# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_odjp5
_database_code_depnum_ccdc_archive 'CCDC 1570504'
_audit_update_record             
;
2017-08-24 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;
_audit_creation_date             2017-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        '2-Allyl-3-(allylsulfinyl)-1H-indole '
_chemical_formula_moiety         '2(C14 H15 N O S)'
_chemical_formula_sum            'C28 H30 N2 O2 S2'
_chemical_formula_weight         490.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15NOS
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.7719(16)
_cell_length_b                   8.1203(7)
_cell_length_c                   19.0328(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.633(11)
_cell_angle_gamma                90
_cell_volume                     2570.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3373
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.0250
_cell_measurement_theta_min      3.5250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear grayish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   grayish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.0930
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.325
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  76.00   1.00   40.00    --   11.54  77.00 -30.00   52
  2  ω    -66.00 -32.00   1.00   40.00    --   11.54 178.00-150.00   34
  3  ω    -76.00  34.00   1.00   40.00    --  -12.00 -19.00  60.00  110
  4  ω   -101.00 -54.00   1.00   40.00    --  -12.00-178.00 -30.00   47
  5  ω    -41.00  77.00   1.00   40.00    --  -12.00   0.00-150.00  118
  6  ω    -87.00 -57.00   1.00   40.00    --  -12.00-178.00-120.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0126996000
_diffrn_orient_matrix_UB_12      -0.0817549000
_diffrn_orient_matrix_UB_13      -0.0028362000
_diffrn_orient_matrix_UB_21      -0.0319146000
_diffrn_orient_matrix_UB_22      -0.0093171000
_diffrn_orient_matrix_UB_23      -0.0348938000
_diffrn_orient_matrix_UB_31      0.0252814000
_diffrn_orient_matrix_UB_32      0.0293340000
_diffrn_orient_matrix_UB_33      -0.0189619000
_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              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3004
_reflns_number_total             4690
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4690
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.029
_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)+(0.0259P)²+0.4696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.1068
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C27-H00X \\sim C28-HA \\sim C28-H00Z \\sim C24-H00V \\sim C25-H \\sim C25-H00Y
\\sim C14-H00M \\sim C14-
 H00J \\sim C13-H00N \\sim C11-H00F \\sim C11-H00H \\sim C10-H00G
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H00B,H00C), C12(H00D,H00E), C23(H00P,H00Q), C26(H00S,H00T)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H005), N2(H006), C5(H00A), C10(H00G), C4(H00I), C2(H00K), C3(H00L),
 C19(H00O), C13(H00N), C16(H00R), C17(H00U), C24(H00V), C18(H00W), C27(H00X)
3.c X=CH2 refined with riding coordinates:
 C11(H00F,H00H), C14(H00J,H00M), C25(H00Y,H), C28(H00Z,HA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.62853(4) 0.64352(9) 0.68973(4) 0.0240(2) Uani 1 1 d . . . . .
S002 S 0.85935(4) 0.69795(10) 0.61262(4) 0.0289(2) Uani 1 1 d . . . . .
O003 O 0.61643(11) 0.8148(2) 0.65603(11) 0.0304(5) Uani 1 1 d . . . . .
O004 O 0.81997(11) 0.5465(3) 0.63051(11) 0.0366(6) Uani 1 1 d . . . . .
N005 N 0.46724(13) 0.5012(3) 0.77182(12) 0.0223(6) Uani 1 1 d . . . . .
H005 H 0.4536 0.4704 0.8089 0.027 Uiso 1 1 calc R . . . .
N006 N 1.04613(13) 0.8547(3) 0.77915(13) 0.0273(6) Uani 1 1 d . . . . .
H006 H 1.0955 0.8855 0.7979 0.033 Uiso 1 1 calc R . . . .
C007 C 0.45964(16) 0.5753(3) 0.65526(16) 0.0196(7) Uani 1 1 d . . . . .
C008 C 0.54363(16) 0.5380(3) 0.77648(15) 0.0198(7) Uani 1 1 d . . . . .
C009 C 0.41479(16) 0.5207(3) 0.69895(16) 0.0210(7) Uani 1 1 d . . . . .
C00A C 0.41873(16) 0.6081(4) 0.57934(16) 0.0244(7) Uani 1 1 d . . . . .
H00A H 0.4464 0.6452 0.5491 0.029 Uiso 1 1 calc R . . . .
C00B C 0.54175(15) 0.5837(3) 0.70600(15) 0.0197(7) Uani 1 1 d . . . . .
C00C C 0.61166(16) 0.5270(4) 0.84967(15) 0.0256(7) Uani 1 1 d . . . . .
H00B H 0.6602 0.5677 0.8434 0.031 Uiso 1 1 calc R . . . .
H00C H 0.6204 0.4124 0.8649 0.031 Uiso 1 1 calc R . . . .
C00D C 0.99465(17) 0.8378(4) 0.81877(16) 0.0258(7) Uani 1 1 d . . . . .
C00E C 0.91956(17) 0.7840(4) 0.76844(16) 0.0253(7) Uani 1 1 d . . . . .
C00F C 1.00650(16) 0.8147(4) 0.70562(16) 0.0242(7) Uani 1 1 d . . . . .
C00G C 0.59616(16) 0.6239(4) 0.91022(15) 0.0247(7) Uani 1 1 d D . . . .
H00G H 0.5930 0.7378 0.9050 0.030 Uiso 1 1 calc DR . . . .
C00H C 0.92914(16) 0.7699(4) 0.69655(16) 0.0254(7) Uani 1 1 d . . . . .
C00I C 0.33665(17) 0.5847(4) 0.54979(16) 0.0285(7) Uani 1 1 d . . . . .
H00I H 0.3092 0.6065 0.4992 0.034 Uiso 1 1 calc R . . . .
C00J C 0.62300(17) 0.5112(4) 0.61139(16) 0.0262(7) Uani 1 1 d . . . . .
H00D H 0.5776 0.5449 0.5679 0.031 Uiso 1 1 calc R . . . .
H00E H 0.6713 0.5260 0.5995 0.031 Uiso 1 1 calc R . . . .
C00K C 0.33200(17) 0.4966(4) 0.66912(17) 0.0275(8) Uani 1 1 d . . . . .
H00K H 0.3036 0.4599 0.6989 0.033 Uiso 1 1 calc R . . . .
C00L C 0.29388(18) 0.5289(4) 0.59431(17) 0.0297(8) Uani 1 1 d . . . . .
H00L H 0.2386 0.5134 0.5727 0.036 Uiso 1 1 calc R . . . .
C00M C 0.85712(18) 0.7561(4) 0.79560(18) 0.0327(8) Uani 1 1 d . . . . .
H00O H 0.8072 0.7202 0.7635 0.039 Uiso 1 1 calc R . . . .
C00N C 0.61423(19) 0.3333(4) 0.62616(17) 0.0343(8) Uani 1 1 d D . . . .
H00N H 0.5645 0.2973 0.6259 0.041 Uiso 1 1 calc DR . . . .
C00O C 1.04706(17) 0.8283(4) 0.64912(17) 0.0331(8) Uani 1 1 d . . . . .
H00P H 1.0132 0.7773 0.6026 0.040 Uiso 1 1 calc R . . . .
H00Q H 1.0525 0.9438 0.6389 0.040 Uiso 1 1 calc R . . . .
C00P C 1.00840(18) 0.8644(4) 0.89456(17) 0.0327(8) Uani 1 1 d . . . . .
H00R H 1.0582 0.8995 0.9273 0.039 Uiso 1 1 calc R . . . .
C00Q C 0.58678(17) 0.5607(4) 0.96964(17) 0.0365(8) Uani 1 1 d D . . . .
H00F H 0.5896 0.4473 0.9768 0.044 Uiso 1 1 calc DR . . . .
H00H H 0.5773 0.6291 1.0048 0.044 Uiso 1 1 calc DR . . . .
C00R C 0.78542(17) 0.8611(4) 0.59390(18) 0.0360(8) Uani 1 1 d . . . . .
H00S H 0.7394 0.8342 0.5497 0.043 Uiso 1 1 calc R . . . .
H00T H 0.7671 0.8724 0.6360 0.043 Uiso 1 1 calc R . . . .
C00S C 0.9454(2) 0.8365(4) 0.91889(18) 0.0376(9) Uani 1 1 d . . . . .
H00U H 0.9528 0.8542 0.9692 0.045 Uiso 1 1 calc R . . . .
C00T C 1.12823(18) 0.7495(4) 0.67361(17) 0.0346(8) Uani 1 1 d D . . . .
H00V H 1.1317 0.6382 0.6859 0.042 Uiso 1 1 calc DR . . . .
C00U C 0.8705(2) 0.7825(4) 0.87045(19) 0.0387(9) Uani 1 1 d . . . . .
H00W H 0.8292 0.7641 0.8889 0.046 Uiso 1 1 calc R . . . .
C00V C 0.6711(2) 0.2257(4) 0.63931(17) 0.0432(9) Uani 1 1 d D . . . .
H00J H 0.7216 0.2576 0.6400 0.052 Uiso 1 1 calc DR . . . .
H00M H 0.6615 0.1164 0.6481 0.052 Uiso 1 1 calc DR . . . .
C00W C 0.82186(19) 1.0185(4) 0.5817(2) 0.0412(9) Uani 1 1 d D . . . .
H00X H 0.8530 1.0784 0.6235 0.049 Uiso 1 1 calc DR . . . .
C00X C 1.19430(19) 0.8255(4) 0.67895(18) 0.0437(9) Uani 1 1 d D . . . .
H00Y H 1.1931 0.9368 0.6671 0.052 Uiso 1 1 calc DR . . . .
H H 1.2428 0.7686 0.6946 0.052 Uiso 1 1 calc DR . . . .
C00Y C 0.8122(2) 1.0767(5) 0.5152(2) 0.0632(12) Uani 1 1 d D . . . .
H00Z H 0.7813 1.0191 0.4725 0.076 Uiso 1 1 calc DR . . . .
HA H 0.8362 1.1758 0.5104 0.076 Uiso 1 1 calc DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O003 1.515(2) . ?
S001 C00B 1.746(3) . ?
S001 C00J 1.812(3) . ?
S002 O004 1.512(2) . ?
S002 C00H 1.742(3) . ?
S002 C00R 1.811(3) . ?
N005 H005 0.8600 . ?
N005 C008 1.362(3) . ?
N005 C009 1.381(3) . ?
N006 H006 0.8600 . ?
N006 C00D 1.382(3) . ?
N006 C00F 1.366(3) . ?
C007 C009 1.411(3) . ?
C007 C00A 1.396(4) . ?
C007 C00B 1.440(4) . ?
C008 C00B 1.381(4) . ?
C008 C00C 1.491(4) . ?
C009 C00K 1.392(4) . ?
C00A H00A 0.9300 . ?
C00A C00I 1.379(4) . ?
C00C H00B 0.9700 . ?
C00C H00C 0.9700 . ?
C00C C00G 1.499(4) . ?
C00D C00E 1.410(4) . ?
C00D C00P 1.392(4) . ?
C00E C00H 1.442(4) . ?
C00E C00M 1.398(4) . ?
C00F C00H 1.373(4) . ?
C00F C00O 1.495(4) . ?
C00G H00G 0.9300 . ?
C00G C00Q 1.305(4) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.398(4) . ?
C00J H00D 0.9700 . ?
C00J H00E 0.9700 . ?
C00J C00N 1.491(4) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.369(4) . ?
C00L H00L 0.9300 . ?
C00M H00O 0.9300 . ?
C00M C00U 1.376(4) . ?
C00N H00N 0.9300 . ?
C00N C00V 1.292(4) . ?
C00O H00P 0.9700 . ?
C00O H00Q 0.9700 . ?
C00O C00T 1.495(4) . ?
C00P H00R 0.9300 . ?
C00P C00S 1.374(4) . ?
C00Q H00F 0.9300 . ?
C00Q H00H 0.9300 . ?
C00R H00S 0.9700 . ?
C00R H00T 0.9700 . ?
C00R C00W 1.488(4) . ?
C00S H00U 0.9300 . ?
C00S C00U 1.396(4) . ?
C00T H00V 0.9300 . ?
C00T C00X 1.299(4) . ?
C00U H00W 0.9300 . ?
C00V H00J 0.9300 . ?
C00V H00M 0.9300 . ?
C00W H00X 0.9300 . ?
C00W C00Y 1.305(4) . ?
C00X H00Y 0.9300 . ?
C00X H 0.9300 . ?
C00Y H00Z 0.9300 . ?
C00Y HA 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O003 S001 C00B 109.15(12) . . ?
O003 S001 C00J 103.74(12) . . ?
C00B S001 C00J 100.71(13) . . ?
O004 S002 C00H 107.62(13) . . ?
O004 S002 C00R 106.14(13) . . ?
C00H S002 C00R 99.67(15) . . ?
C008 N005 H005 124.9 . . ?
C008 N005 C009 110.2(2) . . ?
C009 N005 H005 124.9 . . ?
C00D N006 H006 125.2 . . ?
C00F N006 H006 125.2 . . ?
C00F N006 C00D 109.5(2) . . ?
C009 C007 C00B 105.6(2) . . ?
C00A C007 C009 118.3(3) . . ?
C00A C007 C00B 136.1(2) . . ?
N005 C008 C00B 108.3(2) . . ?
N005 C008 C00C 120.6(2) . . ?
C00B C008 C00C 131.1(2) . . ?
N005 C009 C007 107.8(2) . . ?
N005 C009 C00K 129.5(2) . . ?
C00K C009 C007 122.6(3) . . ?
C007 C00A H00A 120.5 . . ?
C00I C00A C007 119.1(3) . . ?
C00I C00A H00A 120.5 . . ?
C007 C00B S001 130.1(2) . . ?
C008 C00B S001 121.8(2) . . ?
C008 C00B C007 108.1(2) . . ?
C008 C00C H00B 109.2 . . ?
C008 C00C H00C 109.2 . . ?
C008 C00C C00G 112.2(2) . . ?
H00B C00C H00C 107.9 . . ?
C00G C00C H00B 109.2 . . ?
C00G C00C H00C 109.2 . . ?
N006 C00D C00E 108.1(2) . . ?
N006 C00D C00P 129.9(3) . . ?
C00P C00D C00E 122.0(3) . . ?
C00D C00E C00H 105.6(2) . . ?
C00M C00E C00D 118.9(3) . . ?
C00M C00E C00H 135.5(3) . . ?
N006 C00F C00H 108.9(2) . . ?
N006 C00F C00O 121.0(2) . . ?
C00H C00F C00O 130.1(3) . . ?
C00C C00G H00G 117.5 . . ?
C00Q C00G C00C 125.0(3) . . ?
C00Q C00G H00G 117.5 . . ?
C00E C00H S002 127.8(2) . . ?
C00F C00H S002 124.2(2) . . ?
C00F C00H C00E 107.9(3) . . ?
C00A C00I H00I 119.3 . . ?
C00A C00I C00L 121.3(3) . . ?
C00L C00I H00I 119.3 . . ?
S001 C00J H00D 108.9 . . ?
S001 C00J H00E 108.9 . . ?
H00D C00J H00E 107.7 . . ?
C00N C00J S001 113.5(2) . . ?
C00N C00J H00D 108.9 . . ?
C00N C00J H00E 108.9 . . ?
C009 C00K H00K 121.2 . . ?
C00L C00K C009 117.5(3) . . ?
C00L C00K H00K 121.2 . . ?
C00I C00L H00L 119.4 . . ?
C00K C00L C00I 121.1(3) . . ?
C00K C00L H00L 119.4 . . ?
C00E C00M H00O 120.4 . . ?
C00U C00M C00E 119.2(3) . . ?
C00U C00M H00O 120.4 . . ?
C00J C00N H00N 117.8 . . ?
C00V C00N C00J 124.4(3) . . ?
C00V C00N H00N 117.8 . . ?
C00F C00O H00P 108.8 . . ?
C00F C00O H00Q 108.8 . . ?
H00P C00O H00Q 107.7 . . ?
C00T C00O C00F 113.7(3) . . ?
C00T C00O H00P 108.8 . . ?
C00T C00O H00Q 108.8 . . ?
C00D C00P H00R 121.4 . . ?
C00S C00P C00D 117.2(3) . . ?
C00S C00P H00R 121.4 . . ?
C00G C00Q H00F 120.0 . . ?
C00G C00Q H00H 120.0 . . ?
H00F C00Q H00H 120.0 . . ?
S002 C00R H00S 109.8 . . ?
S002 C00R H00T 109.8 . . ?
H00S C00R H00T 108.2 . . ?
C00W C00R S002 109.5(2) . . ?
C00W C00R H00S 109.8 . . ?
C00W C00R H00T 109.8 . . ?
C00P C00S H00U 119.0 . . ?
C00P C00S C00U 122.0(3) . . ?
C00U C00S H00U 119.0 . . ?
C00O C00T H00V 117.7 . . ?
C00X C00T C00O 124.6(3) . . ?
C00X C00T H00V 117.7 . . ?
C00M C00U C00S 120.6(3) . . ?
C00M C00U H00W 119.7 . . ?
C00S C00U H00W 119.7 . . ?
C00N C00V H00J 120.0 . . ?
C00N C00V H00M 120.0 . . ?
H00J C00V H00M 120.0 . . ?
C00R C00W H00X 118.4 . . ?
C00Y C00W C00R 123.1(3) . . ?
C00Y C00W H00X 118.4 . . ?
C00T C00X H00Y 120.0 . . ?
C00T C00X H 120.0 . . ?
H00Y C00X H 120.0 . . ?
C00W C00Y H00Z 120.0 . . ?
C00W C00Y HA 120.0 . . ?
H00Z C00Y HA 120.0 . . ?

_olex2_date_sample_data_collection 2017-05-30
_olex2_submission_original_sample_id 
'Sulfenylation Product - diallylsulfoxide/indole'
_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 1.077
_oxdiff_exptl_absorpt_empirical_full_min 0.937
####################################################################### 
# 
# 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_odjp11
_database_code_depnum_ccdc_archive 'CCDC 1570698'
_audit_update_record             
;
2017-08-24 deposited with the CCDC.
2017-11-17 downloaded from the CCDC.
;
_audit_creation_date             2017-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        2-Allyl-3-(allylsulfinyl)-1-methyl-1H-indole
_chemical_formula_moiety         'C15 H17 N O S'
_chemical_formula_sum            'C15 H17 N O S'
_chemical_formula_weight         259.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H17NSO
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                   8.2973(5)
_cell_length_b                   9.1320(6)
_cell_length_c                   9.7066(5)
_cell_angle_alpha                104.937(5)
_cell_angle_beta                 100.291(5)
_cell_angle_gamma                100.461(5)
_cell_volume                     678.86(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2819
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.2800
_cell_measurement_theta_min      4.3850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.42676
_exptl_crystal_size_mid          0.27785
_exptl_crystal_size_min          0.22233
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4526
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.721
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1636
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  79.00   1.00    1.00    --   11.69  57.00 -90.00   96
  2  ω    -16.00  71.00   1.00    1.00    --   11.69  77.00  30.00   87
  3  ω    -60.00  33.00   1.00    1.00    --   11.69 -57.00 120.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0527020000
_diffrn_orient_matrix_UB_12      0.0164039000
_diffrn_orient_matrix_UB_13      0.0709267000
_diffrn_orient_matrix_UB_21      0.0395682000
_diffrn_orient_matrix_UB_22      -0.0602305000
_diffrn_orient_matrix_UB_23      -0.0275945000
_diffrn_orient_matrix_UB_31      0.0605360000
_diffrn_orient_matrix_UB_32      0.0543909000
_diffrn_orient_matrix_UB_33      -0.0164037000
_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              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2102
_reflns_number_total             2471
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+0.1692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0942
_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:
 C00A(H00A,H00B), C00C(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00C), C00D(H00F), C00F(H00J), C00G(H00K)
2.c Idealised Me refined as rotating group:
 C00E(H00G,H00H,H00I)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.75939(5) 0.83841(5) 0.42402(5) 0.02707(16) Uani 1 1 d . . . . .
O002 O 0.87637(16) 0.83766(16) 0.56069(14) 0.0393(4) Uani 1 1 d . . . . .
N003 N 0.35693(17) 0.49218(18) 0.28439(15) 0.0243(3) Uani 1 1 d . . . . .
C004 C 0.4366(2) 0.6465(2) 0.32133(18) 0.0230(4) Uani 1 1 d . . . . .
C005 C 0.4755(2) 0.4056(2) 0.30036(18) 0.0232(4) Uani 1 1 d . . . . .
C006 C 0.6084(2) 0.6608(2) 0.35909(18) 0.0235(4) Uani 1 1 d . . . . .
C007 C 0.6361(2) 0.5085(2) 0.34750(17) 0.0229(4) Uani 1 1 d . . . . .
C008 C 0.7787(2) 0.4486(2) 0.37521(18) 0.0263(4) Uani 1 1 d . . . . .
H008 H 0.8885 0.5160 0.4092 0.032 Uiso 1 1 calc R . . . .
C009 C 0.4531(2) 0.2463(2) 0.27837(19) 0.0295(4) Uani 1 1 d . . . . .
H009 H 0.3436 0.1783 0.2475 0.035 Uiso 1 1 calc R . . . .
C00A C 0.3429(2) 0.7697(2) 0.31515(19) 0.0282(4) Uani 1 1 d . . . . .
H00A H 0.4188 0.8722 0.3738 0.034 Uiso 1 1 calc R . . . .
H00B H 0.2473 0.7521 0.3619 0.034 Uiso 1 1 calc R . . . .
C00B C 0.5958(2) 0.1905(2) 0.3030(2) 0.0317(4) Uani 1 1 d . . . . .
H00C H 0.5845 0.0815 0.2861 0.038 Uiso 1 1 calc R . . . .
C00C C 0.8791(2) 0.8090(2) 0.2832(2) 0.0328(5) Uani 1 1 d . . . . .
H00D H 0.9891 0.8865 0.3187 0.039 Uiso 1 1 calc R . . . .
H00E H 0.9014 0.7036 0.2646 0.039 Uiso 1 1 calc R . . . .
C00D C 0.7567(2) 0.2909(2) 0.35234(19) 0.0297(4) Uani 1 1 d . . . . .
H00F H 0.8526 0.2493 0.3703 0.036 Uiso 1 1 calc R . . . .
C00E C 0.1754(2) 0.4244(2) 0.2385(2) 0.0331(5) Uani 1 1 d . . . . .
H00G H 0.1153 0.5081 0.2516 0.050 Uiso 1 1 calc GR . . . .
H00H H 0.1437 0.3571 0.2981 0.050 Uiso 1 1 calc GR . . . .
H00I H 0.1452 0.3624 0.1348 0.050 Uiso 1 1 calc GR . . . .
C00F C 0.2753(2) 0.7771(3) 0.1635(2) 0.0371(5) Uani 1 1 d . . . . .
H00J H 0.2107 0.8519 0.1560 0.044 Uiso 1 1 calc R . . . .
C00G C 0.7865(3) 0.8252(3) 0.1443(2) 0.0402(5) Uani 1 1 d . . . . .
H00K H 0.6946 0.7421 0.0838 0.048 Uiso 1 1 calc R . . . .
C00H C 0.2962(3) 0.6912(3) 0.0411(3) 0.0502(6) Uani 1 1 d . . . . .
C00I C 0.8258(4) 0.9483(3) 0.1016(3) 0.0574(7) Uani 1 1 d . . . . .
H00N H 0.921(4) 1.031(4) 0.156(3) 0.073(9) Uiso 1 1 d . . . . .
H00L H 0.362(3) 0.614(3) 0.040(3) 0.061(8) Uiso 1 1 d . . . . .
H00O H 0.762(3) 0.960(3) 0.017(3) 0.072(8) Uiso 1 1 d . . . . .
H00M H 0.253(3) 0.701(3) -0.049(3) 0.063(8) Uiso 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
S001 O002 1.4996(13) . ?
S001 C006 1.7464(18) . ?
S001 C00C 1.8218(19) . ?
N003 C004 1.367(2) . ?
N003 C005 1.382(2) . ?
N003 C00E 1.460(2) . ?
C004 C006 1.380(2) . ?
C004 C00A 1.487(3) . ?
C005 C007 1.405(2) . ?
C005 C009 1.387(3) . ?
C006 C007 1.430(3) . ?
C007 C008 1.403(2) . ?
C008 H008 0.9500 . ?
C008 C00D 1.371(3) . ?
C009 H009 0.9500 . ?
C009 C00B 1.378(3) . ?
C00A H00A 0.9900 . ?
C00A H00B 0.9900 . ?
C00A C00F 1.502(3) . ?
C00B H00C 0.9500 . ?
C00B C00D 1.398(3) . ?
C00C H00D 0.9900 . ?
C00C H00E 0.9900 . ?
C00C C00G 1.485(3) . ?
C00D H00F 0.9500 . ?
C00E H00G 0.9800 . ?
C00E H00H 0.9800 . ?
C00E H00I 0.9800 . ?
C00F H00J 0.9500 . ?
C00F C00H 1.304(3) . ?
C00G H00K 0.9500 . ?
C00G C00I 1.303(3) . ?
C00H H00L 0.96(3) . ?
C00H H00M 0.91(3) . ?
C00I H00N 0.95(3) . ?
C00I H00O 0.94(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
O002 S001 C006 107.72(8) . . ?
O002 S001 C00C 105.01(9) . . ?
C006 S001 C00C 99.50(8) . . ?
C004 N003 C005 109.49(14) . . ?
C004 N003 C00E 126.97(15) . . ?
C005 N003 C00E 123.52(16) . . ?
N003 C004 C006 108.46(16) . . ?
N003 C004 C00A 122.40(15) . . ?
C006 C004 C00A 129.12(16) . . ?
N003 C005 C007 108.02(16) . . ?
N003 C005 C009 129.73(16) . . ?
C009 C005 C007 122.24(17) . . ?
C004 C006 S001 124.41(14) . . ?
C004 C006 C007 107.94(15) . . ?
C007 C006 S001 127.44(13) . . ?
C005 C007 C006 106.07(15) . . ?
C008 C007 C005 118.96(17) . . ?
C008 C007 C006 134.94(16) . . ?
C007 C008 H008 120.6 . . ?
C00D C008 C007 118.84(17) . . ?
C00D C008 H008 120.6 . . ?
C005 C009 H009 121.3 . . ?
C00B C009 C005 117.44(17) . . ?
C00B C009 H009 121.3 . . ?
C004 C00A H00A 108.5 . . ?
C004 C00A H00B 108.5 . . ?
C004 C00A C00F 114.94(16) . . ?
H00A C00A H00B 107.5 . . ?
C00F C00A H00A 108.5 . . ?
C00F C00A H00B 108.5 . . ?
C009 C00B H00C 119.3 . . ?
C009 C00B C00D 121.34(19) . . ?
C00D C00B H00C 119.3 . . ?
S001 C00C H00D 109.3 . . ?
S001 C00C H00E 109.3 . . ?
H00D C00C H00E 108.0 . . ?
C00G C00C S001 111.40(13) . . ?
C00G C00C H00D 109.3 . . ?
C00G C00C H00E 109.3 . . ?
C008 C00D C00B 121.14(18) . . ?
C008 C00D H00F 119.4 . . ?
C00B C00D H00F 119.4 . . ?
N003 C00E H00G 109.5 . . ?
N003 C00E H00H 109.5 . . ?
N003 C00E H00I 109.5 . . ?
H00G C00E H00H 109.5 . . ?
H00G C00E H00I 109.5 . . ?
H00H C00E H00I 109.5 . . ?
C00A C00F H00J 116.7 . . ?
C00H C00F C00A 126.5(2) . . ?
C00H C00F H00J 116.7 . . ?
C00C C00G H00K 118.6 . . ?
C00I C00G C00C 122.9(2) . . ?
C00I C00G H00K 118.6 . . ?
C00F C00H H00L 121.7(15) . . ?
C00F C00H H00M 123.2(17) . . ?
H00L C00H H00M 115(2) . . ?
C00G C00I H00N 120.8(17) . . ?
C00G C00I H00O 121.9(17) . . ?
H00N C00I H00O 117(2) . . ?

_olex2_date_sample_data_collection 2017-06-07
_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 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.736
