# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_t0104m
_database_code_depnum_ccdc_archive 'CCDC 1507060'
_audit_update_record             
;
2016-09-28 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;
_audit_creation_date             2016-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         '0.17(C24 H19 N O2 S)'
_chemical_formula_sum            'C4 H3.167 N0.167 O0.333 S0.167'
_chemical_formula_weight         64.25
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   16.382(4)
_cell_length_b                   18.322(4)
_cell_length_c                   14.538(3)
_cell_angle_alpha                90
_cell_angle_beta                 120.472(3)
_cell_angle_gamma                90
_cell_volume                     3760.7(14)
_cell_formula_units_Z            48
_cell_measurement_reflns_used    4351
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.49
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_min  0.889113
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0619 before and 0.0346 after correction.
The Ratio of minimum to maximum transmission is 0.8891.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.3616
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             1617.6825
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16691
_diffrn_reflns_theta_full        28.8708
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         1.82
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9293
_diffrn_measured_fraction_theta_max 0.9293
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -21
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3305
_reflns_number_total             4601
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.4814
_refine_diff_density_min         -0.3235
_refine_diff_density_rms         0.0698
_refine_ls_d_res_high            0.7360
_refine_ls_d_res_low             11.1837
_refine_ls_goodness_of_fit_ref   1.1214
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.1214
_refine_ls_shift/su_max          4.5794
_refine_ls_shift/su_mean         0.1934
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1710
_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:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
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_refinement_flags_posn
S1 S 0.04879(3) 0.29530(3) 0.56519(4) 0.04815(19) Uani 1.000000 .
N1 N -0.08895(10) 0.37223(8) 0.28237(12) 0.0376(4) Uani 1.000000 .
C2 C -0.10516(12) 0.30019(9) 0.25433(15) 0.0348(4) Uani 1.000000 .
C3 C -0.16573(12) 0.29419(9) 0.13644(14) 0.0363(4) Uani 1.000000 .
C4 C -0.06021(11) 0.25875(10) 0.34421(14) 0.0366(4) Uani 1.000000 .
C5 C -0.06619(12) 0.17916(10) 0.34528(13) 0.0387(4) Uani 1.000000 .
C6 C -0.03199(12) 0.25358(11) 0.59365(13) 0.0394(4) Uani 1.000000 .
O7 O 0.07404(11) 0.36480(9) 0.61582(12) 0.0629(4) Uani 1.000000 .
C8 C -0.18033(12) 0.37254(10) 0.10375(15) 0.0381(4) Uani 1.000000 .
C9 C -0.01546(12) 0.31050(11) 0.42908(15) 0.0411(4) Uani 1.000000 .
C10 C -0.03491(12) 0.37926(11) 0.38853(15) 0.0429(4) Uani 1.000000 .
C11 C -0.16052(12) 0.19117(11) 0.63884(14) 0.0412(4) Uani 1.000000 .
O12 O 0.12273(9) 0.24421(9) 0.58947(12) 0.0618(4) Uani 1.000000 .
C13 C -0.13505(12) 0.41742(10) 0.19177(15) 0.0405(4) Uani 1.000000 .
C14 C -0.15461(14) 0.14645(10) 0.29050(15) 0.0445(4) Uani 1.000000 .
C15 C -0.08807(15) 0.29652(11) 0.61521(18) 0.0529(5) Uani 1.000000 .
C16 C -0.03878(14) 0.17993(11) 0.59511(17) 0.0509(5) Uani 1.000000 .
C17 C -0.10288(16) 0.14934(12) 0.61745(18) 0.0542(5) Uani 1.000000 .
C18 C -0.23065(14) 0.40298(11) 0.00404(17) 0.0488(5) Uani 1.000000 .
C19 C -0.13930(15) 0.49160(11) 0.18501(18) 0.0536(5) Uani 1.000000 .
C20 C -0.15247(14) 0.26517(12) 0.63679(17) 0.0523(5) Uani 1.000000 .
C21 C 0.01202(15) 0.13489(11) 0.39625(17) 0.0518(5) Uani 1.000000 .
C22 C -0.22914(15) 0.15805(12) 0.66531(18) 0.0568(6) Uani 1.000000 .
C23 C -0.16322(17) 0.07226(12) 0.28934(18) 0.0582(6) Uani 1.000000 .
C24 C -0.23577(17) 0.47746(12) -0.0039(2) 0.0616(6) Uani 1.000000 .
C25 C -0.19259(17) 0.52095(12) 0.0841(2) 0.0642(6) Uani 1.000000 .
C26 C 0.00304(18) 0.06078(12) 0.39429(19) 0.0630(6) Uani 1.000000 .
C27 C -0.0844(2) 0.02899(13) 0.34120(19) 0.0661(6) Uani 1.000000 .
H16 H -0.00017(14) 0.15046(11) 0.58103(17) 0.0610(6) Uiso 1.000000 R
H17 H -0.10745(16) 0.09877(12) 0.61813(18) 0.0650(6) Uiso 1.000000 R
H20 H -0.19132(14) 0.29482(12) 0.65025(17) 0.0628(6) Uiso 1.000000 R
H15 H -0.08266(15) 0.34705(11) 0.61530(18) 0.0635(6) Uiso 1.000000 R
H21 H 0.07204(15) 0.15574(11) 0.43266(17) 0.0622(6) Uiso 1.000000 R
H26 H 0.05685(18) 0.03170(12) 0.42938(19) 0.0756(7) Uiso 1.000000 R
H27 H -0.0903(2) -0.02152(13) 0.34025(19) 0.0793(8) Uiso 1.000000 R
H23 H -0.22298(17) 0.05097(12) 0.25311(18) 0.0698(7) Uiso 1.000000 R
H14 H -0.20854(14) 0.17527(10) 0.25424(15) 0.0534(5) Uiso 1.000000 R
H19 H -0.10790(15) 0.52097(11) 0.24529(18) 0.0643(6) Uiso 1.000000 R
H25 H -0.19915(17) 0.57134(12) 0.0761(2) 0.0771(8) Uiso 1.000000 R
H24 H -0.26953(17) 0.49889(12) -0.0711(2) 0.0739(7) Uiso 1.000000 R
H18 H -0.26052(14) 0.37379(11) -0.05658(17) 0.0586(6) Uiso 1.000000 R
H3a H -0.13369(12) 0.26803(9) 0.10581(14) 0.0435(5) Uiso 1.000000 R
H3b H -0.22530(12) 0.27015(9) 0.11608(14) 0.0435(5) Uiso 1.000000 R
H10 H -0.01472(12) 0.42265(11) 0.42686(15) 0.0515(5) Uiso 1.000000 R
H22a H -0.2910(3) 0.1571(8) 0.6026(3) 0.0852(8) Uiso 1.000000 GR
H22b H -0.2097(6) 0.1091(3) 0.6907(11) 0.0852(8) Uiso 1.000000 GR
H22c H -0.2309(8) 0.1865(5) 0.7197(9) 0.0852(8) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7500(18) . ?
S1 O7 1.4230(16) . ?
S1 C9 1.729(2) . ?
S1 O12 1.4265(15) . ?
N1 C2 1.367(2) . ?
N1 C10 1.340(2) . ?
N1 C13 1.408(2) . ?
C2 C3 1.486(2) . ?
C2 C4 1.360(2) . ?
C3 C8 1.493(2) . ?
C4 C5 1.462(3) . ?
C4 C9 1.429(2) . ?
C5 C14 1.386(2) . ?
C5 C21 1.373(3) . ?
C6 C15 1.361(3) . ?
C6 C16 1.355(3) . ?
C8 C13 1.379(3) . ?
C8 C18 1.371(3) . ?
C9 C10 1.359(3) . ?
C11 C17 1.369(3) . ?
C11 C20 1.364(3) . ?
C11 C22 1.490(3) . ?
C13 C19 1.362(3) . ?
C14 C23 1.366(3) . ?
C15 C20 1.370(3) . ?
C16 C17 1.367(3) . ?
C18 C24 1.368(3) . ?
C19 C25 1.380(3) . ?
C21 C26 1.365(3) . ?
C23 C27 1.370(3) . ?
C24 C25 1.362(3) . ?
C26 C27 1.365(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
O7 S1 C6 108.96(9) . . ?
C9 S1 C6 104.27(8) . . ?
C9 S1 O7 107.24(9) . . ?
O12 S1 C6 107.69(9) . . ?
O12 S1 O7 118.14(10) . . ?
O12 S1 C9 109.67(9) . . ?
C10 N1 C2 110.56(15) . . ?
C13 N1 C2 110.98(15) . . ?
C13 N1 C10 138.45(16) . . ?
C3 C2 N1 109.29(14) . . ?
C4 C2 N1 108.89(16) . . ?
C4 C2 C3 141.81(16) . . ?
C8 C3 C2 101.62(14) . . ?
C5 C4 C2 124.08(16) . . ?
C9 C4 C2 104.47(16) . . ?
C9 C4 C5 131.33(16) . . ?
C14 C5 C4 118.76(16) . . ?
C21 C5 C4 123.06(17) . . ?
C21 C5 C14 118.16(18) . . ?
C15 C6 S1 118.78(15) . . ?
C16 C6 S1 121.11(14) . . ?
C16 C6 C15 120.11(18) . . ?
C13 C8 C3 110.74(16) . . ?
C18 C8 C3 129.88(18) . . ?
C18 C8 C13 119.38(17) . . ?
C4 C9 S1 129.02(15) . . ?
C10 C9 S1 121.25(15) . . ?
C10 C9 C4 109.63(17) . . ?
C9 C10 N1 106.44(16) . . ?
C20 C11 C17 117.78(17) . . ?
C22 C11 C17 121.91(18) . . ?
C22 C11 C20 120.30(17) . . ?
C8 C13 N1 107.36(15) . . ?
C19 C13 N1 129.65(18) . . ?
C19 C13 C8 122.98(18) . . ?
C23 C14 C5 120.57(19) . . ?
C20 C15 C6 119.89(19) . . ?
C17 C16 C6 119.42(18) . . ?
C16 C17 C11 121.73(19) . . ?
C24 C18 C8 118.3(2) . . ?
C25 C19 C13 116.6(2) . . ?
C15 C20 C11 121.06(18) . . ?
C26 C21 C5 121.0(2) . . ?
C27 C23 C14 120.4(2) . . ?
C25 C24 C18 121.6(2) . . ?
C24 C25 C19 121.2(2) . . ?
C27 C26 C21 120.5(2) . . ?
C26 C27 C23 119.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        1-phenyl-2-tosyl-9H-pyrrolo[1,2-a]indole
