# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_KA115_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1864240'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
5-(3-methoxyphenyl)-3-(methylsulfonyl)-2-(tosylmethyl)-3,4-dihydrobenzo[f]isoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H27 N O5 S2'
_chemical_formula_sum            'C29 H27 N O5 S2'
_chemical_formula_weight         533.63

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.943(6)
_cell_length_b                   10.893(5)
_cell_length_c                   16.259(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.199(10)
_cell_angle_gamma                90
_cell_volume                     2646.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.506
_cell_measurement_theta_max      35.492

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6487
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19517
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5202
_reflns_number_gt                4388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0765P)²+0.5985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5202
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65573(3) 0.39026(5) 0.28768(3) 0.04300(15) Uani 1 1 d . . . . .
O1 O 0.27731(11) 0.03595(15) 0.52719(11) 0.0653(5) Uani 1 1 d . . . . .
N1 N 0.55957(10) 0.34457(14) 0.24650(8) 0.0337(3) Uani 1 1 d . . . . .
C1 C 0.34655(14) 0.11751(19) 0.52625(12) 0.0446(5) Uani 1 1 d . . . . .
S2 S 0.52470(3) 0.29623(4) 0.02840(2) 0.03314(14) Uani 1 1 d . . . . .
O2 O 0.66878(11) 0.32075(16) 0.36051(10) 0.0625(5) Uani 1 1 d . . . . .
C2 C 0.33452(13) 0.21716(18) 0.47370(11) 0.0401(4) Uani 1 1 d . . . . .
H2 H 0.281574 0.224657 0.443896 0.048 Uiso 1 1 calc R U . . .
O3 O 0.72095(10) 0.3846(2) 0.22480(10) 0.0743(6) Uani 1 1 d . . . . .
C3 C 0.40073(13) 0.30513(17) 0.46547(10) 0.0360(4) Uani 1 1 d . . . . .
O4 O 0.57952(10) 0.29948(13) -0.04424(7) 0.0480(4) Uani 1 1 d . . . . .
C4 C 0.47976(15) 0.2929(2) 0.51119(12) 0.0505(5) Uani 1 1 d . . . . .
H4 H 0.524912 0.351195 0.506516 0.061 Uiso 1 1 calc R U . . .
O5 O 0.43105(9) 0.32339(13) 0.02034(8) 0.0463(3) Uani 1 1 d . . . . .
C5 C 0.49033(17) 0.1940(2) 0.56315(14) 0.0585(6) Uani 1 1 d . . . . .
H5 H 0.542897 0.186397 0.593515 0.070 Uiso 1 1 calc R U . . .
C6 C 0.42437(15) 0.1058(2) 0.57106(12) 0.0517(5) Uani 1 1 d . . . . .
H6 H 0.432498 0.039378 0.606235 0.062 Uiso 1 1 calc R U . . .
C7 C 0.28884(19) -0.0746(2) 0.57236(17) 0.0655(7) Uani 1 1 d . . . . .
H7A H 0.339279 -0.118835 0.551101 0.098 Uiso 1 1 calc R U . . .
H7B H 0.235983 -0.124126 0.567243 0.098 Uiso 1 1 calc R U . . .
H7C H 0.299061 -0.055505 0.629267 0.098 Uiso 1 1 calc R U . . .
C8 C 0.38723(12) 0.40933(17) 0.40738(10) 0.0333(4) Uani 1 1 d . . . . .
C9 C 0.33252(12) 0.50510(18) 0.42653(10) 0.0372(4) Uani 1 1 d . . . . .
H9 H 0.304933 0.505997 0.477713 0.045 Uiso 1 1 calc R U . . .
C10 C 0.31604(11) 0.60327(17) 0.37155(10) 0.0338(4) Uani 1 1 d . . . . .
C11 C 0.26340(13) 0.70494(19) 0.39441(12) 0.0432(5) Uani 1 1 d . . . . .
H11 H 0.238738 0.707843 0.446808 0.052 Uiso 1 1 calc R U . . .
C12 C 0.24803(14) 0.7990(2) 0.34102(14) 0.0506(5) Uani 1 1 d . . . . .
H12 H 0.213682 0.865925 0.357271 0.061 Uiso 1 1 calc R U . . .
C13 C 0.28410(14) 0.7950(2) 0.26137(13) 0.0482(5) Uani 1 1 d . . . . .
H13 H 0.272695 0.858901 0.224881 0.058 Uiso 1 1 calc R U . . .
C14 C 0.33584(12) 0.69806(18) 0.23690(12) 0.0401(4) Uani 1 1 d . . . . .
H14 H 0.359144 0.696824 0.183946 0.048 Uiso 1 1 calc R U . . .
C15 C 0.35431(11) 0.59971(16) 0.29119(10) 0.0312(4) Uani 1 1 d . . . . .
C16 C 0.41159(11) 0.49874(16) 0.27134(10) 0.0301(4) Uani 1 1 d . . . . .
C17 C 0.42850(12) 0.40766(16) 0.32858(10) 0.0314(4) Uani 1 1 d . . . . .
C18 C 0.48798(13) 0.30336(17) 0.30269(11) 0.0376(4) Uani 1 1 d . . . . .
H18A H 0.514826 0.266417 0.351122 0.045 Uiso 1 1 calc R U . . .
H18B H 0.452106 0.241181 0.275427 0.045 Uiso 1 1 calc R U . . .
C19 C 0.45425(11) 0.48730(16) 0.19038(10) 0.0307(4) Uani 1 1 d . . . . .
H19 H 0.430538 0.530509 0.146043 0.037 Uiso 1 1 calc R U . . .
C20 C 0.52605(12) 0.41667(16) 0.17871(10) 0.0304(4) Uani 1 1 d . . . . .
C21 C 0.6430(2) 0.5451(2) 0.31576(19) 0.0750(8) Uani 1 1 d . . . . .
H21A H 0.699315 0.576855 0.334759 0.113 Uiso 1 1 calc R U . . .
H21B H 0.599535 0.551497 0.358903 0.113 Uiso 1 1 calc R U . . .
H21C H 0.623144 0.591585 0.268955 0.113 Uiso 1 1 calc R U . . .
C22 C 0.57325(12) 0.40532(17) 0.09800(10) 0.0335(4) Uani 1 1 d . . . . .
H22A H 0.634917 0.382046 0.108404 0.040 Uiso 1 1 calc R U . . .
H22B H 0.573819 0.485163 0.071590 0.040 Uiso 1 1 calc R U . . .
C23 C 0.53719(12) 0.15156(16) 0.07466(10) 0.0324(4) Uani 1 1 d . . . . .
C24 C 0.47090(13) 0.10563(18) 0.12462(12) 0.0432(5) Uani 1 1 d . . . . .
H24 H 0.418293 0.149533 0.132762 0.052 Uiso 1 1 calc R U . . .
C25 C 0.48368(15) -0.0066(2) 0.16246(14) 0.0490(5) Uani 1 1 d . . . . .
H25 H 0.439678 -0.036799 0.197368 0.059 Uiso 1 1 calc R U . . .
C26 C 0.55992(13) -0.07500(18) 0.14980(11) 0.0393(4) Uani 1 1 d . . . . .
C27 C 0.62413(14) -0.0282(2) 0.09735(13) 0.0485(5) Uani 1 1 d . . . . .
H27 H 0.675494 -0.073916 0.087160 0.058 Uiso 1 1 calc R U . . .
C28 C 0.61389(14) 0.0842(2) 0.05988(12) 0.0457(5) Uani 1 1 d . . . . .
H28 H 0.657956 0.114392 0.025085 0.055 Uiso 1 1 calc R U . . .
C29 C 0.57428(17) -0.1966(2) 0.19127(14) 0.0553(6) Uani 1 1 d . . . . .
H29A H 0.519058 -0.223971 0.215035 0.083 Uiso 1 1 calc R U . . .
H29B H 0.618626 -0.187880 0.233739 0.083 Uiso 1 1 calc R U . . .
H29C H 0.594350 -0.255607 0.151565 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4161(17) . ?
S1 O2 1.4185(15) . ?
S1 N1 1.6596(17) . ?
S1 C21 1.758(3) . ?
O1 C1 1.364(3) . ?
O1 C7 1.421(3) . ?
N1 C20 1.442(2) . ?
N1 C18 1.479(2) . ?
C1 C6 1.376(3) . ?
C1 C2 1.393(3) . ?
S2 O5 1.4358(15) . ?
S2 O4 1.4402(14) . ?
S2 C23 1.7558(19) . ?
S2 C22 1.7927(19) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(3) . ?
C3 C8 1.490(2) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.362(3) . ?
C8 C17 1.424(2) . ?
C9 C10 1.415(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.409(3) . ?
C10 C15 1.429(2) . ?
C11 C12 1.362(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.405(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.415(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.431(2) . ?
C16 C17 1.383(2) . ?
C16 C19 1.470(2) . ?
C17 C18 1.503(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.334(2) . ?
C19 H19 0.9300 . ?
C20 C22 1.497(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.377(3) . ?
C23 C28 1.383(3) . ?
C24 C25 1.382(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(3) . ?
C26 C29 1.501(3) . ?
C27 C28 1.376(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 119.10(11) . . ?
O3 S1 N1 107.02(9) . . ?
O2 S1 N1 107.04(9) . . ?
O3 S1 C21 107.76(15) . . ?
O2 S1 C21 108.06(13) . . ?
N1 S1 C21 107.35(11) . . ?
C1 O1 C7 117.86(19) . . ?
C20 N1 C18 112.79(14) . . ?
C20 N1 S1 116.30(12) . . ?
C18 N1 S1 117.97(12) . . ?
O1 C1 C6 124.99(19) . . ?
O1 C1 C2 114.73(19) . . ?
C6 C1 C2 120.27(19) . . ?
O5 S2 O4 118.50(9) . . ?
O5 S2 C23 109.03(9) . . ?
O4 S2 C23 108.27(8) . . ?
O5 S2 C22 108.25(9) . . ?
O4 S2 C22 105.74(9) . . ?
C23 S2 C22 106.40(9) . . ?
C3 C2 C1 120.54(18) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 118.99(18) . . ?
C2 C3 C8 119.57(17) . . ?
C4 C3 C8 121.44(17) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.19(19) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C17 118.53(16) . . ?
C9 C8 C3 121.24(15) . . ?
C17 C8 C3 120.17(16) . . ?
C8 C9 C10 122.53(15) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C11 C10 C9 121.57(16) . . ?
C11 C10 C15 119.22(16) . . ?
C9 C10 C15 119.21(16) . . ?
C12 C11 C10 121.09(18) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.95(19) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.73(19) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.80(18) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 118.18(16) . . ?
C14 C15 C16 123.83(15) . . ?
C10 C15 C16 117.95(15) . . ?
C17 C16 C15 120.51(15) . . ?
C17 C16 C19 117.58(15) . . ?
C15 C16 C19 121.91(15) . . ?
C16 C17 C8 121.17(16) . . ?
C16 C17 C18 117.42(14) . . ?
C8 C17 C18 121.33(15) . . ?
N1 C18 C17 111.92(14) . . ?
N1 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
N1 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C16 121.85(15) . . ?
C20 C19 H19 119.1 . . ?
C16 C19 H19 119.1 . . ?
C19 C20 N1 118.86(14) . . ?
C19 C20 C22 123.63(15) . . ?
N1 C20 C22 117.49(15) . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 S2 114.66(13) . . ?
C20 C22 H22A 108.6 . . ?
S2 C22 H22A 108.6 . . ?
C20 C22 H22B 108.6 . . ?
S2 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C28 120.52(17) . . ?
C24 C23 S2 120.20(14) . . ?
C28 C23 S2 119.28(14) . . ?
C23 C24 C25 119.04(18) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 121.67(18) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C27 117.98(18) . . ?
C25 C26 C29 121.79(19) . . ?
C27 C26 C29 120.23(19) . . ?
C28 C27 C26 121.62(18) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 C28 C23 119.11(18) . . ?
C27 C28 H28 120.4 . . ?
C23 C28 H28 120.4 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.046

