# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 N5 O4 Re'
_chemical_formula_weight         586.57

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'
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/c

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

_cell_length_a                   17.7605(3)
_cell_length_b                   8.06550(10)
_cell_length_c                   14.5295(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.4690(10)
_cell_angle_gamma                90.00
_cell_volume                     2080.63(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.15
_cell_measurement_theta_max      27.50

_exptl_crystal_description       parallopiped
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    5.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.187
_exptl_absorpt_correction_T_max  0.230
_exptl_absorpt_process_details   (SADABAS,SHELDRICK-1997)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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            33815
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4785
_reflns_number_gt                3572
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0439P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4785
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 0.3636(4) 0.4163(7) -0.0419(4) 0.0497(15) Uani 1 1 d . . .
C3 C 0.4746(4) 0.2367(7) 0.0337(4) 0.0485(16) Uani 1 1 d . . .
C2 C 0.4071(4) 0.4638(7) 0.1311(4) 0.0559(17) Uani 1 1 d . . .
C4 C 0.2608(4) 0.0140(7) 0.0263(4) 0.0457(14) Uani 1 1 d . . .
C5 C 0.2277(4) -0.1380(7) 0.0074(4) 0.0570(17) Uani 1 1 d . . .
H5 H 0.2551 -0.2203 -0.0216 0.068 Uiso 1 1 calc R . .
C6 C 0.1537(4) -0.1683(9) 0.0314(5) 0.0619(18) Uani 1 1 d . . .
H6 H 0.1329 -0.2718 0.0183 0.074 Uiso 1 1 calc R . .
C7 C 0.1102(4) -0.0522(8) 0.0734(4) 0.0531(16) Uani 1 1 d . . .
C8 C 0.1403(4) 0.1071(7) 0.0930(4) 0.0477(15) Uani 1 1 d . . .
C9 C 0.1010(4) 0.2404(8) 0.1335(5) 0.065(2) Uani 1 1 d . . .
H9 H 0.0507 0.2285 0.1485 0.078 Uiso 1 1 calc R . .
C10 C 0.1372(4) 0.3847(9) 0.1501(5) 0.0648(19) Uani 1 1 d . . .
H10 H 0.1113 0.4733 0.1752 0.078 Uiso 1 1 calc R . .
C11 C 0.2130(4) 0.4023(8) 0.1301(4) 0.0610(18) Uani 1 1 d . . .
H11 H 0.2369 0.5023 0.1438 0.073 Uiso 1 1 calc R . .
C12 C 0.2167(3) 0.1361(7) 0.0716(4) 0.0422(14) Uani 1 1 d . . .
C13 C 0.3967(4) -0.0462(8) 0.1877(4) 0.0562(17) Uani 1 1 d . . .
H13 H 0.4086 -0.1090 0.1365 0.067 Uiso 1 1 calc R . .
C14 C 0.3952(4) -0.1032(8) 0.2747(4) 0.0595(18) Uani 1 1 d . . .
H14 H 0.4062 -0.2101 0.2947 0.071 Uiso 1 1 calc R . .
C15 C 0.3642(4) 0.1547(8) 0.2721(4) 0.0545(16) Uani 1 1 d . . .
H15 H 0.3491 0.2590 0.2918 0.065 Uiso 1 1 calc R . .
C16 C -0.0641(4) -0.2410(9) 0.1229(5) 0.064(2) Uani 1 1 d . . .
C17 C -0.1043(5) -0.1217(11) 0.1682(5) 0.080(2) Uani 1 1 d . . .
H17 H -0.0828 -0.0184 0.1798 0.096 Uiso 1 1 calc R . .
C18 C -0.1762(5) -0.1549(11) 0.1965(5) 0.078(2) Uani 1 1 d . . .
H18 H -0.2034 -0.0757 0.2282 0.094 Uiso 1 1 calc R . .
C19 C -0.2068(5) -0.3066(12) 0.1768(6) 0.080(2) Uani 1 1 d . . .
H19 H -0.2555 -0.3291 0.1950 0.096 Uiso 1 1 calc R . .
C20 C -0.1684(5) -0.4254(11) 0.1318(6) 0.085(3) Uani 1 1 d . . .
H20 H -0.1907 -0.5277 0.1195 0.102 Uiso 1 1 calc R . .
C21 C -0.0962(4) -0.3937(10) 0.1045(5) 0.073(2) Uani 1 1 d . . .
H21 H -0.0692 -0.4746 0.0738 0.088 Uiso 1 1 calc R . .
N1 N 0.2519(3) 0.2833(6) 0.0927(4) 0.0485(13) Uani 1 1 d . . .
N2 N 0.3781(3) 0.1173(5) 0.1864(3) 0.0408(11) Uani 1 1 d . . .
N3 N 0.3744(3) 0.0262(7) 0.3267(4) 0.0551(16) Uani 1 1 d . . .
N4 N 0.0351(3) -0.0748(7) 0.1022(4) 0.0592(14) Uani 1 1 d . . .
N5 N 0.0096(4) -0.2215(7) 0.0905(5) 0.0703(17) Uani 1 1 d . . .
O1 O 0.3599(3) 0.5048(5) -0.1039(3) 0.0700(14) Uani 1 1 d . . .
O3 O 0.5364(3) 0.2145(6) 0.0132(4) 0.0723(14) Uani 1 1 d . . .
O2 O 0.4284(3) 0.5756(6) 0.1737(4) 0.0930(18) Uani 1 1 d . . .
O4 O 0.3296(2) 0.0513(5) 0.0047(2) 0.0450(10) Uani 1 1 d . . .
Re1 Re 0.372590(13) 0.27673(3) 0.064036(15) 0.03944(9) Uani 1 1 d . . .
H3 H 0.366(3) 0.020(6) 0.374(4) 0.020(15) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.066(4) 0.047(4) 0.036(3) -0.002(3) -0.002(3) -0.008(3)
C3 0.075(5) 0.039(3) 0.032(3) 0.003(2) 0.009(3) 0.005(3)
C2 0.096(5) 0.035(3) 0.037(3) 0.005(3) 0.005(4) 0.001(3)
C4 0.058(4) 0.045(3) 0.034(3) 0.000(3) -0.002(3) 0.004(3)
C5 0.078(5) 0.037(4) 0.056(4) -0.013(3) 0.007(4) -0.004(3)
C6 0.068(5) 0.050(4) 0.067(5) -0.012(4) 0.003(4) -0.006(3)
C7 0.061(4) 0.058(4) 0.041(4) 0.001(3) 0.002(3) -0.005(3)
C8 0.060(4) 0.047(4) 0.036(3) -0.001(3) -0.001(3) 0.002(3)
C9 0.066(5) 0.067(5) 0.062(5) 0.006(4) 0.014(4) 0.016(4)
C10 0.069(5) 0.060(4) 0.067(5) -0.018(4) 0.016(4) 0.006(4)
C11 0.091(5) 0.039(3) 0.052(4) -0.011(3) 0.005(4) 0.006(3)
C12 0.061(4) 0.033(3) 0.032(3) 0.001(2) 0.000(3) 0.004(3)
C13 0.086(5) 0.044(4) 0.039(3) 0.002(3) 0.012(3) 0.019(3)
C14 0.103(5) 0.038(3) 0.038(3) 0.008(3) 0.003(4) 0.015(3)
C15 0.095(5) 0.040(3) 0.029(3) 0.000(3) 0.007(3) 0.005(3)
C16 0.058(4) 0.084(6) 0.049(4) 0.007(4) -0.003(4) -0.015(4)
C17 0.081(6) 0.097(7) 0.063(5) -0.016(5) 0.003(4) -0.023(5)
C18 0.083(6) 0.097(6) 0.055(5) -0.012(5) -0.005(4) -0.002(5)
C19 0.063(5) 0.117(7) 0.058(5) 0.011(5) -0.006(4) -0.019(5)
C20 0.082(6) 0.089(6) 0.085(6) -0.003(5) -0.005(5) -0.034(5)
C21 0.069(5) 0.080(6) 0.071(5) 0.000(4) 0.000(4) -0.016(4)
N1 0.068(3) 0.037(3) 0.041(3) 0.006(2) 0.004(3) 0.005(2)
N2 0.065(3) 0.037(3) 0.020(2) 0.0013(19) 0.005(2) 0.000(2)
N3 0.087(5) 0.053(3) 0.025(3) 0.002(3) 0.006(3) 0.002(3)
N4 0.059(4) 0.070(4) 0.048(3) 0.002(3) -0.004(3) -0.012(3)
N5 0.075(4) 0.067(4) 0.069(4) -0.002(3) -0.002(3) -0.013(3)
O1 0.099(4) 0.061(3) 0.049(3) 0.028(2) -0.014(3) -0.020(3)
O3 0.071(4) 0.079(4) 0.067(4) 0.006(3) 0.015(3) 0.008(3)
O2 0.163(6) 0.048(3) 0.067(3) -0.015(3) -0.013(4) -0.014(3)
O4 0.065(3) 0.043(2) 0.027(2) -0.0034(17) 0.002(2) -0.001(2)
Re1 0.06045(17) 0.03130(13) 0.02673(13) 0.00187(9) 0.00426(10) -0.00006(11)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.150(7) . ?
C1 Re1 1.910(6) . ?
C3 O3 1.157(8) . ?
C3 Re1 1.904(8) . ?
C2 O2 1.152(7) . ?
C2 Re1 1.889(6) . ?
C4 O4 1.303(7) . ?
C4 C5 1.384(8) . ?
C4 C12 1.429(7) . ?
C5 C6 1.390(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.418(8) . ?
C7 N4 1.420(8) . ?
C8 C9 1.417(8) . ?
C8 C12 1.420(8) . ?
C9 C10 1.348(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(9) . ?
C10 H10 0.9300 . ?
C11 N1 1.309(7) . ?
C11 H11 0.9300 . ?
C12 N1 1.373(7) . ?
C13 C14 1.345(8) . ?
C13 N2 1.360(7) . ?
C13 H13 0.9300 . ?
C14 N3 1.345(8) . ?
C14 H14 0.9300 . ?
C15 N2 1.311(7) . ?
C15 N3 1.315(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(10) . ?
C16 C21 1.380(9) . ?
C16 N5 1.413(9) . ?
C17 C18 1.378(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.353(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(10) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 Re1 2.195(6) . ?
N2 Re1 2.194(4) . ?
N3 H3 0.70(5) . ?
N4 N5 1.277(7) . ?
O4 Re1 2.144(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
O1 C1 Re1 177.3(5) . . ?
O3 C3 Re1 178.2(6) . . ?
O2 C2 Re1 178.5(6) . . ?
O4 C4 C5 123.6(6) . . ?
O4 C4 C12 118.6(5) . . ?
C5 C4 C12 117.8(6) . . ?
C4 C5 C6 120.4(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 122.7(6) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C8 119.8(6) . . ?
C6 C7 N4 126.1(6) . . ?
C8 C7 N4 114.1(6) . . ?
C9 C8 C7 125.8(6) . . ?
C9 C8 C12 116.7(6) . . ?
C7 C8 C12 117.5(6) . . ?
C10 C9 C8 119.5(7) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.7(6) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
N1 C11 C10 122.4(6) . . ?
N1 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
N1 C12 C8 121.7(5) . . ?
N1 C12 C4 116.6(5) . . ?
C8 C12 C4 121.8(5) . . ?
C14 C13 N2 109.5(5) . . ?
C14 C13 H13 125.2 . . ?
N2 C13 H13 125.2 . . ?
C13 C14 N3 106.0(5) . . ?
C13 C14 H14 127.0 . . ?
N3 C14 H14 127.0 . . ?
N2 C15 N3 111.4(6) . . ?
N2 C15 H15 124.3 . . ?
N3 C15 H15 124.3 . . ?
C17 C16 C21 120.0(7) . . ?
C17 C16 N5 125.3(7) . . ?
C21 C16 N5 114.6(7) . . ?
C16 C17 C18 120.2(8) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 118.5(8) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C20 C19 C18 122.2(8) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C19 C20 C21 119.5(8) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C16 119.5(8) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
C11 N1 C12 119.0(6) . . ?
C11 N1 Re1 128.7(5) . . ?
C12 N1 Re1 112.2(4) . . ?
C15 N2 C13 105.1(5) . . ?
C15 N2 Re1 129.0(4) . . ?
C13 N2 Re1 125.9(4) . . ?
C15 N3 C14 107.9(5) . . ?
C15 N3 H3 127(4) . . ?
C14 N3 H3 124(4) . . ?
N5 N4 C7 114.3(6) . . ?
N4 N5 C16 112.7(6) . . ?
C4 O4 Re1 115.2(3) . . ?
C2 Re1 C3 87.5(3) . . ?
C2 Re1 C1 87.9(2) . . ?
C3 Re1 C1 88.5(3) . . ?
C2 Re1 O4 172.6(2) . . ?
C3 Re1 O4 95.5(2) . . ?
C1 Re1 O4 98.9(2) . . ?
C2 Re1 N2 92.5(2) . . ?
C3 Re1 N2 93.7(2) . . ?
C1 Re1 N2 177.7(2) . . ?
O4 Re1 N2 80.61(15) . . ?
C2 Re1 N1 100.9(3) . . ?
C3 Re1 N1 171.2(2) . . ?
C1 Re1 N1 94.4(2) . . ?
O4 Re1 N1 75.92(17) . . ?
N2 Re1 N1 83.35(17) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.714
_refine_diff_density_min         -1.376
_refine_diff_density_rms         0.179
_database_code_depnum_ccdc_archive 'CCDC 941411'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N5 O4 Re'
_chemical_formula_weight         600.60

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.2633(3)
_cell_length_b                   13.3774(6)
_cell_length_c                   15.3577(7)
_cell_angle_alpha                66.642(2)
_cell_angle_beta                 81.680(2)
_cell_angle_gamma                79.222(2)
_cell_volume                     1156.92(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      27.38

_exptl_crystal_description       parallopiped
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    5.288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_T_max  0.267
_exptl_absorpt_process_details   (SADABAS,SHELDRICK-1997)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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            18278
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.38
_reflns_number_total             5184
_reflns_number_gt                4132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

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

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.093 0.500 1.000 155 59 ' '
_platon_squeeze_details          
;
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0711P)^2^+4.9552P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5184
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.4602(18) 0.1305(9) 0.5323(8) 0.048(3) Uani 1 1 d . . .
C2 C 0.0615(19) 0.2295(10) 0.5662(9) 0.055(3) Uani 1 1 d . . .
C3 C 0.4093(17) 0.3333(9) 0.5301(8) 0.047(2) Uani 1 1 d . . .
C4 C 0.4547(16) 0.2753(7) 0.2751(7) 0.038(2) Uani 1 1 d . . .
C5 C 0.579(2) 0.2973(9) 0.1873(8) 0.055(3) Uani 1 1 d . . .
H5 H 0.6931 0.3383 0.1734 0.066 Uiso 1 1 calc R . .
C6 C 0.536(2) 0.2588(9) 0.1212(8) 0.055(3) Uani 1 1 d . . .
H6 H 0.6245 0.2723 0.0649 0.066 Uiso 1 1 calc R . .
C7 C 0.3630(18) 0.2008(8) 0.1366(7) 0.046(2) Uani 1 1 d . . .
C8 C 0.2330(17) 0.1744(7) 0.2249(7) 0.039(2) Uani 1 1 d . . .
C9 C 0.0584(17) 0.1147(8) 0.2501(8) 0.044(2) Uani 1 1 d . . .
H9 H 0.0190 0.0884 0.2079 0.053 Uiso 1 1 calc R . .
C10 C -0.0549(16) 0.0948(8) 0.3370(7) 0.043(2) Uani 1 1 d . . .
H10 H -0.1702 0.0541 0.3546 0.051 Uiso 1 1 calc R . .
C11 C 0.0047(17) 0.1365(8) 0.3994(8) 0.044(2) Uani 1 1 d . . .
H11 H -0.0738 0.1230 0.4582 0.052 Uiso 1 1 calc R . .
C12 C 0.2825(16) 0.2136(7) 0.2921(7) 0.036(2) Uani 1 1 d . . .
C13 C 0.116(2) 0.5216(9) 0.3594(9) 0.059(3) Uani 1 1 d . . .
H13 H 0.2269 0.5408 0.3816 0.070 Uiso 1 1 calc R . .
C14 C -0.035(2) 0.5919(9) 0.3022(10) 0.063(3) Uani 1 1 d . . .
H14 H -0.0473 0.6683 0.2769 0.076 Uiso 1 1 calc R . .
C15 C -0.0946(19) 0.4229(9) 0.3383(8) 0.049(3) Uani 1 1 d . . .
H15 H -0.1579 0.3633 0.3427 0.059 Uiso 1 1 calc R . .
C16 C 0.3820(19) 0.1416(8) -0.0699(7) 0.047(2) Uani 1 1 d . . .
C17 C 0.187(2) 0.1064(10) -0.0677(8) 0.062(3) Uani 1 1 d . . .
H17 H 0.0781 0.1068 -0.0196 0.074 Uiso 1 1 calc R . .
C18 C 0.153(2) 0.0708(11) -0.1364(9) 0.062(3) Uani 1 1 d . . .
H18 H 0.0213 0.0469 -0.1338 0.074 Uiso 1 1 calc R . .
C19 C 0.309(2) 0.0698(11) -0.2087(9) 0.063(3) Uani 1 1 d . . .
H19 H 0.2847 0.0450 -0.2545 0.075 Uiso 1 1 calc R . .
C20 C 0.503(2) 0.1064(10) -0.2118(8) 0.061(3) Uani 1 1 d . . .
H20 H 0.6098 0.1068 -0.2606 0.073 Uiso 1 1 calc R . .
C21 C 0.540(2) 0.1426(9) -0.1431(8) 0.050(3) Uani 1 1 d . . .
H21 H 0.6710 0.1674 -0.1461 0.060 Uiso 1 1 calc R . .
C22 C -0.357(2) 0.5701(10) 0.2314(9) 0.068(4) Uani 1 1 d . . .
H22A H -0.4182 0.5083 0.2342 0.103 Uiso 1 1 calc R . .
H22B H -0.3119 0.6122 0.1665 0.103 Uiso 1 1 calc R . .
H22C H -0.4636 0.6155 0.2562 0.103 Uiso 1 1 calc R . .
N1 N 0.1662(13) 0.1935(6) 0.3779(5) 0.0352(17) Uani 1 1 d . . .
N2 N 0.0793(14) 0.4174(6) 0.3793(7) 0.046(2) Uani 1 1 d . . .
N3 N -0.1668(16) 0.5309(7) 0.2882(7) 0.051(2) Uani 1 1 d . . .
N4 N 0.3072(16) 0.1615(7) 0.0706(6) 0.049(2) Uani 1 1 d . . .
N5 N 0.4341(17) 0.1803(8) -0.0031(7) 0.057(2) Uani 1 1 d . . .
O1 O 0.5643(14) 0.0472(7) 0.5754(6) 0.065(2) Uani 1 1 d . . .
O2 O -0.0698(16) 0.2053(8) 0.6287(7) 0.075(3) Uani 1 1 d . . .
O3 O 0.4892(15) 0.3742(8) 0.5668(7) 0.070(2) Uani 1 1 d . . .
O4 O 0.4940(11) 0.3094(6) 0.3387(5) 0.0434(16) Uani 1 1 d . . .
Re1 Re 0.28220(7) 0.26417(3) 0.46505(3) 0.03669(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.038(6) 0.057(6) 0.054(6) -0.026(5) 0.001(5) -0.015(5)
C2 0.034(6) 0.077(8) 0.074(8) -0.044(7) -0.037(6) 0.010(6)
C3 0.037(6) 0.060(6) 0.054(6) -0.028(5) -0.008(5) -0.012(5)
C4 0.030(5) 0.038(5) 0.052(6) -0.020(4) -0.004(4) -0.007(4)
C5 0.054(7) 0.060(7) 0.059(7) -0.027(6) 0.006(6) -0.023(6)
C6 0.063(8) 0.065(7) 0.045(6) -0.023(5) 0.006(6) -0.029(6)
C7 0.039(6) 0.049(6) 0.051(6) -0.022(5) -0.001(5) -0.005(5)
C8 0.038(6) 0.035(5) 0.047(5) -0.016(4) -0.014(5) -0.005(4)
C9 0.042(6) 0.048(6) 0.055(6) -0.026(5) -0.008(5) -0.015(5)
C10 0.030(5) 0.049(5) 0.057(6) -0.023(5) -0.004(5) -0.016(4)
C11 0.037(6) 0.041(5) 0.056(6) -0.017(5) -0.014(5) -0.009(4)
C12 0.031(5) 0.035(4) 0.047(5) -0.018(4) -0.008(4) -0.002(4)
C13 0.055(8) 0.046(6) 0.086(9) -0.029(6) -0.013(7) -0.019(6)
C14 0.065(9) 0.037(6) 0.086(9) -0.018(6) -0.006(7) -0.017(6)
C15 0.049(7) 0.046(6) 0.058(6) -0.015(5) -0.018(5) -0.016(5)
C16 0.052(7) 0.046(5) 0.046(6) -0.018(5) -0.003(5) -0.009(5)
C17 0.063(8) 0.080(8) 0.046(6) -0.031(6) 0.012(6) -0.017(7)
C18 0.052(8) 0.089(9) 0.062(7) -0.042(7) -0.005(6) -0.023(7)
C19 0.068(9) 0.075(8) 0.054(7) -0.032(6) -0.002(6) -0.016(7)
C20 0.065(9) 0.065(7) 0.052(7) -0.027(6) 0.012(6) -0.010(6)
C21 0.050(7) 0.052(6) 0.055(6) -0.027(5) 0.008(5) -0.015(5)
C22 0.073(9) 0.051(7) 0.071(8) -0.005(6) -0.034(7) -0.002(6)
N1 0.034(4) 0.040(4) 0.034(4) -0.016(3) 0.000(3) -0.008(3)
N2 0.035(5) 0.036(4) 0.069(6) -0.026(4) 0.007(4) -0.006(4)
N3 0.060(6) 0.037(4) 0.060(5) -0.020(4) -0.017(5) 0.001(4)
N4 0.057(6) 0.051(5) 0.039(5) -0.015(4) -0.005(4) -0.013(4)
N5 0.066(7) 0.064(6) 0.049(5) -0.027(5) 0.000(5) -0.018(5)
O1 0.059(6) 0.056(5) 0.076(5) -0.032(4) -0.019(5) 0.025(4)
O2 0.066(6) 0.086(6) 0.067(6) -0.028(5) 0.022(5) -0.023(5)
O3 0.067(6) 0.091(6) 0.081(6) -0.052(5) -0.008(5) -0.031(5)
O4 0.041(4) 0.052(4) 0.049(4) -0.026(3) 0.001(3) -0.022(3)
Re1 0.0345(2) 0.0385(2) 0.0432(2) -0.01991(17) -0.00523(16) -0.00802(15)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.172(13) . ?
C1 Re1 1.905(12) . ?
C2 O2 1.152(15) . ?
C2 Re1 1.894(14) . ?
C3 O3 1.138(12) . ?
C3 Re1 1.930(10) . ?
C4 O4 1.299(11) . ?
C4 C5 1.407(14) . ?
C4 C12 1.412(13) . ?
C5 C6 1.385(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(15) . ?
C6 H6 0.9300 . ?
C7 N4 1.420(13) . ?
C7 C8 1.427(14) . ?
C8 C9 1.394(13) . ?
C8 C12 1.420(13) . ?
C9 C10 1.367(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(13) . ?
C10 H10 0.9300 . ?
C11 N1 1.307(12) . ?
C11 H11 0.9300 . ?
C12 N1 1.362(12) . ?
C13 C14 1.345(17) . ?
C13 N2 1.362(12) . ?
C13 H13 0.9300 . ?
C14 N3 1.354(15) . ?
C14 H14 0.9300 . ?
C15 N2 1.310(14) . ?
C15 N3 1.363(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(16) . ?
C16 C21 1.383(15) . ?
C16 N5 1.416(13) . ?
C17 C18 1.372(15) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(17) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(18) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(15) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 N3 1.468(15) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 Re1 2.180(7) . ?
N2 Re1 2.218(9) . ?
N4 N5 1.251(12) . ?
O4 Re1 2.125(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
O1 C1 Re1 178.0(10) . . ?
O2 C2 Re1 178.0(11) . . ?
O3 C3 Re1 178.1(10) . . ?
O4 C4 C5 122.4(9) . . ?
O4 C4 C12 120.6(9) . . ?
C5 C4 C12 117.1(9) . . ?
C6 C5 C4 121.2(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 121.8(10) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 N4 124.4(9) . . ?
C6 C7 C8 119.5(10) . . ?
N4 C7 C8 116.1(9) . . ?
C9 C8 C12 117.2(9) . . ?
C9 C8 C7 125.2(9) . . ?
C12 C8 C7 117.6(9) . . ?
C10 C9 C8 119.9(9) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.3(9) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
N1 C11 C10 122.5(10) . . ?
N1 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
N1 C12 C4 115.4(8) . . ?
N1 C12 C8 121.9(9) . . ?
C4 C12 C8 122.7(9) . . ?
C14 C13 N2 108.0(10) . . ?
C14 C13 H13 126.0 . . ?
N2 C13 H13 126.0 . . ?
C13 C14 N3 107.3(10) . . ?
C13 C14 H14 126.4 . . ?
N3 C14 H14 126.4 . . ?
N2 C15 N3 108.4(9) . . ?
N2 C15 H15 125.8 . . ?
N3 C15 H15 125.8 . . ?
C17 C16 C21 119.1(10) . . ?
C17 C16 N5 124.9(10) . . ?
C21 C16 N5 116.0(10) . . ?
C18 C17 C16 120.1(11) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 121.6(12) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 118.5(11) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C21 120.9(11) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 119.9(11) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 N1 C12 119.2(8) . . ?
C11 N1 Re1 127.7(7) . . ?
C12 N1 Re1 113.1(6) . . ?
C15 N2 C13 108.6(9) . . ?
C15 N2 Re1 125.9(7) . . ?
C13 N2 Re1 125.6(8) . . ?
C14 N3 C15 107.8(10) . . ?
C14 N3 C22 127.8(10) . . ?
C15 N3 C22 124.4(9) . . ?
N5 N4 C7 113.9(9) . . ?
N4 N5 C16 114.9(10) . . ?
C4 O4 Re1 114.7(6) . . ?
C2 Re1 C1 89.8(5) . . ?
C2 Re1 C3 88.7(4) . . ?
C1 Re1 C3 87.8(5) . . ?
C2 Re1 O4 172.0(3) . . ?
C1 Re1 O4 95.9(4) . . ?
C3 Re1 O4 97.1(4) . . ?
C2 Re1 N1 97.8(4) . . ?
C1 Re1 N1 93.0(4) . . ?
C3 Re1 N1 173.4(4) . . ?
O4 Re1 N1 76.3(3) . . ?
C2 Re1 N2 92.4(4) . . ?
C1 Re1 N2 176.6(4) . . ?
C3 Re1 N2 94.8(4) . . ?
O4 Re1 N2 81.6(3) . . ?
N1 Re1 N2 84.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.38
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         2.834
_refine_diff_density_min         -1.575
_refine_diff_density_rms         0.198
_database_code_depnum_ccdc_archive 'CCDC 941412'