# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_5c
_database_code_depnum_ccdc_archive 'CCDC 1487876'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H15 N4 O5 Re'
_chemical_formula_sum            'C15 H15 N4 O5 Re'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         517.51

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'
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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   16.127(2)
_cell_length_b                   15.010(2)
_cell_length_c                   7.2212(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.0350(10)
_cell_angle_gamma                90
_cell_volume                     1652.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.5
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    7.389
_shelx_estimated_absorpt_T_min   0.119
_shelx_estimated_absorpt_T_max   0.404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.19
_exptl_absorpt_correction_T_max  0.40
_exptl_absorpt_process_details   
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7212
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.904
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3612
_reflns_number_gt                3533
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker AXS, 2008)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.012(9)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C c'
_symmetry_int_tables_number      9
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3612
_refine_ls_number_parameters     230
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0167
_refine_ls_R_factor_gt           0.0163
_refine_ls_wR_factor_ref         0.0374
_refine_ls_wR_factor_gt          0.0373
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.887
_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 0.39784(3) 0.17326(2) 0.71157(3) 0.01165(6) Uani 1 1 d . . . . .
O1 O 0.2773(3) 0.1519(3) 0.4726(6) 0.0155(8) Uani 1 1 d . . . . .
N1 N 0.3040(3) 0.1347(3) 0.8508(6) 0.0136(8) Uani 1 1 d . . . . .
C1 C 0.2976(3) 0.1280(3) 1.0360(8) 0.0147(10) Uani 1 1 d . . . . .
H1 H 0.3444 0.1358 1.1554 0.018 Uiso 1 1 calc R U . . .
O2 O 0.1355(2) 0.1112(2) 0.3898(5) 0.0168(8) Uani 1 1 d . . . . .
N2 N 0.1671(3) 0.1027(3) 0.8229(7) 0.0141(10) Uani 1 1 d . . . . .
C2 C 0.2128(3) 0.1081(3) 1.0195(7) 0.0152(10) Uani 1 1 d . . . . .
H2 H 0.1899 0.0997 1.1239 0.018 Uiso 1 1 calc R U . . .
O3 O 0.5556(2) 0.2079(3) 1.0775(6) 0.0201(8) Uani 1 1 d . . . . .
N3 N 0.3462(3) 0.3106(3) 0.7141(7) 0.0135(9) Uani 1 1 d . . . . .
C3 C 0.2234(3) 0.1184(3) 0.7247(7) 0.0125(10) Uani 1 1 d . . . . .
O4 O 0.5062(3) 0.2359(3) 0.4579(6) 0.0254(9) Uani 1 1 d . . . . .
N4 N 0.2584(3) 0.5759(4) 0.6946(8) 0.0191(12) Uani 1 1 d . . . . .
C4 C 0.2077(3) 0.1259(3) 0.5107(7) 0.0138(10) Uani 1 1 d . . . . .
O5 O 0.4769(3) -0.0129(3) 0.7161(6) 0.0256(9) Uani 1 1 d . . . . .
C5 C 0.0733(4) 0.0822(5) 0.7414(9) 0.0154(13) Uani 1 1 d . . . . .
H5A H 0.0518 0.0987 0.6025 0.023 Uiso 1 1 calc R U . . .
H5B H 0.0412 0.1159 0.8124 0.023 Uiso 1 1 calc R U . . .
H5C H 0.0643 0.0182 0.7548 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2612(4) 0.3318(3) 0.6833(8) 0.0157(11) Uani 1 1 d . . . . .
H6 H 0.2205 0.2841 0.6637 0.019 Uiso 1 1 calc R U . . .
C7 C 0.2293(3) 0.4164(3) 0.6780(8) 0.0155(10) Uani 1 1 d . . . . .
H7 H 0.1686 0.4256 0.6573 0.019 Uiso 1 1 calc R U . . .
C8 C 0.2862(3) 0.4902(3) 0.7032(8) 0.0148(10) Uani 1 1 d . . . . .
C9 C 0.3752(3) 0.4677(4) 0.7403(8) 0.0178(11) Uani 1 1 d . . . . .
H9 H 0.4173 0.5142 0.7636 0.021 Uiso 1 1 calc R U . . .
C10 C 0.4031(6) 0.3814(3) 0.7440(9) 0.0151(15) Uani 1 1 d . . . . .
H10 H 0.4637 0.3700 0.7681 0.018 Uiso 1 1 calc R U . . .
C11 C 0.1657(4) 0.5968(4) 0.6433(10) 0.0240(15) Uani 1 1 d . . . . .
H11A H 0.1358 0.5813 0.5058 0.036 Uiso 1 1 calc R U . . .
H11B H 0.1586 0.6607 0.6623 0.036 Uiso 1 1 calc R U . . .
H11C H 0.1402 0.5627 0.7271 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3198(4) 0.6488(4) 0.7218(9) 0.0207(12) Uani 1 1 d . . . . .
H12A H 0.3717 0.6366 0.8355 0.031 Uiso 1 1 calc R U . . .
H12B H 0.2920 0.7040 0.7439 0.031 Uiso 1 1 calc R U . . .
H12C H 0.3372 0.6552 0.6046 0.031 Uiso 1 1 calc R U . . .
C13 C 0.4962(4) 0.1956(4) 0.9379(9) 0.0142(11) Uani 1 1 d . . . . .
C14 C 0.4663(3) 0.2121(3) 0.5528(8) 0.0160(11) Uani 1 1 d . . . . .
C15 C 0.4445(3) 0.0556(3) 0.7118(8) 0.0161(11) 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
Re1 C13 1.899(6) . ?
Re1 C15 1.920(5) . ?
Re1 C14 1.923(6) . ?
Re1 N1 2.152(4) . ?
Re1 O1 2.161(4) . ?
Re1 N3 2.226(4) . ?
O1 C4 1.299(6) . ?
N1 C3 1.344(6) . ?
N1 C1 1.378(6) . ?
C1 C2 1.367(7) . ?
C1 H1 0.9500 . ?
O2 C4 1.227(6) . ?
N2 C3 1.343(7) . ?
N2 C2 1.372(7) . ?
N2 C5 1.466(7) . ?
C2 H2 0.9500 . ?
O3 C13 1.157(7) . ?
N3 C6 1.353(7) . ?
N3 C10 1.374(8) . ?
C3 C4 1.487(7) . ?
O4 C14 1.140(6) . ?
N4 C8 1.357(7) . ?
N4 C12 1.445(7) . ?
N4 C11 1.452(7) . ?
O5 C15 1.148(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.366(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.413(7) . ?
C9 C10 1.369(8) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 C15 86.8(2) . . ?
C13 Re1 C14 88.8(2) . . ?
C15 Re1 C14 88.7(2) . . ?
C13 Re1 N1 99.4(2) . . ?
C15 Re1 N1 95.04(19) . . ?
C14 Re1 N1 171.16(19) . . ?
C13 Re1 O1 173.9(2) . . ?
C15 Re1 O1 96.59(19) . . ?
C14 Re1 O1 96.33(19) . . ?
N1 Re1 O1 75.32(16) . . ?
C13 Re1 N3 92.3(2) . . ?
C15 Re1 N3 178.94(19) . . ?
C14 Re1 N3 90.76(19) . . ?
N1 Re1 N3 85.58(16) . . ?
O1 Re1 N3 84.40(15) . . ?
C4 O1 Re1 119.3(3) . . ?
C3 N1 C1 106.4(4) . . ?
C3 N1 Re1 113.9(3) . . ?
C1 N1 Re1 139.5(3) . . ?
C2 C1 N1 108.7(4) . . ?
C2 C1 H1 125.6 . . ?
N1 C1 H1 125.6 . . ?
C3 N2 C2 108.0(4) . . ?
C3 N2 C5 127.7(5) . . ?
C2 N2 C5 124.3(5) . . ?
C1 C2 N2 106.7(5) . . ?
C1 C2 H2 126.7 . . ?
N2 C2 H2 126.7 . . ?
C6 N3 C10 115.7(5) . . ?
C6 N3 Re1 125.3(3) . . ?
C10 N3 Re1 119.0(4) . . ?
N2 C3 N1 110.2(4) . . ?
N2 C3 C4 130.4(5) . . ?
N1 C3 C4 119.3(4) . . ?
C8 N4 C12 120.7(5) . . ?
C8 N4 C11 120.9(5) . . ?
C12 N4 C11 118.2(5) . . ?
O2 C4 O1 126.1(5) . . ?
O2 C4 C3 121.7(5) . . ?
O1 C4 C3 112.2(4) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 125.1(5) . . ?
N3 C6 H6 117.4 . . ?
C7 C6 H6 117.4 . . ?
C6 C7 C8 120.1(5) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N4 C8 C7 123.2(5) . . ?
N4 C8 C9 122.3(5) . . ?
C7 C8 C9 114.5(5) . . ?
C10 C9 C8 122.5(6) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 N3 122.0(7) . . ?
C9 C10 H10 119.0 . . ?
N3 C10 H10 119.0 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 Re1 178.7(5) . . ?
O4 C14 Re1 179.2(5) . . ?
O5 C15 Re1 176.3(5) . . ?

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
C3 N1 C1 C2 -0.3(5) . . . . ?
Re1 N1 C1 C2 172.7(4) . . . . ?
N1 C1 C2 N2 0.0(6) . . . . ?
C3 N2 C2 C1 0.4(6) . . . . ?
C5 N2 C2 C1 179.7(5) . . . . ?
C2 N2 C3 N1 -0.6(6) . . . . ?
C5 N2 C3 N1 -179.9(5) . . . . ?
C2 N2 C3 C4 -176.0(5) . . . . ?
C5 N2 C3 C4 4.7(9) . . . . ?
C1 N1 C3 N2 0.6(5) . . . . ?
Re1 N1 C3 N2 -174.5(3) . . . . ?
C1 N1 C3 C4 176.5(4) . . . . ?
Re1 N1 C3 C4 1.5(5) . . . . ?
Re1 O1 C4 O2 -179.9(4) . . . . ?
Re1 O1 C4 C3 2.4(5) . . . . ?
N2 C3 C4 O2 -5.4(8) . . . . ?
N1 C3 C4 O2 179.6(4) . . . . ?
N2 C3 C4 O1 172.5(5) . . . . ?
N1 C3 C4 O1 -2.6(6) . . . . ?
C10 N3 C6 C7 0.8(8) . . . . ?
Re1 N3 C6 C7 -177.5(4) . . . . ?
N3 C6 C7 C8 0.9(9) . . . . ?
C12 N4 C8 C7 179.9(5) . . . . ?
C11 N4 C8 C7 -4.8(9) . . . . ?
C12 N4 C8 C9 0.6(9) . . . . ?
C11 N4 C8 C9 175.9(5) . . . . ?
C6 C7 C8 N4 178.3(5) . . . . ?
C6 C7 C8 C9 -2.3(7) . . . . ?
N4 C8 C9 C10 -178.3(6) . . . . ?
C7 C8 C9 C10 2.3(8) . . . . ?
C8 C9 C10 N3 -0.8(9) . . . . ?
C6 N3 C10 C9 -0.8(8) . . . . ?
Re1 N3 C10 C9 177.6(5) . . . . ?

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
C2 H2 O1 0.95 2.57 3.162(6) 120.3 1_556
C2 H2 O2 0.95 2.36 3.298(6) 168.1 1_556
C5 H5A O2 0.98 2.36 3.050(7) 126.8 .
C5 H5B O4 0.98 2.60 3.490(8) 151.0 4_455
C5 H5C O2 0.98 2.30 3.142(7) 142.9 2
C6 H6 O3 0.95 2.53 3.206(7) 128.3 4_454
C7 H7 O3 0.95 2.64 3.244(6) 121.7 4_454
C10 H10 O2 0.95 2.63 3.549(9) 161.6 4
C2 H2 O1 0.95 2.57 3.162(6) 120.3 1_556
C2 H2 O2 0.95 2.36 3.298(6) 168.1 1_556
C5 H5A O2 0.98 2.36 3.050(7) 126.8 .
C5 H5B O4 0.98 2.60 3.490(8) 151.0 4_455
C5 H5C O2 0.98 2.30 3.142(7) 142.9 2
C6 H6 O3 0.95 2.53 3.206(7) 128.3 4_454
C7 H7 O3 0.95 2.64 3.244(6) 121.7 4_454
C10 H10 O2 0.95 2.63 3.549(9) 161.6 4

_refine_diff_density_max         0.940
_refine_diff_density_min         -1.027
_refine_diff_density_rms         0.089

_diffrn_standards_decay_%        0.0

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1487879'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H18 N4 O3 Re, C1 F3 O3 S1, 0.5(C1 H4 O)'
_chemical_formula_sum            'C21.50 H20 F3 N4 O6.50 Re S'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         713.67

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                   25.988(6)
_cell_length_b                   12.548(3)
_cell_length_c                   14.946(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.685(2)
_cell_angle_gamma                90
_cell_volume                     4850.0(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.4
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_F_000             2776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    5.169
_shelx_estimated_absorpt_T_min   0.182
_shelx_estimated_absorpt_T_max   0.358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.21
_exptl_absorpt_correction_T_max  0.36
_exptl_absorpt_process_details   
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26618
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.804
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5537
_reflns_number_gt                4355
_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       'APEX2 (Bruker AXS, 2008)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_refine_special_details          
;
 The H atoms of a disordered MeOH were not included in the model 
 but weer included in the sum formula.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0189P)²+42.2602P] 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         5537
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.003
_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 0.35445(2) 0.74675(2) 0.71965(2) 0.02449(6) Uani 1 1 d . . . . .
S1 S 0.35643(7) 0.79919(10) 0.19032(9) 0.0471(4) Uani 1 1 d . . . . .
F1 F 0.33366(15) 0.6680(3) 0.0573(2) 0.0628(10) Uani 1 1 d . . . . .
O1 O 0.43387(16) 0.8433(3) 0.8627(2) 0.0459(9) Uani 1 1 d . . . . .
N1 N 0.30712(14) 0.6725(3) 0.6091(2) 0.0259(7) Uani 1 1 d . . . . .
C1 C 0.27346(18) 0.5930(3) 0.6184(3) 0.0302(9) Uani 1 1 d . . . . .
H1 H 0.2660 0.5738 0.6772 0.036 Uiso 1 1 calc R U . . .
F2 F 0.26877(16) 0.7556(4) 0.0953(3) 0.0910(16) Uani 1 1 d . . . . .
O2 O 0.32230(15) 0.5965(3) 0.8663(2) 0.0426(9) Uani 1 1 d . . . . .
N2 N 0.37073(16) 0.8353(3) 0.6014(3) 0.0335(9) Uani 1 1 d . . . . .
C2 C 0.24926(18) 0.5380(4) 0.5456(3) 0.0339(10) Uani 1 1 d . . . . .
H2 H 0.2257 0.4821 0.5546 0.041 Uiso 1 1 calc R U . . .
F3 F 0.32548(15) 0.8326(3) 0.0209(3) 0.0749(12) Uani 1 1 d . . . . .
O3 O 0.27161(15) 0.9041(3) 0.7714(2) 0.0439(9) Uani 1 1 d . . . . .
N3 N 0.41272(14) 0.6349(3) 0.6769(2) 0.0231(7) Uani 1 1 d . . . . .
C3 C 0.25979(18) 0.5655(4) 0.4598(3) 0.0335(10) Uani 1 1 d . . . . .
H3 H 0.2440 0.5283 0.4089 0.040 Uiso 1 1 calc R U . . .
O4 O 0.40801(16) 0.8085(3) 0.1640(2) 0.0497(9) Uani 1 1 d . . . . .
N4 N 0.52409(14) 0.4182(3) 0.6022(3) 0.0322(8) Uani 1 1 d . . . . .
C4 C 0.29405(17) 0.6489(4) 0.4493(3) 0.0297(9) Uani 1 1 d . . . . .
H4 H 0.3018 0.6695 0.3910 0.036 Uiso 1 1 calc R U . . .
O5 O 0.34900(17) 0.7094(3) 0.2488(2) 0.0492(10) Uani 1 1 d . . . . .
C5 C 0.31687(16) 0.7018(3) 0.5247(3) 0.0248(9) Uani 1 1 d . . . . .
O6 O 0.3335(3) 0.8974(4) 0.2159(3) 0.0905(19) Uani 1 1 d . . . . .
C6 C 0.35200(18) 0.7940(3) 0.5208(3) 0.0287(9) Uani 1 1 d . . . . .
C7 C 0.36342(19) 0.8396(4) 0.4402(3) 0.0333(10) Uani 1 1 d . . . . .
H7 H 0.3504 0.8090 0.3843 0.040 Uiso 1 1 calc R U . . .
C8 C 0.3939(3) 0.9300(4) 0.4425(4) 0.0492(15) Uani 1 1 d . . . . .
H8 H 0.4028 0.9614 0.3882 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4114(3) 0.9741(4) 0.5241(4) 0.0565(17) Uani 1 1 d . . . . .
H9 H 0.4316 1.0374 0.5270 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3991(3) 0.9249(4) 0.6017(4) 0.0527(16) Uani 1 1 d . . . . .
H10 H 0.4113 0.9556 0.6580 0.063 Uiso 1 1 calc R U . . .
C11 C 0.45867(17) 0.6672(3) 0.6511(3) 0.0259(9) Uani 1 1 d . . . . .
H11 H 0.4651 0.7416 0.6494 0.031 Uiso 1 1 calc R U . . .
C12 C 0.49642(16) 0.6001(4) 0.6272(3) 0.0266(9) Uani 1 1 d . . . . .
H12 H 0.5279 0.6287 0.6104 0.032 Uiso 1 1 calc R U . . .
C13 C 0.48899(17) 0.4885(3) 0.6273(3) 0.0264(9) Uani 1 1 d . . . . .
C14 C 0.44133(16) 0.4542(3) 0.6559(3) 0.0248(8) Uani 1 1 d . . . . .
H14 H 0.4340 0.3802 0.6596 0.030 Uiso 1 1 calc R U . . .
C15 C 0.40571(16) 0.5277(3) 0.6784(3) 0.0234(8) Uani 1 1 d . . . . .
H15 H 0.3739 0.5018 0.6961 0.028 Uiso 1 1 calc R U . . .
C16 C 0.57603(18) 0.4504(5) 0.5841(3) 0.0396(11) Uani 1 1 d . . . . .
H16A H 0.5762 0.5268 0.5707 0.059 Uiso 1 1 calc R U . . .
H16B H 0.5863 0.4103 0.5325 0.059 Uiso 1 1 calc R U . . .
H16C H 0.6004 0.4356 0.6370 0.059 Uiso 1 1 calc R U . . .
C17 C 0.5161(2) 0.3033(4) 0.6078(4) 0.0446(13) Uani 1 1 d . . . . .
H17A H 0.5221 0.2805 0.6707 0.067 Uiso 1 1 calc R U . . .
H17B H 0.5403 0.2663 0.5722 0.067 Uiso 1 1 calc R U . . .
H17C H 0.4806 0.2859 0.5843 0.067 Uiso 1 1 calc R U . . .
C18 C 0.4036(2) 0.8085(3) 0.8084(3) 0.0350(11) Uani 1 1 d . . . . .
C19 C 0.33492(19) 0.6534(3) 0.8122(3) 0.0305(10) Uani 1 1 d . . . . .
C20 C 0.3022(2) 0.8464(3) 0.7516(3) 0.0351(11) Uani 1 1 d . . . . .
C21 C 0.3192(2) 0.7618(5) 0.0851(4) 0.0511(15) Uani 1 1 d . . . . .
C1M C 0.5000 0.9644(16) 0.2500 0.146(10) Uani 1 2 d S T P . .
O1M O 0.4638(7) 0.9434(10) 0.2644(8) 0.116(5) Uani 0.5 1 d . . P . .


_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 C18 1.912(5) . ?
Re1 C19 1.919(4) . ?
Re1 C20 1.939(5) . ?
Re1 N2 2.164(4) . ?
Re1 N1 2.171(4) . ?
Re1 N3 2.206(3) . ?
S1 O6 1.437(4) . ?
S1 O4 1.439(4) . ?
S1 O5 1.450(4) . ?
S1 C21 1.825(7) . ?
F1 C21 1.315(7) . ?
O1 C18 1.158(6) . ?
N1 C1 1.342(6) . ?
N1 C5 1.361(5) . ?
C1 C2 1.385(7) . ?
C1 H1 0.9500 . ?
F2 C21 1.336(7) . ?
O2 C19 1.150(5) . ?
N2 C10 1.345(6) . ?
N2 C6 1.357(6) . ?
C2 C3 1.382(7) . ?
C2 H2 0.9500 . ?
F3 C21 1.329(6) . ?
O3 C20 1.137(6) . ?
N3 C11 1.353(5) . ?
N3 C15 1.358(5) . ?
C3 C4 1.393(7) . ?
C3 H3 0.9500 . ?
N4 C13 1.349(6) . ?
N4 C16 1.460(6) . ?
N4 C17 1.460(6) . ?
C4 C5 1.389(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.479(6) . ?
C6 C7 1.392(6) . ?
C7 C8 1.383(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.375(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.367(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.414(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.417(6) . ?
C14 C15 1.371(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C1M O1M 1.020(16) . ?
C1M O1M 1.020(16) 2_655 ?

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
C18 Re1 C19 87.3(2) . . ?
C18 Re1 C20 90.2(2) . . ?
C19 Re1 C20 88.55(18) . . ?
C18 Re1 N2 100.77(18) . . ?
C19 Re1 N2 171.50(17) . . ?
C20 Re1 N2 93.91(16) . . ?
C18 Re1 N1 172.54(17) . . ?
C19 Re1 N1 96.70(17) . . ?
C20 Re1 N1 96.14(18) . . ?
N2 Re1 N1 74.95(14) . . ?
C18 Re1 N3 91.60(16) . . ?
C19 Re1 N3 93.35(15) . . ?
C20 Re1 N3 177.44(16) . . ?
N2 Re1 N3 83.96(13) . . ?
N1 Re1 N3 81.93(13) . . ?
O6 S1 O4 115.1(3) . . ?
O6 S1 O5 115.0(3) . . ?
O4 S1 O5 114.3(2) . . ?
O6 S1 C21 104.6(3) . . ?
O4 S1 C21 102.4(2) . . ?
O5 S1 C21 103.2(3) . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Re1 124.4(3) . . ?
C5 N1 Re1 116.5(3) . . ?
N1 C1 C2 122.6(4) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C10 N2 C6 118.1(4) . . ?
C10 N2 Re1 125.3(3) . . ?
C6 N2 Re1 116.6(3) . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C11 N3 C15 115.2(4) . . ?
C11 N3 Re1 122.9(3) . . ?
C15 N3 Re1 121.9(3) . . ?
C2 C3 C4 118.6(4) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C13 N4 C16 122.2(4) . . ?
C13 N4 C17 121.7(4) . . ?
C16 N4 C17 115.1(4) . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 121.2(4) . . ?
N1 C5 C6 114.9(4) . . ?
C4 C5 C6 123.8(4) . . ?
N2 C6 C7 121.6(4) . . ?
N2 C6 C5 115.6(4) . . ?
C7 C6 C5 122.8(4) . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 118.9(5) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
N2 C10 C9 122.9(5) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N3 C11 C12 124.5(4) . . ?
N3 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
N4 C13 C12 123.5(4) . . ?
N4 C13 C14 121.4(4) . . ?
C12 C13 C14 115.1(4) . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N3 C15 C14 124.5(4) . . ?
N3 C15 H15 117.7 . . ?
C14 C15 H15 117.7 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 Re1 178.2(4) . . ?
O2 C19 Re1 178.4(5) . . ?
O3 C20 Re1 179.0(4) . . ?
F1 C21 F3 108.1(5) . . ?
F1 C21 F2 107.4(6) . . ?
F3 C21 F2 108.3(4) . . ?
F1 C21 S1 111.0(4) . . ?
F3 C21 S1 110.9(5) . . ?
F2 C21 S1 111.0(4) . . ?
O1M C1M O1M 150(3) . 2_655 ?

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
C5 N1 C1 C2 1.6(6) . . . . ?
Re1 N1 C1 C2 -170.9(3) . . . . ?
N1 C1 C2 C3 -0.2(7) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C1 N1 C5 C4 -2.1(6) . . . . ?
Re1 N1 C5 C4 171.0(3) . . . . ?
C1 N1 C5 C6 176.5(4) . . . . ?
Re1 N1 C5 C6 -10.3(4) . . . . ?
C3 C4 C5 N1 1.2(6) . . . . ?
C3 C4 C5 C6 -177.4(4) . . . . ?
C10 N2 C6 C7 2.8(7) . . . . ?
Re1 N2 C6 C7 -175.0(3) . . . . ?
C10 N2 C6 C5 -174.2(5) . . . . ?
Re1 N2 C6 C5 8.0(5) . . . . ?
N1 C5 C6 N2 1.6(5) . . . . ?
C4 C5 C6 N2 -179.8(4) . . . . ?
N1 C5 C6 C7 -175.4(4) . . . . ?
C4 C5 C6 C7 3.2(7) . . . . ?
N2 C6 C7 C8 -1.0(7) . . . . ?
C5 C6 C7 C8 175.8(4) . . . . ?
C6 C7 C8 C9 -1.3(8) . . . . ?
C7 C8 C9 C10 1.8(10) . . . . ?
C6 N2 C10 C9 -2.3(9) . . . . ?
Re1 N2 C10 C9 175.3(5) . . . . ?
C8 C9 C10 N2 0.0(10) . . . . ?
C15 N3 C11 C12 0.2(6) . . . . ?
Re1 N3 C11 C12 177.6(3) . . . . ?
N3 C11 C12 C13 0.7(6) . . . . ?
C16 N4 C13 C12 8.5(6) . . . . ?
C17 N4 C13 C12 176.7(4) . . . . ?
C16 N4 C13 C14 -171.6(4) . . . . ?
C17 N4 C13 C14 -3.4(6) . . . . ?
C11 C12 C13 N4 178.2(4) . . . . ?
C11 C12 C13 C14 -1.8(6) . . . . ?
N4 C13 C14 C15 -177.9(4) . . . . ?
C12 C13 C14 C15 2.0(6) . . . . ?
C11 N3 C15 C14 0.0(6) . . . . ?
Re1 N3 C15 C14 -177.4(3) . . . . ?
C13 C14 C15 N3 -1.2(6) . . . . ?
O6 S1 C21 F1 -175.2(4) . . . . ?
O4 S1 C21 F1 64.4(4) . . . . ?
O5 S1 C21 F1 -54.5(5) . . . . ?
O6 S1 C21 F3 64.6(5) . . . . ?
O4 S1 C21 F3 -55.8(4) . . . . ?
O5 S1 C21 F3 -174.7(4) . . . . ?
O6 S1 C21 F2 -55.9(5) . . . . ?
O4 S1 C21 F2 -176.3(4) . . . . ?
O5 S1 C21 F2 64.8(5) . . . . ?

_refine_diff_density_max         1.409
_refine_diff_density_min         -2.319
_refine_diff_density_rms         0.122

_diffrn_standards_decay_%        0.0

####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1487877'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H22 N6 O3 Re, C F3 O3 S'
_chemical_formula_sum            'C25 H22 F3 N6 O6 Re S'
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         777.74

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.3595(8)
_cell_length_b                   11.0688(10)
_cell_length_c                   14.8076(13)
_cell_angle_alpha                86.3080(10)
_cell_angle_beta                 87.1240(10)
_cell_angle_gamma                86.9900(10)
_cell_volume                     1363.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.6
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    4.604
_shelx_estimated_absorpt_T_min   0.186
_shelx_estimated_absorpt_T_max   0.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_process_details   
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15308
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.846
_diffrn_reflns_theta_max         27.661
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6193
_reflns_number_gt                5840
_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       'APEX2 (Bruker AXS, 2008)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_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)+(0.0221P)²+0.4853P] 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         6193
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0446
_refine_ls_wR_factor_gt          0.0438
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.37982(2) -0.16210(2) 0.32506(2) 0.01175(3) Uani 1 1 d . . . . .
S1 S -0.13725(7) 0.46954(6) 0.29875(4) 0.01863(13) Uani 1 1 d . . . . .
F1 F -0.2573(3) 0.57796(16) 0.44127(13) 0.0487(5) Uani 1 1 d . . . . .
O1 O 0.3512(2) -0.43815(15) 0.35602(13) 0.0216(4) Uani 1 1 d . . . . .
N1 N 0.3681(2) 0.03168(17) 0.30945(13) 0.0135(4) Uani 1 1 d . . . . .
C1 C 0.2245(3) 0.0904(2) 0.33018(16) 0.0144(5) Uani 1 1 d . . . . .
F2 F -0.1106(2) 0.4170(2) 0.47211(12) 0.0484(5) Uani 1 1 d . . . . .
O2 O 0.7176(2) -0.19979(16) 0.23532(13) 0.0235(4) Uani 1 1 d . . . . .
N2 N 0.4747(2) 0.10975(17) 0.27840(14) 0.0147(4) Uani 1 1 d . . . . .
C2 C 0.2428(3) 0.2120(2) 0.31111(16) 0.0159(5) Uani 1 1 d . . . . .
H2 H 0.1648 0.2767 0.3182 0.019 Uiso 1 1 calc R U . . .
F3 F -0.3476(2) 0.40253(15) 0.42706(11) 0.0329(4) Uani 1 1 d . . . . .
O3 O 0.5074(2) -0.16745(16) 0.51604(12) 0.0195(4) Uani 1 1 d . . . . .
N3 N 0.3966(2) 0.21867(17) 0.27999(13) 0.0144(4) Uani 1 1 d . . . . .
C3 C 0.0932(3) 0.0147(2) 0.36341(15) 0.0131(4) Uani 1 1 d . . . . .
O4 O -0.0988(3) 0.34191(18) 0.28754(15) 0.0341(5) Uani 1 1 d . . . . .
N4 N 0.1346(2) -0.10569(17) 0.36975(13) 0.0136(4) Uani 1 1 d . . . . .
C4 C -0.0608(3) 0.0605(2) 0.38463(16) 0.0161(5) Uani 1 1 d . . . . .
H4 H -0.0866 0.1451 0.3783 0.019 Uiso 1 1 calc R U . . .
O5 O -0.0012(2) 0.5443(2) 0.29859(14) 0.0357(5) Uani 1 1 d . . . . .
N5 N 0.2757(2) -0.14750(17) 0.19056(14) 0.0144(4) Uani 1 1 d . . . . .
C5 C -0.1762(3) -0.0197(2) 0.41519(17) 0.0179(5) Uani 1 1 d . . . . .
H5 H -0.2825 0.0092 0.4305 0.021 Uiso 1 1 calc R U . . .
O6 O -0.2692(2) 0.51965(17) 0.24785(13) 0.0274(4) Uani 1 1 d . . . . .
N6 N 0.0910(3) -0.1293(2) -0.06851(15) 0.0228(5) Uani 1 1 d . . . . .
C6 C -0.1341(3) -0.1428(2) 0.42317(17) 0.0177(5) Uani 1 1 d . . . . .
H6 H -0.2112 -0.1991 0.4449 0.021 Uiso 1 1 calc R U . . .
C7 C 0.0207(3) -0.1830(2) 0.39922(16) 0.0154(5) Uani 1 1 d . . . . .
H7 H 0.0479 -0.2675 0.4036 0.018 Uiso 1 1 calc R U . . .
C8 C 0.4782(3) 0.3267(2) 0.23992(17) 0.0174(5) Uani 1 1 d . . . . .
H8A H 0.5958 0.3098 0.2377 0.021 Uiso 1 1 calc R U . . .
H8B H 0.4532 0.3961 0.2780 0.021 Uiso 1 1 calc R U . . .
C9 C 0.4225(3) 0.3579(2) 0.14530(17) 0.0171(5) Uani 1 1 d . . . . .
C10 C 0.2949(3) 0.4411(2) 0.13068(19) 0.0233(6) Uani 1 1 d . . . . .
H10 H 0.2427 0.4802 0.1801 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2440(4) 0.4667(3) 0.0434(2) 0.0321(7) Uani 1 1 d . . . . .
H11 H 0.1571 0.5241 0.0334 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3175(4) 0.4104(3) -0.0289(2) 0.0333(7) Uani 1 1 d . . . . .
H12 H 0.2813 0.4282 -0.0883 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4443(4) 0.3277(3) -0.0142(2) 0.0328(7) Uani 1 1 d . . . . .
H13 H 0.4962 0.2888 -0.0639 0.039 Uiso 1 1 calc R U . . .
C14 C 0.4963(3) 0.3011(3) 0.07244(19) 0.0262(6) Uani 1 1 d . . . . .
H14 H 0.5831 0.2436 0.0820 0.031 Uiso 1 1 calc R U . . .
C15 C 0.3259(3) -0.0675(2) 0.12399(17) 0.0172(5) Uani 1 1 d . . . . .
H15 H 0.4068 -0.0149 0.1371 0.021 Uiso 1 1 calc R U . . .
C16 C 0.2683(3) -0.0567(2) 0.03881(17) 0.0185(5) Uani 1 1 d . . . . .
H16 H 0.3088 0.0024 -0.0046 0.022 Uiso 1 1 calc R U . . .
C17 C 0.1486(3) -0.1332(2) 0.01495(17) 0.0177(5) Uani 1 1 d . . . . .
C18 C 0.0942(3) -0.2163(2) 0.08579(17) 0.0176(5) Uani 1 1 d . . . . .
H18 H 0.0123 -0.2693 0.0752 0.021 Uiso 1 1 calc R U . . .
C19 C 0.1589(3) -0.2205(2) 0.16914(17) 0.0167(5) Uani 1 1 d . . . . .
H19 H 0.1202 -0.2776 0.2146 0.020 Uiso 1 1 calc R U . . .
C20 C 0.1493(3) -0.0439(3) -0.14045(18) 0.0289(6) Uani 1 1 d . . . . .
H20A H 0.1652 0.0341 -0.1152 0.043 Uiso 1 1 calc R U . . .
H20B H 0.0705 -0.0325 -0.1874 0.043 Uiso 1 1 calc R U . . .
H20C H 0.2514 -0.0759 -0.1669 0.043 Uiso 1 1 calc R U . . .
C21 C -0.0185(4) -0.2193(3) -0.09275(19) 0.0293(6) Uani 1 1 d . . . . .
H21A H 0.0276 -0.3009 -0.0775 0.044 Uiso 1 1 calc R U . . .
H21B H -0.0351 -0.2098 -0.1579 0.044 Uiso 1 1 calc R U . . .
H21C H -0.1216 -0.2076 -0.0591 0.044 Uiso 1 1 calc R U . . .
C22 C 0.3614(3) -0.3351(2) 0.34253(16) 0.0154(5) Uani 1 1 d . . . . .
C23 C 0.5917(3) -0.1885(2) 0.27078(17) 0.0155(5) Uani 1 1 d . . . . .
C24 C 0.4601(3) -0.1661(2) 0.44416(17) 0.0149(5) Uani 1 1 d . . . . .
C25 C -0.2174(3) 0.4668(2) 0.41560(19) 0.0246(6) 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
Re1 C24 1.915(3) . ?
Re1 C23 1.924(2) . ?
Re1 C22 1.929(2) . ?
Re1 N1 2.1401(19) . ?
Re1 N4 2.1939(19) . ?
Re1 N5 2.206(2) . ?
S1 O6 1.4345(19) . ?
S1 O5 1.441(2) . ?
S1 O4 1.450(2) . ?
S1 C25 1.823(3) . ?
F1 C25 1.332(3) . ?
O1 C22 1.152(3) . ?
N1 N2 1.319(3) . ?
N1 C1 1.366(3) . ?
C1 C2 1.372(3) . ?
C1 C3 1.462(3) . ?
F2 C25 1.328(3) . ?
O2 C23 1.157(3) . ?
N2 N3 1.342(3) . ?
C2 N3 1.348(3) . ?
C2 H2 0.9500 . ?
F3 C25 1.330(3) . ?
O3 C24 1.153(3) . ?
N3 C8 1.483(3) . ?
C3 N4 1.358(3) . ?
C3 C4 1.387(3) . ?
N4 C7 1.351(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
N5 C15 1.348(3) . ?
N5 C19 1.361(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
N6 C17 1.346(3) . ?
N6 C20 1.461(3) . ?
N6 C21 1.461(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.512(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.386(4) . ?
C9 C10 1.388(4) . ?
C10 C11 1.389(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.368(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.416(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.423(3) . ?
C18 C19 1.370(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C24 Re1 C23 92.05(10) . . ?
C24 Re1 C22 87.71(10) . . ?
C23 Re1 C22 89.61(10) . . ?
C24 Re1 N1 93.70(9) . . ?
C23 Re1 N1 97.47(8) . . ?
C22 Re1 N1 172.72(8) . . ?
C24 Re1 N4 94.09(8) . . ?
C23 Re1 N4 170.17(8) . . ?
C22 Re1 N4 98.29(8) . . ?
N1 Re1 N4 74.49(7) . . ?
C24 Re1 N5 176.11(8) . . ?
C23 Re1 N5 90.98(9) . . ?
C22 Re1 N5 94.74(9) . . ?
N1 Re1 N5 83.49(7) . . ?
N4 Re1 N5 82.59(7) . . ?
O6 S1 O5 115.57(12) . . ?
O6 S1 O4 114.47(13) . . ?
O5 S1 O4 115.23(13) . . ?
O6 S1 C25 103.43(13) . . ?
O5 S1 C25 103.90(13) . . ?
O4 S1 C25 101.66(13) . . ?
N2 N1 C1 110.61(19) . . ?
N2 N1 Re1 131.86(15) . . ?
C1 N1 Re1 117.45(15) . . ?
N1 C1 C2 107.4(2) . . ?
N1 C1 C3 116.7(2) . . ?
C2 C1 C3 135.9(2) . . ?
N1 N2 N3 104.98(18) . . ?
N3 C2 C1 104.2(2) . . ?
N3 C2 H2 127.9 . . ?
C1 C2 H2 127.9 . . ?
N2 N3 C2 112.81(19) . . ?
N2 N3 C8 118.84(19) . . ?
C2 N3 C8 128.0(2) . . ?
N4 C3 C4 122.7(2) . . ?
N4 C3 C1 113.8(2) . . ?
C4 C3 C1 123.6(2) . . ?
C7 N4 C3 118.1(2) . . ?
C7 N4 Re1 124.32(15) . . ?
C3 N4 Re1 117.52(15) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C15 N5 C19 115.9(2) . . ?
C15 N5 Re1 122.12(16) . . ?
C19 N5 Re1 121.99(16) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C17 N6 C20 121.1(2) . . ?
C17 N6 C21 120.9(2) . . ?
C20 N6 C21 117.7(2) . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N4 C7 C6 122.0(2) . . ?
N4 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
N3 C8 C9 109.67(19) . . ?
N3 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N3 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C14 C9 C10 119.3(2) . . ?
C14 C9 C8 120.0(2) . . ?
C10 C9 C8 120.6(2) . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.3(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
N5 C15 C16 124.5(2) . . ?
N5 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
N6 C17 C16 123.0(2) . . ?
N6 C17 C18 122.0(2) . . ?
C16 C17 C18 115.0(2) . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
N5 C19 C18 123.7(2) . . ?
N5 C19 H19 118.1 . . ?
C18 C19 H19 118.1 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 H21A 109.5 . . ?
N6 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N6 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 Re1 177.7(2) . . ?
O2 C23 Re1 176.8(2) . . ?
O3 C24 Re1 179.3(2) . . ?
F2 C25 F3 107.2(2) . . ?
F2 C25 F1 107.6(2) . . ?
F3 C25 F1 107.5(2) . . ?
F2 C25 S1 111.1(2) . . ?
F3 C25 S1 111.58(19) . . ?
F1 C25 S1 111.66(18) . . ?

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
N2 N1 C1 C2 -0.1(3) . . . . ?
Re1 N1 C1 C2 -177.11(15) . . . . ?
N2 N1 C1 C3 178.5(2) . . . . ?
Re1 N1 C1 C3 1.5(3) . . . . ?
C1 N1 N2 N3 0.1(2) . . . . ?
Re1 N1 N2 N3 176.56(15) . . . . ?
N1 C1 C2 N3 0.0(3) . . . . ?
C3 C1 C2 N3 -178.2(3) . . . . ?
N1 N2 N3 C2 -0.1(3) . . . . ?
N1 N2 N3 C8 -173.66(19) . . . . ?
C1 C2 N3 N2 0.1(3) . . . . ?
C1 C2 N3 C8 172.9(2) . . . . ?
N1 C1 C3 N4 0.6(3) . . . . ?
C2 C1 C3 N4 178.7(3) . . . . ?
N1 C1 C3 C4 -178.0(2) . . . . ?
C2 C1 C3 C4 0.2(4) . . . . ?
C4 C3 N4 C7 -1.0(3) . . . . ?
C1 C3 N4 C7 -179.5(2) . . . . ?
C4 C3 N4 Re1 176.18(18) . . . . ?
C1 C3 N4 Re1 -2.4(3) . . . . ?
N4 C3 C4 C5 1.3(4) . . . . ?
C1 C3 C4 C5 179.7(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C3 N4 C7 C6 -0.4(3) . . . . ?
Re1 N4 C7 C6 -177.31(18) . . . . ?
C5 C6 C7 N4 1.4(4) . . . . ?
N2 N3 C8 C9 98.8(2) . . . . ?
C2 N3 C8 C9 -73.7(3) . . . . ?
N3 C8 C9 C14 -85.4(3) . . . . ?
N3 C8 C9 C10 93.0(3) . . . . ?
C14 C9 C10 C11 -0.5(4) . . . . ?
C8 C9 C10 C11 -178.9(2) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C9 -0.5(4) . . . . ?
C10 C9 C14 C13 0.5(4) . . . . ?
C8 C9 C14 C13 178.9(2) . . . . ?
C19 N5 C15 C16 -0.4(3) . . . . ?
Re1 N5 C15 C16 178.32(18) . . . . ?
N5 C15 C16 C17 -0.5(4) . . . . ?
C20 N6 C17 C16 -0.3(4) . . . . ?
C21 N6 C17 C16 172.8(2) . . . . ?
C20 N6 C17 C18 -179.5(2) . . . . ?
C21 N6 C17 C18 -6.4(4) . . . . ?
C15 C16 C17 N6 -177.9(2) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
N6 C17 C18 C19 177.9(2) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C15 N5 C19 C18 0.4(3) . . . . ?
Re1 N5 C19 C18 -178.30(18) . . . . ?
C17 C18 C19 N5 0.5(4) . . . . ?
O6 S1 C25 F2 177.17(18) . . . . ?
O5 S1 C25 F2 -61.7(2) . . . . ?
O4 S1 C25 F2 58.2(2) . . . . ?
O6 S1 C25 F3 57.6(2) . . . . ?
O5 S1 C25 F3 178.72(19) . . . . ?
O4 S1 C25 F3 -61.3(2) . . . . ?
O6 S1 C25 F1 -62.7(2) . . . . ?
O5 S1 C25 F1 58.4(2) . . . . ?
O4 S1 C25 F1 178.3(2) . . . . ?

_refine_diff_density_max         1.247
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.091

_diffrn_standards_decay_%        0.0

####################################################################### 
# 
# 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_6c
_database_code_depnum_ccdc_archive 'CCDC 1487875'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H18 N5 O5 Re, C H4 O'
_chemical_formula_sum            'C21 H22 N5 O6 Re'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         626.63

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.0901(17)
_cell_length_b                   9.3897(18)
_cell_length_c                   14.340(3)
_cell_angle_alpha                101.832(2)
_cell_angle_beta                 98.774(2)
_cell_angle_gamma                94.619(2)
_cell_volume                     1176.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.5
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    5.212
_shelx_estimated_absorpt_T_min   0.203
_shelx_estimated_absorpt_T_max   0.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.12
_exptl_absorpt_correction_T_max  0.23
_exptl_absorpt_process_details   
;
 Data were corrected for decay and absorption using the program TWINABS 
 Sheldrick, G. M. (1996). Program name. University of Göttingen, Germany
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22902
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.231
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5324
_reflns_number_gt                5070
_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       'APEX2 (Bruker AXS, 2008)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_refine_special_details          
;
 The data crystal proved to be a two component twin.  Cell_Now was used
 to determine the two orientation  matrices.  TWINABS was used to apply
 absorption correction and average the data.  The HKLF4 data was used
 for structure solution and all refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²+0.4616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5324
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0166
_refine_ls_wR_factor_ref         0.0432
_refine_ls_wR_factor_gt          0.0429
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Re1 Re 0.89993(2) 0.20276(2) 0.12749(2) 0.01129(4) Uani 1 1 d . . . . .
O1 O 1.01544(17) 0.39851(17) 0.22691(12) 0.0153(3) Uani 1 1 d . . . . .
N1 N 0.8267(2) 0.1969(2) 0.26263(14) 0.0130(4) Uani 1 1 d . . . . .
C1 C 0.8848(2) 0.3132(2) 0.33583(17) 0.0138(4) Uani 1 1 d . . . . .
O2 O 1.0374(2) 0.54032(18) 0.37548(13) 0.0208(4) Uani 1 1 d . . . . .
N2 N 0.7417(2) 0.1646(2) 0.38694(15) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.8303(3) 0.2927(2) 0.41663(18) 0.0161(5) Uani 1 1 d . . . . .
H2 H 0.8505 0.3549 0.4794 0.019 Uiso 1 1 calc R U . . .
O3 O 0.70172(19) -0.07088(18) 0.00484(14) 0.0228(4) Uani 1 1 d . . . . .
N3 N 0.7369(2) 0.1050(2) 0.29267(15) 0.0148(4) Uani 1 1 d . . . . .
C3 C 0.9878(2) 0.4282(2) 0.31313(18) 0.0148(4) Uani 1 1 d . . . . .
O4 O 1.0307(2) 0.26289(19) -0.04778(14) 0.0223(4) Uani 1 1 d . . . . .
N4 N 0.7236(2) 0.3473(2) 0.11643(15) 0.0143(4) Uani 1 1 d . . . . .
C4 C 0.6522(3) 0.0900(3) 0.44411(18) 0.0173(5) Uani 1 1 d . . . . .
H4A H 0.7164 0.0828 0.5049 0.021 Uiso 1 1 calc R U . . .
H4B H 0.6141 -0.0106 0.4071 0.021 Uiso 1 1 calc R U . . .
O5 O 1.1608(2) 0.0239(2) 0.17163(14) 0.0237(4) Uani 1 1 d . . . . .
N5 N 0.4092(2) 0.6485(2) 0.14642(17) 0.0193(4) Uani 1 1 d . . . . .
C5 C 0.5219(3) 0.1725(3) 0.46770(19) 0.0179(5) Uani 1 1 d . . . . .
O1M O 1.1146(2) 0.8174(2) 0.35010(17) 0.0289(4) Uani 1 1 d . . . . .
C6 C 0.3930(3) 0.1583(3) 0.3995(2) 0.0254(6) Uani 1 1 d . . . . .
H6 H 0.3863 0.0959 0.3374 0.030 Uiso 1 1 calc R U . . .
C1M C 0.9800(3) 0.8810(3) 0.3349(3) 0.0361(7) Uani 1 1 d . . . . .
H1M1 H 0.9089 0.8439 0.3717 0.054 Uiso 1 1 calc R U . . .
H1M2 H 0.9369 0.8555 0.2658 0.054 Uiso 1 1 calc R U . . .
H1M3 H 1.0007 0.9877 0.3565 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2737(3) 0.2345(3) 0.4214(2) 0.0329(7) Uani 1 1 d . . . . .
H7 H 0.1863 0.2252 0.3739 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2811(3) 0.3242(3) 0.5123(2) 0.0313(7) Uani 1 1 d . . . . .
H8 H 0.1986 0.3751 0.5275 0.038 Uiso 1 1 calc R U . . .
C9 C 0.4091(3) 0.3389(3) 0.5804(2) 0.0315(6) Uani 1 1 d . . . . .
H9 H 0.4153 0.4008 0.6425 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5299(3) 0.2633(3) 0.5584(2) 0.0245(5) Uani 1 1 d . . . . .
H10 H 0.6179 0.2740 0.6057 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7563(2) 0.4894(2) 0.11226(18) 0.0156(5) Uani 1 1 d . . . . .
H11 H 0.8545 0.5202 0.1036 0.019 Uiso 1 1 calc R U . . .
C12 C 0.6562(3) 0.5910(2) 0.11987(18) 0.0168(5) Uani 1 1 d . . . . .
H12 H 0.6856 0.6887 0.1158 0.020 Uiso 1 1 calc R U . . .
C13 C 0.5088(2) 0.5508(3) 0.13373(17) 0.0157(5) Uani 1 1 d . . . . .
C14 C 0.4743(2) 0.4009(3) 0.13391(19) 0.0180(5) Uani 1 1 d . . . . .
H14 H 0.3760 0.3655 0.1397 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5812(3) 0.3066(3) 0.12582(18) 0.0169(5) Uani 1 1 d . . . . .
H15 H 0.5540 0.2072 0.1268 0.020 Uiso 1 1 calc R U . . .
C16 C 0.4488(3) 0.8024(3) 0.1459(2) 0.0260(6) Uani 1 1 d . . . . .
H16A H 0.5319 0.8450 0.1990 0.039 Uiso 1 1 calc R U . . .
H16B H 0.3619 0.8561 0.1543 0.039 Uiso 1 1 calc R U . . .
H16C H 0.4791 0.8094 0.0841 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2607(3) 0.6028(3) 0.1640(2) 0.0251(6) Uani 1 1 d . . . . .
H17A H 0.2039 0.5360 0.1057 0.038 Uiso 1 1 calc R U . . .
H17B H 0.2079 0.6891 0.1803 0.038 Uiso 1 1 calc R U . . .
H17C H 0.2705 0.5527 0.2178 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7790(3) 0.0324(3) 0.04980(18) 0.0152(5) Uani 1 1 d . . . . .
C19 C 0.9795(3) 0.2397(2) 0.01713(18) 0.0158(5) Uani 1 1 d . . . . .
C20 C 1.0617(3) 0.0887(2) 0.15364(18) 0.0163(5) Uani 1 1 d . . . . .
H1M H 1.097(5) 0.730(5) 0.352(3) 0.069(14) 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
Re1 C18 1.903(2) . ?
Re1 C19 1.919(3) . ?
Re1 C20 1.923(2) . ?
Re1 N1 2.153(2) . ?
Re1 O1 2.1613(16) . ?
Re1 N4 2.1905(19) . ?
O1 C3 1.278(3) . ?
N1 N3 1.320(3) . ?
N1 C1 1.357(3) . ?
C1 C2 1.370(3) . ?
C1 C3 1.490(3) . ?
O2 C3 1.235(3) . ?
N2 C2 1.344(3) . ?
N2 N3 1.346(3) . ?
N2 C4 1.474(3) . ?
C2 H2 0.9500 . ?
O3 C18 1.159(3) . ?
O4 C19 1.153(3) . ?
N4 C15 1.354(3) . ?
N4 C11 1.359(3) . ?
C4 C5 1.510(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O5 C20 1.154(3) . ?
N5 C13 1.345(3) . ?
N5 C17 1.458(3) . ?
N5 C16 1.463(3) . ?
C5 C6 1.385(4) . ?
C5 C10 1.390(4) . ?
O1M C1M 1.411(3) . ?
O1M H1M 0.83(5) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.370(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.417(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.418(3) . ?
C14 C15 1.368(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C18 Re1 C19 90.72(10) . . ?
C18 Re1 C20 90.56(10) . . ?
C19 Re1 C20 89.09(10) . . ?
C18 Re1 N1 98.34(9) . . ?
C19 Re1 N1 170.69(8) . . ?
C20 Re1 N1 92.93(9) . . ?
C18 Re1 O1 172.75(8) . . ?
C19 Re1 O1 95.60(8) . . ?
C20 Re1 O1 93.10(8) . . ?
N1 Re1 O1 75.23(7) . . ?
C18 Re1 N4 94.95(8) . . ?
C19 Re1 N4 95.31(9) . . ?
C20 Re1 N4 172.90(8) . . ?
N1 Re1 N4 81.86(7) . . ?
O1 Re1 N4 80.95(7) . . ?
C3 O1 Re1 118.86(14) . . ?
N3 N1 C1 110.52(19) . . ?
N3 N1 Re1 134.98(15) . . ?
C1 N1 Re1 114.50(15) . . ?
N1 C1 C2 107.6(2) . . ?
N1 C1 C3 117.1(2) . . ?
C2 C1 C3 135.3(2) . . ?
C2 N2 N3 112.5(2) . . ?
C2 N2 C4 127.8(2) . . ?
N3 N2 C4 119.67(19) . . ?
N2 C2 C1 104.3(2) . . ?
N2 C2 H2 127.8 . . ?
C1 C2 H2 127.8 . . ?
N1 N3 N2 104.96(18) . . ?
O2 C3 O1 126.0(2) . . ?
O2 C3 C1 119.8(2) . . ?
O1 C3 C1 114.17(19) . . ?
C15 N4 C11 116.27(19) . . ?
C15 N4 Re1 122.15(15) . . ?
C11 N4 Re1 121.06(15) . . ?
N2 C4 C5 110.80(19) . . ?
N2 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C13 N5 C17 120.1(2) . . ?
C13 N5 C16 121.0(2) . . ?
C17 N5 C16 118.8(2) . . ?
C6 C5 C10 119.2(2) . . ?
C6 C5 C4 120.5(2) . . ?
C10 C5 C4 120.2(2) . . ?
C1M O1M H1M 111(3) . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.2(3) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N4 C11 C12 123.9(2) . . ?
N4 C11 H11 118.0 . . ?
C12 C11 H11 118.0 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
N5 C13 C12 122.2(2) . . ?
N5 C13 C14 122.5(2) . . ?
C12 C13 C14 115.3(2) . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N4 C15 C14 123.6(2) . . ?
N4 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 H17A 109.5 . . ?
N5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 Re1 177.5(2) . . ?
O4 C19 Re1 178.3(2) . . ?
O5 C20 Re1 177.9(2) . . ?

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
N3 N1 C1 C2 0.8(3) . . . . ?
Re1 N1 C1 C2 -179.01(14) . . . . ?
N3 N1 C1 C3 -179.41(18) . . . . ?
Re1 N1 C1 C3 0.8(2) . . . . ?
N3 N2 C2 C1 -0.5(3) . . . . ?
C4 N2 C2 C1 -179.0(2) . . . . ?
N1 C1 C2 N2 -0.1(2) . . . . ?
C3 C1 C2 N2 -179.9(2) . . . . ?
C1 N1 N3 N2 -1.0(2) . . . . ?
Re1 N1 N3 N2 178.66(15) . . . . ?
C2 N2 N3 N1 1.0(2) . . . . ?
C4 N2 N3 N1 179.61(19) . . . . ?
Re1 O1 C3 O2 -174.85(18) . . . . ?
Re1 O1 C3 C1 4.6(2) . . . . ?
N1 C1 C3 O2 175.9(2) . . . . ?
C2 C1 C3 O2 -4.3(4) . . . . ?
N1 C1 C3 O1 -3.6(3) . . . . ?
C2 C1 C3 O1 176.2(2) . . . . ?
C2 N2 C4 C5 70.0(3) . . . . ?
N3 N2 C4 C5 -108.4(2) . . . . ?
N2 C4 C5 C6 79.8(3) . . . . ?
N2 C4 C5 C10 -100.4(3) . . . . ?
C10 C5 C6 C7 0.4(4) . . . . ?
C4 C5 C6 C7 -179.9(3) . . . . ?
C5 C6 C7 C8 -1.0(5) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C6 C5 C10 C9 0.1(4) . . . . ?
C4 C5 C10 C9 -179.6(2) . . . . ?
C8 C9 C10 C5 0.0(5) . . . . ?
C15 N4 C11 C12 2.0(4) . . . . ?
Re1 N4 C11 C12 -169.84(19) . . . . ?
N4 C11 C12 C13 0.5(4) . . . . ?
C17 N5 C13 C12 -177.7(2) . . . . ?
C16 N5 C13 C12 0.4(4) . . . . ?
C17 N5 C13 C14 1.9(4) . . . . ?
C16 N5 C13 C14 179.9(2) . . . . ?
C11 C12 C13 N5 176.6(2) . . . . ?
C11 C12 C13 C14 -3.0(3) . . . . ?
N5 C13 C14 C15 -176.6(2) . . . . ?
C12 C13 C14 C15 3.0(4) . . . . ?
C11 N4 C15 C14 -2.0(4) . . . . ?
Re1 N4 C15 C14 169.77(19) . . . . ?
C13 C14 C15 N4 -0.6(4) . . . . ?

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
O1M H1M O2 0.83(5) 1.93(5) 2.751(3) 169(5) .

_refine_diff_density_max         1.290
_refine_diff_density_min         -1.186
_refine_diff_density_rms         0.091

_diffrn_standards_decay_%        0.0


####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1487878'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H19 N5 O3 Re, P F6, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C21 H23 F6 N5 O4 P Re'
_chemical_melting_point          ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         740.61

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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                   28.753(6)
_cell_length_b                   14.023(3)
_cell_length_c                   14.055(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.768(2)
_cell_angle_gamma                90
_cell_volume                     5186.0(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.4
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_F_000             2880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    4.829
_shelx_estimated_absorpt_T_min   0.196
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29174
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.548
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5878
_reflns_number_gt                5008
_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       'APEX2 (Bruker AXS, 2008)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'X-SEED, Barbour, 2001'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_refine_special_details          
;
 The MePim ligand is rotationally disordered and was modeled with suitable
 restraints. The solvent ethylacetate is also disordered about a 2-fold
 such that the stoiciometry is 0.5 ethylacetate to one complex.  The H 
 atoms of the solvent were not included in the model but were added 
 to the sum formula.  Residual electron density in the vicinity of the
 DMAP ligand and along the Re-C=O bonds may reflect additional orientational 
 disorder not included in the model.  Refinement in space group Cc does not 
 resolve the disorder, supporting refinement in the centrosymmetric setting.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0039P)²+82.8921P] 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         5878
_refine_ls_number_parameters     461
_refine_ls_number_restraints     465
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.125
_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 0.11567(2) 0.67962(2) 0.23529(2) 0.02573(7) Uani 1 1 d . U . . .
P1 P 0.17779(6) 1.14524(11) 0.22280(12) 0.0269(3) Uani 1 1 d . U . . .
F1 F 0.17682(16) 1.2554(3) 0.2532(3) 0.0499(11) Uani 1 1 d . U . . .
O1 O 0.0443(3) 0.5486(5) 0.0638(6) 0.107(3) Uani 1 1 d . U . . .
N1 N 0.1684(4) 0.7788(8) 0.3351(8) 0.020(2) Uani 0.741(10) 1 d . U P A 1
C1 C 0.1816(5) 0.8070(10) 0.4356(10) 0.025(2) Uani 0.741(10) 1 d . U P A 1
H1 H 0.1654 0.7882 0.4797 0.029 Uiso 0.741(10) 1 calc R U P A 1
N2 N 0.1568(3) 0.7388(7) 0.1454(7) 0.0253(18) Uani 0.741(10) 1 d . U P A 1
C2 C 0.2265(6) 0.8735(11) 0.4641(12) 0.024(3) Uani 0.741(10) 1 d . U P A 1
H2 H 0.2439 0.9072 0.5272 0.029 Uiso 0.741(10) 1 calc R U P A 1
N3 N 0.2353(3) 0.8731(5) 0.3788(6) 0.0251(16) Uani 0.741(10) 1 d . U P A 1
C3 C 0.2008(3) 0.8184(7) 0.3008(7) 0.0205(18) Uani 0.741(10) 1 d . U P A 1
C4 C 0.1946(3) 0.8030(6) 0.1936(8) 0.0220(17) Uani 0.741(10) 1 d . U P A 1
C5 C 0.2214(3) 0.8477(6) 0.1439(6) 0.0252(18) Uani 0.741(10) 1 d . U P A 1
H5 H 0.2467 0.8937 0.1794 0.030 Uiso 0.741(10) 1 calc R U P A 1
C6 C 0.2107(3) 0.8244(7) 0.0424(7) 0.0308(18) Uani 0.741(10) 1 d . U P A 1
H6 H 0.2286 0.8543 0.0067 0.037 Uiso 0.741(10) 1 calc R U P A 1
C7 C 0.1737(5) 0.7571(10) -0.0078(10) 0.028(3) Uani 0.741(10) 1 d . U P A 1
H7 H 0.1665 0.7390 -0.0774 0.034 Uiso 0.741(10) 1 calc R U P A 1
C8 C 0.1475(4) 0.7170(8) 0.0449(8) 0.028(2) Uani 0.741(10) 1 d . U P A 1
H8 H 0.1217 0.6717 0.0096 0.034 Uiso 0.741(10) 1 calc R U P A 1
C9 C 0.2796(3) 0.9243(6) 0.3796(7) 0.033(2) Uani 0.741(10) 1 d . U P A 1
H9A H 0.2813 0.9178 0.3117 0.049 Uiso 0.741(10) 1 calc R U P A 1
H9B H 0.2768 0.9920 0.3941 0.049 Uiso 0.741(10) 1 calc R U P A 1
H9C H 0.3105 0.8977 0.4336 0.049 Uiso 0.741(10) 1 calc R U P A 1
N1' N 0.1429(11) 0.720(2) 0.132(2) 0.027(4) Uani 0.259(10) 1 d . U P A 2
C1' C 0.1325(13) 0.696(3) 0.031(3) 0.032(6) Uani 0.259(10) 1 d . U P A 2
H1' H 0.1077 0.6502 -0.0084 0.038 Uiso 0.259(10) 1 calc R U P A 2
N2' N 0.1771(13) 0.786(3) 0.323(3) 0.022(4) Uani 0.259(10) 1 d . U P A 2
C2' C 0.1620(15) 0.745(3) -0.005(4) 0.030(7) Uani 0.259(10) 1 d . U P A 2
H2' H 0.1618 0.7415 -0.0724 0.036 Uiso 0.259(10) 1 calc R U P A 2
N3' N 0.1934(7) 0.8018(13) 0.0782(15) 0.024(4) Uani 0.259(10) 1 d . U P A 2
C3' C 0.1792(12) 0.779(2) 0.159(2) 0.024(5) Uani 0.259(10) 1 d . U P A 2
C4' C 0.2016(10) 0.822(2) 0.262(2) 0.023(5) Uani 0.259(10) 1 d . U P A 2
C5' C 0.2405(8) 0.8835(15) 0.3092(17) 0.021(4) Uani 0.259(10) 1 d . U P A 2
H5' H 0.2595 0.9069 0.2724 0.025 Uiso 0.259(10) 1 calc R U P A 2
C6' C 0.2528(10) 0.9122(19) 0.4094(19) 0.025(5) Uani 0.259(10) 1 d . U P A 2
H6' H 0.2785 0.9577 0.4445 0.030 Uiso 0.259(10) 1 calc R U P A 2
C7' C 0.2180(18) 0.859(4) 0.463(4) 0.024(8) Uani 0.259(10) 1 d . U P A 2
H7' H 0.2254 0.8688 0.5341 0.028 Uiso 0.259(10) 1 calc R U P A 2
C8' C 0.1904(14) 0.818(3) 0.422(3) 0.022(6) Uani 0.259(10) 1 d . U P A 2
H8' H 0.1692 0.7977 0.4550 0.026 Uiso 0.259(10) 1 calc R U P A 2
C9' C 0.2301(9) 0.8715(18) 0.0732(19) 0.027(5) Uani 0.259(10) 1 d . U P A 2
H9'1 H 0.2308 0.8695 0.0041 0.041 Uiso 0.259(10) 1 calc R U P A 2
H9'2 H 0.2202 0.9354 0.0862 0.041 Uiso 0.259(10) 1 calc R U P A 2
H9'3 H 0.2639 0.8562 0.1260 0.041 Uiso 0.259(10) 1 calc R U P A 2
O1S O 0.0833(4) 1.3884(9) 0.3169(9) 0.060(3) Uani 0.5 1 d . . P B 2
C1S C 0.0639(6) 1.3367(11) 0.1459(14) 0.057(4) Uani 0.5 1 d . U P C 1
O2S O 0.0056(3) 1.3624(6) 0.2101(6) 0.074(2) Uani 0.5 1 d . U P C 1
C2S C 0.0596(4) 1.3611(6) 0.2356(8) 0.066(2) Uani 0.5 1 d . U P . .
F2 F 0.13061(16) 1.1638(3) 0.1143(3) 0.0543(11) Uani 1 1 d . U . . .
O2 O 0.0706(3) 0.6156(5) 0.3866(7) 0.094(3) Uani 1 1 d . U . . .
F3 F 0.17768(17) 1.0367(3) 0.1917(3) 0.0581(12) Uani 1 1 d . U . . .
O3 O 0.18741(16) 0.5096(3) 0.3181(4) 0.0387(11) Uani 1 1 d . U . . .
F4 F 0.22466(16) 1.1286(3) 0.3303(3) 0.0509(11) Uani 1 1 d . U . . .
N4 N 0.06310(17) 0.8028(3) 0.1775(4) 0.0272(10) Uani 1 1 d . U . . .
F5 F 0.21556(17) 1.1708(4) 0.1700(3) 0.0639(13) Uani 1 1 d . U . . .
N5 N -0.04047(18) 1.0312(4) 0.0999(4) 0.0304(11) Uani 1 1 d . U . . .
F6 F 0.13869(19) 1.1229(4) 0.2738(4) 0.0657(14) Uani 1 1 d . U . . .
C10 C 0.0779(2) 0.8951(4) 0.1825(5) 0.0272(12) Uani 1 1 d . U . . .
H10 H 0.1133 0.9077 0.2065 0.033 Uiso 1 1 calc R U . . .
C11 C 0.0455(2) 0.9714(4) 0.1554(4) 0.0268(12) Uani 1 1 d . U . . .
H11 H 0.0588 1.0340 0.1598 0.032 Uiso 1 1 calc R U . . .
C12 C -0.0075(2) 0.9583(4) 0.1209(4) 0.0266(12) Uani 1 1 d . U . . .
C13 C -0.0232(2) 0.8617(4) 0.1104(5) 0.0285(13) Uani 1 1 d . U . . .
H13 H -0.0584 0.8466 0.0831 0.034 Uiso 1 1 calc R U . . .
C14 C 0.0121(2) 0.7898(4) 0.1394(5) 0.0299(13) Uani 1 1 d . U . . .
H14 H -0.0001 0.7261 0.1322 0.036 Uiso 1 1 calc R U . . .
C15 C -0.0236(3) 1.1299(5) 0.1065(5) 0.0362(15) Uani 1 1 d . U . . .
H15A H -0.0529 1.1725 0.0885 0.054 Uiso 1 1 calc R U . . .
H15B H 0.0009 1.1435 0.1775 0.054 Uiso 1 1 calc R U . . .
H15C H -0.0074 1.1400 0.0579 0.054 Uiso 1 1 calc R U . . .
C16 C -0.0954(2) 1.0148(5) 0.0600(5) 0.0346(14) Uani 1 1 d . U . . .
H16A H -0.1131 1.0762 0.0496 0.052 Uiso 1 1 calc R U . . .
H16B H -0.1067 0.9806 -0.0063 0.052 Uiso 1 1 calc R U . . .
H16C H -0.1032 0.9766 0.1102 0.052 Uiso 1 1 calc R U . . .
C17 C 0.0704(3) 0.5971(5) 0.1296(7) 0.057(2) Uani 1 1 d . U . . .
C18 C 0.0869(3) 0.6405(5) 0.3283(7) 0.0502(19) Uani 1 1 d . U . . .
C19 C 0.1609(2) 0.5740(4) 0.2853(5) 0.0277(12) Uani 1 1 d . U . . .
C3S C 0.0056(3) 1.3624(6) 0.2101(6) 0.074(2) Uani 0.5 1 d . U P . .
C2S' C 0.0596(4) 1.3611(6) 0.2356(8) 0.066(2) Uani 0.5 1 d . U P C 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 C18 1.889(7) . ?
Re1 C19 1.908(6) . ?
Re1 C17 1.918(8) . ?
Re1 N1' 1.98(3) . ?
Re1 N1 2.119(10) . ?
Re1 N2 2.210(9) . ?
Re1 N4 2.223(5) . ?
Re1 N2' 2.26(3) . ?
P1 F3 1.583(4) . ?
P1 F5 1.584(5) . ?
P1 F4 1.585(4) . ?
P1 F6 1.589(5) . ?
P1 F2 1.602(4) . ?
P1 F1 1.606(4) . ?
O1 C17 1.150(9) . ?
N1 C3 1.329(12) . ?
N1 C1 1.366(14) . ?
C1 C2 1.509(19) . ?
C1 H1 0.9500 . ?
N2 C4 1.363(11) . ?
N2 C8 1.363(13) . ?
C2 N3 1.323(17) . ?
C2 H2 0.9500 . ?
N3 C3 1.378(11) . ?
N3 C9 1.457(11) . ?
C3 C4 1.461(12) . ?
C4 C5 1.381(11) . ?
C5 C6 1.373(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.371(15) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N1' C3' 1.26(4) . ?
N1' C1' 1.37(4) . ?
C1' C2' 1.34(5) . ?
C1' H1' 0.9500 . ?
N2' C8' 1.37(5) . ?
N2' C4' 1.41(4) . ?
C2' N3' 1.40(4) . ?
C2' H2' 0.9500 . ?
N3' C3' 1.39(4) . ?
N3' C9' 1.46(3) . ?
C3' C4' 1.46(4) . ?
C4' C5' 1.35(3) . ?
C5' C6' 1.37(3) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.65(5) . ?
C6' H6' 0.9500 . ?
C7' C8' 0.96(6) . ?
C7' H7' 0.9500 . ?
C8' H8' 0.9500 . ?
C9' H9'1 0.9800 . ?
C9' H9'2 0.9800 . ?
C9' H9'3 0.9800 . ?
O2S O2S 1.286(15) 2 ?
O2S C3S 1.286(15) 2 ?
O2 C18 1.148(9) . ?
O3 C19 1.152(7) . ?
N4 C14 1.355(7) . ?
N4 C10 1.355(7) . ?
N5 C12 1.343(7) . ?
N5 C15 1.457(8) . ?
N5 C16 1.466(7) . ?
C10 C11 1.369(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.412(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(8) . ?
C13 C14 1.371(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C18 Re1 C19 86.8(3) . . ?
C18 Re1 C17 90.6(4) . . ?
C19 Re1 C17 88.0(3) . . ?
C18 Re1 N1' 177.4(8) . . ?
C19 Re1 N1' 94.4(9) . . ?
C17 Re1 N1' 87.1(8) . . ?
C18 Re1 N1 97.4(4) . . ?
C19 Re1 N1 93.8(4) . . ?
C17 Re1 N1 171.8(4) . . ?
C18 Re1 N2 171.6(4) . . ?
C19 Re1 N2 93.4(3) . . ?
C17 Re1 N2 97.8(4) . . ?
N1 Re1 N2 74.1(3) . . ?
C18 Re1 N4 93.2(2) . . ?
C19 Re1 N4 179.8(3) . . ?
C17 Re1 N4 92.1(3) . . ?
N1' Re1 N4 85.6(9) . . ?
N1 Re1 N4 86.1(3) . . ?
N2 Re1 N4 86.6(3) . . ?
C18 Re1 N2' 106.3(9) . . ?
C19 Re1 N2' 92.5(10) . . ?
C17 Re1 N2' 163.1(9) . . ?
N1' Re1 N2' 76.0(11) . . ?
N4 Re1 N2' 87.4(10) . . ?
F3 P1 F5 90.8(3) . . ?
F3 P1 F4 91.6(2) . . ?
F5 P1 F4 90.0(3) . . ?
F3 P1 F6 90.6(3) . . ?
F5 P1 F6 177.9(3) . . ?
F4 P1 F6 91.5(3) . . ?
F3 P1 F2 89.2(2) . . ?
F5 P1 F2 89.7(3) . . ?
F4 P1 F2 179.1(3) . . ?
F6 P1 F2 88.8(3) . . ?
F3 P1 F1 179.0(3) . . ?
F5 P1 F1 89.7(3) . . ?
F4 P1 F1 89.3(2) . . ?
F6 P1 F1 88.8(3) . . ?
F2 P1 F1 89.9(2) . . ?
C3 N1 C1 108.1(9) . . ?
C3 N1 Re1 117.0(7) . . ?
C1 N1 Re1 134.5(7) . . ?
N1 C1 C2 107.7(9) . . ?
N1 C1 H1 126.1 . . ?
C2 C1 H1 126.1 . . ?
C4 N2 C8 116.5(9) . . ?
C4 N2 Re1 117.9(6) . . ?
C8 N2 Re1 125.6(7) . . ?
N3 C2 C1 102.3(11) . . ?
N3 C2 H2 128.8 . . ?
C1 C2 H2 128.8 . . ?
C2 N3 C3 112.5(9) . . ?
C2 N3 C9 118.5(9) . . ?
C3 N3 C9 128.9(8) . . ?
N1 C3 N3 109.3(8) . . ?
N1 C3 C4 120.0(8) . . ?
N3 C3 C4 130.6(9) . . ?
N2 C4 C5 123.0(9) . . ?
N2 C4 C3 110.5(7) . . ?
C5 C4 C3 126.4(10) . . ?
C6 C5 C4 118.7(9) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 119.7(10) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 118.8(11) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
N2 C8 C7 123.2(10) . . ?
N2 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3' N1' C1' 106(3) . . ?
C3' N1' Re1 119(2) . . ?
C1' N1' Re1 134(2) . . ?
C2' C1' N1' 111(3) . . ?
C2' C1' H1' 124.6 . . ?
N1' C1' H1' 124.6 . . ?
C8' N2' C4' 120(3) . . ?
C8' N2' Re1 128(2) . . ?
C4' N2' Re1 113(2) . . ?
C1' C2' N3' 106(4) . . ?
C1' C2' H2' 127.0 . . ?
N3' C2' H2' 127.0 . . ?
C3' N3' C2' 104(3) . . ?
C3' N3' C9' 131(2) . . ?
C2' N3' C9' 125(3) . . ?
N1' C3' N3' 113(3) . . ?
N1' C3' C4' 124(3) . . ?
N3' C3' C4' 124(3) . . ?
C5' C4' N2' 117(3) . . ?
C5' C4' C3' 135(3) . . ?
N2' C4' C3' 109(2) . . ?
C4' C5' C6' 121(2) . . ?
C4' C5' H5' 119.6 . . ?
C6' C5' H5' 119.6 . . ?
C5' C6' C7' 112(3) . . ?
C5' C6' H6' 123.8 . . ?
C7' C6' H6' 123.8 . . ?
C8' C7' C6' 120(5) . . ?
C8' C7' H7' 119.8 . . ?
C6' C7' H7' 119.8 . . ?
C7' C8' N2' 129(4) . . ?
C7' C8' H8' 115.4 . . ?
N2' C8' H8' 115.4 . . ?
N3' C9' H9'1 109.5 . . ?
N3' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
N3' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
O2S O2S C3S 0.0(6) 2 2 ?
C14 N4 C10 114.6(5) . . ?
C14 N4 Re1 120.5(4) . . ?
C10 N4 Re1 124.7(4) . . ?
C12 N5 C15 121.4(5) . . ?
C12 N5 C16 121.4(5) . . ?
C15 N5 C16 116.9(5) . . ?
N4 C10 C11 124.5(5) . . ?
N4 C10 H10 117.7 . . ?
C11 C10 H10 117.7 . . ?
C10 C11 C12 120.9(6) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N5 C12 C11 123.0(6) . . ?
N5 C12 C13 122.6(5) . . ?
C11 C12 C13 114.4(5) . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N4 C14 C13 124.9(6) . . ?
N4 C14 H14 117.6 . . ?
C13 C14 H14 117.6 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 Re1 177.4(10) . . ?
O2 C18 Re1 178.1(7) . . ?
O3 C19 Re1 177.4(6) . . ?

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
C3 N1 C1 C2 1.6(16) . . . . ?
Re1 N1 C1 C2 173.9(11) . . . . ?
N1 C1 C2 N3 -2.4(18) . . . . ?
C1 C2 N3 C3 2.4(16) . . . . ?
C1 C2 N3 C9 -175.0(10) . . . . ?
C1 N1 C3 N3 -0.1(12) . . . . ?
Re1 N1 C3 N3 -174.0(7) . . . . ?
C1 N1 C3 C4 -177.9(9) . . . . ?
Re1 N1 C3 C4 8.2(12) . . . . ?
C2 N3 C3 N1 -1.6(13) . . . . ?
C9 N3 C3 N1 175.4(9) . . . . ?
C2 N3 C3 C4 175.8(11) . . . . ?
C9 N3 C3 C4 -7.1(15) . . . . ?
C8 N2 C4 C5 2.6(13) . . . . ?
Re1 N2 C4 C5 -177.2(6) . . . . ?
C8 N2 C4 C3 -179.1(8) . . . . ?
Re1 N2 C4 C3 1.1(9) . . . . ?
N1 C3 C4 N2 -6.0(12) . . . . ?
N3 C3 C4 N2 176.7(9) . . . . ?
N1 C3 C4 C5 172.2(9) . . . . ?
N3 C3 C4 C5 -5.0(14) . . . . ?
N2 C4 C5 C6 -2.1(12) . . . . ?
C3 C4 C5 C6 179.8(8) . . . . ?
C4 C5 C6 C7 -0.1(14) . . . . ?
C5 C6 C7 C8 1.7(17) . . . . ?
C4 N2 C8 C7 -0.9(15) . . . . ?
Re1 N2 C8 C7 178.9(9) . . . . ?
C6 C7 C8 N2 -1.2(18) . . . . ?
C3' N1' C1' C2' -3(4) . . . . ?
Re1 N1' C1' C2' 180(3) . . . . ?
N1' C1' C2' N3' 1(4) . . . . ?
C1' C2' N3' C3' 1(4) . . . . ?
C1' C2' N3' C9' -177(3) . . . . ?
C1' N1' C3' N3' 3(4) . . . . ?
Re1 N1' C3' N3' -178.5(17) . . . . ?
C1' N1' C3' C4' 180(3) . . . . ?
Re1 N1' C3' C4' -2(4) . . . . ?
C2' N3' C3' N1' -3(3) . . . . ?
C9' N3' C3' N1' 175(2) . . . . ?
C2' N3' C3' C4' -179(3) . . . . ?
C9' N3' C3' C4' -2(4) . . . . ?
C8' N2' C4' C5' 5(5) . . . . ?
Re1 N2' C4' C5' -177(2) . . . . ?
C8' N2' C4' C3' -178(3) . . . . ?
Re1 N2' C4' C3' 0(3) . . . . ?
N1' C3' C4' C5' 178(3) . . . . ?
N3' C3' C4' C5' -6(5) . . . . ?
N1' C3' C4' N2' 2(4) . . . . ?
N3' C3' C4' N2' 177(3) . . . . ?
N2' C4' C5' C6' -4(4) . . . . ?
C3' C4' C5' C6' -180(3) . . . . ?
C4' C5' C6' C7' 4(4) . . . . ?
C5' C6' C7' C8' -6(8) . . . . ?
C6' C7' C8' N2' 9(11) . . . . ?
C4' N2' C8' C7' -9(9) . . . . ?
Re1 N2' C8' C7' 174(7) . . . . ?
C14 N4 C10 C11 2.1(9) . . . . ?
Re1 N4 C10 C11 -173.9(5) . . . . ?
N4 C10 C11 C12 1.2(10) . . . . ?
C15 N5 C12 C11 3.2(9) . . . . ?
C16 N5 C12 C11 177.3(6) . . . . ?
C15 N5 C12 C13 -176.9(6) . . . . ?
C16 N5 C12 C13 -2.7(9) . . . . ?
C10 C11 C12 N5 175.6(6) . . . . ?
C10 C11 C12 C13 -4.3(9) . . . . ?
N5 C12 C13 C14 -175.6(6) . . . . ?
C11 C12 C13 C14 4.3(9) . . . . ?
C10 N4 C14 C13 -2.1(9) . . . . ?
Re1 N4 C14 C13 174.0(5) . . . . ?
C12 C13 C14 N4 -1.2(10) . . . . ?

_refine_diff_density_max         2.915
_refine_diff_density_min         -3.174
_refine_diff_density_rms         0.142

_diffrn_standards_decay_%        0.0

