# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_phenphen
_database_code_depnum_ccdc_archive 'CCDC 1029144'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 F6 N6 O3 P Re'
_chemical_formula_weight         755.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1607(13)
_cell_length_b                   14.9974(17)
_cell_length_c                   14.0496(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.0710(10)
_cell_angle_gamma                90.00
_cell_volume                     2562.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7318
_cell_measurement_theta_min      2.156
_cell_measurement_theta_max      25.225

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    4.887
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5085
_exptl_absorpt_correction_T_max  0.6154
_exptl_absorpt_process_details   
;
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption corrections SADABS).
 R(int) = 0.1299 (selected reflections only, before parameter refinement)
 R(int) = 0.0491 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26732
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5037
_reflns_number_gt                4189
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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. The following restraints
 were applied (given as SHELXL lines):  
 SIMU 0.01 $C
 SIMU 0.01 $N
 SIMU 0.01 $O
 SIMU 0.01 $F
;

_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)+(0.0208P)²+0.5872P] 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         5037
_refine_ls_number_parameters     362
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0539
_refine_ls_wR_factor_gt          0.0493
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.255802(19) 0.144222(10) 0.704772(13) 0.03883(6) Uani 1 1 d . . .
C1 C 0.1479(5) 0.0720(5) 0.7674(5) 0.0581(18) Uani 1 1 d . . .
C2 C 0.3674(4) 0.0906(4) 0.7820(5) 0.0465(14) Uani 1 1 d . . .
C3 C 0.2357(5) 0.2320(3) 0.8021(4) 0.0484(11) Uani 1 1 d . . .
O1 O 0.0845(4) 0.0287(3) 0.8069(4) 0.0885(16) Uani 1 1 d . . .
O2 O 0.4339(4) 0.0604(3) 0.8300(3) 0.0761(15) Uani 1 1 d . . .
O3 O 0.2240(3) 0.2819(2) 0.8648(3) 0.0642(12) Uani 1 1 d . . .
N1 N 0.1301(4) 0.1969(3) 0.6070(4) 0.0429(11) Uani 1 1 d U . .
N2 N 0.0602(4) 0.1362(3) 0.5649(4) 0.0589(13) Uani 1 1 d U . .
N3 N -0.0048(4) 0.1778(4) 0.5071(4) 0.0620(13) Uani 1 1 d U . .
N4 N 0.0197(4) 0.2646(3) 0.5125(3) 0.0518(12) Uani 1 1 d U . .
C4 C -0.0439(5) 0.3300(5) 0.4577(5) 0.077(2) Uani 1 1 d . . .
H4A H -0.0926 0.2994 0.4149 0.116 Uiso 1 1 calc R . .
H4B H 0.0053 0.3671 0.4219 0.116 Uiso 1 1 calc R . .
H4C H -0.0862 0.3663 0.5005 0.116 Uiso 1 1 calc R . .
C5 C 0.1032(4) 0.2755(4) 0.5734(4) 0.0458(13) Uani 1 1 d U . .
C51 C 0.1530(4) 0.3631(3) 0.5961(4) 0.0459(12) Uani 1 1 d U . .
C52 C 0.2178(5) 0.4067(4) 0.5307(4) 0.0657(16) Uani 1 1 d U . .
H52 H 0.2298 0.3808 0.4715 0.079 Uiso 1 1 calc R . .
C53 C 0.2651(7) 0.4875(4) 0.5507(5) 0.0806(18) Uani 1 1 d U . .
H53 H 0.3077 0.5167 0.5054 0.097 Uiso 1 1 calc R . .
C54 C 0.2484(7) 0.5244(4) 0.6388(4) 0.0745(15) Uani 1 1 d U . .
H54 H 0.2816 0.5785 0.6538 0.089 Uiso 1 1 calc R . .
C55 C 0.1831(5) 0.4827(4) 0.7056(5) 0.0666(15) Uani 1 1 d U . .
H55 H 0.1719 0.5087 0.7649 0.080 Uiso 1 1 calc R . .
C56 C 0.1343(5) 0.4017(4) 0.6836(4) 0.0573(14) Uani 1 1 d U . .
H56 H 0.0892 0.3736 0.7277 0.069 Uiso 1 1 calc R . .
N11 N 0.3739(3) 0.2144(3) 0.6165(4) 0.0413(11) Uani 1 1 d . . .
N21 N 0.2835(3) 0.0544(3) 0.5860(3) 0.0401(10) Uani 1 1 d . . .
C12 C 0.4032(4) 0.1702(4) 0.5355(4) 0.0409(12) Uani 1 1 d U . .
C13 C 0.4784(4) 0.2058(4) 0.4698(4) 0.0516(14) Uani 1 1 d U . .
C14 C 0.5231(5) 0.2898(4) 0.4915(5) 0.0613(16) Uani 1 1 d U . .
H14 H 0.5732 0.3157 0.4499 0.074 Uiso 1 1 calc R . .
C15 C 0.4941(5) 0.3336(4) 0.5724(5) 0.0640(16) Uani 1 1 d U . .
H15 H 0.5248 0.3888 0.5868 0.077 Uiso 1 1 calc R . .
C16 C 0.4184(5) 0.2950(4) 0.6329(4) 0.0554(14) Uani 1 1 d U . .
H16 H 0.3974 0.3260 0.6872 0.066 Uiso 1 1 calc R . .
C17 C 0.5046(5) 0.1550(4) 0.3869(4) 0.0631(15) Uani 1 1 d U . .
H17 H 0.5546 0.1776 0.3430 0.076 Uiso 1 1 calc R . .
C22 C 0.3557(4) 0.0860(3) 0.5193(3) 0.0378(11) Uani 1 1 d U . .
C23 C 0.3825(4) 0.0372(4) 0.4368(4) 0.0486(12) Uani 1 1 d U . .
C24 C 0.3330(5) -0.0460(4) 0.4254(4) 0.0550(14) Uani 1 1 d U . .
H24 H 0.3495 -0.0808 0.3725 0.066 Uiso 1 1 calc R . .
C25 C 0.2604(6) -0.0764(3) 0.4919(3) 0.0543(12) Uani 1 1 d U . .
H25 H 0.2262 -0.1314 0.4839 0.065 Uiso 1 1 calc R . .
C26 C 0.2379(5) -0.0248(3) 0.5716(3) 0.0498(12) Uani 1 1 d U . .
H26 H 0.1890 -0.0467 0.6168 0.060 Uiso 1 1 calc R . .
C27 C 0.4581(5) 0.0752(4) 0.3713(4) 0.0598(14) Uani 1 1 d U . .
H27 H 0.4758 0.0439 0.3163 0.072 Uiso 1 1 calc R . .
F1 F 0.2301(5) 0.7282(3) 0.1698(3) 0.1107(19) Uani 1 1 d . . .
F2 F 0.1614(3) 0.8109(3) 0.2875(4) 0.1007(14) Uani 1 1 d . . .
F3 F 0.3405(3) 0.7743(3) 0.2829(4) 0.0998(15) Uani 1 1 d . . .
F4 F 0.2340(5) 0.7177(3) 0.3944(2) 0.1116(16) Uani 1 1 d . . .
F5 F 0.2941(3) 0.6298(2) 0.2768(3) 0.0801(11) Uani 1 1 d . . .
F6 F 0.1184(3) 0.6689(3) 0.2814(6) 0.156(3) Uani 1 1 d . . .
P1 P 0.22681(15) 0.72014(9) 0.28259(11) 0.0579(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 C2 1.913(6) . ?
Re1 C3 1.915(5) . ?
Re1 C1 1.916(7) . ?
Re1 N11 2.170(4) . ?
Re1 N21 2.171(4) . ?
Re1 N1 2.200(5) . ?
C1 O1 1.151(7) . ?
C2 O2 1.146(7) . ?
C3 O3 1.163(5) . ?
N1 C5 1.310(7) . ?
N1 N2 1.379(6) . ?
N2 N3 1.293(7) . ?
N3 N4 1.337(6) . ?
N4 C5 1.338(6) . ?
N4 C4 1.467(7) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C51 1.481(7) . ?
C51 C52 1.377(7) . ?
C51 C56 1.378(7) . ?
C52 C53 1.370(8) . ?
C52 H52 0.9300 . ?
C53 C54 1.371(8) . ?
C53 H53 0.9300 . ?
C54 C55 1.381(9) . ?
C54 H54 0.9300 . ?
C55 C56 1.386(8) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
N11 C16 1.345(6) . ?
N11 C12 1.365(6) . ?
N21 C26 1.326(6) . ?
N21 C22 1.369(5) . ?
C12 C13 1.405(7) . ?
C12 C22 1.407(7) . ?
C13 C14 1.405(8) . ?
C13 C17 1.429(8) . ?
C14 C15 1.360(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C27 1.342(8) . ?
C17 H17 0.9300 . ?
C22 C23 1.409(7) . ?
C23 C24 1.394(7) . ?
C23 C27 1.420(8) . ?
C24 C25 1.365(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
F1 P1 1.589(4) . ?
F2 P1 1.578(4) . ?
F3 P1 1.604(4) . ?
F4 P1 1.574(4) . ?
F5 P1 1.585(3) . ?
F6 P1 1.526(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Re1 C3 88.6(2) . . ?
C2 Re1 C1 89.3(2) . . ?
C3 Re1 C1 88.4(2) . . ?
C2 Re1 N11 93.3(2) . . ?
C3 Re1 N11 99.21(19) . . ?
C1 Re1 N11 172.0(2) . . ?
C2 Re1 N21 93.7(2) . . ?
C3 Re1 N21 174.78(17) . . ?
C1 Re1 N21 96.3(2) . . ?
N11 Re1 N21 76.00(16) . . ?
C2 Re1 N1 175.1(2) . . ?
C3 Re1 N1 96.3(2) . . ?
C1 Re1 N1 90.8(2) . . ?
N11 Re1 N1 85.90(13) . . ?
N21 Re1 N1 81.44(16) . . ?
O1 C1 Re1 178.5(6) . . ?
O2 C2 Re1 178.1(6) . . ?
O3 C3 Re1 176.4(4) . . ?
C5 N1 N2 106.6(5) . . ?
C5 N1 Re1 136.1(4) . . ?
N2 N1 Re1 117.3(3) . . ?
N3 N2 N1 109.1(5) . . ?
N2 N3 N4 107.3(5) . . ?
N3 N4 C5 108.9(5) . . ?
N3 N4 C4 120.3(5) . . ?
C5 N4 C4 130.8(5) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 N4 108.1(5) . . ?
N1 C5 C51 128.2(5) . . ?
N4 C5 C51 123.8(5) . . ?
C52 C51 C56 119.3(5) . . ?
C52 C51 C5 120.8(5) . . ?
C56 C51 C5 119.8(5) . . ?
C53 C52 C51 121.7(6) . . ?
C53 C52 H52 119.2 . . ?
C51 C52 H52 119.2 . . ?
C52 C53 C54 118.6(7) . . ?
C52 C53 H53 120.7 . . ?
C54 C53 H53 120.7 . . ?
C53 C54 C55 121.1(6) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 H54 119.4 . . ?
C54 C55 C56 119.4(6) . . ?
C54 C55 H55 120.3 . . ?
C56 C55 H55 120.3 . . ?
C51 C56 C55 119.8(6) . . ?
C51 C56 H56 120.1 . . ?
C55 C56 H56 120.1 . . ?
C16 N11 C12 118.3(5) . . ?
C16 N11 Re1 127.2(4) . . ?
C12 N11 Re1 114.5(3) . . ?
C26 N21 C22 118.3(4) . . ?
C26 N21 Re1 127.4(3) . . ?
C22 N21 Re1 114.3(3) . . ?
N11 C12 C13 122.2(5) . . ?
N11 C12 C22 117.6(4) . . ?
C13 C12 C22 120.2(5) . . ?
C14 C13 C12 116.8(6) . . ?
C14 C13 C17 124.6(6) . . ?
C12 C13 C17 118.6(6) . . ?
C15 C14 C13 120.9(6) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.0(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 122.7(6) . . ?
N11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C27 C17 C13 120.9(6) . . ?
C27 C17 H17 119.5 . . ?
C13 C17 H17 119.5 . . ?
N21 C22 C12 117.6(4) . . ?
N21 C22 C23 122.2(5) . . ?
C12 C22 C23 120.3(5) . . ?
C24 C23 C22 117.4(5) . . ?
C24 C23 C27 124.3(5) . . ?
C22 C23 C27 118.3(5) . . ?
C25 C24 C23 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 119.6(5) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
N21 C26 C25 122.6(5) . . ?
N21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C17 C27 C23 121.7(6) . . ?
C17 C27 H27 119.1 . . ?
C23 C27 H27 119.1 . . ?
F6 P1 F4 92.7(4) . . ?
F6 P1 F2 90.0(3) . . ?
F4 P1 F2 90.2(3) . . ?
F6 P1 F5 90.9(2) . . ?
F4 P1 F5 90.2(2) . . ?
F2 P1 F5 179.1(3) . . ?
F6 P1 F1 92.8(4) . . ?
F4 P1 F1 174.5(3) . . ?
F2 P1 F1 89.5(3) . . ?
F5 P1 F1 90.0(2) . . ?
F6 P1 F3 179.5(4) . . ?
F4 P1 F3 87.8(3) . . ?
F2 P1 F3 89.9(2) . . ?
F5 P1 F3 89.3(2) . . ?
F1 P1 F3 86.7(3) . . ?

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
C2 Re1 C1 O1 32(22) . . . . ?
C3 Re1 C1 O1 -56(22) . . . . ?
N11 Re1 C1 O1 142(21) . . . . ?
N21 Re1 C1 O1 126(22) . . . . ?
N1 Re1 C1 O1 -153(22) . . . . ?
C3 Re1 C2 O2 -4(17) . . . . ?
C1 Re1 C2 O2 -92(17) . . . . ?
N11 Re1 C2 O2 95(17) . . . . ?
N21 Re1 C2 O2 172(17) . . . . ?
N1 Re1 C2 O2 176(100) . . . . ?
C2 Re1 C3 O3 -40(8) . . . . ?
C1 Re1 C3 O3 49(8) . . . . ?
N11 Re1 C3 O3 -133(8) . . . . ?
N21 Re1 C3 O3 -157(7) . . . . ?
N1 Re1 C3 O3 140(8) . . . . ?
C2 Re1 N1 C5 -133(2) . . . . ?
C3 Re1 N1 C5 46.8(6) . . . . ?
C1 Re1 N1 C5 135.3(6) . . . . ?
N11 Re1 N1 C5 -52.0(5) . . . . ?
N21 Re1 N1 C5 -128.5(6) . . . . ?
C2 Re1 N1 N2 44(3) . . . . ?
C3 Re1 N1 N2 -135.6(4) . . . . ?
C1 Re1 N1 N2 -47.1(4) . . . . ?
N11 Re1 N1 N2 125.6(4) . . . . ?
N21 Re1 N1 N2 49.1(4) . . . . ?
C5 N1 N2 N3 0.9(6) . . . . ?
Re1 N1 N2 N3 -177.3(4) . . . . ?
N1 N2 N3 N4 -1.4(7) . . . . ?
N2 N3 N4 C5 1.4(7) . . . . ?
N2 N3 N4 C4 -177.3(5) . . . . ?
N2 N1 C5 N4 0.0(6) . . . . ?
Re1 N1 C5 N4 177.7(4) . . . . ?
N2 N1 C5 C51 179.8(5) . . . . ?
Re1 N1 C5 C51 -2.4(9) . . . . ?
N3 N4 C5 N1 -0.8(6) . . . . ?
C4 N4 C5 N1 177.7(6) . . . . ?
N3 N4 C5 C51 179.3(5) . . . . ?
C4 N4 C5 C51 -2.2(9) . . . . ?
N1 C5 C51 C52 108.0(7) . . . . ?
N4 C5 C51 C52 -72.2(7) . . . . ?
N1 C5 C51 C56 -72.1(8) . . . . ?
N4 C5 C51 C56 107.7(6) . . . . ?
C56 C51 C52 C53 0.5(9) . . . . ?
C5 C51 C52 C53 -179.5(6) . . . . ?
C51 C52 C53 C54 1.1(11) . . . . ?
C52 C53 C54 C55 -1.7(12) . . . . ?
C53 C54 C55 C56 0.6(11) . . . . ?
C52 C51 C56 C55 -1.6(8) . . . . ?
C5 C51 C56 C55 178.4(5) . . . . ?
C54 C55 C56 C51 1.1(9) . . . . ?
C2 Re1 N11 C16 -87.1(5) . . . . ?
C3 Re1 N11 C16 2.0(5) . . . . ?
C1 Re1 N11 C16 163.7(15) . . . . ?
N21 Re1 N11 C16 179.9(5) . . . . ?
N1 Re1 N11 C16 97.7(4) . . . . ?
C2 Re1 N11 C12 93.7(4) . . . . ?
C3 Re1 N11 C12 -177.2(4) . . . . ?
C1 Re1 N11 C12 -15.5(17) . . . . ?
N21 Re1 N11 C12 0.7(3) . . . . ?
N1 Re1 N11 C12 -81.5(4) . . . . ?
C2 Re1 N21 C26 87.5(5) . . . . ?
C3 Re1 N21 C26 -156(2) . . . . ?
C1 Re1 N21 C26 -2.2(5) . . . . ?
N11 Re1 N21 C26 -179.9(5) . . . . ?
N1 Re1 N21 C26 -92.1(4) . . . . ?
C2 Re1 N21 C22 -93.2(3) . . . . ?
C3 Re1 N21 C22 23(2) . . . . ?
C1 Re1 N21 C22 177.1(3) . . . . ?
N11 Re1 N21 C22 -0.7(3) . . . . ?
N1 Re1 N21 C22 87.2(3) . . . . ?
C16 N11 C12 C13 0.5(7) . . . . ?
Re1 N11 C12 C13 179.7(4) . . . . ?
C16 N11 C12 C22 -179.8(5) . . . . ?
Re1 N11 C12 C22 -0.6(6) . . . . ?
N11 C12 C13 C14 0.3(8) . . . . ?
C22 C12 C13 C14 -179.4(5) . . . . ?
N11 C12 C13 C17 179.9(5) . . . . ?
C22 C12 C13 C17 0.3(8) . . . . ?
C12 C13 C14 C15 0.0(9) . . . . ?
C17 C13 C14 C15 -179.7(6) . . . . ?
C13 C14 C15 C16 -0.9(9) . . . . ?
C12 N11 C16 C15 -1.5(8) . . . . ?
Re1 N11 C16 C15 179.3(4) . . . . ?
C14 C15 C16 N11 1.8(9) . . . . ?
C14 C13 C17 C27 -179.9(6) . . . . ?
C12 C13 C17 C27 0.5(8) . . . . ?
C26 N21 C22 C12 180.0(5) . . . . ?
Re1 N21 C22 C12 0.6(5) . . . . ?
C26 N21 C22 C23 0.1(7) . . . . ?
Re1 N21 C22 C23 -179.2(4) . . . . ?
N11 C12 C22 N21 0.0(7) . . . . ?
C13 C12 C22 N21 179.6(4) . . . . ?
N11 C12 C22 C23 179.8(4) . . . . ?
C13 C12 C22 C23 -0.5(7) . . . . ?
N21 C22 C23 C24 -0.5(7) . . . . ?
C12 C22 C23 C24 179.6(5) . . . . ?
N21 C22 C23 C27 179.9(5) . . . . ?
C12 C22 C23 C27 0.0(7) . . . . ?
C22 C23 C24 C25 1.1(8) . . . . ?
C27 C23 C24 C25 -179.3(5) . . . . ?
C23 C24 C25 C26 -1.2(8) . . . . ?
C22 N21 C26 C25 -0.2(8) . . . . ?
Re1 N21 C26 C25 179.0(4) . . . . ?
C24 C25 C26 N21 0.8(9) . . . . ?
C13 C17 C27 C23 -1.0(9) . . . . ?
C24 C23 C27 C17 -178.8(6) . . . . ?
C22 C23 C27 C17 0.7(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.083
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_bipyphen
_database_code_depnum_ccdc_archive 'CCDC 1029145'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 Cl2 F3 N6 O6 Re S'
_chemical_formula_weight         820.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2488(13)
_cell_length_b                   22.212(3)
_cell_length_c                   14.293(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.906(2)
_cell_angle_gamma                90.00
_cell_volume                     2934.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9291
_cell_measurement_theta_min      2.323
_cell_measurement_theta_max      26.4075

_exptl_crystal_description       needle
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1592
_exptl_absorpt_coefficient_mu    4.461
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4403
_exptl_absorpt_correction_T_max  0.6166
_exptl_absorpt_process_details   
;
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption corrections SADABS).
 R(int) = 0.1001 (selected reflections only, before parameter refinement)
 R(int) = 0.0595 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27349
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5156
_reflns_number_gt                4343
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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. 
;

_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)+(0.0433P)²+35.2742P] 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         5156
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.36413(3) 0.171020(13) 0.77368(2) 0.01392(11) Uani 1 1 d . . .
C1 C 0.5164(8) 0.1732(4) 0.8679(6) 0.0220(17) Uani 1 1 d . . .
C2 C 0.3675(8) 0.0843(3) 0.7798(6) 0.0208(16) Uani 1 1 d . . .
C3 C 0.5055(8) 0.1689(3) 0.6791(5) 0.0173(15) Uani 1 1 d . . .
O1 O 0.6041(6) 0.1734(3) 0.9283(4) 0.0335(15) Uani 1 1 d . . .
O2 O 0.3700(7) 0.0334(3) 0.7847(5) 0.0399(16) Uani 1 1 d . . .
O3 O 0.5875(6) 0.1663(3) 0.6201(4) 0.0294(13) Uani 1 1 d . . .
N1 N 0.3351(7) 0.3041(3) 0.8442(4) 0.0179(13) Uani 1 1 d . . .
N2 N 0.3473(6) 0.2685(3) 0.7684(4) 0.0158(13) Uani 1 1 d . . .
N3 N 0.3443(7) 0.2993(3) 0.6902(4) 0.0182(13) Uani 1 1 d . . .
N4 N 0.3305(7) 0.3570(3) 0.7172(4) 0.0174(13) Uani 1 1 d . . .
C4 C 0.3175(9) 0.4033(4) 0.6454(6) 0.0242(18) Uani 1 1 d . . .
H4A H 0.3270 0.3849 0.5835 0.036 Uiso 1 1 calc R . .
H4B H 0.3941 0.4333 0.6556 0.036 Uiso 1 1 calc R . .
H4C H 0.2229 0.4229 0.6486 0.036 Uiso 1 1 calc R . .
C5 C 0.3253(7) 0.3598(3) 0.8106(5) 0.0162(15) Uani 1 1 d . . .
C51 C 0.3073(8) 0.4141(3) 0.8669(5) 0.0186(16) Uani 1 1 d . . .
C52 C 0.3939(9) 0.4644(4) 0.8538(6) 0.0251(18) Uani 1 1 d . . .
H52 H 0.4643 0.4642 0.8068 0.030 Uiso 1 1 calc R . .
C53 C 0.3770(10) 0.5147(4) 0.9095(6) 0.031(2) Uani 1 1 d . . .
H53 H 0.4357 0.5493 0.9009 0.037 Uiso 1 1 calc R . .
C54 C 0.2746(11) 0.5147(4) 0.9776(7) 0.037(2) Uani 1 1 d . . .
H54 H 0.2620 0.5496 1.0148 0.044 Uiso 1 1 calc R . .
C55 C 0.1899(10) 0.4643(4) 0.9923(6) 0.034(2) Uani 1 1 d . . .
H55 H 0.1217 0.4642 1.0405 0.041 Uiso 1 1 calc R . .
C56 C 0.2055(10) 0.4139(4) 0.9360(6) 0.0288(19) Uani 1 1 d . . .
H56 H 0.1466 0.3794 0.9447 0.035 Uiso 1 1 calc R . .
N11 N 0.1773(6) 0.1772(3) 0.6797(4) 0.0123(12) Uani 1 1 d . . .
C12 C 0.0501(7) 0.1904(3) 0.7197(5) 0.0138(15) Uani 1 1 d . . .
C13 C -0.0766(8) 0.2001(3) 0.6640(5) 0.0182(16) Uani 1 1 d . . .
H13 H -0.1650 0.2100 0.6923 0.022 Uiso 1 1 calc R . .
C14 C -0.0712(8) 0.1952(4) 0.5693(5) 0.0204(16) Uani 1 1 d . . .
H14 H -0.1562 0.2007 0.5311 0.024 Uiso 1 1 calc R . .
C15 C 0.0597(9) 0.1819(3) 0.5287(5) 0.0209(17) Uani 1 1 d . . .
H15 H 0.0657 0.1789 0.4627 0.025 Uiso 1 1 calc R . .
C16 C 0.1806(8) 0.1732(3) 0.5862(5) 0.0174(15) Uani 1 1 d . . .
H16 H 0.2698 0.1639 0.5584 0.021 Uiso 1 1 calc R . .
N21 N 0.1833(6) 0.1816(3) 0.8651(4) 0.0167(13) Uani 1 1 d . . .
C22 C 0.0541(8) 0.1942(3) 0.8220(5) 0.0162(15) Uani 1 1 d . . .
C23 C -0.0656(8) 0.2094(3) 0.8741(6) 0.0189(16) Uani 1 1 d . . .
H23 H -0.1560 0.2180 0.8435 0.023 Uiso 1 1 calc R . .
C24 C -0.0514(8) 0.2118(3) 0.9700(6) 0.0205(16) Uani 1 1 d . . .
H24 H -0.1313 0.2235 1.0060 0.025 Uiso 1 1 calc R . .
C25 C 0.0792(9) 0.1971(4) 1.0143(5) 0.0222(17) Uani 1 1 d . . .
H25 H 0.0898 0.1968 1.0806 0.027 Uiso 1 1 calc R . .
C26 C 0.1937(8) 0.1829(3) 0.9587(5) 0.0175(16) Uani 1 1 d . . .
H26 H 0.2844 0.1737 0.9884 0.021 Uiso 1 1 calc R . .
C30 C 0.9145(8) 0.3667(4) 0.7256(6) 0.0264(19) Uani 1 1 d . . .
F1 F 0.9154(6) 0.3561(3) 0.6344(4) 0.0488(15) Uani 1 1 d . . .
F2 F 0.9628(5) 0.4218(2) 0.7404(4) 0.0371(13) Uani 1 1 d . . .
F3 F 1.0107(5) 0.3287(2) 0.7663(4) 0.0385(13) Uani 1 1 d . . .
S1 S 0.7341(2) 0.35588(9) 0.77196(15) 0.0246(4) Uani 1 1 d . . .
O4 O 0.7578(8) 0.3662(4) 0.8697(5) 0.055(2) Uani 1 1 d . . .
O5 O 0.6500(7) 0.4004(3) 0.7212(6) 0.053(2) Uani 1 1 d . . .
O6 O 0.6976(6) 0.2950(2) 0.7475(4) 0.0247(12) Uani 1 1 d . . .
C31 C 0.8088(18) 0.0353(7) 0.8621(12) 0.089(5) Uani 1 1 d . . .
H31A H 0.7438 0.0557 0.9057 0.107 Uiso 1 1 calc R . .
H31B H 0.7862 -0.0082 0.8622 0.107 Uiso 1 1 calc R . .
Cl3 Cl 0.7812(5) 0.0647(2) 0.7485(4) 0.1030(14) Uani 1 1 d . . .
Cl4 Cl 0.9800(8) 0.0461(2) 0.8969(4) 0.139(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 C3 1.913(8) . ?
Re1 C1 1.916(8) . ?
Re1 C2 1.929(8) . ?
Re1 N11 2.157(6) . ?
Re1 N21 2.169(6) . ?
Re1 N2 2.172(6) . ?
C1 O1 1.165(10) . ?
C2 O2 1.133(9) . ?
C3 O3 1.154(9) . ?
N1 C5 1.328(10) . ?
N1 N2 1.349(9) . ?
N2 N3 1.310(9) . ?
N3 N4 1.346(9) . ?
N4 C5 1.340(10) . ?
N4 C4 1.456(10) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C51 1.462(10) . ?
C51 C56 1.386(12) . ?
C51 C52 1.392(11) . ?
C52 C53 1.385(12) . ?
C52 H52 0.9500 . ?
C53 C54 1.380(14) . ?
C53 H53 0.9500 . ?
C54 C55 1.386(14) . ?
C54 H54 0.9500 . ?
C55 C56 1.388(12) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
N11 C16 1.342(9) . ?
N11 C12 1.356(9) . ?
C12 C13 1.412(10) . ?
C12 C22 1.464(11) . ?
C13 C14 1.360(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N21 C26 1.338(10) . ?
N21 C22 1.355(9) . ?
C22 C23 1.396(11) . ?
C23 C24 1.375(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(11) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C30 F2 1.317(10) . ?
C30 F1 1.324(10) . ?
C30 F3 1.344(10) . ?
C30 S1 1.831(8) . ?
S1 O4 1.425(7) . ?
S1 O6 1.435(6) . ?
S1 O5 1.439(7) . ?
C31 Cl4 1.661(18) . ?
C31 Cl3 1.761(16) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Re1 C1 89.6(3) . . ?
C3 Re1 C2 89.8(3) . . ?
C1 Re1 C2 89.0(3) . . ?
C3 Re1 N11 96.5(3) . . ?
C1 Re1 N11 172.1(3) . . ?
C2 Re1 N11 95.9(3) . . ?
C3 Re1 N21 170.9(3) . . ?
C1 Re1 N21 97.9(3) . . ?
C2 Re1 N21 95.3(3) . . ?
N11 Re1 N21 75.5(2) . . ?
C3 Re1 N2 92.9(3) . . ?
C1 Re1 N2 92.8(3) . . ?
C2 Re1 N2 176.7(3) . . ?
N11 Re1 N2 81.9(2) . . ?
N21 Re1 N2 81.8(2) . . ?
O1 C1 Re1 176.6(7) . . ?
O2 C2 Re1 179.1(8) . . ?
O3 C3 Re1 177.6(7) . . ?
C5 N1 N2 105.2(6) . . ?
N3 N2 N1 112.3(6) . . ?
N3 N2 Re1 123.3(5) . . ?
N1 N2 Re1 124.4(5) . . ?
N2 N3 N4 104.6(6) . . ?
C5 N4 N3 109.7(6) . . ?
C5 N4 C4 131.7(7) . . ?
N3 N4 C4 118.6(6) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 N4 108.2(6) . . ?
N1 C5 C51 125.2(7) . . ?
N4 C5 C51 126.6(7) . . ?
C56 C51 C52 120.4(7) . . ?
C56 C51 C5 118.9(7) . . ?
C52 C51 C5 120.7(7) . . ?
C53 C52 C51 119.6(8) . . ?
C53 C52 H52 120.2 . . ?
C51 C52 H52 120.2 . . ?
C54 C53 C52 119.9(9) . . ?
C54 C53 H53 120.1 . . ?
C52 C53 H53 120.1 . . ?
C53 C54 C55 120.8(8) . . ?
C53 C54 H54 119.6 . . ?
C55 C54 H54 119.6 . . ?
C54 C55 C56 119.5(9) . . ?
C54 C55 H55 120.2 . . ?
C56 C55 H55 120.2 . . ?
C51 C56 C55 119.8(8) . . ?
C51 C56 H56 120.1 . . ?
C55 C56 H56 120.1 . . ?
C16 N11 C12 118.9(6) . . ?
C16 N11 Re1 124.9(5) . . ?
C12 N11 Re1 116.1(5) . . ?
N11 C12 C13 120.7(7) . . ?
N11 C12 C22 116.1(6) . . ?
C13 C12 C22 123.2(7) . . ?
C14 C13 C12 119.4(7) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.6(7) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 118.8(7) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N11 C16 C15 122.6(7) . . ?
N11 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C26 N21 C22 118.9(7) . . ?
C26 N21 Re1 125.0(5) . . ?
C22 N21 Re1 115.8(5) . . ?
N21 C22 C23 120.7(7) . . ?
N21 C22 C12 115.8(6) . . ?
C23 C22 C12 123.5(7) . . ?
C24 C23 C22 119.4(7) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.0(7) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 117.7(7) . . ?
C26 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?
N21 C26 C25 123.3(7) . . ?
N21 C26 H26 118.4 . . ?
C25 C26 H26 118.4 . . ?
F2 C30 F1 108.1(7) . . ?
F2 C30 F3 107.3(7) . . ?
F1 C30 F3 106.8(7) . . ?
F2 C30 S1 111.8(6) . . ?
F1 C30 S1 111.6(6) . . ?
F3 C30 S1 111.0(6) . . ?
O4 S1 O6 114.7(4) . . ?
O4 S1 O5 116.5(5) . . ?
O6 S1 O5 113.9(4) . . ?
O4 S1 C30 102.8(4) . . ?
O6 S1 C30 104.2(4) . . ?
O5 S1 C30 102.2(4) . . ?
Cl4 C31 Cl3 109.3(9) . . ?
Cl4 C31 H31A 109.8 . . ?
Cl3 C31 H31A 109.8 . . ?
Cl4 C31 H31B 109.8 . . ?
Cl3 C31 H31B 109.8 . . ?
H31A C31 H31B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 Re1 C1 O1 -159(13) . . . . ?
C2 Re1 C1 O1 -69(13) . . . . ?
N11 Re1 C1 O1 60(14) . . . . ?
N21 Re1 C1 O1 26(13) . . . . ?
N2 Re1 C1 O1 108(13) . . . . ?
C3 Re1 C2 O2 123(45) . . . . ?
C1 Re1 C2 O2 33(45) . . . . ?
N11 Re1 C2 O2 -141(45) . . . . ?
N21 Re1 C2 O2 -65(45) . . . . ?
N2 Re1 C2 O2 -91(44) . . . . ?
C1 Re1 C3 O3 147(17) . . . . ?
C2 Re1 C3 O3 58(17) . . . . ?
N11 Re1 C3 O3 -38(17) . . . . ?
N21 Re1 C3 O3 -67(17) . . . . ?
N2 Re1 C3 O3 -120(17) . . . . ?
C5 N1 N2 N3 -0.6(8) . . . . ?
C5 N1 N2 Re1 -179.0(4) . . . . ?
C3 Re1 N2 N3 41.8(6) . . . . ?
C1 Re1 N2 N3 131.5(6) . . . . ?
C2 Re1 N2 N3 -104(5) . . . . ?
N11 Re1 N2 N3 -54.4(5) . . . . ?
N21 Re1 N2 N3 -130.9(6) . . . . ?
C3 Re1 N2 N1 -140.0(6) . . . . ?
C1 Re1 N2 N1 -50.2(6) . . . . ?
C2 Re1 N2 N1 74(5) . . . . ?
N11 Re1 N2 N1 123.8(5) . . . . ?
N21 Re1 N2 N1 47.3(5) . . . . ?
N1 N2 N3 N4 0.4(7) . . . . ?
Re1 N2 N3 N4 178.8(4) . . . . ?
N2 N3 N4 C5 -0.1(8) . . . . ?
N2 N3 N4 C4 -177.4(6) . . . . ?
N2 N1 C5 N4 0.5(8) . . . . ?
N2 N1 C5 C51 178.6(7) . . . . ?
N3 N4 C5 N1 -0.3(8) . . . . ?
C4 N4 C5 N1 176.6(7) . . . . ?
N3 N4 C5 C51 -178.4(7) . . . . ?
C4 N4 C5 C51 -1.5(13) . . . . ?
N1 C5 C51 C56 -45.9(11) . . . . ?
N4 C5 C51 C56 131.9(8) . . . . ?
N1 C5 C51 C52 132.0(8) . . . . ?
N4 C5 C51 C52 -50.2(11) . . . . ?
C56 C51 C52 C53 -0.7(12) . . . . ?
C5 C51 C52 C53 -178.5(7) . . . . ?
C51 C52 C53 C54 0.0(12) . . . . ?
C52 C53 C54 C55 1.2(13) . . . . ?
C53 C54 C55 C56 -1.9(13) . . . . ?
C52 C51 C56 C55 0.0(12) . . . . ?
C5 C51 C56 C55 177.9(7) . . . . ?
C54 C55 C56 C51 1.2(13) . . . . ?
C3 Re1 N11 C16 6.2(6) . . . . ?
C1 Re1 N11 C16 147.3(19) . . . . ?
C2 Re1 N11 C16 -84.3(6) . . . . ?
N21 Re1 N11 C16 -178.2(6) . . . . ?
N2 Re1 N11 C16 98.2(6) . . . . ?
C3 Re1 N11 C12 -169.0(5) . . . . ?
C1 Re1 N11 C12 -28(2) . . . . ?
C2 Re1 N11 C12 100.5(5) . . . . ?
N21 Re1 N11 C12 6.6(5) . . . . ?
N2 Re1 N11 C12 -77.0(5) . . . . ?
C16 N11 C12 C13 -0.4(10) . . . . ?
Re1 N11 C12 C13 175.1(5) . . . . ?
C16 N11 C12 C22 -179.9(6) . . . . ?
Re1 N11 C12 C22 -4.4(8) . . . . ?
N11 C12 C13 C14 1.1(11) . . . . ?
C22 C12 C13 C14 -179.4(7) . . . . ?
C12 C13 C14 C15 -1.4(11) . . . . ?
C13 C14 C15 C16 1.0(11) . . . . ?
C12 N11 C16 C15 0.0(11) . . . . ?
Re1 N11 C16 C15 -175.0(5) . . . . ?
C14 C15 C16 N11 -0.3(12) . . . . ?
C3 Re1 N21 C26 -151.2(16) . . . . ?
C1 Re1 N21 C26 -5.2(6) . . . . ?
C2 Re1 N21 C26 84.5(6) . . . . ?
N11 Re1 N21 C26 179.3(6) . . . . ?
N2 Re1 N21 C26 -96.9(6) . . . . ?
C3 Re1 N21 C22 21(2) . . . . ?
C1 Re1 N21 C22 167.5(5) . . . . ?
C2 Re1 N21 C22 -102.8(5) . . . . ?
N11 Re1 N21 C22 -8.0(5) . . . . ?
N2 Re1 N21 C22 75.7(5) . . . . ?
C26 N21 C22 C23 1.3(10) . . . . ?
Re1 N21 C22 C23 -171.9(5) . . . . ?
C26 N21 C22 C12 -178.5(6) . . . . ?
Re1 N21 C22 C12 8.3(8) . . . . ?
N11 C12 C22 N21 -2.6(9) . . . . ?
C13 C12 C22 N21 177.9(7) . . . . ?
N11 C12 C22 C23 177.6(7) . . . . ?
C13 C12 C22 C23 -1.9(11) . . . . ?
N21 C22 C23 C24 0.2(11) . . . . ?
C12 C22 C23 C24 179.9(7) . . . . ?
C22 C23 C24 C25 -2.2(11) . . . . ?
C23 C24 C25 C26 2.8(12) . . . . ?
C22 N21 C26 C25 -0.7(11) . . . . ?
Re1 N21 C26 C25 171.8(6) . . . . ?
C24 C25 C26 N21 -1.3(12) . . . . ?
F2 C30 S1 O4 -61.7(7) . . . . ?
F1 C30 S1 O4 177.2(7) . . . . ?
F3 C30 S1 O4 58.2(7) . . . . ?
F2 C30 S1 O6 178.4(6) . . . . ?
F1 C30 S1 O6 57.2(7) . . . . ?
F3 C30 S1 O6 -61.8(7) . . . . ?
F2 C30 S1 O5 59.5(7) . . . . ?
F1 C30 S1 O5 -61.7(7) . . . . ?
F3 C30 S1 O5 179.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.759
_refine_diff_density_min         -1.520
_refine_diff_density_rms         0.186
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_phenaldehyde
_database_code_depnum_ccdc_archive 'CCDC 1029146'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;


#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#


_audit_creation_date             2011-06-07T08:58:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C25 H16 Cl3 D F6 N6 O4 P Re'
_chemical_formula_moiety         'C24 H16 N6 O4 Re, F6 P, C D Cl3'
_chemical_formula_weight         903.98

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-c  2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.7999(12)
_cell_length_b                   11.1806(5)
_cell_length_c                   26.1866(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.901(5)
_cell_angle_gamma                90
_cell_volume                     5999.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4903
_cell_measurement_theta_min      3.622
_cell_measurement_theta_max      28.3365

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 3 0.0097
-1 0 -3 0.0209
1 0 0 0.0197
-1 0 0 0.0692
1 -2 -1 0.0971
-1 1 0 0.0725

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.454
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  0.884

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      -0.0139002148
_diffrn_orient_matrix_ub_12      0.0531851458
_diffrn_orient_matrix_ub_13      0.0076772378
_diffrn_orient_matrix_ub_21      -0.0170593242
_diffrn_orient_matrix_ub_22      -0.0333925621
_diffrn_orient_matrix_ub_23      0.0163843239
_diffrn_orient_matrix_ub_31      0.0265645496
_diffrn_orient_matrix_ub_32      0.0068203891
_diffrn_orient_matrix_ub_33      0.0207160642
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_av_unetI/netI     0.1614
_diffrn_reflns_number            17010
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.861
_reflns_number_total             6501
_reflns_number_gt                3812
_reflns_threshold_expression     I>2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.

The PF6- anion was modelled as being disordered over two sets of sites with
site occupancies constrained to 0.5. Displacement parameters were restrained 
to reasonable values.
;
_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)+(0.0313P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6501
_refine_ls_number_parameters     479
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.938
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0
_refine_diff_density_max         3.124
_refine_diff_density_min         -1.739
_refine_diff_density_rms         0.198

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Re1 Re 0.594795(16) 0.85080(3) 0.595378(13) 0.01739(10) Uani 1 1 d . . .
C1 C 0.5791(4) 0.6822(8) 0.6001(3) 0.024(2) Uani 1 1 d . . .
O1 O 0.5690(3) 0.5821(5) 0.6054(2) 0.0366(18) Uani 1 1 d . . .
C3 C 0.6596(4) 0.8160(7) 0.5523(4) 0.027(2) Uani 1 1 d U . .
O3 O 0.6952(3) 0.7964(6) 0.5248(3) 0.0442(18) Uani 1 1 d . . .
C2 C 0.5333(4) 0.8562(7) 0.5315(3) 0.0195(17) Uani 1 1 d U . .
O2 O 0.4983(3) 0.8578(5) 0.4925(2) 0.0283(13) Uani 1 1 d . . .
N11 N 0.6090(3) 1.0424(6) 0.5985(3) 0.0177(16) Uani 1 1 d . . .
C12 C 0.5682(4) 1.1058(7) 0.6245(3) 0.019(2) Uani 1 1 d . . .
C13 C 0.5695(4) 1.2313(7) 0.6292(3) 0.022(2) Uani 1 1 d . . .
C14 C 0.6135(5) 1.2941(8) 0.6045(4) 0.033(3) Uani 1 1 d . . .
H14 H 0.615 1.379 0.6055 0.04 Uiso 1 1 calc R . .
C15 C 0.6545(5) 1.2312(8) 0.5787(3) 0.031(2) Uani 1 1 d . . .
H15 H 0.6854 1.2728 0.5626 0.037 Uiso 1 1 calc R . .
C16 C 0.6515(4) 1.1058(7) 0.5759(3) 0.022(2) Uani 1 1 d . . .
H16 H 0.6803 1.0645 0.5575 0.027 Uiso 1 1 calc R . .
C17 C 0.5232(5) 1.2875(8) 0.6565(3) 0.030(2) Uani 1 1 d . . .
H17 H 0.5216 1.3723 0.6584 0.036 Uiso 1 1 calc R . .
N21 N 0.5253(3) 0.9135(5) 0.6422(2) 0.0171(15) Uani 1 1 d . . .
C22 C 0.5234(4) 1.0368(7) 0.6485(3) 0.0192(19) Uani 1 1 d . . .
C23 C 0.4799(4) 1.0939(8) 0.6764(3) 0.027(2) Uani 1 1 d . . .
C24 C 0.4374(4) 1.0194(8) 0.6992(3) 0.031(2) Uani 1 1 d . . .
H24 H 0.4072 1.0535 0.7184 0.037 Uiso 1 1 calc R . .
C25 C 0.4402(5) 0.8986(8) 0.6932(3) 0.033(2) Uani 1 1 d . . .
H25 H 0.4115 0.8484 0.7081 0.039 Uiso 1 1 calc R . .
C26 C 0.4852(4) 0.8478(9) 0.6654(3) 0.0264(19) Uani 1 1 d . . .
H26 H 0.4872 0.7632 0.663 0.032 Uiso 1 1 calc R . .
C27 C 0.4819(5) 1.2218(8) 0.6795(4) 0.032(2) Uani 1 1 d . . .
H27 H 0.4531 1.2616 0.6984 0.038 Uiso 1 1 calc R . .
N1 N 0.6647(3) 0.8497(6) 0.6682(2) 0.0176(14) Uani 1 1 d . . .
N2 N 0.6558(4) 0.9176(6) 0.7084(3) 0.0263(17) Uani 1 1 d . . .
N3 N 0.6995(4) 0.8926(6) 0.7483(3) 0.035(2) Uani 1 1 d . . .
N4 N 0.7382(4) 0.8055(6) 0.7326(3) 0.0326(19) Uani 1 1 d . . .
C4 C 0.7940(5) 0.7567(9) 0.7683(4) 0.049(3) Uani 1 1 d . . .
H4A H 0.8143 0.6928 0.751 0.074 Uiso 1 1 calc R . .
H4B H 0.7789 0.7243 0.799 0.074 Uiso 1 1 calc R . .
H4C H 0.8259 0.8203 0.7789 0.074 Uiso 1 1 calc R . .
C5 C 0.7171(4) 0.7821(7) 0.6835(3) 0.0193(19) Uani 1 1 d . . .
C51 C 0.7485(5) 0.6921(8) 0.6539(4) 0.031(2) Uani 1 1 d . . .
C52 C 0.7962(5) 0.7293(8) 0.6242(4) 0.038(3) Uani 1 1 d . . .
H52 H 0.8073 0.8115 0.623 0.046 Uiso 1 1 calc R . .
C53 C 0.8253(4) 0.6488(10) 0.5981(3) 0.044(2) Uani 1 1 d . . .
H53 H 0.8563 0.674 0.5776 0.053 Uiso 1 1 calc R . .
C54 C 0.8099(4) 0.5271(7) 0.6008(3) 0.028(2) Uani 1 1 d . . .
C55 C 0.7646(5) 0.4921(7) 0.6287(3) 0.027(2) Uani 1 1 d . . .
H55 H 0.7538 0.4096 0.6296 0.033 Uiso 1 1 calc R . .
C56 C 0.7337(5) 0.5722(7) 0.6561(4) 0.034(2) Uani 1 1 d . . .
H56 H 0.7025 0.5453 0.6761 0.041 Uiso 1 1 calc R . .
C57 C 0.8448(5) 0.4376(10) 0.5730(4) 0.043(3) Uani 1 1 d . . .
H57 H 0.8338 0.3557 0.5759 0.052 Uiso 1 1 calc R . .
O57 O 0.8845(4) 0.4610(6) 0.5481(3) 0.054(2) Uani 1 1 d . . .
P1 P 0.8811(4) 0.0594(8) 0.7139(4) 0.037(2) Uani 0.5 1 d P A 1
F11 F 0.8139(10) 0.054(2) 0.7364(8) 0.084(7) Uani 0.5 1 d PU A 1
F12 F 0.8502(9) 0.1581(19) 0.6706(8) 0.066(5) Uani 0.5 1 d PU A 1
F13 F 0.9454(9) 0.0758(17) 0.6962(9) 0.095(7) Uani 0.5 1 d PU A 1
F14 F 0.9075(12) 0.159(3) 0.7511(11) 0.084(8) Uani 0.5 1 d PU A 1
F15 F 0.8607(9) -0.0425(12) 0.6718(7) 0.074(4) Uani 0.5 1 d PU A 1
F16 F 0.9118(8) -0.0383(12) 0.7529(6) 0.075(5) Uani 0.5 1 d PU A 1
P2 P 0.8470(7) 0.0765(10) 0.6960(5) 0.074(3) Uani 0.5 1 d P B 2
F21 F 0.7872(13) 0.042(2) 0.7146(9) 0.111(9) Uani 0.5 1 d PU B 2
F22 F 0.8213(10) 0.1987(17) 0.6710(8) 0.071(6) Uani 0.5 1 d PU B 2
F23 F 0.9120(11) 0.0933(15) 0.6688(7) 0.081(6) Uani 0.5 1 d PU B 2
F24 F 0.8766(10) 0.146(3) 0.7487(11) 0.073(7) Uani 0.5 1 d PU B 2
F25 F 0.8108(10) 0.0112(15) 0.6462(8) 0.104(6) Uani 0.5 1 d PU B 2
F26 F 0.8762(11) -0.0528(16) 0.7183(10) 0.103(6) Uani 0.5 1 d PU B 2
C0 C 0.8864(5) 1.0195(8) 0.5527(4) 0.044(3) Uani 1 1 d . . .
D0 D 0.8829 1.0113 0.5902 0.052 Uiso 1 1 calc R . .
Cl1 Cl 0.80835(14) 0.9958(3) 0.51543(17) 0.0877(12) Uani 1 1 d . . .
Cl2 Cl 0.93957(14) 0.9069(2) 0.53735(10) 0.0475(7) Uani 1 1 d . . .
Cl3 Cl 0.91427(11) 1.1615(2) 0.54297(9) 0.0398(6) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 C1 1.921(9) . ?
Re1 C2 1.923(9) . ?
Re1 C3 1.939(9) . ?
Re1 N11 2.162(6) . ?
Re1 N21 2.166(6) . ?
Re1 N1 2.189(6) . ?
C1 O1 1.152(9) . ?
C3 O3 1.140(9) . ?
C2 O2 1.150(9) . ?
N11 C16 1.345(10) . ?
N11 C12 1.374(10) . ?
C12 C13 1.409(11) . ?
C12 C22 1.435(12) . ?
C13 C14 1.398(12) . ?
C13 C17 1.440(12) . ?
C14 C15 1.369(13) . ?
C14 H14 0.95 . ?
C15 C16 1.405(11) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 C27 1.349(13) . ?
C17 H17 0.95 . ?
N21 C26 1.335(10) . ?
N21 C22 1.390(10) . ?
C22 C23 1.411(11) . ?
C23 C24 1.419(12) . ?
C23 C27 1.432(11) . ?
C24 C25 1.362(12) . ?
C24 H24 0.95 . ?
C25 C26 1.400(12) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C27 H27 0.95 . ?
N1 C5 1.331(10) . ?
N1 N2 1.337(9) . ?
N2 N3 1.293(9) . ?
N3 N4 1.373(10) . ?
N4 C5 1.310(10) . ?
N4 C4 1.465(11) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C51 1.488(12) . ?
C51 C56 1.379(12) . ?
C51 C52 1.424(13) . ?
C52 C53 1.337(13) . ?
C52 H52 0.95 . ?
C53 C54 1.403(13) . ?
C53 H53 0.95 . ?
C54 C55 1.346(12) . ?
C54 C57 1.495(12) . ?
C55 C56 1.374(12) . ?
C55 H55 0.95 . ?
C56 H56 0.95 . ?
C57 O57 1.167(11) . ?
C57 H57 0.95 . ?
P1 F13 1.50(2) . ?
P1 F14 1.52(3) . ?
P1 F16 1.556(17) . ?
P1 F15 1.591(18) . ?
P1 F11 1.61(2) . ?
P1 F12 1.63(2) . ?
P2 F21 1.47(3) . ?
P2 F22 1.57(2) . ?
P2 F25 1.57(2) . ?
P2 F24 1.61(3) . ?
P2 F26 1.64(2) . ?
P2 F23 1.64(2) . ?
C0 Cl3 1.724(9) . ?
C0 Cl1 1.766(11) . ?
C0 Cl2 1.767(10) . ?
C0 D0 1 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Re1 C2 89.5(4) . . ?
C1 Re1 C3 89.0(3) . . ?
C2 Re1 C3 85.7(3) . . ?
C1 Re1 N11 173.6(3) . . ?
C2 Re1 N11 93.9(3) . . ?
C3 Re1 N11 96.7(3) . . ?
C1 Re1 N21 98.3(3) . . ?
C2 Re1 N21 94.2(3) . . ?
C3 Re1 N21 172.7(3) . . ?
N11 Re1 N21 76.0(2) . . ?
C1 Re1 N1 91.9(3) . . ?
C2 Re1 N1 178.5(3) . . ?
C3 Re1 N1 94.7(3) . . ?
N11 Re1 N1 84.7(2) . . ?
N21 Re1 N1 85.2(2) . . ?
O1 C1 Re1 176.5(8) . . ?
O3 C3 Re1 176.4(8) . . ?
O2 C2 Re1 177.6(7) . . ?
C16 N11 C12 117.0(7) . . ?
C16 N11 Re1 127.0(5) . . ?
C12 N11 Re1 115.9(5) . . ?
N11 C12 C13 123.6(8) . . ?
N11 C12 C22 116.3(7) . . ?
C13 C12 C22 120.1(8) . . ?
C14 C13 C12 117.7(8) . . ?
C14 C13 C17 123.9(8) . . ?
C12 C13 C17 118.3(9) . . ?
C15 C14 C13 118.8(8) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 120.8(9) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
N11 C16 C15 122.0(9) . . ?
N11 C16 H16 119 . . ?
C15 C16 H16 119 . . ?
C27 C17 C13 121.1(8) . . ?
C27 C17 H17 119.5 . . ?
C13 C17 H17 119.5 . . ?
C26 N21 C22 117.3(7) . . ?
C26 N21 Re1 127.6(6) . . ?
C22 N21 Re1 115.1(5) . . ?
N21 C22 C23 123.0(8) . . ?
N21 C22 C12 116.5(7) . . ?
C23 C22 C12 120.4(8) . . ?
C22 C23 C24 117.0(8) . . ?
C22 C23 C27 117.8(9) . . ?
C24 C23 C27 125.2(9) . . ?
C25 C24 C23 119.4(8) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.5(9) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
N21 C26 C25 122.7(9) . . ?
N21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C17 C27 C23 122.2(9) . . ?
C17 C27 H27 118.9 . . ?
C23 C27 H27 118.9 . . ?
C5 N1 N2 107.5(6) . . ?
C5 N1 Re1 130.8(5) . . ?
N2 N1 Re1 121.5(5) . . ?
N3 N2 N1 110.0(7) . . ?
N2 N3 N4 106.1(7) . . ?
C5 N4 N3 108.8(7) . . ?
C5 N4 C4 130.3(8) . . ?
N3 N4 C4 120.9(8) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N4 C5 N1 107.6(7) . . ?
N4 C5 C51 122.9(8) . . ?
N1 C5 C51 129.5(7) . . ?
C56 C51 C52 119.2(9) . . ?
C56 C51 C5 121.1(9) . . ?
C52 C51 C5 119.7(8) . . ?
C53 C52 C51 120.1(8) . . ?
C53 C52 H52 119.9 . . ?
C51 C52 H52 119.9 . . ?
C52 C53 C54 120.0(9) . . ?
C52 C53 H53 120 . . ?
C54 C53 H53 120 . . ?
C55 C54 C53 119.8(8) . . ?
C55 C54 C57 120.9(8) . . ?
C53 C54 C57 119.3(9) . . ?
C54 C55 C56 121.9(8) . . ?
C54 C55 H55 119.1 . . ?
C56 C55 H55 119.1 . . ?
C55 C56 C51 119.0(9) . . ?
C55 C56 H56 120.5 . . ?
C51 C56 H56 120.5 . . ?
O57 C57 C54 124.9(10) . . ?
O57 C57 H57 117.6 . . ?
C54 C57 H57 117.6 . . ?
F13 P1 F14 82.2(14) . . ?
F13 P1 F16 90.1(11) . . ?
F14 P1 F16 91.8(12) . . ?
F13 P1 F15 91.1(12) . . ?
F14 P1 F15 173.3(14) . . ?
F16 P1 F15 89.1(9) . . ?
F13 P1 F11 174.0(13) . . ?
F14 P1 F11 91.8(14) . . ?
F16 P1 F11 91.0(12) . . ?
F15 P1 F11 94.8(11) . . ?
F13 P1 F12 88.2(11) . . ?
F14 P1 F12 90.3(13) . . ?
F16 P1 F12 177.1(12) . . ?
F15 P1 F12 88.6(11) . . ?
F11 P1 F12 90.9(12) . . ?
F21 P2 F22 96.9(14) . . ?
F21 P2 F25 80.7(13) . . ?
F22 P2 F25 88.7(13) . . ?
F21 P2 F24 93.7(14) . . ?
F22 P2 F24 89.3(14) . . ?
F25 P2 F24 173.8(14) . . ?
F21 P2 F26 86.1(13) . . ?
F22 P2 F26 175.8(13) . . ?
F25 P2 F26 88.9(12) . . ?
F24 P2 F26 93.4(16) . . ?
F21 P2 F23 169.6(14) . . ?
F22 P2 F23 88.1(12) . . ?
F25 P2 F23 90.4(10) . . ?
F24 P2 F23 95.4(12) . . ?
F26 P2 F23 88.5(12) . . ?
Cl3 C0 Cl1 110.9(6) . . ?
Cl3 C0 Cl2 112.5(6) . . ?
Cl1 C0 Cl2 108.6(5) . . ?
Cl3 C0 D0 108.2 . . ?
Cl1 C0 D0 108.2 . . ?
Cl2 C0 D0 108.2 . . ?
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_bipyaldehyde
_database_code_depnum_ccdc_archive 'CCDC 1029147'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#


_audit_creation_date             2011-06-19T21:16:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C23 H17 Cl3 F6 N6 O4 P Re'
_chemical_formula_moiety         'C22 H16 N6 O4 Re, F6 P, C H Cl3'
_chemical_formula_weight         878.95

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-c 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.0576(9)
_cell_length_b                   16.6963(5)
_cell_length_c                   15.9749(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.077(4)
_cell_angle_gamma                90
_cell_volume                     6103.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9201
_cell_measurement_theta_min      2.8787
_cell_measurement_theta_max      40.7723

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_size_max          0.4321
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.0878
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.1717
0 -1 1 0.1823
0 -1 -1 0.1758
0 0 -1 0.0813
0 0 1 0.0978
-1 0 0 0.0597
1 0 0 0.0281

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.375
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
        (compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.277
_exptl_absorpt_correction_T_max  0.688

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0009
_diffrn_orient_matrix_ub_11      0.0301456
_diffrn_orient_matrix_ub_12      -0.0078182
_diffrn_orient_matrix_ub_13      -0.0009173
_diffrn_orient_matrix_ub_21      -0.0028002
_diffrn_orient_matrix_ub_22      -0.0364895
_diffrn_orient_matrix_ub_23      0.0218588
_diffrn_orient_matrix_ub_31      -0.0066085
_diffrn_orient_matrix_ub_32      -0.0202934
_diffrn_orient_matrix_ub_33      -0.039071
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_number            38648
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_full        30
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             8891
_reflns_number_gt                7164
_reflns_threshold_expression     I>2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.

The CHCl3 solvent molecule was modelled as being disordered over
two sets of sites with occupancies of the two components each constrained 
to 0.5 after trial refinement.
The PF6 anion was also disordered over two sets of sites but with occupancies 
refined to 0.889(12) and its complement.  Geometries of the minor 
component were restrained to ideal values.
;
_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)+(0.0134P)²+94.2298P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8891
_refine_ls_number_parameters     459
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.297
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.474
_refine_diff_density_min         -0.96
_refine_diff_density_rms         0.178

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.231 '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'

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
Re1 Re 0.805237(12) 0.545175(16) 0.701981(18) 0.02222(8) Uani 1 1 d . . .
C1 C 0.8063(3) 0.4623(5) 0.6172(5) 0.0317(17) Uani 1 1 d . . .
O1 O 0.8061(3) 0.4156(4) 0.5650(4) 0.0499(17) Uani 1 1 d . . .
C2 C 0.8889(4) 0.5399(5) 0.7236(6) 0.0384(19) Uani 1 1 d . . .
O2 O 0.9386(3) 0.5378(5) 0.7376(6) 0.068(2) Uani 1 1 d . . .
C3 C 0.8017(3) 0.4630(4) 0.7842(5) 0.0284(15) Uani 1 1 d . . .
O3 O 0.8005(3) 0.4135(3) 0.8347(4) 0.0439(16) Uani 1 1 d . . .
N11 N 0.7995(3) 0.6491(3) 0.7823(4) 0.0212(12) Uani 1 1 d . . .
C12 C 0.8019(3) 0.7219(4) 0.7446(4) 0.0219(13) Uani 1 1 d . . .
C13 C 0.8009(4) 0.7933(4) 0.7911(5) 0.0304(17) Uani 1 1 d . . .
H13 H 0.8019 0.8438 0.764 0.037 Uiso 1 1 calc R . .
C14 C 0.7983(5) 0.7889(5) 0.8763(6) 0.044(2) Uani 1 1 d . . .
H14 H 0.7983 0.8364 0.909 0.053 Uiso 1 1 calc R . .
C15 C 0.7957(5) 0.7138(5) 0.9149(6) 0.046(2) Uani 1 1 d . . .
H15 H 0.7939 0.7095 0.9738 0.056 Uiso 1 1 calc R . .
C16 C 0.7959(4) 0.6466(5) 0.8654(5) 0.0316(17) Uani 1 1 d . . .
H16 H 0.7932 0.5957 0.8914 0.038 Uiso 1 1 calc R . .
N21 N 0.8084(3) 0.6475(4) 0.6187(4) 0.0275(13) Uani 1 1 d . . .
C22 C 0.8078(3) 0.7218(4) 0.6548(5) 0.0259(15) Uani 1 1 d . . .
C23 C 0.8144(4) 0.7900(5) 0.6084(5) 0.037(2) Uani 1 1 d . . .
H23 H 0.8117 0.8414 0.6332 0.045 Uiso 1 1 calc R . .
C24 C 0.8249(6) 0.7831(6) 0.5251(6) 0.063(4) Uani 1 1 d . . .
H24 H 0.8323 0.8295 0.4937 0.075 Uiso 1 1 calc R . .
C25 C 0.8246(6) 0.7106(6) 0.4891(6) 0.058(3) Uani 1 1 d . . .
H25 H 0.83 0.7054 0.4314 0.07 Uiso 1 1 calc R . .
C26 C 0.8161(5) 0.6432(6) 0.5371(5) 0.045(2) Uani 1 1 d . . .
H26 H 0.8159 0.5921 0.511 0.054 Uiso 1 1 calc R . .
N1 N 0.6821(3) 0.6257(3) 0.6680(4) 0.0214(12) Uani 1 1 d . . .
N2 N 0.7109(3) 0.5557(3) 0.6799(4) 0.0201(11) Uani 1 1 d . . .
N3 N 0.6753(3) 0.4948(3) 0.6794(4) 0.0222(12) Uani 1 1 d . . .
N4 N 0.6218(3) 0.5264(3) 0.6664(4) 0.0210(11) Uani 1 1 d . . .
C4 C 0.5704(3) 0.4745(4) 0.6679(5) 0.0288(16) Uani 1 1 d . . .
H4A H 0.5624 0.4463 0.6139 0.043 Uiso 1 1 calc R . .
H4B H 0.5365 0.5072 0.6772 0.043 Uiso 1 1 calc R . .
H4C H 0.5781 0.4354 0.7136 0.043 Uiso 1 1 calc R . .
C5 C 0.6261(3) 0.6064(4) 0.6586(5) 0.0233(14) Uani 1 1 d . . .
C51 C 0.5785(4) 0.6638(5) 0.6432(6) 0.0347(18) Uani 1 1 d . . .
C52 C 0.5285(4) 0.6465(6) 0.5862(7) 0.047(2) Uani 1 1 d . . .
H52 H 0.5254 0.5968 0.557 0.056 Uiso 1 1 calc R . .
C53 C 0.4839(4) 0.7027(6) 0.5731(8) 0.055(3) Uani 1 1 d . . .
H53 H 0.4496 0.691 0.5357 0.066 Uiso 1 1 calc R . .
C54 C 0.4892(5) 0.7742(7) 0.6136(9) 0.066(4) Uani 1 1 d . . .
C55 C 0.5391(5) 0.7942(6) 0.6668(9) 0.066(3) Uani 1 1 d . . .
H55 H 0.5425 0.8453 0.6932 0.079 Uiso 1 1 calc R . .
C56 C 0.5844(4) 0.7384(5) 0.6814(7) 0.046(2) Uani 1 1 d . . .
H56 H 0.619 0.7515 0.7173 0.055 Uiso 1 1 calc R . .
C57 C 0.4380(6) 0.8300(8) 0.6015(11) 0.083(5) Uani 1 1 d . . .
H57 H 0.4058 0.8155 0.5614 0.099 Uiso 1 1 calc R . .
O57 O 0.4350(5) 0.8889(6) 0.6372(9) 0.122(5) Uani 1 1 d . . .
P1 P 0.63381(11) 0.52671(13) 0.91796(14) 0.0365(5) Uani 1 1 d D . .
F11 F 0.6713(4) 0.4780(5) 0.9915(4) 0.063(2) Uani 0.889(12) 1 d P A 1
F12 F 0.5806(5) 0.5306(8) 0.9724(6) 0.112(5) Uani 0.889(12) 1 d P A 1
F13 F 0.5941(3) 0.5727(4) 0.8443(4) 0.055(2) Uani 0.889(12) 1 d P A 1
F14 F 0.6860(4) 0.5223(8) 0.8633(5) 0.102(4) Uani 0.889(12) 1 d P A 1
F15 F 0.6105(4) 0.4449(4) 0.8771(8) 0.109(5) Uani 0.889(12) 1 d P A 1
F16 F 0.6577(6) 0.6098(5) 0.9556(7) 0.115(5) Uani 0.889(12) 1 d P A 1
F21 F 0.5699(10) 0.536(3) 0.870(3) 0.11(3) Uiso 0.111(12) 1 d PD A 2
F22 F 0.658(2) 0.5987(18) 0.866(3) 0.09(2) Uiso 0.111(12) 1 d PD A 2
F23 F 0.6968(11) 0.514(3) 0.970(3) 0.10(3) Uiso 0.111(12) 1 d PD A 2
F24 F 0.606(2) 0.4572(19) 0.968(3) 0.09(3) Uiso 0.111(12) 1 d PD A 2
F25 F 0.6503(17) 0.4714(18) 0.8533(17) 0.047(14) Uiso 0.111(12) 1 d PD A 2
F26 F 0.6217(16) 0.5850(17) 0.9825(16) 0.038(12) Uiso 0.111(12) 1 d PD A 2
C10 C 0.4964(11) 0.0327(12) 0.9488(14) 0.054(5) Uani 0.5 1 d P B -1
H10 H 0.5131 0.0034 0.9027 0.065 Uiso 0.5 1 calc PR B -1
Cl1 Cl 0.4948(6) 0.1360(4) 0.9233(5) 0.125(4) Uani 0.5 1 d P B -1
Cl2 Cl 0.5434(6) 0.0247(10) 1.0352(9) 0.141(7) Uani 0.5 1 d P B -1
Cl3 Cl 0.4285(4) -0.0041(7) 0.9548(6) 0.087(3) Uani 0.5 1 d P B -1
C20 C 0.4914(12) 0.2235(15) 0.793(2) 0.086(10) Uani 0.5 1 d P C -2
H20 H 0.5001 0.1709 0.767 0.103 Uiso 0.5 1 calc PR C -2
Cl4 Cl 0.4375(3) 0.2103(6) 0.8544(6) 0.099(3) Uani 0.5 1 d P C -2
Cl5 Cl 0.5530(5) 0.2629(8) 0.8366(10) 0.127(5) Uani 0.5 1 d P C -2
Cl6 Cl 0.4613(5) 0.2871(7) 0.7130(11) 0.139(6) Uani 0.5 1 d P C -2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.908(8) . ?
Re1 C2 1.918(9) . ?
Re1 C1 1.939(8) . ?
Re1 N2 2.167(6) . ?
Re1 N11 2.172(6) . ?
Re1 N21 2.172(6) . ?
C1 O1 1.140(9) . ?
C2 O2 1.142(11) . ?
C3 O3 1.157(9) . ?
N11 C16 1.342(9) . ?
N11 C12 1.360(8) . ?
C12 C13 1.406(10) . ?
C12 C22 1.458(10) . ?
C13 C14 1.372(12) . ?
C13 H13 0.95 . ?
C14 C15 1.401(12) . ?
C14 H14 0.95 . ?
C15 C16 1.373(11) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
N21 C26 1.339(10) . ?
N21 C22 1.369(10) . ?
C22 C23 1.378(10) . ?
C23 C24 1.386(13) . ?
C23 H23 0.95 . ?
C24 C25 1.339(14) . ?
C24 H24 0.95 . ?
C25 C26 1.389(13) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
N1 C5 1.320(9) . ?
N1 N2 1.347(7) . ?
N2 N3 1.305(8) . ?
N3 N4 1.335(8) . ?
N4 C5 1.347(8) . ?
N4 C4 1.470(9) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C51 1.456(10) . ?
C51 C56 1.386(13) . ?
C51 C52 1.407(13) . ?
C52 C53 1.389(13) . ?
C52 H52 0.95 . ?
C53 C54 1.358(17) . ?
C53 H53 0.95 . ?
C54 C55 1.384(17) . ?
C54 C57 1.498(15) . ?
C55 C56 1.398(14) . ?
C55 H55 0.95 . ?
C56 H56 0.95 . ?
C57 O57 1.142(16) . ?
C57 H57 0.95 . ?
P1 F26 1.469(9) . ?
P1 F25 1.470(9) . ?
P1 F14 1.573(8) . ?
P1 F15 1.580(8) . ?
P1 F21 1.581(10) . ?
P1 F16 1.583(9) . ?
P1 F24 1.587(10) . ?
P1 F12 1.589(8) . ?
P1 F11 1.594(7) . ?
P1 F13 1.596(7) . ?
P1 F22 1.597(10) . ?
P1 F23 1.597(10) . ?
C10 Cl2 1.65(2) . ?
C10 Cl3 1.70(3) . ?
C10 Cl1 1.77(2) . ?
C10 H10 1 . ?
C20 Cl5 1.64(3) . ?
C20 Cl4 1.69(3) . ?
C20 Cl6 1.73(4) . ?
C20 H20 1 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Re1 C2 88.3(4) . . ?
C3 Re1 C1 88.5(3) . . ?
C2 Re1 C1 89.6(3) . . ?
C3 Re1 N2 92.5(3) . . ?
C2 Re1 N2 177.8(3) . . ?
C1 Re1 N2 92.5(3) . . ?
C3 Re1 N11 99.0(3) . . ?
C2 Re1 N11 93.6(3) . . ?
C1 Re1 N11 171.9(3) . . ?
N2 Re1 N11 84.2(2) . . ?
C3 Re1 N21 174.1(3) . . ?
C2 Re1 N21 92.2(3) . . ?
C1 Re1 N21 97.4(3) . . ?
N2 Re1 N21 86.9(2) . . ?
N11 Re1 N21 75.1(2) . . ?
O1 C1 Re1 177.3(8) . . ?
O2 C2 Re1 178.8(8) . . ?
O3 C3 Re1 178.9(7) . . ?
C16 N11 C12 118.5(6) . . ?
C16 N11 Re1 125.1(5) . . ?
C12 N11 Re1 116.4(4) . . ?
N11 C12 C13 121.3(6) . . ?
N11 C12 C22 116.6(6) . . ?
C13 C12 C22 122.1(6) . . ?
C14 C13 C12 119.0(7) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 119.6(7) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 118.4(8) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
N11 C16 C15 123.3(7) . . ?
N11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
C26 N21 C22 117.9(7) . . ?
C26 N21 Re1 125.0(6) . . ?
C22 N21 Re1 116.8(5) . . ?
N21 C22 C23 121.0(7) . . ?
N21 C22 C12 115.0(6) . . ?
C23 C22 C12 123.9(7) . . ?
C22 C23 C24 119.4(8) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 119.7(8) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.2(9) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
N21 C26 C25 122.6(9) . . ?
N21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C5 N1 N2 105.3(5) . . ?
N3 N2 N1 112.1(6) . . ?
N3 N2 Re1 123.7(4) . . ?
N1 N2 Re1 124.1(4) . . ?
N2 N3 N4 105.2(5) . . ?
N3 N4 C5 109.1(6) . . ?
N3 N4 C4 119.8(6) . . ?
C5 N4 C4 130.9(6) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 N4 108.3(6) . . ?
N1 C5 C51 124.5(6) . . ?
N4 C5 C51 127.3(7) . . ?
C56 C51 C52 119.8(8) . . ?
C56 C51 C5 119.0(8) . . ?
C52 C51 C5 121.0(8) . . ?
C53 C52 C51 119.4(10) . . ?
C53 C52 H52 120.3 . . ?
C51 C52 H52 120.3 . . ?
C54 C53 C52 120.0(10) . . ?
C54 C53 H53 120 . . ?
C52 C53 H53 120 . . ?
C53 C54 C55 121.7(9) . . ?
C53 C54 C57 117.5(11) . . ?
C55 C54 C57 120.8(12) . . ?
C54 C55 C56 119.3(10) . . ?
C54 C55 H55 120.4 . . ?
C56 C55 H55 120.4 . . ?
C51 C56 C55 119.7(10) . . ?
C51 C56 H56 120.2 . . ?
C55 C56 H56 120.2 . . ?
O57 C57 C54 124.4(14) . . ?
O57 C57 H57 117.8 . . ?
C54 C57 H57 117.8 . . ?
F26 P1 F25 175.6(12) . . ?
F26 P1 F21 91.6(11) . . ?
F25 P1 F21 91.6(11) . . ?
F14 P1 F15 88.5(7) . . ?
F14 P1 F16 89.9(7) . . ?
F15 P1 F16 177.9(7) . . ?
F26 P1 F24 90.4(10) . . ?
F25 P1 F24 92.8(9) . . ?
F21 P1 F24 85(2) . . ?
F14 P1 F12 179.3(7) . . ?
F15 P1 F12 90.9(7) . . ?
F16 P1 F12 90.7(7) . . ?
F14 P1 F11 90.1(4) . . ?
F15 P1 F11 89.4(4) . . ?
F16 P1 F11 92.0(5) . . ?
F12 P1 F11 90.2(4) . . ?
F14 P1 F13 91.3(4) . . ?
F15 P1 F13 88.7(4) . . ?
F16 P1 F13 90.0(5) . . ?
F12 P1 F13 88.4(4) . . ?
F11 P1 F13 177.6(5) . . ?
F26 P1 F22 88.5(10) . . ?
F25 P1 F22 88.4(10) . . ?
F21 P1 F22 92.0(12) . . ?
F24 P1 F22 176.4(17) . . ?
F26 P1 F23 88.0(10) . . ?
F25 P1 F23 89.0(10) . . ?
F21 P1 F23 176.5(17) . . ?
F24 P1 F23 92.0(12) . . ?
F22 P1 F23 91.5(12) . . ?
Cl2 C10 Cl3 116.0(17) . . ?
Cl2 C10 Cl1 105.3(14) . . ?
Cl3 C10 Cl1 111.9(14) . . ?
Cl2 C10 H10 107.8 . . ?
Cl3 C10 H10 107.8 . . ?
Cl1 C10 H10 107.8 . . ?
Cl5 C20 Cl4 117(2) . . ?
Cl5 C20 Cl6 108.4(17) . . ?
Cl4 C20 Cl6 104.5(16) . . ?
Cl5 C20 H20 108.8 . . ?
Cl4 C20 H20 108.8 . . ?
Cl6 C20 H20 108.8 . . ?
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_phenestere
_database_code_depnum_ccdc_archive 'CCDC 1029148'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#


_audit_creation_date             2011-07-22T13:03:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C25 H18 F6 N6 O5 P Re'
_chemical_formula_moiety         'C25 H18 N6 O5 Re, F6 P'
_chemical_formula_weight         813.62

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_moiety '-p _2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.0672(6)
_cell_length_b                   9.8480(2)
_cell_length_c                   16.8781(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.201(4)
_cell_angle_gamma                90
_cell_volume                     2739.12(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27731
_cell_measurement_theta_min      3.6376
_cell_measurement_theta_max      36.3621

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colour
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0833
-1 0 0 0.1177
-1 1 0 0.0469
0 -2 1 0.1808
-1 -2 0 0.1904
1 2 0 0.0541
-1 0 3 0.094
0 0 -1 0.1114
1 0 -1 0.1262
-1 0 1 0.1046

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.585
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_T_max  0.483

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      -0.0128302709
_diffrn_orient_matrix_ub_12      0.0013696844
_diffrn_orient_matrix_ub_13      0.0327787547
_diffrn_orient_matrix_ub_21      -0.0437087059
_diffrn_orient_matrix_ub_22      -0.0115085037
_diffrn_orient_matrix_ub_23      -0.0273650986
_diffrn_orient_matrix_ub_31      0.0069081136
_diffrn_orient_matrix_ub_32      -0.0710648146
_diffrn_orient_matrix_ub_33      0.0051259899
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_number            81206
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         36.45
_diffrn_reflns_theta_full        36
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.968
_reflns_number_total             12974
_reflns_number_gt                8983
_reflns_threshold_expression     I>2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.
;
_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)+(0.0574P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12974
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.036
_refine_ls_wR_factor_ref         0.096
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2
_refine_diff_density_min         -1.326
_refine_diff_density_rms         0.132

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Re1 Re 0.770900(6) 0.540583(11) 0.142522(7) 0.02748(4) Uani 1 1 d . . .
C1 C 0.82675(19) 0.6940(3) 0.1212(2) 0.0341(6) Uani 1 1 d . . .
O1 O 0.86040(16) 0.7853(2) 0.10998(17) 0.0462(6) Uani 1 1 d . . .
C2 C 0.72470(17) 0.6609(3) 0.20098(19) 0.0312(6) Uani 1 1 d . . .
O2 O 0.69774(13) 0.7354(2) 0.23453(15) 0.0388(5) Uani 1 1 d . . .
C3 C 0.86370(19) 0.5164(3) 0.2512(2) 0.0300(5) Uani 1 1 d . . .
O3 O 0.91927(14) 0.5028(3) 0.31711(15) 0.0394(5) Uani 1 1 d . . .
N11 N 0.70003(16) 0.3690(3) 0.15614(19) 0.0399(6) Uani 1 1 d . . .
C12 C 0.63080(19) 0.3424(4) 0.0863(2) 0.0437(8) Uani 1 1 d . . .
C13 C 0.5768(2) 0.2327(5) 0.0858(3) 0.0590(11) Uani 1 1 d . . .
C14 C 0.5981(3) 0.1595(5) 0.1623(4) 0.0657(12) Uani 1 1 d . . .
H14 H 0.5631 0.0895 0.1652 0.079 Uiso 1 1 calc R . .
C15 C 0.6675(3) 0.1856(5) 0.2329(3) 0.0677(12) Uani 1 1 d . . .
H15 H 0.6819 0.1342 0.2847 0.081 Uiso 1 1 calc R . .
C16 C 0.7179(3) 0.2911(4) 0.2274(3) 0.0525(9) Uani 1 1 d . . .
H16 H 0.7671 0.3082 0.2765 0.063 Uiso 1 1 calc R . .
C17 C 0.5073(2) 0.2119(5) 0.0088(3) 0.0687(13) Uani 1 1 d . . .
H17 H 0.4709 0.1412 0.0068 0.082 Uiso 1 1 calc R . .
N21 N 0.66404(18) 0.5355(3) 0.01976(19) 0.0434(7) Uani 1 1 d . . .
C22 C 0.61217(19) 0.4261(4) 0.0142(3) 0.0498(10) Uani 1 1 d . . .
C23 C 0.5421(2) 0.3980(5) -0.0629(3) 0.0589(11) Uani 1 1 d . . .
C24 C 0.5775(3) 0.5878(5) -0.1298(3) 0.0654(13) Uani 1 1 d . . .
H24 H 0.5667 0.6428 -0.1795 0.079 Uiso 1 1 calc R . .
C25 C 0.5272(3) 0.4804(5) -0.1330(3) 0.0636(13) Uani 1 1 d . . .
H25 H 0.4809 0.4634 -0.1854 0.076 Uiso 1 1 calc R . .
C26 C 0.6476(3) 0.6151(5) -0.0486(2) 0.0568(10) Uani 1 1 d . . .
H26 H 0.6817 0.6906 -0.0448 0.068 Uiso 1 1 calc R . .
C27 C 0.4909(2) 0.2875(5) -0.0612(3) 0.0630(13) Uani 1 1 d . . .
H27 H 0.4436 0.2681 -0.1121 0.076 Uiso 1 1 calc R . .
N1 N 0.81476(14) 0.4080(2) 0.06565(15) 0.0273(4) Uani 1 1 d . . .
N2 N 0.80837(17) 0.4512(2) -0.01407(17) 0.0328(5) Uani 1 1 d . . .
N3 N 0.83480(15) 0.3591(3) -0.04968(16) 0.0328(5) Uani 1 1 d . . .
N4 N 0.85918(14) 0.2540(2) 0.00621(15) 0.0299(5) Uani 1 1 d . . .
C4 C 0.8920(2) 0.1300(3) -0.0141(2) 0.0387(7) Uani 1 1 d . . .
H4A H 0.8482 0.0636 -0.04 0.058 Uiso 1 1 calc R . .
H4B H 0.9337 0.0924 0.0394 0.058 Uiso 1 1 calc R . .
H4C H 0.9161 0.1507 -0.0552 0.058 Uiso 1 1 calc R . .
C5 C 0.84693(15) 0.2843(3) 0.07749(17) 0.0256(5) Uani 1 1 d . . .
C51 C 0.86616(16) 0.1940(3) 0.15270(17) 0.0268(5) Uani 1 1 d . . .
C52 C 0.93971(17) 0.2047(3) 0.2243(2) 0.0347(6) Uani 1 1 d . . .
H52 H 0.9776 0.2731 0.2265 0.042 Uiso 1 1 calc R . .
C53 C 0.95755(18) 0.1138(3) 0.2932(2) 0.0375(6) Uani 1 1 d . . .
H53 H 1.0083 0.1191 0.342 0.045 Uiso 1 1 calc R . .
C54 C 0.90146(18) 0.0161(3) 0.29058(19) 0.0282(5) Uani 1 1 d . . .
C55 C 0.8273(2) 0.0082(3) 0.2200(2) 0.0381(7) Uani 1 1 d . . .
H55 H 0.7883 -0.057 0.2194 0.046 Uiso 1 1 calc R . .
C56 C 0.8097(2) 0.0953(3) 0.1502(2) 0.0381(7) Uani 1 1 d . . .
H56 H 0.7595 0.088 0.1009 0.046 Uiso 1 1 calc R . .
C57 C 0.92457(19) -0.0828(3) 0.3649(2) 0.0335(6) Uani 1 1 d . . .
O57 O 0.99162(15) -0.0981(3) 0.41879(17) 0.0495(6) Uani 1 1 d . . .
C58 C 0.8760(2) -0.2474(4) 0.4326(2) 0.0449(8) Uani 1 1 d . . .
H58A H 0.9124 -0.3194 0.4299 0.067 Uiso 1 1 calc R . .
H58B H 0.8247 -0.2875 0.4276 0.067 Uiso 1 1 calc R . .
H58C H 0.9015 -0.1993 0.4881 0.067 Uiso 1 1 calc R . .
O58 O 0.86051(14) -0.1521(2) 0.36123(14) 0.0387(5) Uani 1 1 d . . .
P1 P 0.64519(6) 0.02781(9) 0.89667(6) 0.04136(19) Uani 1 1 d . . .
F11 F 0.6801(5) 0.0234(5) 0.8285(5) 0.197(3) Uani 1 1 d . . .
F12 F 0.5976(2) -0.1117(3) 0.8524(2) 0.0969(11) Uani 1 1 d . . .
F13 F 0.6248(3) 0.0035(5) 0.9746(3) 0.1217(17) Uani 1 1 d . . .
F14 F 0.68857(14) 0.1654(2) 0.93683(18) 0.0689(7) Uani 1 1 d . . .
F15 F 0.7213(2) -0.0608(4) 0.9489(4) 0.1254(18) Uani 1 1 d . . .
F16 F 0.5686(2) 0.1072(4) 0.8367(2) 0.1106(13) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.926(3) . ?
Re1 C1 1.930(3) . ?
Re1 C2 1.936(3) . ?
Re1 N21 2.178(3) . ?
Re1 N11 2.189(3) . ?
Re1 N1 2.204(2) . ?
C1 O1 1.145(4) . ?
C2 O2 1.150(4) . ?
C3 O3 1.161(4) . ?
N11 C12 1.347(4) . ?
N11 C16 1.349(5) . ?
C12 C22 1.391(6) . ?
C12 C13 1.453(6) . ?
C13 C14 1.389(7) . ?
C13 C17 1.403(6) . ?
C14 C15 1.355(7) . ?
C14 H14 0.95 . ?
C15 C16 1.409(5) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 C27 1.322(7) . ?
C17 H17 0.95 . ?
N21 C26 1.325(5) . ?
N21 C22 1.406(5) . ?
C22 C23 1.421(5) . ?
C23 C25 1.368(7) . ?
C23 C27 1.436(7) . ?
C24 C25 1.381(8) . ?
C24 C26 1.459(6) . ?
C24 H24 0.95 . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C27 H27 0.95 . ?
N1 C5 1.329(3) . ?
N1 N2 1.370(3) . ?
N2 N3 1.284(3) . ?
N3 N4 1.347(3) . ?
N4 C5 1.343(3) . ?
N4 C4 1.458(4) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C51 1.471(4) . ?
C51 C52 1.386(4) . ?
C51 C56 1.397(4) . ?
C52 C53 1.395(4) . ?
C52 H52 0.95 . ?
C53 C54 1.385(4) . ?
C53 H53 0.95 . ?
C54 C55 1.383(4) . ?
C54 C57 1.506(4) . ?
C55 C56 1.384(4) . ?
C55 H55 0.95 . ?
C56 H56 0.95 . ?
C57 O57 1.189(4) . ?
C57 O58 1.323(4) . ?
C58 O58 1.460(4) . ?
C58 H58A 0.98 . ?
C58 H58B 0.98 . ?
C58 H58C 0.98 . ?
P1 F11 1.523(5) . ?
P1 F13 1.523(4) . ?
P1 F16 1.550(3) . ?
P1 F15 1.561(4) . ?
P1 F14 1.573(2) . ?
P1 F12 1.631(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Re1 C1 87.51(13) . . ?
C3 Re1 C2 88.82(12) . . ?
C1 Re1 C2 89.05(12) . . ?
C3 Re1 N21 171.54(12) . . ?
C1 Re1 N21 99.68(13) . . ?
C2 Re1 N21 95.71(11) . . ?
C3 Re1 N11 97.05(12) . . ?
C1 Re1 N11 175.41(12) . . ?
C2 Re1 N11 91.50(11) . . ?
N21 Re1 N11 75.74(12) . . ?
C3 Re1 N1 96.00(10) . . ?
C1 Re1 N1 90.71(10) . . ?
C2 Re1 N1 175.16(10) . . ?
N21 Re1 N1 79.57(9) . . ?
N11 Re1 N1 88.36(9) . . ?
O1 C1 Re1 178.9(3) . . ?
O2 C2 Re1 178.1(3) . . ?
O3 C3 Re1 179.3(3) . . ?
C12 N11 C16 117.8(3) . . ?
C12 N11 Re1 115.5(2) . . ?
C16 N11 Re1 126.6(2) . . ?
N11 C12 C22 117.1(3) . . ?
N11 C12 C13 122.0(4) . . ?
C22 C12 C13 120.9(3) . . ?
C14 C13 C17 125.9(4) . . ?
C14 C13 C12 116.8(4) . . ?
C17 C13 C12 117.2(5) . . ?
C15 C14 C13 121.5(4) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 118.2(4) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
N11 C16 C15 123.6(4) . . ?
N11 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
C27 C17 C13 122.2(4) . . ?
C27 C17 H17 118.9 . . ?
C13 C17 H17 118.9 . . ?
C26 N21 C22 119.4(3) . . ?
C26 N21 Re1 127.6(3) . . ?
C22 N21 Re1 112.8(2) . . ?
C12 C22 N21 118.7(3) . . ?
C12 C22 C23 119.4(4) . . ?
N21 C22 C23 122.0(4) . . ?
C25 C23 C22 117.5(5) . . ?
C25 C23 C27 124.5(4) . . ?
C22 C23 C27 117.9(4) . . ?
C25 C24 C26 118.8(4) . . ?
C25 C24 H24 120.6 . . ?
C26 C24 H24 120.6 . . ?
C23 C25 C24 121.8(4) . . ?
C23 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
N21 C26 C24 120.5(4) . . ?
N21 C26 H26 119.8 . . ?
C24 C26 H26 119.8 . . ?
C17 C27 C23 122.3(4) . . ?
C17 C27 H27 118.9 . . ?
C23 C27 H27 118.9 . . ?
C5 N1 N2 106.7(2) . . ?
C5 N1 Re1 134.02(19) . . ?
N2 N1 Re1 119.24(17) . . ?
N3 N2 N1 110.1(2) . . ?
N2 N3 N4 107.0(2) . . ?
C5 N4 N3 109.3(2) . . ?
C5 N4 C4 129.0(3) . . ?
N3 N4 C4 121.8(2) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 N4 107.0(2) . . ?
N1 C5 C51 128.2(2) . . ?
N4 C5 C51 124.8(2) . . ?
C52 C51 C56 120.4(3) . . ?
C52 C51 C5 120.6(2) . . ?
C56 C51 C5 118.9(2) . . ?
C51 C52 C53 119.3(3) . . ?
C51 C52 H52 120.4 . . ?
C53 C52 H52 120.4 . . ?
C54 C53 C52 120.2(3) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C55 C54 C53 120.3(3) . . ?
C55 C54 C57 121.4(3) . . ?
C53 C54 C57 118.3(3) . . ?
C54 C55 C56 120.1(3) . . ?
C54 C55 H55 120 . . ?
C56 C55 H55 120 . . ?
C55 C56 C51 119.7(3) . . ?
C55 C56 H56 120.2 . . ?
C51 C56 H56 120.2 . . ?
O57 C57 O58 124.6(3) . . ?
O57 C57 C54 124.5(3) . . ?
O58 C57 C54 110.8(3) . . ?
O58 C58 H58A 109.5 . . ?
O58 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
O58 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C57 O58 C58 115.1(3) . . ?
F11 P1 F13 165.9(4) . . ?
F11 P1 F16 93.3(4) . . ?
F13 P1 F16 100.1(3) . . ?
F11 P1 F15 82.4(4) . . ?
F13 P1 F15 83.9(3) . . ?
F16 P1 F15 174.3(2) . . ?
F11 P1 F14 93.6(3) . . ?
F13 P1 F14 91.0(2) . . ?
F16 P1 F14 90.03(17) . . ?
F15 P1 F14 94.01(17) . . ?
F11 P1 F12 86.2(3) . . ?
F13 P1 F12 89.7(2) . . ?
F16 P1 F12 87.94(18) . . ?
F15 P1 F12 88.00(18) . . ?
F14 P1 F12 177.95(17) . . ?
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_bipyestere
_database_code_depnum_ccdc_archive 'CCDC 1029149'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-28 downloaded from the CCDC.
;


#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#


_audit_creation_date             2011-07-20T15:45:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C23 H18 F6 N6 O5 P Re'
_chemical_formula_moiety         'C23 H18 N6 O5 Re, F6 P'
_chemical_formula_weight         789.6

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-p 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.64680(10)
_cell_length_b                   13.10550(10)
_cell_length_c                   19.44800(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.9550(10)
_cell_angle_gamma                90
_cell_volume                     2712.03(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    68859
_cell_measurement_theta_min      3.7428
_cell_measurement_theta_max      45.5965

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.1134
0 0 -1 0.0505
0 -1 -1 0.137
1 -1 0 0.1135
-1 1 0 0.1275
0 1 1 0.1243
1 1 0 0.0771
-1 -1 0 0.1674
-1 0 2 0.1557
0 1 -1 0.105
0 -1 1 0.1232
1 0 -2 0.0626
-1 1 1 0.1356
-2 -1 1 0.1632

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.628
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.398
_exptl_absorpt_correction_T_max  0.535

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      0.013670194
_diffrn_orient_matrix_ub_12      -0.045044139
_diffrn_orient_matrix_ub_13      -0.0185452917
_diffrn_orient_matrix_ub_21      -0.0348284651
_diffrn_orient_matrix_ub_22      0.0190690085
_diffrn_orient_matrix_ub_23      -0.0289638885
_diffrn_orient_matrix_ub_31      0.0551969487
_diffrn_orient_matrix_ub_32      0.0231909008
_diffrn_orient_matrix_ub_33      -0.0121926706
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_number            181307
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         45.72
_diffrn_reflns_theta_full        45.72
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             23179
_reflns_number_gt                16765
_reflns_threshold_expression     I>2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'OrtepII (Johnson, C. K. (1976)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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.
;
_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)+(0.0189P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         23179
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.04
_refine_ls_wR_factor_gt          0.0392
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_restrained_S_all      0.874
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.39
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.11

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Re1 Re 0.729115(3) 0.201310(3) 0.100208(2) 0.012680(10) Uani 1 1 d . . .
C1 C 0.57783(9) 0.12918(8) 0.07267(5) 0.01865(17) Uani 1 1 d . . .
O1 O 0.48793(8) 0.08627(7) 0.05556(5) 0.02944(18) Uani 1 1 d . . .
C2 C 0.82110(10) 0.11991(8) 0.03655(5) 0.01948(17) Uani 1 1 d . . .
O2 O 0.87443(9) 0.06910(6) -0.00027(5) 0.02963(18) Uani 1 1 d . . .
C3 C 0.76632(9) 0.09712(8) 0.16724(5) 0.01731(16) Uani 1 1 d . . .
O3 O 0.79294(8) 0.03439(6) 0.20659(4) 0.02507(16) Uani 1 1 d . . .
N11 N 0.88951(7) 0.29763(6) 0.12551(4) 0.01467(12) Uani 1 1 d . . .
C12 C 0.89040(8) 0.39145(7) 0.09596(4) 0.01362(14) Uani 1 1 d . . .
C13 C 0.98630(9) 0.46071(8) 0.11055(5) 0.01731(16) Uani 1 1 d . . .
H13 H 0.9838 0.527 0.0907 0.021 Uiso 1 1 calc R . .
C14 C 1.08551(9) 0.43230(8) 0.15422(5) 0.02081(18) Uani 1 1 d . . .
H14 H 1.1516 0.479 0.1649 0.025 Uiso 1 1 calc R . .
C15 C 1.08742(10) 0.33496(9) 0.18230(6) 0.02284(19) Uani 1 1 d . . .
H15 H 1.156 0.3131 0.2112 0.027 Uiso 1 1 calc R . .
C16 C 0.98747(9) 0.27040(8) 0.16733(5) 0.01990(17) Uani 1 1 d . . .
H16 H 0.9878 0.2042 0.1873 0.024 Uiso 1 1 calc R . .
N21 N 0.70551(7) 0.33385(6) 0.03357(4) 0.01280(12) Uani 1 1 d . . .
C22 C 0.78718(8) 0.41177(7) 0.04537(4) 0.01279(13) Uani 1 1 d . . .
C23 C 0.77459(9) 0.50407(7) 0.01062(5) 0.01576(15) Uani 1 1 d . . .
H23 H 0.8315 0.5584 0.0203 0.019 Uiso 1 1 calc R . .
C24 C 0.67794(9) 0.51590(7) -0.03839(5) 0.01729(16) Uani 1 1 d . . .
H24 H 0.6681 0.5784 -0.0627 0.021 Uiso 1 1 calc R . .
C25 C 0.59601(9) 0.43566(8) -0.05155(5) 0.01672(16) Uani 1 1 d . . .
H25 H 0.5301 0.4417 -0.0855 0.02 Uiso 1 1 calc R . .
C26 C 0.61217(8) 0.34616(7) -0.01414(5) 0.01519(15) Uani 1 1 d . . .
H26 H 0.5551 0.2915 -0.0225 0.018 Uiso 1 1 calc R . .
N1 N 0.62084(7) 0.29875(6) 0.16851(4) 0.01493(12) Uani 1 1 d . . .
N2 N 0.50691(8) 0.33529(7) 0.14429(4) 0.01846(15) Uani 1 1 d . . .
N3 N 0.45721(8) 0.39074(7) 0.19076(4) 0.01905(15) Uani 1 1 d . . .
N4 N 0.53740(7) 0.39069(7) 0.24578(4) 0.01658(14) Uani 1 1 d . . .
C4 C 0.51067(10) 0.44840(9) 0.30787(6) 0.0232(2) Uani 1 1 d . . .
H4A H 0.5715 0.4298 0.3447 0.035 Uiso 1 1 calc R . .
H4B H 0.4255 0.4325 0.3222 0.035 Uiso 1 1 calc R . .
H4C H 0.5171 0.5216 0.2983 0.035 Uiso 1 1 calc R . .
C5 C 0.63782(8) 0.33440(7) 0.23183(5) 0.01400(14) Uani 1 1 d . . .
C51 C 0.74500(8) 0.31674(7) 0.28065(5) 0.01425(15) Uani 1 1 d . . .
C52 C 0.74838(9) 0.22808(8) 0.32009(5) 0.01651(15) Uani 1 1 d . . .
H52 H 0.6853 0.1774 0.3136 0.02 Uiso 1 1 calc R . .
C53 C 0.84500(9) 0.21455(7) 0.36912(5) 0.01672(16) Uani 1 1 d . . .
H53 H 0.8474 0.1547 0.3967 0.02 Uiso 1 1 calc R . .
C54 C 0.93806(8) 0.28821(7) 0.37799(5) 0.01487(15) Uani 1 1 d . . .
C55 C 0.93532(10) 0.37606(8) 0.33786(5) 0.01976(17) Uani 1 1 d . . .
H55 H 0.9997 0.4258 0.3435 0.024 Uiso 1 1 calc R . .
C56 C 0.83774(10) 0.39082(8) 0.28937(5) 0.02011(17) Uani 1 1 d . . .
H56 H 0.8345 0.4512 0.2624 0.024 Uiso 1 1 calc R . .
C57 C 1.03502(9) 0.27170(8) 0.43422(5) 0.01693(16) Uani 1 1 d . . .
O57 O 1.03120(7) 0.20140(6) 0.47457(4) 0.02238(14) Uani 1 1 d . . .
O58 O 1.12267(7) 0.34410(6) 0.43612(4) 0.02296(15) Uani 1 1 d . . .
C58 C 1.21574(12) 0.33576(10) 0.49165(8) 0.0333(3) Uani 1 1 d . . .
H58A H 1.1747 0.342 0.5358 0.05 Uiso 1 1 calc R . .
H58B H 1.278 0.3903 0.4876 0.05 Uiso 1 1 calc R . .
H58C H 1.2576 0.2693 0.4892 0.05 Uiso 1 1 calc R . .
P1 P 0.68674(2) 0.65999(2) 0.186174(14) 0.01829(5) Uani 1 1 d . . .
F1 F 0.67303(7) 0.54013(5) 0.17029(4) 0.03098(16) Uani 1 1 d . . .
F2 F 0.64318(9) 0.68422(6) 0.10844(4) 0.0403(2) Uani 1 1 d . . .
F3 F 0.69959(8) 0.77938(5) 0.20095(4) 0.03248(17) Uani 1 1 d . . .
F4 F 0.73009(8) 0.63446(6) 0.26360(4) 0.03531(17) Uani 1 1 d . . .
F5 F 0.82935(7) 0.65632(6) 0.16450(5) 0.0397(2) Uani 1 1 d . . .
F6 F 0.54338(7) 0.66184(7) 0.20814(5) 0.0420(2) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.9198(10) . ?
Re1 C2 1.9268(10) . ?
Re1 C1 1.9277(10) . ?
Re1 N11 2.1666(8) . ?
Re1 N21 2.1766(8) . ?
Re1 N1 2.1974(8) . ?
C1 O1 1.1495(12) . ?
C2 O2 1.1430(13) . ?
C3 O3 1.1519(12) . ?
N11 C16 1.3486(12) . ?
N11 C12 1.3574(12) . ?
C12 C13 1.3882(13) . ?
C12 C22 1.4741(12) . ?
C13 C14 1.3836(14) . ?
C13 H13 0.95 . ?
C14 C15 1.3876(16) . ?
C14 H14 0.95 . ?
C15 C16 1.3826(15) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
N21 C26 1.3460(11) . ?
N21 C22 1.3557(12) . ?
C22 C23 1.3898(13) . ?
C23 C24 1.3873(13) . ?
C23 H23 0.95 . ?
C24 C25 1.3844(14) . ?
C24 H24 0.95 . ?
C25 C26 1.3878(14) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
N1 C5 1.3239(12) . ?
N1 N2 1.3723(11) . ?
N2 N3 1.2875(12) . ?
N3 N4 1.3458(12) . ?
N4 C5 1.3343(12) . ?
N4 C4 1.4611(13) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C51 1.4775(13) . ?
C51 C56 1.3909(14) . ?
C51 C52 1.3922(13) . ?
C52 C53 1.3899(13) . ?
C52 H52 0.95 . ?
C53 C54 1.3899(13) . ?
C53 H53 0.95 . ?
C54 C55 1.3907(14) . ?
C54 C57 1.4938(13) . ?
C55 C56 1.3926(14) . ?
C55 H55 0.95 . ?
C56 H56 0.95 . ?
C57 O57 1.2118(13) . ?
C57 O58 1.3304(13) . ?
O58 C58 1.4446(14) . ?
C58 H58A 0.98 . ?
C58 H58B 0.98 . ?
C58 H58C 0.98 . ?
P1 F5 1.5903(8) . ?
P1 F4 1.5953(8) . ?
P1 F3 1.5958(7) . ?
P1 F2 1.5980(8) . ?
P1 F6 1.5991(8) . ?
P1 F1 1.6066(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
C3 Re1 C2 86.84(4) . . ?
C3 Re1 C1 89.48(4) . . ?
C2 Re1 C1 89.32(4) . . ?
C3 Re1 N11 96.74(4) . . ?
C2 Re1 N11 93.13(4) . . ?
C1 Re1 N11 173.42(4) . . ?
C3 Re1 N21 171.44(4) . . ?
C2 Re1 N21 96.32(4) . . ?
C1 Re1 N21 98.48(3) . . ?
N11 Re1 N21 75.19(3) . . ?
C3 Re1 N1 95.92(4) . . ?
C2 Re1 N1 177.18(4) . . ?
C1 Re1 N1 90.13(4) . . ?
N11 Re1 N1 87.12(3) . . ?
N21 Re1 N1 81.02(3) . . ?
O1 C1 Re1 179.30(9) . . ?
O2 C2 Re1 177.99(9) . . ?
O3 C3 Re1 177.54(9) . . ?
C16 N11 C12 118.59(8) . . ?
C16 N11 Re1 124.76(7) . . ?
C12 N11 Re1 116.65(6) . . ?
N11 C12 C13 121.43(8) . . ?
N11 C12 C22 115.49(8) . . ?
C13 C12 C22 123.00(8) . . ?
C14 C13 C12 119.36(9) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.31(9) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 118.61(9) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N11 C16 C15 122.61(10) . . ?
N11 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C26 N21 C22 118.73(8) . . ?
C26 N21 Re1 125.01(6) . . ?
C22 N21 Re1 116.10(6) . . ?
N21 C22 C23 121.50(8) . . ?
N21 C22 C12 115.86(8) . . ?
C23 C22 C12 122.62(8) . . ?
C24 C23 C22 119.23(9) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 119.34(9) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 118.62(9) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
N21 C26 C25 122.55(9) . . ?
N21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C5 N1 N2 106.69(8) . . ?
C5 N1 Re1 135.20(6) . . ?
N2 N1 Re1 118.11(6) . . ?
N3 N2 N1 109.62(8) . . ?
N2 N3 N4 107.04(8) . . ?
C5 N4 N3 109.25(8) . . ?
C5 N4 C4 129.36(8) . . ?
N3 N4 C4 121.37(8) . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 N4 107.41(8) . . ?
N1 C5 C51 128.35(8) . . ?
N4 C5 C51 124.24(8) . . ?
C56 C51 C52 120.70(9) . . ?
C56 C51 C5 119.90(8) . . ?
C52 C51 C5 119.32(8) . . ?
C53 C52 C51 119.28(9) . . ?
C53 C52 H52 120.4 . . ?
C51 C52 H52 120.4 . . ?
C54 C53 C52 120.29(9) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C53 C54 C55 120.27(9) . . ?
C53 C54 C57 117.53(9) . . ?
C55 C54 C57 122.11(9) . . ?
C54 C55 C56 119.73(9) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C51 C56 C55 119.72(9) . . ?
C51 C56 H56 120.1 . . ?
C55 C56 H56 120.1 . . ?
O57 C57 O58 124.28(9) . . ?
O57 C57 C54 123.13(9) . . ?
O58 C57 C54 112.56(9) . . ?
C57 O58 C58 115.43(10) . . ?
O58 C58 H58A 109.5 . . ?
O58 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
O58 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
F5 P1 F4 89.75(5) . . ?
F5 P1 F3 90.03(4) . . ?
F4 P1 F3 90.88(4) . . ?
F5 P1 F2 90.24(5) . . ?
F4 P1 F2 179.35(5) . . ?
F3 P1 F2 89.77(4) . . ?
F5 P1 F6 179.13(5) . . ?
F4 P1 F6 89.95(5) . . ?
F3 P1 F6 90.79(5) . . ?
F2 P1 F6 90.06(5) . . ?
F5 P1 F1 90.04(4) . . ?
F4 P1 F1 89.88(4) . . ?
F3 P1 F1 179.24(5) . . ?
F2 P1 F1 89.47(4) . . ?
F6 P1 F1 89.14(5) . . ?
#===END



