# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1409716'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Cl N4 O3 Re'
_chemical_formula_weight         592.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7219(5)
_cell_length_b                   7.6479(6)
_cell_length_c                   20.8140(15)
_cell_angle_alpha                89.990(3)
_cell_angle_beta                 87.244(4)
_cell_angle_gamma                66.833(4)
_cell_volume                     982.39(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.56

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    6.353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1860
_exptl_absorpt_correction_T_max  0.3588
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 Estimated minimum and maximum transmission:  0.4600  0.7456 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14818
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.65
_reflns_number_total             4435
_reflns_number_gt                4042
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.Hydrogen atoms were assigned 
 ideal positions and refined isotropically as riding atoms.  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0506P)²+9.8541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4435
_refine_ls_number_parameters     286
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_restrained_S_all      0.874
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1313(9) 0.1315(9) 0.9377(3) 0.0219(12) Uani 1 1 d . . .
H1 H 1.1149 0.2497 0.9542 0.026 Uiso 1 1 calc R . .
C2 C 1.2555(9) -0.0298(9) 0.9699(3) 0.0242(12) Uani 1 1 d . . .
H2 H 1.3207 -0.0201 1.0074 0.029 Uiso 1 1 calc R . .
C3 C 1.2811(9) -0.2062(9) 0.9453(3) 0.0258(13) Uani 1 1 d . . .
H3 H 1.3622 -0.3167 0.9665 0.031 Uiso 1 1 calc R . .
C4 C 1.1850(10) -0.2160(9) 0.8892(3) 0.0262(13) Uani 1 1 d . . .
H4 H 1.2021 -0.3331 0.8716 0.031 Uiso 1 1 calc R . .
C5 C 1.0630(9) -0.0492(8) 0.8596(3) 0.0224(12) Uani 1 1 d . . .
C6 C 0.9518(10) -0.0440(9) 0.8010(3) 0.0266(13) Uani 1 1 d . . .
H6 H 0.9610 -0.1560 0.7811 0.032 Uiso 1 1 calc R . .
C7 C 0.7114(9) 0.1278(8) 0.7236(3) 0.0218(12) Uani 1 1 d . . .
C8 C 0.5602(10) 0.0465(8) 0.7279(3) 0.0244(12) Uani 1 1 d . . .
H8 H 0.5489 -0.0198 0.7644 0.029 Uiso 1 1 calc R . .
C9 C 0.4266(10) 0.0640(9) 0.6781(3) 0.0266(13) Uani 1 1 d . . .
H9 H 0.3238 0.0108 0.6810 0.032 Uiso 1 1 calc R . .
C10 C 0.4458(10) 0.1618(8) 0.6232(3) 0.0231(12) Uani 1 1 d . . .
C11 C 0.5978(10) 0.2423(9) 0.6191(3) 0.0277(13) Uani 1 1 d . . .
H11 H 0.6115 0.3063 0.5822 0.033 Uiso 1 1 calc R . .
C12 C 0.7287(10) 0.2278(9) 0.6695(3) 0.0261(13) Uani 1 1 d . . .
H12 H 0.8282 0.2847 0.6672 0.031 Uiso 1 1 calc R . .
C13 C 0.1790(9) 0.2631(8) 0.4766(3) 0.0228(12) Uani 1 1 d . . .
C14 C -0.0030(11) 0.2207(10) 0.4871(3) 0.0313(14) Uani 1 1 d . . .
H14 H -0.0286 0.1745 0.5266 0.038 Uiso 1 1 calc R . .
C15 C -0.1464(12) 0.2473(11) 0.4386(3) 0.0355(15) Uani 1 1 d . . .
H15 H -0.2691 0.2206 0.4457 0.043 Uiso 1 1 calc R . .
C16 C -0.1054(11) 0.3141(9) 0.3795(3) 0.0304(14) Uani 1 1 d . . .
H16 H -0.1998 0.3306 0.3466 0.036 Uiso 1 1 calc R . .
C17 C 0.0754(11) 0.3560(10) 0.3694(3) 0.0326(14) Uani 1 1 d . . .
H17 H 0.1012 0.4020 0.3299 0.039 Uiso 1 1 calc R . .
C18 C 0.2183(11) 0.3303(10) 0.4174(3) 0.0312(14) Uani 1 1 d . . .
H18 H 0.3404 0.3579 0.4102 0.037 Uiso 1 1 calc R . .
C19 C 0.6012(9) 0.5551(9) 0.7832(3) 0.0219(12) Uani 1 1 d . A .
C20 C 0.7936(10) 0.5590(9) 0.8950(3) 0.0250(12) Uani 1 1 d . A .
C21 C 1.0435(15) 0.4143(18) 0.7886(6) 0.0180(4) Uani 0.75 1 d PD A 1
C22 C 0.588(4) 0.346(5) 0.8904(14) 0.057(3) Uani 0.25 1 d PD A 2
Cl1 Cl 0.5307(3) 0.2931(4) 0.89291(11) 0.0180(4) Uani 0.75 1 d P A 1
Cl2 Cl 1.1140(12) 0.4121(14) 0.7745(4) 0.057(3) Uani 0.25 1 d PD A 2
N1 N 1.0342(7) 0.1245(7) 0.8840(2) 0.0190(9) Uani 1 1 d . A .
N2 N 0.8399(7) 0.1193(7) 0.7771(2) 0.0192(9) Uani 1 1 d . A .
N3 N 0.2963(9) 0.1751(7) 0.5755(2) 0.0255(11) Uani 1 1 d . . .
N4 N 0.3357(8) 0.2438(7) 0.5232(2) 0.0253(11) Uani 1 1 d . . .
O1 O 0.4769(7) 0.6655(6) 0.7520(2) 0.0286(10) Uani 1 1 d . . .
O2 O 0.7898(7) 0.6709(7) 0.9333(2) 0.0336(11) Uani 1 1 d . . .
O3 O 1.1690(12) 0.4666(10) 0.7634(4) 0.0298(18) Uani 0.75 1 d PD A 1
O4 O 0.446(3) 0.314(4) 0.9129(11) 0.041(7) Uani 0.25 1 d PD A 2
Re1 Re 0.80967(4) 0.36721(3) 0.833893(10) 0.01951(8) Uani 1 1 d 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 N1 1.334(7) . ?
C1 C2 1.382(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9300 . ?
C5 N1 1.359(8) . ?
C5 C6 1.453(8) . ?
C6 N2 1.292(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(9) . ?
C7 C12 1.388(8) . ?
C7 N2 1.427(7) . ?
C8 C9 1.377(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(9) . ?
C10 N3 1.422(7) . ?
C11 C12 1.378(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.387(9) . ?
C13 C14 1.391(9) . ?
C13 N4 1.431(7) . ?
C14 C15 1.388(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.153(7) . ?
C19 Re1 1.924(6) . ?
C20 O2 1.162(8) . ?
C20 Re1 1.908(6) . ?
C21 O3 1.170(5) . ?
C21 Re1 1.947(4) . ?
C22 O4 1.150(5) . ?
C22 Re1 1.913(5) . ?
Cl1 Re1 2.442(2) . ?
Cl2 Re1 2.478(5) . ?
N1 Re1 2.181(4) . ?
N2 Re1 2.170(5) . ?
N3 N4 1.270(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.7(6) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 118.9(6) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.2(5) . . ?
N1 C5 C6 114.6(5) . . ?
C4 C5 C6 123.1(6) . . ?
N2 C6 C5 118.7(5) . . ?
N2 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C12 120.4(5) . . ?
C8 C7 N2 119.6(5) . . ?
C12 C7 N2 119.9(5) . . ?
C9 C8 C7 119.9(6) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.8(6) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 N3 124.9(5) . . ?
C9 C10 N3 115.0(6) . . ?
C12 C11 C10 120.1(6) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 119.7(6) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C18 C13 C14 120.0(5) . . ?
C18 C13 N4 115.1(6) . . ?
C14 C13 N4 124.9(6) . . ?
C15 C14 C13 120.1(6) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.5(7) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.0(6) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.7(6) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C13 119.7(6) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
O1 C19 Re1 178.9(5) . . ?
O2 C20 Re1 177.6(5) . . ?
O3 C21 Re1 171.4(11) . . ?
O4 C22 Re1 165(3) . . ?
C1 N1 C5 118.2(5) . . ?
C1 N1 Re1 126.3(4) . . ?
C5 N1 Re1 115.4(4) . . ?
C6 N2 C7 119.3(5) . . ?
C6 N2 Re1 116.1(4) . . ?
C7 N2 Re1 123.4(4) . . ?
N4 N3 C10 113.2(5) . . ?
N3 N4 C13 112.5(5) . . ?
C20 Re1 C22 82.6(11) . . ?
C20 Re1 C19 90.5(2) . . ?
C22 Re1 C19 92.2(11) . . ?
C20 Re1 C21 87.6(4) . . ?
C22 Re1 C21 170.0(11) . . ?
C19 Re1 C21 90.3(4) . . ?
C20 Re1 N2 171.0(2) . . ?
C22 Re1 N2 92.7(11) . . ?
C19 Re1 N2 97.3(2) . . ?
C21 Re1 N2 96.7(4) . . ?
C20 Re1 N1 97.2(2) . . ?
C22 Re1 N1 86.2(11) . . ?
C19 Re1 N1 171.8(2) . . ?
C21 Re1 N1 92.7(4) . . ?
N2 Re1 N1 74.75(17) . . ?
C20 Re1 Cl1 93.0(2) . . ?
C22 Re1 Cl1 10.4(11) . . ?
C19 Re1 Cl1 92.66(18) . . ?
C21 Re1 Cl1 177.0(4) . . ?
N2 Re1 Cl1 82.26(14) . . ?
N1 Re1 Cl1 84.27(14) . . ?
C20 Re1 Cl2 89.9(3) . . ?
C22 Re1 Cl2 171.7(11) . . ?
C19 Re1 Cl2 91.5(3) . . ?
C21 Re1 Cl2 2.6(5) . . ?
N2 Re1 Cl2 94.3(3) . . ?
N1 Re1 Cl2 91.2(3) . . ?
Cl1 Re1 Cl2 174.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.3(9) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
C2 C3 C4 C5 -1.0(9) . . . . ?
C3 C4 C5 N1 -0.1(9) . . . . ?
C3 C4 C5 C6 -178.8(6) . . . . ?
N1 C5 C6 N2 0.7(9) . . . . ?
C4 C5 C6 N2 179.5(6) . . . . ?
C12 C7 C8 C9 0.3(9) . . . . ?
N2 C7 C8 C9 176.1(5) . . . . ?
C7 C8 C9 C10 0.7(9) . . . . ?
C8 C9 C10 C11 -0.5(9) . . . . ?
C8 C9 C10 N3 -178.5(5) . . . . ?
C9 C10 C11 C12 -0.7(9) . . . . ?
N3 C10 C11 C12 177.1(6) . . . . ?
C10 C11 C12 C7 1.7(10) . . . . ?
C8 C7 C12 C11 -1.5(9) . . . . ?
N2 C7 C12 C11 -177.3(5) . . . . ?
C18 C13 C14 C15 -0.6(10) . . . . ?
N4 C13 C14 C15 179.1(6) . . . . ?
C13 C14 C15 C16 0.8(11) . . . . ?
C14 C15 C16 C17 -0.9(11) . . . . ?
C15 C16 C17 C18 0.7(10) . . . . ?
C16 C17 C18 C13 -0.5(10) . . . . ?
C14 C13 C18 C17 0.5(10) . . . . ?
N4 C13 C18 C17 -179.3(6) . . . . ?
C2 C1 N1 C5 -1.3(9) . . . . ?
C2 C1 N1 Re1 173.7(4) . . . . ?
C4 C5 N1 C1 1.2(9) . . . . ?
C6 C5 N1 C1 -179.9(5) . . . . ?
C4 C5 N1 Re1 -174.3(5) . . . . ?
C6 C5 N1 Re1 4.5(7) . . . . ?
C5 C6 N2 C7 -173.4(5) . . . . ?
C5 C6 N2 Re1 -5.6(8) . . . . ?
C8 C7 N2 C6 54.8(8) . . . . ?
C12 C7 N2 C6 -129.4(6) . . . . ?
C8 C7 N2 Re1 -112.0(5) . . . . ?
C12 C7 N2 Re1 63.8(7) . . . . ?
C11 C10 N3 N4 10.3(8) . . . . ?
C9 C10 N3 N4 -171.7(5) . . . . ?
C10 N3 N4 C13 -177.7(5) . . . . ?
C18 C13 N4 N3 -177.5(6) . . . . ?
C14 C13 N4 N3 2.7(9) . . . . ?
O4 C22 Re1 C20 161(13) . . . . ?
O4 C22 Re1 C19 71(12) . . . . ?
O4 C22 Re1 C21 175(8) . . . . ?
O4 C22 Re1 N2 -27(12) . . . . ?
O4 C22 Re1 N1 -101(12) . . . . ?
O4 C22 Re1 Cl1 -22(8) . . . . ?
C6 N2 Re1 C22 -79.4(11) . . . . ?
C7 N2 Re1 C22 87.8(11) . . . . ?
C6 N2 Re1 C19 -172.0(5) . . . . ?
C7 N2 Re1 C19 -4.7(5) . . . . ?
C6 N2 Re1 C21 96.9(6) . . . . ?
C7 N2 Re1 C21 -95.9(6) . . . . ?
C6 N2 Re1 N1 5.9(4) . . . . ?
C7 N2 Re1 N1 173.1(5) . . . . ?
C6 N2 Re1 Cl1 -80.2(4) . . . . ?
C7 N2 Re1 Cl1 87.0(4) . . . . ?
C6 N2 Re1 Cl2 96.0(5) . . . . ?
C7 N2 Re1 Cl2 -96.8(5) . . . . ?
C1 N1 Re1 C20 -4.7(5) . . . . ?
C5 N1 Re1 C20 170.4(4) . . . . ?
C1 N1 Re1 C22 -86.8(12) . . . . ?
C5 N1 Re1 C22 88.3(12) . . . . ?
C1 N1 Re1 C21 83.2(6) . . . . ?
C5 N1 Re1 C21 -101.7(6) . . . . ?
C1 N1 Re1 N2 179.4(5) . . . . ?
C5 N1 Re1 N2 -5.5(4) . . . . ?
C1 N1 Re1 Cl1 -97.1(5) . . . . ?
C5 N1 Re1 Cl1 78.0(4) . . . . ?
C1 N1 Re1 Cl2 85.3(5) . . . . ?
C5 N1 Re1 Cl2 -99.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         2.806
_refine_diff_density_min         -2.421
_refine_diff_density_rms         0.184
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1409717'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Br N4 O3 Re'
_chemical_formula_weight         636.47

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7633(7)
_cell_length_b                   7.6885(8)
_cell_length_c                   20.877(2)
_cell_angle_alpha                90.827(5)
_cell_angle_beta                 92.695(5)
_cell_angle_gamma                112.441(4)
_cell_volume                     1001.64(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8831
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.11

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.110
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    8.092
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.2256
_exptl_absorpt_correction_T_max  0.6172
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 Estimated minimum and maximum transmission:  0.4851  0.7452 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12167
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.11
_reflns_number_total             3521
_reflns_number_gt                3369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. All hydrogen atoms were  assigned ideal positions and refined isotropically as riding atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+7.7916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3521
_refine_ls_number_parameters     280
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_restrained_S_all      1.302
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.51856(17) 0.70589(13) 0.60588(4) 0.0196(2) Uani 0.80 1 d P A 1
Br2 Br 1.1123(6) 0.5970(6) 0.72351(19) 0.0196(2) Uani 0.20 1 d PD A 2
C1 C 1.1221(11) 0.8603(9) 0.5633(3) 0.0195(14) Uani 1 1 d . . .
H1 H 1.1005 0.7402 0.5450 0.023 Uiso 1 1 calc R . .
C2 C 1.2459(10) 1.0183(10) 0.5323(3) 0.0204(15) Uani 1 1 d . . .
H2 H 1.3089 1.0070 0.4936 0.025 Uiso 1 1 calc R . .
C3 C 1.2775(11) 1.1941(10) 0.5584(3) 0.0234(15) Uani 1 1 d . . .
H3 H 1.3614 1.3051 0.5376 0.028 Uiso 1 1 calc R . .
C4 C 1.1852(11) 1.2056(10) 0.6150(3) 0.0235(15) Uani 1 1 d . . .
H4 H 1.2050 1.3247 0.6338 0.028 Uiso 1 1 calc R . .
C5 C 1.0637(11) 1.0418(9) 0.6438(3) 0.0190(14) Uani 1 1 d . . .
C6 C 0.9555(11) 1.0381(9) 0.7026(3) 0.0206(15) Uani 1 1 d . . .
H6 H 0.9680 1.1522 0.7238 0.025 Uiso 1 1 calc R . .
C7 C 0.7155(11) 0.8725(9) 0.7787(3) 0.0206(15) Uani 1 1 d . . .
C8 C 0.5686(12) 0.9574(10) 0.7740(3) 0.0258(16) Uani 1 1 d . . .
H8 H 0.5598 1.0261 0.7372 0.031 Uiso 1 1 calc R . .
C9 C 0.4334(12) 0.9408(10) 0.8240(3) 0.0260(16) Uani 1 1 d . . .
H9 H 0.3311 0.9978 0.8212 0.031 Uiso 1 1 calc R . .
C10 C 0.4482(12) 0.8410(10) 0.8779(3) 0.0238(15) Uani 1 1 d . . .
C11 C 0.5990(12) 0.7577(10) 0.8816(3) 0.0265(16) Uani 1 1 d . . .
H11 H 0.6114 0.6910 0.9185 0.032 Uiso 1 1 calc R . .
C12 C 0.7292(12) 0.7724(10) 0.8318(3) 0.0264(16) Uani 1 1 d . . .
H12 H 0.8294 0.7131 0.8339 0.032 Uiso 1 1 calc R . .
C13 C 0.1773(11) 0.7377(9) 1.0229(3) 0.0226(15) Uani 1 1 d . . .
C14 C -0.0041(12) 0.7786(11) 1.0119(4) 0.0308(17) Uani 1 1 d . . .
H14 H -0.0300 0.8242 0.9716 0.037 Uiso 1 1 calc R . .
C15 C -0.1473(13) 0.7529(12) 1.0595(4) 0.0356(19) Uani 1 1 d . . .
H15 H -0.2710 0.7816 1.0521 0.043 Uiso 1 1 calc R . .
C16 C -0.1091(12) 0.6850(11) 1.1181(4) 0.0304(17) Uani 1 1 d . . .
H16 H -0.2070 0.6666 1.1509 0.036 Uiso 1 1 calc R . .
C17 C 0.0718(13) 0.6440(11) 1.1285(3) 0.0314(18) Uani 1 1 d . . .
H17 H 0.0973 0.5975 1.1687 0.038 Uiso 1 1 calc R . .
C18 C 0.2159(13) 0.6701(11) 1.0812(4) 0.0310(17) Uani 1 1 d . . .
H18 H 0.3400 0.6419 1.0887 0.037 Uiso 1 1 calc R . .
C20 C 0.7971(11) 0.4397(10) 0.6064(3) 0.0239(16) Uani 1 1 d . A .
C21 C 0.6092(12) 0.4479(10) 0.7182(3) 0.0212(15) Uani 1 1 d . A .
C22 C 1.0370(15) 0.5820(14) 0.7130(4) 0.0196(2) Uani 0.80 1 d PD A 1
C23 C 0.577(4) 0.652(5) 0.6140(15) 0.0196(2) Uani 0.20 1 d PD A 2
N1 N 1.0308(9) 0.8686(8) 0.6181(3) 0.0183(12) Uani 1 1 d . A .
N2 N 0.8436(9) 0.8798(8) 0.7252(3) 0.0199(12) Uani 1 1 d . A .
N3 N 0.2980(10) 0.8283(8) 0.9251(3) 0.0264(14) Uani 1 1 d . . .
N4 N 0.3340(10) 0.7587(8) 0.9764(3) 0.0256(13) Uani 1 1 d . . .
O1 O 0.7921(8) 0.3266(7) 0.5682(2) 0.0322(12) Uani 1 1 d . . .
O2 O 0.4863(8) 0.3393(7) 0.7493(2) 0.0261(11) Uani 1 1 d . . .
O3 O 1.1689(10) 0.5390(8) 0.7390(3) 0.0210(13) Uani 0.80 1 d PD A 1
O4 O 0.422(4) 0.654(4) 0.5824(14) 0.030(7) Uani 0.20 1 d PD A 2
Re1 Re 0.81276(5) 0.63128(4) 0.668022(13) 0.01889(9) Uani 1 1 d 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
Br1 Re1 2.5732(11) . ?
Br2 Re1 2.390(4) . ?
C1 N1 1.337(8) . ?
C1 C2 1.375(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(10) . ?
C4 H4 0.9500 . ?
C5 N1 1.361(8) . ?
C5 C6 1.454(9) . ?
C6 N2 1.275(9) . ?
C6 H6 0.9500 . ?
C7 C12 1.379(10) . ?
C7 C8 1.382(9) . ?
C7 N2 1.434(8) . ?
C8 C9 1.395(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(10) . ?
C10 N3 1.427(9) . ?
C11 C12 1.372(10) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.383(10) . ?
C13 C14 1.388(10) . ?
C13 N4 1.437(9) . ?
C14 C15 1.383(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(10) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C20 O1 1.161(8) . ?
C20 Re1 1.910(7) . ?
C21 O2 1.160(8) . ?
C21 Re1 1.918(8) . ?
C22 O3 1.177(9) . ?
C22 Re1 1.908(8) . ?
C23 O4 1.219(18) . ?
C23 Re1 1.968(17) . ?
N1 Re1 2.176(6) . ?
N2 Re1 2.173(5) . ?
N3 N4 1.258(8) . ?

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
N1 C1 C2 122.8(6) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 119.2(6) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 118.9(7) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 119.0(6) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 122.2(6) . . ?
N1 C5 C6 114.3(6) . . ?
C4 C5 C6 123.4(6) . . ?
N2 C6 C5 119.1(6) . . ?
N2 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C12 C7 C8 120.9(6) . . ?
C12 C7 N2 120.5(6) . . ?
C8 C7 N2 118.5(6) . . ?
C9 C8 C7 119.1(6) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.1(6) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 119.6(6) . . ?
C9 C10 N3 115.4(6) . . ?
C11 C10 N3 125.0(6) . . ?
C12 C11 C10 119.9(6) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C7 C12 C11 120.4(6) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C18 C13 C14 120.5(7) . . ?
C18 C13 N4 115.5(6) . . ?
C14 C13 N4 124.0(6) . . ?
C15 C14 C13 120.1(7) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.6(7) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 119.9(7) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.8(7) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 119.2(7) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
O1 C20 Re1 178.2(7) . . ?
O2 C21 Re1 178.9(6) . . ?
O3 C22 Re1 175.3(9) . . ?
O4 C23 Re1 176(3) . . ?
C1 N1 C5 117.8(6) . . ?
C1 N1 Re1 126.5(4) . . ?
C5 N1 Re1 115.5(4) . . ?
C6 N2 C7 119.9(6) . . ?
C6 N2 Re1 116.3(4) . . ?
C7 N2 Re1 122.8(4) . . ?
N4 N3 C10 113.3(6) . . ?
N3 N4 C13 113.4(6) . . ?
C20 Re1 C21 90.6(3) . . ?
C20 Re1 C22 87.9(4) . . ?
C21 Re1 C22 89.1(4) . . ?
C20 Re1 C23 84.3(11) . . ?
C21 Re1 C23 90.0(11) . . ?
C22 Re1 C23 172.1(12) . . ?
C20 Re1 N2 170.7(3) . . ?
C21 Re1 N2 97.6(2) . . ?
C22 Re1 N2 96.6(3) . . ?
C23 Re1 N2 91.3(11) . . ?
C20 Re1 N1 97.0(3) . . ?
C21 Re1 N1 171.9(2) . . ?
C22 Re1 N1 94.1(3) . . ?
C23 Re1 N1 87.8(11) . . ?
N2 Re1 N1 74.6(2) . . ?
C20 Re1 Br2 90.5(2) . . ?
C21 Re1 Br2 93.1(2) . . ?
C22 Re1 Br2 4.8(4) . . ?
C23 Re1 Br2 174.0(11) . . ?
N2 Re1 Br2 93.40(17) . . ?
N1 Re1 Br2 89.77(17) . . ?
C20 Re1 Br1 92.4(2) . . ?
C21 Re1 Br1 92.54(19) . . ?
C22 Re1 Br1 178.3(3) . . ?
C23 Re1 Br1 8.5(11) . . ?
N2 Re1 Br1 82.92(14) . . ?
N1 Re1 Br1 84.23(14) . . ?
Br2 Re1 Br1 173.62(10) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         2.002
_refine_diff_density_min         -1.572
_refine_diff_density_rms         0.141
