# 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_2pq-1
_database_code_depnum_ccdc_archive 'CCDC 1867094'
loop_
_audit_author_name
_audit_author_address
'Frank Allene'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2018-09-11 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2018-05-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H8 Br N S2'
_chemical_formula_sum            'C15 H8 Br N S2'
_chemical_formula_weight         346.25
_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'
Br Br -0.2901 2.4595 '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'
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                   6.8836(3)
_cell_length_b                   7.0346(3)
_cell_length_c                   13.5790(5)
_cell_angle_alpha                88.344(3)
_cell_angle_beta                 89.963(3)
_cell_angle_gamma                79.153(4)
_cell_volume                     645.52(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6044
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3270
_cell_measurement_theta_min      2.9210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.489
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36968
_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    1.781
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9909
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.950
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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    -85.00  17.00   1.00    1.00    --  -11.59 -57.00 -60.00  102
  2  ω    -40.00  62.00   1.00    1.00    --  -11.59  57.00  90.00  102
  3  ω    -21.00  88.00   1.00    1.00    --   11.74  77.00-150.00  109
  4  ω     34.00  99.00   1.00    1.00    --   11.74-178.00  90.00   65
  5  ω    -20.00   5.00   1.00    1.00    --   11.74 -99.00-150.00   25
  6  ω    -63.00  36.00   1.00    1.00    --   11.74 -37.00-120.00   99
  7  ω    -85.00 -60.00   1.00    1.00    --  -11.59 151.00 -82.45   25
  8  ω    -88.00 -18.00   1.00    1.00    --  -11.59 -77.00 150.00   70
  9  ω    -85.00 -39.00   1.00    1.00    --  -11.59 151.00 133.38   46
 10  ω     23.00  52.00   1.00    1.00    --   11.74  37.00  90.00   29
;
_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      0.0076339000
_diffrn_orient_matrix_UB_12      -0.0015222000
_diffrn_orient_matrix_UB_13      -0.0520763000
_diffrn_orient_matrix_UB_21      -0.1022269000
_diffrn_orient_matrix_UB_22      0.0403657000
_diffrn_orient_matrix_UB_23      -0.0042970000
_diffrn_orient_matrix_UB_31      0.0223396000
_diffrn_orient_matrix_UB_32      0.0944316000
_diffrn_orient_matrix_UB_33      -0.0006682000
_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                2140
_reflns_number_total             2276
_reflns_odcompleteness_completeness 99.96
_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         0.490
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.086
_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)+(0.0325P)²+0.1415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0657
_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:
 C5(H5), C12(H12), C6(H6), C2(H2), C15(H15), C3(H3), C13(H13), C14(H14)
;
_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
Br1 Br 0.02001(4) 0.87527(3) 0.12888(2) 0.01826(11) Uani 1 1 d . . . . .
S1 S 0.78851(9) 0.66494(9) 0.49784(5) 0.01390(16) Uani 1 1 d . . . . .
S2 S 0.97755(9) 0.61457(9) 0.71236(5) 0.01478(16) Uani 1 1 d . . . . .
N1 N 0.4572(3) 0.7646(3) 0.59169(15) 0.0125(4) Uani 1 1 d . . . . .
C7 C 0.5291(3) 0.7422(3) 0.50315(18) 0.0120(5) Uani 1 1 d . . . . .
C1 C 0.4122(4) 0.7773(3) 0.41239(18) 0.0124(5) Uani 1 1 d . . . . .
C5 C 0.0929(4) 0.8802(3) 0.33442(18) 0.0143(5) Uani 1 1 d . . . . .
H5 H -0.042164 0.928340 0.338968 0.017 Uiso 1 1 calc R . . . .
C9 C 0.6073(3) 0.7199(3) 0.66031(19) 0.0119(5) Uani 1 1 d . . . . .
C12 C 0.8326(4) 0.6563(4) 0.90506(19) 0.0176(6) Uani 1 1 d . . . . .
H12 H 0.960805 0.621155 0.929658 0.021 Uiso 1 1 calc R . . . .
C10 C 0.6037(4) 0.7212(3) 0.76594(19) 0.0136(5) Uani 1 1 d . . . . .
C11 C 0.7962(4) 0.6663(3) 0.80500(19) 0.0134(5) Uani 1 1 d . . . . .
C4 C 0.1801(4) 0.8401(3) 0.24337(18) 0.0133(5) Uani 1 1 d . . . . .
C6 C 0.2097(3) 0.8476(3) 0.41841(18) 0.0131(5) Uani 1 1 d . . . . .
H6 H 0.151963 0.873034 0.479751 0.016 Uiso 1 1 calc R . . . .
C2 C 0.4965(4) 0.7405(4) 0.31971(19) 0.0172(6) Uani 1 1 d . . . . .
H2 H 0.631817 0.694767 0.314586 0.021 Uiso 1 1 calc R . . . .
C8 C 0.7937(3) 0.6649(3) 0.62364(19) 0.0131(5) Uani 1 1 d . . . . .
C15 C 0.4456(4) 0.7658(4) 0.83056(19) 0.0184(6) Uani 1 1 d . . . . .
H15 H 0.317294 0.802931 0.806324 0.022 Uiso 1 1 calc R . . . .
C3 C 0.3814(4) 0.7712(4) 0.23582(19) 0.0180(6) Uani 1 1 d . . . . .
H3 H 0.438582 0.745688 0.174375 0.022 Uiso 1 1 calc R . . . .
C13 C 0.6733(4) 0.6998(4) 0.9677(2) 0.0220(6) Uani 1 1 d . . . . .
H13 H 0.694223 0.692753 1.035475 0.026 Uiso 1 1 calc R . . . .
C14 C 0.4804(4) 0.7546(4) 0.9303(2) 0.0231(6) Uani 1 1 d . . . . .
H14 H 0.374841 0.783630 0.973574 0.028 Uiso 1 1 calc R . . . .


_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 C4 1.889(2) . ?
S1 C7 1.768(2) . ?
S1 C8 1.709(3) . ?
S2 C11 1.768(3) . ?
S2 C8 1.728(2) . ?
N1 C7 1.302(3) . ?
N1 C9 1.377(3) . ?
C7 C1 1.462(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.396(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(4) . ?
C5 C6 1.384(4) . ?
C9 C10 1.435(4) . ?
C9 C8 1.367(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.379(4) . ?
C12 C13 1.381(4) . ?
C10 C11 1.408(3) . ?
C10 C15 1.393(3) . ?
C4 C3 1.384(4) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.373(4) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.402(4) . ?
C14 H14 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
C8 S1 C7 88.34(12) . . ?
C8 S2 C11 89.56(12) . . ?
C7 N1 C9 110.0(2) . . ?
N1 C7 S1 114.94(18) . . ?
N1 C7 C1 124.9(2) . . ?
C1 C7 S1 120.19(18) . . ?
C6 C1 C7 119.0(2) . . ?
C6 C1 C2 118.8(2) . . ?
C2 C1 C7 122.2(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.0(2) . . ?
N1 C9 C10 131.1(2) . . ?
C8 C9 N1 116.1(2) . . ?
C8 C9 C10 112.8(2) . . ?
C11 C12 H12 120.9 . . ?
C11 C12 C13 118.1(2) . . ?
C13 C12 H12 120.9 . . ?
C11 C10 C9 110.7(2) . . ?
C15 C10 C9 130.5(2) . . ?
C15 C10 C11 118.8(2) . . ?
C12 C11 S2 125.47(19) . . ?
C12 C11 C10 122.0(2) . . ?
C10 C11 S2 112.53(19) . . ?
C5 C4 Br1 119.26(19) . . ?
C3 C4 Br1 119.88(19) . . ?
C3 C4 C5 120.8(2) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
S1 C8 S2 134.92(15) . . ?
C9 C8 S1 110.68(18) . . ?
C9 C8 S2 114.40(19) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.5(2) . . ?
C14 C15 H15 120.2 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?

_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 2.106
_oxdiff_exptl_absorpt_empirical_full_min 0.615
####################################################################### 
# 
# 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_3s
_database_code_depnum_ccdc_archive 'CCDC 1867096'
loop_
_audit_author_name
_audit_author_address
'Frank Allene'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2018-09-11 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2018-06-19
_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         'C16 H8 F3 N S3'
_chemical_formula_sum            'C16 H8 F3 N S3'
_chemical_formula_weight         367.41
_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'
F F 0.0171 0.0103 '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'
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                   4.2674(3)
_cell_length_b                   12.9135(8)
_cell_length_c                   13.4730(8)
_cell_angle_alpha                77.893(5)
_cell_angle_beta                 87.653(5)
_cell_angle_gamma                86.789(5)
_cell_volume                     724.48(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0520
_cell_measurement_theta_min      2.4690
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91018
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6627
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.990
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  40.00   1.00    1.00    --   11.74 -57.00 -90.00  100
  2  ω    -21.00  88.00   1.00    1.00    --   11.74  77.00-180.00  109
  3  ω    -16.00  85.00   1.00    1.00    --   11.74  57.00  60.00  101
  4  ω    -62.00 -15.00   1.00    1.00    --  -11.59 115.00 161.00   47
  5  ω    -16.00  27.00   1.00    1.00    --   11.74  57.00 -60.00   43
;
_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      0.0431084000
_diffrn_orient_matrix_UB_12      0.0406810000
_diffrn_orient_matrix_UB_13      0.0241493000
_diffrn_orient_matrix_UB_21      -0.0023403000
_diffrn_orient_matrix_UB_22      0.0365255000
_diffrn_orient_matrix_UB_23      -0.0473346000
_diffrn_orient_matrix_UB_31      -0.1608564000
_diffrn_orient_matrix_UB_32      0.0131972000
_diffrn_orient_matrix_UB_33      0.0088294000
_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                2237
_reflns_number_total             2536
_reflns_odcompleteness_completeness 99.93
_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         0.448
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.055
_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)+(0.0361P)²+0.4797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0855
_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:
 C5(H5), C2(H2), C11(H11), C15(H15), C14(H14), C3(H3), C13(H13), C12(H12)
;
_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
S1 S 0.42135(13) 0.51844(5) 0.87379(4) 0.01985(16) Uani 1 1 d . . . . .
S3 S 0.72744(13) 0.58817(4) 0.55179(4) 0.01788(16) Uani 1 1 d . . . . .
S2 S 0.31666(13) 0.48773(5) 0.73534(4) 0.02067(16) Uani 1 1 d . . . . .
F1 F -0.3768(4) 0.90316(13) 0.98526(12) 0.0388(4) Uani 1 1 d . . . . .
F3 F -0.3301(4) 0.74695(12) 1.07334(12) 0.0453(5) Uani 1 1 d . . . . .
F2 F 0.0198(3) 0.85936(17) 1.07591(13) 0.0552(6) Uani 1 1 d . . . . .
N007 N 0.6827(4) 0.76466(15) 0.61259(13) 0.0161(4) Uani 1 1 d . . . . .
C10 C 1.0035(5) 0.77629(18) 0.45546(16) 0.0158(5) Uani 1 1 d . . . . .
C1 C 0.3412(5) 0.72559(17) 0.76750(17) 0.0154(5) Uani 1 1 d . . . . .
C8 C 0.5132(5) 0.69323(18) 0.68192(16) 0.0158(5) Uani 1 1 d . . . . .
C5 C 0.0995(5) 0.68341(18) 0.93655(17) 0.0179(5) Uani 1 1 d . . . . .
H5 H 0.049261 0.633780 0.994890 0.021 Uiso 1 1 calc R . . . .
C6 C 0.2701(5) 0.65142(18) 0.85719(16) 0.0161(5) Uani 1 1 d . . . . .
C9 C 0.8081(5) 0.72137(17) 0.54008(16) 0.0157(5) Uani 1 1 d . . . . .
C7 C 0.5117(5) 0.59429(18) 0.66094(16) 0.0163(5) Uani 1 1 d . . . . .
C2 C 0.2351(5) 0.83049(18) 0.76107(17) 0.0180(5) Uani 1 1 d . . . . .
H2 H 0.275588 0.880219 0.701854 0.022 Uiso 1 1 calc R . . . .
C4 C 0.0044(5) 0.78874(19) 0.92902(17) 0.0181(5) Uani 1 1 d . . . . .
C11 C 1.0817(5) 0.87959(19) 0.45361(18) 0.0220(5) Uani 1 1 d . . . . .
H11 H 1.011219 0.912371 0.506148 0.026 Uiso 1 1 calc R . . . .
C15 C 1.1149(5) 0.72814(19) 0.37696(17) 0.0217(5) Uani 1 1 d . . . . .
H15 H 1.066477 0.658712 0.377403 0.026 Uiso 1 1 calc R . . . .
C14 C 1.2975(6) 0.7830(2) 0.29819(18) 0.0248(6) Uani 1 1 d . . . . .
H14 H 1.371687 0.750142 0.246059 0.030 Uiso 1 1 calc R . . . .
C3 C 0.0704(5) 0.86240(19) 0.84102(17) 0.0193(5) Uani 1 1 d . . . . .
H3 H 0.004210 0.933154 0.835680 0.023 Uiso 1 1 calc R . . . .
C16 C -0.1677(5) 0.8236(2) 1.01581(18) 0.0232(5) Uani 1 1 d . . . . .
C13 C 1.3700(5) 0.8860(2) 0.29654(18) 0.0249(6) Uani 1 1 d . . . . .
H13 H 1.490628 0.922931 0.243015 0.030 Uiso 1 1 calc R . . . .
C12 C 1.2631(6) 0.9343(2) 0.37463(18) 0.0249(6) Uani 1 1 d . . . . .
H12 H 1.313153 1.003555 0.374048 0.030 Uiso 1 1 calc R . . . .


_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 S2 2.0578(8) . ?
S1 C6 1.773(2) . ?
S3 C9 1.746(2) . ?
S3 C7 1.717(2) . ?
S2 C7 1.753(2) . ?
F1 C16 1.331(3) . ?
F3 C16 1.331(3) . ?
F2 C16 1.327(3) . ?
N007 C8 1.380(3) . ?
N007 C9 1.306(3) . ?
C10 C9 1.466(3) . ?
C10 C11 1.388(3) . ?
C10 C15 1.390(3) . ?
C1 C8 1.463(3) . ?
C1 C6 1.410(3) . ?
C1 C2 1.390(3) . ?
C8 C7 1.366(3) . ?
C5 C6 1.390(3) . ?
C5 C4 1.381(3) . ?
C2 C3 1.384(3) . ?
C4 C3 1.385(3) . ?
C4 C16 1.491(3) . ?
C11 C12 1.381(3) . ?
C15 C14 1.383(3) . ?
C14 C13 1.379(3) . ?
C13 C12 1.381(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
C6 S1 S2 99.53(8) . . ?
C7 S3 C9 88.96(10) . . ?
C7 S2 S1 96.35(8) . . ?
C9 N007 C8 111.48(19) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 C15 118.7(2) . . ?
C15 C10 C9 122.2(2) . . ?
C6 C1 C8 121.3(2) . . ?
C2 C1 C8 120.5(2) . . ?
C2 C1 C6 118.1(2) . . ?
N007 C8 C1 121.0(2) . . ?
C7 C8 N007 114.57(19) . . ?
C7 C8 C1 124.37(19) . . ?
C4 C5 C6 120.2(2) . . ?
C1 C6 S1 120.35(16) . . ?
C5 C6 S1 119.14(17) . . ?
C5 C6 C1 120.4(2) . . ?
N007 C9 S3 114.17(16) . . ?
N007 C9 C10 124.7(2) . . ?
C10 C9 S3 121.16(16) . . ?
S3 C7 S2 124.47(13) . . ?
C8 C7 S3 110.82(16) . . ?
C8 C7 S2 124.70(17) . . ?
C3 C2 C1 121.3(2) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 C16 120.1(2) . . ?
C3 C4 C16 119.8(2) . . ?
C12 C11 C10 120.8(2) . . ?
C14 C15 C10 120.3(2) . . ?
C13 C14 C15 120.4(2) . . ?
C2 C3 C4 119.9(2) . . ?
F1 C16 F3 105.45(18) . . ?
F1 C16 C4 112.3(2) . . ?
F3 C16 C4 112.7(2) . . ?
F2 C16 F1 105.0(2) . . ?
F2 C16 F3 107.7(2) . . ?
F2 C16 C4 112.98(18) . . ?
C14 C13 C12 119.8(2) . . ?
C13 C12 C11 120.0(2) . . ?

_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.807
