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

#######################################################################
#
#                 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_sjp1010
#TrackingRef 'Re-oBr_sjp1010.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 Br N4 O4 Re, C F3 O3 S'
_chemical_formula_sum            'C26 H17 Br F3 N4 O7 Re S'
_chemical_formula_weight         852.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   12.2430(3)
_cell_length_b                   12.0173(2)
_cell_length_c                   19.2931(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.5490(10)
_cell_angle_gamma                90.00
_cell_volume                     2781.08(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5195
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.036
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1640
_exptl_absorpt_coefficient_mu    5.955
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.1992
_exptl_absorpt_correction_T_max  0.5351
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10634
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6359
_reflns_number_gt                5195
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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)+(0.0425P)²+11.8336P] 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     SHELXL
_refine_ls_extinction_coef       0.00190(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6359
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.5131(5) -0.2897(5) 0.3647(4) 0.0350(14) Uani 1 1 d . . .
C2 C 0.4639(6) -0.3505(5) 0.3048(4) 0.0369(15) Uani 1 1 d . . .
C3 C 0.4926(6) -0.4585(6) 0.2947(4) 0.0441(17) Uani 1 1 d . . .
H3 H 0.4586 -0.4977 0.2532 0.053 Uiso 1 1 calc R . .
C4 C 0.5718(7) -0.5096(6) 0.3460(5) 0.058(2) Uani 1 1 d . . .
H4 H 0.5917 -0.5849 0.3402 0.069 Uiso 1 1 calc R . .
C5 C 0.6221(7) -0.4516(7) 0.4054(5) 0.060(2) Uani 1 1 d . . .
H5 H 0.6768 -0.4868 0.4404 0.072 Uiso 1 1 calc R . .
C6 C 0.5926(6) -0.3420(6) 0.4140(4) 0.0452(17) Uani 1 1 d . . .
H6 H 0.6283 -0.3022 0.4549 0.054 Uiso 1 1 calc R . .
C7 C 0.5440(5) -0.0960(5) 0.4029(3) 0.0332(14) Uani 1 1 d . . .
C8 C 0.4906(5) 0.0160(5) 0.4083(3) 0.0300(13) Uani 1 1 d . . .
C9 C 0.5600(5) 0.1079(5) 0.4278(4) 0.0361(14) Uani 1 1 d . . .
H9 H 0.6387 0.0990 0.4386 0.043 Uiso 1 1 calc R . .
C10 C 0.5134(6) 0.2108(5) 0.4313(4) 0.0386(15) Uani 1 1 d . . .
H10 H 0.5596 0.2738 0.4448 0.046 Uiso 1 1 calc R . .
C11 C 0.3996(6) 0.2227(5) 0.4151(3) 0.0346(14) Uani 1 1 d . . .
H11 H 0.3690 0.2953 0.4160 0.042 Uiso 1 1 calc R . .
C12 C 0.3763(5) 0.0338(5) 0.3947(3) 0.0263(12) Uani 1 1 d . . .
H12 H 0.3284 -0.0283 0.3824 0.032 Uiso 1 1 calc R . .
C13 C 0.1770(5) 0.3785(5) 0.3084(3) 0.0285(12) Uani 1 1 d . . .
H13 H 0.1788 0.4110 0.3535 0.034 Uiso 1 1 calc R . .
C14 C 0.1909(5) 0.4468(5) 0.2522(3) 0.0342(14) Uani 1 1 d . . .
H14 H 0.2004 0.5248 0.2588 0.041 Uiso 1 1 calc R . .
C15 C 0.1906(6) 0.3996(5) 0.1871(3) 0.0391(15) Uani 1 1 d . . .
H15 H 0.2004 0.4444 0.1483 0.047 Uiso 1 1 calc R . .
C16 C 0.1759(6) 0.2850(5) 0.1792(3) 0.0328(14) Uani 1 1 d . . .
H16 H 0.1755 0.2508 0.1347 0.039 Uiso 1 1 calc R . .
C17 C 0.1618(5) 0.2217(4) 0.2363(3) 0.0244(12) Uani 1 1 d . . .
C18 C 0.1421(5) 0.1000(5) 0.2324(3) 0.0250(11) Uani 1 1 d . . .
C19 C 0.1288(6) 0.0407(5) 0.1698(3) 0.0337(14) Uani 1 1 d . . .
H19 H 0.1324 0.0775 0.1267 0.040 Uiso 1 1 calc R . .
C20 C 0.1103(6) -0.0728(5) 0.1708(3) 0.0378(15) Uani 1 1 d . . .
H20 H 0.1025 -0.1151 0.1285 0.045 Uiso 1 1 calc R . .
C21 C 0.1032(5) -0.1237(5) 0.2336(3) 0.0325(14) Uani 1 1 d . . .
H21 H 0.0905 -0.2016 0.2353 0.039 Uiso 1 1 calc R . .
C22 C 0.1148(5) -0.0603(4) 0.2940(3) 0.0287(13) Uani 1 1 d . . .
H22 H 0.1084 -0.0956 0.3370 0.034 Uiso 1 1 calc R . .
C23 C 0.1548(5) 0.2658(5) 0.4590(3) 0.0265(12) Uani 1 1 d . . .
C24 C 0.1449(5) 0.0455(4) 0.4593(3) 0.0251(11) Uani 1 1 d . . .
C25 C -0.0132(5) 0.1596(4) 0.3736(3) 0.0231(11) Uani 1 1 d . . .
C26 C 0.1371(6) 0.6771(5) 0.4738(4) 0.0354(15) Uani 1 1 d . . .
N1 N 0.4769(4) -0.1793(4) 0.3747(3) 0.0359(12) Uani 1 1 d . . .
H1 H 0.4053 -0.1647 0.3613 0.043 Uiso 1 1 calc R . .
N2 N 0.3292(4) 0.1363(4) 0.3981(2) 0.0261(10) Uani 1 1 d . . .
N3 N 0.1613(4) 0.2678(4) 0.3006(2) 0.0237(10) Uani 1 1 d . . .
N4 N 0.1350(4) 0.0506(4) 0.2944(2) 0.0236(10) Uani 1 1 d . . .
O1 O 0.6449(4) -0.1048(4) 0.4226(3) 0.0526(13) Uani 1 1 d . . .
O2 O 0.1558(4) 0.3328(3) 0.5020(2) 0.0347(10) Uani 1 1 d . . .
O3 O 0.1403(4) -0.0185(4) 0.5025(2) 0.0371(10) Uani 1 1 d . . .
O4 O -0.1086(4) 0.1567(3) 0.3669(2) 0.0303(9) Uani 1 1 d . . .
O5 O 0.2814(4) 0.5826(4) 0.4147(3) 0.0481(12) Uani 1 1 d . . .
O6 O 0.2603(4) 0.7845(4) 0.4058(3) 0.0401(11) Uani 1 1 d . . .
O7 O 0.1170(5) 0.6637(4) 0.3401(3) 0.0497(13) Uani 1 1 d . . .
Br1 Br 0.34985(7) -0.28386(6) 0.23494(4) 0.04671(19) Uani 1 1 d . . .
Re1 Re 0.146582(18) 0.155264(16) 0.386300(11) 0.02122(9) Uani 1 1 d . . .
S1 S 0.20705(14) 0.67563(12) 0.40012(9) 0.0333(3) Uani 1 1 d . . .
F1 F 0.0867(4) 0.5798(3) 0.4808(2) 0.0531(11) Uani 1 1 d . . .
F2 F 0.2102(4) 0.6949(4) 0.5352(2) 0.0548(11) Uani 1 1 d . . .
F3 F 0.0586(3) 0.7552(3) 0.4674(3) 0.0524(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.369(10) . ?
C1 C2 1.397(9) . ?
C1 N1 1.424(7) . ?
C2 C3 1.369(9) . ?
C2 Br1 1.912(7) . ?
C3 C4 1.383(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.222(8) . ?
C7 N1 1.340(8) . ?
C7 C8 1.508(8) . ?
C8 C12 1.388(8) . ?
C8 C9 1.398(9) . ?
C9 C10 1.370(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(9) . ?
C10 H10 0.9500 . ?
C11 N2 1.347(7) . ?
C11 H11 0.9500 . ?
C12 N2 1.366(7) . ?
C12 H12 0.9500 . ?
C13 N3 1.348(7) . ?
C13 C14 1.397(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(8) . ?
C16 H16 0.9500 . ?
C17 N3 1.361(7) . ?
C17 C18 1.482(8) . ?
C18 N4 1.353(7) . ?
C18 C19 1.383(8) . ?
C19 C20 1.383(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(8) . ?
C21 H21 0.9500 . ?
C22 N4 1.355(7) . ?
C22 H22 0.9500 . ?
C23 O2 1.154(7) . ?
C23 Re1 1.920(6) . ?
C24 O3 1.144(7) . ?
C24 Re1 1.933(6) . ?
C25 O4 1.150(7) . ?
C25 Re1 1.923(6) . ?
C26 F3 1.331(7) . ?
C26 F1 1.341(7) . ?
C26 F2 1.352(8) . ?
C26 S1 1.800(7) . ?
N1 H1 0.8800 . ?
N2 Re1 2.214(5) . ?
N3 Re1 2.171(4) . ?
N4 Re1 2.156(4) . ?
O5 S1 1.434(5) . ?
O6 S1 1.456(4) . ?
O7 S1 1.437(5) . ?

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
C6 C1 C2 117.6(6) . . ?
C6 C1 N1 122.1(6) . . ?
C2 C1 N1 120.2(6) . . ?
C3 C2 C1 122.2(6) . . ?
C3 C2 Br1 117.9(5) . . ?
C1 C2 Br1 119.8(5) . . ?
C2 C3 C4 118.8(7) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 120.3(7) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.8(7) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 121.3(7) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O1 C7 N1 124.1(6) . . ?
O1 C7 C8 118.8(6) . . ?
N1 C7 C8 117.1(5) . . ?
C12 C8 C9 117.7(5) . . ?
C12 C8 C7 124.0(5) . . ?
C9 C8 C7 118.4(5) . . ?
C10 C9 C8 119.3(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 119.8(6) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N2 C11 C10 123.0(6) . . ?
N2 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
N2 C12 C8 123.3(5) . . ?
N2 C12 H12 118.4 . . ?
C8 C12 H12 118.4 . . ?
N3 C13 C14 122.0(5) . . ?
N3 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 119.1(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.0(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 119.4(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
N3 C17 C16 122.0(5) . . ?
N3 C17 C18 114.7(5) . . ?
C16 C17 C18 123.3(5) . . ?
N4 C18 C19 121.9(5) . . ?
N4 C18 C17 115.3(5) . . ?
C19 C18 C17 122.8(5) . . ?
C18 C19 C20 119.1(6) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 119.4(6) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C22 C21 C20 119.0(5) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
N4 C22 C21 122.5(6) . . ?
N4 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
O2 C23 Re1 177.6(5) . . ?
O3 C24 Re1 177.7(5) . . ?
O4 C25 Re1 176.6(4) . . ?
F3 C26 F1 106.6(5) . . ?
F3 C26 F2 108.0(5) . . ?
F1 C26 F2 106.7(6) . . ?
F3 C26 S1 112.5(5) . . ?
F1 C26 S1 111.9(4) . . ?
F2 C26 S1 111.0(5) . . ?
C7 N1 C1 124.7(5) . . ?
C7 N1 H1 117.7 . . ?
C1 N1 H1 117.7 . . ?
C11 N2 C12 116.8(5) . . ?
C11 N2 Re1 121.9(4) . . ?
C12 N2 Re1 121.0(4) . . ?
C13 N3 C17 118.5(5) . . ?
C13 N3 Re1 124.2(4) . . ?
C17 N3 Re1 117.2(3) . . ?
C18 N4 C22 118.1(5) . . ?
C18 N4 Re1 117.7(3) . . ?
C22 N4 Re1 124.1(4) . . ?
C23 Re1 C25 88.7(2) . . ?
C23 Re1 C24 87.0(2) . . ?
C25 Re1 C24 87.3(2) . . ?
C23 Re1 N4 171.9(2) . . ?
C25 Re1 N4 90.7(2) . . ?
C24 Re1 N4 101.1(2) . . ?
C23 Re1 N3 97.2(2) . . ?
C25 Re1 N3 97.1(2) . . ?
C24 Re1 N3 174.0(2) . . ?
N4 Re1 N3 74.87(17) . . ?
C23 Re1 N2 95.3(2) . . ?
C25 Re1 N2 175.42(19) . . ?
C24 Re1 N2 90.7(2) . . ?
N4 Re1 N2 85.59(17) . . ?
N3 Re1 N2 84.61(18) . . ?
O5 S1 O7 115.8(3) . . ?
O5 S1 O6 115.4(3) . . ?
O7 S1 O6 114.2(3) . . ?
O5 S1 C26 103.7(3) . . ?
O7 S1 C26 103.1(3) . . ?
O6 S1 C26 102.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.164
_refine_diff_density_min         -1.564
_refine_diff_density_rms         0.167
_database_code_depnum_ccdc_archive 'CCDC 893632'
#######################################################################
#
#                 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_slp1013c
#TrackingRef 'Re-oF_slp1013c.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 F N4 O4 Re, C F3 O3 S'
_chemical_formula_sum            'C26 H17 F4 N4 O7 Re S'
_chemical_formula_weight         791.70

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'
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                   8.5187(3)
_cell_length_b                   11.9891(4)
_cell_length_c                   13.4341(4)
_cell_angle_alpha                77.040(2)
_cell_angle_beta                 89.004(2)
_cell_angle_gamma                84.019(2)
_cell_volume                     1329.79(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    5403
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.47

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.977
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    4.731
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3311
_exptl_absorpt_correction_T_max  0.8711
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      210(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8828
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         27.47
_reflns_number_total             6007
_reflns_number_gt                5403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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)+(0.0552P)²+4.5153P] 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         6007
_refine_ls_number_parameters     452
_refine_ls_number_restraints     285
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4134(5) 0.7996(3) 0.6812(3) 0.0256(11) Uani 0.827(10) 1 d PD A 1
C1 C 0.2923(9) 0.6424(9) 0.7791(10) 0.0208(17) Uani 0.827(10) 1 d PDU A 1
C2 C 0.2812(12) 0.7525(10) 0.7165(7) 0.0188(15) Uani 0.827(10) 1 d PDU A 1
C3 C 0.1365(14) 0.8158(8) 0.6895(6) 0.0231(17) Uani 0.827(10) 1 d PDU A 1
H3 H 0.1308 0.8870 0.6422 0.028 Uiso 0.827(10) 1 calc PR A 1
C4 C 0.0010(11) 0.7729(7) 0.7331(6) 0.0215(17) Uani 0.827(10) 1 d PDU A 1
H4 H -0.0978 0.8143 0.7142 0.026 Uiso 0.827(10) 1 calc PR A 1
C5 C 0.0097(10) 0.6694(10) 0.8046(8) 0.029(2) Uani 0.827(10) 1 d PDU A 1
H5 H -0.0816 0.6440 0.8389 0.035 Uiso 0.827(10) 1 calc PR A 1
C6 C 0.1549(10) 0.6029(8) 0.8255(8) 0.0266(15) Uani 0.827(10) 1 d PDU A 1
H6 H 0.1600 0.5307 0.8712 0.032 Uiso 0.827(10) 1 calc PR A 1
F1A F 0.172(2) 0.5236(16) 0.9061(14) 0.032(5) Uani 0.173(10) 1 d PDU A 2
C1A C 0.299(3) 0.655(5) 0.781(5) 0.021(3) Uani 0.173(10) 1 d PDU A 2
C2A C 0.162(2) 0.615(3) 0.827(3) 0.025(3) Uani 0.173(10) 1 d PDU A 2
C3A C 0.013(3) 0.664(4) 0.790(3) 0.024(3) Uani 0.173(10) 1 d PDU A 2
H3A H -0.0774 0.6292 0.8151 0.029 Uiso 0.173(10) 1 calc PR A 2
C4A C 0.001(5) 0.764(4) 0.715(3) 0.025(3) Uani 0.173(10) 1 d PDU A 2
H4A H -0.0988 0.8004 0.6915 0.030 Uiso 0.173(10) 1 calc PR A 2
C5A C 0.136(6) 0.812(3) 0.673(3) 0.022(3) Uani 0.173(10) 1 d PDU A 2
H5A H 0.1270 0.8827 0.6253 0.027 Uiso 0.173(10) 1 calc PR A 2
C6A C 0.284(5) 0.754(4) 0.703(4) 0.021(3) Uani 0.173(10) 1 d PDU A 2
H6A H 0.3748 0.7820 0.6696 0.025 Uiso 0.173(10) 1 calc PR A 2
C7 C 0.5384(6) 0.5548(5) 0.7242(4) 0.0204(10) Uani 1 1 d . A 1
C8 C 0.6842(6) 0.4754(4) 0.7609(4) 0.0203(10) Uani 1 1 d . A 1
C9 C 0.7498(6) 0.4605(4) 0.8582(4) 0.0201(10) Uani 1 1 d . A 1
H9 H 0.7000 0.4973 0.9069 0.024 Uiso 1 1 calc R A 1
C10 C 0.8902(7) 0.3900(5) 0.8811(4) 0.0227(11) Uani 1 1 d . A 1
H10 H 0.9386 0.3799 0.9453 0.027 Uiso 1 1 calc R A 1
C11 C 0.9586(6) 0.3344(4) 0.8085(4) 0.0196(10) Uani 1 1 d . A 1
H11 H 1.0542 0.2874 0.8247 0.023 Uiso 1 1 calc R A 1
C12 C 0.7588(6) 0.4165(4) 0.6928(4) 0.0199(10) Uani 1 1 d . A 1
H12 H 0.7135 0.4267 0.6277 0.024 Uiso 1 1 calc R A 1
C13 C 0.6629(6) 0.2076(5) 0.5472(4) 0.0198(10) Uani 1 1 d . A 1
H13 H 0.6739 0.2723 0.4941 0.024 Uiso 1 1 calc R A 1
C14 C 0.5272(6) 0.1516(5) 0.5509(4) 0.0223(11) Uani 1 1 d . A 1
H14 H 0.4495 0.1765 0.4996 0.027 Uiso 1 1 calc R A 1
C15 C 0.5076(6) 0.0587(5) 0.6306(4) 0.0226(11) Uani 1 1 d . A 1
H15 H 0.4167 0.0197 0.6344 0.027 Uiso 1 1 calc R A 1
C16 C 0.6248(6) 0.0240(4) 0.7053(4) 0.0200(10) Uani 1 1 d . A 1
H16 H 0.6130 -0.0382 0.7607 0.024 Uiso 1 1 calc R A 1
C17 C 0.7590(6) 0.0815(4) 0.6976(4) 0.0172(10) Uani 1 1 d . A 1
C18 C 0.8924(6) 0.0460(4) 0.7702(4) 0.0179(10) Uani 1 1 d . A 1
C19 C 0.8906(7) -0.0415(4) 0.8573(4) 0.0209(11) Uani 1 1 d . A 1
H19 H 0.7973 -0.0759 0.8769 0.025 Uiso 1 1 calc R A 1
C20 C 1.0275(7) -0.0781(5) 0.9154(4) 0.0230(11) Uani 1 1 d . A 1
H20 H 1.0288 -0.1384 0.9738 0.028 Uiso 1 1 calc R A 1
C21 C 1.1620(7) -0.0238(5) 0.8852(4) 0.0250(11) Uani 1 1 d . A 1
H21 H 1.2569 -0.0483 0.9220 0.030 Uiso 1 1 calc R A 1
C22 C 1.1553(6) 0.0665(5) 0.8008(4) 0.0213(11) Uani 1 1 d . A 1
H22 H 1.2463 0.1041 0.7821 0.026 Uiso 1 1 calc R A 1
C23 C 0.9596(6) 0.3629(5) 0.4871(4) 0.0187(10) Uani 1 1 d . A 1
C24 C 1.2001(6) 0.3084(4) 0.6176(4) 0.0203(10) Uani 1 1 d . A 1
C25 C 1.1024(6) 0.1446(4) 0.5276(4) 0.0177(10) Uani 1 1 d . A 1
C26 C 0.5048(7) 0.2031(5) 0.9065(4) 0.0225(11) Uani 1 1 d . B 1
N1 N 0.4382(5) 0.5750(4) 0.7998(3) 0.0203(9) Uani 1 1 d . A 1
H1 H 0.4654 0.5451 0.8630 0.024 Uiso 1 1 calc R A 1
N2 N 0.8927(5) 0.3454(4) 0.7148(3) 0.0165(8) Uani 1 1 d . A 1
N3 N 0.7793(5) 0.1717(4) 0.6178(3) 0.0170(8) Uani 1 1 d . A 1
N4 N 1.0230(5) 0.1028(4) 0.7440(3) 0.0150(8) Uani 1 1 d . A 1
O1 O 0.5158(5) 0.5959(4) 0.6333(3) 0.0303(10) Uani 1 1 d . A 1
O2 O 0.9363(5) 0.4337(3) 0.4146(3) 0.0258(8) Uani 1 1 d . A 1
O3 O 1.3148(5) 0.3502(3) 0.6221(3) 0.0268(9) Uani 1 1 d . A 1
O4 O 1.1644(5) 0.0816(3) 0.4824(3) 0.0259(8) Uani 1 1 d . A 1
O5 O 0.4457(5) 0.3798(3) 0.9852(3) 0.0275(9) Uani 1 1 d . B 1
O6 O 0.2317(5) 0.2624(4) 0.9731(3) 0.0343(10) Uani 1 1 d . B 1
O7 O 0.4454(5) 0.1886(4) 1.0965(3) 0.0296(9) Uani 1 1 d . B 1
F2 F 0.4755(4) 0.0944(3) 0.9130(3) 0.0331(8) Uani 1 1 d . B 1
F3 F 0.6601(4) 0.2019(3) 0.9178(3) 0.0307(8) Uani 1 1 d . B 1
F4 F 0.4675(4) 0.2620(3) 0.8112(2) 0.0326(8) Uani 1 1 d . B 1
S1 S 0.39411(16) 0.26573(11) 1.00146(10) 0.0205(3) Uani 1 1 d . B 1
Re1 Re 1.00349(2) 0.243603(16) 0.609352(14) 0.01539(8) Uani 1 1 d . A 1


_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
F1 C2 1.344(10) . ?
C1 C2 1.392(10) . ?
C1 C6 1.392(11) . ?
C1 N1 1.407(9) . ?
C2 C3 1.387(10) . ?
C3 C4 1.380(11) . ?
C3 H3 0.9400 . ?
C4 C5 1.385(11) . ?
C4 H4 0.9400 . ?
C5 C6 1.397(11) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
F1A C2A 1.344(10) . ?
C1A C2A 1.392(11) . ?
C1A C6A 1.392(11) . ?
C2A C3A 1.388(10) . ?
C3A C4A 1.380(11) . ?
C3A H3A 0.9400 . ?
C4A C5A 1.385(11) . ?
C4A H4A 0.9400 . ?
C5A C6A 1.397(11) . ?
C5A H5A 0.9400 . ?
C6A H6A 0.9400 . ?
C7 O1 1.221(6) . ?
C7 N1 1.362(7) . ?
C7 C8 1.502(7) . ?
C8 C12 1.384(7) . ?
C8 C9 1.397(7) . ?
C9 C10 1.388(8) . ?
C9 H9 0.9400 . ?
C10 C11 1.387(7) . ?
C10 H10 0.9400 . ?
C11 N2 1.361(7) . ?
C11 H11 0.9400 . ?
C12 N2 1.346(7) . ?
C12 H12 0.9400 . ?
C13 N3 1.353(7) . ?
C13 C14 1.391(8) . ?
C13 H13 0.9400 . ?
C14 C15 1.383(8) . ?
C14 H14 0.9400 . ?
C15 C16 1.392(8) . ?
C15 H15 0.9400 . ?
C16 C17 1.385(7) . ?
C16 H16 0.9400 . ?
C17 N3 1.365(7) . ?
C17 C18 1.475(7) . ?
C18 N4 1.365(7) . ?
C18 C19 1.386(7) . ?
C19 C20 1.390(8) . ?
C19 H19 0.9400 . ?
C20 C21 1.387(8) . ?
C20 H20 0.9400 . ?
C21 C22 1.378(8) . ?
C21 H21 0.9400 . ?
C22 N4 1.349(7) . ?
C22 H22 0.9400 . ?
C23 O2 1.145(6) . ?
C23 Re1 1.934(5) . ?
C24 O3 1.152(7) . ?
C24 Re1 1.933(6) . ?
C25 O4 1.153(6) . ?
C25 Re1 1.915(5) . ?
C26 F3 1.332(6) . ?
C26 F2 1.335(6) . ?
C26 F4 1.341(6) . ?
C26 S1 1.823(6) . ?
N1 H1 0.8700 . ?
N2 Re1 2.208(4) . ?
N3 Re1 2.167(4) . ?
N4 Re1 2.175(4) . ?
O5 S1 1.449(4) . ?
O6 S1 1.448(4) . ?
O7 S1 1.443(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 C1 C6 117.9(5) . . ?
C2 C1 N1 121.5(7) . . ?
C6 C1 N1 120.6(7) . . ?
F1 C2 C3 118.7(8) . . ?
F1 C2 C1 119.7(7) . . ?
C3 C2 C1 121.7(7) . . ?
C4 C3 C2 119.1(7) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.6(7) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.7(7) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C2A C1A C6A 117.8(5) . . ?
F1A C2A C3A 118.6(8) . . ?
F1A C2A C1A 119.6(8) . . ?
C3A C2A C1A 121.6(7) . . ?
C4A C3A C2A 119.0(7) . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A H3A 120.5 . . ?
C3A C4A C5A 120.4(6) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C4A C5A C6A 119.6(7) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C1A C6A C5A 120.7(7) . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
O1 C7 N1 124.6(5) . . ?
O1 C7 C8 120.9(5) . . ?
N1 C7 C8 114.5(4) . . ?
C12 C8 C9 118.8(5) . . ?
C12 C8 C7 117.5(5) . . ?
C9 C8 C7 123.7(5) . . ?
C10 C9 C8 118.4(5) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 119.4(5) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N2 C11 C10 122.6(5) . . ?
N2 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
N2 C12 C8 123.5(5) . . ?
N2 C12 H12 118.2 . . ?
C8 C12 H12 118.2 . . ?
N3 C13 C14 121.9(5) . . ?
N3 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 119.4(5) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 118.8(5) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N3 C17 C16 121.3(5) . . ?
N3 C17 C18 115.5(5) . . ?
C16 C17 C18 123.1(5) . . ?
N4 C18 C19 121.2(5) . . ?
N4 C18 C17 115.2(4) . . ?
C19 C18 C17 123.5(5) . . ?
C18 C19 C20 119.7(5) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 118.6(5) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C20 119.4(5) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
N4 C22 C21 122.5(5) . . ?
N4 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
O2 C23 Re1 178.8(5) . . ?
O3 C24 Re1 178.0(5) . . ?
O4 C25 Re1 176.9(4) . . ?
F3 C26 F2 107.0(5) . . ?
F3 C26 F4 107.3(5) . . ?
F2 C26 F4 107.4(4) . . ?
F3 C26 S1 112.0(4) . . ?
F2 C26 S1 111.4(4) . . ?
F4 C26 S1 111.5(4) . . ?
C7 N1 C1 122.3(7) . . ?
C7 N1 H1 118.9 . . ?
C1 N1 H1 118.9 . . ?
C12 N2 C11 117.2(4) . . ?
C12 N2 Re1 123.4(3) . . ?
C11 N2 Re1 119.4(3) . . ?
C13 N3 C17 118.8(5) . . ?
C13 N3 Re1 124.1(4) . . ?
C17 N3 Re1 117.1(3) . . ?
C22 N4 C18 118.4(4) . . ?
C22 N4 Re1 124.7(4) . . ?
C18 N4 Re1 116.9(3) . . ?
O7 S1 O6 115.2(3) . . ?
O7 S1 O5 115.1(3) . . ?
O6 S1 O5 115.1(3) . . ?
O7 S1 C26 102.9(3) . . ?
O6 S1 C26 102.8(3) . . ?
O5 S1 C26 103.2(2) . . ?
C25 Re1 C24 90.3(2) . . ?
C25 Re1 C23 89.5(2) . . ?
C24 Re1 C23 86.6(2) . . ?
C25 Re1 N3 94.55(19) . . ?
C24 Re1 N3 173.63(18) . . ?
C23 Re1 N3 97.5(2) . . ?
C25 Re1 N4 90.76(18) . . ?
C24 Re1 N4 100.79(19) . . ?
C23 Re1 N4 172.62(19) . . ?
N3 Re1 N4 75.11(16) . . ?
C25 Re1 N2 175.16(17) . . ?
C24 Re1 N2 90.31(19) . . ?
C23 Re1 N2 95.29(18) . . ?
N3 Re1 N2 84.47(15) . . ?
N4 Re1 N2 84.41(15) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.693
_refine_diff_density_min         -2.490
_refine_diff_density_rms         0.209
_database_code_depnum_ccdc_archive 'CCDC 893633'
#######################################################################
#
#                 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_sjp1011
#TrackingRef 'Re-oI_sjp1011.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 I N4 O4 Re, C F3 O3 S'
_chemical_formula_sum            'C26 H17 F3 I N4 O7 Re S'
_chemical_formula_weight         899.60

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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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'

_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                   10.0523(2)
_cell_length_b                   11.6515(4)
_cell_length_c                   13.0988(4)
_cell_angle_alpha                69.7400(10)
_cell_angle_beta                 78.794(2)
_cell_angle_gamma                82.263(2)
_cell_volume                     1408.05(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5911
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.51

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    5.558
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3371
_exptl_absorpt_correction_T_max  0.6064
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9805
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         27.51
_reflns_number_total             6443
_reflns_number_gt                5911
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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)+(0.0252P)²+5.5756P] 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     SHELXL
_refine_ls_extinction_coef       0.0081(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6443
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7274(4) 0.8243(4) -0.0609(4) 0.0229(9) Uani 1 1 d . . .
C2 C 0.5890(5) 0.8399(4) -0.0698(4) 0.0239(9) Uani 1 1 d . . .
C3 C 0.5253(5) 0.9556(5) -0.1102(4) 0.0316(11) Uani 1 1 d . . .
H3 H 0.4314 0.9652 -0.1158 0.038 Uiso 1 1 calc R . .
C4 C 0.6003(6) 1.0575(5) -0.1424(4) 0.0337(12) Uani 1 1 d . . .
H4 H 0.5580 1.1374 -0.1714 0.040 Uiso 1 1 calc R . .
C5 C 0.7361(6) 1.0430(5) -0.1323(4) 0.0326(11) Uani 1 1 d . . .
H5 H 0.7867 1.1131 -0.1537 0.039 Uiso 1 1 calc R . .
C6 C 0.7992(5) 0.9273(5) -0.0914(4) 0.0292(10) Uani 1 1 d . . .
H6 H 0.8925 0.9185 -0.0841 0.035 Uiso 1 1 calc R . .
C7 C 0.8091(4) 0.6203(4) -0.0686(4) 0.0218(9) Uani 1 1 d . . .
C8 C 0.8330(4) 0.4880(4) -0.0006(4) 0.0190(9) Uani 1 1 d . . .
C9 C 0.8759(4) 0.4016(5) -0.0540(4) 0.0239(9) Uani 1 1 d . . .
H9 H 0.8963 0.4268 -0.1321 0.029 Uiso 1 1 calc R . .
C10 C 0.8884(4) 0.2783(4) 0.0082(4) 0.0224(9) Uani 1 1 d . . .
H10 H 0.9170 0.2180 -0.0267 0.027 Uiso 1 1 calc R . .
C11 C 0.8586(4) 0.2445(4) 0.1216(4) 0.0213(9) Uani 1 1 d . . .
H11 H 0.8663 0.1598 0.1637 0.026 Uiso 1 1 calc R . .
C12 C 0.8070(4) 0.4461(4) 0.1143(4) 0.0185(8) Uani 1 1 d . . .
H12 H 0.7796 0.5048 0.1512 0.022 Uiso 1 1 calc R . .
C13 C 0.6195(5) 0.5199(4) 0.3451(4) 0.0225(9) Uani 1 1 d . . .
H13 H 0.7028 0.5440 0.3524 0.027 Uiso 1 1 calc R . .
C14 C 0.5084(5) 0.6045(5) 0.3347(5) 0.0309(11) Uani 1 1 d . . .
H14 H 0.5148 0.6844 0.3364 0.037 Uiso 1 1 calc R . .
C15 C 0.3865(5) 0.5702(5) 0.3217(5) 0.0322(11) Uani 1 1 d . . .
H15 H 0.3093 0.6273 0.3117 0.039 Uiso 1 1 calc R . .
C16 C 0.3804(5) 0.4524(4) 0.3237(4) 0.0274(10) Uani 1 1 d . . .
H16 H 0.2980 0.4270 0.3161 0.033 Uiso 1 1 calc R . .
C17 C 0.4948(4) 0.3704(4) 0.3369(4) 0.0195(9) Uani 1 1 d . . .
C18 C 0.4950(4) 0.2411(4) 0.3441(4) 0.0185(8) Uani 1 1 d . . .
C19 C 0.3789(5) 0.1895(4) 0.3449(4) 0.0241(9) Uani 1 1 d . . .
H19 H 0.2951 0.2381 0.3382 0.029 Uiso 1 1 calc R . .
C20 C 0.3849(5) 0.0671(4) 0.3554(4) 0.0244(9) Uani 1 1 d . . .
H20 H 0.3055 0.0301 0.3569 0.029 Uiso 1 1 calc R . .
C21 C 0.5080(5) -0.0006(5) 0.3635(4) 0.0254(10) Uani 1 1 d . . .
H21 H 0.5150 -0.0850 0.3704 0.031 Uiso 1 1 calc R . .
C22 C 0.6221(5) 0.0563(4) 0.3616(4) 0.0214(9) Uani 1 1 d . . .
H22 H 0.7070 0.0093 0.3664 0.026 Uiso 1 1 calc R . .
C23 C 0.9272(4) 0.3688(4) 0.3561(4) 0.0213(9) Uani 1 1 d . . .
C24 C 0.9325(5) 0.1401(4) 0.3652(4) 0.0238(9) Uani 1 1 d . . .
C25 C 0.7576(4) 0.2203(4) 0.5159(4) 0.0208(9) Uani 1 1 d . . .
C26 C 0.9127(6) 0.7362(6) 0.3582(6) 0.0433(15) Uani 1 1 d . . .
N1 N 0.7888(4) 0.7040(4) -0.0150(3) 0.0231(8) Uani 1 1 d . . .
H1 H 0.8144 0.6833 0.0500 0.028 Uiso 1 1 calc R . .
N2 N 0.8189(3) 0.3271(4) 0.1754(3) 0.0192(7) Uani 1 1 d . . .
N3 N 0.6152(4) 0.4049(3) 0.3453(3) 0.0183(7) Uani 1 1 d . . .
N4 N 0.6170(3) 0.1751(3) 0.3531(3) 0.0173(7) Uani 1 1 d . . .
O1 O 0.8010(4) 0.6476(3) -0.1664(3) 0.0329(8) Uani 1 1 d . . .
O2 O 1.0109(3) 0.4263(3) 0.3571(3) 0.0314(8) Uani 1 1 d . . .
O3 O 1.0202(4) 0.0660(3) 0.3697(3) 0.0361(9) Uani 1 1 d . . .
O4 O 0.7395(4) 0.1919(3) 0.6098(3) 0.0281(7) Uani 1 1 d . . .
O5 O 0.8609(4) 0.6911(3) 0.1933(3) 0.0304(8) Uani 1 1 d . . .
O6 O 0.7073(4) 0.8340(4) 0.2637(4) 0.0485(11) Uani 1 1 d . . .
O7 O 0.9303(5) 0.8935(4) 0.1630(4) 0.0547(12) Uani 1 1 d . . .
I1 I 0.47397(3) 0.68604(4) -0.01571(3) 0.03687(10) Uani 1 1 d . . .
Re1 Re 0.787933(16) 0.269098(15) 0.357816(14) 0.01712(7) Uani 1 1 d . . .
S1 S 0.84575(12) 0.79688(11) 0.23014(10) 0.0269(3) Uani 1 1 d . . .
F1 F 1.0415(4) 0.6914(4) 0.3442(4) 0.0605(11) Uani 1 1 d . . .
F2 F 0.8424(4) 0.6439(4) 0.4313(3) 0.0542(10) Uani 1 1 d . . .
F3 F 0.9089(5) 0.8221(4) 0.4053(3) 0.0614(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.382(7) . ?
C1 C2 1.400(6) . ?
C1 N1 1.427(6) . ?
C2 C3 1.383(7) . ?
C2 I1 2.101(5) . ?
C3 C4 1.388(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.224(6) . ?
C7 N1 1.361(6) . ?
C7 C8 1.503(6) . ?
C8 C9 1.393(6) . ?
C8 C12 1.395(6) . ?
C9 C10 1.387(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(6) . ?
C10 H10 0.9500 . ?
C11 N2 1.357(6) . ?
C11 H11 0.9500 . ?
C12 N2 1.342(6) . ?
C12 H12 0.9500 . ?
C13 N3 1.346(6) . ?
C13 C14 1.381(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(6) . ?
C16 H16 0.9500 . ?
C17 N3 1.362(5) . ?
C17 C18 1.476(6) . ?
C18 N4 1.359(5) . ?
C18 C19 1.381(6) . ?
C19 C20 1.379(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.377(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(6) . ?
C21 H21 0.9500 . ?
C22 N4 1.344(6) . ?
C22 H22 0.9500 . ?
C23 O2 1.148(6) . ?
C23 Re1 1.928(5) . ?
C24 O3 1.144(6) . ?
C24 Re1 1.935(5) . ?
C25 O4 1.142(6) . ?
C25 Re1 1.920(5) . ?
C26 F1 1.332(7) . ?
C26 F3 1.339(6) . ?
C26 F2 1.342(8) . ?
C26 S1 1.804(6) . ?
N1 H1 0.8800 . ?
N2 Re1 2.216(4) . ?
N3 Re1 2.177(4) . ?
N4 Re1 2.180(3) . ?
O5 S1 1.452(4) . ?
O6 S1 1.431(4) . ?
O7 S1 1.430(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
C6 C1 C2 118.7(4) . . ?
C6 C1 N1 121.6(4) . . ?
C2 C1 N1 119.7(4) . . ?
C3 C2 C1 121.1(5) . . ?
C3 C2 I1 119.2(4) . . ?
C1 C2 I1 119.7(4) . . ?
C2 C3 C4 119.2(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.5(5) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 123.0(4) . . ?
O1 C7 C8 119.8(4) . . ?
N1 C7 C8 117.0(4) . . ?
C9 C8 C12 118.0(4) . . ?
C9 C8 C7 119.0(4) . . ?
C12 C8 C7 122.9(4) . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N2 C11 C10 122.7(4) . . ?
N2 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
N2 C12 C8 123.3(4) . . ?
N2 C12 H12 118.4 . . ?
C8 C12 H12 118.4 . . ?
N3 C13 C14 123.0(4) . . ?
N3 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C13 C14 C15 118.7(5) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 118.7(4) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
N3 C17 C16 121.4(4) . . ?
N3 C17 C18 115.3(4) . . ?
C16 C17 C18 123.3(4) . . ?
N4 C18 C19 122.1(4) . . ?
N4 C18 C17 115.4(4) . . ?
C19 C18 C17 122.4(4) . . ?
C20 C19 C18 119.7(4) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 118.8(4) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 119.1(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N4 C22 C21 122.6(4) . . ?
N4 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
O2 C23 Re1 178.6(4) . . ?
O3 C24 Re1 178.2(4) . . ?
O4 C25 Re1 179.6(4) . . ?
F1 C26 F3 107.2(5) . . ?
F1 C26 F2 106.4(5) . . ?
F3 C26 F2 107.4(6) . . ?
F1 C26 S1 112.1(5) . . ?
F3 C26 S1 111.7(4) . . ?
F2 C26 S1 111.7(4) . . ?
C7 N1 C1 121.9(4) . . ?
C7 N1 H1 119.0 . . ?
C1 N1 H1 119.0 . . ?
C12 N2 C11 117.7(4) . . ?
C12 N2 Re1 121.0(3) . . ?
C11 N2 Re1 121.2(3) . . ?
C13 N3 C17 118.1(4) . . ?
C13 N3 Re1 124.6(3) . . ?
C17 N3 Re1 117.3(3) . . ?
C22 N4 C18 117.7(4) . . ?
C22 N4 Re1 125.0(3) . . ?
C18 N4 Re1 117.2(3) . . ?
C25 Re1 C23 88.25(18) . . ?
C25 Re1 C24 89.31(19) . . ?
C23 Re1 C24 85.37(19) . . ?
C25 Re1 N3 92.24(16) . . ?
C23 Re1 N3 99.29(16) . . ?
C24 Re1 N3 175.13(16) . . ?
C25 Re1 N4 93.63(15) . . ?
C23 Re1 N4 173.73(16) . . ?
C24 Re1 N4 100.62(16) . . ?
N3 Re1 N4 74.67(13) . . ?
C25 Re1 N2 178.87(16) . . ?
C23 Re1 N2 92.25(16) . . ?
C24 Re1 N2 91.74(17) . . ?
N3 Re1 N2 86.68(13) . . ?
N4 Re1 N2 85.76(13) . . ?
O7 S1 O6 115.9(3) . . ?
O7 S1 O5 114.8(3) . . ?
O6 S1 O5 113.6(2) . . ?
O7 S1 C26 104.5(3) . . ?
O6 S1 C26 103.1(3) . . ?
O5 S1 C26 102.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.135
_refine_diff_density_min         -1.365
_refine_diff_density_rms         0.153
_database_code_depnum_ccdc_archive 'CCDC 893634'
#######################################################################
#
#                 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
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#  data retrieval see:
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data_bmk1102c
#TrackingRef 'Re-pBr_bmk1102c.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 Br N4 O4 Re, C F3 O3 S'
_chemical_formula_sum            'C26 H17 Br F3 N4 O7 Re S'
_chemical_formula_weight         852.61

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   20.4610(3)
_cell_length_b                   8.99680(10)
_cell_length_c                   31.6923(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.2680(10)
_cell_angle_gamma                90.00
_cell_volume                     5654.07(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11854
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.003
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3280
_exptl_absorpt_coefficient_mu    5.858
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3589
_exptl_absorpt_correction_T_max  0.5399
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25612
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         27.97
_reflns_number_total             13407
_reflns_number_gt                11854
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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)+(0.0307P)²+17.2364P] 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         13407
_refine_ls_number_parameters     775
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.004
_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 0.8105(3) 1.2315(5) 0.48779(16) 0.0246(11) Uani 1 1 d . . .
C2 C 0.8793(3) 1.2211(6) 0.50584(18) 0.0312(12) Uani 1 1 d . . .
H2 H 0.8964 1.1610 0.5308 0.037 Uiso 1 1 calc R . .
C3 C 0.9230(3) 1.3004(7) 0.48679(19) 0.0373(14) Uani 1 1 d . . .
H3 H 0.9704 1.2925 0.4979 0.045 Uiso 1 1 calc R . .
C4 C 0.8962(3) 1.3913(7) 0.45117(19) 0.0360(14) Uani 1 1 d . . .
C5 C 0.8288(3) 1.4026(6) 0.43359(19) 0.0343(13) Uani 1 1 d . . .
H5 H 0.8118 1.4643 0.4090 0.041 Uiso 1 1 calc R . .
C6 C 0.7853(3) 1.3224(6) 0.45216(17) 0.0288(12) Uani 1 1 d . . .
H6 H 0.7379 1.3296 0.4404 0.035 Uiso 1 1 calc R . .
C7 C 0.7695(3) 1.0912(6) 0.54420(16) 0.0260(11) Uani 1 1 d . . .
C8 C 0.7089(3) 1.0081(5) 0.55003(16) 0.0218(10) Uani 1 1 d . . .
C9 C 0.6621(3) 0.9379(5) 0.51680(16) 0.0243(10) Uani 1 1 d . . .
H9 H 0.6679 0.9382 0.4880 0.029 Uiso 1 1 calc R . .
C10 C 0.6071(3) 0.8675(6) 0.52594(17) 0.0291(11) Uani 1 1 d . . .
H10 H 0.5753 0.8173 0.5036 0.035 Uiso 1 1 calc R . .
C11 C 0.5989(3) 0.8707(6) 0.56818(17) 0.0284(11) Uani 1 1 d . . .
H11 H 0.5604 0.8245 0.5742 0.034 Uiso 1 1 calc R . .
C12 C 0.6984(3) 1.0014(5) 0.59145(16) 0.0230(10) Uani 1 1 d . . .
H12 H 0.7314 1.0441 0.6147 0.028 Uiso 1 1 calc R . .
C13 C 0.7208(3) 1.2316(7) 0.67880(18) 0.0373(14) Uani 1 1 d . . .
H13 H 0.7540 1.1690 0.6964 0.045 Uiso 1 1 calc R . .
C14 C 0.7392(3) 1.3737(8) 0.66983(19) 0.0414(15) Uani 1 1 d . . .
H14 H 0.7840 1.4078 0.6810 0.050 Uiso 1 1 calc R . .
C15 C 0.6911(3) 1.4654(7) 0.6444(2) 0.0396(15) Uani 1 1 d . . .
H15 H 0.7025 1.5629 0.6371 0.047 Uiso 1 1 calc R . .
C16 C 0.6264(3) 1.4128(6) 0.62965(17) 0.0312(12) Uani 1 1 d . . .
H16 H 0.5925 1.4742 0.6122 0.037 Uiso 1 1 calc R . .
C17 C 0.6106(3) 1.2705(6) 0.64030(15) 0.0248(11) Uani 1 1 d . . .
C18 C 0.5412(3) 1.2100(5) 0.62761(15) 0.0230(10) Uani 1 1 d . . .
C19 C 0.4851(3) 1.2962(6) 0.60996(17) 0.0274(11) Uani 1 1 d . . .
H19 H 0.4900 1.3981 0.6035 0.033 Uiso 1 1 calc R . .
C20 C 0.4222(3) 1.2328(6) 0.60187(17) 0.0298(12) Uani 1 1 d . . .
H20 H 0.3832 1.2910 0.5901 0.036 Uiso 1 1 calc R . .
C21 C 0.4159(3) 1.0843(6) 0.61086(17) 0.0288(11) Uani 1 1 d . . .
H21 H 0.3728 1.0385 0.6055 0.035 Uiso 1 1 calc R . .
C22 C 0.4740(3) 1.0039(6) 0.62789(17) 0.0263(11) Uani 1 1 d . . .
H22 H 0.4698 0.9010 0.6334 0.032 Uiso 1 1 calc R . .
C23 C 0.7137(3) 0.8511(6) 0.69235(17) 0.0280(11) Uani 1 1 d . . .
C24 C 0.5828(3) 0.7585(6) 0.66510(16) 0.0280(11) Uani 1 1 d . . .
C25 C 0.6180(3) 0.9601(7) 0.72570(18) 0.0329(13) Uani 1 1 d . . .
C26 C 1.1559(2) 1.1528(5) 0.53914(15) 0.0212(10) Uani 1 1 d . . .
C27 C 1.1116(3) 1.1594(6) 0.49814(16) 0.0289(11) Uani 1 1 d . . .
H27 H 1.0695 1.1091 0.4926 0.035 Uiso 1 1 calc R . .
C28 C 1.1295(3) 1.2401(6) 0.46551(17) 0.0296(12) Uani 1 1 d . . .
H28 H 1.0997 1.2456 0.4374 0.036 Uiso 1 1 calc R . .
C29 C 1.1909(3) 1.3125(6) 0.47396(16) 0.0266(11) Uani 1 1 d . . .
C30 C 1.2352(3) 1.3074(6) 0.51449(17) 0.0273(11) Uani 1 1 d . . .
H30 H 1.2772 1.3583 0.5200 0.033 Uiso 1 1 calc R . .
C31 C 1.2173(3) 1.2267(6) 0.54690(16) 0.0245(10) Uani 1 1 d . . .
H31 H 1.2474 1.2215 0.5750 0.029 Uiso 1 1 calc R . .
C32 C 1.0837(3) 1.0250(5) 0.58054(16) 0.0223(10) Uani 1 1 d . . .
C33 C 1.0898(3) 0.9497(5) 0.62367(15) 0.0211(10) Uani 1 1 d . . .
C34 C 1.1420(3) 0.8553(6) 0.64278(17) 0.0258(11) Uani 1 1 d . . .
H34 H 1.1755 0.8293 0.6280 0.031 Uiso 1 1 calc R . .
C35 C 1.1444(3) 0.7994(6) 0.68394(17) 0.0292(11) Uani 1 1 d . . .
H35 H 1.1794 0.7331 0.6976 0.035 Uiso 1 1 calc R . .
C36 C 1.0953(3) 0.8412(5) 0.70486(16) 0.0246(10) Uani 1 1 d . . .
H36 H 1.0981 0.8048 0.7334 0.030 Uiso 1 1 calc R . .
C37 C 1.0406(3) 0.9807(5) 0.64597(16) 0.0218(10) Uani 1 1 d . . .
H37 H 1.0031 1.0398 0.6319 0.026 Uiso 1 1 calc R . .
C38 C 1.0785(3) 1.0366(6) 0.80442(17) 0.0305(12) Uani 1 1 d . . .
H38 H 1.0696 0.9364 0.8106 0.037 Uiso 1 1 calc R . .
C39 C 1.1280(3) 1.1130(7) 0.83423(19) 0.0353(13) Uani 1 1 d . . .
H39 H 1.1525 1.0661 0.8602 0.042 Uiso 1 1 calc R . .
C40 C 1.1406(3) 1.2567(7) 0.8255(2) 0.0420(15) Uani 1 1 d . . .
H40 H 1.1740 1.3120 0.8455 0.050 Uiso 1 1 calc R . .
C41 C 1.1044(3) 1.3219(6) 0.7873(2) 0.0365(14) Uani 1 1 d . . .
H41 H 1.1129 1.4222 0.7808 0.044 Uiso 1 1 calc R . .
C42 C 1.0554(3) 1.2391(5) 0.75830(17) 0.0243(11) Uani 1 1 d . . .
C43 C 1.0147(3) 1.2992(6) 0.71691(17) 0.0258(11) Uani 1 1 d . . .
C44 C 1.0231(3) 1.4439(6) 0.7030(2) 0.0379(14) Uani 1 1 d . . .
H44 H 1.0566 1.5072 0.7200 0.045 Uiso 1 1 calc R . .
C45 C 0.9823(4) 1.4931(7) 0.6644(2) 0.0490(19) Uani 1 1 d . . .
H45 H 0.9870 1.5911 0.6544 0.059 Uiso 1 1 calc R . .
C46 C 0.9346(4) 1.3989(8) 0.6405(2) 0.0493(19) Uani 1 1 d . . .
H46 H 0.9063 1.4311 0.6136 0.059 Uiso 1 1 calc R . .
C47 C 0.9277(3) 1.2554(8) 0.65569(19) 0.0399(15) Uani 1 1 d . . .
H47 H 0.8942 1.1912 0.6391 0.048 Uiso 1 1 calc R . .
C48 C 0.8978(3) 0.8933(7) 0.67289(18) 0.0358(13) Uani 1 1 d . . .
C49 C 0.9738(3) 0.8014(6) 0.75142(17) 0.0336(13) Uani 1 1 d . . .
C50 C 0.8902(3) 1.0346(6) 0.74495(17) 0.0302(12) Uani 1 1 d . . .
C51 C 0.5923(3) 0.3576(7) 0.50905(18) 0.0347(13) Uani 1 1 d . . .
C52 C 0.2156(4) 0.2465(7) 0.6974(2) 0.0459(16) Uani 1 1 d . . .
N1 N 0.7625(2) 1.1479(5) 0.50371(14) 0.0254(9) Uani 1 1 d . . .
H1 H 0.7236 1.1312 0.4850 0.030 Uiso 1 1 calc R . .
N2 N 0.6440(2) 0.9377(5) 0.60076(13) 0.0241(9) Uani 1 1 d . . .
N3 N 0.6585(2) 1.1784(5) 0.66375(13) 0.0268(9) Uani 1 1 d . . .
N4 N 0.5358(2) 1.0637(4) 0.63704(12) 0.0204(8) Uani 1 1 d . . .
N5 N 1.1437(2) 1.0687(5) 0.57398(13) 0.0242(9) Uani 1 1 d . . .
H5A H 1.1797 1.0411 0.5940 0.029 Uiso 1 1 calc R . .
N6 N 1.0437(2) 0.9312(4) 0.68632(13) 0.0220(9) Uani 1 1 d . . .
N7 N 1.0428(2) 1.0974(4) 0.76727(13) 0.0209(8) Uani 1 1 d . . .
N8 N 0.9675(2) 1.2065(5) 0.69333(13) 0.0273(10) Uani 1 1 d . . .
O1 O 0.8192(2) 1.1075(5) 0.57467(12) 0.0365(9) Uani 1 1 d . . .
O2 O 0.7632(2) 0.7905(5) 0.70719(13) 0.0388(10) Uani 1 1 d . . .
O3 O 0.5519(2) 0.6524(4) 0.66544(12) 0.0356(9) Uani 1 1 d . . .
O4 O 0.6141(2) 0.9591(6) 0.76156(13) 0.0495(12) Uani 1 1 d . . .
O5 O 1.02830(19) 1.0496(5) 0.55565(12) 0.0332(9) Uani 1 1 d . . .
O6 O 0.8590(2) 0.8379(6) 0.64503(14) 0.0566(14) Uani 1 1 d . . .
O7 O 0.9826(3) 0.6959(5) 0.77305(14) 0.0514(13) Uani 1 1 d . . .
O8 O 0.8438(2) 1.0620(5) 0.75780(13) 0.0429(11) Uani 1 1 d . . .
O9 O 0.52064(19) 0.3498(4) 0.42951(12) 0.0336(9) Uani 1 1 d . . .
O10 O 0.6228(2) 0.1993(4) 0.44907(12) 0.0311(8) Uani 1 1 d . . .
O11 O 0.6312(2) 0.4676(4) 0.44457(13) 0.0340(9) Uani 1 1 d . . .
O12 O 0.26154(19) 0.0594(4) 0.65008(12) 0.0295(8) Uani 1 1 d . . .
O13 O 0.2979(3) 0.3152(5) 0.65078(15) 0.0565(13) Uani 1 1 d . . .
O14 O 0.3392(2) 0.1600(5) 0.71408(15) 0.0557(13) Uani 1 1 d . . .
F1 F 0.5527(2) 0.2567(5) 0.52060(13) 0.0597(11) Uani 1 1 d . . .
F2 F 0.5720(2) 0.4911(5) 0.51854(13) 0.0606(12) Uani 1 1 d . . .
F3 F 0.65376(18) 0.3359(4) 0.53437(10) 0.0401(8) Uani 1 1 d . . .
F4 F 0.2005(3) 0.1429(6) 0.72277(17) 0.0861(17) Uani 1 1 d . . .
F5 F 0.1619(2) 0.2743(6) 0.66568(17) 0.0821(16) Uani 1 1 d . . .
F6 F 0.2311(2) 0.3699(4) 0.72137(14) 0.0628(12) Uani 1 1 d . . .
S1 S 0.59141(7) 0.34239(13) 0.45187(4) 0.0248(3) Uani 1 1 d . . .
S2 S 0.28693(7) 0.18962(15) 0.67587(4) 0.0290(3) Uani 1 1 d . . .
Br1 Br 0.95650(4) 1.49961(9) 0.42538(3) 0.0611(2) Uani 1 1 d . . .
Br2 Br 1.21715(3) 1.42303(8) 0.42984(2) 0.04485(16) Uani 1 1 d . . .
Re1 Re 0.627898(10) 0.94702(2) 0.667606(6) 0.02343(6) Uani 1 1 d . . .
Re2 Re 0.963667(11) 0.98372(2) 0.719787(6) 0.02277(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.386(7) . ?
C1 C6 1.387(7) . ?
C1 N1 1.425(6) . ?
C2 C3 1.392(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.358(9) . ?
C4 Br1 1.908(5) . ?
C5 C6 1.385(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.226(7) . ?
C7 N1 1.355(6) . ?
C7 C8 1.498(7) . ?
C8 C12 1.383(7) . ?
C8 C9 1.388(7) . ?
C9 C10 1.383(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(7) . ?
C10 H10 0.9500 . ?
C11 N2 1.346(7) . ?
C11 H11 0.9500 . ?
C12 N2 1.348(6) . ?
C12 H12 0.9500 . ?
C13 N3 1.336(7) . ?
C13 C14 1.382(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(7) . ?
C16 H16 0.9500 . ?
C17 N3 1.357(7) . ?
C17 C18 1.481(7) . ?
C18 N4 1.360(6) . ?
C18 C19 1.384(7) . ?
C19 C20 1.372(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(7) . ?
C21 H21 0.9500 . ?
C22 N4 1.338(7) . ?
C22 H22 0.9500 . ?
C23 O2 1.145(6) . ?
C23 Re1 1.940(5) . ?
C24 O3 1.147(7) . ?
C24 Re1 1.923(6) . ?
C25 O4 1.158(7) . ?
C25 Re1 1.905(5) . ?
C26 C31 1.388(7) . ?
C26 C27 1.390(7) . ?
C26 N5 1.410(6) . ?
C27 C28 1.385(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.381(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.379(7) . ?
C29 Br2 1.898(5) . ?
C30 C31 1.380(7) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 O5 1.231(6) . ?
C32 N5 1.353(6) . ?
C32 C33 1.503(7) . ?
C33 C34 1.382(7) . ?
C33 C37 1.393(7) . ?
C34 C35 1.388(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(7) . ?
C35 H35 0.9500 . ?
C36 N6 1.345(7) . ?
C36 H36 0.9500 . ?
C37 N6 1.341(6) . ?
C37 H37 0.9500 . ?
C38 N7 1.340(7) . ?
C38 C39 1.385(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.360(9) . ?
C39 H39 0.9500 . ?
C40 C41 1.386(9) . ?
C40 H40 0.9500 . ?
C41 C42 1.396(7) . ?
C41 H41 0.9500 . ?
C42 N7 1.346(6) . ?
C42 C43 1.472(7) . ?
C43 N8 1.354(7) . ?
C43 C44 1.398(7) . ?
C44 C45 1.374(10) . ?
C44 H44 0.9500 . ?
C45 C46 1.370(11) . ?
C45 H45 0.9500 . ?
C46 C47 1.397(9) . ?
C46 H46 0.9500 . ?
C47 N8 1.342(7) . ?
C47 H47 0.9500 . ?
C48 O6 1.145(7) . ?
C48 Re2 1.924(6) . ?
C49 O7 1.159(7) . ?
C49 Re2 1.907(6) . ?
C50 O8 1.148(7) . ?
C50 Re2 1.923(6) . ?
C51 F1 1.327(7) . ?
C51 F3 1.329(7) . ?
C51 F2 1.330(7) . ?
C51 S1 1.813(6) . ?
C52 F4 1.317(8) . ?
C52 F5 1.317(8) . ?
C52 F6 1.338(7) . ?
C52 S2 1.830(7) . ?
N1 H1 0.8800 . ?
N2 Re1 2.224(4) . ?
N3 Re1 2.186(5) . ?
N4 Re1 2.167(4) . ?
N5 H5A 0.8800 . ?
N6 Re2 2.211(4) . ?
N7 Re2 2.175(4) . ?
N8 Re2 2.181(4) . ?
O9 S1 1.448(4) . ?
O10 S1 1.451(4) . ?
O11 S1 1.442(4) . ?
O12 S2 1.450(4) . ?
O13 S2 1.431(5) . ?
O14 S2 1.430(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 C1 C6 120.8(5) . . ?
C2 C1 N1 122.5(5) . . ?
C6 C1 N1 116.6(5) . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.0(6) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 122.3(5) . . ?
C5 C4 Br1 119.0(5) . . ?
C3 C4 Br1 118.7(5) . . ?
C4 C5 C6 118.7(6) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 120.3(6) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 N1 125.0(5) . . ?
O1 C7 C8 120.9(4) . . ?
N1 C7 C8 114.0(5) . . ?
C12 C8 C9 117.5(5) . . ?
C12 C8 C7 117.8(5) . . ?
C9 C8 C7 124.8(4) . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.3(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
N2 C11 C10 121.7(5) . . ?
N2 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
N2 C12 C8 123.8(5) . . ?
N2 C12 H12 118.1 . . ?
C8 C12 H12 118.1 . . ?
N3 C13 C14 122.8(6) . . ?
N3 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C15 C14 C13 118.8(6) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C16 C15 C14 118.7(6) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 120.0(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
N3 C17 C16 121.2(5) . . ?
N3 C17 C18 116.0(5) . . ?
C16 C17 C18 122.7(5) . . ?
N4 C18 C19 121.8(5) . . ?
N4 C18 C17 114.9(4) . . ?
C19 C18 C17 123.2(5) . . ?
C20 C19 C18 119.3(5) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 119.7(5) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 118.2(5) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
N4 C22 C21 123.3(5) . . ?
N4 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
O2 C23 Re1 177.8(5) . . ?
O3 C24 Re1 173.7(5) . . ?
O4 C25 Re1 175.4(5) . . ?
C31 C26 C27 119.9(4) . . ?
C31 C26 N5 116.4(4) . . ?
C27 C26 N5 123.7(5) . . ?
C28 C27 C26 119.3(5) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C29 C28 C27 119.9(5) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C30 C29 C28 121.5(5) . . ?
C30 C29 Br2 117.6(4) . . ?
C28 C29 Br2 120.9(4) . . ?
C29 C30 C31 118.4(5) . . ?
C29 C30 H30 120.8 . . ?
C31 C30 H30 120.8 . . ?
C30 C31 C26 121.0(5) . . ?
C30 C31 H31 119.5 . . ?
C26 C31 H31 119.5 . . ?
O5 C32 N5 125.2(5) . . ?
O5 C32 C33 121.3(4) . . ?
N5 C32 C33 113.3(4) . . ?
C34 C33 C37 118.5(5) . . ?
C34 C33 C32 123.9(4) . . ?
C37 C33 C32 117.6(5) . . ?
C33 C34 C35 118.7(5) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
C36 C35 C34 119.3(5) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
N6 C36 C35 122.5(5) . . ?
N6 C36 H36 118.7 . . ?
C35 C36 H36 118.7 . . ?
N6 C37 C33 123.2(5) . . ?
N6 C37 H37 118.4 . . ?
C33 C37 H37 118.4 . . ?
N7 C38 C39 123.1(5) . . ?
N7 C38 H38 118.5 . . ?
C39 C38 H38 118.5 . . ?
C40 C39 C38 118.5(6) . . ?
C40 C39 H39 120.8 . . ?
C38 C39 H39 120.8 . . ?
C39 C40 C41 119.6(6) . . ?
C39 C40 H40 120.2 . . ?
C41 C40 H40 120.2 . . ?
C40 C41 C42 119.4(5) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
N7 C42 C41 120.7(5) . . ?
N7 C42 C43 116.1(5) . . ?
C41 C42 C43 123.1(5) . . ?
N8 C43 C44 121.7(5) . . ?
N8 C43 C42 115.8(4) . . ?
C44 C43 C42 122.4(5) . . ?
C45 C44 C43 119.1(6) . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C46 C45 C44 119.1(6) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C45 C46 C47 120.0(6) . . ?
C45 C46 H46 120.0 . . ?
C47 C46 H46 120.0 . . ?
N8 C47 C46 121.2(7) . . ?
N8 C47 H47 119.4 . . ?
C46 C47 H47 119.4 . . ?
O6 C48 Re2 179.2(6) . . ?
O7 C49 Re2 175.3(5) . . ?
O8 C50 Re2 176.0(5) . . ?
F1 C51 F3 106.5(5) . . ?
F1 C51 F2 108.0(5) . . ?
F3 C51 F2 107.3(5) . . ?
F1 C51 S1 111.6(4) . . ?
F3 C51 S1 111.6(4) . . ?
F2 C51 S1 111.6(4) . . ?
F4 C52 F5 108.8(6) . . ?
F4 C52 F6 107.3(5) . . ?
F5 C52 F6 108.2(6) . . ?
F4 C52 S2 111.0(5) . . ?
F5 C52 S2 111.2(5) . . ?
F6 C52 S2 110.2(5) . . ?
C7 N1 C1 127.8(5) . . ?
C7 N1 H1 116.1 . . ?
C1 N1 H1 116.1 . . ?
C11 N2 C12 118.0(4) . . ?
C11 N2 Re1 120.9(3) . . ?
C12 N2 Re1 121.1(3) . . ?
C13 N3 C17 118.3(5) . . ?
C13 N3 Re1 125.6(4) . . ?
C17 N3 Re1 115.7(3) . . ?
C22 N4 C18 117.7(4) . . ?
C22 N4 Re1 125.0(3) . . ?
C18 N4 Re1 117.3(3) . . ?
C32 N5 C26 128.1(4) . . ?
C32 N5 H5A 115.9 . . ?
C26 N5 H5A 115.9 . . ?
C37 N6 C36 117.7(4) . . ?
C37 N6 Re2 121.3(3) . . ?
C36 N6 Re2 120.9(3) . . ?
C38 N7 C42 118.7(5) . . ?
C38 N7 Re2 124.6(3) . . ?
C42 N7 Re2 116.6(3) . . ?
C47 N8 C43 118.9(5) . . ?
C47 N8 Re2 124.8(4) . . ?
C43 N8 Re2 116.3(3) . . ?
O11 S1 O9 114.9(2) . . ?
O11 S1 O10 114.0(2) . . ?
O9 S1 O10 114.5(2) . . ?
O11 S1 C51 103.6(3) . . ?
O9 S1 C51 104.4(3) . . ?
O10 S1 C51 103.4(2) . . ?
O14 S2 O13 115.5(3) . . ?
O14 S2 O12 114.6(3) . . ?
O13 S2 O12 114.1(3) . . ?
O14 S2 C52 103.6(3) . . ?
O13 S2 C52 103.6(3) . . ?
O12 S2 C52 103.2(3) . . ?
C25 Re1 C24 86.0(2) . . ?
C25 Re1 C23 86.5(2) . . ?
C24 Re1 C23 90.1(2) . . ?
C25 Re1 N4 96.54(19) . . ?
C24 Re1 N4 93.1(2) . . ?
C23 Re1 N4 175.79(18) . . ?
C25 Re1 N3 95.5(2) . . ?
C24 Re1 N3 168.2(2) . . ?
C23 Re1 N3 101.7(2) . . ?
N4 Re1 N3 75.11(16) . . ?
C25 Re1 N2 177.3(2) . . ?
C24 Re1 N2 96.27(18) . . ?
C23 Re1 N2 92.10(18) . . ?
N4 Re1 N2 84.78(15) . . ?
N3 Re1 N2 82.60(15) . . ?
C49 Re2 C50 89.0(2) . . ?
C49 Re2 C48 90.4(3) . . ?
C50 Re2 C48 87.2(2) . . ?
C49 Re2 N7 94.3(2) . . ?
C50 Re2 N7 97.22(19) . . ?
C48 Re2 N7 173.63(19) . . ?
C49 Re2 N8 169.4(2) . . ?
C50 Re2 N8 92.7(2) . . ?
C48 Re2 N8 100.2(2) . . ?
N7 Re2 N8 75.10(16) . . ?
C49 Re2 N6 94.1(2) . . ?
C50 Re2 N6 175.9(2) . . ?
C48 Re2 N6 90.0(2) . . ?
N7 Re2 N6 85.37(15) . . ?
N8 Re2 N6 84.88(15) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.97
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.152
_refine_diff_density_min         -1.894
_refine_diff_density_rms         0.153
_database_code_depnum_ccdc_archive 'CCDC 893635'
#######################################################################
#
#                 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_sjp1026
#TrackingRef 'Re-pCl_sjp1026.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 Cl N4 O4 Re, C F3 O3 S'
_chemical_formula_sum            'C26 H17 Cl F3 N4 O7 Re S'
_chemical_formula_weight         808.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_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                   10.8109(4)
_cell_length_b                   11.2437(4)
_cell_length_c                   13.6707(5)
_cell_angle_alpha                109.009(2)
_cell_angle_beta                 91.179(2)
_cell_angle_gamma                117.018(2)
_cell_volume                     1371.34(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4849
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    4.679
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_T_max  0.7997
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9088
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.46
_reflns_number_total             6208
_reflns_number_gt                4849
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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)+(0.0369P)²+9.9112P] 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         6208
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.1349(10) 0.4129(9) 0.0055(7) 0.035(2) Uani 1 1 d . . .
C2 C 0.1930(10) 0.4032(10) -0.0851(7) 0.038(2) Uani 1 1 d . . .
H2 H 0.1807 0.3130 -0.1313 0.046 Uiso 1 1 calc R . .
C3 C 0.2686(10) 0.5254(10) -0.1074(7) 0.038(2) Uani 1 1 d . . .
H3 H 0.3104 0.5201 -0.1680 0.046 Uiso 1 1 calc R . .
C4 C 0.2828(9) 0.6551(10) -0.0407(7) 0.037(2) Uani 1 1 d . . .
C5 C 0.2253(10) 0.6656(10) 0.0486(7) 0.040(2) Uani 1 1 d . . .
H5 H 0.2361 0.7557 0.0937 0.048 Uiso 1 1 calc R . .
C6 C 0.1526(10) 0.5454(10) 0.0721(7) 0.042(2) Uani 1 1 d . . .
H6 H 0.1139 0.5525 0.1342 0.050 Uiso 1 1 calc R . .
C7 C -0.0354(9) 0.1596(10) -0.0298(7) 0.034(2) Uani 1 1 d . . .
C8 C -0.1205(9) 0.0553(8) 0.0225(6) 0.0286(18) Uani 1 1 d . . .
C9 C -0.2266(10) -0.0797(10) -0.0408(7) 0.039(2) Uani 1 1 d . . .
H9 H -0.2416 -0.1084 -0.1154 0.047 Uiso 1 1 calc R . .
C10 C -0.3107(9) -0.1726(10) 0.0044(7) 0.035(2) Uani 1 1 d . . .
H10 H -0.3839 -0.2663 -0.0387 0.042 Uiso 1 1 calc R . .
C11 C -0.2877(9) -0.1285(9) 0.1134(7) 0.036(2) Uani 1 1 d . . .
H11 H -0.3495 -0.1927 0.1434 0.043 Uiso 1 1 calc R . .
C12 C -0.1001(8) 0.0908(8) 0.1315(6) 0.0286(18) Uani 1 1 d . . .
H12 H -0.0248 0.1827 0.1755 0.034 Uiso 1 1 calc R . .
C13 C -0.0007(9) 0.3877(9) 0.3685(6) 0.0295(18) Uani 1 1 d . . .
H13 H 0.0854 0.3865 0.3809 0.035 Uiso 1 1 calc R . .
C14 C 0.0061(9) 0.5101(9) 0.3648(7) 0.0326(19) Uani 1 1 d . . .
H14 H 0.0950 0.5903 0.3712 0.039 Uiso 1 1 calc R . .
C15 C -0.1170(9) 0.5168(9) 0.3516(7) 0.0332(19) Uani 1 1 d . . .
H15 H -0.1137 0.6025 0.3513 0.040 Uiso 1 1 calc R . .
C16 C -0.2446(9) 0.3975(9) 0.3390(6) 0.0300(18) Uani 1 1 d . . .
H16 H -0.3305 0.4001 0.3295 0.036 Uiso 1 1 calc R . .
C17 C -0.2476(8) 0.2732(8) 0.3403(5) 0.0222(16) Uani 1 1 d . . .
C18 C -0.3777(9) 0.1414(8) 0.3278(6) 0.0264(17) Uani 1 1 d . . .
C19 C -0.5130(9) 0.1265(9) 0.3103(7) 0.0323(19) Uani 1 1 d . . .
H19 H -0.5239 0.2036 0.3050 0.039 Uiso 1 1 calc R . .
C20 C -0.6313(9) -0.0028(9) 0.3005(7) 0.0325(19) Uani 1 1 d . . .
H20 H -0.7239 -0.0148 0.2890 0.039 Uiso 1 1 calc R . .
C21 C -0.6121(9) -0.1121(9) 0.3077(7) 0.0332(19) Uani 1 1 d . . .
H21 H -0.6916 -0.2006 0.3015 0.040 Uiso 1 1 calc R . .
C22 C -0.4753(9) -0.0930(9) 0.3241(6) 0.0325(19) Uani 1 1 d . . .
H22 H -0.4634 -0.1697 0.3289 0.039 Uiso 1 1 calc R . .
C23 C 0.0534(9) 0.1175(9) 0.3614(6) 0.0284(18) Uani 1 1 d . . .
C24 C -0.1844(9) -0.1252(9) 0.3412(7) 0.0316(19) Uani 1 1 d . . .
C25 C -0.1213(8) 0.1191(8) 0.5006(7) 0.0255(18) Uani 1 1 d . . .
C26 C 0.4166(9) 0.5759(9) 0.4052(7) 0.034(2) Uani 1 1 d . . .
N1 N 0.0601(8) 0.2943(8) 0.0361(6) 0.0375(17) Uani 1 1 d . . .
H1 H 0.0772 0.3097 0.1035 0.045 Uiso 1 1 calc R . .
N2 N -0.1833(7) -0.0004(7) 0.1785(5) 0.0264(15) Uani 1 1 d . . .
N3 N -0.1245(7) 0.2674(7) 0.3554(5) 0.0245(14) Uani 1 1 d . . .
N4 N -0.3605(7) 0.0300(7) 0.3333(5) 0.0238(14) Uani 1 1 d . . .
O1 O -0.0611(7) 0.1200(7) -0.1261(5) 0.0457(16) Uani 1 1 d . . .
O2 O 0.1711(7) 0.1513(7) 0.3697(5) 0.0442(16) Uani 1 1 d . . .
O3 O -0.2085(6) -0.2375(6) 0.3362(5) 0.0402(15) Uani 1 1 d . . .
O4 O -0.1090(6) 0.1456(6) 0.5913(5) 0.0366(14) Uani 1 1 d . . .
O5 O 0.2295(6) 0.3875(7) 0.2392(4) 0.0377(14) Uani 1 1 d . . .
O6 O 0.4537(6) 0.3869(6) 0.2618(5) 0.0402(15) Uani 1 1 d . . .
O7 O 0.4452(7) 0.5772(7) 0.2191(5) 0.0414(15) Uani 1 1 d . . .
Cl1 Cl 0.3750(3) 0.8104(3) -0.07003(19) 0.0471(6) Uani 1 1 d . . .
Re1 Re -0.14577(4) 0.06477(4) 0.35141(3) 0.02679(12) Uani 1 1 d . . .
S1 S 0.3836(2) 0.4707(2) 0.26537(15) 0.0269(4) Uani 1 1 d . . .
F1 F 0.3631(6) 0.4927(6) 0.4609(4) 0.0430(12) Uani 1 1 d . . .
F2 F 0.3537(6) 0.6600(5) 0.4221(4) 0.0414(12) Uani 1 1 d . . .
F3 F 0.5540(5) 0.6640(6) 0.4469(4) 0.0462(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.392(12) . ?
C1 C2 1.394(12) . ?
C1 N1 1.415(12) . ?
C2 C3 1.382(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(12) . ?
C4 Cl1 1.759(9) . ?
C5 C6 1.370(13) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.224(10) . ?
C7 N1 1.350(11) . ?
C7 C8 1.525(12) . ?
C8 C9 1.375(12) . ?
C8 C12 1.396(11) . ?
C9 C10 1.371(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(12) . ?
C10 H10 0.9500 . ?
C11 N2 1.337(10) . ?
C11 H11 0.9500 . ?
C12 N2 1.375(11) . ?
C12 H12 0.9500 . ?
C13 N3 1.356(10) . ?
C13 C14 1.363(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(10) . ?
C16 H16 0.9500 . ?
C17 N3 1.376(9) . ?
C17 C18 1.461(11) . ?
C18 N4 1.372(9) . ?
C18 C19 1.400(11) . ?
C19 C20 1.395(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.368(11) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(11) . ?
C21 H21 0.9500 . ?
C22 N4 1.337(10) . ?
C22 H22 0.9500 . ?
C23 O2 1.141(10) . ?
C23 Re1 1.945(8) . ?
C24 O3 1.144(10) . ?
C24 Re1 1.937(9) . ?
C25 O4 1.166(10) . ?
C25 Re1 1.903(9) . ?
C26 F3 1.332(10) . ?
C26 F1 1.334(10) . ?
C26 F2 1.363(9) . ?
C26 S1 1.815(9) . ?
N1 H1 0.8800 . ?
N2 Re1 2.202(7) . ?
N3 Re1 2.165(6) . ?
N4 Re1 2.166(6) . ?
O5 S1 1.456(6) . ?
O6 S1 1.444(6) . ?
O7 S1 1.437(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.6(9) . . ?
C6 C1 N1 116.9(8) . . ?
C2 C1 N1 123.5(8) . . ?
C3 C2 C1 119.8(8) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.4(8) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 121.2(9) . . ?
C5 C4 Cl1 119.0(7) . . ?
C3 C4 Cl1 119.8(7) . . ?
C6 C5 C4 119.6(9) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.4(9) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 124.4(9) . . ?
O1 C7 C8 119.4(8) . . ?
N1 C7 C8 116.1(7) . . ?
C9 C8 C12 118.0(8) . . ?
C9 C8 C7 118.3(7) . . ?
C12 C8 C7 123.7(7) . . ?
C10 C9 C8 119.7(8) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.4(8) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
N2 C11 C10 123.5(9) . . ?
N2 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
N2 C12 C8 123.4(7) . . ?
N2 C12 H12 118.3 . . ?
C8 C12 H12 118.3 . . ?
N3 C13 C14 123.2(7) . . ?
N3 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C15 119.5(8) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 119.0(8) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 119.9(7) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N3 C17 C16 121.2(7) . . ?
N3 C17 C18 115.0(6) . . ?
C16 C17 C18 123.8(7) . . ?
N4 C18 C19 121.0(7) . . ?
N4 C18 C17 115.9(7) . . ?
C19 C18 C17 123.1(7) . . ?
C20 C19 C18 119.2(8) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C19 119.1(8) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 119.8(8) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
N4 C22 C21 122.0(8) . . ?
N4 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
O2 C23 Re1 178.2(7) . . ?
O3 C24 Re1 178.9(8) . . ?
O4 C25 Re1 176.8(7) . . ?
F3 C26 F1 108.0(7) . . ?
F3 C26 F2 106.7(7) . . ?
F1 C26 F2 106.1(7) . . ?
F3 C26 S1 112.7(6) . . ?
F1 C26 S1 112.1(6) . . ?
F2 C26 S1 110.8(6) . . ?
C7 N1 C1 125.3(7) . . ?
C7 N1 H1 117.3 . . ?
C1 N1 H1 117.3 . . ?
C11 N2 C12 116.1(7) . . ?
C11 N2 Re1 122.8(6) . . ?
C12 N2 Re1 121.1(5) . . ?
C13 N3 C17 117.2(7) . . ?
C13 N3 Re1 125.7(5) . . ?
C17 N3 Re1 117.1(5) . . ?
C22 N4 C18 118.9(7) . . ?
C22 N4 Re1 124.4(5) . . ?
C18 N4 Re1 116.7(5) . . ?
C25 Re1 C24 87.9(3) . . ?
C25 Re1 C23 89.5(3) . . ?
C24 Re1 C23 87.8(3) . . ?
C25 Re1 N3 94.3(3) . . ?
C24 Re1 N3 174.3(3) . . ?
C23 Re1 N3 97.5(3) . . ?
C25 Re1 N4 93.6(3) . . ?
C24 Re1 N4 99.4(3) . . ?
C23 Re1 N4 172.3(3) . . ?
N3 Re1 N4 75.2(2) . . ?
C25 Re1 N2 177.6(3) . . ?
C24 Re1 N2 92.2(3) . . ?
C23 Re1 N2 92.8(3) . . ?
N3 Re1 N2 85.4(2) . . ?
N4 Re1 N2 84.1(2) . . ?
O7 S1 O6 115.2(4) . . ?
O7 S1 O5 115.0(4) . . ?
O6 S1 O5 114.6(4) . . ?
O7 S1 C26 104.0(4) . . ?
O6 S1 C26 103.6(4) . . ?
O5 S1 C26 102.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.909
_refine_diff_density_min         -1.403
_refine_diff_density_rms         0.217
_database_code_depnum_ccdc_archive 'CCDC 893636'
#######################################################################
#
#                 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_sjp1014c
#TrackingRef 'Re-pF_sjp1014c.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 F N4 O4 Re, C F3 O3 S'
_chemical_formula_sum            'C26 H17 F4 N4 O7 Re S'
_chemical_formula_weight         791.70

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'
Re Re -1.0185 7.2310 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   8.3032(3)
_cell_length_b                   18.0645(5)
_cell_length_c                   18.8024(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9990(10)
_cell_angle_gamma                90.00
_cell_volume                     2799.22(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3623
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      25.95

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    4.495
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4668
_exptl_absorpt_correction_T_max  0.9564
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9272
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_sigmaI/netI    0.1119
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         25.95
_reflns_number_total             5445
_reflns_number_gt                3623
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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)+(0.0226P)²+16.0932P] 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         5445
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 1.6179(11) 0.3796(5) 0.6229(5) 0.027(2) Uani 1 1 d . . .
C2 C 1.7031(11) 0.3138(5) 0.6183(5) 0.032(2) Uani 1 1 d . . .
H2 H 1.6628 0.2699 0.6377 0.038 Uiso 1 1 calc R . .
C3 C 1.8464(12) 0.3099(6) 0.5861(5) 0.037(2) Uani 1 1 d . . .
H3 H 1.9006 0.2643 0.5808 0.045 Uiso 1 1 calc R . .
C4 C 1.9032(12) 0.3744(6) 0.5629(5) 0.036(2) Uani 1 1 d . . .
C5 C 1.8278(12) 0.4415(6) 0.5669(5) 0.042(3) Uani 1 1 d . . .
H5 H 1.8728 0.4853 0.5496 0.051 Uiso 1 1 calc R . .
C6 C 1.6827(12) 0.4433(5) 0.5975(5) 0.035(2) Uani 1 1 d . . .
H6 H 1.6279 0.4891 0.6008 0.042 Uiso 1 1 calc R . .
C7 C 1.3604(11) 0.3335(5) 0.6606(4) 0.027(2) Uani 1 1 d . . .
C8 C 1.2274(10) 0.3567(5) 0.7035(5) 0.025(2) Uani 1 1 d . . .
C9 C 1.1700(12) 0.4287(5) 0.7103(5) 0.034(2) Uani 1 1 d . . .
H9 H 1.2190 0.4691 0.6886 0.041 Uiso 1 1 calc R . .
C10 C 1.0427(12) 0.4405(6) 0.7485(5) 0.038(2) Uani 1 1 d . . .
H10 H 1.0026 0.4892 0.7542 0.045 Uiso 1 1 calc R . .
C11 C 0.9739(11) 0.3814(5) 0.7784(5) 0.031(2) Uani 1 1 d . . .
H11 H 0.8838 0.3903 0.8039 0.037 Uiso 1 1 calc R . .
C12 C 1.1507(10) 0.2986(5) 0.7353(4) 0.027(2) Uani 1 1 d . . .
H12 H 1.1866 0.2492 0.7298 0.032 Uiso 1 1 calc R . .
C13 C 1.2687(11) 0.1507(5) 0.8465(5) 0.031(2) Uani 1 1 d . . .
H13 H 1.2316 0.1244 0.8039 0.037 Uiso 1 1 calc R . .
C14 C 1.4241(11) 0.1384(5) 0.8776(5) 0.033(2) Uani 1 1 d . . .
H14 H 1.4928 0.1045 0.8572 0.040 Uiso 1 1 calc R . .
C15 C 1.4787(12) 0.1769(5) 0.9401(5) 0.036(2) Uani 1 1 d . . .
H15 H 1.5858 0.1697 0.9632 0.043 Uiso 1 1 calc R . .
C16 C 1.3762(11) 0.2247(5) 0.9675(5) 0.035(2) Uani 1 1 d . . .
H16 H 1.4113 0.2506 1.0106 0.042 Uiso 1 1 calc R . .
C17 C 1.2208(10) 0.2362(4) 0.9332(4) 0.022(2) Uani 1 1 d . . .
C18 C 1.1026(10) 0.2886(5) 0.9592(4) 0.025(2) Uani 1 1 d . . .
C19 C 1.1407(12) 0.3343(5) 1.0172(5) 0.034(2) Uani 1 1 d . . .
H19 H 1.2457 0.3324 1.0436 0.040 Uiso 1 1 calc R . .
C20 C 1.0262(13) 0.3830(5) 1.0370(5) 0.034(2) Uani 1 1 d . . .
H20 H 1.0520 0.4156 1.0764 0.041 Uiso 1 1 calc R . .
C21 C 0.8735(12) 0.3836(6) 0.9987(5) 0.037(2) Uani 1 1 d . . .
H21 H 0.7926 0.4166 1.0114 0.045 Uiso 1 1 calc R . .
C22 C 0.8393(12) 0.3353(5) 0.9411(5) 0.032(2) Uani 1 1 d . . .
H22 H 0.7336 0.3353 0.9152 0.039 Uiso 1 1 calc R . .
C23 C 0.9089(10) 0.1609(5) 0.7401(5) 0.027(2) Uani 1 1 d . . .
C24 C 0.6946(12) 0.2467(5) 0.7969(5) 0.027(2) Uani 1 1 d . . .
C25 C 0.8436(11) 0.1316(5) 0.8716(5) 0.025(2) Uani 1 1 d . . .
C26 C 0.4936(13) 0.5486(6) 0.8752(6) 0.048(3) Uani 1 1 d . . .
N1 N 1.4755(9) 0.3862(4) 0.6564(4) 0.0295(18) Uani 1 1 d . . .
H1 H 1.4596 0.4291 0.6767 0.035 Uiso 1 1 calc R . .
N2 N 1.0257(8) 0.3118(4) 0.7740(4) 0.0239(17) Uani 1 1 d . . .
N3 N 1.1653(9) 0.1981(4) 0.8728(4) 0.0294(18) Uani 1 1 d . . .
N4 N 0.9533(8) 0.2879(4) 0.9209(3) 0.0242(16) Uani 1 1 d . . .
O1 O 1.3625(7) 0.2722(3) 0.6335(3) 0.0322(15) Uani 1 1 d . . .
O2 O 0.9034(8) 0.1272(4) 0.6884(4) 0.0413(17) Uani 1 1 d . . .
O3 O 0.5625(8) 0.2623(3) 0.7813(4) 0.0395(17) Uani 1 1 d . . .
O4 O 0.8011(8) 0.0783(3) 0.8977(3) 0.0358(16) Uani 1 1 d . . .
O5 O 0.4975(8) 0.5233(3) 0.7429(3) 0.0402(17) Uani 1 1 d . . .
O6 O 0.6260(9) 0.4343(4) 0.8271(4) 0.054(2) Uani 1 1 d . . .
O7 O 0.7494(8) 0.5550(4) 0.8133(4) 0.055(2) Uani 1 1 d . . .
F1 F 2.0464(7) 0.3726(3) 0.5326(3) 0.0520(16) Uani 1 1 d . . .
F2 F 0.3518(7) 0.5131(3) 0.8780(3) 0.0576(17) Uani 1 1 d . . .
F3 F 0.4626(8) 0.6190(3) 0.8682(4) 0.070(2) Uani 1 1 d . . .
F4 F 0.5793(9) 0.5387(4) 0.9417(3) 0.073(2) Uani 1 1 d . . .
Re1 Re 0.91744(4) 0.217817(19) 0.826805(19) 0.02475(12) Uani 1 1 d . . .
S1 S 0.6045(3) 0.51129(14) 0.80800(13) 0.0361(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.380(12) . ?
C1 C2 1.392(12) . ?
C1 N1 1.411(11) . ?
C2 C3 1.401(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.350(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(13) . ?
C4 F1 1.379(10) . ?
C5 C6 1.397(13) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.221(10) . ?
C7 N1 1.358(11) . ?
C7 C8 1.503(12) . ?
C8 C9 1.397(12) . ?
C8 C12 1.400(11) . ?
C9 C10 1.365(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(12) . ?
C10 H10 0.9500 . ?
C11 N2 1.336(11) . ?
C11 H11 0.9500 . ?
C12 N2 1.359(11) . ?
C12 H12 0.9500 . ?
C13 N3 1.350(11) . ?
C13 C14 1.368(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.358(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(12) . ?
C16 H16 0.9500 . ?
C17 N3 1.359(11) . ?
C17 C18 1.489(12) . ?
C18 N4 1.356(10) . ?
C18 C19 1.374(12) . ?
C19 C20 1.379(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(12) . ?
C21 H21 0.9500 . ?
C22 N4 1.365(11) . ?
C22 H22 0.9500 . ?
C23 O2 1.143(10) . ?
C23 Re1 1.922(10) . ?
C24 O3 1.136(10) . ?
C24 Re1 1.939(10) . ?
C25 O4 1.155(10) . ?
C25 Re1 1.907(9) . ?
C26 F3 1.300(12) . ?
C26 F2 1.348(11) . ?
C26 F4 1.373(13) . ?
C26 S1 1.784(11) . ?
N1 H1 0.8800 . ?
N2 Re1 2.212(7) . ?
N3 Re1 2.163(7) . ?
N4 Re1 2.165(7) . ?
O5 S1 1.439(7) . ?
O6 S1 1.442(7) . ?
O7 S1 1.432(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
C6 C1 C2 117.9(9) . . ?
C6 C1 N1 117.8(8) . . ?
C2 C1 N1 124.1(8) . . ?
C1 C2 C3 122.3(9) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 116.4(9) . . ?
C4 C3 H3 121.8 . . ?
C2 C3 H3 121.8 . . ?
C3 C4 C5 124.4(9) . . ?
C3 C4 F1 117.7(9) . . ?
C5 C4 F1 117.8(9) . . ?
C4 C5 C6 117.8(9) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 121.0(9) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O1 C7 N1 124.5(8) . . ?
O1 C7 C8 121.7(8) . . ?
N1 C7 C8 113.8(8) . . ?
C9 C8 C12 118.8(8) . . ?
C9 C8 C7 126.1(8) . . ?
C12 C8 C7 115.0(8) . . ?
C10 C9 C8 119.2(9) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 119.0(9) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N2 C11 C10 123.9(9) . . ?
N2 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
N2 C12 C8 121.0(8) . . ?
N2 C12 H12 119.5 . . ?
C8 C12 H12 119.5 . . ?
N3 C13 C14 123.7(9) . . ?
N3 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C13 C14 C15 118.2(9) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C16 C15 C14 118.9(9) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 120.7(9) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
N3 C17 C16 121.0(8) . . ?
N3 C17 C18 115.2(7) . . ?
C16 C17 C18 123.8(8) . . ?
N4 C18 C19 122.4(8) . . ?
N4 C18 C17 114.6(7) . . ?
C19 C18 C17 123.1(8) . . ?
C18 C19 C20 119.9(9) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 118.9(9) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C22 119.2(9) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N4 C22 C21 121.8(9) . . ?
N4 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
O2 C23 Re1 179.7(9) . . ?
O3 C24 Re1 177.7(8) . . ?
O4 C25 Re1 178.4(8) . . ?
F3 C26 F2 107.9(9) . . ?
F3 C26 F4 107.0(9) . . ?
F2 C26 F4 105.1(9) . . ?
F3 C26 S1 114.3(8) . . ?
F2 C26 S1 112.1(7) . . ?
F4 C26 S1 109.9(8) . . ?
C7 N1 C1 126.9(8) . . ?
C7 N1 H1 116.6 . . ?
C1 N1 H1 116.6 . . ?
C11 N2 C12 118.1(7) . . ?
C11 N2 Re1 122.9(6) . . ?
C12 N2 Re1 119.0(6) . . ?
C13 N3 C17 117.5(8) . . ?
C13 N3 Re1 125.1(6) . . ?
C17 N3 Re1 117.4(6) . . ?
C18 N4 C22 117.8(8) . . ?
C18 N4 Re1 117.8(6) . . ?
C22 N4 Re1 124.3(6) . . ?
C25 Re1 C23 87.5(4) . . ?
C25 Re1 C24 90.1(4) . . ?
C23 Re1 C24 87.9(4) . . ?
C25 Re1 N3 91.7(3) . . ?
C23 Re1 N3 100.7(3) . . ?
C24 Re1 N3 171.3(3) . . ?
C25 Re1 N4 97.9(3) . . ?
C23 Re1 N4 173.1(3) . . ?
C24 Re1 N4 96.4(3) . . ?
N3 Re1 N4 74.9(3) . . ?
C25 Re1 N2 174.3(3) . . ?
C23 Re1 N2 90.3(3) . . ?
C24 Re1 N2 95.1(3) . . ?
N3 Re1 N2 83.5(3) . . ?
N4 Re1 N2 84.0(3) . . ?
O7 S1 O5 113.7(4) . . ?
O7 S1 O6 115.9(5) . . ?
O5 S1 O6 113.7(4) . . ?
O7 S1 C26 104.1(5) . . ?
O5 S1 C26 103.2(5) . . ?
O6 S1 C26 104.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.95
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.624
_refine_diff_density_min         -0.986
_refine_diff_density_rms         0.207
_database_code_depnum_ccdc_archive 'CCDC 893637'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 F3 I N4 O7 Re S'
_chemical_formula_sum            'C26 H17 F3 I N4 O7 Re S'
_chemical_formula_weight         899.60

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.3050(3)
_cell_length_b                   18.7280(8)
_cell_length_c                   17.2820(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.354(2)
_cell_angle_gamma                90
_cell_volume                     2952.69(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4179
_cell_measurement_theta_min      2.232
_cell_measurement_theta_max      25.252

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.301
_shelx_estimated_absorpt_T_min   0.232
_shelx_estimated_absorpt_T_max   0.816
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.232
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11154
_diffrn_reflns_av_unetI/netI     0.0874
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         27.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             6477
_reflns_number_gt                4179
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'COLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²+9.8764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6477
_refine_ls_number_parameters     416
_refine_ls_number_restraints     276
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1706
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.09632(4) 0.03651(2) 0.32781(2) 0.04367(16) Uani 1 1 d . . . . .
C1 C 0.7975(18) -0.2113(9) 0.3537(8) 0.043(3) Uani 0.67(2) 1 d . U P A 1
C2 C 0.8538(19) -0.2118(10) 0.4330(9) 0.052(4) Uani 0.67(2) 1 d . U P A 1
H2 H 0.7950 -0.1978 0.4695 0.063 Uiso 0.67(2) 1 calc R U P A 1
C3 C 0.999(2) -0.2331(10) 0.4595(10) 0.057(4) Uani 0.67(2) 1 d . U P A 1
H3 H 1.0363 -0.2355 0.5147 0.068 Uiso 0.67(2) 1 calc R U P A 1
C4 C 1.088(2) -0.2507(10) 0.4083(10) 0.055(3) Uani 0.67(2) 1 d . U P A 1
C5 C 1.0313(18) -0.2502(10) 0.3279(9) 0.054(3) Uani 0.67(2) 1 d . U P A 1
H5 H 1.0925 -0.2625 0.2920 0.064 Uiso 0.67(2) 1 calc R U P A 1
C6 C 0.8855(6) -0.2319(3) 0.2992(3) 0.051(3) Uani 0.67(2) 1 d . U P A 1
H6 H 0.8458 -0.2333 0.2442 0.061 Uiso 0.67(2) 1 calc R U P A 1
C1A C 0.8162(6) -0.1972(3) 0.3533(3) 0.049(5) Uani 0.33(2) 1 d R U P A 2
C2A C 0.8913(6) -0.1806(3) 0.4288(3) 0.055(5) Uani 0.33(2) 1 d R U P A 2
H2A H 0.8442 -0.1540 0.4635 0.067 Uiso 0.33(2) 1 calc R U P A 2
C3A C 1.0355(6) -0.2029(3) 0.4538(3) 0.054(5) Uani 0.33(2) 1 d R U P A 2
H3A H 1.0869 -0.1915 0.5054 0.064 Uiso 0.33(2) 1 calc R U P A 2
C4A C 1.1046(6) -0.2418(3) 0.4031(3) 0.055(5) Uani 0.33(2) 1 d R U P A 2
C5A C 1.0294(6) -0.2585(3) 0.3276(3) 0.052(5) Uani 0.33(2) 1 d R U P A 2
H5A H 1.0766 -0.2851 0.2929 0.062 Uiso 0.33(2) 1 calc R U P A 2
C6A C 0.8853(6) -0.2362(3) 0.3026(3) 0.052(5) Uani 0.33(2) 1 d R U P A 2
H6A H 0.8339 -0.2476 0.2510 0.063 Uiso 0.33(2) 1 calc R U P A 2
C7 C 0.5632(6) -0.1507(3) 0.3585(3) 0.045(2) Uani 1 1 d R . . . .
C8 C 0.4147(6) -0.1369(3) 0.3075(3) 0.043(2) Uani 1 1 d R . . A .
C9 C 0.3515(6) -0.1736(3) 0.2412(3) 0.053(3) Uani 1 1 d R . . A .
H9 H 0.4036 -0.2109 0.2216 0.064 Uiso 1 1 calc R U . A .
C10 C 0.2117(12) -0.1561(6) 0.2031(7) 0.055(3) Uani 1 1 d . . . . .
H10 H 0.1649 -0.1828 0.1584 0.066 Uiso 1 1 calc R U . A .
C11 C 0.1408(11) -0.1003(6) 0.2300(6) 0.051(3) Uani 1 1 d . . . . .
H11 H 0.0439 -0.0891 0.2038 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3365(11) -0.0812(6) 0.3308(5) 0.047(2) Uani 1 1 d . . . . .
H12 H 0.3792 -0.0557 0.3772 0.056 Uiso 1 1 calc R U . A .
N2 N 0.2033(9) -0.0609(5) 0.2918(5) 0.048(2) Uani 1 1 d . . . . .
N3 N 0.3004(10) 0.0891(5) 0.3166(6) 0.054(2) Uani 1 1 d . . . B 1
C13 C 0.4160(14) 0.1017(7) 0.3781(8) 0.070(3) Uani 1 1 d . U . B 1
H13 H 0.4039 0.0948 0.4309 0.084 Uiso 1 1 calc R U . B 1
C14 C 0.5502(16) 0.1246(8) 0.3637(10) 0.090(4) Uani 1 1 d . U . B 1
H14 H 0.6302 0.1325 0.4063 0.108 Uiso 1 1 calc R U . B 1
C15 C 0.5659(16) 0.1354(8) 0.2895(11) 0.086(4) Uani 1 1 d . U . B 1
H15 H 0.6575 0.1517 0.2799 0.104 Uiso 1 1 calc R U . B 1
C16 C 0.4555(15) 0.1239(6) 0.2280(9) 0.073(4) Uani 1 1 d . U . B 1
H16 H 0.4677 0.1321 0.1754 0.087 Uiso 1 1 calc R U . B 1
C17 C 0.3207(12) 0.0992(6) 0.2435(8) 0.058(3) Uani 1 1 d . . . B 1
C18 C 0.1934(13) 0.0854(6) 0.1804(6) 0.053(3) Uani 1 1 d . . . B 1
C19 C 0.1876(17) 0.0996(7) 0.0996(8) 0.071(4) Uani 1 1 d . . . B 1
H19 H 0.2722 0.1171 0.0827 0.085 Uiso 1 1 calc R U . B 1
C20 C 0.0616(18) 0.0883(8) 0.0457(8) 0.079(4) Uani 1 1 d . . . B 1
H20 H 0.0583 0.0980 -0.0086 0.095 Uiso 1 1 calc R U . B 1
C21 C -0.0596(16) 0.0631(7) 0.0700(6) 0.068(3) Uani 1 1 d . . . B 1
H21 H -0.1480 0.0545 0.0331 0.082 Uiso 1 1 calc R U . B 1
C22 C -0.0507(13) 0.0503(6) 0.1488(6) 0.051(3) Uani 1 1 d . . . B 1
H22 H -0.1354 0.0328 0.1656 0.061 Uiso 1 1 calc R U . B 1
N4 N 0.0715(9) 0.0613(4) 0.2040(4) 0.0415(18) Uani 1 1 d . . . B 1
C23 C 0.1455(12) 0.0121(7) 0.4372(7) 0.060(3) Uani 1 1 d . . . C 1
C24 C -0.0911(13) -0.0121(7) 0.3247(6) 0.054(3) Uani 1 1 d . . . D 1
C25 C 0.0058(13) 0.1229(8) 0.3515(7) 0.066(3) Uani 1 1 d . . . E 1
C26 C 0.5504(17) -0.0599(9) 0.1130(8) 0.083(4) Uani 1 1 d . . . F 1
N1 N 0.6564(9) -0.1871(5) 0.3209(5) 0.051(2) Uani 1 1 d . . . A 1
H1 H 0.6243 -0.1964 0.2705 0.061 Uiso 1 1 calc R U . A 1
O1 O 0.5906(8) -0.1322(4) 0.4263(4) 0.059(2) Uani 1 1 d . . . G 1
O2 O 0.1788(10) -0.0065(7) 0.5019(5) 0.097(3) Uani 1 1 d . . . C 1
O3 O -0.2028(10) -0.0361(5) 0.3233(5) 0.077(3) Uani 1 1 d . . . D 1
O4 O -0.0530(11) 0.1753(5) 0.3613(5) 0.084(3) Uani 1 1 d . . . E 1
O5 O 0.6040(9) -0.1929(5) 0.1475(4) 0.067(2) Uani 1 1 d . . . F 1
O6 O 0.8067(10) -0.1187(6) 0.1252(6) 0.103(4) Uani 1 1 d . . . F 1
O7 O 0.6149(10) -0.1541(7) 0.0154(4) 0.094(3) Uani 1 1 d . . . F 1
F1 F 0.5664(12) -0.0438(5) 0.1891(5) 0.114(3) Uani 1 1 d . . . F 1
F2 F 0.4119(9) -0.0679(5) 0.0849(5) 0.099(3) Uani 1 1 d . . . F 1
F3 F 0.5953(11) -0.0030(6) 0.0767(6) 0.130(4) Uani 1 1 d . . . F 1
I1 I 1.31132(9) -0.27959(5) 0.44888(5) 0.0731(3) Uani 1 1 d . . . A 1
S1 S 0.6569(3) -0.1401(2) 0.09832(16) 0.0723(10) Uani 1 1 d . . . F 1


_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 C25 1.905(13) . ?
Re1 C23 1.911(12) . ?
Re1 C24 1.959(12) . ?
Re1 N4 2.157(8) . ?
Re1 N3 2.181(9) . ?
Re1 N2 2.226(9) . ?
C1 C2 1.37(2) . ?
C1 N1 1.400(17) . ?
C1 C6 1.418(16) . ?
C2 C3 1.39(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.37(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.39(2) . ?
C4 I1 2.125(17) . ?
C5 C6 1.392(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7 O1 1.201(8) . ?
C7 N1 1.364(9) . ?
C7 C8 1.5079 . ?
C8 C9 1.3653 . ?
C8 C12 1.376(12) . ?
C9 C10 1.377(12) . ?
C9 H9 0.9500 . ?
C10 C11 1.366(15) . ?
C10 H10 0.9500 . ?
C11 N2 1.333(13) . ?
C11 H11 0.9500 . ?
C12 N2 1.344(12) . ?
C12 H12 0.9500 . ?
N3 C17 1.328(14) . ?
N3 C13 1.375(15) . ?
C13 C14 1.388(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.33(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.343(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.411(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.467(16) . ?
C18 N4 1.356(13) . ?
C18 C19 1.412(16) . ?
C19 C20 1.363(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.363(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.370(15) . ?
C21 H21 0.9500 . ?
C22 N4 1.347(13) . ?
C22 H22 0.9500 . ?
C23 O2 1.154(13) . ?
C24 O3 1.128(13) . ?
C25 O4 1.153(14) . ?
C26 F2 1.294(16) . ?
C26 F1 1.328(15) . ?
C26 F3 1.344(17) . ?
C26 S1 1.844(17) . ?
N1 H1 0.8800 . ?
O5 S1 1.451(8) . ?
O6 S1 1.437(9) . ?
O7 S1 1.433(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 Re1 C23 91.2(5) . . ?
C25 Re1 C24 88.4(5) . . ?
C23 Re1 C24 87.4(5) . . ?
C25 Re1 N4 93.7(4) . . ?
C23 Re1 N4 172.3(4) . . ?
C24 Re1 N4 98.7(4) . . ?
C25 Re1 N3 93.7(5) . . ?
C23 Re1 N3 98.8(4) . . ?
C24 Re1 N3 173.4(4) . . ?
N4 Re1 N3 74.9(3) . . ?
C25 Re1 N2 175.9(4) . . ?
C23 Re1 N2 92.7(4) . . ?
C24 Re1 N2 93.2(4) . . ?
N4 Re1 N2 82.3(3) . . ?
N3 Re1 N2 84.3(3) . . ?
C2 C1 N1 123.5(13) . . ?
C2 C1 C6 120.5(13) . . ?
N1 C1 C6 115.9(11) . . ?
C1 C2 C3 119.1(15) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.9(15) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.9(16) . . ?
C3 C4 I1 121.8(12) . . ?
C5 C4 I1 119.3(14) . . ?
C4 C5 C6 120.9(15) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.6(10) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C2A C1A C6A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
O1 C7 N1 125.2(6) . . ?
O1 C7 C8 121.0(4) . . ?
N1 C7 C8 113.7(4) . . ?
C9 C8 C12 117.5(5) . . ?
C9 C8 C7 126.7 . . ?
C12 C8 C7 115.7(5) . . ?
C8 C9 C10 119.5(5) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 119.5(9) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N2 C11 C10 122.1(10) . . ?
N2 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
N2 C12 C8 123.7(8) . . ?
N2 C12 H12 118.1 . . ?
C8 C12 H12 118.1 . . ?
C11 N2 C12 117.4(9) . . ?
C11 N2 Re1 121.9(7) . . ?
C12 N2 Re1 120.7(7) . . ?
C17 N3 C13 118.3(11) . . ?
C17 N3 Re1 116.0(7) . . ?
C13 N3 Re1 124.9(9) . . ?
N3 C13 C14 120.6(13) . . ?
N3 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.5(14) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.7(14) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 118.2(14) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
N3 C17 C16 121.8(12) . . ?
N3 C17 C18 115.9(9) . . ?
C16 C17 C18 122.3(11) . . ?
N4 C18 C19 119.2(11) . . ?
N4 C18 C17 115.9(9) . . ?
C19 C18 C17 124.7(11) . . ?
C20 C19 C18 120.5(12) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.7(11) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 118.4(12) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
N4 C22 C21 123.7(11) . . ?
N4 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
C22 N4 C18 118.5(9) . . ?
C22 N4 Re1 125.4(7) . . ?
C18 N4 Re1 115.9(7) . . ?
O2 C23 Re1 175.8(12) . . ?
O3 C24 Re1 175.7(11) . . ?
O4 C25 Re1 176.0(10) . . ?
F2 C26 F1 107.9(13) . . ?
F2 C26 F3 107.2(12) . . ?
F1 C26 F3 107.4(14) . . ?
F2 C26 S1 112.0(12) . . ?
F1 C26 S1 111.3(10) . . ?
F3 C26 S1 110.9(11) . . ?
C7 N1 C1 127.1(9) . . ?
C7 N1 H1 116.5 . . ?
C1 N1 H1 116.5 . . ?
O7 S1 O6 115.5(6) . . ?
O7 S1 O5 113.8(6) . . ?
O6 S1 O5 114.8(5) . . ?
O7 S1 C26 103.8(7) . . ?
O6 S1 C26 104.0(7) . . ?
O5 S1 C26 102.8(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.95 2.26 2.850(18) 119.2 .
C3 H3 O4 0.95 2.40 3.225(18) 145.1 3_656
C11 H11 O6 0.95 2.42 3.293(13) 153.3 1_455
C13 H13 O1 0.95 2.56 3.440(16) 154.9 3_656
C19 H19 O7 0.95 2.27 3.133(14) 150.2 3_655
N1 H1 O5 0.88 2.10 2.942(11) 160.3 .

_refine_diff_density_max         1.871
_refine_diff_density_min         -1.747
_refine_diff_density_rms         0.215

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 893638'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 I N4 O4 Re, C F3 O3 S'
_chemical_formula_sum            'C26 H17 F3 I N4 O7 Re S'
_chemical_formula_weight         899.60

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'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.5630(8)
_cell_length_b                   20.396(2)
_cell_length_c                   16.2270(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.112(7)
_cell_angle_gamma                90
_cell_volume                     2826.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4080
_cell_measurement_theta_min      2.517
_cell_measurement_theta_max      25.24

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    5.537
_shelx_estimated_absorpt_T_min   0.221
_shelx_estimated_absorpt_T_max   0.809
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.221
_exptl_absorpt_correction_T_max  0.809
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10313
_diffrn_reflns_av_unetI/netI     0.0897
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.893
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.893
_reflns_number_total             5903
_reflns_number_gt                4080
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'COLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    'SHELXS-97 ((Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+22.4584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5903
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.1852
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2879(15) -0.2039(6) 0.1128(8) 0.047(3) Uani 1 1 d . . . . .
C2 C 0.2634(16) -0.2176(5) 0.0305(8) 0.047(3) Uani 1 1 d . . . . .
H2 H 0.3443 -0.2115 -0.0059 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1179(16) -0.2405(5) 0.0016(8) 0.045(3) Uani 1 1 d . . . . .
H3 H 0.0999 -0.2513 -0.0552 0.054 Uiso 1 1 calc R U . . .
C4 C -0.0020(15) -0.2480(6) 0.0532(8) 0.048(3) Uani 1 1 d . . . . .
C5 C 0.0285(16) -0.2382(7) 0.1358(8) 0.051(3) Uani 1 1 d . . . . .
H5 H -0.0502 -0.2473 0.1725 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1739(17) -0.2149(6) 0.1669(8) 0.052(3) Uani 1 1 d . . . . .
H6 H 0.1940 -0.2067 0.2243 0.062 Uiso 1 1 calc R U . . .
C7 C 0.5302(15) -0.1350(6) 0.1074(8) 0.044(3) Uani 1 1 d . . . . .
C8 C 0.6770(14) -0.1145(5) 0.1617(7) 0.042(3) Uani 1 1 d . . . . .
C9 C 0.7439(13) -0.1537(5) 0.2251(7) 0.039(3) Uani 1 1 d . . . . .
H9 H 0.6975 -0.1939 0.2401 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8815(15) -0.1310(6) 0.2653(7) 0.046(3) Uani 1 1 d . . . . .
H10 H 0.9342 -0.1575 0.3067 0.056 Uiso 1 1 calc R U . . .
C11 C 0.9425(14) -0.0723(5) 0.2471(8) 0.042(3) Uani 1 1 d . . . . .
H11 H 1.0357 -0.0579 0.2770 0.051 Uiso 1 1 calc R U . . .
C12 C 0.7443(15) -0.0545(6) 0.1453(7) 0.044(3) Uani 1 1 d . . . . .
H12 H 0.6968 -0.0277 0.1027 0.053 Uiso 1 1 calc R U . . .
C13 C 0.6236(17) 0.1200(6) 0.1500(7) 0.048(3) Uani 1 1 d . . . . .
H13 H 0.6348 0.1129 0.0928 0.058 Uiso 1 1 calc R U . . .
C14 C 0.4852(17) 0.1477(6) 0.1743(8) 0.054(3) Uani 1 1 d . . . . .
H14 H 0.4064 0.1617 0.1339 0.065 Uiso 1 1 calc R U . . .
C15 C 0.4636(16) 0.1548(6) 0.2567(8) 0.048(3) Uani 1 1 d . . . . .
H15 H 0.3682 0.1719 0.2741 0.057 Uiso 1 1 calc R U . . .
C16 C 0.5831(14) 0.1364(6) 0.3140(7) 0.042(3) Uani 1 1 d . . . . .
H16 H 0.5714 0.1417 0.3714 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7222(15) 0.1099(6) 0.2867(7) 0.043(3) Uani 1 1 d . . . . .
C18 C 0.8588(15) 0.0897(6) 0.3425(8) 0.044(3) Uani 1 1 d . . . . .
C19 C 0.8564(16) 0.0952(6) 0.4277(7) 0.046(3) Uani 1 1 d . . . . .
H19 H 0.7655 0.1106 0.4518 0.055 Uiso 1 1 calc R U . . .
C20 C 0.9909(18) 0.0775(6) 0.4778(8) 0.052(3) Uani 1 1 d . . . . .
H20 H 0.9903 0.0786 0.5363 0.062 Uiso 1 1 calc R U . . .
C21 C 1.1208(16) 0.0589(5) 0.4413(7) 0.043(3) Uani 1 1 d . . . . .
H21 H 1.2149 0.0490 0.4735 0.052 Uiso 1 1 calc R U . . .
C22 C 1.1138(16) 0.0547(6) 0.3547(8) 0.045(3) Uani 1 1 d . . . . .
H22 H 1.2044 0.0402 0.3296 0.055 Uiso 1 1 calc R U . . .
C23 C 0.9363(15) 0.0698(5) 0.0531(9) 0.047(3) Uani 1 1 d . . . . .
C24 C 1.1716(18) 0.0295(7) 0.1529(7) 0.052(3) Uani 1 1 d . . . . .
C25 C 1.0544(17) 0.1550(7) 0.1732(7) 0.052(3) Uani 1 1 d . . . . .
C26 C 0.4966(17) 0.0540(6) 0.6332(8) 0.051(3) Uani 1 1 d . . . . .
N1 N 0.4342(12) -0.1769(5) 0.1474(7) 0.051(3) Uani 1 1 d . . . . .
H1 H 0.4647 -0.1881 0.1984 0.061 Uiso 1 1 calc R U . . .
N2 N 0.8752(12) -0.0334(4) 0.1879(6) 0.043(2) Uani 1 1 d . . . . .
N3 N 0.7429(12) 0.1027(5) 0.2055(6) 0.051(3) Uani 1 1 d . . . . .
N4 N 0.9868(12) 0.0699(4) 0.3056(6) 0.040(2) Uani 1 1 d . . . . .
O1 O 0.5103(11) -0.1178(4) 0.0365(5) 0.054(2) Uani 1 1 d . . . . .
O2 O 0.9168(12) 0.0712(4) -0.0180(6) 0.059(3) Uani 1 1 d . . . . .
O3 O 1.2974(12) 0.0097(5) 0.1425(5) 0.057(2) Uani 1 1 d . . . . .
O4 O 1.1062(11) 0.2068(5) 0.1759(5) 0.053(2) Uani 1 1 d . . . . .
O5 O 0.5403(11) 0.1767(4) 0.6701(5) 0.051(2) Uani 1 1 d . . . . .
O6 O 0.7596(11) 0.1122(5) 0.6273(6) 0.064(3) Uani 1 1 d . . . . .
O7 O 0.5489(10) 0.1422(4) 0.5271(5) 0.053(2) Uani 1 1 d . . . . .
F1 F 0.5244(10) 0.0354(4) 0.7120(5) 0.064(2) Uani 1 1 d . . . . .
F2 F 0.3406(10) 0.0604(4) 0.6221(5) 0.061(2) Uani 1 1 d . . . . .
F3 F 0.5386(10) 0.0054(4) 0.5871(5) 0.065(2) Uani 1 1 d . . . . .
Re1 Re 0.97050(6) 0.06758(2) 0.17205(3) 0.04107(19) Uani 1 1 d . . . . .
I1 I -0.23079(11) -0.27598(4) 0.00929(5) 0.0530(3) Uani 1 1 d . . . . .
S1 S 0.5980(4) 0.12963(16) 0.61246(18) 0.0473(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.366(17) . ?
C1 C6 1.377(18) . ?
C1 N1 1.444(15) . ?
C2 C3 1.381(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.362(17) . ?
C4 I1 2.114(13) . ?
C5 C6 1.393(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.202(14) . ?
C7 N1 1.380(16) . ?
C7 C8 1.541(15) . ?
C8 C12 1.386(16) . ?
C8 C9 1.393(15) . ?
C9 C10 1.384(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.349(16) . ?
C10 H10 0.9500 . ?
C11 N2 1.343(14) . ?
C11 H11 0.9500 . ?
C12 N2 1.345(14) . ?
C12 H12 0.9500 . ?
C13 N3 1.360(15) . ?
C13 C14 1.395(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.409(17) . ?
C16 H16 0.9500 . ?
C17 N3 1.349(15) . ?
C17 C18 1.485(16) . ?
C18 N4 1.348(15) . ?
C18 C19 1.389(16) . ?
C19 C20 1.408(17) . ?
C19 H19 0.9500 . ?
C20 C21 1.352(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.405(17) . ?
C21 H21 0.9500 . ?
C22 N4 1.337(15) . ?
C22 H22 0.9500 . ?
C23 O2 1.155(15) . ?
C23 Re1 1.931(14) . ?
C24 O3 1.174(15) . ?
C24 Re1 1.935(16) . ?
C25 O4 1.145(15) . ?
C25 Re1 1.923(14) . ?
C26 F3 1.308(14) . ?
C26 F1 1.339(15) . ?
C26 F2 1.342(15) . ?
C26 S1 1.814(14) . ?
N1 H1 0.8800 . ?
N2 Re1 2.237(10) . ?
N3 Re1 2.181(11) . ?
N4 Re1 2.162(10) . ?
O5 S1 1.451(9) . ?
O6 S1 1.433(9) . ?
O7 S1 1.442(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.6(12) . . ?
C2 C1 N1 121.7(12) . . ?
C6 C1 N1 116.7(11) . . ?
C1 C2 C3 118.2(13) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 121.7(12) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 118.8(12) . . ?
C5 C4 I1 118.6(10) . . ?
C3 C4 I1 122.6(10) . . ?
C4 C5 C6 120.7(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.7(12) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O1 C7 N1 125.6(11) . . ?
O1 C7 C8 121.5(12) . . ?
N1 C7 C8 112.8(10) . . ?
C12 C8 C9 119.5(10) . . ?
C12 C8 C7 117.6(10) . . ?
C9 C8 C7 122.9(10) . . ?
C10 C9 C8 116.6(10) . . ?
C10 C9 H9 121.7 . . ?
C8 C9 H9 121.7 . . ?
C11 C10 C9 121.6(11) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
N2 C11 C10 121.9(11) . . ?
N2 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
N2 C12 C8 121.8(11) . . ?
N2 C12 H12 119.1 . . ?
C8 C12 H12 119.1 . . ?
N3 C13 C14 122.0(12) . . ?
N3 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 119.7(12) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 118.8(13) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 119.5(11) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
N3 C17 C16 121.5(11) . . ?
N3 C17 C18 114.3(11) . . ?
C16 C17 C18 124.1(11) . . ?
N4 C18 C19 122.5(11) . . ?
N4 C18 C17 116.2(11) . . ?
C19 C18 C17 121.2(12) . . ?
C18 C19 C20 119.0(13) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 118.9(12) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 118.6(12) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
N4 C22 C21 123.8(13) . . ?
N4 C22 H22 118.1 . . ?
C21 C22 H22 118.1 . . ?
O2 C23 Re1 179.6(13) . . ?
O3 C24 Re1 176.3(12) . . ?
O4 C25 Re1 178.2(11) . . ?
F3 C26 F1 107.2(11) . . ?
F3 C26 F2 108.0(11) . . ?
F1 C26 F2 105.3(11) . . ?
F3 C26 S1 112.5(10) . . ?
F1 C26 S1 111.4(9) . . ?
F2 C26 S1 112.1(9) . . ?
C7 N1 C1 125.6(11) . . ?
C7 N1 H1 117.2 . . ?
C1 N1 H1 117.2 . . ?
C11 N2 C12 118.5(10) . . ?
C11 N2 Re1 119.0(7) . . ?
C12 N2 Re1 122.2(8) . . ?
C17 N3 C13 118.3(12) . . ?
C17 N3 Re1 117.5(8) . . ?
C13 N3 Re1 124.2(9) . . ?
C22 N4 C18 117.2(11) . . ?
C22 N4 Re1 125.7(9) . . ?
C18 N4 Re1 117.1(8) . . ?
C25 Re1 C23 91.0(5) . . ?
C25 Re1 C24 92.1(6) . . ?
C23 Re1 C24 85.5(5) . . ?
C25 Re1 N4 88.5(4) . . ?
C23 Re1 N4 174.4(4) . . ?
C24 Re1 N4 100.1(4) . . ?
C25 Re1 N3 91.9(5) . . ?
C23 Re1 N3 99.6(5) . . ?
C24 Re1 N3 173.4(5) . . ?
N4 Re1 N3 74.8(4) . . ?
C25 Re1 N2 172.8(4) . . ?
C23 Re1 N2 96.1(4) . . ?
C24 Re1 N2 89.2(5) . . ?
N4 Re1 N2 84.4(3) . . ?
N3 Re1 N2 86.2(4) . . ?
O6 S1 O7 114.7(6) . . ?
O6 S1 O5 115.2(6) . . ?
O7 S1 O5 114.4(5) . . ?
O6 S1 C26 103.1(6) . . ?
O7 S1 C26 102.6(6) . . ?
O5 S1 C26 104.7(6) . . ?

_refine_diff_density_max         1.506
_refine_diff_density_min         -1.991
_refine_diff_density_rms         0.209

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 893639'
#######################################################################
#
#                 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_sjp1012

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C58 H48 F6 N10 O15 Re2 S2'
_chemical_formula_sum            'C58 H48 F6 N10 O15 Re2 S2'
_chemical_formula_weight         1675.58

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   11.4748(7)
_cell_length_b                   26.9371(18)
_cell_length_c                   23.6378(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.295(3)
_cell_angle_gamma                90.00
_cell_volume                     7262.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    6716
_cell_measurement_theta_min      1.15
_cell_measurement_theta_max      26.64

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3288
_exptl_absorpt_coefficient_mu    3.467
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2760
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21545
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_sigmaI/netI    0.2664
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         26.64
_reflns_number_total             13633
_reflns_number_gt                6716
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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           fullcycle
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1362P)²+12.6525P] 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         13633
_refine_ls_number_parameters     867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1783
_refine_ls_R_factor_gt           0.0897
_refine_ls_wR_factor_ref         0.2757
_refine_ls_wR_factor_gt          0.2165
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

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 0.6356(14) 0.0297(6) 0.1344(7) 0.034(4) Uani 1 1 d . . .
C2 C 0.6203(14) -0.0217(6) 0.1330(8) 0.041(4) Uani 1 1 d . . .
H2 H 0.5962 -0.0377 0.0978 0.049 Uiso 1 1 calc R . .
C3 C 0.6392(16) -0.0491(7) 0.1808(8) 0.052(5) Uani 1 1 d . . .
H3 H 0.6307 -0.0842 0.1786 0.062 Uiso 1 1 calc R . .
C4 C 0.6711(16) -0.0269(7) 0.2336(8) 0.048(5) Uani 1 1 d . . .
C5 C 0.6854(15) 0.0238(7) 0.2342(8) 0.048(5) Uani 1 1 d . . .
H5 H 0.7091 0.0395 0.2696 0.058 Uiso 1 1 calc R . .
C6 C 0.6674(14) 0.0529(6) 0.1866(7) 0.039(4) Uani 1 1 d . . .
H6 H 0.6763 0.0879 0.1890 0.047 Uiso 1 1 calc R . .
C7 C 0.6888(19) -0.0570(8) 0.2878(9) 0.066(6) Uani 1 1 d . . .
H7A H 0.6750 -0.0922 0.2789 0.100 Uiso 1 1 calc R . .
H7B H 0.6335 -0.0458 0.3139 0.100 Uiso 1 1 calc R . .
H7C H 0.7692 -0.0526 0.3057 0.100 Uiso 1 1 calc R . .
C8 C 0.5911(14) 0.1030(6) 0.0727(8) 0.039(4) Uani 1 1 d . . .
C9 C 0.5824(13) 0.1208(6) 0.0120(7) 0.032(4) Uani 1 1 d . . .
C10 C 0.5980(14) 0.0927(6) -0.0351(7) 0.038(4) Uani 1 1 d . . .
H10 H 0.6170 0.0585 -0.0312 0.046 Uiso 1 1 calc R . .
C11 C 0.5860(13) 0.1143(6) -0.0876(7) 0.037(4) Uani 1 1 d . . .
H11 H 0.5963 0.0951 -0.1204 0.044 Uiso 1 1 calc R . .
C12 C 0.5596(13) 0.1627(6) -0.0931(7) 0.033(4) Uani 1 1 d . . .
H12 H 0.5559 0.1775 -0.1297 0.039 Uiso 1 1 calc R . .
C13 C 0.5522(13) 0.1706(6) 0.0022(7) 0.035(4) Uani 1 1 d . . .
H13 H 0.5412 0.1907 0.0342 0.042 Uiso 1 1 calc R . .
C14 C 0.3381(16) 0.2268(6) -0.1680(8) 0.043(4) Uani 1 1 d . . .
H14 H 0.3992 0.2396 -0.1878 0.051 Uiso 1 1 calc R . .
C15 C 0.2541(16) 0.1988(7) -0.1972(8) 0.051(5) Uani 1 1 d . . .
H15 H 0.2574 0.1924 -0.2365 0.061 Uiso 1 1 calc R . .
C16 C 0.1635(16) 0.1795(7) -0.1702(8) 0.048(5) Uani 1 1 d . . .
H16 H 0.1047 0.1592 -0.1898 0.058 Uiso 1 1 calc R . .
C17 C 0.1623(16) 0.1913(6) -0.1127(8) 0.046(5) Uani 1 1 d . . .
H17 H 0.1001 0.1798 -0.0927 0.055 Uiso 1 1 calc R . .
C18 C 0.2508(15) 0.2197(6) -0.0847(7) 0.040(4) Uani 1 1 d . . .
C19 C 0.2558(16) 0.2332(6) -0.0247(8) 0.044(4) Uani 1 1 d . . .
C20 C 0.1629(17) 0.2246(7) 0.0091(8) 0.051(5) Uani 1 1 d . . .
H20 H 0.0930 0.2083 -0.0061 0.061 Uiso 1 1 calc R . .
C21 C 0.1777(17) 0.2411(7) 0.0650(8) 0.048(5) Uani 1 1 d . . .
H21 H 0.1167 0.2364 0.0886 0.058 Uiso 1 1 calc R . .
C22 C 0.2777(17) 0.2635(7) 0.0861(9) 0.051(5) Uani 1 1 d . . .
H22 H 0.2879 0.2749 0.1243 0.062 Uiso 1 1 calc R . .
C23 C 0.3628(16) 0.2693(6) 0.0521(8) 0.043(4) Uani 1 1 d . . .
H23 H 0.4333 0.2849 0.0679 0.051 Uiso 1 1 calc R . .
C24 C 0.6135(18) 0.2920(7) -0.0037(9) 0.053(5) Uani 1 1 d . . .
C25 C 0.5911(14) 0.2815(6) -0.1159(7) 0.033(4) Uani 1 1 d . . .
C26 C 0.4353(16) 0.3378(7) -0.0671(8) 0.043(4) Uani 1 1 d . . .
C27 C -0.1185(15) 0.1249(6) -0.0353(7) 0.040(4) Uani 1 1 d . . .
C28 C -0.1403(14) 0.1750(6) -0.0336(8) 0.041(4) Uani 1 1 d . . .
H28 H -0.1492 0.1912 0.0014 0.049 Uiso 1 1 calc R . .
C29 C -0.1492(15) 0.2018(7) -0.0857(8) 0.045(5) Uani 1 1 d . . .
H29 H -0.1615 0.2366 -0.0849 0.054 Uiso 1 1 calc R . .
C30 C -0.1405(15) 0.1793(6) -0.1370(8) 0.042(4) Uani 1 1 d . . .
C31 C -0.1233(15) 0.1287(7) -0.1367(8) 0.044(4) Uani 1 1 d . . .
H31 H -0.1178 0.1121 -0.1717 0.053 Uiso 1 1 calc R . .
C32 C -0.1139(14) 0.1024(6) -0.0887(7) 0.038(4) Uani 1 1 d . . .
H32 H -0.1039 0.0675 -0.0906 0.045 Uiso 1 1 calc R . .
C33 C -0.1505(18) 0.2087(7) -0.1904(8) 0.060(5) Uani 1 1 d . . .
H33A H -0.1429 0.1866 -0.2227 0.090 Uiso 1 1 calc R . .
H33B H -0.0881 0.2337 -0.1881 0.090 Uiso 1 1 calc R . .
H33C H -0.2270 0.2253 -0.1956 0.090 Uiso 1 1 calc R . .
C34 C -0.0955(15) 0.1075(7) 0.0686(8) 0.042(4) Uani 1 1 d . . .
C35 C -0.0708(14) 0.0678(6) 0.1116(7) 0.038(4) Uani 1 1 d . . .
C36 C -0.0958(14) 0.0151(6) 0.1020(8) 0.041(4) Uani 1 1 d . . .
H36 H -0.1249 0.0031 0.0653 0.049 Uiso 1 1 calc R . .
C37 C -0.0761(14) -0.0162(6) 0.1470(7) 0.037(4) Uani 1 1 d . . .
H37 H -0.0951 -0.0504 0.1423 0.044 Uiso 1 1 calc R . .
C38 C -0.0307(13) 0.0002(6) 0.1977(7) 0.032(4) Uani 1 1 d . . .
H38 H -0.0147 -0.0232 0.2276 0.038 Uiso 1 1 calc R . .
C39 C -0.0270(13) 0.0809(6) 0.1654(7) 0.029(4) Uani 1 1 d . . .
C40 C 0.1920(14) 0.1599(6) 0.2350(7) 0.036(4) Uani 1 1 d . . .
H40 H 0.1300 0.1787 0.2478 0.043 Uiso 1 1 calc R . .
C41 C 0.2707(14) 0.1830(6) 0.2059(7) 0.036(4) Uani 1 1 d . . .
H41 H 0.2637 0.2176 0.1982 0.043 Uiso 1 1 calc R . .
C42 C 0.3616(16) 0.1562(7) 0.1876(8) 0.048(5) Uani 1 1 d . . .
H42 H 0.4181 0.1718 0.1670 0.058 Uiso 1 1 calc R . .
C43 C 0.3689(16) 0.1065(7) 0.1997(7) 0.045(4) Uani 1 1 d . . .
H43 H 0.4310 0.0873 0.1876 0.054 Uiso 1 1 calc R . .
C44 C 0.2851(14) 0.0839(6) 0.2298(7) 0.036(4) Uani 1 1 d . . .
C45 C 0.2865(14) 0.0315(6) 0.2453(7) 0.037(4) Uani 1 1 d . . .
C46 C 0.3679(16) -0.0020(7) 0.2295(8) 0.046(5) Uani 1 1 d . . .
H46 H 0.4268 0.0085 0.2069 0.056 Uiso 1 1 calc R . .
C47 C 0.3630(17) -0.0524(7) 0.2472(8) 0.053(5) Uani 1 1 d . . .
H47 H 0.4139 -0.0768 0.2345 0.064 Uiso 1 1 calc R . .
C48 C 0.2827(16) -0.0639(7) 0.2829(8) 0.050(5) Uani 1 1 d . . .
H48 H 0.2801 -0.0966 0.2978 0.061 Uiso 1 1 calc R . .
C49 C 0.2058(16) -0.0291(7) 0.2976(8) 0.050(5) Uani 1 1 d . . .
H49 H 0.1496 -0.0386 0.3222 0.060 Uiso 1 1 calc R . .
C50 C -0.0405(17) 0.1248(7) 0.2961(8) 0.047(5) Uani 1 1 d . . .
C51 C -0.0271(16) 0.0327(7) 0.3330(8) 0.048(5) Uani 1 1 d . . .
C52 C 0.1491(15) 0.0946(6) 0.3679(8) 0.038(4) Uani 1 1 d . . .
C53 C 0.2298(16) 0.0982(7) 0.0394(8) 0.048(5) Uani 1 1 d . . .
C54 C 0.5556(19) -0.1774(8) 0.3478(9) 0.061(6) Uani 1 1 d . . .
C55 C 0.641(2) 0.2384(8) 0.1697(9) 0.062(6) Uani 1 1 d . . .
C56 C 0.745(2) 0.2070(9) 0.1786(11) 0.086(7) Uani 1 1 d . . .
H56A H 0.7231 0.1747 0.1935 0.129 Uiso 1 1 calc R . .
H56B H 0.8035 0.2228 0.2060 0.129 Uiso 1 1 calc R . .
H56C H 0.7773 0.2022 0.1424 0.129 Uiso 1 1 calc R . .
C57 C 0.969(4) -0.1163(16) 0.3193(18) 0.118(13) Uani 1 1 d . . .
C58 C 0.941(3) -0.1174(11) 0.3816(13) 0.118(10) Uani 1 1 d . . .
H58A H 1.0134 -0.1152 0.4074 0.177 Uiso 1 1 calc R . .
H58B H 0.9001 -0.1484 0.3887 0.177 Uiso 1 1 calc R . .
H58C H 0.8899 -0.0892 0.3883 0.177 Uiso 1 1 calc R . .
N1 N 0.6199(10) 0.0541(5) 0.0814(6) 0.033(3) Uani 1 1 d . . .
H1 H 0.6295 0.0362 0.0511 0.039 Uiso 1 1 calc R . .
N2 N 0.5379(11) 0.1914(5) -0.0481(6) 0.031(3) Uani 1 1 d . . .
N3 N 0.3394(11) 0.2371(5) -0.1126(6) 0.034(3) Uani 1 1 d . . .
N4 N 0.3563(13) 0.2554(5) -0.0009(6) 0.042(4) Uani 1 1 d . . .
N5 N -0.1050(11) 0.0938(5) 0.0128(6) 0.038(3) Uani 1 1 d . . .
H5A H -0.1022 0.0618 0.0060 0.046 Uiso 1 1 calc R . .
N6 N -0.0060(11) 0.0487(5) 0.2090(6) 0.036(3) Uani 1 1 d . . .
N7 N 0.1984(11) 0.1110(4) 0.2464(6) 0.033(3) Uani 1 1 d . . .
N8 N 0.2050(11) 0.0181(5) 0.2791(6) 0.036(3) Uani 1 1 d . . .
N9 N 0.5606(18) 0.2614(8) 0.1657(10) 0.091(7) Uani 1 1 d . . .
N10 N 0.988(3) -0.1148(13) 0.2784(17) 0.140(14) Uani 1 1 d . . .
O1 O 0.5782(10) 0.1323(4) 0.1116(5) 0.044(3) Uani 1 1 d . . .
O2 O 0.6892(13) 0.3030(6) 0.0275(6) 0.070(4) Uani 1 1 d . . .
O3 O 0.6520(11) 0.2887(4) -0.1496(5) 0.048(3) Uani 1 1 d . . .
O4 O 0.4026(12) 0.3782(5) -0.0733(6) 0.064(4) Uani 1 1 d . . .
O5 O -0.0988(12) 0.1501(4) 0.0845(5) 0.054(3) Uani 1 1 d . . .
O6 O -0.1124(11) 0.1546(5) 0.2960(6) 0.054(3) Uani 1 1 d . . .
O7 O -0.0873(12) 0.0074(5) 0.3566(6) 0.061(4) Uani 1 1 d . . .
O8 O 0.1929(12) 0.1057(5) 0.4105(6) 0.060(4) Uani 1 1 d . . .
O9 O 0.3317(11) 0.0234(4) 0.0024(6) 0.057(4) Uani 1 1 d . . .
O10 O 0.1393(11) 0.0126(4) 0.0335(5) 0.056(3) Uani 1 1 d . . .
O11 O 0.3092(13) 0.0258(5) 0.1023(6) 0.069(4) Uani 1 1 d . . .
O12 O 0.4808(11) -0.1613(4) 0.2446(5) 0.053(3) Uani 1 1 d . . .
O13 O 0.3468(11) -0.1929(5) 0.3078(5) 0.058(4) Uani 1 1 d . . .
O14 O 0.4956(10) -0.2461(4) 0.2763(6) 0.051(3) Uani 1 1 d . . .
Re1 Re 0.48616(6) 0.27063(3) -0.05938(3) 0.0372(2) Uani 1 1 d . . .
Re2 Re 0.07359(6) 0.07275(2) 0.29374(3) 0.0357(2) Uani 1 1 d . . .
S1 S 0.2549(4) 0.03381(17) 0.04540(19) 0.0415(11) Uani 1 1 d . . .
S2 S 0.4599(4) -0.19619(16) 0.28668(19) 0.0383(10) Uani 1 1 d . . .
F1 F 0.1624(9) 0.1156(4) 0.0776(5) 0.064(3) Uani 1 1 d . . .
F2 F 0.1759(10) 0.1100(4) -0.0125(5) 0.066(3) Uani 1 1 d . . .
F3 F 0.3289(8) 0.1249(4) 0.0461(5) 0.063(3) Uani 1 1 d . . .
F4 F 0.5311(11) -0.1315(5) 0.3650(5) 0.079(4) Uani 1 1 d . . .
F5 F 0.6696(9) -0.1758(4) 0.3356(5) 0.062(3) Uani 1 1 d . . .
F6 F 0.5547(10) -0.2089(5) 0.3918(5) 0.084(4) Uani 1 1 d . . .
O15 O 0.264(6) -0.100(2) 0.446(3) 0.09(2) Uani 0.25 1 d P . .
O16 O -0.055(5) -0.017(2) 0.493(2) 0.073(17) Uani 0.25 1 d P . .
O17 O -0.424(5) 0.168(2) 0.338(2) 0.073(17) Uani 0.25 1 d P . .
O18 O 0.535(3) 0.0909(15) 0.3732(17) 0.033(10) Uani 0.25 1 d P . .


_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
C1 C6 1.39(2) . ?
C1 C2 1.40(2) . ?
C1 N1 1.408(19) . ?
C2 C3 1.35(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.40(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.38(2) . ?
C4 C7 1.51(3) . ?
C5 C6 1.37(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O1 1.231(19) . ?
C8 N1 1.37(2) . ?
C8 C9 1.50(2) . ?
C9 C10 1.38(2) . ?
C9 C13 1.40(2) . ?
C10 C11 1.36(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.34(2) . ?
C11 H11 0.9500 . ?
C12 N2 1.358(19) . ?
C12 H12 0.9500 . ?
C13 N2 1.309(19) . ?
C13 H13 0.9500 . ?
C14 N3 1.34(2) . ?
C14 C15 1.35(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.38(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.40(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.38(2) . ?
C17 H17 0.9500 . ?
C18 N3 1.36(2) . ?
C18 C19 1.46(2) . ?
C19 N4 1.37(2) . ?
C19 C20 1.42(2) . ?
C20 C21 1.39(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.34(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.34(2) . ?
C22 H22 0.9500 . ?
C23 N4 1.30(2) . ?
C23 H23 0.9500 . ?
C24 O2 1.12(2) . ?
C24 Re1 1.94(2) . ?
C25 O3 1.133(18) . ?
C25 Re1 1.917(17) . ?
C26 O4 1.16(2) . ?
C26 Re1 1.902(19) . ?
C27 C28 1.37(2) . ?
C27 C32 1.40(2) . ?
C27 N5 1.41(2) . ?
C28 C29 1.42(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.37(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.38(2) . ?
C30 C33 1.48(2) . ?
C31 C32 1.33(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 O5 1.210(19) . ?
C34 N5 1.36(2) . ?
C34 C35 1.48(2) . ?
C35 C39 1.36(2) . ?
C35 C36 1.46(2) . ?
C36 C37 1.36(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.33(2) . ?
C37 H37 0.9500 . ?
C38 N6 1.356(19) . ?
C38 H38 0.9500 . ?
C39 N6 1.350(19) . ?
C40 C41 1.35(2) . ?
C40 N7 1.346(19) . ?
C40 H40 0.9500 . ?
C41 C42 1.38(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.37(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.40(2) . ?
C43 H43 0.9500 . ?
C44 N7 1.327(19) . ?
C44 C45 1.46(2) . ?
C45 N8 1.34(2) . ?
C45 C46 1.38(2) . ?
C46 C47 1.42(2) . ?
C46 H46 0.9500 . ?
C47 C48 1.35(2) . ?
C47 H47 0.9500 . ?
C48 C49 1.36(2) . ?
C48 H48 0.9500 . ?
C49 N8 1.34(2) . ?
C49 H49 0.9500 . ?
C50 O6 1.15(2) . ?
C50 Re2 1.92(2) . ?
C51 O7 1.16(2) . ?
C51 Re2 1.90(2) . ?
C52 O8 1.116(19) . ?
C52 Re2 1.958(19) . ?
C53 F1 1.34(2) . ?
C53 F3 1.34(2) . ?
C53 F2 1.35(2) . ?
C53 S1 1.760(19) . ?
C54 F4 1.34(2) . ?
C54 F6 1.34(2) . ?
C54 F5 1.37(2) . ?
C54 S2 1.79(2) . ?
C55 N9 1.11(3) . ?
C55 C56 1.45(3) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 N10 1.01(4) . ?
C57 C58 1.55(4) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
N1 H1 0.8800 . ?
N2 Re1 2.223(13) . ?
N3 Re1 2.184(12) . ?
N4 Re1 2.180(14) . ?
N5 H5A 0.8800 . ?
N6 Re2 2.205(13) . ?
N7 Re2 2.171(13) . ?
N8 Re2 2.162(12) . ?
O9 S1 1.443(13) . ?
O10 S1 1.443(13) . ?
O11 S1 1.434(14) . ?
O12 S2 1.407(12) . ?
O13 S2 1.443(13) . ?
O14 S2 1.434(12) . ?
O16 O16 1.56(11) 3_556 ?

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
C6 C1 C2 119.0(16) . . ?
C6 C1 N1 125.0(15) . . ?
C2 C1 N1 116.0(15) . . ?
C3 C2 C1 121.0(17) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.1(18) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.1(18) . . ?
C5 C4 C7 121.2(18) . . ?
C3 C4 C7 121.7(17) . . ?
C6 C5 C4 123.5(18) . . ?
C6 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C5 C6 C1 118.3(16) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 123.4(16) . . ?
O1 C8 C9 120.5(15) . . ?
N1 C8 C9 116.0(15) . . ?
C10 C9 C13 116.4(15) . . ?
C10 C9 C8 126.7(15) . . ?
C13 C9 C8 116.9(14) . . ?
C11 C10 C9 119.6(16) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.0(16) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 N2 122.4(16) . . ?
C11 C12 H12 118.8 . . ?
N2 C12 H12 118.8 . . ?
N2 C13 C9 124.5(15) . . ?
N2 C13 H13 117.8 . . ?
C9 C13 H13 117.8 . . ?
N3 C14 C15 123.2(17) . . ?
N3 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C14 C15 C16 120.3(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 116.9(18) . . ?
C15 C16 H16 121.5 . . ?
C17 C16 H16 121.5 . . ?
C18 C17 C16 120.4(18) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
N3 C18 C17 120.7(16) . . ?
N3 C18 C19 115.8(15) . . ?
C17 C18 C19 123.5(17) . . ?
N4 C19 C20 119.5(17) . . ?
N4 C19 C18 116.8(16) . . ?
C20 C19 C18 123.7(17) . . ?
C21 C20 C19 117.6(18) . . ?
C21 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
C22 C21 C20 120.5(19) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 118.6(19) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
N4 C23 C22 125.0(18) . . ?
N4 C23 H23 117.5 . . ?
C22 C23 H23 117.5 . . ?
O2 C24 Re1 177.4(19) . . ?
O3 C25 Re1 178.7(15) . . ?
O4 C26 Re1 178.0(17) . . ?
C28 C27 C32 118.4(16) . . ?
C28 C27 N5 124.3(16) . . ?
C32 C27 N5 117.3(15) . . ?
C27 C28 C29 117.9(17) . . ?
C27 C28 H28 121.0 . . ?
C29 C28 H28 121.0 . . ?
C30 C29 C28 122.5(17) . . ?
C30 C29 H29 118.7 . . ?
C28 C29 H29 118.7 . . ?
C29 C30 C31 117.2(17) . . ?
C29 C30 C33 120.6(16) . . ?
C31 C30 C33 122.1(17) . . ?
C32 C31 C30 122.0(17) . . ?
C32 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
C31 C32 C27 121.9(16) . . ?
C31 C32 H32 119.1 . . ?
C27 C32 H32 119.1 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O5 C34 N5 123.7(16) . . ?
O5 C34 C35 118.8(16) . . ?
N5 C34 C35 117.4(15) . . ?
C39 C35 C36 116.3(15) . . ?
C39 C35 C34 118.6(15) . . ?
C36 C35 C34 125.0(15) . . ?
C37 C36 C35 117.9(16) . . ?
C37 C36 H36 121.1 . . ?
C35 C36 H36 121.1 . . ?
C38 C37 C36 121.1(16) . . ?
C38 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
C37 C38 N6 123.4(16) . . ?
C37 C38 H38 118.3 . . ?
N6 C38 H38 118.3 . . ?
N6 C39 C35 124.3(14) . . ?
C41 C40 N7 122.1(15) . . ?
C41 C40 H40 119.0 . . ?
N7 C40 H40 119.0 . . ?
C40 C41 C42 119.4(16) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
C43 C42 C41 118.6(17) . . ?
C43 C42 H42 120.7 . . ?
C41 C42 H42 120.7 . . ?
C42 C43 C44 120.1(17) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
N7 C44 C43 119.5(15) . . ?
N7 C44 C45 116.5(14) . . ?
C43 C44 C45 124.0(15) . . ?
N8 C45 C46 121.5(16) . . ?
N8 C45 C44 114.8(14) . . ?
C46 C45 C44 123.7(16) . . ?
C45 C46 C47 119.6(17) . . ?
C45 C46 H46 120.2 . . ?
C47 C46 H46 120.2 . . ?
C48 C47 C46 117.0(18) . . ?
C48 C47 H47 121.5 . . ?
C46 C47 H47 121.5 . . ?
C47 C48 C49 120.4(19) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
N8 C49 C48 123.4(18) . . ?
N8 C49 H49 118.3 . . ?
C48 C49 H49 118.3 . . ?
O6 C50 Re2 176.9(17) . . ?
O7 C51 Re2 178.6(17) . . ?
O8 C52 Re2 178.1(16) . . ?
F1 C53 F3 106.1(14) . . ?
F1 C53 F2 106.8(15) . . ?
F3 C53 F2 106.1(15) . . ?
F1 C53 S1 113.2(13) . . ?
F3 C53 S1 113.0(13) . . ?
F2 C53 S1 111.1(13) . . ?
F4 C54 F6 109.1(18) . . ?
F4 C54 F5 105.8(17) . . ?
F6 C54 F5 105.8(16) . . ?
F4 C54 S2 112.0(15) . . ?
F6 C54 S2 113.0(14) . . ?
F5 C54 S2 110.7(14) . . ?
N9 C55 C56 176(3) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
N10 C57 C58 179(6) . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C8 N1 C1 126.0(14) . . ?
C8 N1 H1 117.0 . . ?
C1 N1 H1 117.0 . . ?
C13 N2 C12 116.9(14) . . ?
C13 N2 Re1 121.7(10) . . ?
C12 N2 Re1 121.4(11) . . ?
C14 N3 C18 118.4(14) . . ?
C14 N3 Re1 125.2(11) . . ?
C18 N3 Re1 115.8(11) . . ?
C23 N4 C19 118.7(15) . . ?
C23 N4 Re1 125.8(13) . . ?
C19 N4 Re1 115.2(12) . . ?
C34 N5 C27 127.8(14) . . ?
C34 N5 H5A 116.1 . . ?
C27 N5 H5A 116.1 . . ?
C39 N6 C38 116.9(13) . . ?
C39 N6 Re2 121.8(10) . . ?
C38 N6 Re2 121.3(11) . . ?
C44 N7 C40 120.3(14) . . ?
C44 N7 Re2 116.7(10) . . ?
C40 N7 Re2 123.0(11) . . ?
C45 N8 C49 117.8(14) . . ?
C45 N8 Re2 117.1(11) . . ?
C49 N8 Re2 124.9(12) . . ?
C26 Re1 C25 89.9(7) . . ?
C26 Re1 C24 89.0(8) . . ?
C25 Re1 C24 86.8(7) . . ?
C26 Re1 N4 90.9(6) . . ?
C25 Re1 N4 175.0(6) . . ?
C24 Re1 N4 98.1(7) . . ?
C26 Re1 N3 97.4(6) . . ?
C25 Re1 N3 99.5(6) . . ?
C24 Re1 N3 171.0(7) . . ?
N4 Re1 N3 75.5(5) . . ?
C26 Re1 N2 177.2(6) . . ?
C25 Re1 N2 92.9(6) . . ?
C24 Re1 N2 91.9(7) . . ?
N4 Re1 N2 86.3(5) . . ?
N3 Re1 N2 81.5(5) . . ?
C51 Re2 C50 87.0(8) . . ?
C51 Re2 C52 88.1(7) . . ?
C50 Re2 C52 89.5(7) . . ?
C51 Re2 N8 99.4(7) . . ?
C50 Re2 N8 171.8(7) . . ?
C52 Re2 N8 95.7(6) . . ?
C51 Re2 N7 173.6(6) . . ?
C50 Re2 N7 99.1(6) . . ?
C52 Re2 N7 93.8(6) . . ?
N8 Re2 N7 74.3(5) . . ?
C51 Re2 N6 93.6(7) . . ?
C50 Re2 N6 91.4(6) . . ?
C52 Re2 N6 178.1(6) . . ?
N8 Re2 N6 83.2(5) . . ?
N7 Re2 N6 84.4(5) . . ?
O11 S1 O9 113.2(9) . . ?
O11 S1 O10 114.7(8) . . ?
O9 S1 O10 113.9(8) . . ?
O11 S1 C53 105.9(9) . . ?
O9 S1 C53 104.0(8) . . ?
O10 S1 C53 103.7(8) . . ?
O12 S2 O14 115.5(8) . . ?
O12 S2 O13 115.7(8) . . ?
O14 S2 O13 113.7(8) . . ?
O12 S2 C54 104.2(9) . . ?
O14 S2 C54 104.0(9) . . ?
O13 S2 C54 101.5(9) . . ?

_diffrn_measured_fraction_theta_max 0.893
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         1.707
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.304
_database_code_depnum_ccdc_archive 'CCDC 893640'
#######################################################################
#
#                 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_sjp1015
#TrackingRef 'Re-pMe-b_sjp1015.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H42 F6 N8 O15 Re2 S2'
_chemical_formula_sum            'C54 H42 F6 N8 O15 Re2 S2'
_chemical_formula_weight         1593.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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   P21/a

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

_cell_length_a                   12.1162(10)
_cell_length_b                   27.444(3)
_cell_length_c                   19.0654(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.666(4)
_cell_angle_gamma                90.00
_cell_volume                     6249.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3250
_cell_measurement_theta_min      1.31
_cell_measurement_theta_max      25.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3112
_exptl_absorpt_coefficient_mu    4.024
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4328
_exptl_absorpt_correction_T_max  0.9239
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15847
_diffrn_reflns_av_R_equivalents  0.1321
_diffrn_reflns_av_sigmaI/netI    364.0409
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.24
_reflns_number_total             11064
_reflns_number_gt                3250
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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           fullcycle
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0383P)²+397.8285P] 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         11064
_refine_ls_number_parameters     723
_refine_ls_number_restraints     340
_refine_ls_R_factor_all          0.2588
_refine_ls_R_factor_gt           0.1206
_refine_ls_wR_factor_ref         0.2559
_refine_ls_wR_factor_gt          0.2300
_refine_ls_goodness_of_fit_ref   0.775
_refine_ls_restrained_S_all      0.767
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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
N1 N 0.1154(7) 0.1649(4) 0.4905(7) 0.036(5) Uani 1 1 d . . .
H1 H 0.1263 0.1943 0.5089 0.043 Uiso 1 1 calc R . .
C1 C 0.1210(7) 0.1587(4) 0.4152(7) 0.057(8) Uani 1 1 d R . .
C2 C 0.1458(7) 0.1152(4) 0.3838(7) 0.064(8) Uani 1 1 d R . .
H2 H 0.1529 0.0859 0.4106 0.077 Uiso 1 1 calc R . .
C3 C 0.1603(7) 0.1147(4) 0.3130(7) 0.051(7) Uani 1 1 d R . .
H3 H 0.1773 0.0850 0.2915 0.061 Uiso 1 1 calc R . .
C4 C 0.1500(7) 0.1576(4) 0.2737(7) 0.061(8) Uani 1 1 d R . .
C5 C 0.1252(7) 0.2010(4) 0.3051(7) 0.062(8) Uani 1 1 d R . .
H5 H 0.1181 0.2303 0.2783 0.074 Uiso 1 1 calc R . .
C6 C 0.1107(7) 0.2016(4) 0.3759(7) 0.054(8) Uani 1 1 d R . .
H6 H 0.0937 0.2312 0.3974 0.065 Uiso 1 1 calc R . .
C7 C 0.169(2) 0.1562(10) 0.1958(15) 0.070(9) Uani 1 1 d . . .
H7A H 0.1586 0.1890 0.1753 0.106 Uiso 1 1 calc R . .
H7B H 0.1147 0.1339 0.1685 0.106 Uiso 1 1 calc R . .
H7C H 0.2450 0.1449 0.1940 0.106 Uiso 1 1 calc R . .
C8 C 0.0945(5) 0.1280(2) 0.5334(4) 0.034(6) Uani 1 1 d . . .
C9 C 0.0835(5) 0.1427(2) 0.6073(4) 0.047(7) Uani 1 1 d R . .
C10 C 0.1052(5) 0.1884(2) 0.6379(4) 0.059(8) Uani 1 1 d R . .
H10 H 0.1311 0.2140 0.6113 0.071 Uiso 1 1 calc R . .
C11 C 0.0891(5) 0.1966(2) 0.7074(4) 0.060(8) Uani 1 1 d R . .
H11 H 0.1040 0.2279 0.7283 0.072 Uiso 1 1 calc R . .
C12 C 0.0513(5) 0.1592(2) 0.7463(4) 0.043(6) Uani 1 1 d R . .
H12 H 0.0403 0.1648 0.7938 0.051 Uiso 1 1 calc R . .
N2 N 0.0295(5) 0.1135(2) 0.7158(4) 0.041(5) Uani 1 1 d R . .
C13 C 0.0456(5) 0.1052(2) 0.6463(4) 0.025(5) Uani 1 1 d R . .
H13 H 0.0308 0.0740 0.6254 0.029 Uiso 1 1 calc R . .
N3 N -0.1612(5) 0.1079(2) 0.7974(4) 0.053(6) Uani 1 1 d R . .
C14 C -0.2631(5) 0.1194(2) 0.7554(4) 0.052(7) Uani 1 1 d R . .
H14 H -0.2847 0.1039 0.7107 0.063 Uiso 1 1 calc R . .
C15 C -0.3332(5) 0.1537(2) 0.7788(4) 0.075(9) Uani 1 1 d R . .
H15 H -0.4028 0.1615 0.7500 0.090 Uiso 1 1 calc R . .
C16 C -0.3016(5) 0.1764(2) 0.8442(4) 0.058(8) Uani 1 1 d R . .
H16 H -0.3495 0.1998 0.8602 0.070 Uiso 1 1 calc R . .
C17 C -0.1997(5) 0.1650(2) 0.8862(4) 0.070(9) Uani 1 1 d R . .
H17 H -0.1781 0.1805 0.9309 0.085 Uiso 1 1 calc R . .
C18 C -0.1295(5) 0.1307(2) 0.8628(4) 0.033(6) Uani 1 1 d R . .
C19 C -0.0232(5) 0.1177(2) 0.9034(4) 0.043(7) Uani 1 1 d R . .
C20 C 0.0244(5) 0.1363(2) 0.9694(4) 0.072(9) Uani 1 1 d R . .
H20 H -0.0157 0.1593 0.9927 0.087 Uiso 1 1 calc R . .
C21 C 0.1306(5) 0.1213(2) 1.0014(4) 0.069(9) Uani 1 1 d R . .
H21 H 0.1631 0.1340 1.0465 0.083 Uiso 1 1 calc R . .
C22 C 0.1892(5) 0.0877(2) 0.9674(4) 0.083(10) Uani 1 1 d R . .
H22 H 0.2617 0.0774 0.9892 0.100 Uiso 1 1 calc R . .
C23 C 0.1416(5) 0.0690(2) 0.9014(4) 0.060(8) Uani 1 1 d R . .
H23 H 0.1817 0.0460 0.8781 0.072 Uiso 1 1 calc R . .
N4 N 0.0355(5) 0.0840(2) 0.8694(4) 0.070(7) Uani 1 1 d R . .
C24 C 0.066(3) 0.0132(12) 0.7576(18) 0.081(10) Uani 1 1 d . . .
C25 C -0.139(3) 0.0322(13) 0.684(2) 0.089(12) Uani 1 1 d . . .
C26 C -0.1184(8) 0.0058(5) 0.8137(7) 0.036(6) Uani 1 1 d . . .
C27 C -0.6147(8) 0.1625(5) 0.6182(7) 0.061(8) Uani 1 1 d R . .
C28 C -0.6331(8) 0.1183(5) 0.6500(7) 0.079(10) Uani 1 1 d R . .
H28 H -0.6392 0.0891 0.6227 0.095 Uiso 1 1 calc R . .
C29 C -0.6426(8) 0.1167(5) 0.7216(7) 0.073(9) Uani 1 1 d R . .
H29 H -0.6551 0.0865 0.7433 0.087 Uiso 1 1 calc R . .
C30 C -0.6337(8) 0.1594(5) 0.7615(7) 0.057(8) Uani 1 1 d R . .
C31 C -0.6154(8) 0.2036(5) 0.7298(7) 0.065(8) Uani 1 1 d R . .
H31 H -0.6093 0.2327 0.7570 0.078 Uiso 1 1 calc R . .
C32 C -0.6059(8) 0.2051(5) 0.6581(7) 0.065(8) Uani 1 1 d R . .
H32 H -0.5933 0.2353 0.6365 0.078 Uiso 1 1 calc R . .
C33 C -0.641(3) 0.1590(13) 0.845(2) 0.118(13) Uani 1 1 d . . .
H33A H -0.6540 0.1256 0.8598 0.176 Uiso 1 1 calc R . .
H33B H -0.7028 0.1799 0.8535 0.176 Uiso 1 1 calc R . .
H33C H -0.5705 0.1712 0.8720 0.176 Uiso 1 1 calc R . .
C34 C -0.585(2) 0.1312(11) 0.5014(15) 0.050(7) Uani 1 1 d . . .
N5 N -0.5952(5) 0.1694(2) 0.5462(4) 0.047(5) Uani 1 1 d . . .
H5A H -0.5898 0.1993 0.5304 0.056 Uiso 1 1 calc R . .
C35 C -0.5775(5) 0.1458(2) 0.4271(4) 0.048(7) Uani 1 1 d R . .
C36 C -0.5993(5) 0.1919(2) 0.3978(4) 0.063(8) Uani 1 1 d R . .
H36 H -0.6237 0.2172 0.4254 0.076 Uiso 1 1 calc R . .
C37 C -0.5854(5) 0.2008(2) 0.3280(4) 0.054(7) Uani 1 1 d R . .
H37 H -0.6003 0.2323 0.3080 0.064 Uiso 1 1 calc R . .
C38 C -0.5497(5) 0.1637(2) 0.2876(4) 0.051(7) Uani 1 1 d R . .
H38 H -0.5403 0.1698 0.2399 0.062 Uiso 1 1 calc R . .
N6 N -0.5280(5) 0.1176(2) 0.3168(4) 0.043(5) Uani 1 1 d R . .
C39 C -0.5418(5) 0.1086(2) 0.3866(4) 0.050(7) Uani 1 1 d R . .
H39 H -0.5270 0.0771 0.4066 0.061 Uiso 1 1 calc R . .
N7 N -0.3318(5) 0.0504(2) 0.3431(4) 0.053(6) Uani 1 1 d R . .
C40 C -0.3387(5) 0.0145(2) 0.3936(4) 0.058(8) Uani 1 1 d R . .
H40 H -0.4038 -0.0053 0.3900 0.069 Uiso 1 1 calc R . .
C41 C -0.2505(5) 0.0076(2) 0.4495(4) 0.047(7) Uani 1 1 d R . .
H41 H -0.2552 -0.0169 0.4840 0.056 Uiso 1 1 calc R . .
C42 C -0.1553(5) 0.0365(2) 0.4548(4) 0.055(7) Uani 1 1 d R . .
H42 H -0.0950 0.0318 0.4930 0.066 Uiso 1 1 calc R . .
C43 C -0.1483(5) 0.0724(2) 0.4043(4) 0.044(7) Uani 1 1 d R . .
H43 H -0.0833 0.0922 0.4079 0.052 Uiso 1 1 calc R . .
C44 C -0.2366(5) 0.0793(2) 0.3484(4) 0.039(6) Uani 1 1 d R . .
C45 C -0.2354(5) 0.1146(2) 0.2943(4) 0.036(6) Uani 1 1 d R . .
C46 C -0.1510(5) 0.1478(2) 0.2882(4) 0.042(7) Uani 1 1 d R . .
H46 H -0.0852 0.1487 0.3232 0.051 Uiso 1 1 calc R . .
C47 C -0.1627(5) 0.1798(2) 0.2309(4) 0.064(8) Uani 1 1 d R . .
H47 H -0.1050 0.2025 0.2268 0.076 Uiso 1 1 calc R . .
C48 C -0.2589(5) 0.1785(2) 0.1797(4) 0.077(10) Uani 1 1 d R . .
H48 H -0.2670 0.2004 0.1405 0.093 Uiso 1 1 calc R . .
C49 C -0.3434(5) 0.1453(2) 0.1857(4) 0.066(8) Uani 1 1 d R . .
H49 H -0.4091 0.1444 0.1507 0.079 Uiso 1 1 calc R . .
N8 N -0.3316(5) 0.1133(2) 0.2430(4) 0.047(6) Uani 1 1 d R . .
C50 C -0.563(3) 0.0147(12) 0.2679(18) 0.077(10) Uani 1 1 d . . .
C51 C -0.396(2) 0.0177(10) 0.1962(15) 0.044(7) Uani 1 1 d . . .
C52 C -0.572(3) 0.0780(11) 0.1684(19) 0.072(9) Uani 1 1 d . . .
O1 O 0.0873(11) 0.0858(5) 0.5164(8) 0.035(4) Uani 1 1 d U . .
O2 O 0.1381(18) -0.0157(8) 0.7461(11) 0.075(6) Uani 1 1 d . . .
O3 O -0.1607(16) -0.0268(7) 0.8433(10) 0.073(6) Uani 1 1 d . . .
O4 O -0.1793(19) 0.0165(9) 0.6291(13) 0.088(7) Uani 1 1 d . . .
O5 O -0.5908(15) 0.0872(7) 0.5150(11) 0.071(6) Uani 1 1 d . . .
O6 O -0.6271(17) -0.0157(8) 0.2839(11) 0.079(7) Uani 1 1 d . . .
O7 O -0.3608(14) -0.0115(8) 0.1611(11) 0.070(6) Uani 1 1 d . . .
O8 O -0.6231(15) 0.0878(7) 0.1134(10) 0.060(6) Uani 1 1 d . . .
Re1 Re -0.04818(8) 0.05311(4) 0.76983(6) 0.0472(4) Uani 1 1 d . . .
Re2 Re -0.46160(8) 0.06215(4) 0.25101(6) 0.0480(4) Uani 1 1 d . . .
C53 C 0.7543(10) 0.1557(4) 0.5683(5) 0.081(10) Uani 1 1 d D . .
O9 O 0.6493(12) 0.2317(5) 0.5184(9) 0.093(7) Uani 1 1 d D . .
O10 O 0.7067(13) 0.1743(5) 0.4355(5) 0.067(5) Uani 1 1 d D . .
O11 O 0.8442(10) 0.2257(5) 0.5104(9) 0.091(7) Uani 1 1 d D . .
F1 F 0.6591(11) 0.1309(5) 0.5695(8) 0.102(6) Uani 1 1 d D . .
F2 F 0.8268(12) 0.1209(4) 0.5568(8) 0.091(5) Uani 1 1 d D . .
F3 F 0.7889(13) 0.1754(5) 0.6333(5) 0.095(6) Uani 1 1 d D . .
S1 S 0.7378(6) 0.2011(3) 0.5007(4) 0.076(2) Uani 1 1 d D . .
C54 C 0.0388(10) 0.2703(5) 1.0201(7) 0.085(5) Uani 0.588(11) 1 d PDU A 1
O12 O -0.0429(18) 0.2763(10) 1.1342(7) 0.077(6) Uani 0.588(11) 1 d PDU A 1
O13 O -0.1573(14) 0.3027(8) 1.0248(12) 0.092(6) Uani 0.588(11) 1 d PDU A 1
O14 O -0.1187(17) 0.2160(6) 1.0484(14) 0.068(6) Uani 0.588(11) 1 d PDU A 1
F4 F 0.1243(11) 0.2443(8) 1.0556(12) 0.101(7) Uani 0.588(11) 1 d PDU A 1
F5 F 0.0797(15) 0.3159(6) 1.0227(13) 0.104(7) Uani 0.588(11) 1 d PDU A 1
F6 F 0.0189(16) 0.2554(9) 0.9517(8) 0.091(7) Uani 0.588(11) 1 d PDU A 1
S2 S -0.0834(8) 0.2659(4) 1.0600(7) 0.068(3) Uani 0.588(11) 1 d PDU A 1
C54A C -0.0952(17) 0.2903(7) 1.0059(10) 0.079(5) Uani 0.412(11) 1 d PDU A 2
O12A O 0.0730(15) 0.2470(12) 1.0765(16) 0.080(7) Uani 0.412(11) 1 d PDU A 2
O13A O -0.069(3) 0.2771(12) 1.1402(10) 0.075(7) Uani 0.412(11) 1 d PDU A 2
O14A O -0.104(3) 0.2062(8) 1.0615(17) 0.067(7) Uani 0.412(11) 1 d PDU A 2
F4A F -0.074(3) 0.2723(11) 0.9440(9) 0.100(8) Uani 0.412(11) 1 d PDU A 2
F5A F -0.2072(18) 0.2942(12) 0.9946(16) 0.108(8) Uani 0.412(11) 1 d PDU A 2
F6A F -0.050(3) 0.3352(7) 1.0156(16) 0.097(7) Uani 0.412(11) 1 d PDU A 2
S2A S -0.0451(14) 0.2512(6) 1.0789(9) 0.066(4) Uani 0.412(11) 1 d PDU A 2
O15 O -0.253(4) 0.0620(18) 1.013(3) 0.16(2) Uani 0.61(5) 1 d P B 2
O15A O -0.621(5) -0.057(2) 0.074(3) 0.10(3) Uani 0.39(5) 1 d P B 2


_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
N1 C8 1.353(13) . ?
N1 C1 1.4578 . ?
N1 H1 0.8800 . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 C7 1.54(3) . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O1 1.202(16) . ?
C8 C9 1.4923 . ?
C9 C10 1.3900 . ?
C9 C13 1.3900 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 N2 1.3900 . ?
C12 H12 0.9500 . ?
N2 C13 1.3900 . ?
N2 Re1 2.240(6) . ?
C13 H13 0.9500 . ?
N3 C14 1.3900 . ?
N3 C18 1.3900 . ?
N3 Re1 2.158(7) . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.4333 . ?
C19 C20 1.3900 . ?
C19 N4 1.3900 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 C22 1.3900 . ?
C21 H21 0.9500 . ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 N4 1.3900 . ?
C23 H23 0.9500 . ?
N4 Re1 2.170(7) . ?
C24 O2 1.23(3) . ?
C24 Re1 1.81(4) . ?
C25 O4 1.15(4) . ?
C25 Re1 1.91(4) . ?
C26 O3 1.22(2) . ?
C26 Re1 1.830(13) . ?
C27 C28 1.3900 . ?
C27 C32 1.3900 . ?
C27 N5 1.446(18) . ?
C28 C29 1.3900 . ?
C28 H28 0.9500 . ?
C29 C30 1.3900 . ?
C29 H29 0.9500 . ?
C30 C31 1.3900 . ?
C30 C33 1.61(4) . ?
C31 C32 1.3900 . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 O5 1.24(3) . ?
C34 N5 1.37(3) . ?
C34 C35 1.49(3) . ?
N5 H5A 0.8800 . ?
C35 C36 1.3900 . ?
C35 C39 1.3900 . ?
C36 C37 1.3900 . ?
C36 H36 0.9500 . ?
C37 C38 1.3900 . ?
C37 H37 0.9500 . ?
C38 N6 1.3900 . ?
C38 H38 0.9500 . ?
N6 C39 1.3900 . ?
N6 Re2 2.208(6) . ?
C39 H39 0.9500 . ?
N7 C40 1.3900 . ?
N7 C44 1.3900 . ?
N7 Re2 2.175(7) . ?
C40 C41 1.3900 . ?
C40 H40 0.9500 . ?
C41 C42 1.3900 . ?
C41 H41 0.9500 . ?
C42 C43 1.3900 . ?
C42 H42 0.9500 . ?
C43 C44 1.3900 . ?
C43 H43 0.9500 . ?
C44 C45 1.4167 . ?
C45 C46 1.3900 . ?
C45 N8 1.3900 . ?
C46 C47 1.3900 . ?
C46 H46 0.9500 . ?
C47 C48 1.3900 . ?
C47 H47 0.9500 . ?
C48 C49 1.3900 . ?
C48 H48 0.9500 . ?
C49 N8 1.3900 . ?
C49 H49 0.9500 . ?
N8 Re2 2.135(6) . ?
C50 O6 1.21(3) . ?
C50 Re2 1.86(4) . ?
C51 O7 1.17(3) . ?
C51 Re2 1.87(3) . ?
C52 O8 1.16(3) . ?
C52 Re2 1.94(4) . ?
C53 F2 1.341(9) . ?
C53 F1 1.344(8) . ?
C53 F3 1.351(8) . ?
C53 S1 1.779(7) . ?
O9 S1 1.445(8) . ?
O10 S1 1.438(8) . ?
O11 S1 1.440(8) . ?
C54 F5 1.341(9) . ?
C54 F4 1.344(9) . ?
C54 F6 1.351(8) . ?
C54 S2 1.779(7) . ?
O12 S2 1.445(8) . ?
O13 S2 1.438(8) . ?
O14 S2 1.440(8) . ?
C54A F5A 1.341(9) . ?
C54A F4A 1.344(9) . ?
C54A F6A 1.351(9) . ?
C54A S2A 1.779(7) . ?
O12A S2A 1.445(8) . ?
O13A S2A 1.438(8) . ?
O14A S2A 1.440(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 123.5(6) . . ?
C8 N1 H1 118.3 . . ?
C1 N1 H1 118.3 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 N1 125.1 . . ?
C6 C1 N1 114.6 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C7 119.0(11) . . ?
C5 C4 C7 120.9(11) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 124.8(10) . . ?
O1 C8 C9 120.0(7) . . ?
N1 C8 C9 115.2(6) . . ?
C10 C9 C13 120.0 . . ?
C10 C9 C8 126.7 . . ?
C13 C9 C8 113.3 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
N2 C12 C11 120.0 . . ?
N2 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 N2 C13 120.0 . . ?
C12 N2 Re1 122.63(19) . . ?
C13 N2 Re1 117.07(19) . . ?
N2 C13 C9 120.0 . . ?
N2 C13 H13 120.0 . . ?
C9 C13 H13 120.0 . . ?
C14 N3 C18 120.0 . . ?
C14 N3 Re1 123.76(19) . . ?
C18 N3 Re1 116.18(19) . . ?
C15 C14 N3 120.0 . . ?
C15 C14 H14 120.0 . . ?
N3 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 N3 120.0 . . ?
C17 C18 C19 122.6 . . ?
N3 C18 C19 117.4 . . ?
C20 C19 N4 120.0 . . ?
C20 C19 C18 126.6 . . ?
N4 C19 C18 113.4 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
N4 C23 C22 120.0 . . ?
N4 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 N4 C19 120.0 . . ?
C23 N4 Re1 121.99(17) . . ?
C19 N4 Re1 117.90(17) . . ?
O2 C24 Re1 176(3) . . ?
O4 C25 Re1 170(3) . . ?
O3 C26 Re1 177.1(12) . . ?
C28 C27 C32 120.0 . . ?
C28 C27 N5 126.3(7) . . ?
C32 C27 N5 113.6(7) . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 C33 118.4(14) . . ?
C29 C30 C33 121.6(14) . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.0 . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O5 C34 N5 127(2) . . ?
O5 C34 C35 118(2) . . ?
N5 C34 C35 114(2) . . ?
C34 N5 C27 122.6(14) . . ?
C34 N5 H5A 118.7 . . ?
C27 N5 H5A 118.7 . . ?
C36 C35 C39 120.0 . . ?
C36 C35 C34 126.1(11) . . ?
C39 C35 C34 113.9(11) . . ?
C37 C36 C35 120.0 . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C38 C37 C36 120.0 . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
N6 C38 C37 120.0 . . ?
N6 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 N6 C39 120.0 . . ?
C38 N6 Re2 117.50(18) . . ?
C39 N6 Re2 122.39(18) . . ?
N6 C39 C35 120.0 . . ?
N6 C39 H39 120.0 . . ?
C35 C39 H39 120.0 . . ?
C40 N7 C44 120.0 . . ?
C40 N7 Re2 123.01(17) . . ?
C44 N7 Re2 116.93(17) . . ?
C41 C40 N7 120.0 . . ?
C41 C40 H40 120.0 . . ?
N7 C40 H40 120.0 . . ?
C42 C41 C40 120.0 . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 120.0 . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C44 C43 C42 120.0 . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C43 C44 N7 120.0 . . ?
C43 C44 C45 123.5 . . ?
N7 C44 C45 116.5 . . ?
C46 C45 N8 120.0 . . ?
C46 C45 C44 127.3 . . ?
N8 C45 C44 112.7 . . ?
C47 C46 C45 120.0 . . ?
C47 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C47 C48 120.0 . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C49 C48 C47 120.0 . . ?
C49 C48 H48 120.0 . . ?
C47 C48 H48 120.0 . . ?
C48 C49 N8 120.0 . . ?
C48 C49 H49 120.0 . . ?
N8 C49 H49 120.0 . . ?
C49 N8 C45 120.0 . . ?
C49 N8 Re2 119.48(18) . . ?
C45 N8 Re2 120.52(18) . . ?
O6 C50 Re2 175(3) . . ?
O7 C51 Re2 176(2) . . ?
O8 C52 Re2 169(3) . . ?
C24 Re1 C26 93.1(11) . . ?
C24 Re1 C25 92.8(15) . . ?
C26 Re1 C25 86.4(12) . . ?
C24 Re1 N3 169.5(10) . . ?
C26 Re1 N3 91.2(4) . . ?
C25 Re1 N3 97.0(11) . . ?
C24 Re1 N4 95.4(11) . . ?
C26 Re1 N4 93.5(4) . . ?
C25 Re1 N4 171.8(11) . . ?
N3 Re1 N4 74.7(2) . . ?
C24 Re1 N2 89.9(10) . . ?
C26 Re1 N2 176.9(4) . . ?
C25 Re1 N2 92.9(11) . . ?
N3 Re1 N2 86.0(2) . . ?
N4 Re1 N2 86.7(2) . . ?
C50 Re2 C51 89.7(12) . . ?
C50 Re2 C52 84.9(13) . . ?
C51 Re2 C52 89.5(12) . . ?
C50 Re2 N8 172.9(10) . . ?
C51 Re2 N8 90.1(8) . . ?
C52 Re2 N8 102.2(9) . . ?
C50 Re2 N7 99.6(10) . . ?
C51 Re2 N7 92.1(8) . . ?
C52 Re2 N7 175.2(9) . . ?
N8 Re2 N7 73.33(19) . . ?
C50 Re2 N6 94.0(10) . . ?
C51 Re2 N6 176.0(8) . . ?
C52 Re2 N6 92.3(9) . . ?
N8 Re2 N6 86.0(2) . . ?
N7 Re2 N6 85.8(2) . . ?
F2 C53 F1 103.2(11) . . ?
F2 C53 F3 108.9(11) . . ?
F1 C53 F3 108.8(11) . . ?
F2 C53 S1 112.1(7) . . ?
F1 C53 S1 112.0(7) . . ?
F3 C53 S1 111.4(7) . . ?
O10 S1 O11 116.7(10) . . ?
O10 S1 O9 113.7(10) . . ?
O11 S1 O9 112.4(10) . . ?
O10 S1 C53 104.5(6) . . ?
O11 S1 C53 104.2(6) . . ?
O9 S1 C53 103.6(6) . . ?
F5 C54 F4 103.2(11) . . ?
F5 C54 F6 108.9(11) . . ?
F4 C54 F6 108.8(11) . . ?
F5 C54 S2 112.2(7) . . ?
F4 C54 S2 112.0(7) . . ?
F6 C54 S2 111.4(7) . . ?
O13 S2 O14 116.7(10) . . ?
O13 S2 O12 113.7(10) . . ?
O14 S2 O12 112.4(10) . . ?
O13 S2 C54 104.5(6) . . ?
O14 S2 C54 104.2(6) . . ?
O12 S2 C54 103.6(6) . . ?
F5A C54A F4A 103.2(11) . . ?
F5A C54A F6A 108.9(11) . . ?
F4A C54A F6A 108.8(11) . . ?
F5A C54A S2A 112.1(7) . . ?
F4A C54A S2A 112.1(7) . . ?
F6A C54A S2A 111.4(7) . . ?
O13A S2A O14A 116.7(10) . . ?
O13A S2A O12A 113.7(10) . . ?
O14A S2A O12A 112.4(10) . . ?
O13A S2A C54A 104.5(6) . . ?
O14A S2A C54A 104.2(6) . . ?
O12A S2A C54A 103.6(6) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.523
_refine_diff_density_min         -1.264
_refine_diff_density_rms         0.211
_database_code_depnum_ccdc_archive 'CCDC 893641'
#######################################################################
#
#                 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_bmk1004
#TrackingRef 'o-Br_bmk1004.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N2 O'
_chemical_formula_sum            'C12 H9 Br N2 O'
_chemical_formula_weight         277.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/a

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

_cell_length_a                   12.8722(4)
_cell_length_b                   4.9256(2)
_cell_length_c                   17.5710(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.327(2)
_cell_angle_gamma                90.00
_cell_volume                     1079.41(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2138
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      27.49

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    3.786
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3964
_exptl_absorpt_correction_T_max  0.6005
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3995
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2464
_reflns_number_gt                2138
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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)+(0.0367P)²+1.3589P] 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     SHELXL
_refine_ls_extinction_coef       0.0277(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.45618(19) 0.4164(5) 0.35883(15) 0.0189(5) Uani 1 1 d . . .
C2 C 0.3847(2) 0.6314(5) 0.34065(15) 0.0203(5) Uani 1 1 d . . .
H2 H 0.3858 0.7500 0.2982 0.024 Uiso 1 1 calc R . .
C3 C 0.3116(2) 0.6692(6) 0.38594(17) 0.0254(6) Uani 1 1 d . . .
H3 H 0.2613 0.8139 0.3750 0.030 Uiso 1 1 calc R . .
C4 C 0.3132(2) 0.4926(6) 0.44714(17) 0.0295(6) Uani 1 1 d . . .
H4 H 0.2619 0.5188 0.4771 0.035 Uiso 1 1 calc R . .
C5 C 0.4527(2) 0.2503(6) 0.42266(16) 0.0230(5) Uani 1 1 d . . .
H5 H 0.5024 0.1048 0.4353 0.028 Uiso 1 1 calc R . .
C6 C 0.53140(19) 0.3365(5) 0.30969(14) 0.0182(5) Uani 1 1 d . . .
C7 C 0.61413(19) 0.4886(5) 0.20607(15) 0.0199(5) Uani 1 1 d . . .
C8 C 0.5784(2) 0.6177(5) 0.13346(16) 0.0225(5) Uani 1 1 d . . .
C9 C 0.6259(2) 0.5682(6) 0.07227(17) 0.0277(6) Uani 1 1 d . . .
H9 H 0.6014 0.6601 0.0236 0.033 Uiso 1 1 calc R . .
C10 C 0.7092(2) 0.3839(6) 0.08252(18) 0.0303(7) Uani 1 1 d . . .
H10 H 0.7408 0.3449 0.0403 0.036 Uiso 1 1 calc R . .
C11 C 0.7467(2) 0.2559(7) 0.15435(19) 0.0305(6) Uani 1 1 d . . .
H11 H 0.8044 0.1308 0.1613 0.037 Uiso 1 1 calc R . .
C12 C 0.7001(2) 0.3100(6) 0.21623(17) 0.0256(6) Uani 1 1 d . . .
H12 H 0.7271 0.2244 0.2656 0.031 Uiso 1 1 calc R . .
N1 N 0.38269(19) 0.2862(5) 0.46697(14) 0.0287(5) Uani 1 1 d . . .
N2 N 0.56139(17) 0.5359(4) 0.26657(12) 0.0196(4) Uani 1 1 d . . .
H2A H 0.5472 0.7049 0.2768 0.024 Uiso 1 1 calc R . .
O1 O 0.55934(16) 0.0982(4) 0.30756(12) 0.0264(4) Uani 1 1 d . . .
Br1 Br 0.45765(2) 0.85133(6) 0.116450(16) 0.02874(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(4) . ?
C1 C5 1.398(4) . ?
C1 C6 1.501(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.342(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.341(3) . ?
C5 H5 0.9500 . ?
C6 O1 1.231(3) . ?
C6 N2 1.354(3) . ?
C7 C12 1.390(4) . ?
C7 C8 1.397(4) . ?
C7 N2 1.415(3) . ?
C8 C9 1.383(4) . ?
C8 Br1 1.897(3) . ?
C9 C10 1.383(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N2 H2A 0.8800 . ?

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 C1 C5 118.7(2) . . ?
C2 C1 C6 123.6(2) . . ?
C5 C1 C6 117.5(2) . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
N1 C4 C3 124.1(2) . . ?
N1 C4 H4 118.0 . . ?
C3 C4 H4 118.0 . . ?
N1 C5 C1 123.3(3) . . ?
N1 C5 H5 118.4 . . ?
C1 C5 H5 118.4 . . ?
O1 C6 N2 123.3(2) . . ?
O1 C6 C1 120.2(2) . . ?
N2 C6 C1 116.5(2) . . ?
C12 C7 C8 118.5(2) . . ?
C12 C7 N2 121.5(2) . . ?
C8 C7 N2 120.0(2) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 Br1 119.1(2) . . ?
C7 C8 Br1 119.44(19) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.3(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C5 N1 C4 116.7(2) . . ?
C6 N2 C7 123.9(2) . . ?
C6 N2 H2A 118.1 . . ?
C7 N2 H2A 118.1 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.088
_database_code_depnum_ccdc_archive 'CCDC 893642'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 I N2 O'

_chemical_formula_sum            'C12 H9 I N2 O'
_chemical_formula_weight         324.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   10.8408(5)
_cell_length_b                   21.2412(11)
_cell_length_c                   4.8537(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1117.67(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2103
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.844
_shelx_estimated_absorpt_T_min   0.483
_shelx_estimated_absorpt_T_max   0.804
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.483
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.437
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2403
_reflns_number_gt                2099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'COLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'


_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+3.1563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0088(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2403
_refine_ls_number_parameters     147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3735(6) 0.1328(3) 0.6843(14) 0.0186(14) Uani 1 1 d . . . . .
C2 C 0.4210(6) 0.0814(3) 0.8285(19) 0.0234(17) Uani 1 1 d . . . . .
H2 H 0.4768 0.0875 0.9770 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3853(6) 0.0213(3) 0.752(2) 0.029(2) Uani 1 1 d . . . . .
H3 H 0.4149 -0.0146 0.8480 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3055(6) 0.0148(4) 0.5311(16) 0.0265(16) Uani 1 1 d . . . . .
H4 H 0.2834 -0.0266 0.4758 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2931(6) 0.1211(4) 0.4701(16) 0.0245(16) Uani 1 1 d . . . . .
H5 H 0.2608 0.1562 0.3727 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4079(5) 0.1976(3) 0.788(2) 0.0192(11) Uani 1 1 d . . . . .
C8 C 0.4247(7) 0.3081(3) 0.6471(14) 0.0190(14) Uani 1 1 d . . . . .
C9 C 0.3497(6) 0.3539(3) 0.5252(14) 0.0195(14) Uani 1 1 d . . . . .
C10 C 0.3717(7) 0.4173(3) 0.5757(16) 0.0248(16) Uani 1 1 d . . . . .
H10 H 0.3227 0.4484 0.4869 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4644(7) 0.4355(3) 0.754(2) 0.0277(19) Uani 1 1 d . . . . .
H11 H 0.4771 0.4789 0.7922 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5381(7) 0.3912(4) 0.8768(15) 0.0281(17) Uani 1 1 d . . . . .
H12 H 0.6020 0.4040 0.9983 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5197(6) 0.3274(3) 0.824(2) 0.0214(18) Uani 1 1 d . . . . .
H13 H 0.5717 0.2970 0.9080 0.026 Uiso 1 1 calc R U . . .
N1 N 0.2572(6) 0.0634(3) 0.3900(13) 0.0272(14) Uani 1 1 d . . . . .
N2 N 0.4036(6) 0.2433(3) 0.5917(12) 0.0198(12) Uani 1 1 d . . . . .
H2A H 0.3868 0.2322 0.4212 0.024 Uiso 1 1 calc R U . . .
O1 O 0.4362(5) 0.2060(3) 1.0257(11) 0.0261(11) Uani 1 1 d . . . . .
I1 I 0.19574(3) 0.32757(2) 0.29086(15) 0.02487(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.380(10) . ?
C1 C2 1.396(10) . ?
C1 C6 1.512(10) . ?
C2 C3 1.385(11) . ?
C3 C4 1.384(12) . ?
C4 N1 1.343(10) . ?
C5 N1 1.344(10) . ?
C6 O1 1.206(13) . ?
C6 N2 1.363(11) . ?
C8 C9 1.399(10) . ?
C8 C13 1.402(11) . ?
C8 N2 1.419(9) . ?
C9 C10 1.391(10) . ?
C9 I1 2.095(7) . ?
C10 C11 1.382(12) . ?
C11 C12 1.371(11) . ?
C12 C13 1.392(10) . ?

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
C5 C1 C2 118.0(7) . . ?
C5 C1 C6 124.8(7) . . ?
C2 C1 C6 117.0(7) . . ?
C3 C2 C1 118.9(8) . . ?
C4 C3 C2 118.3(8) . . ?
N1 C4 C3 124.2(7) . . ?
N1 C5 C1 124.4(7) . . ?
O1 C6 N2 124.9(6) . . ?
O1 C6 C1 121.1(8) . . ?
N2 C6 C1 114.0(9) . . ?
C9 C8 C13 118.8(6) . . ?
C9 C8 N2 119.9(6) . . ?
C13 C8 N2 121.3(6) . . ?
C10 C9 C8 120.0(7) . . ?
C10 C9 I1 119.4(5) . . ?
C8 C9 I1 120.5(5) . . ?
C11 C10 C9 120.4(7) . . ?
C12 C11 C10 120.2(7) . . ?
C11 C12 C13 120.3(7) . . ?
C12 C13 C8 120.2(7) . . ?
C4 N1 C5 116.1(7) . . ?
C6 N2 C8 123.5(6) . . ?

_refine_diff_density_max         1.244
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.112

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 893643'
#######################################################################
#
#                 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_bmk1001
#TrackingRef 'o-Me_bmk1001.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   10.5120(12)
_cell_length_b                   4.8327(6)
_cell_length_c                   21.187(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.264(7)
_cell_angle_gamma                90.00
_cell_volume                     1055.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    919
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      27.51

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_process_details   Denzo/Scalepack

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4182
_diffrn_reflns_av_R_equivalents  0.1857
_diffrn_reflns_av_sigmaI/netI    0.2626
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2414
_reflns_number_gt                919
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  SHELXL-97

_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)+(0.0277P)²+0.0000P] 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         2414
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2443
_refine_ls_R_factor_gt           0.0919
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1460
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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 0.5269(3) -0.1688(8) 0.87937(15) 0.0276(9) Uani 1 1 d . . .
C2 C 0.4659(4) -0.2920(8) 0.92394(16) 0.0398(11) Uani 1 1 d . . .
H2 H 0.4908 -0.2451 0.9682 0.048 Uiso 1 1 calc R . .
C3 C 0.3689(4) -0.4832(8) 0.90458(17) 0.0462(12) Uani 1 1 d . . .
H3 H 0.3277 -0.5720 0.9352 0.055 Uiso 1 1 calc R . .
C4 C 0.3325(4) -0.5434(8) 0.83996(16) 0.0388(11) Uani 1 1 d . . .
H4 H 0.2648 -0.6736 0.8268 0.047 Uiso 1 1 calc R . .
C5 C 0.4845(4) -0.2440(8) 0.81532(16) 0.0375(10) Uani 1 1 d . . .
H5 H 0.5260 -0.1613 0.7840 0.045 Uiso 1 1 calc R . .
C6 C 0.6301(4) 0.0412(8) 0.90182(17) 0.0346(10) Uani 1 1 d . . .
C7 C 0.7842(4) 0.3680(8) 0.86575(16) 0.0324(10) Uani 1 1 d . . .
C8 C 0.8351(4) 0.4905(8) 0.92495(16) 0.0385(11) Uani 1 1 d . . .
H8 H 0.8031 0.4399 0.9623 0.046 Uiso 1 1 calc R . .
C9 C 0.9327(4) 0.6867(8) 0.92892(16) 0.0404(11) Uani 1 1 d . . .
H9 H 0.9665 0.7675 0.9696 0.049 Uiso 1 1 calc R . .
C10 C 0.9828(4) 0.7696(8) 0.87657(17) 0.0366(10) Uani 1 1 d . . .
C11 C 0.9296(4) 0.6501(8) 0.81758(17) 0.0428(11) Uani 1 1 d . . .
H11 H 0.9607 0.7047 0.7802 0.051 Uiso 1 1 calc R . .
C12 C 0.8328(4) 0.4541(8) 0.81218(16) 0.0393(11) Uani 1 1 d . . .
H12 H 0.7985 0.3762 0.7712 0.047 Uiso 1 1 calc R . .
C13 C 1.0911(4) 0.9791(8) 0.88355(17) 0.0498(13) Uani 1 1 d . . .
H13A H 1.0547 1.1662 0.8817 0.075 Uiso 1 1 calc R . .
H13B H 1.1387 0.9551 0.8485 0.075 Uiso 1 1 calc R . .
H13C H 1.1504 0.9520 0.9249 0.075 Uiso 1 1 calc R . .
N1 N 0.6856(3) 0.1644(6) 0.85647(12) 0.0325(9) Uani 1 1 d . . .
H1 H 0.6569 0.1115 0.8165 0.039 Uiso 1 1 calc R . .
N2 N 0.3884(3) -0.4263(7) 0.79478(12) 0.0381(9) Uani 1 1 d . . .
O1 O 0.6618(2) 0.0919(5) 0.95957(10) 0.0461(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(5) . ?
C1 C5 1.391(4) . ?
C1 C6 1.494(5) . ?
C2 C3 1.378(5) . ?
C3 C4 1.379(4) . ?
C4 N2 1.342(4) . ?
C5 N2 1.347(4) . ?
C6 O1 1.228(3) . ?
C6 N1 1.355(4) . ?
C7 C8 1.396(4) . ?
C7 C12 1.396(5) . ?
C7 N1 1.414(4) . ?
C8 C9 1.387(5) . ?
C9 C10 1.377(5) . ?
C10 C11 1.391(4) . ?
C10 C13 1.509(5) . ?
C11 C12 1.379(5) . ?

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 C1 C5 116.9(4) . . ?
C2 C1 C6 118.8(3) . . ?
C5 C1 C6 124.2(3) . . ?
C1 C2 C3 120.2(3) . . ?
C2 C3 C4 118.8(4) . . ?
N2 C4 C3 123.0(4) . . ?
N2 C5 C1 124.3(3) . . ?
O1 C6 N1 123.2(4) . . ?
O1 C6 C1 119.4(3) . . ?
N1 C6 C1 117.3(3) . . ?
C8 C7 C12 117.9(4) . . ?
C8 C7 N1 124.2(3) . . ?
C12 C7 N1 118.0(3) . . ?
C9 C8 C7 119.6(4) . . ?
C10 C9 C8 123.0(4) . . ?
C9 C10 C11 116.9(4) . . ?
C9 C10 C13 121.1(3) . . ?
C11 C10 C13 122.0(4) . . ?
C12 C11 C10 121.3(4) . . ?
C11 C12 C7 121.3(4) . . ?
C6 N1 C7 127.7(3) . . ?
C4 N2 C5 116.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 893644'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N2 O'
_chemical_formula_sum            'C12 H9 Br N2 O'
_chemical_formula_weight         277.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   9.8494(18)
_cell_length_b                   3.8718(7)
_cell_length_c                   13.972(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.018(10)
_cell_angle_gamma                90
_cell_volume                     529.87(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    994
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      25.22

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.856
_shelx_estimated_absorpt_T_min   0.346
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.346
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   Denzo/Scalepack


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         20.827
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.586
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.586
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.567
_reflns_number_total             1086
_reflns_number_gt                989
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.540

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'cOLLECT,Nonius BV, 1997-2001'
_computing_cell_refinement       DENZO/SCALEPACK
_computing_data_reduction        DENZO/SCALEPACK
_computing_structure_solution    SHELXs-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+7.6971P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1086
_refine_ls_number_parameters     146
_refine_ls_number_restraints     271
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.1746
_refine_ls_wR_factor_gt          0.1669
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.7748(2) -0.3150(8) 0.60505(14) 0.0528(9) Uani 1 1 d . . . . .
N1 N 0.5942(2) 0.3632(8) -0.11051(14) 0.031(4) Uani 0.83(2) 1 d R U P A 1
C1 C 0.6750(2) 0.2408(8) -0.17899(14) 0.033(4) Uani 0.83(2) 1 d R U P A 1
H1 H 0.6477 0.2764 -0.2455 0.039 Uiso 0.83(2) 1 calc R U P A 1
C2 C 0.7957(2) 0.0662(8) -0.15016(14) 0.032(4) Uani 0.83(2) 1 d R U P A 1
H2 H 0.8508 -0.0175 -0.1970 0.039 Uiso 0.83(2) 1 calc R U P A 1
C3 C 0.8356(2) 0.0140(8) -0.05284(14) 0.031(4) Uani 0.83(2) 1 d R U P A 1
H3 H 0.9181 -0.1053 -0.0331 0.037 Uiso 0.83(2) 1 calc R U P A 1
C4 C 0.7549(2) 0.1365(8) 0.01564(14) 0.032(4) Uani 0.83(2) 1 d R U P A 1
C5 C 0.6342(2) 0.3111(8) -0.01319(14) 0.031(4) Uani 0.83(2) 1 d R U P A 1
H5 H 0.5790 0.3948 0.0336 0.037 Uiso 0.83(2) 1 calc R U P A 1
C6 C 0.8026(9) 0.081(3) 0.1179(6) 0.034(5) Uani 1 1 d . U . . .
C7 C 0.7300(9) -0.063(3) 0.2766(6) 0.032(6) Uani 1 1 d R . . A .
C8 C 0.8466(9) -0.229(3) 0.3184(6) 0.043(8) Uani 1 1 d R . . . .
H8 H 0.9163 -0.2946 0.2799 0.051 Uiso 1 1 calc R U . . .
C9 C 0.8613(9) -0.299(3) 0.4165(6) 0.041(5) Uani 1 1 d R . . . .
H9 H 0.9409 -0.4122 0.4450 0.049 Uiso 1 1 calc R U . . .
C10 C 0.7593(9) -0.203(3) 0.4728(6) 0.053(10) Uani 1 1 d R . . . .
C11 C 0.6427(9) -0.037(3) 0.4310(6) 0.034(6) Uani 1 1 d R . . . .
H11 H 0.5730 0.0290 0.4695 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6280(9) 0.033(3) 0.3329(6) 0.038(6) Uani 1 1 d R . . . .
H12 H 0.5484 0.1466 0.3043 0.046 Uiso 1 1 calc R U . . .
N2 N 0.7081(18) 0.008(5) 0.1756(12) 0.038(5) Uani 1 1 d . . . . .
H2B H 0.6230 0.0023 0.1491 0.046 Uiso 1 1 calc R U . A .
O1 O 0.9272(13) 0.093(3) 0.1466(9) 0.038(5) Uani 1 1 d . . . . .
N1A N 0.8023(13) 0.178(3) -0.1540(9) 0.031(5) Uani 0.17(2) 1 d R U P A 2
C1A C 0.6625(13) 0.147(3) -0.1794(9) 0.032(5) Uani 0.17(2) 1 d R U P A 2
H1A H 0.6265 0.1661 -0.2450 0.038 Uiso 0.17(2) 1 calc R U P A 2
C2A C 0.5756(13) 0.089(3) -0.1089(9) 0.031(5) Uani 0.17(2) 1 d R U P A 2
H2A H 0.4800 0.0686 -0.1263 0.037 Uiso 0.17(2) 1 calc R U P A 2
C3A C 0.6283(13) 0.062(3) -0.0130(9) 0.032(5) Uani 0.17(2) 1 d R U P A 2
H3A H 0.5689 0.0222 0.0352 0.038 Uiso 0.17(2) 1 calc R U P A 2
C4A C 0.7681(13) 0.092(3) 0.0124(9) 0.032(4) Uani 0.17(2) 1 d R U P A 2
C5A C 0.8551(13) 0.150(3) -0.0581(9) 0.031(5) Uani 0.17(2) 1 d R U P A 2
H5A H 0.9506 0.1708 -0.0407 0.037 Uiso 0.17(2) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.889(9) . ?
N1 C1 1.3900 . ?
N1 C5 1.3900 . ?
C1 C2 1.3900 . ?
C1 H1 0.9500 . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 C6 1.472(9) . ?
C5 H5 0.9500 . ?
C6 O1 1.251(15) . ?
C6 N2 1.324(19) . ?
C6 C4A 1.477(15) . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 N2 1.432(19) . ?
C8 C9 1.3900 . ?
C8 H8 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
N2 H2B 0.8800 . ?
N1A C5A 1.3900 . ?
N1A C1A 1.3900 . ?
C1A C2A 1.3900 . ?
C1A H1A 0.9500 . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9500 . ?

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 N1 C5 120.0 . . ?
N1 C1 C2 120.0 . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C6 121.9(4) . . ?
C3 C4 C6 118.1(4) . . ?
C4 C5 N1 120.0 . . ?
C4 C5 H5 120.0 . . ?
N1 C5 H5 120.0 . . ?
O1 C6 N2 122.7(12) . . ?
O1 C6 C4 120.6(9) . . ?
N2 C6 C4 116.7(10) . . ?
O1 C6 C4A 115.8(11) . . ?
N2 C6 C4A 120.7(11) . . ?
C8 C7 C12 120.0 . . ?
C8 C7 N2 122.4(8) . . ?
C12 C7 N2 117.6(8) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 Br1 120.2(3) . . ?
C11 C10 Br1 119.7(3) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C6 N2 C7 126.7(15) . . ?
C6 N2 H2B 116.6 . . ?
C7 N2 H2B 116.6 . . ?
C5A N1A C1A 120.0 . . ?
C2A C1A N1A 120.0 . . ?
C2A C1A H1A 120.0 . . ?
N1A C1A H1A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A C6 111.7(6) . . ?
C5A C4A C6 128.1(6) . . ?
N1A C5A C4A 120.0 . . ?
N1A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?

_refine_diff_density_max         0.645
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.124

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 893645'
