# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1913803'
loop_
_audit_author_name
_audit_author_address
'Bulat Gabidullin' 'University of Ottawa'
_audit_update_record             
;
2019-05-03 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 F3 N4 O5 Re S'
_chemical_formula_weight         703.66

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'
F F 0.0171 0.0103 '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'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.3001(2)
_cell_length_b                   14.2559(4)
_cell_length_c                   22.3731(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.9490(10)
_cell_angle_gamma                90
_cell_volume                     2300.01(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5107
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.31

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.444
_shelx_estimated_absorpt_T_min   0.172
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6038
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16868
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.843
_diffrn_reflns_theta_max         28.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2872
_reflns_number_gt                2334
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0225P)²] 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         2872
_refine_ls_number_parameters     204
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0565
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_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
Re1 Re 0.5000 0.64318(2) 0.2500 0.02621(8) Uani 1 2 d S T P . .
N1 N 0.6521(5) 0.6243(2) 0.17747(16) 0.0298(8) Uani 1 1 d . . . . .
C2 C 0.8030(6) 0.6744(3) 0.1690(2) 0.0363(11) Uani 1 1 d . . . . .
H2 H 0.8454 0.7225 0.1972 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8978(6) 0.6588(4) 0.1215(2) 0.0455(13) Uani 1 1 d . . . . .
H3 H 1.0014 0.6968 0.1166 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8427(7) 0.5887(4) 0.0816(2) 0.0556(15) Uani 1 1 d . . . . .
H4 H 0.9070 0.5770 0.0485 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6925(7) 0.5354(4) 0.0900(2) 0.0514(14) Uani 1 1 d . . . . .
H5 H 0.6532 0.4852 0.0631 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5986(6) 0.5549(3) 0.13752(19) 0.0346(10) Uani 1 1 d . . . . .
C7 C 0.4290(6) 0.5040(3) 0.1467(2) 0.0346(10) Uani 1 1 d . . . . .
C8 C 0.3456(7) 0.4356(4) 0.1082(2) 0.0500(13) Uani 1 1 d . . . . .
H8 H 0.3997 0.4165 0.0742 0.060 Uiso 1 1 calc R U . . .
C9 C 0.1833(8) 0.3953(4) 0.1196(3) 0.0550(15) Uani 1 1 d . . . . .
H9 H 0.1229 0.3488 0.0932 0.066 Uiso 1 1 calc R U . . .
C10 C 0.1096(7) 0.4234(3) 0.1695(2) 0.0495(13) Uani 1 1 d . . . . .
H10 H -0.0032 0.3970 0.1779 0.059 Uiso 1 1 calc R U . . .
C11 C 0.2003(6) 0.4894(3) 0.2068(2) 0.0410(12) Uani 1 1 d . . . . .
H11 H 0.1508 0.5066 0.2421 0.049 Uiso 1 1 calc R U . . .
N12 N 0.3572(4) 0.5316(2) 0.19601(16) 0.0296(8) Uani 1 1 d . . . . .
C13 C 0.6582(6) 0.7381(3) 0.2868(2) 0.0321(10) Uani 1 1 d . . . . .
O14 O 0.7619(4) 0.7973(2) 0.30429(15) 0.0452(9) Uani 1 1 d . . . . .
S15 S 0.6902(7) 0.7071(4) 0.4830(2) 0.0396(9) Uani 0.5 1 d D U P A -1
O16 O 0.667(2) 0.7390(12) 0.4206(6) 0.052(3) Uani 0.5 1 d D U P A -1
O17 O 0.8130(16) 0.6259(10) 0.4970(8) 0.054(3) Uani 0.5 1 d D U P A -1
O18 O 0.514(2) 0.7214(9) 0.5046(9) 0.063(4) Uani 0.5 1 d D U P A -1
C19 C 0.834(2) 0.7993(13) 0.5199(8) 0.038(3) Uani 0.5 1 d D U P A -1
F20 F 0.9770(19) 0.8134(8) 0.4914(8) 0.066(3) Uani 0.5 1 d D U P A -1
F21 F 0.7577(15) 0.8815(8) 0.5127(7) 0.066(3) Uani 0.5 1 d D U P A -1
F22 F 0.877(2) 0.7855(11) 0.5778(5) 0.061(3) Uani 0.5 1 d D U P A -1


_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
Re1 C13 1.883(5) . ?
Re1 C13 1.883(5) 2_655 ?
Re1 N1 2.121(3) . ?
Re1 N1 2.121(3) 2_655 ?
Re1 N12 2.165(3) 2_655 ?
Re1 N12 2.165(3) . ?
N1 C6 1.350(5) . ?
N1 C2 1.350(5) . ?
C2 C3 1.373(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.359(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.477(6) . ?
C7 N12 1.350(5) . ?
C7 C8 1.379(6) . ?
C8 C9 1.375(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.359(6) . ?
C10 H10 0.9500 . ?
C11 N12 1.348(5) . ?
C11 H11 0.9500 . ?
C13 O14 1.160(5) . ?
S15 O16 1.453(10) . ?
S15 O18 1.457(11) . ?
S15 O17 1.468(10) . ?
S15 C19 1.802(13) . ?
C19 F21 1.298(15) . ?
C19 F22 1.300(15) . ?
C19 F20 1.318(15) . ?

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
C13 Re1 C13 88.2(2) . 2_655 ?
C13 Re1 N1 93.87(15) . . ?
C13 Re1 N1 96.60(16) 2_655 . ?
C13 Re1 N1 96.60(16) . 2_655 ?
C13 Re1 N1 93.87(15) 2_655 2_655 ?
N1 Re1 N1 165.41(18) . 2_655 ?
C13 Re1 N12 94.28(15) . 2_655 ?
C13 Re1 N12 168.95(15) 2_655 2_655 ?
N1 Re1 N12 93.99(13) . 2_655 ?
N1 Re1 N12 75.15(13) 2_655 2_655 ?
C13 Re1 N12 168.95(15) . . ?
C13 Re1 N12 94.28(15) 2_655 . ?
N1 Re1 N12 75.15(13) . . ?
N1 Re1 N12 93.99(13) 2_655 . ?
N12 Re1 N12 85.38(17) 2_655 . ?
C6 N1 C2 117.0(4) . . ?
C6 N1 Re1 117.9(3) . . ?
C2 N1 Re1 125.1(3) . . ?
N1 C2 C3 122.9(4) . . ?
N1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.6(5) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
N1 C6 C5 122.0(4) . . ?
N1 C6 C7 115.5(4) . . ?
C5 C6 C7 122.5(4) . . ?
N12 C7 C8 121.7(4) . . ?
N12 C7 C6 114.3(4) . . ?
C8 C7 C6 123.9(4) . . ?
C9 C8 C7 119.3(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 119.1(5) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N12 C11 C10 123.1(5) . . ?
N12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 N12 C7 117.7(4) . . ?
C11 N12 Re1 125.2(3) . . ?
C7 N12 Re1 117.1(3) . . ?
O14 C13 Re1 173.5(4) . . ?
O16 S15 O18 107.4(11) . . ?
O16 S15 O17 115.3(11) . . ?
O18 S15 O17 125.5(9) . . ?
O16 S15 C19 100.6(6) . . ?
O18 S15 C19 103.3(7) . . ?
O17 S15 C19 100.6(6) . . ?
F21 C19 F22 107.1(16) . . ?
F21 C19 F20 99.2(16) . . ?
F22 C19 F20 114.7(15) . . ?
F21 C19 S15 113.0(11) . . ?
F22 C19 S15 112.3(12) . . ?
F20 C19 S15 109.8(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 1.6(7) . . . . ?
Re1 N1 C2 C3 179.4(3) . . . . ?
N1 C2 C3 C4 -1.7(8) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 1.4(8) . . . . ?
C2 N1 C6 C5 0.0(6) . . . . ?
Re1 N1 C6 C5 -178.0(4) . . . . ?
C2 N1 C6 C7 -177.7(4) . . . . ?
Re1 N1 C6 C7 4.4(5) . . . . ?
C4 C5 C6 N1 -1.5(8) . . . . ?
C4 C5 C6 C7 176.1(5) . . . . ?
N1 C6 C7 N12 -3.1(6) . . . . ?
C5 C6 C7 N12 179.2(4) . . . . ?
N1 C6 C7 C8 175.3(4) . . . . ?
C5 C6 C7 C8 -2.4(7) . . . . ?
N12 C7 C8 C9 1.1(7) . . . . ?
C6 C7 C8 C9 -177.2(4) . . . . ?
C7 C8 C9 C10 -0.9(8) . . . . ?
C8 C9 C10 C11 -0.7(8) . . . . ?
C9 C10 C11 N12 2.4(7) . . . . ?
C10 C11 N12 C7 -2.2(7) . . . . ?
C10 C11 N12 Re1 176.0(3) . . . . ?
C8 C7 N12 C11 0.4(7) . . . . ?
C6 C7 N12 C11 178.8(4) . . . . ?
C8 C7 N12 Re1 -177.9(3) . . . . ?
C6 C7 N12 Re1 0.5(5) . . . . ?
O16 S15 C19 F21 59.6(16) . . . . ?
O18 S15 C19 F21 -51.2(16) . . . . ?
O17 S15 C19 F21 178.2(19) . . . . ?
O16 S15 C19 F22 -179(2) . . . . ?
O18 S15 C19 F22 70.1(16) . . . . ?
O17 S15 C19 F22 -60.6(16) . . . . ?
O16 S15 C19 F20 -50.1(15) . . . . ?
O18 S15 C19 F20 -161.0(17) . . . . ?
O17 S15 C19 F20 68.4(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 O17 0.95 2.57 3.310(18) 135.2 6_565
C5 H5 F21 0.95 2.41 3.238(16) 144.8 4_645
C8 H8 F20 0.95 2.35 3.253(13) 157.8 4_645
C10 H10 O14 0.95 2.45 3.380(6) 167.7 4_545

_refine_diff_density_max         1.285
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.165

