# 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. 
# 
#######################################################################

data_Ren520
_database_code_depnum_ccdc_archive 'CCDC 1471443'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H19 Cl N3 O3 Re'
_chemical_formula_sum            'C30 H19 Cl N3 O3 Re'
_chemical_formula_weight         691.13

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                   14.7833(3)
_cell_length_b                   11.8128(3)
_cell_length_c                   30.1691(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.552(2)
_cell_angle_gamma                90
_cell_volume                     5179.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    14800
_cell_measurement_theta_min      3.6530
_cell_measurement_theta_max      29.2150

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    4.833
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63043
_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            30073
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.305
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             9158
_reflns_number_gt                7601
_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)+(0.0221P)²+1.5706P] 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         9158
_refine_ls_number_parameters     685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.32994(2) 0.66347(2) 0.60337(2) 0.03939(6) Uani 1 1 d . . . . .
Re2 Re 0.73955(2) 0.71296(2) 0.59925(2) 0.03958(5) Uani 1 1 d . . . . .
N1 N 0.22677(18) 0.7894(3) 0.57908(10) 0.0362(7) Uani 1 1 d . . . . .
N2 N 0.25140(18) 0.6869(3) 0.65863(10) 0.0351(7) Uani 1 1 d . . . . .
N3 N 0.3517(2) 0.4760(4) 0.73218(13) 0.0684(11) Uani 1 1 d . . . . .
N4 N 0.84621(18) 0.5907(3) 0.62336(10) 0.0380(7) Uani 1 1 d . . . . .
N5 N 0.81491(18) 0.6886(3) 0.54289(10) 0.0350(7) Uani 1 1 d . . . . .
N6 N 0.6868(2) 0.8847(3) 0.47745(11) 0.0516(9) Uani 1 1 d . . . . .
O1 O 0.4583(2) 0.4671(3) 0.63798(11) 0.0836(11) Uani 1 1 d . . . . .
O2 O 0.3980(2) 0.6411(4) 0.51425(11) 0.0933(13) Uani 1 1 d . . . . .
O3 O 0.4790(2) 0.8370(3) 0.63631(12) 0.0819(11) Uani 1 1 d . . . . .
O4 O 0.5973(2) 0.8962(3) 0.56424(11) 0.0757(10) Uani 1 1 d . . . . .
O5 O 0.6741(2) 0.7342(4) 0.68901(11) 0.0917(13) Uani 1 1 d . . . . .
O6 O 0.5881(2) 0.5399(3) 0.56892(12) 0.0807(11) Uani 1 1 d . . . . .
Cl1 Cl 0.20651(6) 0.52283(9) 0.57762(4) 0.0524(3) Uani 1 1 d . . . . .
Cl2 Cl 0.86565(6) 0.85336(9) 0.62251(4) 0.0523(3) Uani 1 1 d . . . . .
C1 C 0.4113(3) 0.5432(4) 0.62596(14) 0.0539(11) Uani 1 1 d . . . . .
C2 C 0.3745(3) 0.6490(4) 0.54845(15) 0.0559(12) Uani 1 1 d . . . . .
C3 C 0.4238(3) 0.7731(5) 0.62436(14) 0.0541(12) Uani 1 1 d . . . . .
C4 C 0.2250(2) 0.8524(4) 0.54174(13) 0.0443(10) Uani 1 1 d . . . . .
H4 H 0.2737 0.8463 0.5262 0.053 Uiso 1 1 calc R U . . .
C5 C 0.1545(3) 0.9253(4) 0.52559(13) 0.0487(10) Uani 1 1 d . . . . .
H5 H 0.1551 0.9676 0.4996 0.058 Uiso 1 1 calc R U . . .
C6 C 0.0833(3) 0.9344(4) 0.54847(13) 0.0501(11) Uani 1 1 d . . . . .
H6 H 0.0340 0.9820 0.5379 0.060 Uiso 1 1 calc R U . . .
C7 C 0.0848(2) 0.8730(4) 0.58713(13) 0.0453(10) Uani 1 1 d . . . . .
H7 H 0.0370 0.8796 0.6032 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1577(2) 0.8013(3) 0.60211(11) 0.0315(8) Uani 1 1 d . . . . .
C9 C 0.1695(2) 0.7400(3) 0.64543(12) 0.0356(9) Uani 1 1 d . . . . .
C10 C 0.1010(2) 0.7383(3) 0.67111(12) 0.0387(9) Uani 1 1 d . . . . .
H10 H 0.0453 0.7741 0.6604 0.046 Uiso 1 1 calc R U . . .
C11 C 0.1140(2) 0.6838(3) 0.71280(12) 0.0387(9) Uani 1 1 d . . . . .
C12 C 0.1997(2) 0.6340(4) 0.72668(13) 0.0448(10) Uani 1 1 d . . . . .
H12 H 0.2126 0.5981 0.7546 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2666(2) 0.6368(3) 0.69970(12) 0.0378(9) Uani 1 1 d . . . . .
C14 C 0.3563(2) 0.5831(4) 0.71730(12) 0.0430(10) Uani 1 1 d . . . . .
C15 C 0.4365(2) 0.6412(4) 0.72160(13) 0.0483(11) Uani 1 1 d . . . . .
H15 H 0.4371 0.7160 0.7120 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5161(3) 0.5880(5) 0.74019(16) 0.0705(15) Uani 1 1 d . . . . .
H16 H 0.5717 0.6269 0.7437 0.085 Uiso 1 1 calc R U . . .
C17 C 0.5146(3) 0.4788(6) 0.75353(17) 0.0836(18) Uani 1 1 d . . . . .
H17 H 0.5691 0.4409 0.7650 0.100 Uiso 1 1 calc R U . . .
C18 C 0.4328(4) 0.4257(5) 0.74989(18) 0.0862(18) Uani 1 1 d . . . . .
H18 H 0.4320 0.3514 0.7600 0.103 Uiso 1 1 calc R U . . .
C19 C 0.0397(2) 0.6766(3) 0.73984(12) 0.0373(9) Uani 1 1 d . . . . .
C20 C -0.0330(2) 0.7533(3) 0.73311(13) 0.0416(9) Uani 1 1 d . . . . .
H20 H -0.0337 0.8120 0.7125 0.050 Uiso 1 1 calc R U . . .
C21 C -0.1043(2) 0.7430(4) 0.75680(13) 0.0452(10) Uani 1 1 d . . . . .
H21 H -0.1523 0.7950 0.7518 0.054 Uiso 1 1 calc R U . . .
C22 C -0.1059(2) 0.6574(4) 0.78766(13) 0.0419(10) Uani 1 1 d . . . . .
C23 C -0.0327(2) 0.5816(4) 0.79444(12) 0.0456(10) Uani 1 1 d . . . . .
H23 H -0.0323 0.5228 0.8149 0.055 Uiso 1 1 calc R U . . .
C24 C 0.0391(2) 0.5918(4) 0.77148(13) 0.0476(10) Uani 1 1 d . . . . .
H24 H 0.0880 0.5411 0.7773 0.057 Uiso 1 1 calc R U . . .
C25 C -0.1846(3) 0.6445(4) 0.81197(13) 0.0504(11) Uani 1 1 d . . . . .
C26 C -0.2272(3) 0.7393(5) 0.82604(17) 0.0773(16) Uani 1 1 d . . . . .
H26 H -0.2073 0.8115 0.8201 0.093 Uiso 1 1 calc R U . . .
C27 C -0.2995(4) 0.7254(7) 0.8489(2) 0.103(2) Uani 1 1 d . . . . .
H27 H -0.3269 0.7889 0.8590 0.123 Uiso 1 1 calc R U . . .
C28 C -0.3309(4) 0.6217(9) 0.8569(2) 0.115(3) Uani 1 1 d . . . . .
H28 H -0.3801 0.6140 0.8720 0.138 Uiso 1 1 calc R U . . .
C29 C -0.2904(4) 0.5281(7) 0.8428(2) 0.108(3) Uani 1 1 d . . . . .
H29 H -0.3120 0.4564 0.8481 0.130 Uiso 1 1 calc R U . . .
C30 C -0.2171(3) 0.5399(5) 0.82050(17) 0.0763(16) Uani 1 1 d . . . . .
H30 H -0.1895 0.4756 0.8112 0.092 Uiso 1 1 calc R U . . .
C31 C 0.6519(3) 0.8280(4) 0.57616(14) 0.0501(11) Uani 1 1 d . . . . .
C32 C 0.6975(3) 0.7270(4) 0.65419(16) 0.0573(12) Uani 1 1 d . . . . .
C33 C 0.6458(3) 0.6040(4) 0.57988(14) 0.0548(12) Uani 1 1 d . . . . .
C34 C 0.8508(2) 0.5308(4) 0.66137(13) 0.0461(10) Uani 1 1 d . . . . .
H34 H 0.8043 0.5390 0.6781 0.055 Uiso 1 1 calc R U . . .
C35 C 0.9224(3) 0.4576(4) 0.67641(14) 0.0532(11) Uani 1 1 d . . . . .
H35 H 0.9232 0.4152 0.7025 0.064 Uiso 1 1 calc R U . . .
C36 C 0.9919(3) 0.4482(4) 0.65254(14) 0.0504(11) Uani 1 1 d . . . . .
H36 H 1.0416 0.4007 0.6627 0.060 Uiso 1 1 calc R U . . .
C37 C 0.9882(2) 0.5089(3) 0.61368(13) 0.0441(10) Uani 1 1 d . . . . .
H37 H 1.0350 0.5026 0.5970 0.053 Uiso 1 1 calc R U . . .
C38 C 0.9140(2) 0.5797(3) 0.59951(11) 0.0328(8) Uani 1 1 d . . . . .
C39 C 0.8991(2) 0.6399(3) 0.55567(12) 0.0350(9) Uani 1 1 d . . . . .
C40 C 0.9656(2) 0.6465(3) 0.52934(12) 0.0372(9) Uani 1 1 d . . . . .
H40 H 1.0224 0.6124 0.5393 0.045 Uiso 1 1 calc R U . . .
C41 C 0.9499(2) 0.7033(3) 0.48810(12) 0.0358(9) Uani 1 1 d . . . . .
C42 C 0.8610(2) 0.7456(3) 0.47443(12) 0.0392(9) Uani 1 1 d . . . . .
H42 H 0.8454 0.7809 0.4465 0.047 Uiso 1 1 calc R U . . .
C43 C 0.7957(2) 0.7360(3) 0.50177(12) 0.0362(9) Uani 1 1 d . . . . .
C44 C 0.6994(2) 0.7746(4) 0.48430(12) 0.0386(9) Uani 1 1 d . . . . .
C45 C 0.6302(2) 0.6962(4) 0.47410(14) 0.0503(11) Uani 1 1 d . . . . .
H45 H 0.6424 0.6195 0.4791 0.060 Uiso 1 1 calc R U . . .
C46 C 0.5427(3) 0.7325(5) 0.45633(14) 0.0593(13) Uani 1 1 d . . . . .
H46 H 0.4950 0.6810 0.4483 0.071 Uiso 1 1 calc R U . . .
C47 C 0.5275(3) 0.8461(5) 0.45072(15) 0.0622(13) Uani 1 1 d . . . . .
H47 H 0.4687 0.8735 0.4398 0.075 Uiso 1 1 calc R U . . .
C48 C 0.5997(3) 0.9184(4) 0.46125(15) 0.0613(12) Uani 1 1 d . . . . .
H48 H 0.5885 0.9955 0.4571 0.074 Uiso 1 1 calc R U . . .
C49 C 1.0229(2) 0.7180(3) 0.46054(12) 0.0372(9) Uani 1 1 d . . . . .
C50 C 1.1061(2) 0.6588(3) 0.47061(13) 0.0414(9) Uani 1 1 d . . . . .
H50 H 1.1148 0.6061 0.4939 0.050 Uiso 1 1 calc R U . . .
C51 C 1.1754(2) 0.6776(3) 0.44643(13) 0.0419(10) Uani 1 1 d . . . . .
H51 H 1.2295 0.6359 0.4535 0.050 Uiso 1 1 calc R U . . .
C52 C 1.1671(2) 0.7566(3) 0.41202(12) 0.0400(9) Uani 1 1 d . . . . .
C53 C 1.0840(3) 0.8155(4) 0.40223(14) 0.0490(11) Uani 1 1 d . . . . .
H53 H 1.0759 0.8701 0.3796 0.059 Uiso 1 1 calc R U . . .
C54 C 1.0134(3) 0.7944(4) 0.42545(13) 0.0478(10) Uani 1 1 d . . . . .
H54 H 0.9580 0.8329 0.4172 0.057 Uiso 1 1 calc R U . . .
C55 C 1.2416(2) 0.7799(4) 0.38620(13) 0.0418(9) Uani 1 1 d . . . . .
C56 C 1.2977(3) 0.6931(4) 0.37609(15) 0.0557(12) Uani 1 1 d . . . . .
H56 H 1.2895 0.6199 0.3860 0.067 Uiso 1 1 calc R U . . .
C57 C 1.3658(3) 0.7149(5) 0.35125(16) 0.0683(14) Uani 1 1 d . . . . .
H57 H 1.4024 0.6560 0.3441 0.082 Uiso 1 1 calc R U . . .
C58 C 1.3797(3) 0.8230(6) 0.33711(16) 0.0709(15) Uani 1 1 d . . . . .
H58 H 1.4256 0.8374 0.3205 0.085 Uiso 1 1 calc R U . . .
C59 C 1.3260(3) 0.9087(5) 0.34755(15) 0.0668(13) Uani 1 1 d . . . . .
H59 H 1.3356 0.9821 0.3383 0.080 Uiso 1 1 calc R U . . .
C60 C 1.2575(3) 0.8875(4) 0.37172(15) 0.0586(12) Uani 1 1 d . . . . .
H60 H 1.2211 0.9471 0.3784 0.070 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 1.899(5) . ?
Re1 C1 1.905(5) . ?
Re1 C3 1.919(5) . ?
Re1 N1 2.160(3) . ?
Re1 N2 2.216(3) . ?
Re1 Cl1 2.4848(11) . ?
Re2 C32 1.881(5) . ?
Re2 C33 1.902(5) . ?
Re2 C31 1.918(5) . ?
Re2 N4 2.164(3) . ?
Re2 N5 2.216(3) . ?
Re2 Cl2 2.4979(10) . ?
N1 C8 1.344(4) . ?
N1 C4 1.347(5) . ?
N2 C9 1.357(4) . ?
N2 C13 1.354(5) . ?
N3 C14 1.348(5) . ?
N3 C18 1.357(6) . ?
N4 C38 1.343(4) . ?
N4 C34 1.338(5) . ?
N5 C43 1.343(5) . ?
N5 C39 1.362(4) . ?
N6 C44 1.325(5) . ?
N6 C48 1.351(5) . ?
O1 C1 1.154(5) . ?
O2 C2 1.151(5) . ?
O3 C3 1.121(5) . ?
O4 C31 1.150(5) . ?
O5 C32 1.167(5) . ?
O6 C33 1.144(5) . ?
C4 C5 1.371(5) . ?
C5 C6 1.364(5) . ?
C6 C7 1.370(5) . ?
C7 C8 1.380(5) . ?
C8 C9 1.476(5) . ?
C9 C10 1.383(5) . ?
C10 C11 1.394(5) . ?
C11 C12 1.390(5) . ?
C11 C19 1.486(5) . ?
C12 C13 1.391(5) . ?
C13 C14 1.478(5) . ?
C14 C15 1.355(5) . ?
C15 C16 1.362(6) . ?
C16 C17 1.353(7) . ?
C17 C18 1.349(7) . ?
C19 C24 1.384(5) . ?
C19 C20 1.393(5) . ?
C20 C21 1.383(5) . ?
C21 C22 1.377(6) . ?
C22 C23 1.390(5) . ?
C22 C25 1.493(5) . ?
C23 C24 1.375(5) . ?
C25 C30 1.367(7) . ?
C25 C26 1.389(7) . ?
C26 C27 1.384(7) . ?
C27 C28 1.348(10) . ?
C28 C29 1.363(10) . ?
C29 C30 1.382(6) . ?
C34 C35 1.377(5) . ?
C35 C36 1.363(5) . ?
C36 C37 1.367(5) . ?
C37 C38 1.383(5) . ?
C38 C39 1.482(5) . ?
C39 C40 1.375(5) . ?
C40 C41 1.395(5) . ?
C41 C42 1.396(5) . ?
C41 C49 1.488(5) . ?
C42 C43 1.385(5) . ?
C43 C44 1.496(5) . ?
C44 C45 1.372(5) . ?
C45 C46 1.376(5) . ?
C46 C47 1.365(7) . ?
C47 C48 1.357(6) . ?
C49 C54 1.379(5) . ?
C49 C50 1.399(5) . ?
C50 C51 1.381(5) . ?
C51 C52 1.384(5) . ?
C52 C53 1.396(5) . ?
C52 C55 1.486(5) . ?
C53 C54 1.381(5) . ?
C55 C60 1.379(6) . ?
C55 C56 1.388(5) . ?
C56 C57 1.386(6) . ?
C57 C58 1.373(7) . ?
C58 C59 1.360(7) . ?
C59 C60 1.375(6) . ?

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 87.02(17) . . ?
C2 Re1 C3 90.18(18) . . ?
C1 Re1 C3 90.82(19) . . ?
C2 Re1 N1 95.86(15) . . ?
C1 Re1 N1 174.37(15) . . ?
C3 Re1 N1 94.00(15) . . ?
C2 Re1 N2 168.64(14) . . ?
C1 Re1 N2 101.97(14) . . ?
C3 Re1 N2 96.55(14) . . ?
N1 Re1 N2 74.61(11) . . ?
C2 Re1 Cl1 91.12(14) . . ?
C1 Re1 Cl1 89.59(14) . . ?
C3 Re1 Cl1 178.65(12) . . ?
N1 Re1 Cl1 85.53(8) . . ?
N2 Re1 Cl1 82.11(8) . . ?
C32 Re2 C33 89.47(19) . . ?
C32 Re2 C31 86.97(17) . . ?
C33 Re2 C31 87.85(18) . . ?
C32 Re2 N4 95.79(15) . . ?
C33 Re2 N4 95.54(15) . . ?
C31 Re2 N4 175.63(15) . . ?
C32 Re2 N5 168.94(14) . . ?
C33 Re2 N5 96.70(15) . . ?
C31 Re2 N5 102.37(14) . . ?
N4 Re2 N5 74.54(11) . . ?
C32 Re2 Cl2 92.51(15) . . ?
C33 Re2 Cl2 177.90(13) . . ?
C31 Re2 Cl2 92.92(13) . . ?
N4 Re2 Cl2 83.60(8) . . ?
N5 Re2 Cl2 81.23(8) . . ?
C8 N1 C4 118.4(3) . . ?
C8 N1 Re1 116.9(2) . . ?
C4 N1 Re1 124.6(2) . . ?
C9 N2 C13 117.4(3) . . ?
C9 N2 Re1 113.5(2) . . ?
C13 N2 Re1 127.7(2) . . ?
C14 N3 C18 116.6(4) . . ?
C38 N4 C34 118.8(3) . . ?
C38 N4 Re2 117.0(2) . . ?
C34 N4 Re2 124.1(2) . . ?
C43 N5 C39 117.8(3) . . ?
C43 N5 Re2 127.1(2) . . ?
C39 N5 Re2 113.6(2) . . ?
C44 N6 C48 116.3(4) . . ?
O1 C1 Re1 176.6(4) . . ?
O2 C2 Re1 177.3(4) . . ?
O3 C3 Re1 179.4(4) . . ?
N1 C4 C5 122.7(3) . . ?
C6 C5 C4 118.5(4) . . ?
C5 C6 C7 119.7(4) . . ?
C8 C7 C6 119.5(3) . . ?
N1 C8 C7 121.1(3) . . ?
N1 C8 C9 115.4(3) . . ?
C7 C8 C9 123.3(3) . . ?
N2 C9 C10 122.3(3) . . ?
N2 C9 C8 116.2(3) . . ?
C10 C9 C8 121.5(3) . . ?
C9 C10 C11 121.2(3) . . ?
C12 C11 C10 115.8(3) . . ?
C12 C11 C19 122.3(3) . . ?
C10 C11 C19 121.8(3) . . ?
C13 C12 C11 121.3(4) . . ?
N2 C13 C12 122.0(3) . . ?
N2 C13 C14 120.2(3) . . ?
C12 C13 C14 117.8(3) . . ?
N3 C14 C15 122.6(4) . . ?
N3 C14 C13 115.2(3) . . ?
C15 C14 C13 121.9(4) . . ?
C14 C15 C16 118.8(5) . . ?
C17 C16 C15 120.2(5) . . ?
C18 C17 C16 118.8(5) . . ?
C17 C18 N3 122.9(5) . . ?
C24 C19 C20 118.0(3) . . ?
C24 C19 C11 121.3(3) . . ?
C20 C19 C11 120.8(4) . . ?
C21 C20 C19 120.6(4) . . ?
C22 C21 C20 121.5(4) . . ?
C21 C22 C23 117.6(3) . . ?
C21 C22 C25 121.2(4) . . ?
C23 C22 C25 121.2(4) . . ?
C24 C23 C22 121.4(4) . . ?
C23 C24 C19 120.9(4) . . ?
C30 C25 C26 118.4(4) . . ?
C30 C25 C22 121.2(4) . . ?
C26 C25 C22 120.4(4) . . ?
C25 C26 C27 119.5(6) . . ?
C28 C27 C26 121.3(7) . . ?
C27 C28 C29 119.7(5) . . ?
C28 C29 C30 120.0(6) . . ?
C25 C30 C29 121.1(6) . . ?
O4 C31 Re2 176.4(4) . . ?
O5 C32 Re2 177.8(4) . . ?
O6 C33 Re2 178.2(4) . . ?
N4 C34 C35 122.0(4) . . ?
C36 C35 C34 119.0(4) . . ?
C37 C36 C35 119.6(4) . . ?
C36 C37 C38 119.2(3) . . ?
N4 C38 C37 121.3(3) . . ?
N4 C38 C39 115.4(3) . . ?
C37 C38 C39 123.1(3) . . ?
N5 C39 C40 121.7(3) . . ?
N5 C39 C38 115.8(3) . . ?
C40 C39 C38 122.5(3) . . ?
C39 C40 C41 121.5(3) . . ?
C42 C41 C40 115.5(3) . . ?
C42 C41 C49 122.2(3) . . ?
C40 C41 C49 122.3(3) . . ?
C43 C42 C41 121.0(3) . . ?
N5 C43 C42 122.1(3) . . ?
N5 C43 C44 118.7(3) . . ?
C42 C43 C44 119.2(3) . . ?
N6 C44 C45 123.4(3) . . ?
N6 C44 C43 116.9(3) . . ?
C45 C44 C43 119.6(4) . . ?
C44 C45 C46 119.1(4) . . ?
C45 C46 C47 118.4(4) . . ?
C48 C47 C46 119.0(4) . . ?
N6 C48 C47 123.7(5) . . ?
C54 C49 C50 117.1(3) . . ?
C54 C49 C41 121.6(3) . . ?
C50 C49 C41 121.3(3) . . ?
C51 C50 C49 120.9(4) . . ?
C52 C51 C50 122.2(3) . . ?
C51 C52 C53 116.7(3) . . ?
C51 C52 C55 123.0(3) . . ?
C53 C52 C55 120.3(4) . . ?
C54 C53 C52 121.3(4) . . ?
C53 C54 C49 121.9(3) . . ?
C60 C55 C56 117.9(4) . . ?
C60 C55 C52 121.5(4) . . ?
C56 C55 C52 120.6(4) . . ?
C57 C56 C55 120.3(5) . . ?
C58 C57 C56 120.4(4) . . ?
C59 C58 C57 119.6(4) . . ?
C58 C59 C60 120.4(5) . . ?
C59 C60 C55 121.4(4) . . ?

_refine_diff_density_max         0.601
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.080

_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_ren539
_database_code_depnum_ccdc_archive 'CCDC 1471444'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 Cl2 N3 O3 Re'
_chemical_formula_sum            'C24 H14 Cl2 N3 O3 Re'
_chemical_formula_weight         649.48

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                   9.4121(6)
_cell_length_b                   20.5407(9)
_cell_length_c                   11.8912(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.084(6)
_cell_angle_gamma                90
_cell_volume                     2229.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3605
_cell_measurement_theta_min      3.8250
_cell_measurement_theta_max      27.5150

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    5.722
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45455
_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            9767
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.317
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3933
_reflns_number_gt                3227
_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)+(0.0150P)²+4.0181P] 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         3933
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 0.19104(3) 0.39198(2) 0.52283(2) 0.03593(10) Uani 1 1 d . . . . .
N1 N 0.3357(6) 0.3633(3) 0.4142(4) 0.0384(13) Uani 1 1 d . . . . .
N2 N 0.1810(5) 0.2835(2) 0.5175(4) 0.0325(12) Uani 1 1 d . . . . .
C15 C -0.1336(6) 0.3011(3) 0.5493(5) 0.0324(14) Uani 1 1 d . . . . .
H15 H -0.1370 0.3083 0.4714 0.039 Uiso 1 1 calc R U . . .
O1 O 0.0110(6) 0.4294(3) 0.6978(5) 0.0658(15) Uani 1 1 d . . . . .
O2 O 0.2575(6) 0.5372(3) 0.5138(6) 0.0840(19) Uani 1 1 d . . . . .
O3 O -0.0693(8) 0.4064(3) 0.3165(5) 0.092(2) Uani 1 1 d . . . . .
Cl1 Cl 0.4091(2) 0.37712(10) 0.68432(16) 0.0593(5) Uani 1 1 d . . . . .
Cl2 Cl 0.2855(2) -0.14356(9) 0.49652(19) 0.0662(6) Uani 1 1 d . . . . .
C1 C 0.0740(7) 0.4142(3) 0.6297(6) 0.0464(18) Uani 1 1 d . . . . .
C2 C 0.2315(7) 0.4823(4) 0.5182(6) 0.0452(17) Uani 1 1 d . . . . .
C3 C 0.0262(8) 0.4006(3) 0.3853(8) 0.052(2) Uani 1 1 d . . . . .
C4 C 0.4055(9) 0.4055(4) 0.3608(6) 0.063(2) Uani 1 1 d . . . . .
H4 H 0.3899 0.4498 0.3688 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4986(9) 0.3863(5) 0.2952(6) 0.068(2) Uani 1 1 d . . . . .
H5 H 0.5477 0.4173 0.2618 0.081 Uiso 1 1 calc R U . . .
C6 C 0.5193(9) 0.3215(5) 0.2789(6) 0.065(2) Uani 1 1 d . . . . .
H6 H 0.5805 0.3076 0.2330 0.078 Uiso 1 1 calc R U . . .
C7 C 0.4473(8) 0.2773(4) 0.3321(6) 0.0514(19) Uani 1 1 d . . . . .
H7 H 0.4590 0.2329 0.3218 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3575(7) 0.2989(3) 0.4010(5) 0.0359(15) Uani 1 1 d . . . . .
C9 C 0.2759(6) 0.2543(3) 0.4626(5) 0.0344(15) Uani 1 1 d . . . . .
C10 C 0.2963(7) 0.1878(3) 0.4625(6) 0.0402(16) Uani 1 1 d . . . . .
H10 H 0.3630 0.1702 0.4246 0.048 Uiso 1 1 calc R U . . .
C11 C 0.2176(7) 0.1467(3) 0.5187(5) 0.0385(16) Uani 1 1 d . . . . .
C12 C 0.1216(7) 0.1766(3) 0.5743(6) 0.0422(16) Uani 1 1 d . . . . .
H12 H 0.0684 0.1514 0.6147 0.051 Uiso 1 1 calc R U . . .
C13 C 0.1042(6) 0.2444(3) 0.5703(5) 0.0328(15) Uani 1 1 d . . . . .
C14 C -0.0168(6) 0.2709(3) 0.6199(5) 0.0326(14) Uani 1 1 d . . . . .
N15 N -0.0041(7) 0.2587(4) 0.7333(5) 0.0661(19) Uani 1 1 d . . . . .
C18 C -0.1179(9) 0.2805(5) 0.7758(6) 0.078(3) Uani 1 1 d . . . . .
H18 H -0.1123 0.2744 0.8543 0.094 Uiso 1 1 calc R U . . .
C17 C -0.2383(8) 0.3103(4) 0.7105(6) 0.055(2) Uani 1 1 d . . . . .
H17 H -0.3140 0.3235 0.7429 0.066 Uiso 1 1 calc R U . . .
C16 C -0.2456(7) 0.3204(3) 0.5956(6) 0.0423(16) Uani 1 1 d . . . . .
H16 H -0.3274 0.3407 0.5489 0.051 Uiso 1 1 calc R U . . .
C19 C 0.2370(7) 0.0748(3) 0.5164(5) 0.0366(15) Uani 1 1 d . . . . .
C24 C 0.1920(9) 0.0341(4) 0.5933(8) 0.068(2) Uani 1 1 d . . . . .
H24 H 0.1508 0.0522 0.6497 0.081 Uiso 1 1 calc R U . . .
C23 C 0.2065(9) -0.0325(4) 0.5888(8) 0.070(2) Uani 1 1 d . . . . .
H23 H 0.1780 -0.0590 0.6429 0.084 Uiso 1 1 calc R U . . .
C22 C 0.2628(8) -0.0591(3) 0.5048(6) 0.0469(18) Uani 1 1 d . . . . .
C21 C 0.3065(12) -0.0210(4) 0.4288(8) 0.089(3) Uani 1 1 d . . . . .
H21 H 0.3477 -0.0394 0.3727 0.106 Uiso 1 1 calc R U . . .
C20 C 0.2905(10) 0.0458(4) 0.4333(7) 0.074(3) Uani 1 1 d . . . . .
H20 H 0.3175 0.0715 0.3776 0.088 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 1.898(7) . ?
Re1 C1 1.929(8) . ?
Re1 C3 1.969(8) . ?
Re1 N1 2.174(5) . ?
Re1 N2 2.231(5) . ?
Re1 Cl1 2.4650(18) . ?
N1 C4 1.337(8) . ?
N1 C8 1.353(8) . ?
N2 C13 1.335(7) . ?
N2 C9 1.366(7) . ?
C15 C14 1.359(8) . ?
C15 C16 1.362(8) . ?
C15 H15 0.9300 . ?
O1 C1 1.156(8) . ?
O2 C2 1.156(8) . ?
O3 C3 1.065(8) . ?
Cl2 C22 1.754(7) . ?
C4 C5 1.365(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.496(8) . ?
C9 C10 1.380(9) . ?
C10 C11 1.396(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(8) . ?
C11 C19 1.490(9) . ?
C12 C13 1.402(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.506(8) . ?
C14 N15 1.348(8) . ?
N15 C18 1.366(9) . ?
C18 C17 1.354(10) . ?
C18 H18 0.9300 . ?
C17 C16 1.367(9) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C19 C20 1.352(9) . ?
C19 C24 1.379(9) . ?
C24 C23 1.378(10) . ?
C24 H24 0.9300 . ?
C23 C22 1.354(10) . ?
C23 H23 0.9300 . ?
C22 C21 1.333(10) . ?
C21 C20 1.382(11) . ?
C21 H21 0.9300 . ?
C20 H20 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
C2 Re1 C1 86.5(3) . . ?
C2 Re1 C3 90.7(3) . . ?
C1 Re1 C3 93.7(3) . . ?
C2 Re1 N1 95.1(2) . . ?
C1 Re1 N1 175.3(2) . . ?
C3 Re1 N1 90.7(3) . . ?
C2 Re1 N2 169.5(2) . . ?
C1 Re1 N2 103.2(2) . . ?
C3 Re1 N2 92.7(2) . . ?
N1 Re1 N2 74.97(19) . . ?
C2 Re1 Cl1 90.5(2) . . ?
C1 Re1 Cl1 91.0(2) . . ?
C3 Re1 Cl1 175.2(2) . . ?
N1 Re1 Cl1 84.62(14) . . ?
N2 Re1 Cl1 85.39(13) . . ?
C4 N1 C8 118.2(6) . . ?
C4 N1 Re1 123.8(5) . . ?
C8 N1 Re1 117.9(4) . . ?
C13 N2 C9 117.0(5) . . ?
C13 N2 Re1 127.7(4) . . ?
C9 N2 Re1 115.0(4) . . ?
C14 C15 C16 118.2(6) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
O1 C1 Re1 175.9(6) . . ?
O2 C2 Re1 178.7(7) . . ?
O3 C3 Re1 174.5(8) . . ?
N1 C4 C5 122.8(8) . . ?
N1 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C4 C5 C6 119.7(7) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 118.4(7) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C8 120.0(7) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
N1 C8 C7 120.9(6) . . ?
N1 C8 C9 115.5(5) . . ?
C7 C8 C9 123.6(6) . . ?
N2 C9 C10 122.8(6) . . ?
N2 C9 C8 116.1(5) . . ?
C10 C9 C8 121.1(5) . . ?
C9 C10 C11 120.5(6) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 116.4(6) . . ?
C12 C11 C19 123.0(6) . . ?
C10 C11 C19 120.6(6) . . ?
C11 C12 C13 120.5(6) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
N2 C13 C12 122.7(6) . . ?
N2 C13 C14 120.9(5) . . ?
C12 C13 C14 116.1(5) . . ?
N15 C14 C15 124.3(5) . . ?
N15 C14 C13 115.6(6) . . ?
C15 C14 C13 119.9(5) . . ?
C14 N15 C18 115.0(6) . . ?
C17 C18 N15 123.9(6) . . ?
C17 C18 H18 118.1 . . ?
N15 C18 H18 118.1 . . ?
C18 C17 C16 118.3(6) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C15 C16 C17 120.2(6) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C20 C19 C24 116.5(6) . . ?
C20 C19 C11 121.4(6) . . ?
C24 C19 C11 122.0(6) . . ?
C23 C24 C19 121.9(7) . . ?
C23 C24 H24 119.1 . . ?
C19 C24 H24 119.1 . . ?
C22 C23 C24 119.2(7) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C21 C22 C23 120.3(7) . . ?
C21 C22 Cl2 118.7(6) . . ?
C23 C22 Cl2 121.0(6) . . ?
C22 C21 C20 120.1(7) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C19 C20 C21 122.0(7) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?

_refine_diff_density_max         0.769
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.118

_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_ren535
_database_code_depnum_ccdc_archive 'CCDC 1471445'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 Br Cl N3 O3 Re'
_chemical_formula_sum            'C24 H14 Br Cl N3 O3 Re'
_chemical_formula_weight         693.94

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'
Br Br -0.2901 2.4595 '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                   9.4203(6)
_cell_length_b                   20.6584(8)
_cell_length_c                   11.8992(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.218(6)
_cell_angle_gamma                90
_cell_volume                     2244.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3766
_cell_measurement_theta_min      3.8400
_cell_measurement_theta_max      28.9300

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.053
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    7.345
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.08504
_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            9568
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.446
_diffrn_reflns_theta_max         25.049
_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             3965
_reflns_number_gt                3286
_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)+(0.0435P)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         3965
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.69112(3) 0.60775(2) 0.02157(2) 0.03061(14) Uani 1 1 d . . . . .
Br1 Br 0.78704(10) 1.14512(4) -0.00897(8) 0.0483(2) Uani 1 1 d . . . . .
Cl1 Cl 0.9085(2) 0.62404(11) 0.18256(17) 0.0494(5) Uani 1 1 d . . . . .
O1 O 0.5111(7) 0.5701(3) 0.1955(5) 0.0588(17) Uani 1 1 d . . . . .
O2 O 0.7613(8) 0.4637(3) 0.0147(7) 0.076(2) Uani 1 1 d . . . . .
O3 O 0.4333(9) 0.5920(3) -0.1838(6) 0.079(2) Uani 1 1 d . . . . .
N1 N 0.8347(7) 0.6363(3) -0.0865(5) 0.0338(14) Uani 1 1 d . . . . .
N2 N 0.6792(6) 0.7154(3) 0.0153(4) 0.0301(14) Uani 1 1 d . . . . .
N3 N 0.4961(7) 0.7399(4) 0.2317(6) 0.0513(19) Uani 1 1 d . . . . .
C15 C 0.3666(7) 0.6972(3) 0.0483(6) 0.0257(15) Uani 1 1 d . . . . .
H15 H 0.3625 0.6899 -0.0295 0.031 Uiso 1 1 calc R U . . .
C1 C 0.5753(9) 0.5860(4) 0.1281(7) 0.0384(18) Uani 1 1 d . . . . .
C2 C 0.7327(9) 0.5182(4) 0.0184(7) 0.046(2) Uani 1 1 d . . . . .
C3 C 0.5268(9) 0.5988(4) -0.1138(9) 0.047(2) Uani 1 1 d . . . . .
C4 C 0.9062(11) 0.5941(4) -0.1400(7) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.8926 0.5499 -0.1317 0.066 Uiso 1 1 calc R U . . .
C5 C 0.9968(11) 0.6142(5) -0.2053(8) 0.058(3) Uani 1 1 d . . . . .
H5 H 1.0470 0.5837 -0.2383 0.070 Uiso 1 1 calc R U . . .
C6 C 1.0156(10) 0.6786(5) -0.2234(7) 0.052(2) Uani 1 1 d . . . . .
H6 H 1.0750 0.6926 -0.2706 0.062 Uiso 1 1 calc R U . . .
C7 C 0.9437(9) 0.7221(4) -0.1695(6) 0.0417(19) Uani 1 1 d . . . . .
H7 H 0.9548 0.7663 -0.1794 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8553(8) 0.7005(3) -0.1008(6) 0.0331(17) Uani 1 1 d . . . . .
C9 C 0.7740(8) 0.7436(3) -0.0401(6) 0.0293(16) Uani 1 1 d . . . . .
C10 C 0.7945(8) 0.8093(3) -0.0396(6) 0.0339(18) Uani 1 1 d . . . . .
H10 H 0.8609 0.8265 -0.0778 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7177(8) 0.8510(3) 0.0171(6) 0.0314(17) Uani 1 1 d . . . . .
C12 C 0.6213(8) 0.8209(3) 0.0738(6) 0.0325(17) Uani 1 1 d . . . . .
H12 H 0.5698 0.8456 0.1158 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6029(7) 0.7548(3) 0.0675(6) 0.0273(16) Uani 1 1 d . . . . .
C14 C 0.4834(7) 0.7273(3) 0.1178(6) 0.0275(16) Uani 1 1 d . . . . .
C18 C 0.3825(10) 0.7189(5) 0.2726(8) 0.061(3) Uani 1 1 d . . . . .
H18 H 0.3870 0.7259 0.3506 0.073 Uiso 1 1 calc R U . . .
C17 C 0.2632(9) 0.6887(4) 0.2084(7) 0.046(2) Uani 1 1 d . . . . .
H17 H 0.1880 0.6756 0.2413 0.055 Uiso 1 1 calc R U . . .
C16 C 0.2557(8) 0.6780(4) 0.0948(7) 0.0407(19) Uani 1 1 d . . . . .
H16 H 0.1742 0.6574 0.0485 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7351(8) 0.9215(3) 0.0146(6) 0.0293(16) Uani 1 1 d . . . . .
C20 C 0.7924(11) 0.9496(4) -0.0682(8) 0.060(3) Uani 1 1 d . . . . .
H20 H 0.8215 0.9234 -0.1222 0.072 Uiso 1 1 calc R U . . .
C21 C 0.8083(13) 1.0155(4) -0.0739(8) 0.072(3) Uani 1 1 d . . . . .
H21 H 0.8503 1.0332 -0.1300 0.086 Uiso 1 1 calc R U . . .
C22 C 0.7634(9) 1.0548(4) 0.0015(6) 0.0369(18) Uani 1 1 d . . . . .
C23 C 0.7052(10) 1.0284(4) 0.0854(8) 0.053(2) Uani 1 1 d . . . . .
H23 H 0.6755 1.0549 0.1386 0.064 Uiso 1 1 calc R U . . .
C24 C 0.6909(10) 0.9624(4) 0.0904(8) 0.054(2) Uani 1 1 d . . . . .
H24 H 0.6500 0.9448 0.1472 0.065 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 1.894(8) . ?
Re1 C1 1.919(9) . ?
Re1 C3 1.950(9) . ?
Re1 N1 2.164(6) . ?
Re1 N2 2.227(6) . ?
Re1 Cl1 2.459(2) . ?
Br1 C22 1.888(7) . ?
O1 C1 1.163(9) . ?
O2 C2 1.162(9) . ?
O3 C3 1.063(10) . ?
N1 C4 1.353(10) . ?
N1 C8 1.357(9) . ?
N2 C13 1.336(9) . ?
N2 C9 1.364(8) . ?
N3 C18 1.351(10) . ?
N3 C14 1.355(9) . ?
C15 C14 1.355(9) . ?
C15 C16 1.355(10) . ?
C15 H15 0.9300 . ?
C4 C5 1.352(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.475(10) . ?
C9 C10 1.370(10) . ?
C10 C11 1.401(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.404(10) . ?
C11 C19 1.465(10) . ?
C12 C13 1.376(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.509(9) . ?
C18 C17 1.347(11) . ?
C18 H18 0.9300 . ?
C17 C16 1.355(11) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C19 C20 1.364(11) . ?
C19 C24 1.374(11) . ?
C20 C21 1.373(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.352(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(11) . ?
C23 C24 1.373(11) . ?
C23 H23 0.9300 . ?
C24 H24 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
C2 Re1 C1 86.5(3) . . ?
C2 Re1 C3 91.0(3) . . ?
C1 Re1 C3 93.4(4) . . ?
C2 Re1 N1 95.3(3) . . ?
C1 Re1 N1 175.1(3) . . ?
C3 Re1 N1 91.1(3) . . ?
C2 Re1 N2 169.7(3) . . ?
C1 Re1 N2 102.9(3) . . ?
C3 Re1 N2 92.5(3) . . ?
N1 Re1 N2 75.0(2) . . ?
C2 Re1 Cl1 90.7(3) . . ?
C1 Re1 Cl1 91.0(2) . . ?
C3 Re1 Cl1 175.4(3) . . ?
N1 Re1 Cl1 84.45(16) . . ?
N2 Re1 Cl1 85.13(15) . . ?
C4 N1 C8 117.8(7) . . ?
C4 N1 Re1 124.1(6) . . ?
C8 N1 Re1 118.1(5) . . ?
C13 N2 C9 117.1(6) . . ?
C13 N2 Re1 128.4(4) . . ?
C9 N2 Re1 114.2(4) . . ?
C18 N3 C14 114.5(7) . . ?
C14 C15 C16 118.5(6) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
O1 C1 Re1 176.1(7) . . ?
O2 C2 Re1 178.0(8) . . ?
O3 C3 Re1 175.8(9) . . ?
C5 C4 N1 122.0(8) . . ?
C5 C4 H4 119.0 . . ?
N1 C4 H4 119.0 . . ?
C4 C5 C6 120.9(8) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 117.7(8) . . ?
C5 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C6 C7 C8 120.2(8) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N1 C8 C7 121.2(7) . . ?
N1 C8 C9 114.9(6) . . ?
C7 C8 C9 123.9(7) . . ?
N2 C9 C10 122.0(6) . . ?
N2 C9 C8 117.3(6) . . ?
C10 C9 C8 120.7(6) . . ?
C9 C10 C11 121.6(6) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C12 115.4(7) . . ?
C10 C11 C19 121.9(6) . . ?
C12 C11 C19 122.6(6) . . ?
C13 C12 C11 120.1(7) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
N2 C13 C12 123.7(6) . . ?
N2 C13 C14 119.6(6) . . ?
C12 C13 C14 116.6(6) . . ?
C15 C14 N3 123.8(6) . . ?
C15 C14 C13 120.2(6) . . ?
N3 C14 C13 115.7(6) . . ?
C17 C18 N3 124.7(8) . . ?
C17 C18 H18 117.7 . . ?
N3 C18 H18 117.7 . . ?
C18 C17 C16 118.2(7) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C17 C16 C15 120.2(7) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C20 C19 C24 116.7(7) . . ?
C20 C19 C11 120.2(7) . . ?
C24 C19 C11 123.0(6) . . ?
C19 C20 C21 121.7(8) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 120.4(8) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.6(7) . . ?
C21 C22 Br1 119.2(6) . . ?
C23 C22 Br1 121.2(6) . . ?
C22 C23 C24 119.3(8) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C19 122.3(7) . . ?
C23 C24 H24 118.8 . . ?
C19 C24 H24 118.8 . . ?

_refine_diff_density_max         1.732
_refine_diff_density_min         -2.151
_refine_diff_density_rms         0.175

_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_Ren478a
_database_code_depnum_ccdc_archive 'CCDC 1471446'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Cl N4 O3 Re'
_chemical_formula_sum            'C26 H20 Cl N4 O3 Re'
_chemical_formula_weight         658.11

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                   7.2934(3)
_cell_length_b                   11.1958(6)
_cell_length_c                   15.1296(6)
_cell_angle_alpha                91.434(4)
_cell_angle_beta                 92.141(3)
_cell_angle_gamma                107.978(4)
_cell_volume                     1173.40(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5531
_cell_measurement_theta_min      4.0240
_cell_measurement_theta_max      28.4440

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    5.329
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58195
_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            9547
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.367
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4145
_reflns_number_gt                3693
_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)+(0.0336P)²+2.6567P] 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         4145
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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 0.8902(10) 0.8252(8) 0.6228(5) 0.0456(18) Uani 1 1 d . . . . .
C2 C 0.8205(11) 1.0453(7) 0.6354(4) 0.0445(18) Uani 1 1 d . . . . .
C3 C 1.1800(11) 1.0389(7) 0.6230(5) 0.0433(17) Uani 1 1 d . . . . .
C4 C 1.0850(9) 1.2429(6) 0.7847(4) 0.0352(15) Uani 1 1 d . . . . .
H4 H 1.0375 1.2607 0.7304 0.042 Uiso 1 1 calc R U . . .
C5 C 1.1491(10) 1.3362(7) 0.8502(4) 0.0397(16) Uani 1 1 d . . . . .
H5 H 1.1467 1.4173 0.8400 0.048 Uiso 1 1 calc R U . . .
C6 C 1.2159(11) 1.3086(7) 0.9301(5) 0.0433(17) Uani 1 1 d . . . . .
H6 H 1.2577 1.3713 0.9744 0.052 Uiso 1 1 calc R U . . .
C7 C 1.2225(10) 1.1889(6) 0.9461(4) 0.0362(15) Uani 1 1 d . . . . .
H7 H 1.2657 1.1700 1.0010 0.043 Uiso 1 1 calc R U . . .
C8 C 1.1631(8) 1.0979(6) 0.8784(4) 0.0268(13) Uani 1 1 d . . . . .
C9 C 1.1816(8) 0.9715(6) 0.8802(4) 0.0261(13) Uani 1 1 d . . . . .
C10 C 1.2248(9) 0.9240(6) 0.9598(4) 0.0327(14) Uani 1 1 d . . . . .
H10 H 1.2388 0.9718 1.0122 0.039 Uiso 1 1 calc R U . . .
C11 C 1.2472(9) 0.8038(6) 0.9612(4) 0.0307(14) Uani 1 1 d . . . . .
C12 C 1.2366(9) 0.7436(6) 0.8804(4) 0.0329(14) Uani 1 1 d . . . . .
H12 H 1.2592 0.6662 0.8777 0.039 Uiso 1 1 calc R U . . .
C13 C 1.1930(9) 0.7943(6) 0.8020(5) 0.0347(15) Uani 1 1 d . . . . .
C14 C 1.1995(9) 0.7272(6) 0.7173(4) 0.0333(15) Uani 1 1 d . . . . .
C15 C 1.3128(10) 0.7880(7) 0.6507(4) 0.0371(15) Uani 1 1 d . . . . .
H15 H 1.3835 0.8726 0.6577 0.044 Uiso 1 1 calc R U . . .
C16 C 1.3197(11) 0.7208(8) 0.5731(4) 0.0447(18) Uani 1 1 d . . . . .
H16 H 1.3927 0.7595 0.5267 0.054 Uiso 1 1 calc R U . . .
C17 C 1.2143(12) 0.5945(9) 0.5672(5) 0.052(2) Uani 1 1 d . . . . .
H17 H 1.2130 0.5461 0.5161 0.063 Uiso 1 1 calc R U . . .
C18 C 1.1106(11) 0.5415(7) 0.6394(5) 0.0479(18) Uani 1 1 d . . . . .
H18 H 1.0435 0.4560 0.6355 0.057 Uiso 1 1 calc R U . . .
C19 C 1.2820(9) 0.7449(6) 1.0427(4) 0.0292(13) Uani 1 1 d . . . . .
C20 C 1.3485(9) 0.8122(6) 1.1213(4) 0.0337(15) Uani 1 1 d . . . . .
H20 H 1.3676 0.8983 1.1234 0.040 Uiso 1 1 calc R U . . .
C21 C 1.3882(9) 0.7558(7) 1.1981(5) 0.0394(16) Uani 1 1 d . . . . .
H21 H 1.4339 0.8051 1.2494 0.047 Uiso 1 1 calc R U . . .
C22 C 1.3600(10) 0.6247(6) 1.1991(4) 0.0359(15) Uani 1 1 d . . . . .
C23 C 1.2824(11) 0.5558(7) 1.1200(5) 0.0446(18) Uani 1 1 d . . . . .
H23 H 1.2555 0.4690 1.1180 0.054 Uiso 1 1 calc R U . . .
C24 C 1.2454(10) 0.6150(6) 1.0449(5) 0.0410(16) Uani 1 1 d . . . . .
H24 H 1.1941 0.5661 0.9940 0.049 Uiso 1 1 calc R U . . .
C25 C 1.4805(13) 0.6352(9) 1.3522(4) 0.059(2) Uani 1 1 d . . . . .
H25A H 1.6080 0.6910 1.3444 0.089 Uiso 1 1 calc R U . . .
H25B H 1.4856 0.5776 1.3975 0.089 Uiso 1 1 calc R U . . .
H25C H 1.3979 0.6831 1.3692 0.089 Uiso 1 1 calc R U . . .
C26 C 1.3956(12) 0.4361(7) 1.2609(4) 0.051(2) Uani 1 1 d . . . . .
H26A H 1.2632 0.3856 1.2512 0.076 Uiso 1 1 calc R U . . .
H26B H 1.4488 0.4110 1.3137 0.076 Uiso 1 1 calc R U . . .
H26C H 1.4676 0.4250 1.2113 0.076 Uiso 1 1 calc R U . . .
N1 N 1.0913(7) 1.1245(5) 0.7996(4) 0.0338(12) Uani 1 1 d . . . . .
N2 N 1.1570(7) 0.9062(5) 0.8008(3) 0.0280(11) Uani 1 1 d . . . . .
N3 N 1.1010(9) 0.6040(5) 0.7127(4) 0.0450(15) Uani 1 1 d . . . . .
N4 N 1.4063(9) 0.5665(6) 1.2710(3) 0.0440(15) Uani 1 1 d . . . . .
O1 O 0.8333(9) 0.7414(5) 0.5719(3) 0.0580(15) Uani 1 1 d . . . . .
O2 O 0.7284(10) 1.0960(7) 0.6004(4) 0.082(2) Uani 1 1 d . . . . .
O3 O 1.2905(9) 1.0780(6) 0.5689(4) 0.0658(16) Uani 1 1 d . . . . .
Cl1 Cl 0.7299(2) 0.88687(17) 0.81047(12) 0.0428(4) Uani 1 1 d . . . . .
Re1 Re 0.98384(4) 0.97076(2) 0.70177(2) 0.03150(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.159(9) . ?
C1 Re1 1.925(9) . ?
C2 O2 1.130(8) . ?
C2 Re1 1.922(7) . ?
C3 O3 1.167(9) . ?
C3 Re1 1.884(8) . ?
C4 N1 1.364(8) . ?
C4 C5 1.380(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(9) . ?
C7 H7 0.9300 . ?
C8 N1 1.361(8) . ?
C8 C9 1.463(8) . ?
C9 N2 1.367(8) . ?
C9 C10 1.394(8) . ?
C10 C11 1.405(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(9) . ?
C11 C19 1.463(8) . ?
C12 C13 1.396(9) . ?
C12 H12 0.9300 . ?
C13 N2 1.357(8) . ?
C13 C14 1.478(9) . ?
C14 N3 1.343(9) . ?
C14 C15 1.382(9) . ?
C15 C16 1.389(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(11) . ?
C17 H17 0.9300 . ?
C18 N3 1.312(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(9) . ?
C19 C24 1.397(9) . ?
C20 C21 1.398(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.418(9) . ?
C21 H21 0.9300 . ?
C22 N4 1.366(8) . ?
C22 C23 1.407(10) . ?
C23 C24 1.388(9) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N4 1.428(10) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N4 1.441(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N1 Re1 2.173(6) . ?
N2 Re1 2.200(5) . ?
Cl1 Re1 2.4995(17) . ?

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
O1 C1 Re1 176.6(6) . . ?
O2 C2 Re1 175.3(7) . . ?
O3 C3 Re1 174.7(7) . . ?
N1 C4 C5 120.0(6) . . ?
N1 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.5(6) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 121.0(7) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 118.4(6) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
N1 C8 C7 120.6(6) . . ?
N1 C8 C9 113.7(5) . . ?
C7 C8 C9 125.6(5) . . ?
N2 C9 C10 123.2(5) . . ?
N2 C9 C8 116.6(5) . . ?
C10 C9 C8 120.2(5) . . ?
C9 C10 C11 120.1(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 115.9(5) . . ?
C12 C11 C19 120.9(6) . . ?
C10 C11 C19 123.2(6) . . ?
C11 C12 C13 122.2(6) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
N2 C13 C12 122.2(6) . . ?
N2 C13 C14 119.3(6) . . ?
C12 C13 C14 118.3(5) . . ?
N3 C14 C15 123.2(6) . . ?
N3 C14 C13 115.8(6) . . ?
C15 C14 C13 120.8(6) . . ?
C14 C15 C16 119.1(7) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 117.8(7) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C16 C17 C18 118.5(7) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
N3 C18 C17 124.4(7) . . ?
N3 C18 H18 117.8 . . ?
C17 C18 H18 117.8 . . ?
C20 C19 C24 116.2(6) . . ?
C20 C19 C11 122.9(6) . . ?
C24 C19 C11 120.9(6) . . ?
C19 C20 C21 122.5(6) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C20 C21 C22 121.2(7) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
N4 C22 C23 120.8(6) . . ?
N4 C22 C21 123.3(7) . . ?
C23 C22 C21 115.9(6) . . ?
C24 C23 C22 121.3(6) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C19 122.8(7) . . ?
C23 C24 H24 118.6 . . ?
C19 C24 H24 118.6 . . ?
N4 C25 H25A 109.5 . . ?
N4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N4 C26 H26A 109.5 . . ?
N4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C8 N1 C4 120.4(6) . . ?
C8 N1 Re1 117.2(4) . . ?
C4 N1 Re1 122.3(4) . . ?
C13 N2 C9 116.0(5) . . ?
C13 N2 Re1 128.1(4) . . ?
C9 N2 Re1 113.1(4) . . ?
C18 N3 C14 117.0(6) . . ?
C22 N4 C25 121.1(6) . . ?
C22 N4 C26 118.5(6) . . ?
C25 N4 C26 120.1(5) . . ?
C3 Re1 C2 88.6(3) . . ?
C3 Re1 C1 88.5(3) . . ?
C2 Re1 C1 87.9(3) . . ?
C3 Re1 N1 94.1(3) . . ?
C2 Re1 N1 96.1(3) . . ?
C1 Re1 N1 175.2(2) . . ?
C3 Re1 N2 98.1(2) . . ?
C2 Re1 N2 168.4(2) . . ?
C1 Re1 N2 101.7(2) . . ?
N1 Re1 N2 74.03(19) . . ?
C3 Re1 Cl1 177.8(2) . . ?
C2 Re1 Cl1 91.8(2) . . ?
C1 Re1 Cl1 93.6(2) . . ?
N1 Re1 Cl1 83.71(14) . . ?
N2 Re1 Cl1 81.12(13) . . ?

_refine_diff_density_max         1.055
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.169

_shelxl_version_number           2014/6

