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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_ren513b
_database_code_depnum_ccdc_archive 'CCDC 1501825'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl3 N2 O3 Re'
_chemical_formula_sum            'C18 H12 Cl3 N2 O3 Re'
_chemical_formula_weight         596.85

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.8752(5)
_cell_length_b                   32.4799(13)
_cell_length_c                   10.9891(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.199(3)
_cell_angle_gamma                90
_cell_volume                     3842.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    12244
_cell_measurement_theta_min      3.7870
_cell_measurement_theta_max      28.8600

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.064
_exptl_crystal_F_000             2272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    6.764
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.18277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28790
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.412
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             6774
_reflns_number_gt                5687
_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       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0219P)²+33.3746P] 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         6774
_refine_ls_number_parameters     493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_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 0.29509(4) 0.02538(2) 0.21430(3) 0.03611(11) Uani 1 1 d . . . . .
Re2 Re 0.19424(4) -0.20677(2) 0.10447(3) 0.04044(12) Uani 1 1 d . . . . .
N1 N 0.1452(7) 0.0622(2) 0.2713(6) 0.0354(17) Uani 1 1 d . . . . .
N2 N 0.2478(6) -0.0051(2) 0.3814(6) 0.0338(17) Uani 1 1 d . . . . .
N3 N 0.2250(6) -0.2673(2) 0.0215(6) 0.0359(17) Uani 1 1 d . . . . .
N4 N 0.2829(7) -0.1931(2) -0.0579(7) 0.0397(18) Uani 1 1 d . . . . .
O2 O 0.3606(9) 0.0776(3) 0.0010(8) 0.089(3) Uani 1 1 d . . . . .
O1 O 0.5297(9) -0.0210(3) 0.1743(11) 0.105(4) Uani 1 1 d . . . . .
O3 O 0.1419(9) -0.0321(3) 0.0339(7) 0.073(2) Uani 1 1 d . . . . .
O4 O 0.1225(10) -0.1222(3) 0.1927(9) 0.098(3) Uani 1 1 d . . . . .
O5 O 0.0616(9) -0.2308(3) 0.3199(8) 0.085(3) Uani 1 1 d . . . . .
O6 O 0.4337(8) -0.2002(3) 0.2803(8) 0.087(3) Uani 1 1 d . . . . .
C1 C 0.4400(11) -0.0048(4) 0.1893(11) 0.064(3) Uani 1 1 d . . . . .
C2 C 0.3359(11) 0.0581(3) 0.0846(10) 0.055(3) Uani 1 1 d . . . . .
C3 C 0.1956(10) -0.0098(3) 0.1020(9) 0.048(3) Uani 1 1 d . . . . .
C4 C 0.0846(8) 0.0935(3) 0.2119(8) 0.038(2) Uani 1 1 d . . . . .
C5 C 0.0216(9) 0.1228(3) 0.2735(9) 0.045(2) Uani 1 1 d . . . . .
H5 H -0.0161 0.1452 0.2307 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0154(9) 0.1185(3) 0.3955(9) 0.045(2) Uani 1 1 d . . . . .
C7 C 0.0653(8) 0.0838(3) 0.4587(8) 0.037(2) Uani 1 1 d . . . . .
C8 C 0.0547(9) 0.0741(3) 0.5835(8) 0.044(2) Uani 1 1 d . . . . .
H8 H 0.0123 0.0925 0.6274 0.052 Uiso 1 1 calc R U . . .
C9 C 0.1026(9) 0.0401(3) 0.6411(8) 0.045(2) Uani 1 1 d . . . . .
C10 C 0.1663(8) 0.0107(3) 0.5741(7) 0.036(2) Uani 1 1 d . . . . .
C11 C 0.2163(8) -0.0276(3) 0.6186(8) 0.038(2) Uani 1 1 d . . . . .
C12 C 0.2722(9) -0.0538(3) 0.5454(9) 0.044(2) Uani 1 1 d . . . . .
H12 H 0.2995 -0.0795 0.5745 0.053 Uiso 1 1 calc R U . . .
C13 C 0.2882(9) -0.0416(3) 0.4272(8) 0.040(2) Uani 1 1 d . . . . .
C14 C 0.1848(8) 0.0199(3) 0.4523(7) 0.0308(19) Uani 1 1 d . . . . .
C15 C 0.1308(8) 0.0560(3) 0.3924(7) 0.0306(19) Uani 1 1 d . . . . .
C16 C 0.0870(15) 0.0356(5) 0.7740(10) 0.091(5) Uani 1 1 d . . . . .
H16A H 0.0527 0.0605 0.8021 0.137 Uiso 1 1 calc R U . . .
H16B H 0.1663 0.0303 0.8220 0.137 Uiso 1 1 calc R U . . .
H16C H 0.0319 0.0130 0.7831 0.137 Uiso 1 1 calc R U . . .
C17 C 0.0833(10) 0.0987(4) 0.0768(8) 0.057(3) Uani 1 1 d . . . . .
H17A H 0.0152 0.1162 0.0444 0.085 Uiso 1 1 calc R U . . .
H17B H 0.0739 0.0723 0.0372 0.085 Uiso 1 1 calc R U . . .
H17C H 0.1599 0.1110 0.0617 0.085 Uiso 1 1 calc R U . . .
C18 C 0.3530(11) -0.0707(3) 0.3532(10) 0.060(3) Uani 1 1 d . . . . .
H18A H 0.4393 -0.0634 0.3601 0.090 Uiso 1 1 calc R U . . .
H18B H 0.3161 -0.0692 0.2686 0.090 Uiso 1 1 calc R U . . .
H18C H 0.3455 -0.0982 0.3832 0.090 Uiso 1 1 calc R U . . .
Cl1 Cl 0.4235(2) 0.07168(7) 0.3610(2) 0.0455(6) Uani 1 1 d . . . . .
Cl2 Cl -0.0528(3) 0.15668(11) 0.4718(3) 0.0798(10) Uani 1 1 d . . . . .
Cl3 Cl 0.2094(3) -0.04499(9) 0.7655(2) 0.0637(8) Uani 1 1 d . . . . .
Cl4 Cl 0.0021(2) -0.20867(7) -0.0478(2) 0.0438(6) Uani 1 1 d . . . . .
Cl5 Cl 0.3850(3) -0.17379(10) -0.4373(3) 0.0689(8) Uani 1 1 d . . . . .
Cl6 Cl 0.1599(3) -0.38012(9) -0.2148(3) 0.0712(8) Uani 1 1 d . . . . .
C0AA C 0.2715(8) -0.2245(3) -0.1423(8) 0.038(2) Uani 1 1 d . . . . .
C1AA C 0.2373(8) -0.2643(3) -0.1014(8) 0.036(2) Uani 1 1 d . . . . .
C19 C 0.1531(11) -0.1530(4) 0.1580(10) 0.060(3) Uani 1 1 d . . . . .
C20 C 0.1095(11) -0.2236(4) 0.2380(10) 0.056(3) Uani 1 1 d . . . . .
C21 C 0.3500(12) -0.2040(3) 0.2146(10) 0.057(3) Uani 1 1 d . . . . .
C22 C 0.2098(8) -0.3045(3) 0.0687(9) 0.042(2) Uani 1 1 d . . . . .
C23 C 0.1938(9) -0.3386(3) -0.0069(10) 0.047(2) Uani 1 1 d . . . . .
H23 H 0.1806 -0.3642 0.0273 0.057 Uiso 1 1 calc R U . . .
C24 C 0.1967(9) -0.3358(3) -0.1306(10) 0.044(2) Uani 1 1 d . . . . .
C25 C 0.2215(9) -0.2979(3) -0.1853(9) 0.043(2) Uani 1 1 d . . . . .
C26 C 0.2347(11) -0.2904(3) -0.3127(10) 0.057(3) Uani 1 1 d . . . . .
C27 C 0.2722(10) -0.2530(3) -0.3462(9) 0.054(3) Uani 1 1 d . . . . .
H27 H 0.2832 -0.2489 -0.4277 0.065 Uiso 1 1 calc R U . . .
C28 C 0.2954(9) -0.2198(3) -0.2631(9) 0.043(2) Uani 1 1 d . . . . .
C29 C 0.3467(9) -0.1816(3) -0.2919(9) 0.048(3) Uani 1 1 d . . . . .
C30 C 0.3659(9) -0.1519(3) -0.2077(10) 0.054(3) Uani 1 1 d . . . . .
H30 H 0.4027 -0.1273 -0.2269 0.065 Uiso 1 1 calc R U . . .
C31 C 0.3310(10) -0.1573(3) -0.0886(9) 0.048(2) Uani 1 1 d . . . . .
C32 C 0.2115(17) -0.3221(5) -0.4154(13) 0.115(7) Uani 1 1 d . . . . .
H32A H 0.2693 -0.3444 -0.3986 0.172 Uiso 1 1 calc R U . . .
H32B H 0.2223 -0.3094 -0.4921 0.172 Uiso 1 1 calc R U . . .
H32C H 0.1283 -0.3324 -0.4203 0.172 Uiso 1 1 calc R U . . .
C33 C 0.3484(13) -0.1222(3) 0.0010(11) 0.071(4) Uani 1 1 d . . . . .
H33A H 0.4010 -0.1018 -0.0279 0.106 Uiso 1 1 calc R U . . .
H33B H 0.3862 -0.1322 0.0798 0.106 Uiso 1 1 calc R U . . .
H33C H 0.2691 -0.1103 0.0086 0.106 Uiso 1 1 calc R U . . .
C34 C 0.2099(11) -0.3094(3) 0.2021(9) 0.059(3) Uani 1 1 d . . . . .
H34A H 0.1286 -0.3034 0.2219 0.089 Uiso 1 1 calc R U . . .
H34B H 0.2691 -0.2908 0.2458 0.089 Uiso 1 1 calc R U . . .
H34C H 0.2320 -0.3372 0.2256 0.089 Uiso 1 1 calc R U . . .


_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 C2 1.881(11) . ?
Re1 C3 1.903(11) . ?
Re1 C1 1.909(11) . ?
Re1 N1 2.184(7) . ?
Re1 N2 2.211(7) . ?
Re1 Cl1 2.484(2) . ?
Re2 C19 1.917(12) . ?
Re2 C20 1.921(11) . ?
Re2 C21 1.938(12) . ?
Re2 N4 2.192(8) . ?
Re2 N3 2.213(7) . ?
Re2 Cl4 2.485(2) . ?
N1 C4 1.330(11) . ?
N1 C15 1.377(10) . ?
N2 C13 1.336(11) . ?
N2 C14 1.374(10) . ?
N3 C22 1.333(11) . ?
N3 C1AA 1.380(11) . ?
N4 C31 1.338(12) . ?
N4 C0AA 1.372(12) . ?
O2 C2 1.179(12) . ?
O1 C1 1.141(13) . ?
O3 C3 1.139(12) . ?
O4 C19 1.136(13) . ?
O5 C20 1.126(12) . ?
O6 C21 1.085(12) . ?
C4 C5 1.402(13) . ?
C4 C17 1.493(12) . ?
C5 C6 1.359(13) . ?
C6 C7 1.392(13) . ?
C6 Cl2 1.724(10) . ?
C7 C15 1.414(12) . ?
C7 C8 1.428(12) . ?
C8 C9 1.343(13) . ?
C9 C10 1.441(13) . ?
C9 C16 1.501(13) . ?
C10 C14 1.413(11) . ?
C10 C11 1.419(13) . ?
C11 C12 1.370(13) . ?
C11 Cl3 1.722(8) . ?
C12 C13 1.392(12) . ?
C13 C18 1.489(13) . ?
C14 C15 1.430(12) . ?
Cl5 C29 1.726(10) . ?
Cl6 C24 1.727(10) . ?
C0AA C28 1.397(13) . ?
C0AA C1AA 1.433(12) . ?
C1AA C25 1.425(13) . ?
C22 C23 1.382(14) . ?
C22 C34 1.475(13) . ?
C23 C24 1.368(14) . ?
C24 C25 1.413(13) . ?
C25 C26 1.448(13) . ?
C26 C27 1.349(15) . ?
C26 C32 1.520(16) . ?
C27 C28 1.412(14) . ?
C28 C29 1.416(14) . ?
C29 C30 1.332(15) . ?
C30 C31 1.424(14) . ?
C31 C33 1.500(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Re1 C3 91.2(4) . . ?
C2 Re1 C1 83.8(5) . . ?
C3 Re1 C1 90.2(5) . . ?
C2 Re1 N1 100.1(4) . . ?
C3 Re1 N1 97.8(4) . . ?
C1 Re1 N1 171.0(4) . . ?
C2 Re1 N2 172.1(4) . . ?
C3 Re1 N2 95.3(3) . . ?
C1 Re1 N2 100.6(4) . . ?
N1 Re1 N2 74.7(3) . . ?
C2 Re1 Cl1 88.8(3) . . ?
C3 Re1 Cl1 179.6(3) . . ?
C1 Re1 Cl1 90.3(4) . . ?
N1 Re1 Cl1 81.73(19) . . ?
N2 Re1 Cl1 84.73(19) . . ?
C19 Re2 C20 82.4(5) . . ?
C19 Re2 C21 89.3(5) . . ?
C20 Re2 C21 90.4(5) . . ?
C19 Re2 N4 102.4(4) . . ?
C20 Re2 N4 174.2(4) . . ?
C21 Re2 N4 93.0(4) . . ?
C19 Re2 N3 172.8(4) . . ?
C20 Re2 N3 100.3(4) . . ?
C21 Re2 N3 97.3(4) . . ?
N4 Re2 N3 74.6(3) . . ?
C19 Re2 Cl4 91.1(3) . . ?
C20 Re2 Cl4 93.4(3) . . ?
C21 Re2 Cl4 176.2(3) . . ?
N4 Re2 Cl4 83.2(2) . . ?
N3 Re2 Cl4 82.09(19) . . ?
C4 N1 C15 118.0(7) . . ?
C4 N1 Re1 128.0(6) . . ?
C15 N1 Re1 113.0(6) . . ?
C13 N2 C14 118.3(7) . . ?
C13 N2 Re1 127.4(6) . . ?
C14 N2 Re1 113.6(5) . . ?
C22 N3 C1AA 118.7(8) . . ?
C22 N3 Re2 127.6(6) . . ?
C1AA N3 Re2 112.4(6) . . ?
C31 N4 C0AA 118.5(8) . . ?
C31 N4 Re2 127.9(7) . . ?
C0AA N4 Re2 113.0(6) . . ?
O1 C1 Re1 176.6(11) . . ?
O2 C2 Re1 178.1(10) . . ?
O3 C3 Re1 176.2(10) . . ?
N1 C4 C5 121.6(8) . . ?
N1 C4 C17 120.6(8) . . ?
C5 C4 C17 117.8(9) . . ?
C6 C5 C4 120.2(9) . . ?
C5 C6 C7 120.3(9) . . ?
C5 C6 Cl2 119.5(8) . . ?
C7 C6 Cl2 120.2(7) . . ?
C6 C7 C15 116.7(8) . . ?
C6 C7 C8 125.3(8) . . ?
C15 C7 C8 118.0(8) . . ?
C9 C8 C7 123.7(8) . . ?
C8 C9 C10 119.1(8) . . ?
C8 C9 C16 116.7(10) . . ?
C10 C9 C16 124.3(10) . . ?
C14 C10 C11 114.3(8) . . ?
C14 C10 C9 119.3(8) . . ?
C11 C10 C9 126.4(8) . . ?
C12 C11 C10 121.5(8) . . ?
C12 C11 Cl3 115.5(7) . . ?
C10 C11 Cl3 123.0(7) . . ?
C11 C12 C13 119.8(9) . . ?
N2 C13 C12 121.7(9) . . ?
N2 C13 C18 120.9(8) . . ?
C12 C13 C18 117.4(9) . . ?
N2 C14 C10 124.2(8) . . ?
N2 C14 C15 115.4(7) . . ?
C10 C14 C15 120.3(8) . . ?
N1 C15 C7 122.7(8) . . ?
N1 C15 C14 117.9(7) . . ?
C7 C15 C14 119.4(7) . . ?
N4 C0AA C28 123.3(9) . . ?
N4 C0AA C1AA 117.4(8) . . ?
C28 C0AA C1AA 119.2(9) . . ?
N3 C1AA C25 124.0(8) . . ?
N3 C1AA C0AA 116.0(8) . . ?
C25 C1AA C0AA 120.0(8) . . ?
O4 C19 Re2 175.6(12) . . ?
O5 C20 Re2 175.0(10) . . ?
O6 C21 Re2 174.9(12) . . ?
N3 C22 C23 120.4(9) . . ?
N3 C22 C34 120.1(9) . . ?
C23 C22 C34 119.5(9) . . ?
C24 C23 C22 121.6(9) . . ?
C23 C24 C25 121.0(9) . . ?
C23 C24 Cl6 116.1(8) . . ?
C25 C24 Cl6 122.8(8) . . ?
C24 C25 C1AA 113.9(8) . . ?
C24 C25 C26 127.5(9) . . ?
C1AA C25 C26 118.5(9) . . ?
C27 C26 C25 119.4(10) . . ?
C27 C26 C32 115.5(10) . . ?
C25 C26 C32 125.1(10) . . ?
C26 C27 C28 122.9(9) . . ?
C0AA C28 C27 119.4(9) . . ?
C0AA C28 C29 116.2(9) . . ?
C27 C28 C29 124.3(9) . . ?
C30 C29 C28 120.5(9) . . ?
C30 C29 Cl5 120.2(8) . . ?
C28 C29 Cl5 119.4(9) . . ?
C29 C30 C31 120.9(9) . . ?
N4 C31 C30 120.2(9) . . ?
N4 C31 C33 120.8(9) . . ?
C30 C31 C33 119.0(9) . . ?

_refine_diff_density_max         3.087
_refine_diff_density_min         -2.551
_refine_diff_density_rms         0.156

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_ren479e
_database_code_depnum_ccdc_archive 'CCDC 1501826'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H5 Cl4 N2 O3 Re'
_chemical_formula_sum            'C15 H5 Cl4 N2 O3 Re'
_chemical_formula_weight         589.21

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                   6.6848(5)
_cell_length_b                   20.9252(16)
_cell_length_c                   12.6551(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.710(7)
_cell_angle_gamma                90
_cell_volume                     1739.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2146
_cell_measurement_theta_min      4.1810
_cell_measurement_theta_max      29.1070

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.250
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    7.618
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8748
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.349
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3069
_reflns_number_gt                2251
_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       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0127P)²+21.9287P] 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         3069
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.233
_refine_ls_restrained_S_all      1.233
_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 0.15222(8) 0.25237(2) 0.90801(4) 0.04043(17) Uani 1 1 d . . . . .
N1 N 0.2849(15) 0.3151(4) 0.8049(7) 0.039(2) Uani 1 1 d . . . . .
N2 N -0.0104(15) 0.3423(5) 0.9072(7) 0.041(2) Uani 1 1 d . . . . .
O2 O 0.434(2) 0.1393(6) 0.8970(11) 0.115(5) Uani 1 1 d . . . . .
O3 O -0.141(2) 0.1970(7) 0.7212(11) 0.109(5) Uani 1 1 d . . . . .
O1 O -0.0526(17) 0.1764(5) 1.0649(8) 0.080(3) Uani 1 1 d . . . . .
Cl1 Cl 0.3937(5) 0.30570(17) 1.0515(3) 0.0593(9) Uani 1 1 d . . . . .
Cl2 Cl 0.5761(6) 0.4557(2) 0.6110(3) 0.0701(11) Uani 1 1 d . . . . .
Cl5 Cl -0.3038(6) 0.53589(18) 0.9025(3) 0.0713(11) Uani 1 1 d . . . . .
C2 C 0.326(3) 0.1813(8) 0.9032(12) 0.067(4) Uani 1 1 d . . . . .
C3 C -0.038(2) 0.2197(7) 0.7878(13) 0.061(4) Uani 1 1 d . . . . .
C1 C 0.021(2) 0.2052(6) 1.0053(11) 0.054(3) Uani 1 1 d . . . . .
C4 C 0.4336(19) 0.2987(7) 0.7542(10) 0.054(3) Uani 1 1 d . . . . .
H4 H 0.4796 0.2567 0.7587 0.065 Uiso 1 1 calc R U . . .
C5 C 0.525(2) 0.3433(7) 0.6933(9) 0.052(3) Uani 1 1 d . . . . .
H5 H 0.6321 0.3307 0.6608 0.062 Uiso 1 1 calc R U . . .
C6 C 0.456(2) 0.4041(7) 0.6824(9) 0.049(3) Uani 1 1 d . . . . .
C7 C 0.2877(19) 0.4224(6) 0.7310(9) 0.044(3) Uani 1 1 d . . . . .
C8 C 0.189(3) 0.4843(7) 0.7238(11) 0.063(4) Uani 1 1 d . . . . .
H8 H 0.2307 0.5156 0.6805 0.075 Uiso 0.339(10) 1 calc R U P A 1
Cl4 Cl -0.021(3) 0.5720(6) 0.7526(16) 0.123(8) Uani 0.339(10) 1 d . . P A 1
C9 C 0.041(2) 0.4975(6) 0.7776(11) 0.059(4) Uani 1 1 d . . . . .
H9 H -0.0160 0.5382 0.7719 0.071 Uiso 0.661(10) 1 calc R U P A 2
Cl3 Cl 0.2287(13) 0.5460(3) 0.6390(7) 0.105(3) Uani 0.661(10) 1 d . . P A 2
C10 C -0.0332(19) 0.4522(6) 0.8424(10) 0.044(3) Uani 1 1 d . . . . .
C11 C -0.194(2) 0.4615(6) 0.9009(11) 0.051(3) Uani 1 1 d . . . . .
C12 C -0.251(2) 0.4138(7) 0.9615(11) 0.053(3) Uani 1 1 d . . . . .
H12 H -0.3504 0.4206 1.0028 0.064 Uiso 1 1 calc R U . . .
C13 C -0.1590(18) 0.3549(7) 0.9607(9) 0.047(3) Uani 1 1 d . . . . .
H13 H -0.2036 0.3220 0.9999 0.056 Uiso 1 1 calc R U . . .
C14 C 0.0511(18) 0.3904(6) 0.8478(9) 0.040(3) Uani 1 1 d . . . . .
C15 C 0.2112(18) 0.3758(6) 0.7936(8) 0.039(3) 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 C2 1.895(16) . ?
Re1 C1 1.914(15) . ?
Re1 C3 1.919(17) . ?
Re1 N1 2.155(9) . ?
Re1 N2 2.173(10) . ?
Re1 Cl1 2.462(4) . ?
N1 C4 1.325(15) . ?
N1 C15 1.360(15) . ?
N2 C13 1.328(14) . ?
N2 C14 1.364(15) . ?
O2 C2 1.147(17) . ?
O3 C3 1.091(17) . ?
O1 C1 1.145(15) . ?
Cl2 C6 1.703(13) . ?
Cl5 C11 1.722(13) . ?
C4 C5 1.418(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.350(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.431(17) . ?
C7 C15 1.412(16) . ?
C7 C8 1.447(19) . ?
C8 C9 1.333(19) . ?
C8 Cl3 1.732(14) . ?
C8 H8 0.9300 . ?
Cl4 C9 1.628(17) . ?
C9 C10 1.402(18) . ?
C9 H9 0.9300 . ?
C10 C14 1.408(16) . ?
C10 C11 1.427(17) . ?
C11 C12 1.357(18) . ?
C12 C13 1.378(17) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.408(16) . ?

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
C2 Re1 C1 88.5(6) . . ?
C2 Re1 C3 90.9(7) . . ?
C1 Re1 C3 90.5(6) . . ?
C2 Re1 N1 97.7(5) . . ?
C1 Re1 N1 173.4(5) . . ?
C3 Re1 N1 91.4(5) . . ?
C2 Re1 N2 171.4(6) . . ?
C1 Re1 N2 99.2(5) . . ?
C3 Re1 N2 92.7(5) . . ?
N1 Re1 N2 74.4(4) . . ?
C2 Re1 Cl1 93.3(5) . . ?
C1 Re1 Cl1 94.3(4) . . ?
C3 Re1 Cl1 173.6(5) . . ?
N1 Re1 Cl1 83.3(3) . . ?
N2 Re1 Cl1 82.5(3) . . ?
C4 N1 C15 118.8(11) . . ?
C4 N1 Re1 124.4(9) . . ?
C15 N1 Re1 116.8(7) . . ?
C13 N2 C14 117.7(11) . . ?
C13 N2 Re1 126.1(8) . . ?
C14 N2 Re1 116.1(7) . . ?
O2 C2 Re1 177.5(15) . . ?
O3 C3 Re1 175.0(16) . . ?
O1 C1 Re1 178.0(13) . . ?
N1 C4 C5 121.9(13) . . ?
N1 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 120.2(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.2(12) . . ?
C5 C6 Cl2 117.8(11) . . ?
C7 C6 Cl2 122.9(11) . . ?
C15 C7 C6 116.8(11) . . ?
C15 C7 C8 116.4(11) . . ?
C6 C7 C8 126.7(12) . . ?
C9 C8 C7 121.8(13) . . ?
C9 C8 Cl3 112.0(12) . . ?
C7 C8 Cl3 125.9(11) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 122.3(13) . . ?
C8 C9 Cl4 106.5(13) . . ?
C10 C9 Cl4 131.1(13) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C14 117.9(12) . . ?
C9 C10 C11 126.3(12) . . ?
C14 C10 C11 115.7(11) . . ?
C12 C11 C10 120.7(12) . . ?
C12 C11 Cl5 119.6(10) . . ?
C10 C11 Cl5 119.6(10) . . ?
C11 C12 C13 118.8(12) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
N2 C13 C12 123.9(12) . . ?
N2 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
N2 C14 C15 116.2(10) . . ?
N2 C14 C10 123.1(11) . . ?
C15 C14 C10 120.7(11) . . ?
N1 C15 C14 116.4(10) . . ?
N1 C15 C7 122.8(11) . . ?
C14 C15 C7 120.7(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 Cl5 0.93 2.76 3.131(15) 104.9 .

_refine_diff_density_max         1.413
_refine_diff_density_min         -2.752
_refine_diff_density_rms         0.174

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_ren4120
_database_code_depnum_ccdc_archive 'CCDC 1501827'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H10 Cl2 N3 O3 Re'
_chemical_formula_sum            'C17 H10 Cl2 N3 O3 Re'
_chemical_formula_weight         561.38

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3105(3)
_cell_length_b                   9.7851(4)
_cell_length_c                   12.3202(5)
_cell_angle_alpha                84.319(3)
_cell_angle_beta                 85.261(3)
_cell_angle_gamma                67.529(4)
_cell_volume                     920.16(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3961
_cell_measurement_theta_min      4.0820
_cell_measurement_theta_max      27.7720

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.026
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    6.915
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Blessing, Acta Cryst. A51 (1995) 33-38'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7649
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0479
_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       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.883
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3248
_reflns_number_gt                2795
_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       'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)'
_computing_cell_refinement       'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_data_reduction        'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Mercury (Macrae, J.Appl.Cryst. 41 (2008) 466-470'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0119P)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         3248
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0512
_refine_ls_wR_factor_gt          0.0484
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.64014(2) 0.71041(2) 0.69907(2) 0.03442(8) Uani 1 1 d . . . . .
N1 N 0.5403(5) 0.7904(4) 0.8576(4) 0.0313(10) Uani 1 1 d . . . . .
N2 N 0.8726(4) 0.6717(4) 0.7886(4) 0.0313(10) Uani 1 1 d . . . . .
N3 N 0.9643(7) 0.9980(7) 0.7900(6) 0.0763(18) Uani 1 1 d . . . . .
O3 O 0.6391(6) 1.0041(5) 0.5882(4) 0.0763(14) Uani 1 1 d . . . . .
O1 O 0.8040(6) 0.5648(6) 0.4883(5) 0.0891(16) Uani 1 1 d . . . . .
O2 O 0.2867(5) 0.7769(5) 0.6039(4) 0.0747(14) Uani 1 1 d . . . . .
Cl1 Cl 0.65176(15) 0.47083(13) 0.79392(13) 0.0443(3) Uani 1 1 d . . . . .
Cl2 Cl 0.7062(2) 0.79698(17) 1.25009(14) 0.0619(4) Uani 1 1 d . . . . .
C3 C 0.6385(6) 0.8936(7) 0.6317(5) 0.0477(15) Uani 1 1 d . . . . .
C1 C 0.7449(7) 0.6195(6) 0.5696(6) 0.0534(16) Uani 1 1 d . . . . .
C2 C 0.4196(7) 0.7490(6) 0.6393(5) 0.0440(14) Uani 1 1 d . . . . .
C4 C 0.3710(6) 0.8463(5) 0.8927(5) 0.0376(13) Uani 1 1 d . . . . .
H4 H 0.2861 0.8644 0.8427 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3184(6) 0.8778(5) 1.0000(5) 0.0383(13) Uani 1 1 d . . . . .
H5 H 0.2002 0.9178 1.0201 0.046 Uiso 1 1 calc R U . . .
C6 C 0.4392(6) 0.8504(5) 1.0766(5) 0.0412(13) Uani 1 1 d . . . . .
H6 H 0.4042 0.8693 1.1491 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6177(6) 0.7930(5) 1.0437(5) 0.0324(12) Uani 1 1 d . . . . .
C8 C 0.7584(7) 0.7649(5) 1.1143(5) 0.0381(13) Uani 1 1 d . . . . .
C9 C 0.9265(6) 0.7123(5) 1.0774(5) 0.0401(14) Uani 1 1 d . . . . .
H9 H 1.0140 0.6967 1.1250 0.048 Uiso 1 1 calc R U . . .
C10 C 0.9714(6) 0.6804(5) 0.9662(5) 0.0328(12) Uani 1 1 d . . . . .
C11 C 1.1451(6) 0.6191(5) 0.9235(5) 0.0397(14) Uani 1 1 d . . . . .
H11 H 1.2374 0.6001 0.9680 0.048 Uiso 1 1 calc R U . . .
C12 C 1.1762(6) 0.5885(5) 0.8173(5) 0.0426(15) Uani 1 1 d . . . . .
H12 H 1.2902 0.5497 0.7883 0.051 Uiso 1 1 calc R U . . .
C13 C 1.0374(6) 0.6149(5) 0.7513(5) 0.0410(13) Uani 1 1 d . . . . .
H13 H 1.0611 0.5921 0.6788 0.049 Uiso 1 1 calc R U . . .
C14 C 0.8388(6) 0.7034(5) 0.8945(5) 0.0304(12) Uani 1 1 d . . . . .
C15 C 0.6614(5) 0.7629(5) 0.9347(4) 0.0300(11) Uani 1 1 d . . . . .
C16 C 0.9331(10) 1.1671(8) 0.6153(7) 0.089(2) Uani 1 1 d . . . . .
H16A H 1.0351 1.1277 0.5679 0.133 Uiso 1 1 calc R U . . .
H16B H 0.9200 1.2642 0.6333 0.133 Uiso 1 1 calc R U . . .
H16C H 0.8323 1.1735 0.5790 0.133 Uiso 1 1 calc R U . . .
C17 C 0.9508(8) 1.0716(8) 0.7132(7) 0.0595(18) 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 C1 1.884(7) . ?
Re1 C3 1.895(6) . ?
Re1 C2 1.919(5) . ?
Re1 N1 2.158(4) . ?
Re1 N2 2.191(4) . ?
Re1 Cl1 2.4848(13) . ?
N1 C4 1.351(6) . ?
N1 C15 1.373(6) . ?
N2 C13 1.326(6) . ?
N2 C14 1.353(6) . ?
N3 C17 1.117(9) . ?
O3 C3 1.160(6) . ?
O1 C1 1.165(7) . ?
O2 C2 1.144(6) . ?
Cl2 C8 1.722(6) . ?
C4 C5 1.383(7) . ?
C5 C6 1.368(7) . ?
C6 C7 1.411(6) . ?
C7 C15 1.393(7) . ?
C7 C8 1.440(7) . ?
C8 C9 1.347(7) . ?
C9 C10 1.422(7) . ?
C10 C14 1.406(6) . ?
C10 C11 1.413(7) . ?
C11 C12 1.353(8) . ?
C12 C13 1.394(7) . ?
C14 C15 1.428(6) . ?
C16 C17 1.432(11) . ?

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
C1 Re1 C3 89.2(3) . . ?
C1 Re1 C2 87.1(2) . . ?
C3 Re1 C2 89.7(2) . . ?
C1 Re1 N1 173.1(2) . . ?
C3 Re1 N1 96.2(2) . . ?
C2 Re1 N1 97.22(19) . . ?
C1 Re1 N2 100.2(2) . . ?
C3 Re1 N2 92.79(18) . . ?
C2 Re1 N2 172.3(2) . . ?
N1 Re1 N2 75.28(14) . . ?
C1 Re1 Cl1 92.07(19) . . ?
C3 Re1 Cl1 177.26(16) . . ?
C2 Re1 Cl1 92.83(16) . . ?
N1 Re1 Cl1 82.37(10) . . ?
N2 Re1 Cl1 84.58(10) . . ?
C4 N1 C15 116.6(5) . . ?
C4 N1 Re1 126.4(3) . . ?
C15 N1 Re1 116.3(3) . . ?
C13 N2 C14 118.7(4) . . ?
C13 N2 Re1 127.0(4) . . ?
C14 N2 Re1 114.2(3) . . ?
O3 C3 Re1 178.4(6) . . ?
O1 C1 Re1 177.6(5) . . ?
O2 C2 Re1 177.8(5) . . ?
N1 C4 C5 122.9(5) . . ?
C6 C5 C4 120.5(5) . . ?
C5 C6 C7 118.8(5) . . ?
C15 C7 C6 117.7(5) . . ?
C15 C7 C8 117.5(4) . . ?
C6 C7 C8 124.8(5) . . ?
C9 C8 C7 122.0(5) . . ?
C9 C8 Cl2 120.2(4) . . ?
C7 C8 Cl2 117.8(4) . . ?
C8 C9 C10 120.6(5) . . ?
C14 C10 C11 116.9(5) . . ?
C14 C10 C9 119.6(4) . . ?
C11 C10 C9 123.5(5) . . ?
C12 C11 C10 119.6(5) . . ?
C11 C12 C13 120.0(5) . . ?
N2 C13 C12 122.2(5) . . ?
N2 C14 C10 122.6(4) . . ?
N2 C14 C15 118.6(4) . . ?
C10 C14 C15 118.8(5) . . ?
N1 C15 C7 123.5(4) . . ?
N1 C15 C14 114.9(5) . . ?
C7 C15 C14 121.5(4) . . ?
N3 C17 C16 179.5(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 N3 0.93 2.59 3.425(8) 149.0 1_455
C12 H12 Cl1 0.93 2.81 3.664(5) 153.7 1_655
C16 H16C O2 0.96 2.47 3.269(9) 141.2 2_676
C6 H6 Cl2 0.93 2.71 3.072(6) 104.3 .

_refine_diff_density_max         0.762
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.139

_shelxl_version_number           2014/6



