# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ktr-3i
_database_code_depnum_ccdc_archive 'CCDC 1899449'
loop_
_audit_author_name
_audit_author_address
'Jing Li'
;China West Normal University
China
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Br N2'
_chemical_formula_sum            'C15 H11 Br N2'
_chemical_formula_weight         299.17
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.5406(3)
_cell_length_b                   8.3315(5)
_cell_length_c                   27.8631(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1286.21(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2560
_cell_measurement_temperature    292.95(10)
_cell_measurement_theta_max      71.3670
_cell_measurement_theta_min      4.7620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            7593
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.852
_diffrn_reflns_theta_min         5.542
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    1.00    --  -35.92 -38.00 150.00   88
  2  ω    -55.00  33.00   1.00    1.00    --  -35.92  38.00 -90.00   88
  3  ω    -33.00 105.00   1.00    1.00    --   35.92   0.00 150.00  138
  4  ω     25.00  91.00   1.00    1.00    --   35.92-127.00 -14.00   66
  5  ω    -31.00  53.00   1.00    1.00    --   35.92 -57.00  30.00   84
  6  ω     39.00 115.00   1.00    1.00    --  108.71-111.00  30.00   76
  7  ω    100.00 178.00   1.00    1.00    --  108.71 111.00 150.00   78
  8  ω     87.00 178.00   1.00    1.00    --  108.71  30.00-120.00   91
  9  ω    100.00 178.00   1.00    1.00    --  108.71 111.00 -30.00   78
 10  ω     39.00 130.00   1.00    1.00    --  108.71 -30.00-120.00   91
 11  ω    100.00 178.00   1.00    1.00    --  108.71 111.00-120.00   78
 12  ω     39.00 109.00   1.00    1.00    --  108.71 -94.00-180.00   70
 13  ω     39.00 109.00   1.00    1.00    --  108.71 -94.00 150.00   70
 14  ω     39.00 109.00   1.00    1.00    --  108.71 -94.00  60.00   70
 15  ω   -103.00 -19.00   1.00    1.00    --  -35.92 -57.00 -60.00   84
 16  ω    -31.00  51.00   1.00    1.00    --   35.92 -57.00 120.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0301740000
_diffrn_orient_matrix_UB_12      -0.0699766000
_diffrn_orient_matrix_UB_13      -0.0508318000
_diffrn_orient_matrix_UB_21      -0.0382502000
_diffrn_orient_matrix_UB_22      0.1682479000
_diffrn_orient_matrix_UB_23      -0.0216297000
_diffrn_orient_matrix_UB_31      0.2737620000
_diffrn_orient_matrix_UB_32      0.0311128000
_diffrn_orient_matrix_UB_33      0.0025870000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                1958
_reflns_number_total             2447
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.175
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 
;
 Flack x determined using 528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0804
_refine_ls_restrained_S_all      1.083
_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)+(0.1739P)²+0.1783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2372
_refine_ls_wR_factor_ref         0.2596
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7AA(H7AA), C8(H8), C4AA(H4AA), C2AA(H2AA), C6AA(H6AA), C1(H1), C2(H2),
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 0.4864(3) 0.88493(16) 0.23855(4) 0.0967(6) Uani 1 1 d . . . . .
N0AA N 0.4823(11) 0.5200(8) -0.0032(2) 0.0531(14) Uani 1 1 d . . . . .
C5AA C 0.4528(15) 0.5945(9) 0.0702(3) 0.0562(18) Uani 1 1 d . . . . .
C7AA C 0.6933(14) 0.5958(11) 0.0069(3) 0.062(2) Uani 1 1 d . . . . .
H7AA H 0.8209 0.6138 -0.0141 0.074 Uiso 1 1 calc R . . . .
C8 C 0.6813(14) 0.6406(12) 0.0540(3) 0.059(2) Uani 1 1 d . . . . .
H8 H 0.8011 0.6915 0.0718 0.070 Uiso 1 1 calc R . . . .
N10 N 0.3340(12) 0.5176(9) 0.0349(2) 0.0572(16) Uani 1 1 d . . . . .
C3AA C 0.3471(13) 0.6124(10) 0.1175(3) 0.0547(17) Uani 1 1 d . . . . .
C4AA C 0.5332(19) 0.4920(13) -0.0893(3) 0.071(2) Uani 1 1 d . . . . .
H4AA H 0.6719 0.5547 -0.0882 0.086 Uiso 1 1 calc R . . . .
C2AA C 0.449(2) 0.4323(13) -0.1333(3) 0.079(3) Uani 1 1 d . . . . .
H2AA H 0.5348 0.4537 -0.1613 0.095 Uiso 1 1 calc R . . . .
C6AA C 0.4469(16) 0.7212(9) 0.1503(3) 0.0595(18) Uani 1 1 d . . . . .
H6AA H 0.5835 0.7803 0.1423 0.071 Uiso 1 1 calc R . . . .
C1AA C 0.4081(15) 0.4570(9) -0.0477(3) 0.0556(17) Uani 1 1 d . . . . .
C1 C 0.0378(18) 0.5508(14) 0.1752(4) 0.077(3) Uani 1 1 d . . . . .
H1 H -0.1008 0.4943 0.1835 0.092 Uiso 1 1 calc R . . . .
C2 C 0.2033(18) 0.3625(11) -0.0498(4) 0.066(2) Uani 1 1 d . . . . .
H2 H 0.1189 0.3372 -0.0220 0.079 Uiso 1 1 calc R . . . .
C3 C 0.124(2) 0.3052(12) -0.0945(4) 0.077(3) Uani 1 1 d . . . . .
H3 H -0.0120 0.2403 -0.0958 0.093 Uiso 1 1 calc R . . . .
C4 C 0.240(2) 0.3419(12) -0.1354(4) 0.081(3) Uani 1 1 d . . . . .
H4 H 0.1809 0.3067 -0.1648 0.097 Uiso 1 1 calc R . . . .
C5 C 0.1418(16) 0.5266(12) 0.1308(3) 0.065(2) Uani 1 1 d . . . . .
H5 H 0.0747 0.4527 0.1097 0.079 Uiso 1 1 calc R . . . .
C6 C 0.1379(16) 0.6584(14) 0.2076(3) 0.072(2) Uani 1 1 d . . . . .
H6 H 0.0690 0.6752 0.2376 0.087 Uiso 1 1 calc R . . . .
C7 C 0.3411(19) 0.7389(12) 0.1938(3) 0.069(2) 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
Br1 C7 1.919(10) . ?
N0AA C7AA 1.358(10) . ?
N0AA N10 1.343(9) . ?
N0AA C1AA 1.407(10) . ?
C5AA C8 1.398(11) . ?
C5AA N10 1.346(11) . ?
C5AA C3AA 1.451(12) . ?
C7AA C8 1.366(13) . ?
C3AA C6AA 1.399(12) . ?
C3AA C5 1.394(12) . ?
C4AA C2AA 1.402(14) . ?
C4AA C1AA 1.382(12) . ?
C2AA C4 1.382(15) . ?
C6AA C7 1.356(12) . ?
C1AA C2 1.383(13) . ?
C1 C5 1.380(13) . ?
C1 C6 1.388(15) . ?
C2 C3 1.402(15) . ?
C3 C4 1.345(15) . ?
C6 C7 1.366(14) . ?

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
C7AA N0AA C1AA 127.4(7) . . ?
N10 N0AA C7AA 111.7(7) . . ?
N10 N0AA C1AA 120.8(6) . . ?
C8 C5AA C3AA 129.0(8) . . ?
N10 C5AA C8 109.8(8) . . ?
N10 C5AA C3AA 121.1(7) . . ?
N0AA C7AA C8 106.6(7) . . ?
C7AA C8 C5AA 106.2(8) . . ?
N0AA N10 C5AA 105.7(6) . . ?
C6AA C3AA C5AA 120.0(7) . . ?
C5 C3AA C5AA 121.2(8) . . ?
C5 C3AA C6AA 118.8(8) . . ?
C1AA C4AA C2AA 119.5(9) . . ?
C4 C2AA C4AA 120.5(9) . . ?
C7 C6AA C3AA 118.9(8) . . ?
C4AA C1AA N0AA 120.9(8) . . ?
C4AA C1AA C2 119.7(9) . . ?
C2 C1AA N0AA 119.3(8) . . ?
C5 C1 C6 120.7(9) . . ?
C1AA C2 C3 119.2(9) . . ?
C4 C3 C2 121.7(10) . . ?
C3 C4 C2AA 119.2(9) . . ?
C1 C5 C3AA 120.3(9) . . ?
C7 C6 C1 117.6(9) . . ?
C6AA C7 Br1 118.0(8) . . ?
C6AA C7 C6 123.7(9) . . ?
C6 C7 Br1 118.3(7) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-15
_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 5.387
_oxdiff_exptl_absorpt_empirical_full_min 0.445
####################################################################### 
# 
# 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_cd-lj-4b
_database_code_depnum_ccdc_archive 'CCDC 1910849'
loop_
_audit_author_name
_audit_author_address
'Jing Li'
;China West Normal University
China
;
_audit_update_record             
;
2019-04-17 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_audit_creation_date             2018-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O2 S'
_chemical_formula_sum            'C16 H18 O2 S'
_chemical_formula_weight         274.36
_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 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.1266(3)
_cell_length_b                   24.3656(8)
_cell_length_c                   7.7718(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.298(4)
_cell_angle_gamma                90
_cell_volume                     1443.33(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    295.13(10)
_cell_measurement_theta_max      72.4290
_cell_measurement_theta_min      6.0950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8456
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.863
_diffrn_reflns_theta_min         3.628
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.13(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.20    --  -36.29  57.00 -30.00   84
  2  ω   -105.00 -17.00   1.00    1.20    --  -36.29 -38.00 -60.00   88
  3  ω     20.00 104.00   1.00    1.20    --   36.29  57.00 -90.00   84
  4  ω    -31.00  53.00   1.00    1.20    --   36.29 -57.00  90.00   84
  5  ω     23.00  90.00   1.00    1.20    --   36.29-125.00-180.00   67
  6  ω     39.00 115.00   1.00    4.81    --  108.71-111.00-180.00   76
  7  ω     91.00 176.00   1.00    4.81    --  108.71  61.00  60.00   85
  8  ω     91.00 176.00   1.00    4.81    --  108.71  61.00 -60.00   85
  9  ω     39.00 109.00   1.00    4.81    --  108.71 -94.00  60.00   70
 10  ω    100.00 178.00   1.00    4.81    --  108.71 111.00-120.00   78
 11  ω     39.00 130.00   1.00    4.81    --  108.71 -30.00 -60.00   91
 12  ω     42.00 127.00   1.00    4.81    --  108.71 -61.00 150.00   85
 13  ω   -105.00 -17.00   1.00    1.20    --  -36.29 -38.00  30.00   88
 14  ω    -53.00  31.00   1.00    1.20    --  -36.29  57.00  60.00   84
 15  ω     20.00 104.00   1.00    1.20    --   36.29  57.00-180.00   84
 16  ω     91.00 165.00   1.00    4.81    --  108.71  45.00 120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0622227000
_diffrn_orient_matrix_UB_12      -0.0600352000
_diffrn_orient_matrix_UB_13      0.0086791000
_diffrn_orient_matrix_UB_21      0.1921031000
_diffrn_orient_matrix_UB_22      0.0195665000
_diffrn_orient_matrix_UB_23      0.0669866000
_diffrn_orient_matrix_UB_31      0.0071242000
_diffrn_orient_matrix_UB_32      -0.0039553000
_diffrn_orient_matrix_UB_33      0.2002460000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2337
_reflns_number_total             2802
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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         0.393
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.048
_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)+(0.1100P)²+0.1447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1680
_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:
 C12(H12), C5(H5), C10(H10), C4(H4), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S1 S 0.70227(7) 0.37895(2) 0.03173(7) 0.0549(2) Uani 1 1 d . . . . .
O1 O 0.5900(3) 0.41092(8) -0.1185(2) 0.0747(5) Uani 1 1 d . . . . .
O2 O 0.8717(3) 0.36458(8) 0.0261(3) 0.0767(6) Uani 1 1 d . . . . .
C13 C 0.6693(3) 0.26647(9) 0.0773(3) 0.0485(5) Uani 1 1 d . . . . .
C12 C 0.5662(3) 0.22074(9) 0.0738(3) 0.0540(5) Uani 1 1 d . . . . .
H12 H 0.6184 0.1862 0.0901 0.065 Uiso 1 1 calc R . . . .
C6 C 0.7359(3) 0.41602(8) 0.2374(3) 0.0505(5) Uani 1 1 d . . . . .
C9 C 0.4101(3) 0.32348(9) 0.0349(3) 0.0508(5) Uani 1 1 d . . . . .
C11 C 0.3899(3) 0.22435(9) 0.0471(3) 0.0551(5) Uani 1 1 d . . . . .
C8 C 0.5875(3) 0.31812(8) 0.0522(3) 0.0457(4) Uani 1 1 d . . . . .
C5 C 0.8188(4) 0.39118(10) 0.4037(3) 0.0628(6) Uani 1 1 d . . . . .
H5 H 0.8540 0.3547 0.4087 0.075 Uiso 1 1 calc R . . . .
C3 C 0.7991(3) 0.47448(10) 0.5601(4) 0.0637(6) Uani 1 1 d . . . . .
C10 C 0.3163(3) 0.27601(10) 0.0332(3) 0.0555(5) Uani 1 1 d . . . . .
H10 H 0.1990 0.2790 0.0222 0.067 Uiso 1 1 calc R . . . .
C4 C 0.8496(4) 0.42078(12) 0.5636(4) 0.0711(7) Uani 1 1 d . . . . .
H4 H 0.9059 0.4038 0.6760 0.085 Uiso 1 1 calc R . . . .
C1 C 0.6836(4) 0.46975(10) 0.2297(4) 0.0764(8) Uani 1 1 d . . . . .
H1 H 0.6272 0.4867 0.1174 0.092 Uiso 1 1 calc R . . . .
C15 C 0.2807(4) 0.17349(12) 0.0342(4) 0.0774(8) Uani 1 1 d . . . . .
H15A H 0.2214 0.1643 -0.0924 0.116 Uiso 1 1 calc GR . . . .
H15B H 0.1957 0.1801 0.0922 0.116 Uiso 1 1 calc GR . . . .
H15C H 0.3553 0.1436 0.0948 0.116 Uiso 1 1 calc GR . . . .
C14 C 0.3143(3) 0.37752(11) 0.0208(4) 0.0707(7) Uani 1 1 d . . . . .
H14A H 0.3776 0.4006 0.1225 0.106 Uiso 1 1 calc GR . . . .
H14B H 0.1986 0.3708 0.0230 0.106 Uiso 1 1 calc GR . . . .
H14C H 0.3059 0.3954 -0.0919 0.106 Uiso 1 1 calc GR . . . .
C16 C 0.8601(3) 0.25543(12) 0.1086(4) 0.0674(7) Uani 1 1 d . . . . .
H16A H 0.8873 0.2180 0.1466 0.101 Uiso 1 1 calc GR . . . .
H16B H 0.9319 0.2796 0.2023 0.101 Uiso 1 1 calc GR . . . .
H16C H 0.8826 0.2617 -0.0032 0.101 Uiso 1 1 calc GR . . . .
C2 C 0.7163(4) 0.49815(11) 0.3920(5) 0.0826(9) Uani 1 1 d . . . . .
H2 H 0.6810 0.5346 0.3872 0.099 Uiso 1 1 calc R . . . .
C7 C 0.8339(5) 0.50592(14) 0.7361(5) 0.0948(11) Uani 1 1 d . . . . .
H7A H 0.7378 0.5008 0.7795 0.142 Uiso 1 1 calc GR . . . .
H7B H 0.8458 0.5442 0.7143 0.142 Uiso 1 1 calc GR . . . .
H7C H 0.9401 0.4928 0.8266 0.142 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
S1 O1 1.4363(18) . ?
S1 O2 1.436(2) . ?
S1 C6 1.773(2) . ?
S1 C8 1.787(2) . ?
C13 C12 1.389(3) . ?
C13 C8 1.405(3) . ?
C13 C16 1.508(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.378(3) . ?
C6 C5 1.373(3) . ?
C6 C1 1.371(3) . ?
C9 C8 1.407(3) . ?
C9 C10 1.383(3) . ?
C9 C14 1.514(3) . ?
C11 C10 1.382(3) . ?
C11 C15 1.507(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(4) . ?
C3 C4 1.369(4) . ?
C3 C2 1.372(4) . ?
C3 C7 1.506(4) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.381(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 H2 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
O1 S1 C6 108.19(12) . . ?
O1 S1 C8 108.54(10) . . ?
O2 S1 O1 116.93(13) . . ?
O2 S1 C6 107.60(11) . . ?
O2 S1 C8 109.64(11) . . ?
C6 S1 C8 105.32(9) . . ?
C12 C13 C8 117.59(19) . . ?
C12 C13 C16 116.1(2) . . ?
C8 C13 C16 126.3(2) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 C13 122.7(2) . . ?
C11 C12 H12 118.6 . . ?
C5 C6 S1 119.72(18) . . ?
C1 C6 S1 119.90(19) . . ?
C1 C6 C5 120.4(2) . . ?
C8 C9 C14 124.9(2) . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 C14 117.3(2) . . ?
C12 C11 C10 118.0(2) . . ?
C12 C11 C15 121.0(2) . . ?
C10 C11 C15 121.0(2) . . ?
C13 C8 S1 121.26(15) . . ?
C13 C8 C9 121.08(19) . . ?
C9 C8 S1 117.61(16) . . ?
C6 C5 H5 120.2 . . ?
C6 C5 C4 119.5(2) . . ?
C4 C5 H5 120.2 . . ?
C4 C3 C2 117.7(2) . . ?
C4 C3 C7 120.5(3) . . ?
C2 C3 C7 121.8(3) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.6(2) . . ?
C11 C10 H10 118.7 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C6 C1 H1 120.7 . . ?
C6 C1 C2 118.7(2) . . ?
C2 C1 H1 120.7 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C2 C1 122.3(2) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_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 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.718
