N3 C8 132.56(15) . . . . ?
N3 S2 O1 C7 -22.56(13) . . . . ?
N3 C1 C2 C3 112.5(2) . . . . ?
N3 C8 C41 C42 130.3(2) . . . . ?
N3 C8 C41 C46 -48.1(3) . . . . ?
C1 N3 C8 C7 127.13(19) . . . . ?
C1 N3 C8 C41 -54.2(2) . . . . ?
C1 C2 C3 C4 178.4(2) . . . . ?
C2 C3 C4 C5 -114.9(4) . . . . ?
C2 C3 C4 C5A -135.6(5) . . . . ?
C3 C4 C5 C6 -176.1(4) . . . . ?
C3 C4 C5A C6A 67.8(9) . . . . ?
C7 C8 C41 C42 -51.4(3) . . . . ?
C7 C8 C41 C46 130.3(2) . . . . ?
C7 C51 C52 C53 179.3(2) . . . . ?
C7 C51 C56 C55 -179.05(18) . . . . ?
C8 N3 C1 C2 -50.5(2) . . . . ?
C8 C7 C51 C52 160.4(2) . . . . ?
C8 C7 C51 C56 -21.3(3) . . . . ?
C8 C41 C42 C43 -179.81(19) . . . . ?
C8 C41 C46 C45 -179.43(18) . . . . ?
C41 C42 C43 C44 0.0(3) . . . . ?
C42 C41 C46 C45 2.2(3) . . . . ?
C42 C43 C44 C45 0.7(3) . . . . ?
C43 C44 C45 C46 0.1(3) . . . . ?
C44 C45 C46 C41 -1.5(3) . . . . ?
C46 C41 C42 C43 -1.5(3) . . . . ?
C51 C7 C8 N3 169.3(2) . . . . ?
C51 C7 C8 C41 -9.1(4) . . . . ?
C51 C52 C53 C54 -0.2(3) . . . . ?
C52 C51 C56 C55 -0.7(3) . . . . ?
C52 C53 C54 C55 -0.7(4) . . . . ?
C53 C54 C55 C56 0.9(3) . . . . ?
C54 C55 C56 C51 -0.2(3) . . . . ?
C56 C51 C52 C53 0.9(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen mount + N-Paratone'
_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 1.052
_oxdiff_exptl_absorpt_empirical_full_min 0.965
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.80(8)
2 0.20(8)
####################################################################### 
# 
# 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_(SS)-3fa_exp_289_hp
_database_code_depnum_ccdc_archive 'CCDC 2087725'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_audit_creation_date             2021-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            (S,S)-3fa
_chemical_name_systematic        
(E)-5-(1,3-diphenylallyl)-4,5-diphenyl-5H-1,2,3-oxathiazole-2,2-dioxide
_chemical_formula_moiety         'C29 H23 N O3 S, C4 H8 O'
_chemical_formula_sum            'C33 H31 N O4 S'
_chemical_formula_weight         537.65
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C29H23N1O3S1
_chemical_oxdiff_usercomment     'E70_C-allyated Major'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0008(2)
_cell_length_b                   15.0151(3)
_cell_length_c                   10.6877(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.229(2)
_cell_angle_gamma                90
_cell_volume                     1379.60(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16352
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.8380
_cell_measurement_theta_min      1.9990
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
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    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method 'Hexane layered on THF'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44315
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.125
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector HyPix Bantam 3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00   6.78  368
  2  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00  55.34  368
  3  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00 112.35  368
  4  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00 -30.00  368
  5  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00  30.00  368
  6  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00 -38.15  368
  7  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00  90.00  368
  8  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00  44.73  368
  9  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00  60.00  368
 10  ω    -74.00  63.50   0.50    5.00    --   20.00  54.00  60.00  275
 11  ω    -74.00 110.00   0.50    5.00    --   20.00  54.00 120.00  368
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0612034000
_diffrn_orient_matrix_UB_12      0.0295361000
_diffrn_orient_matrix_UB_13      0.0313178000
_diffrn_orient_matrix_UB_21      0.0437155000
_diffrn_orient_matrix_UB_22      -0.0362722000
_diffrn_orient_matrix_UB_23      0.0347741000
_diffrn_orient_matrix_UB_31      0.0338881000
_diffrn_orient_matrix_UB_32      -0.0066214000
_diffrn_orient_matrix_UB_33      -0.0513605000
_diffrn_oxdiff_digest_frames     
;
01a974c3bbd28b299f272504c698ec8537039554902
;
_diffrn_oxdiff_digest_hkl        
;
01f2900eb31deb970f130b5285549ab4700183
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                6459
_reflns_number_total             7355
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.07
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         0.235
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7355
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.059
_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)+(0.0513P)²+0.2076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2T(H2TA,H2TB), C3T(H3TA,H3TB), C4T(H4TA,H4TB), C5T(H5TA,H5TB)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
  C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S2OX S 0.71470(7) 0.38159(4) 0.53075(5) 0.03589(14) Uani 1 1 d . . . . .
O1OX O 0.68767(18) 0.34690(11) 0.38470(14) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.7134(3) 0.30713(15) 0.61273(17) 0.0524(5) Uani 1 1 d . . . . .
O3 O 0.8449(2) 0.43990(15) 0.56608(18) 0.0494(5) Uani 1 1 d . . . . .
N3OX N 0.5537(2) 0.43958(14) 0.50540(19) 0.0336(4) Uani 1 1 d . . . . .
C1 C 0.3320(3) 0.49074(16) 0.3386(2) 0.0314(5) Uani 1 1 d . . . . .
C2 C 0.3088(3) 0.55756(18) 0.4225(3) 0.0407(6) Uani 1 1 d . . . . .
H2 H 0.383632 0.566296 0.505380 0.049 Uiso 1 1 calc R . . . .
C3 C 0.2219(3) 0.4785(2) 0.2175(3) 0.0451(6) Uani 1 1 d . . . . .
H3 H 0.236882 0.433871 0.159461 0.054 Uiso 1 1 calc R . . . .
C4 C 0.1783(3) 0.61057(19) 0.3857(3) 0.0478(7) Uani 1 1 d . . . . .
H4 H 0.163176 0.655693 0.443014 0.057 Uiso 1 1 calc R . . . .
C4OX C 0.4750(3) 0.43811(15) 0.3837(2) 0.0283(4) Uani 1 1 d . . . . .
C5 C 0.0902(4) 0.5317(3) 0.1818(3) 0.0571(8) Uani 1 1 d . . . . .
H5 H 0.013817 0.522581 0.099864 0.069 Uiso 1 1 calc R . . . .
C5OX C 0.5458(2) 0.38281(16) 0.29308(17) 0.0249(4) Uani 1 1 d . . . . .
C6 C 0.0696(3) 0.5980(2) 0.2653(3) 0.0519(7) Uani 1 1 d . . . . .
H6 H -0.019904 0.635048 0.239430 0.062 Uiso 1 1 calc R . . . .
C7 C 0.4447(2) 0.30299(16) 0.2338(2) 0.0293(4) Uani 1 1 d . . . . .
C8 C 0.4157(3) 0.23859(17) 0.3176(3) 0.0377(5) Uani 1 1 d . . . . .
H8 H 0.458439 0.245440 0.409617 0.045 Uiso 1 1 calc R . . . .
C9 C 0.3794(3) 0.29269(19) 0.0989(2) 0.0362(5) Uani 1 1 d . . . . .
H9 H 0.396156 0.336619 0.040528 0.043 Uiso 1 1 calc R . . . .
C10 C 0.3250(3) 0.1645(2) 0.2679(3) 0.0479(7) Uani 1 1 d . . . . .
H10 H 0.305383 0.121216 0.325905 0.057 Uiso 1 1 calc R . . . .
C11 C 0.2896(3) 0.2178(2) 0.0500(3) 0.0462(7) Uani 1 1 d . . . . .
H11 H 0.246103 0.210592 -0.041901 0.055 Uiso 1 1 calc R . . . .
C12 C 0.2632(3) 0.1539(2) 0.1340(3) 0.0503(7) Uani 1 1 d . . . . .
H12 H 0.202716 0.102740 0.099748 0.060 Uiso 1 1 calc R . . . .
C13 C 0.5926(2) 0.44626(15) 0.19629(19) 0.0258(4) Uani 1 1 d . . . . .
H13 H 0.494120 0.468777 0.133242 0.031 Uiso 1 1 calc R . . . .
C14 C 0.6879(3) 0.40351(16) 0.1155(2) 0.0315(5) Uani 1 1 d . . . . .
C15 C 0.8263(4) 0.3593(2) 0.1713(3) 0.0558(8) Uani 1 1 d . . . . .
H15 H 0.864201 0.352946 0.263801 0.067 Uiso 1 1 calc R . . . .
C16 C 0.6410(3) 0.4174(2) -0.0190(2) 0.0503(8) Uani 1 1 d . . . . .
H16 H 0.548494 0.449983 -0.058464 0.060 Uiso 1 1 calc R . . . .
C17 C 0.9111(5) 0.3239(3) 0.0923(4) 0.0733(12) Uani 1 1 d . . . . .
H17 H 1.003511 0.291050 0.130895 0.088 Uiso 1 1 calc R . . . .
C18 C 0.7276(4) 0.3843(3) -0.0962(3) 0.0695(11) Uani 1 1 d . . . . .
H18 H 0.694114 0.394761 -0.187935 0.083 Uiso 1 1 calc R . . . .
C19 C 0.8605(5) 0.3368(2) -0.0419(4) 0.0674(11) Uani 1 1 d . . . . .
H19 H 0.917761 0.312830 -0.095858 0.081 Uiso 1 1 calc R . . . .
C20 C 0.6780(2) 0.52599(15) 0.2696(2) 0.0263(4) Uani 1 1 d . . . . .
H20 H 0.781336 0.517579 0.324678 0.032 Uiso 1 1 calc R . . . .
C21 C 0.6173(3) 0.60718(16) 0.2617(2) 0.0290(4) Uani 1 1 d . . . . .
H21 H 0.515733 0.615070 0.203133 0.035 Uiso 1 1 calc R . . . .
C22 C 0.6926(3) 0.68571(16) 0.3350(2) 0.0292(4) Uani 1 1 d . . . . .
C23 C 0.6311(3) 0.77037(17) 0.2975(3) 0.0414(6) Uani 1 1 d . . . . .
H23 H 0.540249 0.776297 0.224850 0.050 Uiso 1 1 calc R . . . .
C24 C 0.8240(3) 0.67998(18) 0.4432(2) 0.0362(5) Uani 1 1 d . . . . .
H24 H 0.867326 0.623246 0.472304 0.043 Uiso 1 1 calc R . . . .
C25 C 0.7002(4) 0.84561(19) 0.3642(3) 0.0481(7) Uani 1 1 d . . . . .
H25 H 0.656415 0.902529 0.336917 0.058 Uiso 1 1 calc R . . . .
C26 C 0.8925(3) 0.7557(2) 0.5089(3) 0.0455(6) Uani 1 1 d . . . . .
H26 H 0.982787 0.750296 0.582110 0.055 Uiso 1 1 calc R . . . .
C27 C 0.8319(3) 0.83891(19) 0.4698(3) 0.0466(7) Uani 1 1 d . . . . .
H27 H 0.880100 0.890743 0.514951 0.056 Uiso 1 1 calc R . . . .
O1T O 1.2832(3) 0.5111(2) 0.9333(2) 0.0687(7) Uani 1 1 d . . . . .
C2T C 1.3266(4) 0.6008(3) 0.9167(3) 0.0712(11) Uani 1 1 d . . . . .
H2TA H 1.440815 0.608513 0.950188 0.085 Uiso 1 1 calc R . . . .
H2TB H 1.276273 0.642898 0.962854 0.085 Uiso 1 1 calc R . . . .
C3T C 1.2695(4) 0.6153(3) 0.7710(3) 0.0610(9) Uani 1 1 d . . . . .
H3TA H 1.252500 0.679380 0.749500 0.073 Uiso 1 1 calc R . . . .
H3TB H 1.343710 0.591043 0.727403 0.073 Uiso 1 1 calc R . . . .
C4T C 1.1197(4) 0.5650(2) 0.7324(3) 0.0584(8) Uani 1 1 d . . . . .
H4TA H 1.101889 0.537233 0.645121 0.070 Uiso 1 1 calc R . . . .
H4TB H 1.031251 0.604797 0.729807 0.070 Uiso 1 1 calc R . . . .
C5T C 1.1385(4) 0.4938(2) 0.8382(3) 0.0524(7) Uani 1 1 d . . . . .
H5TA H 1.052557 0.497540 0.878165 0.063 Uiso 1 1 calc R . . . .
H5TB H 1.138284 0.433578 0.800430 0.063 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
S2OX O1OX 1.5944(15) . ?
S2OX O2 1.423(2) . ?
S2OX O3 1.421(2) . ?
S2OX N3OX 1.643(2) . ?
O1OX C5OX 1.463(2) . ?
N3OX C4OX 1.283(3) . ?
C1 C2 1.402(3) . ?
C1 C3 1.389(4) . ?
C1 C4OX 1.465(3) . ?
C2 H2 0.9500 . ?
C2 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C3 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C6 1.380(5) . ?
C4OX C5OX 1.549(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(5) . ?
C5OX C7 1.524(3) . ?
C5OX C13 1.553(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(3) . ?
C7 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C8 C10 1.389(4) . ?
C9 H9 0.9500 . ?
C9 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C10 C12 1.383(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(5) . ?
C12 H12 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.527(3) . ?
C13 C20 1.511(3) . ?
C14 C15 1.382(4) . ?
C14 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C17 1.400(4) . ?
C16 H16 0.9500 . ?
C16 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C17 C19 1.384(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.366(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.328(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.466(3) . ?
C22 C23 1.397(3) . ?
C22 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C23 C25 1.382(4) . ?
C24 H24 0.9500 . ?
C24 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C25 C27 1.378(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(4) . ?
C27 H27 0.9500 . ?
O1T C2T 1.429(5) . ?
O1T C5T 1.418(4) . ?
C2T H2TA 0.9900 . ?
C2T H2TB 0.9900 . ?
C2T C3T 1.504(4) . ?
C3T H3TA 0.9900 . ?
C3T H3TB 0.9900 . ?
C3T C4T 1.494(5) . ?
C4T H4TA 0.9900 . ?
C4T H4TB 0.9900 . ?
C4T C5T 1.529(4) . ?
C5T H5TA 0.9900 . ?
C5T H5TB 0.9900 . ?

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
O1OX S2OX N3OX 98.07(9) . . ?
O2 S2OX O1OX 108.64(11) . . ?
O2 S2OX N3OX 110.49(12) . . ?
O3 S2OX O1OX 109.63(11) . . ?
O3 S2OX O2 118.50(13) . . ?
O3 S2OX N3OX 109.58(12) . . ?
C5OX O1OX S2OX 112.63(12) . . ?
C4OX N3OX S2OX 110.67(16) . . ?
C2 C1 C4OX 117.3(2) . . ?
C3 C1 C2 119.3(2) . . ?
C3 C1 C4OX 123.4(2) . . ?
C1 C2 H2 119.8 . . ?
C4 C2 C1 120.5(3) . . ?
C4 C2 H2 119.8 . . ?
C1 C3 H3 120.1 . . ?
C5 C3 C1 119.8(3) . . ?
C5 C3 H3 120.1 . . ?
C2 C4 H4 120.1 . . ?
C2 C4 C6 119.8(3) . . ?
C6 C4 H4 120.1 . . ?
N3OX C4OX C1 119.5(2) . . ?
N3OX C4OX C5OX 115.92(19) . . ?
C1 C4OX C5OX 124.54(19) . . ?
C3 C5 H5 119.9 . . ?
C3 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
O1OX C5OX C4OX 102.61(15) . . ?
O1OX C5OX C7 106.47(18) . . ?
O1OX C5OX C13 108.45(16) . . ?
C4OX C5OX C13 109.32(18) . . ?
C7 C5OX C4OX 112.08(16) . . ?
C7 C5OX C13 116.85(16) . . ?
C4 C6 C5 120.3(3) . . ?
C4 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C5OX 118.8(2) . . ?
C8 C7 C9 119.0(2) . . ?
C9 C7 C5OX 122.2(2) . . ?
C7 C8 H8 119.6 . . ?
C10 C8 C7 120.8(3) . . ?
C10 C8 H8 119.6 . . ?
C7 C9 H9 120.1 . . ?
C11 C9 C7 119.8(3) . . ?
C11 C9 H9 120.1 . . ?
C8 C10 H10 120.1 . . ?
C12 C10 C8 119.9(3) . . ?
C12 C10 H10 120.1 . . ?
C9 C11 H11 119.7 . . ?
C12 C11 C9 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C12 H12 120.0 . . ?
C11 C12 C10 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C5OX C13 H13 107.2 . . ?
C14 C13 C5OX 115.30(18) . . ?
C14 C13 H13 107.2 . . ?
C20 C13 C5OX 109.71(16) . . ?
C20 C13 H13 107.2 . . ?
C20 C13 C14 109.97(17) . . ?
C15 C14 C13 122.9(2) . . ?
C15 C14 C16 118.6(2) . . ?
C16 C14 C13 118.2(2) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C17 120.3(3) . . ?
C17 C15 H15 119.8 . . ?
C14 C16 H16 119.6 . . ?
C18 C16 C14 120.7(3) . . ?
C18 C16 H16 119.6 . . ?
C15 C17 H17 119.9 . . ?
C19 C17 C15 120.1(3) . . ?
C19 C17 H17 119.9 . . ?
C16 C18 H18 119.6 . . ?
C19 C18 C16 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C19 H19 120.3 . . ?
C18 C19 C17 119.3(3) . . ?
C18 C19 H19 120.3 . . ?
C13 C20 H20 118.1 . . ?
C21 C20 C13 123.88(19) . . ?
C21 C20 H20 118.1 . . ?
C20 C21 H21 117.0 . . ?
C20 C21 C22 126.0(2) . . ?
C22 C21 H21 117.0 . . ?
C23 C22 C21 119.8(2) . . ?
C24 C22 C21 122.6(2) . . ?
C24 C22 C23 117.5(2) . . ?
C22 C23 H23 119.5 . . ?
C25 C23 C22 121.1(3) . . ?
C25 C23 H23 119.5 . . ?
C22 C24 H24 119.6 . . ?
C26 C24 C22 120.9(2) . . ?
C26 C24 H24 119.6 . . ?
C23 C25 H25 119.7 . . ?
C27 C25 C23 120.7(3) . . ?
C27 C25 H25 119.7 . . ?
C24 C26 H26 119.5 . . ?
C27 C26 C24 121.0(3) . . ?
C27 C26 H26 119.5 . . ?
C25 C27 H27 120.6 . . ?
C26 C27 C25 118.8(3) . . ?
C26 C27 H27 120.6 . . ?
C5T O1T C2T 108.1(2) . . ?
O1T C2T H2TA 110.9 . . ?
O1T C2T H2TB 110.9 . . ?
O1T C2T C3T 104.1(3) . . ?
H2TA C2T H2TB 109.0 . . ?
C3T C2T H2TA 110.9 . . ?
C3T C2T H2TB 110.9 . . ?
C2T C3T H3TA 111.3 . . ?
C2T C3T H3TB 111.3 . . ?
H3TA C3T H3TB 109.2 . . ?
C4T C3T C2T 102.5(3) . . ?
C4T C3T H3TA 111.3 . . ?
C4T C3T H3TB 111.3 . . ?
C3T C4T H4TA 110.8 . . ?
C3T C4T H4TB 110.8 . . ?
C3T C4T C5T 104.9(2) . . ?
H4TA C4T H4TB 108.8 . . ?
C5T C4T H4TA 110.8 . . ?
C5T C4T H4TB 110.8 . . ?
O1T C5T C4T 106.2(2) . . ?
O1T C5T H5TA 110.5 . . ?
O1T C5T H5TB 110.5 . . ?
C4T C5T H5TA 110.5 . . ?
C4T C5T H5TB 110.5 . . ?
H5TA C5T H5TB 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2OX O1OX C5OX C4OX -3.0(2) . . . . ?
S2OX O1OX C5OX C7 -120.84(15) . . . . ?
S2OX O1OX C5OX C13 112.64(15) . . . . ?
S2OX N3OX C4OX C1 -175.95(17) . . . . ?
S2OX N3OX C4OX C5OX 1.0(3) . . . . ?
O1OX S2OX N3OX C4OX -2.56(19) . . . . ?
O1OX C5OX C7 C8 51.0(2) . . . . ?
O1OX C5OX C7 C9 -129.6(2) . . . . ?
O1OX C5OX C13 C14 59.4(2) . . . . ?
O1OX C5OX C13 C20 -65.4(2) . . . . ?
O2 S2OX O1OX C5OX 118.25(17) . . . . ?
O2 S2OX N3OX C4OX -115.98(19) . . . . ?
O3 S2OX O1OX C5OX -110.84(16) . . . . ?
O3 S2OX N3OX C4OX 111.68(19) . . . . ?
N3OX S2OX O1OX C5OX 3.36(17) . . . . ?
N3OX C4OX C5OX O1OX 1.2(3) . . . . ?
N3OX C4OX C5OX C7 115.0(2) . . . . ?
N3OX C4OX C5OX C13 -113.8(2) . . . . ?
C1 C2 C4 C6 -0.1(4) . . . . ?
C1 C3 C5 C6 1.3(5) . . . . ?
C1 C4OX C5OX O1OX 178.0(2) . . . . ?
C1 C4OX C5OX C7 -68.2(3) . . . . ?
C1 C4OX C5OX C13 63.0(3) . . . . ?
C2 C1 C3 C5 -0.7(4) . . . . ?
C2 C1 C4OX N3OX 16.1(3) . . . . ?
C2 C1 C4OX C5OX -160.6(2) . . . . ?
C2 C4 C6 C5 0.7(5) . . . . ?
C3 C1 C2 C4 0.0(4) . . . . ?
C3 C1 C4OX N3OX -165.1(3) . . . . ?
C3 C1 C4OX C5OX 18.2(4) . . . . ?
C3 C5 C6 C4 -1.3(5) . . . . ?
C4OX C1 C2 C4 179.0(2) . . . . ?
C4OX C1 C3 C5 -179.5(3) . . . . ?
C4OX C5OX C7 C8 -60.5(3) . . . . ?
C4OX C5OX C7 C9 119.0(2) . . . . ?
C4OX C5OX C13 C14 170.52(17) . . . . ?
C4OX C5OX C13 C20 45.7(2) . . . . ?
C5OX C7 C8 C10 -179.7(2) . . . . ?
C5OX C7 C9 C11 179.2(2) . . . . ?
C5OX C13 C14 C15 -55.8(3) . . . . ?
C5OX C13 C14 C16 130.8(2) . . . . ?
C5OX C13 C20 C21 -107.1(2) . . . . ?
C7 C5OX C13 C14 -60.9(2) . . . . ?
C7 C5OX C13 C20 174.32(17) . . . . ?
C7 C8 C10 C12 0.4(4) . . . . ?
C7 C9 C11 C12 0.6(4) . . . . ?
C8 C7 C9 C11 -1.4(3) . . . . ?
C8 C10 C12 C11 -1.2(4) . . . . ?
C9 C7 C8 C10 0.9(4) . . . . ?
C9 C11 C12 C10 0.7(4) . . . . ?
C13 C5OX C7 C8 172.3(2) . . . . ?
C13 C5OX C7 C9 -8.3(3) . . . . ?
C13 C14 C15 C17 -177.9(3) . . . . ?
C13 C14 C16 C18 176.5(3) . . . . ?
C13 C20 C21 C22 177.1(2) . . . . ?
C14 C13 C20 C21 125.1(2) . . . . ?
C14 C15 C17 C19 3.2(6) . . . . ?
C14 C16 C18 C19 0.4(6) . . . . ?
C15 C14 C16 C18 2.8(5) . . . . ?
C15 C17 C19 C18 0.1(6) . . . . ?
C16 C14 C15 C17 -4.5(5) . . . . ?
C16 C18 C19 C17 -1.8(6) . . . . ?
C20 C13 C14 C15 68.8(3) . . . . ?
C20 C13 C14 C16 -104.6(3) . . . . ?
C20 C21 C22 C23 166.2(2) . . . . ?
C20 C21 C22 C24 -14.5(3) . . . . ?
C21 C22 C23 C25 -179.5(2) . . . . ?
C21 C22 C24 C26 179.3(2) . . . . ?
C22 C23 C25 C27 0.0(4) . . . . ?
C22 C24 C26 C27 0.5(4) . . . . ?
C23 C22 C24 C26 -1.3(4) . . . . ?
C23 C25 C27 C26 -0.8(4) . . . . ?
C24 C22 C23 C25 1.1(4) . . . . ?
C24 C26 C27 C25 0.6(4) . . . . ?
O1T C2T C3T C4T 37.3(4) . . . . ?
C2T O1T C5T C4T 18.9(4) . . . . ?
C2T C3T C4T C5T -25.5(4) . . . . ?
C3T C4T C5T O1T 5.1(4) . . . . ?
C5T O1T C2T C3T -35.6(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen mount + N-Paratone'
_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 1.085
_oxdiff_exptl_absorpt_empirical_full_min 0.909

####################################################################### 
# 
# 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_(S)-3ca_exp_292_hp
_database_code_depnum_ccdc_archive 'CCDC 2087724'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_audit_creation_date             2021-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            (S)-3ca
_chemical_name_systematic        
'5-cinnamyl-4,5-diphenyl-5H-1,2,3-oxathiazole 2,2-dioxide'
_chemical_formula_moiety         'C23 H19 N O3 S'
_chemical_formula_sum            'C23 H19 N O3 S'
_chemical_formula_weight         389.45
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H19N1O3S1
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2466(2)
_cell_length_b                   10.2138(3)
_cell_length_c                   10.4986(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.584(2)
_cell_angle_gamma                90
_cell_volume                     988.34(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9185
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.6110
_cell_measurement_theta_min      1.9540
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
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    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             408
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'layering hexane on THF'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17523
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.946
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 
'Hybrid Pixel Array Detector HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50   20.00    --   20.00  54.00 168.21  368
  2  ω    -74.00 110.00   0.50   20.00    --   20.00  54.00   9.44  368
  3  ω    -74.00 110.00   0.50   20.00    --   20.00  54.00  90.00  368
  4  ω    -74.00  86.00   0.50   20.00    --   20.00  54.00-127.89  320
  5  ω    -74.00 110.00   0.50   20.00    --   20.00  54.00-127.89  368
  6  ω    -74.00 108.00   0.50   20.00    --   20.00  54.00 -30.00  364
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0549458000
_diffrn_orient_matrix_UB_12      0.0485571000
_diffrn_orient_matrix_UB_13      0.0067127000
_diffrn_orient_matrix_UB_21      0.0015187000
_diffrn_orient_matrix_UB_22      0.0026869000
_diffrn_orient_matrix_UB_23      -0.0673976000
_diffrn_orient_matrix_UB_31      -0.0538236000
_diffrn_orient_matrix_UB_32      0.0495930000
_diffrn_orient_matrix_UB_33      -0.0028590000
_diffrn_oxdiff_digest_frames     
;
01bb4ac95d2a2df35ed62f01369abf452102156f2f6
;
_diffrn_oxdiff_digest_hkl        
;
014bc068f551f9fda6fc966c72155973ee9d7c
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4367
_reflns_number_total             4872
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         0.480
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4872
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.043
_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)+(0.0610P)²+0.1015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1011
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_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
C1 C 0.2281(3) 0.5912(3) 0.3288(2) 0.0313(5) Uani 1 1 d . . . . .
C2 C 0.0970(3) 0.6246(3) 0.3788(3) 0.0381(6) Uani 1 1 d . . . . .
H2 H 0.040614 0.558690 0.415056 0.046 Uiso 1 1 calc R . . . .
C3 C 0.0493(3) 0.7529(3) 0.3757(3) 0.0448(7) Uani 1 1 d . . . . .
H3 H -0.038708 0.775267 0.411249 0.054 Uiso 1 1 calc R . . . .
C4 C 0.1296(3) 0.8483(3) 0.3209(3) 0.0410(6) Uani 1 1 d . . . . .
H4 H 0.094888 0.935859 0.316749 0.049 Uiso 1 1 calc R . . . .
C5 C 0.2591(3) 0.8183(3) 0.2721(3) 0.0411(6) Uani 1 1 d . . . . .
H5 H 0.313867 0.885038 0.235163 0.049 Uiso 1 1 calc R . . . .
C6 C 0.3100(3) 0.6893(3) 0.2769(3) 0.0386(6) Uani 1 1 d . . . . .
H6 H 0.400401 0.668630 0.244833 0.046 Uiso 1 1 calc R . . . .
C7 C 0.5273(3) 0.4384(3) 0.2544(2) 0.0359(6) Uani 1 1 d . . . . .
C8 C 0.4778(3) 0.4092(5) 0.1298(3) 0.0584(9) Uani 1 1 d . . . . .
H8 H 0.383570 0.373221 0.112117 0.070 Uiso 1 1 calc R . . . .
C9 C 0.5646(3) 0.4322(5) 0.0308(3) 0.0686(12) Uani 1 1 d . . . . .
H9 H 0.528991 0.413030 -0.054559 0.082 Uiso 1 1 calc R . . . .
C10 C 0.7023(3) 0.4825(4) 0.0548(3) 0.0545(8) Uani 1 1 d . . . . .
H10 H 0.762145 0.497165 -0.013256 0.065 Uiso 1 1 calc R . . . .
C11 C 0.7515(3) 0.5111(4) 0.1779(3) 0.0546(9) Uani 1 1 d . . . . .
H11 H 0.846176 0.546277 0.195079 0.065 Uiso 1 1 calc R . . . .
C12 C 0.6649(3) 0.4895(4) 0.2786(3) 0.0476(7) Uani 1 1 d . . . . .
H12 H 0.700428 0.509915 0.363694 0.057 Uiso 1 1 calc R . . . .
C13 C 0.4878(3) 0.4596(3) 0.4934(2) 0.0348(5) Uani 1 1 d . . . . .
H13A H 0.585206 0.421708 0.514769 0.042 Uiso 1 1 calc R . . . .
H13B H 0.498956 0.555873 0.488818 0.042 Uiso 1 1 calc R . . . .
C14 C 0.3935(3) 0.4278(3) 0.5987(2) 0.0363(5) Uani 1 1 d . . . . .
H14 H 0.372022 0.338555 0.614339 0.044 Uiso 1 1 calc R . . . .
C15 C 0.3388(3) 0.5184(3) 0.6710(3) 0.0381(6) Uani 1 1 d . . . . .
H15 H 0.355858 0.606832 0.648686 0.046 Uiso 1 1 calc R . . . .
C16 C 0.2542(3) 0.4972(3) 0.7824(2) 0.0408(6) Uani 1 1 d . . . . .
C17 C 0.2006(4) 0.6050(5) 0.8441(3) 0.0678(11) Uani 1 1 d . . . . .
H17 H 0.216157 0.690870 0.813138 0.081 Uiso 1 1 calc R . . . .
C18 C 0.1231(5) 0.5862(6) 0.9528(4) 0.0891(16) Uani 1 1 d . . . . .
H18 H 0.086648 0.659913 0.995185 0.107 Uiso 1 1 calc R . . . .
C19 C 0.0999(4) 0.4647(6) 0.9975(3) 0.0783(16) Uani 1 1 d . . . . .
H19 H 0.046089 0.453680 1.070125 0.094 Uiso 1 1 calc R . . . .
C20 C 0.1536(3) 0.3563(5) 0.9386(3) 0.0659(11) Uani 1 1 d . . . . .
H20 H 0.138067 0.271171 0.971261 0.079 Uiso 1 1 calc R . . . .
C21 C 0.2302(3) 0.3721(4) 0.8320(3) 0.0525(9) Uani 1 1 d . . . . .
H21 H 0.267019 0.297333 0.791572 0.063 Uiso 1 1 calc R . . . .
S2OX S 0.25466(7) 0.21742(6) 0.33922(6) 0.03559(16) Uani 1 1 d . . . . .
O1OX O 0.41710(19) 0.2659(2) 0.37105(18) 0.0376(4) Uani 1 1 d . . . . .
O2OX O 0.2434(2) 0.1500(2) 0.2214(2) 0.0487(5) Uani 1 1 d . . . . .
O3OX O 0.2087(2) 0.15243(19) 0.44854(19) 0.0426(5) Uani 1 1 d . . . . .
N3OX N 0.1760(2) 0.3627(2) 0.3225(2) 0.0339(5) Uani 1 1 d . . . . .
C4OX C 0.2717(2) 0.4530(3) 0.3332(2) 0.0302(5) Uani 1 1 d . . . . .
C5OX C 0.4296(3) 0.4092(3) 0.3615(2) 0.0326(5) 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
C1 C2 1.401(3) . ?
C1 C6 1.392(3) . ?
C1 C4OX 1.467(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(4) . ?
C7 C12 1.380(4) . ?
C7 C5OX 1.527(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.367(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.498(3) . ?
C13 C5OX 1.534(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.322(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.474(3) . ?
C16 C17 1.389(5) . ?
C16 C21 1.403(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.409(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.350(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(4) . ?
C21 H21 0.9500 . ?
S2OX O1OX 1.5914(19) . ?
S2OX O2OX 1.413(2) . ?
S2OX O3OX 1.4202(19) . ?
S2OX N3OX 1.655(2) . ?
O1OX C5OX 1.472(3) . ?
N3OX C4OX 1.277(3) . ?
C4OX C5OX 1.533(3) . ?

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 C1 C4OX 117.8(2) . . ?
C6 C1 C2 119.0(2) . . ?
C6 C1 C4OX 123.2(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C5OX 118.9(2) . . ?
C12 C7 C8 119.1(2) . . ?
C12 C7 C5OX 121.9(2) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 119.8(3) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C14 C13 C5OX 114.3(2) . . ?
C5OX C13 H13A 108.7 . . ?
C5OX C13 H13B 108.7 . . ?
C13 C14 H14 118.5 . . ?
C15 C14 C13 123.0(3) . . ?
C15 C14 H14 118.5 . . ?
C14 C15 H15 116.4 . . ?
C14 C15 C16 127.2(3) . . ?
C16 C15 H15 116.4 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 C21 118.4(3) . . ?
C21 C16 C15 122.5(3) . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.5(4) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.7(4) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.9(4) . . ?
C20 C21 H21 119.6 . . ?
O1OX S2OX N3OX 98.20(11) . . ?
O2OX S2OX O1OX 109.72(12) . . ?
O2OX S2OX O3OX 118.32(13) . . ?
O2OX S2OX N3OX 110.05(12) . . ?
O3OX S2OX O1OX 108.32(11) . . ?
O3OX S2OX N3OX 110.33(11) . . ?
C5OX O1OX S2OX 111.88(16) . . ?
C4OX N3OX S2OX 110.08(17) . . ?
C1 C4OX C5OX 122.8(2) . . ?
N3OX C4OX C1 120.4(2) . . ?
N3OX C4OX C5OX 116.6(2) . . ?
C7 C5OX C13 114.4(2) . . ?
C7 C5OX C4OX 114.3(2) . . ?
O1OX C5OX C7 107.4(2) . . ?
O1OX C5OX C13 107.2(2) . . ?
O1OX C5OX C4OX 103.0(2) . . ?
C4OX C5OX C13 109.64(19) . . ?

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
C1 C2 C3 C4 1.3(5) . . . . ?
C1 C4OX C5OX C7 -70.4(3) . . . . ?
C1 C4OX C5OX C13 59.5(3) . . . . ?
C1 C4OX C5OX O1OX 173.4(2) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
C2 C1 C4OX N3OX 33.0(3) . . . . ?
C2 C1 C4OX C5OX -141.9(2) . . . . ?
C2 C3 C4 C5 -1.8(5) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C6 C1 C4OX N3OX -146.6(2) . . . . ?
C6 C1 C4OX C5OX 38.5(3) . . . . ?
C7 C8 C9 C10 0.9(7) . . . . ?
C8 C7 C12 C11 0.1(5) . . . . ?
C8 C7 C5OX C13 -173.3(3) . . . . ?
C8 C7 C5OX O1OX 67.8(3) . . . . ?
C8 C7 C5OX C4OX -45.8(4) . . . . ?
C8 C9 C10 C11 -0.8(7) . . . . ?
C9 C10 C11 C12 0.3(7) . . . . ?
C10 C11 C12 C7 0.1(6) . . . . ?
C12 C7 C8 C9 -0.6(6) . . . . ?
C12 C7 C5OX C13 8.5(4) . . . . ?
C12 C7 C5OX O1OX -110.4(3) . . . . ?
C12 C7 C5OX C4OX 136.1(3) . . . . ?
C13 C14 C15 C16 -175.2(2) . . . . ?
C14 C13 C5OX C7 -178.5(2) . . . . ?
C14 C13 C5OX O1OX -59.5(3) . . . . ?
C14 C13 C5OX C4OX 51.6(3) . . . . ?
C14 C15 C16 C17 -177.6(3) . . . . ?
C14 C15 C16 C21 4.9(4) . . . . ?
C15 C16 C17 C18 -178.3(3) . . . . ?
C15 C16 C21 C20 178.3(3) . . . . ?
C16 C17 C18 C19 -0.2(6) . . . . ?
C17 C16 C21 C20 0.7(5) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C18 C19 C20 C21 -0.9(5) . . . . ?
C19 C20 C21 C16 0.0(5) . . . . ?
C21 C16 C17 C18 -0.6(5) . . . . ?
S2OX O1OX C5OX C7 -116.76(17) . . . . ?
S2OX O1OX C5OX C13 119.81(17) . . . . ?
S2OX O1OX C5OX C4OX 4.2(2) . . . . ?
S2OX N3OX C4OX C1 -176.70(17) . . . . ?
S2OX N3OX C4OX C5OX -1.5(2) . . . . ?
O1OX S2OX N3OX C4OX 3.72(18) . . . . ?
O2OX S2OX O1OX C5OX 110.05(18) . . . . ?
O2OX S2OX N3OX C4OX -110.84(18) . . . . ?
O3OX S2OX O1OX C5OX -119.44(17) . . . . ?
O3OX S2OX N3OX C4OX 116.80(18) . . . . ?
N3OX S2OX O1OX C5OX -4.76(17) . . . . ?
N3OX C4OX C5OX C7 114.5(3) . . . . ?
N3OX C4OX C5OX C13 -115.5(2) . . . . ?
N3OX C4OX C5OX O1OX -1.6(3) . . . . ?
C4OX C1 C2 C3 -179.1(3) . . . . ?
C4OX C1 C6 C5 177.8(2) . . . . ?
C5OX C7 C8 C9 -178.8(4) . . . . ?
C5OX C7 C12 C11 178.2(3) . . . . ?
C5OX C13 C14 C15 -122.1(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen mount + N-Paratone'
_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 1.118
_oxdiff_exptl_absorpt_empirical_full_min 0.910
####################################################################### 
# 
# 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_3aa_exp_291
_database_code_depnum_ccdc_archive 'CCDC 2087723'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-08-17 downloaded from the CCDC.
;
_audit_creation_date             2021-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            3aa
_chemical_name_systematic        
(E)-5-(hex-2-en-1-yl)-4,5-diphenyl-5H-1,2,3-oxathiazole-2,2-dioxide
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H21N1O3S1
_chemical_oxdiff_usercomment     E39_C-allylated
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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.0914(4)
_cell_length_b                   10.2497(4)
_cell_length_c                   18.7657(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1941.01(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6046
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      20.2850
_cell_measurement_theta_min      2.1510
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
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    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method 'layering hexane on THF'
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            32513
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_min         2.171
_diffrn_ambient_temperature      293.0(10)
_diffrn_detector                 'HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50   20.00    --   20.00  54.00-150.00  368
  2  ω    -74.00 110.00   0.50   20.00    --   20.00  54.00 120.00  368
  3  ω    -74.00 110.00   0.50   20.00    --   20.00  54.00 120.00  368
  4  ω    -74.00 110.00   0.50   20.00    --   20.00  54.00 -60.00  368
  5  ω    -40.00  71.00   0.50   20.00    --   20.00  54.00-180.00  222
  6  ω    -74.00  57.00   0.50   20.00    --   20.00  54.00  30.00  262
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0506525000
_diffrn_orient_matrix_UB_12      0.0449062000
_diffrn_orient_matrix_UB_13      -0.0091944000
_diffrn_orient_matrix_UB_21      -0.0305448000
_diffrn_orient_matrix_UB_22      0.0482571000
_diffrn_orient_matrix_UB_23      0.0215842000
_diffrn_orient_matrix_UB_31      0.0379270000
_diffrn_orient_matrix_UB_32      -0.0211771000
_diffrn_orient_matrix_UB_33      0.0296269000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2990
_reflns_number_total             5428
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_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 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_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         0.221
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 960 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5428
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.015
_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)+(0.0790P)²+0.0970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1548
_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. Restrained distances
 C18-C16
 2.5 with sigma of 0.01
 C16-C15 \\sim C17-C16 \\sim C18-C17
 with sigma of 0.005
3. Rigid bond restraints
 C16, C17, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B)
4.b Me refined with riding coordinates:
 C18(H18A,H18B,H18C)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15)
;
_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
C1 C 0.3481(3) 0.6575(4) 0.48661(16) 0.0595(8) Uani 1 1 d . . . . .
C2 C 0.3057(4) 0.5577(4) 0.53271(18) 0.0754(10) Uani 1 1 d . . . . .
H2 H 0.264333 0.483925 0.514371 0.090 Uiso 1 1 calc R . . . .
C3 C 0.3254(4) 0.5694(5) 0.6051(2) 0.0872(13) Uani 1 1 d . . . . .
H3 H 0.299612 0.502432 0.635550 0.105 Uiso 1 1 calc R . . . .
C4 C 0.3824(4) 0.6786(6) 0.6320(2) 0.0890(14) Uani 1 1 d . . . . .
H4 H 0.393759 0.686267 0.681027 0.107 Uiso 1 1 calc R . . . .
C5 C 0.4240(4) 0.7783(5) 0.5881(2) 0.0835(12) Uani 1 1 d . . . . .
H5 H 0.462735 0.852640 0.607522 0.100 Uiso 1 1 calc R . . . .
C6 C 0.4078(4) 0.7674(4) 0.51466(19) 0.0719(10) Uani 1 1 d . . . . .
H6 H 0.436946 0.833722 0.484673 0.086 Uiso 1 1 calc R . . . .
C7 C 0.3613(3) 0.8560(4) 0.34957(18) 0.0662(9) Uani 1 1 d . . . . .
C8 C 0.2302(4) 0.8873(5) 0.3461(3) 0.1101(17) Uani 1 1 d . . . . .
H8 H 0.167659 0.820658 0.346332 0.132 Uiso 1 1 calc R . . . .
C9 C 0.1880(6) 1.0142(5) 0.3423(4) 0.140(2) Uani 1 1 d . . . . .
H9 H 0.097857 1.031835 0.338772 0.168 Uiso 1 1 calc R . . . .
C10 C 0.2758(5) 1.1145(5) 0.3437(3) 0.1103(16) Uani 1 1 d . . . . .
H10 H 0.246903 1.200616 0.343313 0.132 Uiso 1 1 calc R . . . .
C11 C 0.4070(5) 1.0853(5) 0.3455(3) 0.0975(14) Uani 1 1 d . . . . .
H11 H 0.468950 1.152444 0.344867 0.117 Uiso 1 1 calc R . . . .
C12 C 0.4496(4) 0.9585(4) 0.3484(2) 0.0835(11) Uani 1 1 d . . . . .
H12 H 0.540046 0.941242 0.349656 0.100 Uiso 1 1 calc R . . . .
C13 C 0.5515(3) 0.6872(4) 0.3567(2) 0.0730(10) Uani 1 1 d . . . . .
H13A H 0.594126 0.724402 0.315084 0.088 Uiso 1 1 calc R . . . .
H13B H 0.586783 0.731453 0.398317 0.088 Uiso 1 1 calc R . . . .
C14 C 0.5869(4) 0.5470(5) 0.3612(3) 0.0860(11) Uani 1 1 d . . . . .
H14 H 0.564631 0.494677 0.322505 0.103 Uiso 1 1 calc R . . . .
C15 C 0.6456(5) 0.4916(5) 0.4138(3) 0.1082(17) Uani 1 1 d D . . . .
H15 H 0.664084 0.544323 0.452908 0.130 Uiso 1 1 calc R . . . .
C16 C 0.6881(6) 0.3505(6) 0.4196(5) 0.177(3) Uani 1 1 d D U . . .
H16A H 0.665581 0.305596 0.375758 0.213 Uiso 1 1 calc R . . . .
H16B H 0.639554 0.309294 0.458094 0.213 Uiso 1 1 calc R . . . .
C17 C 0.8357(8) 0.3359(8) 0.4333(6) 0.197(4) Uani 1 1 d D U . . .
H17A H 0.865800 0.402149 0.466440 0.237 Uiso 1 1 calc R . . . .
H17B H 0.854433 0.250758 0.453499 0.237 Uiso 1 1 calc R . . . .
C18 C 0.9045(9) 0.3510(11) 0.3631(6) 0.235(5) Uani 1 1 d D U . . .
H18A H 0.998399 0.342218 0.369824 0.352 Uiso 1 1 calc R . . . .
H18B H 0.873977 0.284832 0.330841 0.352 Uiso 1 1 calc R . . . .
H18C H 0.885293 0.435540 0.343724 0.352 Uiso 1 1 calc R . . . .
O1OX O 0.3554(2) 0.6529(2) 0.28620(11) 0.0687(7) Uani 1 1 d . . . . .
O2OX O 0.1242(3) 0.5839(3) 0.27306(14) 0.0895(9) Uani 1 1 d . . . . .
S2OX S 0.24931(10) 0.54253(10) 0.30026(4) 0.0702(3) Uani 1 1 d . . . . .
N3OX N 0.2479(3) 0.5488(3) 0.38785(13) 0.0649(7) Uani 1 1 d . . . . .
O3OX O 0.3005(3) 0.4216(3) 0.27675(15) 0.0916(9) Uani 1 1 d . . . . .
C4OX C 0.3275(3) 0.6366(3) 0.40995(16) 0.0572(8) Uani 1 1 d . . . . .
C5OX C 0.4026(3) 0.7142(3) 0.35226(17) 0.0595(8) 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
C1 C2 1.406(5) . ?
C1 C6 1.382(5) . ?
C1 C4OX 1.469(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.363(6) . ?
C7 C12 1.377(5) . ?
C7 C5OX 1.513(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.370(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.357(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.358(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(6) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.483(6) . ?
C13 C5OX 1.530(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.284(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.512(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.518(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.496(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O1OX S2OX 1.579(2) . ?
O1OX C5OX 1.469(4) . ?
O2OX S2OX 1.427(3) . ?
S2OX N3OX 1.645(3) . ?
S2OX O3OX 1.414(3) . ?
N3OX C4OX 1.276(4) . ?
C4OX C5OX 1.543(4) . ?

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 C1 C4OX 117.0(3) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 C4OX 123.6(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(4) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.6(4) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C12 116.6(4) . . ?
C8 C7 C5OX 119.6(3) . . ?
C12 C7 C5OX 123.7(3) . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.8(4) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(5) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 121.0 . . ?
C9 C10 C11 118.0(5) . . ?
C11 C10 H10 121.0 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.1(4) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.4(4) . . ?
C11 C12 H12 119.3 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C14 C13 C5OX 114.5(3) . . ?
C5OX C13 H13A 108.6 . . ?
C5OX C13 H13B 108.6 . . ?
C13 C14 H14 117.2 . . ?
C15 C14 C13 125.6(4) . . ?
C15 C14 H14 117.2 . . ?
C14 C15 H15 116.2 . . ?
C14 C15 C16 127.5(6) . . ?
C16 C15 H15 116.2 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C15 C16 C17 112.7(6) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 110.3 . . ?
C16 C17 H17B 110.3 . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 C16 107.2(8) . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5OX O1OX S2OX 112.68(18) . . ?
O1OX S2OX N3OX 98.32(13) . . ?
O2OX S2OX O1OX 109.13(16) . . ?
O2OX S2OX N3OX 109.78(17) . . ?
O3OX S2OX O1OX 109.16(16) . . ?
O3OX S2OX O2OX 118.19(18) . . ?
O3OX S2OX N3OX 110.42(17) . . ?
C4OX N3OX S2OX 110.3(2) . . ?
C1 C4OX C5OX 122.9(3) . . ?
N3OX C4OX C1 120.7(3) . . ?
N3OX C4OX C5OX 116.4(3) . . ?
C7 C5OX C13 116.5(3) . . ?
C7 C5OX C4OX 112.5(3) . . ?
C13 C5OX C4OX 110.5(3) . . ?
O1OX C5OX C7 107.1(3) . . ?
O1OX C5OX C13 106.7(3) . . ?
O1OX C5OX C4OX 102.2(2) . . ?

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
C1 C2 C3 C4 1.8(6) . . . . ?
C1 C4OX C5OX C7 -69.1(4) . . . . ?
C1 C4OX C5OX C13 63.0(4) . . . . ?
C1 C4OX C5OX O1OX 176.3(3) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C2 C1 C4OX N3OX 16.2(5) . . . . ?
C2 C1 C4OX C5OX -161.6(3) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C6 C1 C2 C3 -0.8(5) . . . . ?
C6 C1 C4OX N3OX -164.8(3) . . . . ?
C6 C1 C4OX C5OX 17.4(5) . . . . ?
C7 C8 C9 C10 -1.7(11) . . . . ?
C8 C7 C12 C11 1.4(6) . . . . ?
C8 C7 C5OX C13 -179.5(4) . . . . ?
C8 C7 C5OX O1OX 61.2(5) . . . . ?
C8 C7 C5OX C4OX -50.3(5) . . . . ?
C8 C9 C10 C11 3.0(10) . . . . ?
C9 C10 C11 C12 -2.2(9) . . . . ?
C10 C11 C12 C7 0.0(8) . . . . ?
C12 C7 C8 C9 -0.6(9) . . . . ?
C12 C7 C5OX C13 2.4(5) . . . . ?
C12 C7 C5OX O1OX -116.9(4) . . . . ?
C12 C7 C5OX C4OX 131.5(4) . . . . ?
C13 C14 C15 C16 -177.5(5) . . . . ?
C14 C13 C5OX C7 178.5(3) . . . . ?
C14 C13 C5OX O1OX -62.1(4) . . . . ?
C14 C13 C5OX C4OX 48.4(4) . . . . ?
C14 C15 C16 C17 122.3(8) . . . . ?
C15 C16 C17 C18 -80.6(10) . . . . ?
O1OX S2OX N3OX C4OX 0.8(3) . . . . ?
O2OX S2OX N3OX C4OX -113.1(3) . . . . ?
S2OX O1OX C5OX C7 -116.5(2) . . . . ?
S2OX O1OX C5OX C13 118.1(3) . . . . ?
S2OX O1OX C5OX C4OX 2.0(3) . . . . ?
S2OX N3OX C4OX C1 -177.5(3) . . . . ?
S2OX N3OX C4OX C5OX 0.4(4) . . . . ?
N3OX C4OX C5OX C7 113.0(3) . . . . ?
N3OX C4OX C5OX C13 -114.8(3) . . . . ?
N3OX C4OX C5OX O1OX -1.5(4) . . . . ?
O3OX S2OX N3OX C4OX 114.9(3) . . . . ?
C4OX C1 C2 C3 178.2(3) . . . . ?
C4OX C1 C6 C5 -179.5(3) . . . . ?
C5OX C7 C8 C9 -178.8(5) . . . . ?
C5OX C7 C12 C11 179.6(4) . . . . ?
C5OX C13 C14 C15 -116.8(5) . . . . ?
C5OX O1OX S2OX O2OX 112.6(2) . . . . ?
C5OX O1OX S2OX N3OX -1.7(2) . . . . ?
C5OX O1OX S2OX O3OX -116.8(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen mount + Paratone'
_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 1.120
_oxdiff_exptl_absorpt_empirical_full_min 0.915
