# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_jm1121
_database_code_depnum_ccdc_archive 'CCDC 1882045'
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2019-03-11 downloaded from the CCDC.
;
_audit_creation_date             2018-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 I N O2 S Se'
_chemical_formula_sum            'C21 H18 I N O2 S Se'
_chemical_formula_weight         554.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 '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'
Se Se -0.0929 2.2259 '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                   7.8813(4)
_cell_length_b                   9.4987(5)
_cell_length_c                   13.5549(7)
_cell_angle_alpha                95.706(4)
_cell_angle_beta                 92.226(4)
_cell_angle_gamma                91.500(4)
_cell_volume                     1008.50(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1070
_cell_measurement_theta_min      2.5070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.512
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7163
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.156
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -40.00  60.00   1.00    1.00    --  -11.43  77.00   0.00  100
  2  ω     -6.00  88.00   1.00    1.00    --   11.74  77.00 120.00   94
  3  ω    -20.00  88.00   1.00    1.00    --   11.74  77.00 -90.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0716649000
_diffrn_orient_matrix_UB_12      0.0080544000
_diffrn_orient_matrix_UB_13      0.0335985000
_diffrn_orient_matrix_UB_21      0.0532239000
_diffrn_orient_matrix_UB_22      0.0100532000
_diffrn_orient_matrix_UB_23      -0.0398822000
_diffrn_orient_matrix_UB_31      -0.0122750000
_diffrn_orient_matrix_UB_32      0.0739661000
_diffrn_orient_matrix_UB_33      0.0071341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3120
_reflns_number_total             3563
_reflns_odcompleteness_completeness 99.98
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (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         0.754
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.018
_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)+(0.0282P)²+0.0628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0694
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C10(H10), C2(H2), C6(H6), C13(H13), C14(H14), C19(H19),
 C20(H20), C16(H16), C3(H3), C5(H5), C17(H17), C4(H4)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
I1 I 0.84340(3) 0.39423(2) 0.62575(2) 0.02155(10) Uani 1 1 d . . . . .
Se02 Se 0.58969(5) 0.81569(4) 0.52003(3) 0.02420(12) Uani 1 1 d . . . . .
S1 S 0.00637(12) 0.68751(9) 0.91085(7) 0.0164(2) Uani 1 1 d . . . . .
O1 O -0.0442(3) 0.7614(3) 0.82848(18) 0.0214(6) Uani 1 1 d . . . . .
O2 O -0.1228(3) 0.6290(3) 0.96901(17) 0.0182(6) Uani 1 1 d . . . . .
N1 N 0.1157(4) 0.5515(3) 0.8694(3) 0.0164(8) Uani 1 1 d . . . . .
C9 C 0.5333(5) 0.5679(4) 0.6842(3) 0.0156(8) Uani 1 1 d . . . . .
C7 C 0.7093(5) 0.6516(4) 0.5469(3) 0.0177(8) Uani 1 1 d . . . . .
H7 H 0.801718 0.629973 0.508116 0.021 Uiso 1 1 calc R . . . .
C11 C 0.2375(5) 0.6122(3) 0.7159(3) 0.0159(8) Uani 1 1 d . . . . .
H11 H 0.132383 0.642665 0.694534 0.019 Uiso 1 1 calc R . . . .
C10 C 0.3747(5) 0.6125(4) 0.6548(3) 0.0167(8) Uani 1 1 d . . . . .
H10 H 0.359850 0.643644 0.592200 0.020 Uiso 1 1 calc R . . . .
C8 C 0.6754(5) 0.5637(4) 0.6153(3) 0.0167(8) Uani 1 1 d . . . . .
C2 C 0.8165(5) 1.0065(4) 0.4345(3) 0.0249(9) Uani 1 1 d . . . . .
H2 H 0.799104 1.067193 0.491073 0.030 Uiso 1 1 calc R . . . .
C6 C 0.7571(5) 0.7855(4) 0.3341(3) 0.0223(9) Uani 1 1 d . . . . .
H6 H 0.699082 0.698412 0.323576 0.027 Uiso 1 1 calc R . . . .
C1 C 0.7355(5) 0.8743(4) 0.4205(3) 0.0205(9) Uani 1 1 d . . . . .
C15 C 0.1440(5) 0.7982(4) 0.9920(3) 0.0159(8) Uani 1 1 d . . . . .
C13 C 0.4172(5) 0.5236(4) 0.8417(3) 0.0182(9) Uani 1 1 d . . . . .
H13 H 0.432457 0.494933 0.904983 0.022 Uiso 1 1 calc R . . . .
C14 C 0.5524(5) 0.5243(4) 0.7795(3) 0.0199(9) Uani 1 1 d . . . . .
H14 H 0.657893 0.495224 0.801467 0.024 Uiso 1 1 calc R . . . .
C19 C 0.3118(5) 0.8360(4) 1.1434(3) 0.0252(10) Uani 1 1 d . . . . .
H19 H 0.355030 0.802670 1.201203 0.030 Uiso 1 1 calc R . . . .
C20 C 0.2043(5) 0.7489(4) 1.0793(3) 0.0238(9) Uani 1 1 d . . . . .
H20 H 0.173008 0.658796 1.094570 0.029 Uiso 1 1 calc R . . . .
C18 C 0.3563(5) 0.9726(4) 1.1229(3) 0.0211(9) Uani 1 1 d . . . . .
C16 C 0.1902(5) 0.9323(4) 0.9693(3) 0.0198(9) Uani 1 1 d . . . . .
H16 H 0.150909 0.964397 0.910212 0.024 Uiso 1 1 calc R . . . .
C3 C 0.9231(5) 1.0467(4) 0.3636(3) 0.0278(10) Uani 1 1 d . . . . .
H3 H 0.978118 1.135122 0.372865 0.033 Uiso 1 1 calc R . . . .
C12 C 0.2595(5) 0.5656(4) 0.8097(3) 0.0159(8) Uani 1 1 d . . . . .
C5 C 0.8659(5) 0.8280(4) 0.2637(3) 0.0295(10) Uani 1 1 d . . . . .
H5 H 0.882568 0.768867 0.206226 0.035 Uiso 1 1 calc R . . . .
C17 C 0.2950(5) 1.0181(4) 1.0352(3) 0.0226(9) Uani 1 1 d . . . . .
H17 H 0.325021 1.108606 1.020023 0.027 Uiso 1 1 calc R . . . .
C21 C 0.4636(6) 1.0701(4) 1.1967(3) 0.0319(11) Uani 1 1 d . . . . .
H21A H 0.394471 1.107285 1.249391 0.048 Uiso 1 1 calc GR . . . .
H21B H 0.510000 1.146678 1.164041 0.048 Uiso 1 1 calc GR . . . .
H21C H 0.554445 1.018298 1.223598 0.048 Uiso 1 1 calc GR . . . .
C4 C 0.9493(5) 0.9587(5) 0.2796(3) 0.0338(11) Uani 1 1 d . . . . .
H4 H 1.023480 0.986931 0.233041 0.041 Uiso 1 1 calc R . . . .
H1 H 0.133(5) 0.512(4) 0.908(3) 0.003(11) 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
I1 C8 2.122(4) . ?
Se02 C7 1.901(4) . ?
Se02 C1 1.920(4) . ?
S1 O1 1.426(3) . ?
S1 O2 1.444(2) . ?
S1 N1 1.636(3) . ?
S1 C15 1.763(4) . ?
N1 C12 1.429(5) . ?
C9 C10 1.387(5) . ?
C9 C8 1.485(5) . ?
C9 C14 1.399(5) . ?
C7 C8 1.339(5) . ?
C11 C10 1.387(5) . ?
C11 C12 1.394(5) . ?
C2 C1 1.386(5) . ?
C2 C3 1.376(5) . ?
C6 C1 1.392(5) . ?
C6 C5 1.390(5) . ?
C15 C20 1.387(5) . ?
C15 C16 1.382(5) . ?
C13 C14 1.385(5) . ?
C13 C12 1.382(5) . ?
C19 C20 1.386(5) . ?
C19 C18 1.392(5) . ?
C18 C17 1.379(5) . ?
C18 C21 1.511(5) . ?
C16 C17 1.381(5) . ?
C3 C4 1.370(6) . ?
C5 C4 1.383(6) . ?

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
C7 Se02 C1 96.90(16) . . ?
O1 S1 O2 119.06(16) . . ?
O1 S1 N1 108.19(17) . . ?
O1 S1 C15 109.19(16) . . ?
O2 S1 N1 104.75(16) . . ?
O2 S1 C15 108.05(15) . . ?
N1 S1 C15 106.95(18) . . ?
C12 N1 S1 122.3(3) . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 C14 117.7(3) . . ?
C14 C9 C8 121.7(3) . . ?
C8 C7 Se02 127.3(3) . . ?
C10 C11 C12 119.1(4) . . ?
C11 C10 C9 122.0(3) . . ?
C9 C8 I1 115.5(3) . . ?
C7 C8 I1 116.2(3) . . ?
C7 C8 C9 128.3(4) . . ?
C3 C2 C1 119.2(4) . . ?
C5 C6 C1 119.5(4) . . ?
C2 C1 Se02 119.5(3) . . ?
C2 C1 C6 120.3(4) . . ?
C6 C1 Se02 120.1(3) . . ?
C20 C15 S1 118.9(3) . . ?
C16 C15 S1 120.6(3) . . ?
C16 C15 C20 120.5(3) . . ?
C12 C13 C14 120.0(3) . . ?
C13 C14 C9 121.2(4) . . ?
C20 C19 C18 121.2(4) . . ?
C19 C20 C15 119.0(3) . . ?
C19 C18 C21 120.7(4) . . ?
C17 C18 C19 118.3(3) . . ?
C17 C18 C21 120.9(3) . . ?
C17 C16 C15 119.5(4) . . ?
C4 C3 C2 121.1(4) . . ?
C11 C12 N1 119.6(3) . . ?
C13 C12 N1 120.2(3) . . ?
C13 C12 C11 120.0(3) . . ?
C4 C5 C6 119.7(4) . . ?
C18 C17 C16 121.4(3) . . ?
C3 C4 C5 120.2(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.744
