# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_C2
_database_code_depnum_ccdc_archive 'CCDC 1871495'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl3 F2 N2 O3 Re'
_chemical_formula_sum            'C19 H12 Cl3 F2 N2 O3 Re'
_chemical_formula_weight         646.86

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'
Cl Cl 0.1484 0.1585 '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                   7.1480(2)
_cell_length_b                   9.2830(2)
_cell_length_c                   17.0670(6)
_cell_angle_alpha                105.7160(9)
_cell_angle_beta                 98.7670(10)
_cell_angle_gamma                95.9490(14)
_cell_volume                     1064.83(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2450
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      29.99

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    6.123
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            15263
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.935
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4816
_reflns_number_gt                4330
_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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0576P)²+0.2694P] 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         4816
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.02297(2) -0.12139(2) -0.23992(2) 0.02311(9) Uani 1 1 d . . . . .
Cl1 Cl 0.13052(19) -0.12599(14) -0.37213(8) 0.0280(3) Uani 1 1 d . . . . .
F1 F 0.4785(5) 0.3738(4) -0.2185(2) 0.0479(9) Uani 1 1 d . . . . .
N1 N 0.0087(6) 0.1136(5) -0.2390(3) 0.0245(9) Uani 1 1 d . . . . .
O1 O 0.4397(6) -0.0909(5) -0.1535(3) 0.0485(11) Uani 1 1 d . . . . .
C1 C 0.2938(8) 0.2600(5) -0.1413(3) 0.0280(11) Uani 1 1 d . . . . .
Cl2 Cl 0.8394(2) 0.4560(2) -0.10238(11) 0.0596(5) Uani 1 1 d . . . . .
F2 F -0.6799(4) -0.4811(4) -0.3568(2) 0.0410(8) Uani 1 1 d . . . . .
O2 O 0.0274(7) -0.4527(5) -0.2466(3) 0.0512(12) Uani 1 1 d . . . . .
C2 C 0.4683(8) 0.3330(6) -0.1481(3) 0.0323(12) Uani 1 1 d . . . . .
N2 N -0.2709(6) -0.1367(5) -0.3069(3) 0.0243(9) Uani 1 1 d . . . . .
Cl3 Cl -0.6990(2) -0.80892(17) -0.42451(11) 0.0492(4) Uani 1 1 d . . . . .
O3 O -0.1216(7) -0.0992(5) -0.0778(3) 0.0494(11) Uani 1 1 d . . . . .
C3 C 0.6304(8) 0.3642(7) -0.0882(4) 0.0377(13) Uani 1 1 d . . . . .
C4 C 0.6208(9) 0.3236(7) -0.0164(4) 0.0440(15) Uani 1 1 d . . . . .
H4A H 0.729298 0.342764 0.024838 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4473(10) 0.2538(7) -0.0062(4) 0.0453(15) Uani 1 1 d . . . . .
H5A H 0.439398 0.228130 0.042354 0.054 Uiso 1 1 calc R U . . .
C6 C 0.2878(9) 0.2229(7) -0.0681(4) 0.0362(13) Uani 1 1 d . . . . .
H6A H 0.173183 0.175981 -0.060614 0.043 Uiso 1 1 calc R U . . .
C7 C 0.1259(8) 0.2382(6) -0.2064(3) 0.0300(11) Uani 1 1 d . . . . .
H7A H 0.101891 0.320459 -0.225580 0.036 Uiso 1 1 calc R U . . .
C8 C -0.1619(8) 0.1221(6) -0.2988(3) 0.0314(12) Uani 1 1 d . . . . .
H8A H -0.138222 0.091427 -0.354981 0.038 Uiso 1 1 calc R U . . .
H8B H -0.190544 0.224865 -0.286653 0.038 Uiso 1 1 calc R U . . .
C9 C -0.3280(8) 0.0160(6) -0.2895(4) 0.0317(12) Uani 1 1 d . . . . .
H9A H -0.354069 0.048196 -0.233796 0.038 Uiso 1 1 calc R U . . .
H9B H -0.442526 0.015252 -0.328401 0.038 Uiso 1 1 calc R U . . .
C10 C -0.4025(8) -0.2467(6) -0.3510(3) 0.0282(11) Uani 1 1 d . . . . .
H10A H -0.524617 -0.223355 -0.364200 0.034 Uiso 1 1 calc R U . . .
C11 C -0.3763(7) -0.4063(5) -0.3825(3) 0.0267(10) Uani 1 1 d . . . . .
C12 C -0.2168(8) -0.4490(6) -0.4161(3) 0.0313(12) Uani 1 1 d . . . . .
H12A H -0.118210 -0.374784 -0.415595 0.038 Uiso 1 1 calc R U . . .
C13 C -0.2035(8) -0.6005(6) -0.4503(3) 0.0348(12) Uani 1 1 d . . . . .
H13A H -0.095269 -0.626982 -0.471401 0.042 Uiso 1 1 calc R U . . .
C14 C -0.3493(8) -0.7114(6) -0.4530(3) 0.0323(12) Uani 1 1 d . . . . .
H14A H -0.339539 -0.812724 -0.475772 0.039 Uiso 1 1 calc R U . . .
C15 C -0.5120(8) -0.6720(6) -0.4218(3) 0.0315(12) Uani 1 1 d . . . . .
C16 C -0.5225(8) -0.5195(6) -0.3865(3) 0.0294(11) Uani 1 1 d . . . . .
C17 C 0.2828(8) -0.0972(6) -0.1843(4) 0.0326(12) Uani 1 1 d . . . . .
C18 C 0.0230(9) -0.3313(6) -0.2477(4) 0.0322(12) Uani 1 1 d . . . . .
C19 C -0.0688(8) -0.1079(6) -0.1380(4) 0.0335(12) 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 C17 1.914(6) . ?
Re1 C18 1.917(5) . ?
Re1 C19 1.928(6) . ?
Re1 N1 2.190(4) . ?
Re1 N2 2.204(4) . ?
Re1 Cl1 2.4834(13) . ?
F1 C2 1.365(6) . ?
N1 C7 1.288(7) . ?
N1 C8 1.489(6) . ?
O1 C17 1.152(7) . ?
C1 C6 1.389(8) . ?
C1 C2 1.392(7) . ?
C1 C7 1.462(7) . ?
Cl2 C3 1.725(6) . ?
F2 C16 1.344(6) . ?
O2 C18 1.136(7) . ?
C2 C3 1.371(8) . ?
N2 C10 1.290(7) . ?
N2 C9 1.480(6) . ?
Cl3 C15 1.733(6) . ?
O3 C19 1.133(7) . ?
C3 C4 1.386(9) . ?
C4 C5 1.395(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.378(9) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.518(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.475(7) . ?
C10 H10A 0.9300 . ?
C11 C16 1.383(7) . ?
C11 C12 1.399(7) . ?
C12 C13 1.388(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.373(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.394(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.395(7) . ?

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
C17 Re1 C18 84.4(2) . . ?
C17 Re1 C19 91.3(2) . . ?
C18 Re1 C19 85.3(2) . . ?
C17 Re1 N1 99.0(2) . . ?
C18 Re1 N1 176.1(2) . . ?
C19 Re1 N1 96.58(19) . . ?
C17 Re1 N2 176.31(18) . . ?
C18 Re1 N2 98.8(2) . . ?
C19 Re1 N2 90.8(2) . . ?
N1 Re1 N2 77.76(16) . . ?
C17 Re1 Cl1 90.71(17) . . ?
C18 Re1 Cl1 97.70(17) . . ?
C19 Re1 Cl1 176.53(16) . . ?
N1 Re1 Cl1 80.30(12) . . ?
N2 Re1 Cl1 87.05(11) . . ?
C7 N1 C8 115.2(5) . . ?
C7 N1 Re1 133.5(4) . . ?
C8 N1 Re1 110.6(3) . . ?
C6 C1 C2 116.5(5) . . ?
C6 C1 C7 123.6(5) . . ?
C2 C1 C7 119.7(5) . . ?
F1 C2 C3 118.5(5) . . ?
F1 C2 C1 118.1(5) . . ?
C3 C2 C1 123.4(5) . . ?
C10 N2 C9 115.6(4) . . ?
C10 N2 Re1 134.6(3) . . ?
C9 N2 Re1 109.6(3) . . ?
C2 C3 C4 118.8(5) . . ?
C2 C3 Cl2 119.8(5) . . ?
C4 C3 Cl2 121.4(5) . . ?
C3 C4 C5 119.6(6) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C6 C5 C4 120.0(6) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 121.7(6) . . ?
C5 C6 H6A 119.2 . . ?
C1 C6 H6A 119.2 . . ?
N1 C7 C1 124.8(5) . . ?
N1 C7 H7A 117.6 . . ?
C1 C7 H7A 117.6 . . ?
N1 C8 C9 107.1(4) . . ?
N1 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
N1 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
N2 C9 C8 106.8(4) . . ?
N2 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
N2 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
N2 C10 C11 125.7(5) . . ?
N2 C10 H10A 117.1 . . ?
C11 C10 H10A 117.1 . . ?
C16 C11 C12 117.9(5) . . ?
C16 C11 C10 119.1(5) . . ?
C12 C11 C10 122.7(5) . . ?
C13 C12 C11 120.9(5) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C14 C13 C12 120.3(5) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 119.2(5) . . ?
C14 C15 Cl3 121.2(4) . . ?
C16 C15 Cl3 119.6(4) . . ?
F2 C16 C11 119.0(5) . . ?
F2 C16 C15 119.3(5) . . ?
C11 C16 C15 121.6(5) . . ?
O1 C17 Re1 176.1(5) . . ?
O2 C18 Re1 175.3(6) . . ?
O3 C19 Re1 179.5(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
C6 C1 C2 F1 -178.8(5) . . . . ?
C7 C1 C2 F1 -3.9(7) . . . . ?
C6 C1 C2 C3 2.1(8) . . . . ?
C7 C1 C2 C3 176.9(5) . . . . ?
F1 C2 C3 C4 179.7(5) . . . . ?
C1 C2 C3 C4 -1.1(9) . . . . ?
F1 C2 C3 Cl2 1.1(7) . . . . ?
C1 C2 C3 Cl2 -179.7(4) . . . . ?
C2 C3 C4 C5 -0.6(9) . . . . ?
Cl2 C3 C4 C5 178.0(5) . . . . ?
C3 C4 C5 C6 1.3(10) . . . . ?
C4 C5 C6 C1 -0.2(10) . . . . ?
C2 C1 C6 C5 -1.4(8) . . . . ?
C7 C1 C6 C5 -176.0(5) . . . . ?
C8 N1 C7 C1 174.7(5) . . . . ?
Re1 N1 C7 C1 -15.7(9) . . . . ?
C6 C1 C7 N1 -51.4(8) . . . . ?
C2 C1 C7 N1 134.2(6) . . . . ?
C7 N1 C8 C9 -145.6(5) . . . . ?
Re1 N1 C8 C9 42.5(5) . . . . ?
C10 N2 C9 C8 -138.5(5) . . . . ?
Re1 N2 C9 C8 46.1(5) . . . . ?
N1 C8 C9 N2 -58.5(5) . . . . ?
C9 N2 C10 C11 174.3(5) . . . . ?
Re1 N2 C10 C11 -11.7(8) . . . . ?
N2 C10 C11 C16 144.0(5) . . . . ?
N2 C10 C11 C12 -42.3(8) . . . . ?
C16 C11 C12 C13 -1.8(8) . . . . ?
C10 C11 C12 C13 -175.6(5) . . . . ?
C11 C12 C13 C14 1.3(9) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?
C13 C14 C15 C16 -1.2(8) . . . . ?
C13 C14 C15 Cl3 179.8(4) . . . . ?
C12 C11 C16 F2 -178.1(5) . . . . ?
C10 C11 C16 F2 -4.1(7) . . . . ?
C12 C11 C16 C15 0.9(8) . . . . ?
C10 C11 C16 C15 174.8(5) . . . . ?
C14 C15 C16 F2 179.5(5) . . . . ?
Cl3 C15 C16 F2 -1.4(7) . . . . ?
C14 C15 C16 C11 0.6(8) . . . . ?
Cl3 C15 C16 C11 179.7(4) . . . . ?

_refine_diff_density_max         2.146
_refine_diff_density_min         -3.184
_refine_diff_density_rms         0.222

####################################################################### 
# 
# 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_C5
_database_code_depnum_ccdc_archive 'CCDC 1871496'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Br Cl4 N2 O3 Re'
_chemical_formula_sum            'C19 H12 Br Cl4 N2 O3 Re'
_chemical_formula_weight         724.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   7.1653(3)
_cell_length_b                   10.1441(5)
_cell_length_c                   16.1968(10)
_cell_angle_alpha                86.971(4)
_cell_angle_beta                 82.270(4)
_cell_angle_gamma                71.257(4)
_cell_volume                     1104.65(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3467
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      28.94

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.177
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    7.817
_shelx_estimated_absorpt_T_min   0.574
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            9299
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.424
_diffrn_reflns_theta_max         29.262
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5040
_reflns_number_gt                4565
_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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0204P)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         5040
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0691
_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
C1 C 0.2095(7) 0.2341(5) 0.6509(3) 0.0203(11) Uani 1 1 d . . . . .
C2 C 0.0884(7) 0.1731(5) 0.7046(3) 0.0214(11) Uani 1 1 d . . . . .
H2 H 0.000125 0.137816 0.683251 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1009(8) 0.1658(5) 0.7894(3) 0.0246(12) Uani 1 1 d . . . . .
C4 C 0.2254(8) 0.2210(6) 0.8232(3) 0.0273(13) Uani 1 1 d . . . . .
H4 H 0.232738 0.215739 0.880249 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3396(8) 0.2848(6) 0.7700(3) 0.0241(12) Uani 1 1 d . . . . .
C6 C 0.3341(7) 0.2926(5) 0.6845(3) 0.0206(11) Uani 1 1 d . . . . .
H6 H 0.412033 0.336071 0.650124 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1820(7) 0.2444(5) 0.5615(3) 0.0196(11) Uani 1 1 d . . . . .
H7 H 0.057788 0.244937 0.550386 0.024 Uiso 1 1 calc R U . . .
C8 C 0.5131(6) 0.2345(5) 0.5026(3) 0.0160(10) Uani 1 1 d . . . . .
H8A H 0.552346 0.188562 0.554504 0.019 Uiso 1 1 calc R U . . .
H8B H 0.535652 0.324011 0.499740 0.019 Uiso 1 1 calc R U . . .
C9 C 0.6314(7) 0.1453(5) 0.4287(3) 0.0175(11) Uani 1 1 d . . . . .
H9A H 0.769502 0.141083 0.424834 0.021 Uiso 1 1 calc R U . . .
H9B H 0.625395 0.051304 0.437089 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6811(7) 0.1870(5) 0.2845(3) 0.0180(11) Uani 1 1 d . . . . .
H10 H 0.814388 0.155691 0.292644 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6345(7) 0.2134(5) 0.1980(3) 0.0190(11) Uani 1 1 d . . . . .
C12 C 0.5011(7) 0.1593(5) 0.1694(3) 0.0214(11) Uani 1 1 d . . . . .
H12 H 0.437436 0.107378 0.204678 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4643(7) 0.1838(5) 0.0877(3) 0.0203(11) Uani 1 1 d . . . . .
C14 C 0.5613(8) 0.2587(6) 0.0329(3) 0.0262(13) Uani 1 1 d . . . . .
H14 H 0.535446 0.274230 -0.022138 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6956(7) 0.3087(6) 0.0624(3) 0.0230(12) Uani 1 1 d . . . . .
C16 C 0.7392(7) 0.2867(5) 0.1439(3) 0.0207(11) Uani 1 1 d . . . . .
H16 H 0.833994 0.318946 0.162270 0.025 Uiso 1 1 calc R U . . .
C17 C -0.0506(7) 0.3881(5) 0.4042(3) 0.0201(11) Uani 1 1 d . . . . .
C18 C 0.1656(7) 0.3683(5) 0.2601(3) 0.0189(11) Uani 1 1 d . . . . .
C19 C 0.2654(7) 0.4878(5) 0.3800(3) 0.0152(10) Uani 1 1 d . . . . .
Br1 Br 0.20198(7) 0.05814(5) 0.36363(3) 0.02116(12) Uani 1 1 d . . . . .
Cl1 Cl -0.0424(2) 0.08495(16) 0.85408(9) 0.0376(4) Uani 1 1 d . . . . .
Cl2 Cl 0.4935(2) 0.36053(17) 0.81066(9) 0.0388(4) Uani 1 1 d . . . . .
Cl3 Cl 0.2885(2) 0.12338(18) 0.05221(9) 0.0373(4) Uani 1 1 d . . . . .
Cl4 Cl 0.8140(2) 0.40518(16) -0.00416(9) 0.0380(4) Uani 1 1 d . . . . .
N1 N 0.3025(5) 0.2528(4) 0.4976(2) 0.0140(8) Uani 1 1 d . . . . .
N2 N 0.5513(5) 0.2038(4) 0.3498(3) 0.0154(9) Uani 1 1 d . . . . .
O1 O -0.2187(5) 0.4345(4) 0.4238(2) 0.0249(8) Uani 1 1 d . . . . .
O2 O 0.1147(5) 0.4138(4) 0.1975(2) 0.0312(10) Uani 1 1 d . . . . .
O3 O 0.2844(5) 0.5910(4) 0.3850(2) 0.0252(9) Uani 1 1 d . . . . .
Re1 Re 0.22820(3) 0.30881(2) 0.37121(2) 0.01325(7) 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
C1 C6 1.396(7) . ?
C1 C2 1.406(7) . ?
C1 C7 1.481(7) . ?
C2 C3 1.384(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(7) . ?
C3 Cl1 1.728(6) . ?
C4 C5 1.386(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(7) . ?
C5 Cl2 1.742(5) . ?
C6 H6 0.9300 . ?
C7 N1 1.273(6) . ?
C7 H7 0.9300 . ?
C8 N1 1.473(6) . ?
C8 C9 1.522(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.488(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.290(6) . ?
C10 C11 1.474(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(7) . ?
C11 C16 1.412(7) . ?
C12 C13 1.378(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(7) . ?
C13 Cl3 1.738(5) . ?
C14 C15 1.369(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(7) . ?
C15 Cl4 1.737(6) . ?
C16 H16 0.9300 . ?
C17 O1 1.150(6) . ?
C17 Re1 1.910(5) . ?
C18 O2 1.146(6) . ?
C18 Re1 1.932(5) . ?
C19 O3 1.107(6) . ?
C19 Re1 1.933(6) . ?
Br1 Re1 2.6196(6) . ?
N1 Re1 2.185(4) . ?
N2 Re1 2.203(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.3(5) . . ?
C6 C1 C7 123.4(5) . . ?
C2 C1 C7 117.0(5) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 Cl1 119.3(4) . . ?
C2 C3 Cl1 119.2(4) . . ?
C3 C4 C5 118.2(5) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 122.2(5) . . ?
C4 C5 Cl2 119.6(4) . . ?
C6 C5 Cl2 118.1(4) . . ?
C5 C6 C1 118.9(5) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C1 129.8(5) . . ?
N1 C7 H7 115.1 . . ?
C1 C7 H7 115.1 . . ?
N1 C8 C9 106.5(4) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
N2 C9 C8 110.8(4) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C11 125.1(4) . . ?
N2 C10 H10 117.5 . . ?
C11 C10 H10 117.5 . . ?
C12 C11 C16 121.0(5) . . ?
C12 C11 C10 120.4(5) . . ?
C16 C11 C10 118.5(5) . . ?
C13 C12 C11 118.8(5) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 121.8(5) . . ?
C12 C13 Cl3 119.3(4) . . ?
C14 C13 Cl3 118.9(4) . . ?
C15 C14 C13 118.2(5) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 122.5(5) . . ?
C14 C15 Cl4 118.9(4) . . ?
C16 C15 Cl4 118.6(4) . . ?
C15 C16 C11 117.7(5) . . ?
C15 C16 H16 121.2 . . ?
C11 C16 H16 121.2 . . ?
O1 C17 Re1 179.3(5) . . ?
O2 C18 Re1 173.7(4) . . ?
O3 C19 Re1 179.2(4) . . ?
C7 N1 C8 122.3(4) . . ?
C7 N1 Re1 126.3(3) . . ?
C8 N1 Re1 111.2(3) . . ?
C10 N2 C9 115.5(4) . . ?
C10 N2 Re1 133.2(3) . . ?
C9 N2 Re1 111.3(3) . . ?
C17 Re1 C18 85.2(2) . . ?
C17 Re1 C19 90.8(2) . . ?
C18 Re1 C19 85.9(2) . . ?
C17 Re1 N1 95.04(18) . . ?
C18 Re1 N1 176.69(18) . . ?
C19 Re1 N1 90.83(17) . . ?
C17 Re1 N2 172.32(19) . . ?
C18 Re1 N2 102.25(18) . . ?
C19 Re1 N2 91.57(16) . . ?
N1 Re1 N2 77.64(14) . . ?
C17 Re1 Br1 92.40(15) . . ?
C18 Re1 Br1 96.92(15) . . ?
C19 Re1 Br1 175.89(13) . . ?
N1 Re1 Br1 86.37(10) . . ?
N2 Re1 Br1 84.90(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 C1 C2 C3 -3.1(7) . . . . ?
C7 C1 C2 C3 -177.2(4) . . . . ?
C1 C2 C3 C4 2.1(8) . . . . ?
C1 C2 C3 Cl1 -177.6(4) . . . . ?
C2 C3 C4 C5 -0.1(8) . . . . ?
Cl1 C3 C4 C5 179.7(4) . . . . ?
C3 C4 C5 C6 -0.9(8) . . . . ?
C3 C4 C5 Cl2 178.1(4) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
Cl2 C5 C6 C1 -179.1(4) . . . . ?
C2 C1 C6 C5 2.1(7) . . . . ?
C7 C1 C6 C5 175.8(5) . . . . ?
C6 C1 C7 N1 30.4(8) . . . . ?
C2 C1 C7 N1 -155.8(5) . . . . ?
N1 C8 C9 N2 51.3(5) . . . . ?
N2 C10 C11 C12 -49.2(7) . . . . ?
N2 C10 C11 C16 135.1(5) . . . . ?
C16 C11 C12 C13 -3.1(7) . . . . ?
C10 C11 C12 C13 -178.7(4) . . . . ?
C11 C12 C13 C14 1.5(7) . . . . ?
C11 C12 C13 Cl3 -177.1(3) . . . . ?
C12 C13 C14 C15 -0.2(8) . . . . ?
Cl3 C13 C14 C15 178.3(4) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C13 C14 C15 Cl4 -178.7(4) . . . . ?
C14 C15 C16 C11 -2.1(8) . . . . ?
Cl4 C15 C16 C11 177.2(3) . . . . ?
C12 C11 C16 C15 3.4(7) . . . . ?
C10 C11 C16 C15 179.0(4) . . . . ?
C1 C7 N1 C8 8.4(8) . . . . ?
C1 C7 N1 Re1 -166.9(4) . . . . ?
C9 C8 N1 C7 137.6(5) . . . . ?
C9 C8 N1 Re1 -46.4(5) . . . . ?
C11 C10 N2 C9 168.7(5) . . . . ?
C11 C10 N2 Re1 -13.5(8) . . . . ?
C8 C9 N2 C10 146.5(4) . . . . ?
C8 C9 N2 Re1 -31.8(5) . . . . ?

_refine_diff_density_max         1.334
_refine_diff_density_min         -1.758
_refine_diff_density_rms         0.185

####################################################################### 
# 
# 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_C7
_database_code_depnum_ccdc_archive 'CCDC 1871501'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Br2 Cl F2 N2 O3 Re'
_chemical_formula_sum            'C19 H12 Br2 Cl F2 N2 O3 Re'
_chemical_formula_weight         735.78

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.3756(4)
_cell_length_b                   8.8914(4)
_cell_length_c                   16.9636(10)
_cell_angle_alpha                98.004(4)
_cell_angle_beta                 90.442(5)
_cell_angle_gamma                105.113(4)
_cell_volume                     1062.4(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4347
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      26.98

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.300
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    9.647
_shelx_estimated_absorpt_T_min   0.445
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            15534
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.357
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4862
_reflns_number_gt                3870
_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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0603P)²+7.6658P] 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         4862
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.007
_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 0.08053(6) 0.4887(2) 0.24582(8) 0.0325(3) Uani 0.927(6) 1 d . . P A 1
Br2 Br -0.30122(13) -0.25985(11) 0.00666(7) 0.0441(3) Uani 1 1 d . . . . .
Br1 Br 0.82726(19) 0.77334(18) 0.54704(9) 0.0766(4) Uani 1 1 d . . . . .
Cl1 Cl 0.2380(3) 0.5694(3) 0.12368(16) 0.0473(6) Uani 1 1 d . . . . .
F1 F 0.6088(12) 0.9917(10) 0.3114(6) 0.099(3) Uani 1 1 d . . . . .
C13 C -0.1983(13) 0.0743(12) 0.0182(6) 0.044(2) Uani 1 1 d . . . . .
H13 H -0.124757 0.057127 -0.024694 0.052 Uiso 1 1 calc R U . . .
C8 C -0.0308(15) 0.7893(12) 0.2235(7) 0.054(3) Uani 1 1 d . . . . .
H8A H -0.047348 0.890621 0.246711 0.064 Uiso 1 1 calc R U . . .
H8B H 0.014230 0.797488 0.170268 0.064 Uiso 1 1 calc R U . . .
F2 F -0.5408(9) 0.1445(7) 0.2002(4) 0.0570(16) Uani 1 1 d . . . . .
C4 C 0.6410(16) 0.8020(13) 0.4794(7) 0.053(3) Uani 1 1 d . . . . .
O3 O -0.1163(15) 0.4040(16) 0.3937(8) 0.106(4) Uani 1 1 d . . . . .
C15 C -0.4268(12) -0.0325(11) 0.1112(6) 0.039(2) Uani 1 1 d . . . . .
H15 H -0.503143 -0.118042 0.131415 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6958(19) 0.8931(14) 0.4187(8) 0.067(3) Uani 1 1 d . . . . .
H3 H 0.821897 0.942005 0.413112 0.080 Uiso 1 1 calc R U . . .
O2 O 0.0403(11) 0.1357(9) 0.1921(7) 0.079(3) Uani 1 1 d . . . . .
O1 O 0.4551(10) 0.4729(10) 0.3205(5) 0.060(2) Uani 1 1 d . . . . .
N2 N -0.1825(11) 0.5101(9) 0.1932(5) 0.0394(18) Uani 1 1 d . . . . .
C9 C -0.2117(15) 0.6657(11) 0.2202(7) 0.052(3) Uani 1 1 d . . . . .
H9A H -0.263175 0.667242 0.272692 0.062 Uiso 1 1 calc R U . . .
H9B H -0.301104 0.686929 0.183949 0.062 Uiso 1 1 calc R U . . .
C14 C -0.3112(12) -0.0530(10) 0.0502(6) 0.036(2) Uani 1 1 d . . . . .
C10 C -0.3168(13) 0.4107(11) 0.1489(6) 0.041(2) Uani 1 1 d . . . . .
H10 H -0.423899 0.442318 0.137954 0.049 Uiso 1 1 calc R U . . .
C16 C -0.4255(12) 0.1197(11) 0.1416(6) 0.038(2) Uani 1 1 d . . . . .
C2 C 0.5587(17) 0.9090(13) 0.3672(8) 0.058(3) Uani 1 1 d . . . . .
N1 N 0.1073(11) 0.7422(9) 0.2739(5) 0.045(2) Uani 1 1 d . . . . .
C5 C 0.4579(18) 0.7275(16) 0.4890(7) 0.068(3) Uani 1 1 d . . . . .
H5 H 0.424877 0.664796 0.528854 0.081 Uiso 1 1 calc R U . . .
C11 C -0.3106(11) 0.2523(11) 0.1149(6) 0.037(2) Uani 1 1 d . . . . .
C7 C 0.2297(16) 0.8576(13) 0.3184(7) 0.055(3) Uani 1 1 d . . . . .
H7 H 0.227688 0.960114 0.313688 0.066 Uiso 1 1 calc R U . . .
C12 C -0.1972(14) 0.2263(11) 0.0511(7) 0.046(2) Uani 1 1 d . . . . .
H12 H -0.120790 0.311623 0.030745 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3185(16) 0.7485(14) 0.4362(7) 0.060(3) Uani 1 1 d . . . . .
H6 H 0.192618 0.702031 0.443563 0.072 Uiso 1 1 calc R U . . .
C17 C 0.3165(14) 0.4834(11) 0.2933(6) 0.044(2) Uani 1 1 d . . . . .
C1 C 0.3648(15) 0.8369(12) 0.3732(7) 0.050(3) Uani 1 1 d . . . . .
C19 C -0.0512(17) 0.4356(14) 0.3415(10) 0.065(4) Uani 1 1 d . . . . .
C18 C 0.0527(13) 0.2684(14) 0.2099(8) 0.055(3) Uani 1 1 d . . . . .
Re1A Re 0.0806(8) 0.421(2) 0.2240(7) 0.023(2) Uani 0.073(6) 1 d . . P A 2


_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 C17 1.927(11) . ?
Re1 C18 1.925(13) . ?
Re1 C19 1.949(16) . ?
Re1 N2 2.193(8) . ?
Re1 N1 2.194(8) . ?
Re1 Cl1 2.485(3) . ?
Br2 C14 1.904(9) . ?
Br1 C4 1.873(11) . ?
Cl1 Re1A 2.415(6) . ?
F1 C2 1.278(14) . ?
C13 C12 1.387(14) . ?
C13 C14 1.398(12) . ?
C13 H13 0.9300 . ?
C8 C9 1.486(14) . ?
C8 N1 1.501(13) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
F2 C16 1.346(11) . ?
C4 C5 1.363(16) . ?
C4 C3 1.395(16) . ?
O3 C19 1.048(17) . ?
C15 C16 1.377(13) . ?
C15 C14 1.369(13) . ?
C15 H15 0.9300 . ?
C3 C2 1.378(17) . ?
C3 H3 0.9300 . ?
O2 C18 1.156(14) . ?
O2 Re1A 2.460(19) . ?
O1 C17 1.149(12) . ?
N2 C10 1.294(12) . ?
N2 C9 1.466(12) . ?
N2 Re1A 2.358(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.458(14) . ?
C10 H10 0.9300 . ?
C16 C11 1.395(12) . ?
C2 C1 1.417(15) . ?
N1 C7 1.314(14) . ?
C5 C6 1.423(17) . ?
C5 H5 0.9300 . ?
C11 C12 1.404(14) . ?
C7 C1 1.421(16) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C6 C1 1.405(16) . ?
C6 H6 0.9300 . ?
C17 Re1A 2.001(12) . ?
C19 Re1A 2.23(2) . ?
C18 Re1A 1.31(2) . ?

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
C17 Re1 C18 84.5(4) . . ?
C17 Re1 C19 91.7(4) . . ?
C18 Re1 C19 89.8(5) . . ?
C17 Re1 N2 176.6(4) . . ?
C18 Re1 N2 98.9(4) . . ?
C19 Re1 N2 89.0(4) . . ?
C17 Re1 N1 98.9(4) . . ?
C18 Re1 N1 174.1(4) . . ?
C19 Re1 N1 94.9(5) . . ?
N2 Re1 N1 77.7(3) . . ?
C17 Re1 Cl1 90.8(3) . . ?
C18 Re1 Cl1 93.0(4) . . ?
C19 Re1 Cl1 176.4(4) . . ?
N2 Re1 Cl1 88.3(2) . . ?
N1 Re1 Cl1 82.2(2) . . ?
C12 C13 C14 119.3(9) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C9 C8 N1 107.3(8) . . ?
C9 C8 H8A 110.3 . . ?
N1 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
N1 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
C5 C4 C3 122.4(11) . . ?
C5 C4 Br1 118.8(9) . . ?
C3 C4 Br1 118.7(9) . . ?
C16 C15 C14 117.4(8) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C2 C3 C4 118.4(11) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C18 O2 Re1A 3.4(7) . . ?
C10 N2 C9 116.4(8) . . ?
C10 N2 Re1 132.5(7) . . ?
C9 N2 Re1 110.9(6) . . ?
C10 N2 Re1A 116.8(7) . . ?
C9 N2 Re1A 126.8(7) . . ?
N2 C9 C8 110.2(9) . . ?
N2 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C15 C14 C13 121.9(9) . . ?
C15 C14 Br2 119.8(7) . . ?
C13 C14 Br2 118.2(8) . . ?
N2 C10 C11 124.0(8) . . ?
N2 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
F2 C16 C15 119.2(8) . . ?
F2 C16 C11 117.1(8) . . ?
C15 C16 C11 123.7(9) . . ?
F1 C2 C3 118.5(11) . . ?
F1 C2 C1 118.6(11) . . ?
C3 C2 C1 122.9(11) . . ?
C7 N1 C8 116.2(9) . . ?
C7 N1 Re1 132.8(7) . . ?
C8 N1 Re1 110.6(6) . . ?
C4 C5 C6 118.1(11) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C16 C11 C12 117.1(9) . . ?
C16 C11 C10 121.2(9) . . ?
C12 C11 C10 121.5(8) . . ?
N1 C7 C1 124.7(10) . . ?
N1 C7 H7 117.7 . . ?
C1 C7 H7 117.7 . . ?
C13 C12 C11 120.4(8) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C1 C6 C5 122.2(11) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
O1 C17 Re1 176.8(9) . . ?
O1 C17 Re1A 157.8(11) . . ?
C6 C1 C2 115.8(11) . . ?
C6 C1 C7 123.7(10) . . ?
C2 C1 C7 120.4(11) . . ?
O3 C19 Re1 176.8(12) . . ?
O3 C19 Re1A 161.8(14) . . ?
O2 C18 Re1A 173.6(13) . . ?
O2 C18 Re1 176.4(11) . . ?
C18 Re1A C17 100.9(7) . . ?
C18 Re1A C19 97.9(7) . . ?
C17 Re1A C19 82.1(6) . . ?
C18 Re1A N2 114.4(6) . . ?
C17 Re1A N2 141.6(10) . . ?
C19 Re1A N2 78.7(5) . . ?
C18 Re1A Cl1 116.7(10) . . ?
C17 Re1A Cl1 91.1(4) . . ?
C19 Re1A Cl1 145.4(9) . . ?
N2 Re1A Cl1 86.3(3) . . ?
C18 Re1A O2 3.0(6) . . ?
C17 Re1A O2 100.4(6) . . ?
C19 Re1A O2 100.8(5) . . ?
N2 Re1A O2 115.6(5) . . ?
Cl1 Re1A O2 113.8(7) . . ?

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 C4 C3 C2 1(2) . . . . ?
Br1 C4 C3 C2 177.6(10) . . . . ?
C10 N2 C9 C8 -144.6(10) . . . . ?
Re1 N2 C9 C8 39.8(11) . . . . ?
Re1A N2 C9 C8 36.6(13) . . . . ?
N1 C8 C9 N2 -53.8(12) . . . . ?
C16 C15 C14 C13 -1.3(14) . . . . ?
C16 C15 C14 Br2 178.6(7) . . . . ?
C12 C13 C14 C15 2.6(15) . . . . ?
C12 C13 C14 Br2 -177.3(8) . . . . ?
C9 N2 C10 C11 178.4(9) . . . . ?
Re1 N2 C10 C11 -7.1(15) . . . . ?
Re1A N2 C10 C11 -2.6(13) . . . . ?
C14 C15 C16 F2 178.3(8) . . . . ?
C14 C15 C16 C11 -1.6(14) . . . . ?
C4 C3 C2 F1 -179.6(12) . . . . ?
C4 C3 C2 C1 0(2) . . . . ?
C9 C8 N1 C7 -145.0(10) . . . . ?
C9 C8 N1 Re1 41.8(11) . . . . ?
C3 C4 C5 C6 -2(2) . . . . ?
Br1 C4 C5 C6 -178.9(9) . . . . ?
F2 C16 C11 C12 -176.9(8) . . . . ?
C15 C16 C11 C12 3.0(14) . . . . ?
F2 C16 C11 C10 -0.5(13) . . . . ?
C15 C16 C11 C10 179.4(9) . . . . ?
N2 C10 C11 C16 110.5(11) . . . . ?
N2 C10 C11 C12 -73.3(13) . . . . ?
C8 N1 C7 C1 176.5(11) . . . . ?
Re1 N1 C7 C1 -12.2(18) . . . . ?
C14 C13 C12 C11 -1.1(15) . . . . ?
C16 C11 C12 C13 -1.5(14) . . . . ?
C10 C11 C12 C13 -177.9(9) . . . . ?
C4 C5 C6 C1 3(2) . . . . ?
C5 C6 C1 C2 -2.2(18) . . . . ?
C5 C6 C1 C7 178.7(12) . . . . ?
F1 C2 C1 C6 -179.6(11) . . . . ?
C3 C2 C1 C6 0.8(18) . . . . ?
F1 C2 C1 C7 -0.4(18) . . . . ?
C3 C2 C1 C7 180.0(12) . . . . ?
N1 C7 C1 C6 -56.8(17) . . . . ?
N1 C7 C1 C2 124.1(13) . . . . ?

_refine_diff_density_max         3.252
_refine_diff_density_min         -1.709
_refine_diff_density_rms         0.190

####################################################################### 
# 
# 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_C3
_database_code_depnum_ccdc_archive 'CCDC 1871498'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Br Cl2 F2 N2 O3 Re'
_chemical_formula_sum            'C19 H12 Br Cl2 F2 N2 O3 Re'
_chemical_formula_weight         691.32

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'
Cl Cl 0.1484 0.1585 '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'
Br Br -0.2901 2.4595 '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                   7.3600(1)
_cell_length_b                   9.2080(3)
_cell_length_c                   16.5900(5)
_cell_angle_alpha                101.508(1)
_cell_angle_beta                 94.970(2)
_cell_angle_gamma                98.653(2)
_cell_volume                     1081.25(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3457
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      26.45

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    7.754
_shelx_estimated_absorpt_T_min   0.306
_shelx_estimated_absorpt_T_max   0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            15816
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.948
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4939
_reflns_number_gt                4568
_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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0532P)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         4939
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_restrained_S_all      1.261
_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
C1 C 0.3290(6) 0.4409(6) 0.8657(3) 0.0294(10) Uani 1 1 d . . . . .
C2 C 0.4976(7) 0.4149(6) 0.9003(3) 0.0298(10) Uani 1 1 d . . . . .
H2 H 0.604726 0.485301 0.904605 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5039(7) 0.2838(6) 0.9281(3) 0.0328(11) Uani 1 1 d . . . . .
C4 C 0.3436(8) 0.1813(6) 0.9228(3) 0.0368(11) Uani 1 1 d . . . . .
C5 C 0.1757(8) 0.2040(7) 0.8912(4) 0.0401(13) Uani 1 1 d . . . . .
H5 H 0.069395 0.133158 0.887827 0.048 Uiso 1 1 calc R U . . .
C6 C 0.1685(7) 0.3386(6) 0.8638(3) 0.0344(11) Uani 1 1 d . . . . .
H6 H 0.055050 0.359148 0.844123 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3104(6) 0.5792(6) 0.8364(3) 0.0293(10) Uani 1 1 d . . . . .
H7 H 0.203188 0.618286 0.846382 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3712(6) 0.7909(5) 0.7801(3) 0.0295(10) Uani 1 1 d . . . . .
H8A H 0.284446 0.826607 0.816983 0.035 Uiso 1 1 calc R U . . .
H8B H 0.312597 0.771920 0.723462 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5465(6) 0.9073(5) 0.7923(3) 0.0300(10) Uani 1 1 d . . . . .
H9A H 0.517837 1.000549 0.779961 0.036 Uiso 1 1 calc R U . . .
H9B H 0.603926 0.927625 0.849163 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7659(6) 0.9363(5) 0.6994(3) 0.0304(10) Uani 1 1 d . . . . .
H10 H 0.755660 1.037309 0.714832 0.036 Uiso 1 1 calc R U . . .
C11 C 0.8876(6) 0.8967(5) 0.6364(3) 0.0283(10) Uani 1 1 d . . . . .
C12 C 1.0653(7) 0.9801(6) 0.6454(3) 0.0328(10) Uani 1 1 d . . . . .
H12 H 1.105049 1.057694 0.691707 0.039 Uiso 1 1 calc R U . . .
C13 C 1.1820(7) 0.9487(7) 0.5866(3) 0.0373(12) Uani 1 1 d . . . . .
C14 C 1.1204(7) 0.8331(7) 0.5171(3) 0.0381(12) Uani 1 1 d . . . . .
C15 C 0.9443(8) 0.7544(7) 0.5052(3) 0.0412(12) Uani 1 1 d . . . . .
H15 H 0.903192 0.680432 0.457436 0.049 Uiso 1 1 calc R U . . .
C16 C 0.8273(7) 0.7858(6) 0.5651(3) 0.0319(10) Uani 1 1 d . . . . .
H16 H 0.707312 0.732114 0.557489 0.038 Uiso 1 1 calc R U . . .
C17 C 0.6779(7) 0.4040(6) 0.7497(3) 0.0322(11) Uani 1 1 d . . . . .
C18 C 0.8920(7) 0.5824(5) 0.6861(3) 0.0295(10) Uani 1 1 d . . . . .
C19 C 0.5191(7) 0.5287(6) 0.6363(3) 0.0310(10) Uani 1 1 d . . . . .
N1 N 0.6722(5) 0.8448(4) 0.7353(2) 0.0235(8) Uani 1 1 d . . . . .
N2 N 0.4248(5) 0.6516(4) 0.7987(2) 0.0237(8) Uani 1 1 d . . . . .
O1 O 0.6915(6) 0.2818(4) 0.7531(2) 0.0432(9) Uani 1 1 d . . . . .
O2 O 1.0237(5) 0.5585(4) 0.6558(2) 0.0402(9) Uani 1 1 d . . . . .
O3 O 0.4222(6) 0.4789(5) 0.5765(2) 0.0488(11) Uani 1 1 d . . . . .
Cl1 Cl 0.71162(18) 0.24728(16) 0.96903(8) 0.0430(3) Uani 1 1 d . . . . .
Cl2 Cl 1.40366(18) 1.0506(2) 0.59767(10) 0.0563(4) Uani 1 1 d . . . . .
F1 F 0.3528(5) 0.0542(4) 0.9513(2) 0.0471(8) Uani 1 1 d . . . . .
F2 F 1.2346(4) 0.8032(4) 0.4590(2) 0.0573(10) Uani 1 1 d . . . . .
Br1 Br 0.87436(7) 0.72719(6) 0.88157(3) 0.03397(13) Uani 1 1 d . . . . .
Re1 Re 0.67388(2) 0.60638(2) 0.73855(2) 0.02196(8) 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
C1 C6 1.389(7) . ?
C1 C2 1.395(6) . ?
C1 C7 1.471(6) . ?
C2 C3 1.381(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(7) . ?
C3 Cl1 1.726(5) . ?
C4 F1 1.355(6) . ?
C4 C5 1.362(8) . ?
C5 C6 1.409(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.278(6) . ?
C7 H7 0.9300 . ?
C8 N2 1.478(6) . ?
C8 C9 1.519(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.475(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.280(6) . ?
C10 C11 1.462(7) . ?
C10 H10 0.9300 . ?
C11 C16 1.389(7) . ?
C11 C12 1.393(7) . ?
C12 C13 1.371(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(8) . ?
C13 Cl2 1.731(5) . ?
C14 F2 1.348(6) . ?
C14 C15 1.364(7) . ?
C15 C16 1.386(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O1 1.156(6) . ?
C17 Re1 1.913(5) . ?
C18 O2 1.159(6) . ?
C18 Re1 1.912(5) . ?
C19 O3 1.141(6) . ?
C19 Re1 1.903(5) . ?
N1 Re1 2.208(4) . ?
N2 Re1 2.216(4) . ?
Br1 Re1 2.6251(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.6(5) . . ?
C6 C1 C7 117.7(4) . . ?
C2 C1 C7 122.6(4) . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 Cl1 119.8(4) . . ?
C2 C3 Cl1 120.3(4) . . ?
F1 C4 C5 118.6(5) . . ?
F1 C4 C3 118.9(5) . . ?
C5 C4 C3 122.5(5) . . ?
C4 C5 C6 117.7(5) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 120.8(5) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N2 C7 C1 127.4(4) . . ?
N2 C7 H7 116.3 . . ?
C1 C7 H7 116.3 . . ?
N2 C8 C9 107.4(4) . . ?
N2 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
N2 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
N1 C9 C8 107.2(4) . . ?
N1 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
N1 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
N1 C10 C11 125.9(4) . . ?
N1 C10 H10 117.0 . . ?
C11 C10 H10 117.0 . . ?
C16 C11 C12 119.0(4) . . ?
C16 C11 C10 122.0(4) . . ?
C12 C11 C10 118.8(4) . . ?
C13 C12 C11 120.5(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.3(4) . . ?
C12 C13 Cl2 120.9(4) . . ?
C14 C13 Cl2 119.8(4) . . ?
F2 C14 C15 119.5(5) . . ?
F2 C14 C13 119.3(5) . . ?
C15 C14 C13 121.1(5) . . ?
C14 C15 C16 119.3(5) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O1 C17 Re1 174.8(4) . . ?
O2 C18 Re1 175.3(4) . . ?
O3 C19 Re1 177.5(4) . . ?
C10 N1 C9 116.9(4) . . ?
C10 N1 Re1 132.8(3) . . ?
C9 N1 Re1 110.1(3) . . ?
C7 N2 C8 114.9(4) . . ?
C7 N2 Re1 135.2(3) . . ?
C8 N2 Re1 109.3(3) . . ?
C19 Re1 C18 91.7(2) . . ?
C19 Re1 C17 88.6(2) . . ?
C18 Re1 C17 83.6(2) . . ?
C19 Re1 N1 94.93(18) . . ?
C18 Re1 N1 98.20(17) . . ?
C17 Re1 N1 175.96(16) . . ?
C19 Re1 N2 88.86(18) . . ?
C18 Re1 N2 175.81(16) . . ?
C17 Re1 N2 100.58(18) . . ?
N1 Re1 N2 77.61(14) . . ?
C19 Re1 Br1 176.31(15) . . ?
C18 Re1 Br1 90.94(15) . . ?
C17 Re1 Br1 94.22(15) . . ?
N1 Re1 Br1 82.16(10) . . ?
N2 Re1 Br1 88.31(10) . . ?

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 C1 C2 C3 3.4(7) . . . . ?
C7 C1 C2 C3 178.7(4) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C1 C2 C3 Cl1 178.6(4) . . . . ?
C2 C3 C4 F1 -179.3(4) . . . . ?
Cl1 C3 C4 F1 0.9(6) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
Cl1 C3 C4 C5 179.9(4) . . . . ?
F1 C4 C5 C6 178.5(5) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C2 C1 C6 C5 -4.3(7) . . . . ?
C7 C1 C6 C5 -179.8(5) . . . . ?
C4 C5 C6 C1 2.8(8) . . . . ?
C6 C1 C7 N2 -146.3(5) . . . . ?
C2 C1 C7 N2 38.4(7) . . . . ?
N2 C8 C9 N1 59.2(5) . . . . ?
N1 C10 C11 C16 53.3(7) . . . . ?
N1 C10 C11 C12 -131.3(5) . . . . ?
C16 C11 C12 C13 -2.9(7) . . . . ?
C10 C11 C12 C13 -178.5(4) . . . . ?
C11 C12 C13 C14 0.6(8) . . . . ?
C11 C12 C13 Cl2 -179.5(4) . . . . ?
C12 C13 C14 F2 179.4(5) . . . . ?
Cl2 C13 C14 F2 -0.5(7) . . . . ?
C12 C13 C14 C15 2.2(8) . . . . ?
Cl2 C13 C14 C15 -177.7(4) . . . . ?
F2 C14 C15 C16 -179.9(5) . . . . ?
C13 C14 C15 C16 -2.7(9) . . . . ?
C14 C15 C16 C11 0.4(8) . . . . ?
C12 C11 C16 C15 2.4(8) . . . . ?
C10 C11 C16 C15 177.8(5) . . . . ?
C11 C10 N1 C9 -175.2(4) . . . . ?
C11 C10 N1 Re1 10.9(7) . . . . ?
C8 C9 N1 C10 141.0(4) . . . . ?
C8 C9 N1 Re1 -43.8(4) . . . . ?
C1 C7 N2 C8 -177.5(4) . . . . ?
C1 C7 N2 Re1 12.0(8) . . . . ?
C9 C8 N2 C7 142.2(4) . . . . ?
C9 C8 N2 Re1 -44.9(4) . . . . ?

_refine_diff_density_max         1.475
_refine_diff_density_min         -2.375
_refine_diff_density_rms         0.385

####################################################################### 
# 
# 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_C6
_database_code_depnum_ccdc_archive 'CCDC 1871497'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl5 N2 O3 Re'
_chemical_formula_sum            'C19 H12 Cl5 N2 O3 Re'
_chemical_formula_weight         679.76

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'
Cl Cl 0.1484 0.1585 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.1210(1)
_cell_length_b                   33.7880(7)
_cell_length_c                   9.4780(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.0240(8)
_cell_angle_gamma                90
_cell_volume                     2267.86(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4356
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      26.98

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.971
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            13793
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.238
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5118
_reflns_number_gt                3739
_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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0104P)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         5118
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0532
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.83712(2) 0.12532(2) 0.37131(2) 0.01929(7) Uani 1 1 d . . . . .
Cl1 Cl 0.68712(13) 0.05996(3) 0.31366(11) 0.0241(3) Uani 1 1 d . . . . .
O1 O 0.8065(4) 0.11989(11) 0.6911(3) 0.0393(9) Uani 1 1 d . . . . .
N1 N 1.1137(4) 0.09655(11) 0.3566(3) 0.0184(8) Uani 1 1 d . . . . .
C1 C 1.1972(5) 0.06266(14) 0.5825(4) 0.0203(10) Uani 1 1 d . . . . .
Cl2 Cl 0.79809(15) 0.00374(4) 0.75986(12) 0.0327(3) Uani 1 1 d . . . . .
C2 C 1.0308(5) 0.04334(13) 0.6042(4) 0.0219(11) Uani 1 1 d . . . . .
H2A H 0.934529 0.040980 0.530358 0.026 Uiso 1 1 calc R U . . .
N2 N 0.8597(4) 0.12465(11) 0.1407(3) 0.0198(8) Uani 1 1 d . . . . .
O2 O 0.4582(4) 0.16882(10) 0.3719(3) 0.0375(9) Uani 1 1 d . . . . .
Cl3 Cl 1.48532(14) 0.05529(4) 0.96969(11) 0.0318(3) Uani 1 1 d . . . . .
C3 C 1.0089(5) 0.02772(14) 0.7350(5) 0.0222(11) Uani 1 1 d . . . . .
O3 O 1.0238(5) 0.20588(11) 0.4277(4) 0.0492(10) Uani 1 1 d . . . . .
Cl4 Cl 0.09550(17) 0.19460(5) -0.11905(18) 0.0695(5) Uani 1 1 d . . . . .
C4 C 1.1465(6) 0.03045(14) 0.8475(5) 0.0246(11) Uani 1 1 d . . . . .
H4A H 1.129171 0.019607 0.935352 0.029 Uiso 1 1 calc R U . . .
Cl5 Cl 0.61742(19) 0.28287(5) 0.19053(15) 0.0534(4) Uani 1 1 d . . . . .
C5 C 1.3129(5) 0.05007(15) 0.8252(5) 0.0254(11) Uani 1 1 d . . . . .
C6 C 1.3413(5) 0.06572(14) 0.6949(4) 0.0223(11) Uani 1 1 d . . . . .
H6A H 1.454639 0.078157 0.681537 0.027 Uiso 1 1 calc R U . . .
C7 C 1.2321(5) 0.07802(14) 0.4444(4) 0.0236(11) Uani 1 1 d . . . . .
H7A H 1.352222 0.074015 0.416843 0.028 Uiso 1 1 calc R U . . .
C8 C 1.1771(5) 0.10437(14) 0.2147(4) 0.0242(11) Uani 1 1 d . . . . .
H8A H 1.280986 0.087003 0.197987 0.029 Uiso 1 1 calc R U . . .
H8B H 1.218789 0.131581 0.208228 0.029 Uiso 1 1 calc R U . . .
C9 C 1.0081(5) 0.09654(14) 0.1069(5) 0.0258(11) Uani 1 1 d . . . . .
H9A H 1.040857 0.100919 0.011358 0.031 Uiso 1 1 calc R U . . .
H9B H 0.965006 0.069459 0.114332 0.031 Uiso 1 1 calc R U . . .
C10 C 0.7637(5) 0.14043(14) 0.0342(5) 0.0264(11) Uani 1 1 d . . . . .
H10A H 0.782955 0.131069 -0.055380 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6247(6) 0.17238(15) 0.0425(4) 0.0246(11) Uani 1 1 d . . . . .
C12 C 0.4452(6) 0.16817(15) -0.0296(5) 0.0317(12) Uani 1 1 d . . . . .
H12A H 0.410417 0.144997 -0.078536 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3188(6) 0.19966(17) -0.0266(6) 0.0388(14) Uani 1 1 d . . . . .
C14 C 0.3672(6) 0.23461(16) 0.0417(5) 0.0396(14) Uani 1 1 d . . . . .
H14A H 0.280184 0.255079 0.043334 0.047 Uiso 1 1 calc R U . . .
C15 C 0.5491(6) 0.23860(16) 0.1080(5) 0.0333(12) Uani 1 1 d . . . . .
C16 C 0.6764(6) 0.20785(16) 0.1104(5) 0.0313(12) Uani 1 1 d . . . . .
H16A H 0.797006 0.210799 0.157301 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8246(5) 0.12089(14) 0.5705(5) 0.0244(11) Uani 1 1 d . . . . .
C18 C 0.5990(6) 0.15211(14) 0.3674(4) 0.0250(11) Uani 1 1 d . . . . .
C19 C 0.9568(6) 0.17517(17) 0.4069(5) 0.0302(12) 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 C19 1.902(6) . ?
Re1 C17 1.905(5) . ?
Re1 C18 1.919(5) . ?
Re1 N2 2.209(3) . ?
Re1 N1 2.214(3) . ?
Re1 Cl1 2.4890(11) . ?
O1 C17 1.164(5) . ?
N1 C7 1.284(5) . ?
N1 C8 1.487(5) . ?
C1 C2 1.387(6) . ?
C1 C6 1.403(5) . ?
C1 C7 1.454(6) . ?
Cl2 C3 1.744(4) . ?
C2 C3 1.371(6) . ?
C2 H2A 0.9300 . ?
N2 C10 1.274(5) . ?
N2 C9 1.481(5) . ?
O2 C18 1.156(5) . ?
Cl3 C5 1.750(4) . ?
C3 C4 1.373(5) . ?
O3 C19 1.150(6) . ?
Cl4 C13 1.741(5) . ?
C4 C5 1.393(6) . ?
C4 H4A 0.9300 . ?
Cl5 C15 1.734(5) . ?
C5 C6 1.378(6) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.517(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.472(6) . ?
C10 H10A 0.9300 . ?
C11 C16 1.391(6) . ?
C11 C12 1.392(5) . ?
C12 C13 1.396(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.373(7) . ?
C14 C15 1.386(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.377(6) . ?
C16 H16A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 Re1 C17 87.73(19) . . ?
C19 Re1 C18 87.94(19) . . ?
C17 Re1 C18 85.59(17) . . ?
C19 Re1 N2 96.14(17) . . ?
C17 Re1 N2 174.69(17) . . ?
C18 Re1 N2 98.15(15) . . ?
C19 Re1 N1 90.87(16) . . ?
C17 Re1 N1 99.34(15) . . ?
C18 Re1 N1 174.88(15) . . ?
N2 Re1 N1 77.02(12) . . ?
C19 Re1 Cl1 177.25(14) . . ?
C17 Re1 Cl1 94.83(14) . . ?
C18 Re1 Cl1 93.24(14) . . ?
N2 Re1 Cl1 81.24(10) . . ?
N1 Re1 Cl1 87.74(9) . . ?
C7 N1 C8 115.6(3) . . ?
C7 N1 Re1 134.5(3) . . ?
C8 N1 Re1 109.6(2) . . ?
C2 C1 C6 119.4(4) . . ?
C2 C1 C7 122.1(3) . . ?
C6 C1 C7 118.5(4) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C10 N2 C9 115.7(4) . . ?
C10 N2 Re1 133.7(3) . . ?
C9 N2 Re1 110.4(2) . . ?
C2 C3 C4 122.5(4) . . ?
C2 C3 Cl2 118.8(3) . . ?
C4 C3 Cl2 118.7(3) . . ?
C3 C4 C5 117.6(4) . . ?
C3 C4 H4A 121.2 . . ?
C5 C4 H4A 121.2 . . ?
C6 C5 C4 121.7(4) . . ?
C6 C5 Cl3 120.4(3) . . ?
C4 C5 Cl3 117.9(3) . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 H6A 120.4 . . ?
C1 C6 H6A 120.4 . . ?
N1 C7 C1 126.5(4) . . ?
N1 C7 H7A 116.7 . . ?
C1 C7 H7A 116.7 . . ?
N1 C8 C9 106.4(3) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
N2 C9 C8 106.1(3) . . ?
N2 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
N2 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
N2 C10 C11 124.9(4) . . ?
N2 C10 H10A 117.5 . . ?
C11 C10 H10A 117.5 . . ?
C16 C11 C12 120.0(4) . . ?
C16 C11 C10 120.6(4) . . ?
C12 C11 C10 119.1(4) . . ?
C11 C12 C13 118.2(5) . . ?
C11 C12 H12A 120.9 . . ?
C13 C12 H12A 120.9 . . ?
C14 C13 C12 122.3(4) . . ?
C14 C13 Cl4 119.5(4) . . ?
C12 C13 Cl4 118.1(4) . . ?
C13 C14 C15 118.3(5) . . ?
C13 C14 H14A 120.8 . . ?
C15 C14 H14A 120.8 . . ?
C16 C15 C14 121.1(5) . . ?
C16 C15 Cl5 119.4(4) . . ?
C14 C15 Cl5 119.6(4) . . ?
C15 C16 C11 120.0(4) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
O1 C17 Re1 175.4(4) . . ?
O2 C18 Re1 176.6(4) . . ?
O3 C19 Re1 177.9(4) . . ?

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 C1 C2 C3 0.4(7) . . . . ?
C7 C1 C2 C3 176.8(4) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C1 C2 C3 Cl2 179.7(3) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
Cl2 C3 C4 C5 -179.4(3) . . . . ?
C3 C4 C5 C6 -1.0(7) . . . . ?
C3 C4 C5 Cl3 177.7(4) . . . . ?
C4 C5 C6 C1 1.5(7) . . . . ?
Cl3 C5 C6 C1 -177.1(3) . . . . ?
C2 C1 C6 C5 -1.2(7) . . . . ?
C7 C1 C6 C5 -177.7(4) . . . . ?
C8 N1 C7 C1 -172.2(4) . . . . ?
Re1 N1 C7 C1 14.4(7) . . . . ?
C2 C1 C7 N1 42.3(7) . . . . ?
C6 C1 C7 N1 -141.2(5) . . . . ?
C7 N1 C8 C9 138.6(4) . . . . ?
Re1 N1 C8 C9 -46.3(4) . . . . ?
C10 N2 C9 C8 139.8(4) . . . . ?
Re1 N2 C9 C8 -45.7(4) . . . . ?
N1 C8 C9 N2 60.7(4) . . . . ?
C9 N2 C10 C11 -172.7(4) . . . . ?
Re1 N2 C10 C11 14.4(7) . . . . ?
N2 C10 C11 C16 56.4(7) . . . . ?
N2 C10 C11 C12 -129.5(5) . . . . ?
C16 C11 C12 C13 -2.5(7) . . . . ?
C10 C11 C12 C13 -176.7(4) . . . . ?
C11 C12 C13 C14 1.6(7) . . . . ?
C11 C12 C13 Cl4 179.1(3) . . . . ?
C12 C13 C14 C15 0.8(8) . . . . ?
Cl4 C13 C14 C15 -176.6(4) . . . . ?
C13 C14 C15 C16 -2.4(7) . . . . ?
C13 C14 C15 Cl5 178.0(4) . . . . ?
C14 C15 C16 C11 1.5(7) . . . . ?
Cl5 C15 C16 C11 -178.9(4) . . . . ?
C12 C11 C16 C15 1.0(7) . . . . ?
C10 C11 C16 C15 175.0(4) . . . . ?

_refine_diff_density_max         1.282
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.159

####################################################################### 
# 
# 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_C4
_database_code_depnum_ccdc_archive 'CCDC 1871499'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl3 F2 N2 O3 Re'
_chemical_formula_sum            'C19 H12 Cl3 F2 N2 O3 Re'
_chemical_formula_weight         646.86

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'
Cl Cl 0.1484 0.1585 '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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.4530(5)
_cell_length_b                   7.0730(2)
_cell_length_c                   23.5290(8)
_cell_angle_alpha                90
_cell_angle_beta                 126.1351(11)
_cell_angle_gamma                90
_cell_volume                     2076.98(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4326
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.95

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.069
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    6.278
_shelx_estimated_absorpt_T_min   0.602
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            9932
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4688
_reflns_number_gt                3574
_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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0517P)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         4688
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.44935(2) -0.35281(3) 0.87000(2) 0.01825(11) Uani 1 1 d . . . . .
Cl1 Cl 0.50406(14) -0.4892(2) 0.79856(9) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.6559(5) 0.0027(9) 0.9058(3) 0.0210(15) Uani 1 1 d . . . . .
N1 N 0.4636(4) -0.0748(7) 0.8343(3) 0.0206(12) Uani 1 1 d . . . . .
O1 O 0.6728(4) -0.3704(6) 1.0114(3) 0.0309(12) Uani 1 1 d . . . . .
F1 F 0.9807(3) -0.0620(6) 1.0516(2) 0.0432(11) Uani 1 1 d . . . . .
Cl2 Cl 0.87978(16) -0.3825(3) 0.95589(11) 0.0365(5) Uani 1 1 d . . . . .
O2 O 0.4340(4) -0.7509(6) 0.9156(2) 0.0272(11) Uani 1 1 d . . . . .
F2 F 0.0816(4) -1.0838(6) 0.7919(2) 0.0432(12) Uani 1 1 d . . . . .
C2 C 0.7057(7) -0.1608(9) 0.9055(4) 0.0283(17) Uani 1 1 d . . . . .
H2A H 0.665782 -0.255352 0.872579 0.034 Uiso 1 1 calc R U . . .
N2 N 0.2930(5) -0.3313(7) 0.7643(3) 0.0218(13) Uani 1 1 d . . . . .
Cl3 Cl 0.00429(16) -1.0572(3) 0.64421(10) 0.0382(5) Uani 1 1 d . . . . .
O3 O 0.3539(4) -0.1718(7) 0.9402(3) 0.0384(14) Uani 1 1 d . . . . .
C3 C 0.8152(6) -0.1813(9) 0.9548(4) 0.0242(16) Uani 1 1 d . . . . .
C4 C 0.8737(6) -0.0398(10) 1.0031(4) 0.0311(17) Uani 1 1 d . . . . .
C5 C 0.8273(6) 0.1229(10) 1.0038(4) 0.0350(19) Uani 1 1 d . . . . .
H5A H 0.868129 0.216360 1.037121 0.042 Uiso 1 1 calc R U . . .
C6 C 0.7175(6) 0.1464(10) 0.9537(4) 0.0337(18) Uani 1 1 d . . . . .
H6A H 0.684980 0.258888 0.952056 0.040 Uiso 1 1 calc R U . . .
C7 C 0.5412(6) 0.0359(9) 0.8529(4) 0.0253(16) Uani 1 1 d . . . . .
H7A H 0.522660 0.152031 0.830026 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3556(5) -0.0048(8) 0.7772(4) 0.0212(15) Uani 1 1 d . . . . .
H8A H 0.360913 0.102087 0.753538 0.025 Uiso 1 1 calc R U . . .
H8B H 0.316868 0.034378 0.795876 0.025 Uiso 1 1 calc R U . . .
C9 C 0.2993(6) -0.1676(9) 0.7268(3) 0.0238(15) Uani 1 1 d . . . . .
H9A H 0.227721 -0.129347 0.687950 0.029 Uiso 1 1 calc R U . . .
H9B H 0.338221 -0.204150 0.707946 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2066(6) -0.4304(10) 0.7277(4) 0.0265(16) Uani 1 1 d . . . . .
H10A H 0.157107 -0.391180 0.681447 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1760(5) -0.5950(9) 0.7490(4) 0.0235(15) Uani 1 1 d . . . . .
C12 C 0.1134(5) -0.7294(9) 0.6957(4) 0.0248(15) Uani 1 1 d . . . . .
H12A H 0.093530 -0.707989 0.650425 0.030 Uiso 1 1 calc R U . . .
C13 C 0.0815(6) -0.8933(10) 0.7105(4) 0.0299(17) Uani 1 1 d . . . . .
C14 C 0.1117(6) -0.9220(10) 0.7777(4) 0.0273(16) Uani 1 1 d . . . . .
C15 C 0.1676(6) -0.7909(10) 0.8293(4) 0.0296(17) Uani 1 1 d . . . . .
H15A H 0.183863 -0.811900 0.873679 0.036 Uiso 1 1 calc R U . . .
C16 C 0.1999(5) -0.6270(9) 0.8156(4) 0.0264(16) Uani 1 1 d . . . . .
H16A H 0.237997 -0.536751 0.850764 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5900(6) -0.3561(8) 0.9574(4) 0.0239(16) Uani 1 1 d . . . . .
C18 C 0.4334(5) -0.6013(9) 0.8958(4) 0.0220(15) Uani 1 1 d . . . . .
C19 C 0.3917(5) -0.2378(10) 0.9153(4) 0.0260(16) 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 C17 1.918(8) . ?
Re1 C18 1.922(7) . ?
Re1 C19 1.926(7) . ?
Re1 N1 2.200(5) . ?
Re1 N2 2.227(6) . ?
Re1 Cl1 2.4793(15) . ?
C1 C2 1.391(9) . ?
C1 C6 1.393(10) . ?
C1 C7 1.465(9) . ?
N1 C7 1.274(8) . ?
N1 C8 1.480(8) . ?
O1 C17 1.159(9) . ?
F1 C4 1.355(8) . ?
Cl2 C3 1.729(7) . ?
O2 C18 1.154(7) . ?
F2 C14 1.350(8) . ?
C2 C3 1.384(10) . ?
C2 H2A 0.9300 . ?
N2 C10 1.288(9) . ?
N2 C9 1.493(8) . ?
Cl3 C13 1.734(8) . ?
O3 C19 1.144(8) . ?
C3 C4 1.378(10) . ?
C4 C5 1.361(10) . ?
C5 C6 1.393(11) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.506(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.452(9) . ?
C10 H10A 0.9300 . ?
C11 C16 1.400(9) . ?
C11 C12 1.408(9) . ?
C12 C13 1.382(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.374(10) . ?
C14 C15 1.358(10) . ?
C15 C16 1.374(9) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 Re1 C18 85.7(3) . . ?
C17 Re1 C19 90.7(3) . . ?
C18 Re1 C19 91.4(3) . . ?
C17 Re1 N1 96.6(2) . . ?
C18 Re1 N1 176.6(2) . . ?
C19 Re1 N1 91.0(2) . . ?
C17 Re1 N2 174.3(2) . . ?
C18 Re1 N2 99.1(2) . . ?
C19 Re1 N2 92.2(2) . . ?
N1 Re1 N2 78.4(2) . . ?
C17 Re1 Cl1 95.7(2) . . ?
C18 Re1 Cl1 90.94(19) . . ?
C19 Re1 Cl1 173.3(2) . . ?
N1 Re1 Cl1 86.44(13) . . ?
N2 Re1 Cl1 81.28(14) . . ?
C2 C1 C6 119.6(7) . . ?
C2 C1 C7 121.6(6) . . ?
C6 C1 C7 118.6(6) . . ?
C7 N1 C8 115.8(5) . . ?
C7 N1 Re1 134.8(5) . . ?
C8 N1 Re1 109.4(4) . . ?
C3 C2 C1 119.3(7) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C10 N2 C9 115.5(6) . . ?
C10 N2 Re1 136.3(5) . . ?
C9 N2 Re1 107.8(4) . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 Cl2 119.6(6) . . ?
C2 C3 Cl2 120.6(5) . . ?
F1 C4 C5 118.5(7) . . ?
F1 C4 C3 119.4(6) . . ?
C5 C4 C3 122.1(7) . . ?
C4 C5 C6 118.5(7) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C5 C6 C1 120.6(6) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
N1 C7 C1 128.0(6) . . ?
N1 C7 H7A 116.0 . . ?
C1 C7 H7A 116.0 . . ?
N1 C8 C9 106.1(5) . . ?
N1 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
N1 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N2 C9 C8 109.7(5) . . ?
N2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 C11 128.8(7) . . ?
N2 C10 H10A 115.6 . . ?
C11 C10 H10A 115.6 . . ?
C16 C11 C12 118.5(6) . . ?
C16 C11 C10 126.2(6) . . ?
C12 C11 C10 115.3(6) . . ?
C13 C12 C11 120.1(7) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C14 C13 C12 119.0(7) . . ?
C14 C13 Cl3 121.5(6) . . ?
C12 C13 Cl3 119.5(6) . . ?
F2 C14 C15 119.1(6) . . ?
F2 C14 C13 118.6(6) . . ?
C15 C14 C13 122.3(7) . . ?
C14 C15 C16 119.5(7) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C15 C16 C11 120.5(7) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
O1 C17 Re1 174.9(6) . . ?
O2 C18 Re1 173.7(6) . . ?
O3 C19 Re1 177.5(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
C6 C1 C2 C3 2.7(10) . . . . ?
C7 C1 C2 C3 177.1(6) . . . . ?
C1 C2 C3 C4 -0.4(10) . . . . ?
C1 C2 C3 Cl2 -179.9(5) . . . . ?
C2 C3 C4 F1 179.3(6) . . . . ?
Cl2 C3 C4 F1 -1.2(9) . . . . ?
C2 C3 C4 C5 -0.7(11) . . . . ?
Cl2 C3 C4 C5 178.8(6) . . . . ?
F1 C4 C5 C6 179.5(7) . . . . ?
C3 C4 C5 C6 -0.5(12) . . . . ?
C4 C5 C6 C1 2.8(12) . . . . ?
C2 C1 C6 C5 -3.9(11) . . . . ?
C7 C1 C6 C5 -178.5(7) . . . . ?
C8 N1 C7 C1 -177.9(6) . . . . ?
Re1 N1 C7 C1 4.6(10) . . . . ?
C2 C1 C7 N1 50.8(10) . . . . ?
C6 C1 C7 N1 -134.8(7) . . . . ?
C7 N1 C8 C9 134.8(6) . . . . ?
Re1 N1 C8 C9 -47.1(5) . . . . ?
C10 N2 C9 C8 143.9(6) . . . . ?
Re1 N2 C9 C8 -41.4(6) . . . . ?
N1 C8 C9 N2 59.6(7) . . . . ?
C9 N2 C10 C11 -179.2(7) . . . . ?
Re1 N2 C10 C11 8.0(12) . . . . ?
N2 C10 C11 C16 35.1(12) . . . . ?
N2 C10 C11 C12 -147.1(7) . . . . ?
C16 C11 C12 C13 -3.2(10) . . . . ?
C10 C11 C12 C13 178.8(6) . . . . ?
C11 C12 C13 C14 0.1(10) . . . . ?
C11 C12 C13 Cl3 179.9(5) . . . . ?
C12 C13 C14 F2 -178.9(6) . . . . ?
Cl3 C13 C14 F2 1.3(9) . . . . ?
C12 C13 C14 C15 3.1(11) . . . . ?
Cl3 C13 C14 C15 -176.7(6) . . . . ?
F2 C14 C15 C16 179.0(6) . . . . ?
C13 C14 C15 C16 -3.1(11) . . . . ?
C14 C15 C16 C11 -0.3(11) . . . . ?
C12 C11 C16 C15 3.3(10) . . . . ?
C10 C11 C16 C15 -179.0(7) . . . . ?

_refine_diff_density_max         1.990
_refine_diff_density_min         -3.422
_refine_diff_density_rms         0.290

####################################################################### 
# 
# 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_C8
_database_code_depnum_ccdc_archive 'CCDC 1871500'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 Cl3 F2 N2 O3 Re'
_chemical_formula_sum            'C19 H12 Cl3 F2 N2 O3 Re'
_chemical_formula_weight         646.86

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'
Cl Cl 0.1484 0.1585 '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'

_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                   7.3006(5)
_cell_length_b                   11.5980(7)
_cell_length_c                   12.6789(8)
_cell_angle_alpha                104.105(5)
_cell_angle_beta                 97.855(5)
_cell_angle_gamma                96.998(5)
_cell_volume                     1017.88(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3489
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      27.94

_exptl_crystal_description       needle
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.111
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    6.405
_shelx_estimated_absorpt_T_min   0.567
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            8612
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.364
_diffrn_reflns_theta_max         29.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4683
_reflns_number_gt                4314
_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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0009P)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         4683
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0583
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C2 C 0.4235(6) 0.7946(4) 0.8358(4) 0.0239(11) Uani 1 1 d . . . . .
H2 H 0.400955 0.774530 0.759078 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5989(6) 0.8473(4) 0.8940(4) 0.0193(10) Uani 1 1 d . . . . .
C4 C 0.6362(6) 0.8760(4) 1.0085(4) 0.0200(10) Uani 1 1 d . . . . .
C5 C 0.4925(6) 0.8562(4) 1.0644(4) 0.0248(11) Uani 1 1 d . . . . .
H5 H 0.515282 0.876575 1.141158 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3138(6) 0.8061(4) 1.0073(4) 0.0263(11) Uani 1 1 d . . . . .
H6 H 0.215854 0.795590 1.045572 0.032 Uiso 1 1 calc R U . . .
C1 C 0.2813(6) 0.7718(4) 0.8929(4) 0.0221(11) Uani 1 1 d . . . . .
C7 C 0.0915(6) 0.7181(4) 0.8319(4) 0.0296(13) Uani 1 1 d . . . . .
H7 H -0.001129 0.766649 0.836934 0.035 Uiso 1 1 calc R U . . .
C8 C -0.1437(6) 0.5781(4) 0.7033(4) 0.0230(11) Uani 1 1 d . . . . .
H8A H -0.137807 0.596428 0.633062 0.028 Uiso 1 1 calc R U . . .
H8B H -0.229236 0.625071 0.739828 0.028 Uiso 1 1 calc R U . . .
C9 C -0.2136(6) 0.4464(4) 0.6843(4) 0.0217(11) Uani 1 1 d . . . . .
H9A H -0.233681 0.429036 0.753306 0.026 Uiso 1 1 calc R U . . .
H9B H -0.331438 0.422973 0.633009 0.026 Uiso 1 1 calc R U . . .
C10 C -0.1317(6) 0.2943(4) 0.5498(3) 0.0182(10) Uani 1 1 d . . . . .
H10 H -0.259338 0.285288 0.523403 0.022 Uiso 1 1 calc R U . . .
C11 C -0.0299(6) 0.2093(4) 0.4846(3) 0.0170(10) Uani 1 1 d . . . . .
C16 C -0.1350(6) 0.0985(4) 0.4232(3) 0.0192(10) Uani 1 1 d . . . . .
H16 H -0.263858 0.084707 0.420991 0.023 Uiso 1 1 calc R U . . .
C15 C -0.0493(6) 0.0097(4) 0.3662(3) 0.0212(10) Uani 1 1 d . . . . .
H15 H -0.119809 -0.064489 0.327083 0.025 Uiso 1 1 calc R U . . .
C14 C 0.1396(6) 0.0304(4) 0.3668(3) 0.0202(10) Uani 1 1 d . . . . .
C13 C 0.2410(6) 0.1424(4) 0.4226(3) 0.0180(10) Uani 1 1 d . . . . .
C12 C 0.1607(6) 0.2324(4) 0.4813(3) 0.0182(10) Uani 1 1 d . . . . .
H12 H 0.231693 0.307165 0.518055 0.022 Uiso 1 1 calc R U . . .
C17 C 0.4253(6) 0.5318(4) 0.8556(4) 0.0219(10) Uani 1 1 d . . . . .
C18 C 0.3237(6) 0.3185(4) 0.7251(4) 0.0217(10) Uani 1 1 d . . . . .
C19 C 0.1017(6) 0.4009(4) 0.8668(4) 0.0205(10) Uani 1 1 d . . . . .
Cl2 Cl 0.86135(15) 0.93422(11) 1.07782(9) 0.0283(3) Uani 1 1 d . . . . .
Cl3 Cl 0.25393(17) -0.08181(11) 0.30249(10) 0.0312(3) Uani 1 1 d . . . . .
Cl1 Cl 0.31242(14) 0.53629(10) 0.60404(8) 0.0197(2) Uani 1 1 d . . . . .
F1 F 0.7385(3) 0.8697(3) 0.8391(2) 0.0293(7) Uani 1 1 d . . . . .
F2 F 0.4256(3) 0.1642(2) 0.4203(2) 0.0291(7) Uani 1 1 d . . . . .
N1 N 0.0454(5) 0.6100(3) 0.7728(3) 0.0182(8) Uani 1 1 d . . . . .
N2 N -0.0692(4) 0.3791(3) 0.6381(3) 0.0154(8) Uani 1 1 d . . . . .
O1 O 0.5637(4) 0.5695(3) 0.9155(3) 0.0287(8) Uani 1 1 d . . . . .
O2 O 0.4035(4) 0.2380(3) 0.7134(3) 0.0287(8) Uani 1 1 d . . . . .
O3 O 0.0434(5) 0.3687(3) 0.9352(3) 0.0341(9) Uani 1 1 d . . . . .
Re1 Re 0.19971(2) 0.45618(2) 0.75172(2) 0.01386(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
C2 C3 1.374(6) . ?
C2 C1 1.379(7) . ?
C2 H2 0.9300 . ?
C3 F1 1.344(5) . ?
C3 C4 1.388(6) . ?
C4 C5 1.371(7) . ?
C4 Cl2 1.725(4) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9300 . ?
C6 C1 1.386(6) . ?
C6 H6 0.9300 . ?
C1 C7 1.472(6) . ?
C7 N1 1.272(5) . ?
C7 H7 0.9300 . ?
C8 N1 1.484(5) . ?
C8 C9 1.499(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.487(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.282(5) . ?
C10 C11 1.469(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(6) . ?
C11 C16 1.398(6) . ?
C16 C15 1.376(6) . ?
C16 H16 0.9300 . ?
C15 C14 1.370(6) . ?
C15 H15 0.9300 . ?
C14 C13 1.382(6) . ?
C14 Cl3 1.729(4) . ?
C13 F2 1.347(5) . ?
C13 C12 1.370(6) . ?
C12 H12 0.9300 . ?
C17 O1 1.145(5) . ?
C17 Re1 1.926(4) . ?
C18 O2 1.150(5) . ?
C18 Re1 1.912(5) . ?
C19 O3 1.138(6) . ?
C19 Re1 1.918(5) . ?
Cl1 Re1 2.4758(12) . ?
N1 Re1 2.205(3) . ?
N2 Re1 2.214(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
F1 C3 C2 119.6(4) . . ?
F1 C3 C4 119.1(4) . . ?
C2 C3 C4 121.3(5) . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 Cl2 121.2(3) . . ?
C3 C4 Cl2 119.8(4) . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.8(5) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C2 C1 C6 120.2(4) . . ?
C2 C1 C7 119.7(4) . . ?
C6 C1 C7 120.0(5) . . ?
N1 C7 C1 124.5(4) . . ?
N1 C7 H7 117.7 . . ?
C1 C7 H7 117.7 . . ?
N1 C8 C9 109.6(3) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C8 107.5(4) . . ?
N2 C9 H9A 110.2 . . ?
C8 C9 H9A 110.2 . . ?
N2 C9 H9B 110.2 . . ?
C8 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N2 C10 C11 129.0(4) . . ?
N2 C10 H10 115.5 . . ?
C11 C10 H10 115.5 . . ?
C12 C11 C16 119.4(4) . . ?
C12 C11 C10 124.3(4) . . ?
C16 C11 C10 116.3(4) . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C14 C13 119.1(4) . . ?
C15 C14 Cl3 121.3(3) . . ?
C13 C14 Cl3 119.6(3) . . ?
F2 C13 C12 118.5(4) . . ?
F2 C13 C14 119.2(4) . . ?
C12 C13 C14 122.4(4) . . ?
C13 C12 C11 118.4(4) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
O1 C17 Re1 175.3(4) . . ?
O2 C18 Re1 177.0(4) . . ?
O3 C19 Re1 179.7(4) . . ?
C7 N1 C8 116.6(3) . . ?
C7 N1 Re1 131.3(3) . . ?
C8 N1 Re1 112.1(2) . . ?
C10 N2 C9 114.7(3) . . ?
C10 N2 Re1 138.5(3) . . ?
C9 N2 Re1 106.8(2) . . ?
C18 Re1 C19 88.2(2) . . ?
C18 Re1 C17 84.30(17) . . ?
C19 Re1 C17 88.77(19) . . ?
C18 Re1 N1 176.52(14) . . ?
C19 Re1 N1 93.00(17) . . ?
C17 Re1 N1 98.99(15) . . ?
C18 Re1 N2 99.42(15) . . ?
C19 Re1 N2 90.16(16) . . ?
C17 Re1 N2 176.10(14) . . ?
N1 Re1 N2 77.32(12) . . ?
C18 Re1 Cl1 95.24(15) . . ?
C19 Re1 Cl1 176.49(13) . . ?
C17 Re1 Cl1 92.34(15) . . ?
N1 Re1 Cl1 83.54(11) . . ?
N2 Re1 Cl1 88.52(10) . . ?

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
C1 C2 C3 F1 179.9(4) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
F1 C3 C4 C5 178.1(4) . . . . ?
C2 C3 C4 C5 -3.0(7) . . . . ?
F1 C3 C4 Cl2 -2.5(6) . . . . ?
C2 C3 C4 Cl2 176.4(3) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
Cl2 C4 C5 C6 -178.1(4) . . . . ?
C4 C5 C6 C1 2.3(7) . . . . ?
C3 C2 C1 C6 2.6(7) . . . . ?
C3 C2 C1 C7 178.5(4) . . . . ?
C5 C6 C1 C2 -4.3(7) . . . . ?
C5 C6 C1 C7 179.8(4) . . . . ?
C2 C1 C7 N1 70.2(7) . . . . ?
C6 C1 C7 N1 -113.8(6) . . . . ?
N1 C8 C9 N2 -54.2(5) . . . . ?
N2 C10 C11 C12 -25.9(8) . . . . ?
N2 C10 C11 C16 153.7(5) . . . . ?
C12 C11 C16 C15 4.5(7) . . . . ?
C10 C11 C16 C15 -175.1(4) . . . . ?
C11 C16 C15 C14 -1.6(7) . . . . ?
C16 C15 C14 C13 -1.9(7) . . . . ?
C16 C15 C14 Cl3 176.3(4) . . . . ?
C15 C14 C13 F2 -177.8(4) . . . . ?
Cl3 C14 C13 F2 3.9(6) . . . . ?
C15 C14 C13 C12 2.7(7) . . . . ?
Cl3 C14 C13 C12 -175.6(4) . . . . ?
F2 C13 C12 C11 -179.3(4) . . . . ?
C14 C13 C12 C11 0.2(7) . . . . ?
C16 C11 C12 C13 -3.7(6) . . . . ?
C10 C11 C12 C13 175.9(4) . . . . ?
C1 C7 N1 C8 -170.3(5) . . . . ?
C1 C7 N1 Re1 8.8(8) . . . . ?
C9 C8 N1 C7 -152.5(4) . . . . ?
C9 C8 N1 Re1 28.2(5) . . . . ?
C11 C10 N2 C9 -178.5(5) . . . . ?
C11 C10 N2 Re1 -1.3(9) . . . . ?
C8 C9 N2 C10 -129.1(4) . . . . ?
C8 C9 N2 Re1 52.9(4) . . . . ?

_refine_diff_density_max         1.350
_refine_diff_density_min         -1.344
_refine_diff_density_rms         0.170

####################################################################### 
# 
# 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_C9
_database_code_depnum_ccdc_archive 'CCDC 1871502'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 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         'C21 H12 Br Cl2 F6 N2 O3 Re'
_chemical_formula_sum            'C21 H12 Br Cl2 F6 N2 O3 Re'
_chemical_formula_weight         791.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.2547(4)
_cell_length_b                   26.9040(16)
_cell_length_c                   12.6293(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.127(6)
_cell_angle_gamma                90
_cell_volume                     2461.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2563
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.136
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    6.850
_shelx_estimated_absorpt_T_min   0.494
_shelx_estimated_absorpt_T_max   0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            21636
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.404
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4820
_reflns_number_gt                4144
_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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0144P)²+3.5384P] 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         4820
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0571
_refine_ls_wR_factor_gt          0.0542
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.004
_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 0.97526(3) 0.63219(2) 0.22675(2) 0.01739(6) Uani 1 1 d . . . . .
Br1 Br 0.83714(7) 0.60554(2) 0.03859(4) 0.02715(13) Uani 1 1 d . . . . .
Cl2 Cl 1.26316(19) 0.76688(5) 0.34393(11) 0.0361(3) Uani 1 1 d . . . . .
Cl1 Cl 1.3150(2) 0.50293(6) 0.42558(12) 0.0484(4) Uani 1 1 d . . . . .
N1 N 1.2071(5) 0.58256(14) 0.1974(3) 0.0197(9) Uani 1 1 d . . . . .
C12 C 0.8839(7) 0.77746(18) 0.1053(4) 0.0240(11) Uani 1 1 d . . . . .
H12 H 0.8630 0.7641 0.0378 0.029 Uiso 1 1 calc R U . . .
C6 C 1.1247(7) 0.4818(2) 0.3498(4) 0.0320(13) Uani 1 1 d . . . . .
O1 O 0.7169(5) 0.56009(13) 0.3346(3) 0.0323(9) Uani 1 1 d . . . . .
C5 C 1.0079(8) 0.4474(2) 0.3915(5) 0.0367(14) Uani 1 1 d . . . . .
H5 H 1.0326 0.4347 0.4593 0.044 Uiso 1 1 calc R U . . .
C19 C 1.0815(7) 0.64888(17) 0.3648(4) 0.0221(11) Uani 1 1 d . . . . .
C15 C 0.9464(7) 0.81869(19) 0.3061(4) 0.0304(13) Uani 1 1 d . . . . .
H15 H 0.9681 0.8324 0.3732 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7929(7) 0.83234(19) 0.2439(4) 0.0308(13) Uani 1 1 d . . . . .
H14 H 0.7099 0.8552 0.2695 0.037 Uiso 1 1 calc R U . . .
C9 C 1.3005(6) 0.65047(18) 0.0871(4) 0.0248(12) Uani 1 1 d . . . . .
H9A H 1.4020 0.6715 0.0680 0.030 Uiso 1 1 calc R U . . .
H9B H 1.2467 0.6352 0.0230 0.030 Uiso 1 1 calc R U . . .
O2 O 0.6602(5) 0.70618(13) 0.2575(3) 0.0416(11) Uani 1 1 d . . . . .
N2 N 1.1608(5) 0.68014(14) 0.1387(3) 0.0185(9) Uani 1 1 d . . . . .
C17 C 0.8167(6) 0.58614(18) 0.2939(4) 0.0223(11) Uani 1 1 d . . . . .
C8 C 1.3688(6) 0.61104(18) 0.1642(4) 0.0253(12) Uani 1 1 d . . . . .
H8A H 1.4544 0.5891 0.1308 0.030 Uiso 1 1 calc R U . . .
H8B H 1.4325 0.6263 0.2254 0.030 Uiso 1 1 calc R U . . .
C1 C 1.0931(7) 0.50099(17) 0.2487(4) 0.0232(11) Uani 1 1 d . . . . .
C18 C 0.7816(7) 0.67973(17) 0.2444(4) 0.0237(12) Uani 1 1 d . . . . .
C16 C 1.0681(7) 0.78442(18) 0.2675(4) 0.0261(12) Uani 1 1 d . . . . .
C3 C 0.8212(7) 0.45049(18) 0.2301(4) 0.0284(13) Uani 1 1 d . . . . .
C11 C 1.0363(7) 0.76295(17) 0.1680(4) 0.0222(11) Uani 1 1 d . . . . .
C10 C 1.1685(6) 0.72698(17) 0.1264(4) 0.0202(11) Uani 1 1 d . . . . .
H10 H 1.2644 0.7396 0.0884 0.024 Uiso 1 1 calc R U . . .
C7 C 1.2308(7) 0.53615(19) 0.2081(4) 0.0286(13) Uani 1 1 d . . . . .
H7 H 1.3429 0.5231 0.1891 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6503(8) 0.4336(2) 0.1686(5) 0.0344(14) Uani 1 1 d . . . . .
C2 C 0.9394(7) 0.48494(18) 0.1880(4) 0.0273(12) Uani 1 1 d . . . . .
H2 H 0.9158 0.4971 0.1197 0.033 Uiso 1 1 calc R U . . .
C13 C 0.7615(7) 0.81224(19) 0.1435(4) 0.0258(12) Uani 1 1 d . . . . .
C4 C 0.8546(7) 0.4320(2) 0.3315(5) 0.0329(14) Uani 1 1 d . . . . .
H4 H 0.7736 0.4092 0.3591 0.040 Uiso 1 1 calc R U . . .
O3 O 1.1379(5) 0.65617(15) 0.4482(3) 0.0396(10) Uani 1 1 d . . . . .
C21 C 0.5962(8) 0.8279(2) 0.0758(5) 0.0375(14) Uani 1 1 d . . . . .
F5 F 0.6195(6) 0.86812(19) 0.0250(5) 0.139(3) Uani 1 1 d . . . . .
F6 F 0.4466(5) 0.83220(17) 0.1292(3) 0.0703(12) Uani 1 1 d . . . . .
F4 F 0.5451(5) 0.79371(18) 0.0028(3) 0.0820(14) Uani 1 1 d . . . . .
F2 F 0.6494(4) 0.38462(11) 0.1513(3) 0.0423(9) Uani 1 1 d . . . . .
F3 F 0.6284(5) 0.45485(15) 0.0729(3) 0.0684(12) Uani 1 1 d . . . . .
F1 F 0.4964(4) 0.44248(12) 0.2188(3) 0.0525(10) 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 C17 1.919(5) . ?
Re1 C19 1.921(6) . ?
Re1 C18 1.922(5) . ?
Re1 N1 2.195(4) . ?
Re1 N2 2.208(4) . ?
Re1 Br1 2.6278(6) . ?
Cl2 C16 1.734(5) . ?
Cl1 C6 1.733(6) . ?
N1 C7 1.266(6) . ?
N1 C8 1.481(6) . ?
C12 C11 1.381(7) . ?
C12 C13 1.394(7) . ?
C12 H12 0.9300 . ?
C6 C5 1.380(7) . ?
C6 C1 1.384(7) . ?
O1 C17 1.149(5) . ?
C5 C4 1.374(7) . ?
C5 H5 0.9300 . ?
C19 O3 1.126(6) . ?
C15 C14 1.377(7) . ?
C15 C16 1.383(7) . ?
C15 H15 0.9300 . ?
C14 C13 1.386(7) . ?
C14 H14 0.9300 . ?
C9 N2 1.471(6) . ?
C9 C8 1.506(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O2 C18 1.151(6) . ?
N2 C10 1.271(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.387(7) . ?
C1 C7 1.487(7) . ?
C16 C11 1.391(7) . ?
C3 C4 1.383(7) . ?
C3 C2 1.388(7) . ?
C3 C20 1.497(7) . ?
C11 C10 1.479(6) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C20 F1 1.335(6) . ?
C20 F2 1.336(6) . ?
C20 F3 1.339(6) . ?
C2 H2 0.9300 . ?
C13 C21 1.495(7) . ?
C4 H4 0.9300 . ?
C21 F5 1.273(7) . ?
C21 F6 1.314(6) . ?
C21 F4 1.341(7) . ?

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
C17 Re1 C19 88.3(2) . . ?
C17 Re1 C18 85.35(19) . . ?
C19 Re1 C18 89.9(2) . . ?
C17 Re1 N1 99.49(17) . . ?
C19 Re1 N1 91.29(17) . . ?
C18 Re1 N1 175.04(17) . . ?
C17 Re1 N2 174.95(17) . . ?
C19 Re1 N2 95.45(17) . . ?
C18 Re1 N2 98.00(16) . . ?
N1 Re1 N2 77.10(14) . . ?
C17 Re1 Br1 90.86(15) . . ?
C19 Re1 Br1 177.48(15) . . ?
C18 Re1 Br1 92.39(16) . . ?
N1 Re1 Br1 86.50(10) . . ?
N2 Re1 Br1 85.24(10) . . ?
C7 N1 C8 115.8(4) . . ?
C7 N1 Re1 133.0(3) . . ?
C8 N1 Re1 111.1(3) . . ?
C11 C12 C13 119.8(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C5 C6 C1 121.9(5) . . ?
C5 C6 Cl1 119.8(4) . . ?
C1 C6 Cl1 118.3(4) . . ?
C4 C5 C6 119.2(5) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
O3 C19 Re1 175.6(4) . . ?
C14 C15 C16 119.3(5) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C14 C13 120.3(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N2 C9 C8 107.8(4) . . ?
N2 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
N2 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.5 . . ?
C10 N2 C9 116.6(4) . . ?
C10 N2 Re1 132.3(3) . . ?
C9 N2 Re1 111.1(3) . . ?
O1 C17 Re1 177.2(4) . . ?
N1 C8 C9 108.0(4) . . ?
N1 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C6 C1 C2 118.8(5) . . ?
C6 C1 C7 118.3(5) . . ?
C2 C1 C7 122.8(5) . . ?
O2 C18 Re1 176.3(4) . . ?
C15 C16 C11 121.2(5) . . ?
C15 C16 Cl2 120.2(4) . . ?
C11 C16 Cl2 118.7(4) . . ?
C4 C3 C2 121.0(5) . . ?
C4 C3 C20 118.0(5) . . ?
C2 C3 C20 121.0(5) . . ?
C12 C11 C16 119.3(5) . . ?
C12 C11 C10 119.7(4) . . ?
C16 C11 C10 120.9(5) . . ?
N2 C10 C11 124.8(4) . . ?
N2 C10 H10 117.6 . . ?
C11 C10 H10 117.6 . . ?
N1 C7 C1 125.0(4) . . ?
N1 C7 H7 117.5 . . ?
C1 C7 H7 117.5 . . ?
F1 C20 F2 104.9(4) . . ?
F1 C20 F3 106.9(5) . . ?
F2 C20 F3 105.9(5) . . ?
F1 C20 C3 113.0(5) . . ?
F2 C20 C3 112.4(4) . . ?
F3 C20 C3 113.1(5) . . ?
C1 C2 C3 119.4(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C14 C13 C12 120.1(5) . . ?
C14 C13 C21 120.0(5) . . ?
C12 C13 C21 119.8(5) . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
F5 C21 F6 108.7(6) . . ?
F5 C21 F4 106.0(6) . . ?
F6 C21 F4 102.0(5) . . ?
F5 C21 C13 113.8(5) . . ?
F6 C21 C13 113.0(5) . . ?
F4 C21 C13 112.5(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
C1 C6 C5 C4 -0.8(8) . . . . ?
Cl1 C6 C5 C4 178.2(4) . . . . ?
C16 C15 C14 C13 -0.5(8) . . . . ?
C8 C9 N2 C10 137.3(4) . . . . ?
C8 C9 N2 Re1 -42.1(4) . . . . ?
C7 N1 C8 C9 141.2(5) . . . . ?
Re1 N1 C8 C9 -42.1(5) . . . . ?
N2 C9 C8 N1 55.3(5) . . . . ?
C5 C6 C1 C2 0.0(8) . . . . ?
Cl1 C6 C1 C2 -179.0(4) . . . . ?
C5 C6 C1 C7 -177.1(5) . . . . ?
Cl1 C6 C1 C7 3.9(6) . . . . ?
C14 C15 C16 C11 -1.1(8) . . . . ?
C14 C15 C16 Cl2 179.6(4) . . . . ?
C13 C12 C11 C16 -1.8(7) . . . . ?
C13 C12 C11 C10 -178.5(4) . . . . ?
C15 C16 C11 C12 2.3(7) . . . . ?
Cl2 C16 C11 C12 -178.5(4) . . . . ?
C15 C16 C11 C10 178.9(5) . . . . ?
Cl2 C16 C11 C10 -1.8(6) . . . . ?
C9 N2 C10 C11 177.3(4) . . . . ?
Re1 N2 C10 C11 -3.5(7) . . . . ?
C12 C11 C10 N2 -92.3(6) . . . . ?
C16 C11 C10 N2 91.1(6) . . . . ?
C8 N1 C7 C1 174.9(5) . . . . ?
Re1 N1 C7 C1 -0.9(8) . . . . ?
C6 C1 C7 N1 -106.7(6) . . . . ?
C2 C1 C7 N1 76.2(7) . . . . ?
C4 C3 C20 F1 56.4(6) . . . . ?
C2 C3 C20 F1 -121.5(5) . . . . ?
C4 C3 C20 F2 -62.1(6) . . . . ?
C2 C3 C20 F2 120.1(5) . . . . ?
C4 C3 C20 F3 178.1(5) . . . . ?
C2 C3 C20 F3 0.2(7) . . . . ?
C6 C1 C2 C3 0.4(7) . . . . ?
C7 C1 C2 C3 177.4(4) . . . . ?
C4 C3 C2 C1 0.0(7) . . . . ?
C20 C3 C2 C1 177.8(4) . . . . ?
C15 C14 C13 C12 0.9(8) . . . . ?
C15 C14 C13 C21 -178.9(5) . . . . ?
C11 C12 C13 C14 0.2(7) . . . . ?
C11 C12 C13 C21 -179.9(4) . . . . ?
C6 C5 C4 C3 1.1(8) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
C20 C3 C4 C5 -178.6(5) . . . . ?
C14 C13 C21 F5 83.4(7) . . . . ?
C12 C13 C21 F5 -96.5(7) . . . . ?
C14 C13 C21 F6 -41.2(7) . . . . ?
C12 C13 C21 F6 138.9(5) . . . . ?
C14 C13 C21 F4 -156.0(5) . . . . ?
C12 C13 C21 F4 24.1(7) . . . . ?

_refine_diff_density_max         0.880
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_C10
_database_code_depnum_ccdc_archive 'CCDC 1871503'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 Br Cl2 F6 N2 O3 Re'
_chemical_formula_sum            'C21 H12 Br Cl2 F6 N2 O3 Re'
_chemical_formula_weight         791.34

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.6938(1)
_cell_length_b                   12.9012(2)
_cell_length_c                   22.2519(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.119(1)
_cell_angle_gamma                90
_cell_volume                     2782.33(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3240
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.889
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    6.060
_shelx_estimated_absorpt_T_min   0.252
_shelx_estimated_absorpt_T_max   0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            36469
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.101
_diffrn_reflns_theta_max         30.856
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8707
_reflns_number_gt                6377
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.38.43'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43'
_computing_data_reduction        'CrysAlisPro 1.171.38.43'
_computing_structure_solution    OLEX2
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_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)+(0.0445P)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         8707
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.34499(2) 0.84815(2) 0.26273(2) 0.01627(6) Uani 1 1 d . . . . .
Br1 Br 0.48022(4) 0.96725(3) 0.18829(2) 0.02094(10) Uani 1 1 d . . . . .
Cl2 Cl 0.81845(11) 0.92102(9) 0.32095(5) 0.0300(3) Uani 1 1 d . . . . .
Cl1 Cl -0.07216(12) 0.69354(9) 0.19259(7) 0.0371(3) Uani 1 1 d . . . . .
F1 F -0.0152(4) 1.1241(2) 0.03273(16) 0.0568(10) Uani 1 1 d . . . . .
F2 F 0.1984(4) 1.0782(2) 0.03695(16) 0.0572(10) Uani 1 1 d . . . . .
F3 F 0.1098(3) 1.1614(2) 0.10985(15) 0.0420(8) Uani 1 1 d . . . . .
F4 F 0.3742(5) 0.6737(3) 0.49340(17) 0.0896(16) Uani 1 1 d . . . . .
F5 F 0.3750(4) 0.8228(3) 0.53420(19) 0.0826(14) Uani 1 1 d . . . . .
F6 F 0.5293(4) 0.7168(4) 0.55731(18) 0.0930(15) Uani 1 1 d . . . . .
O1 O 0.4031(3) 0.9834(2) 0.37377(14) 0.0224(7) Uani 1 1 d . . . . .
O2 O 0.0861(3) 0.9843(2) 0.25101(15) 0.0292(8) Uani 1 1 d . . . . .
O3 O 0.1943(3) 0.6999(3) 0.34532(17) 0.0393(9) Uani 1 1 d . . . . .
N1 N 0.5331(3) 0.7532(2) 0.26214(15) 0.0173(7) Uani 1 1 d . . . . .
N2 N 0.3057(3) 0.7410(2) 0.18757(15) 0.0157(7) Uani 1 1 d . . . . .
C18 C 0.3859(4) 0.9324(3) 0.3320(2) 0.0197(9) Uani 1 1 d . . . . .
C17 C 0.1825(4) 0.9319(3) 0.25417(19) 0.0206(9) Uani 1 1 d . . . . .
C19 C 0.2507(4) 0.7554(3) 0.3145(2) 0.0253(10) Uani 1 1 d . . . . .
C12 C 0.7107(4) 0.8728(3) 0.3757(2) 0.0232(10) Uani 1 1 d . . . . .
C13 C 0.7112(5) 0.9184(4) 0.4319(2) 0.0288(11) Uani 1 1 d . . . . .
H13 H 0.768073 0.976736 0.440475 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6269(5) 0.8770(4) 0.4753(2) 0.0326(12) Uani 1 1 d . . . . .
H14 H 0.626474 0.906738 0.514333 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5428(5) 0.7923(4) 0.4622(2) 0.0304(11) Uani 1 1 d . . . . .
C16 C 0.5429(4) 0.7471(4) 0.4056(2) 0.0264(10) Uani 1 1 d . . . . .
H16 H 0.486635 0.688384 0.397052 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6268(4) 0.7890(3) 0.3614(2) 0.0209(9) Uani 1 1 d . . . . .
C10 C 0.6287(4) 0.7402(3) 0.3014(2) 0.0203(9) Uani 1 1 d . . . . .
H10 H 0.704723 0.697221 0.291726 0.024 Uiso 1 1 calc R U . . .
C9 C 0.5440(4) 0.6956(3) 0.2052(2) 0.0210(9) Uani 1 1 d . . . . .
H9A H 0.611656 0.638468 0.209702 0.025 Uiso 1 1 calc R U . . .
H9B H 0.574870 0.742296 0.172821 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4019(4) 0.6526(3) 0.1901(2) 0.0213(9) Uani 1 1 d . . . . .
H8A H 0.402549 0.616431 0.150812 0.026 Uiso 1 1 calc R U . . .
H8B H 0.373474 0.602559 0.221219 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2093(4) 0.7372(3) 0.1478(2) 0.0209(9) Uani 1 1 d . . . . .
H7 H 0.203098 0.677358 0.123044 0.025 Uiso 1 1 calc R U . . .
C1 C 0.1065(4) 0.8205(3) 0.1380(2) 0.0199(9) Uani 1 1 d . . . . .
C6 C -0.0295(4) 0.8070(3) 0.1541(2) 0.0253(10) Uani 1 1 d . . . . .
C5 C -0.1289(4) 0.8816(4) 0.1435(2) 0.0316(12) Uani 1 1 d . . . . .
H5 H -0.221265 0.871247 0.155659 0.038 Uiso 1 1 calc R U . . .
C4 C -0.0911(4) 0.9710(4) 0.1150(2) 0.0301(11) Uani 1 1 d . . . . .
H4 H -0.158519 1.022741 0.106697 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0432(5) 0.9869(3) 0.0983(2) 0.0263(10) Uani 1 1 d . . . . .
C2 C 0.1428(4) 0.9108(3) 0.10965(19) 0.0212(9) Uani 1 1 d . . . . .
H2 H 0.235310 0.921445 0.097788 0.025 Uiso 1 1 calc R U . . .
C20 C 0.0843(5) 1.0863(4) 0.0692(2) 0.0358(12) Uani 1 1 d . . . . .
C21 C 0.4572(6) 0.7484(5) 0.5110(3) 0.0516(16) 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 C19 1.907(5) . ?
Re1 C17 1.917(4) . ?
Re1 C18 1.921(5) . ?
Re1 N1 2.197(3) . ?
Re1 N2 2.197(3) . ?
Re1 Br1 2.6282(4) . ?
Cl2 C12 1.736(5) . ?
Cl1 C6 1.749(5) . ?
F1 C20 1.341(6) . ?
F2 C20 1.334(6) . ?
F3 C20 1.345(6) . ?
F4 C21 1.311(7) . ?
F5 C21 1.357(7) . ?
F6 C21 1.300(7) . ?
O1 C18 1.149(5) . ?
O2 C17 1.154(5) . ?
O3 C19 1.138(5) . ?
N1 C10 1.273(5) . ?
N1 C9 1.474(5) . ?
N2 C7 1.275(5) . ?
N2 C8 1.474(5) . ?
C12 C13 1.381(6) . ?
C12 C11 1.386(6) . ?
C13 C14 1.385(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(6) . ?
C15 C21 1.489(7) . ?
C16 C11 1.398(6) . ?
C16 H16 0.9500 . ?
C11 C10 1.477(6) . ?
C10 H10 0.9500 . ?
C9 C8 1.518(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 C1 1.478(6) . ?
C7 H7 0.9500 . ?
C1 C2 1.374(6) . ?
C1 C6 1.385(6) . ?
C6 C5 1.379(6) . ?
C5 C4 1.369(7) . ?
C5 H5 0.9500 . ?
C4 C3 1.376(6) . ?
C4 H4 0.9500 . ?
C3 C2 1.396(6) . ?
C3 C20 1.494(6) . ?
C2 H2 0.9500 . ?

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
C19 Re1 C17 90.65(18) . . ?
C19 Re1 C18 87.99(18) . . ?
C17 Re1 C18 85.23(18) . . ?
C19 Re1 N1 93.51(16) . . ?
C17 Re1 N1 173.93(15) . . ?
C18 Re1 N1 99.32(15) . . ?
C19 Re1 N2 89.24(16) . . ?
C17 Re1 N2 98.59(15) . . ?
C18 Re1 N2 175.30(15) . . ?
N1 Re1 N2 77.06(12) . . ?
C19 Re1 Br1 176.89(13) . . ?
C17 Re1 Br1 91.53(12) . . ?
C18 Re1 Br1 94.40(12) . . ?
N1 Re1 Br1 84.15(8) . . ?
N2 Re1 Br1 88.24(8) . . ?
C10 N1 C9 117.4(3) . . ?
C10 N1 Re1 131.5(3) . . ?
C9 N1 Re1 111.1(2) . . ?
C7 N2 C8 116.8(3) . . ?
C7 N2 Re1 131.7(3) . . ?
C8 N2 Re1 111.0(3) . . ?
O1 C18 Re1 176.4(3) . . ?
O2 C17 Re1 177.4(4) . . ?
O3 C19 Re1 179.9(5) . . ?
C13 C12 C11 122.2(4) . . ?
C13 C12 Cl2 119.3(4) . . ?
C11 C12 Cl2 118.5(4) . . ?
C12 C13 C14 118.3(4) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C13 C14 C15 120.6(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 C21 120.7(5) . . ?
C14 C15 C21 118.6(5) . . ?
C15 C16 C11 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?
C12 C11 C16 119.2(4) . . ?
C12 C11 C10 121.5(4) . . ?
C16 C11 C10 119.3(4) . . ?
N1 C10 C11 122.9(4) . . ?
N1 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
N1 C9 C8 107.2(3) . . ?
N1 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
N1 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
N2 C8 C9 107.2(3) . . ?
N2 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
N2 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
N2 C7 C1 123.9(4) . . ?
N2 C7 H7 118.1 . . ?
C1 C7 H7 118.1 . . ?
C2 C1 C6 118.6(4) . . ?
C2 C1 C7 120.4(4) . . ?
C6 C1 C7 120.9(4) . . ?
C5 C6 C1 122.3(4) . . ?
C5 C6 Cl1 119.8(4) . . ?
C1 C6 Cl1 117.9(3) . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 C20 120.5(4) . . ?
C2 C3 C20 119.5(4) . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
F2 C20 F1 107.3(5) . . ?
F2 C20 F3 106.0(4) . . ?
F1 C20 F3 105.4(4) . . ?
F2 C20 C3 113.4(4) . . ?
F1 C20 C3 112.3(4) . . ?
F3 C20 C3 111.9(4) . . ?
F6 C21 F4 108.9(6) . . ?
F6 C21 F5 103.3(5) . . ?
F4 C21 F5 105.8(5) . . ?
F6 C21 C15 113.5(5) . . ?
F4 C21 C15 114.2(5) . . ?
F5 C21 C15 110.4(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
C11 C12 C13 C14 1.4(7) . . . . ?
Cl2 C12 C13 C14 -178.4(4) . . . . ?
C12 C13 C14 C15 -0.7(7) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C13 C14 C15 C21 178.1(5) . . . . ?
C14 C15 C16 C11 -1.2(7) . . . . ?
C21 C15 C16 C11 -178.6(5) . . . . ?
C13 C12 C11 C16 -2.0(7) . . . . ?
Cl2 C12 C11 C16 177.9(3) . . . . ?
C13 C12 C11 C10 -179.2(4) . . . . ?
Cl2 C12 C11 C10 0.7(6) . . . . ?
C15 C16 C11 C12 1.8(6) . . . . ?
C15 C16 C11 C10 179.1(4) . . . . ?
C9 N1 C10 C11 -176.8(4) . . . . ?
Re1 N1 C10 C11 2.6(6) . . . . ?
C12 C11 C10 N1 -105.2(5) . . . . ?
C16 C11 C10 N1 77.6(6) . . . . ?
C10 N1 C9 C8 136.4(4) . . . . ?
Re1 N1 C9 C8 -43.1(4) . . . . ?
C7 N2 C8 C9 143.4(4) . . . . ?
Re1 N2 C8 C9 -43.3(4) . . . . ?
N1 C9 C8 N2 56.7(4) . . . . ?
C8 N2 C7 C1 -178.2(4) . . . . ?
Re1 N2 C7 C1 10.3(6) . . . . ?
N2 C7 C1 C2 74.9(6) . . . . ?
N2 C7 C1 C6 -108.6(5) . . . . ?
C2 C1 C6 C5 -0.9(7) . . . . ?
C7 C1 C6 C5 -177.5(5) . . . . ?
C2 C1 C6 Cl1 -177.7(3) . . . . ?
C7 C1 C6 Cl1 5.7(6) . . . . ?
C1 C6 C5 C4 1.2(8) . . . . ?
Cl1 C6 C5 C4 177.9(4) . . . . ?
C6 C5 C4 C3 -1.1(8) . . . . ?
C5 C4 C3 C2 0.9(7) . . . . ?
C5 C4 C3 C20 -177.9(5) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
C7 C1 C2 C3 177.2(4) . . . . ?
C4 C3 C2 C1 -0.6(7) . . . . ?
C20 C3 C2 C1 178.1(4) . . . . ?
C4 C3 C20 F2 -157.5(5) . . . . ?
C2 C3 C20 F2 23.8(7) . . . . ?
C4 C3 C20 F1 -35.6(7) . . . . ?
C2 C3 C20 F1 145.7(5) . . . . ?
C4 C3 C20 F3 82.7(6) . . . . ?
C2 C3 C20 F3 -96.0(5) . . . . ?
C16 C15 C21 F6 118.4(6) . . . . ?
C14 C15 C21 F6 -59.1(8) . . . . ?
C16 C15 C21 F4 -7.2(8) . . . . ?
C14 C15 C21 F4 175.4(5) . . . . ?
C16 C15 C21 F5 -126.2(6) . . . . ?
C14 C15 C21 F5 56.3(7) . . . . ?

_refine_diff_density_max         1.207
_refine_diff_density_min         -1.684
_refine_diff_density_rms         0.188



