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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1030631'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_formula_moiety         'C11 H13 N2, O4 Re'
_chemical_formula_sum            'C11 H13 N2 O4 Re'
_chemical_formula_weight         423.44

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   5.8129(1)
_cell_length_b                   11.4171(1)
_cell_length_c                   19.4879(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1293.34(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    7128
_cell_measurement_theta_min      2.7482
_cell_measurement_theta_max      30.4963

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.104
_exptl_crystal_density_diffrn    2.175
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    9.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.6125
_exptl_absorpt_correction_T_max  0.7461

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             A. Poethig
scanspeed                           10 s per frame
dx                                  40 mm
841 frames measured in 2 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            13584
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3972
# number of observed reflections (> n sig(I))
_reflns_number_gt                3799
_reflns_threshold_expression     i>2σ(i)

_computing_data_collection       'APEX II Control Software (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL2013 (Sheldrick, 2013), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     'W=1/[Σ²(FO²)] 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_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.011(7)

_chemical_absolute_configuration unk

_refine_ls_number_reflns         3972
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0319
_refine_ls_wR_factor_gt          0.0314
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.106

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N Uani 0.0938(6) 0.6331(3) 0.87388(17) 1.000 0.0150(10) d . . .
N2 N Uani -0.0061(6) 0.6671(3) 0.76903(17) 1.000 0.0150(10) d . . .
C1 C Uani 0.1495(7) 0.6895(3) 0.81662(18) 1.000 0.0152(10) d . . .
C2 C Uani -0.1682(8) 0.5943(3) 0.7964(2) 1.000 0.0227(12) d . . .
C3 C Uani -0.1074(7) 0.5732(4) 0.8619(2) 1.000 0.0213(12) d . . .
C4 C Uani 0.2229(7) 0.6345(4) 0.9382(2) 1.000 0.0203(12) d . . .
C5 C Uani 0.3743(8) 0.5274(3) 0.94796(19) 1.000 0.0148(10) d . . .
C6 C Uani 0.3794(6) 0.4356(3) 0.90093(18) 1.000 0.0157(10) d . . .
C7 C Uani 0.5231(7) 0.3397(4) 0.9120(2) 1.000 0.0197(12) d . . .
C8 C Uani 0.6625(8) 0.3353(4) 0.9692(2) 1.000 0.0237(12) d . . .
C9 C Uani 0.6613(7) 0.4278(4) 1.0159(2) 1.000 0.0251(11) d . . .
C10 C Uani 0.5156(7) 0.5230(4) 1.0052(2) 1.000 0.0200(12) d . . .
C11 C Uani -0.0122(7) 0.7180(4) 0.6999(2) 1.000 0.0233(12) d . . .
Re1 Re Uani 0.64158(3) 0.93233(2) 0.83098(2) 1.000 0.0142(1) d . . .
O1 O Uani 0.5286(5) 0.8620(2) 0.75998(15) 1.000 0.0216(10) d . . .
O2 O Uani 0.5447(5) 1.0753(2) 0.83118(17) 1.000 0.0275(9) d . . .
O3 O Uani 0.9373(5) 0.9310(2) 0.82634(16) 1.000 0.0240(8) d . . .
O4 O Uani 0.5498(6) 0.8610(3) 0.90394(16) 1.000 0.0300(10) d . . .
H1 H Uiso 0.28060 0.73820 0.81080 1.000 0.0180 c RU . .
H2 H Uiso -0.29970 0.56410 0.77350 1.000 0.0270 c RU . .
H3 H Uiso -0.18830 0.52580 0.89390 1.000 0.0260 c RU . .
H4A H Uiso 0.11310 0.63940 0.97690 1.000 0.0240 c RU . .
H4B H Uiso 0.32050 0.70550 0.93940 1.000 0.0240 c RU . .
H6 H Uiso 0.28480 0.43840 0.86120 1.000 0.0190 c RU . .
H7 H Uiso 0.52500 0.27700 0.88000 1.000 0.0240 c RU . .
H8 H Uiso 0.75900 0.26940 0.97680 1.000 0.0290 c RU . .
H9 H Uiso 0.75940 0.42600 1.05490 1.000 0.0300 c RU . .
H10 H Uiso 0.51320 0.58550 1.03740 1.000 0.0240 c RU . .
H11A H Uiso -0.15940 0.75820 0.69290 1.000 0.0350 c RU . .
H11B H Uiso 0.00460 0.65560 0.66570 1.000 0.0350 c RU . .
H11C H Uiso 0.11400 0.77430 0.69490 1.000 0.0350 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O4 1.723(3) . . yes
Re1 O3 1.721(3) . . yes
Re1 O1 1.729(3) . . yes
Re1 O2 1.727(2) . . yes
N1 C3 1.375(5) . . yes
N1 C4 1.461(5) . . yes
N1 C1 1.328(5) . . yes
N2 C1 1.321(5) . . yes
N2 C2 1.365(5) . . yes
N2 C11 1.468(5) . . yes
C2 C3 1.346(6) . . no
C4 C5 1.519(6) . . no
C5 C10 1.386(6) . . no
C5 C6 1.393(5) . . no
C6 C7 1.394(6) . . no
C7 C8 1.379(6) . . no
C8 C9 1.394(6) . . no
C9 C10 1.394(6) . . no
C1 H1 0.9500 . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4B 0.9900 . . no
C4 H4A 0.9900 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11B 0.9800 . . no
C11 H11C 0.9800 . . no
C11 H11A 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O3 109.46(14) . . . yes
O1 Re1 O4 108.85(14) . . . yes
O2 Re1 O3 109.52(12) . . . yes
O2 Re1 O4 110.12(16) . . . yes
O3 Re1 O4 110.39(15) . . . yes
O1 Re1 O2 108.48(13) . . . yes
C1 N1 C3 107.8(3) . . . yes
C1 N1 C4 126.2(3) . . . yes
C3 N1 C4 126.0(3) . . . yes
C2 N2 C11 125.7(3) . . . yes
C1 N2 C11 125.8(3) . . . yes
C1 N2 C2 108.4(3) . . . yes
N1 C1 N2 109.2(3) . . . yes
N2 C2 C3 107.4(4) . . . yes
N1 C3 C2 107.2(4) . . . yes
N1 C4 C5 113.4(3) . . . yes
C6 C5 C10 119.3(4) . . . no
C4 C5 C6 122.4(3) . . . no
C4 C5 C10 118.3(3) . . . no
C5 C6 C7 120.1(3) . . . no
C6 C7 C8 120.4(4) . . . no
C7 C8 C9 119.8(4) . . . no
C8 C9 C10 119.8(4) . . . no
C5 C10 C9 120.6(4) . . . no
N1 C1 H1 125.00 . . . no
N2 C1 H1 125.00 . . . no
N2 C2 H2 126.00 . . . no
C3 C2 H2 126.00 . . . no
N1 C3 H3 126.00 . . . no
C2 C3 H3 126.00 . . . no
N1 C4 H4B 109.00 . . . no
N1 C4 H4A 109.00 . . . no
H4A C4 H4B 108.00 . . . no
C5 C4 H4A 109.00 . . . no
C5 C4 H4B 109.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C9 C8 H8 120.00 . . . no
C7 C8 H8 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C5 C10 H10 120.00 . . . no
C9 C10 H10 120.00 . . . no
H11B C11 H11C 110.00 . . . no
N2 C11 H11A 110.00 . . . no
N2 C11 H11B 110.00 . . . no
N2 C11 H11C 109.00 . . . no
H11A C11 H11B 109.00 . . . no
H11A C11 H11C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 -0.5(4) . . . . no
C4 N1 C1 N2 179.6(4) . . . . no
C1 N1 C3 C2 0.6(5) . . . . no
C4 N1 C3 C2 -179.5(4) . . . . no
C1 N1 C4 C5 -99.4(5) . . . . no
C3 N1 C4 C5 80.8(5) . . . . no
C2 N2 C1 N1 0.3(4) . . . . no
C11 N2 C1 N1 176.5(4) . . . . no
C1 N2 C2 C3 0.1(5) . . . . no
C11 N2 C2 C3 -176.2(4) . . . . no
N2 C2 C3 N1 -0.4(5) . . . . no
N1 C4 C5 C6 -2.6(6) . . . . no
N1 C4 C5 C10 176.0(4) . . . . no
C4 C5 C6 C7 179.4(4) . . . . no
C10 C5 C6 C7 0.9(6) . . . . no
C4 C5 C10 C9 -178.7(4) . . . . no
C6 C5 C10 C9 -0.1(6) . . . . no
C5 C6 C7 C8 -0.5(6) . . . . no
C6 C7 C8 C9 -0.6(6) . . . . no
C7 C8 C9 C10 1.4(6) . . . . no
C8 C9 C10 C5 -1.0(6) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C1 H1 O1 0.9500 2.2500 3.155(5) 159.00 . yes
C2 H2 O2 0.9500 2.4900 3.319(5) 146.00 4_546 yes
C4 H4A O4 0.9900 2.3500 3.237(5) 149.00 3_467 yes
C4 H4B O4 0.9900 2.3300 3.278(6) 161.00 . yes
C6 H6 N1 0.9500 2.5000 2.849(5) 102.00 . yes
C7 H7 O2 0.9500 2.4900 3.407(5) 161.00 1_545 yes
C11 H11A O1 0.9800 2.5300 3.347(5) 141.00 1_455 yes
C11 H11B O3 0.9800 2.5900 3.345(5) 134.00 4_646 yes


#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1030632'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 N2, O4 Re'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H15 N2 O4 Re'
_chemical_formula_iupac          ?
_chemical_formula_weight         437.47
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.0076(5)
_cell_length_b                   9.4780(5)
_cell_length_c                   10.6971(6)
_cell_angle_alpha                65.571(2)
_cell_angle_beta                 77.076(2)
_cell_angle_gamma                68.508(2)
_cell_volume                     685.29(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.4813
_cell_measurement_theta_max      25.3769

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.120
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    8.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.239
_exptl_absorpt_correction_T_max  0.453

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             A. Poethig
scanspeed                           3 s per frame
dx                                  35 mm
2518 frames measured in 6 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_monochromator  'MONTEL optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            17956
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2508
# number of observed reflections (> n sig(I))
_reflns_number_gt                2491
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 1997), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0057P)²+0.6392P] 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_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         2508
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0151
_refine_ls_R_factor_gt           0.0150
_refine_ls_wR_factor_ref         0.0387
_refine_ls_wR_factor_gt          0.0386
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_restrained_S_all      1.218
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.112

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

N1 N Uani 0.2142(3) 0.3923(3) 0.7026(2) 1.000 0.0165(7) d . . .
N2 N Uani 0.2306(3) 0.6306(3) 0.5653(2) 1.000 0.0186(7) d . . .
C1 C Uani 0.2034(4) 0.5390(3) 0.6976(3) 1.000 0.0160(8) d . . .
C2 C Uani 0.2593(4) 0.5401(4) 0.4847(3) 1.000 0.0233(9) d . . .
C3 C Uani 0.2491(5) 0.3920(4) 0.5692(3) 1.000 0.0242(10) d . . .
C4 C Uani 0.1956(4) 0.2495(4) 0.8263(3) 1.000 0.0193(8) d . . .
C5 C Uani 0.0187(4) 0.2192(4) 0.8411(3) 1.000 0.0169(8) d . . .
C6 C Uani -0.1405(4) 0.3170(4) 0.8856(3) 1.000 0.0236(9) d . . .
C7 C Uani -0.3002(5) 0.2817(4) 0.9083(3) 1.000 0.0343(10) d . . .
C8 C Uani -0.3019(5) 0.1478(5) 0.8872(4) 1.000 0.0396(11) d . . .
C9 C Uani -0.1454(5) 0.0518(4) 0.8404(4) 1.000 0.0339(11) d . . .
C10 C Uani 0.0150(4) 0.0877(4) 0.8169(3) 1.000 0.0225(9) d . . .
C11 C Uani 0.2257(4) 0.8019(4) 0.5120(3) 1.000 0.0241(9) d . . .
C12 C Uani 0.1680(4) 0.5915(4) 0.8157(3) 1.000 0.0210(9) d . . .
Re1 Re Uani 0.36924(1) 0.19678(1) 0.27676(1) 1.000 0.0158(1) d . . .
O1 O Uani 0.1864(3) 0.1828(3) 0.3962(2) 1.000 0.0279(7) d . . .
O2 O Uani 0.2984(3) 0.2723(3) 0.1138(2) 1.000 0.0298(7) d . . .
O3 O Uani 0.4628(3) 0.3267(3) 0.2893(2) 1.000 0.0306(8) d . . .
O4 O Uani 0.5256(3) 0.0067(3) 0.3079(3) 1.000 0.0399(8) d . . .
H2 H Uiso 0.28200 0.57630 0.38720 1.000 0.0280 c R . .
H3 H Uiso 0.26290 0.30360 0.54310 1.000 0.0290 c R . .
H4A H Uiso 0.20570 0.26670 0.90920 1.000 0.0230 c R . .
H4B H Uiso 0.29550 0.15180 0.82120 1.000 0.0230 c R . .
H6 H Uiso -0.13940 0.40880 0.90060 1.000 0.0280 c R . .
H7 H Uiso -0.40850 0.34920 0.93830 1.000 0.0410 c R . .
H8 H Uiso -0.41080 0.12180 0.90480 1.000 0.0480 c R . .
H9 H Uiso -0.14740 -0.03880 0.82420 1.000 0.0410 c R . .
H10 H Uiso 0.12220 0.02190 0.78420 1.000 0.0270 c R . .
H11A H Uiso 0.32140 0.81920 0.43740 1.000 0.0360 c R . .
H11B H Uiso 0.24400 0.82840 0.58630 1.000 0.0360 c R . .
H11C H Uiso 0.10850 0.87230 0.47660 1.000 0.0360 c R . .
H12A H Uiso 0.24180 0.66070 0.80070 1.000 0.0320 c R . .
H12B H Uiso 0.19840 0.49550 0.90020 1.000 0.0320 c R . .
H12C H Uiso 0.04030 0.65300 0.82450 1.000 0.0320 c R . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O2 1.728(2) . . yes
Re1 O3 1.719(3) . . yes
Re1 O4 1.721(3) . . yes
Re1 O1 1.720(2) . . yes
N1 C4 1.478(4) . . yes
N1 C3 1.392(4) . . yes
N1 C1 1.340(4) . . yes
N2 C2 1.382(4) . . yes
N2 C11 1.470(4) . . yes
N2 C1 1.337(4) . . yes
C1 C12 1.477(4) . . no
C2 C3 1.340(5) . . no
C4 C5 1.508(5) . . no
C5 C6 1.392(5) . . no
C5 C10 1.385(5) . . no
C6 C7 1.383(6) . . no
C7 C8 1.383(6) . . no
C8 C9 1.382(6) . . no
C9 C10 1.391(6) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4B 0.9900 . . no
C4 H4A 0.9900 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11A 0.9800 . . no
C11 H11B 0.9800 . . no
C11 H11C 0.9800 . . no
C12 H12B 0.9800 . . no
C12 H12C 0.9800 . . no
C12 H12A 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O4 109.43(13) . . . yes
O2 Re1 O3 109.56(11) . . . yes
O2 Re1 O4 109.87(13) . . . yes
O3 Re1 O4 109.81(13) . . . yes
O1 Re1 O2 108.96(11) . . . yes
O1 Re1 O3 109.20(12) . . . yes
C1 N1 C3 108.9(2) . . . yes
C1 N1 C4 127.5(2) . . . yes
C3 N1 C4 123.6(3) . . . yes
C1 N2 C11 126.0(2) . . . yes
C1 N2 C2 109.2(3) . . . yes
C2 N2 C11 124.8(2) . . . yes
N1 C1 N2 107.5(2) . . . yes
N1 C1 C12 126.7(3) . . . yes
N2 C1 C12 125.8(3) . . . yes
N2 C2 C3 107.5(3) . . . yes
N1 C3 C2 106.9(3) . . . yes
N1 C4 C5 112.6(3) . . . yes
C4 C5 C6 120.8(3) . . . no
C4 C5 C10 119.8(3) . . . no
C6 C5 C10 119.3(3) . . . no
C5 C6 C7 120.6(3) . . . no
C6 C7 C8 119.8(4) . . . no
C7 C8 C9 120.1(4) . . . no
C8 C9 C10 120.1(4) . . . no
C5 C10 C9 120.1(3) . . . no
N2 C2 H2 126.00 . . . no
C3 C2 H2 126.00 . . . no
N1 C3 H3 127.00 . . . no
C2 C3 H3 127.00 . . . no
C5 C4 H4B 109.00 . . . no
H4A C4 H4B 108.00 . . . no
C5 C4 H4A 109.00 . . . no
N1 C4 H4A 109.00 . . . no
N1 C4 H4B 109.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C9 C8 H8 120.00 . . . no
C7 C8 H8 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C5 C10 H10 120.00 . . . no
C9 C10 H10 120.00 . . . no
H11A C11 H11B 109.00 . . . no
H11A C11 H11C 109.00 . . . no
N2 C11 H11A 109.00 . . . no
N2 C11 H11B 110.00 . . . no
N2 C11 H11C 109.00 . . . no
H11B C11 H11C 110.00 . . . no
H12B C12 H12C 110.00 . . . no
C1 C12 H12A 109.00 . . . no
C1 C12 H12B 109.00 . . . no
C1 C12 H12C 109.00 . . . no
H12A C12 H12B 109.00 . . . no
H12A C12 H12C 110.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 -0.1(4) . . . . no
C3 N1 C1 C12 179.9(3) . . . . no
C4 N1 C1 N2 179.2(3) . . . . no
C4 N1 C1 C12 -0.8(5) . . . . no
C1 N1 C3 C2 0.1(4) . . . . no
C4 N1 C3 C2 -179.2(3) . . . . no
C1 N1 C4 C5 106.2(4) . . . . no
C3 N1 C4 C5 -74.6(4) . . . . no
C2 N2 C1 N1 0.0(4) . . . . no
C2 N2 C1 C12 180.0(3) . . . . no
C11 N2 C1 N1 178.3(3) . . . . no
C11 N2 C1 C12 -1.7(5) . . . . no
C1 N2 C2 C3 0.1(4) . . . . no
C11 N2 C2 C3 -178.2(3) . . . . no
N2 C2 C3 N1 -0.1(4) . . . . no
N1 C4 C5 C6 -75.4(4) . . . . no
N1 C4 C5 C10 107.9(3) . . . . no
C4 C5 C6 C7 -175.4(3) . . . . no
C10 C5 C6 C7 1.4(5) . . . . no
C4 C5 C10 C9 175.1(3) . . . . no
C6 C5 C10 C9 -1.7(5) . . . . no
C5 C6 C7 C8 0.3(5) . . . . no
C6 C7 C8 C9 -1.6(5) . . . . no
C7 C8 C9 C10 1.2(6) . . . . no
C8 C9 C10 C5 0.4(5) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H3 O1 0.9500 2.5700 3.433(4) 152.00 . yes
C4 H4A O2 0.9900 2.4900 3.463(4) 168.00 1_556 yes
C4 H4B O4 0.9900 2.3400 3.228(5) 149.00 2_656 yes
C11 H11B O3 0.9800 2.5900 3.198(4) 120.00 2_666 yes
C11 H11C O1 0.9800 2.5600 3.193(4) 122.00 2_566 yes
C12 H12A O3 0.9800 2.3700 3.174(4) 139.00 2_666 yes
C12 H12B O2 0.9800 2.4300 3.407(4) 173.00 1_556 yes
C12 H12C O2 0.9800 2.5400 3.492(4) 163.00 2_566 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1030633'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_formula_moiety         'C13 H17 N2, O4 Re'
_chemical_formula_sum            'C13 H17 N2 O4 Re'
_chemical_formula_weight         451.50

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z

_cell_length_a                   11.0896(2)
_cell_length_b                   14.4508(2)
_cell_length_c                   18.4542(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2957.35(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    123
_cell_measurement_reflns_used    5132
_cell_measurement_theta_min      2.5648
_cell_measurement_theta_max      25.3338

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    2.028
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    8.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.5216
_exptl_absorpt_correction_T_max  0.7452

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             A. Poethig
scanspeed                           5 s per frame
dx                                  60 mm
1226 frames measured in 5 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            19638
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2712
# number of observed reflections (> n sig(I))
_reflns_number_gt                2201
_reflns_threshold_expression     i>2σ(i)

_computing_data_collection       'APEX II Control Software (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL2013 (Sheldrick, 2013), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     
'W=1/[Σ²(FO²)+(0.0144P)²+2.7196P] 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_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0395
_refine_ls_wR_factor_gt          0.0366
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.098

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N Uani 0.7284(2) 0.9494(2) 0.16253(15) 1.000 0.0176(9) d . . .
N2 N Uani 0.6104(3) 0.8969(2) 0.07950(15) 1.000 0.0187(9) d . . .
C1 C Uani 0.7232(3) 0.8915(2) 0.10586(19) 1.000 0.0187(12) d . . .
C2 C Uani 0.5454(3) 0.9597(2) 0.12015(19) 1.000 0.0218(11) d . . .
C3 C Uani 0.6182(3) 0.9921(2) 0.1720(2) 1.000 0.0213(12) d . . .
C4 C Uani 0.8334(3) 0.9605(2) 0.21164(19) 1.000 0.0209(11) d . . .
C5 C Uani 0.8666(3) 1.0608(3) 0.22188(19) 1.000 0.0188(11) d . . .
C6 C Uani 0.8190(3) 1.1118(2) 0.2788(2) 1.000 0.0247(12) d . . .
C7 C Uani 0.8493(3) 1.2040(3) 0.2874(2) 1.000 0.0283(12) d . . .
C8 C Uani 0.9291(4) 1.2451(3) 0.2406(2) 1.000 0.0303(12) d . . .
C9 C Uani 0.9785(3) 1.1953(3) 0.1842(2) 1.000 0.0277(12) d . . .
C10 C Uani 0.9470(3) 1.1032(2) 0.17455(19) 1.000 0.0221(11) d . . .
C11 C Uani 0.5633(3) 0.8442(3) 0.01761(19) 1.000 0.0263(12) d . . .
C12 C Uani 0.8204(3) 0.8332(2) 0.07672(19) 1.000 0.0227(12) d . . .
C13 C Uani 0.8329(3) 0.7413(3) 0.1173(2) 1.000 0.0270(12) d . . .
Re1 Re Uani 0.81193(2) 1.09206(2) -0.06355(2) 1.000 0.0193(1) d . . .
O1 O Uani 0.7245(2) 0.9963(2) -0.04771(16) 1.000 0.0418(11) d . . .
O2 O Uani 0.9158(3) 1.1066(2) 0.00368(15) 1.000 0.0452(11) d . . .
O3 O Uani 0.8845(2) 1.08022(18) -0.14554(14) 1.000 0.0306(9) d . . .
O4 O Uani 0.7204(2) 1.18793(19) -0.06680(15) 1.000 0.0368(10) d . . .
H2 H Uiso 0.46370 0.97690 0.11260 1.000 0.0260 c RU . .
H3 H Uiso 0.59800 1.03600 0.20840 1.000 0.0260 c RU . .
H4A H Uiso 0.90330 0.92680 0.19130 1.000 0.0250 c RU . .
H4B H Uiso 0.81410 0.93290 0.25930 1.000 0.0250 c RU . .
H6 H Uiso 0.76530 1.08320 0.31210 1.000 0.0300 c RU . .
H7 H Uiso 0.81470 1.23890 0.32570 1.000 0.0340 c RU . .
H8 H Uiso 0.95040 1.30820 0.24710 1.000 0.0370 c RU . .
H9 H Uiso 1.03400 1.22400 0.15210 1.000 0.0330 c RU . .
H10 H Uiso 0.98040 1.06900 0.13540 1.000 0.0260 c RU . .
H11A H Uiso 0.47690 0.85660 0.01210 1.000 0.0400 c RU . .
H11B H Uiso 0.57580 0.77790 0.02600 1.000 0.0400 c RU . .
H11C H Uiso 0.60570 0.86290 -0.02660 1.000 0.0400 c RU . .
H12A H Uiso 0.89760 0.86740 0.07980 1.000 0.0270 c RU . .
H12B H Uiso 0.80420 0.82040 0.02490 1.000 0.0270 c RU . .
H13A H Uiso 0.90080 0.70630 0.09730 1.000 0.0410 c RU . .
H13B H Uiso 0.75850 0.70540 0.11180 1.000 0.0410 c RU . .
H13C H Uiso 0.84730 0.75350 0.16880 1.000 0.0410 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O2 1.706(3) . . yes
Re1 O3 1.722(3) . . yes
Re1 O1 1.715(3) . . yes
Re1 O4 1.719(3) . . yes
N1 C1 1.341(4) . . yes
N1 C3 1.380(4) . . yes
N1 C4 1.484(4) . . yes
N2 C11 1.469(5) . . yes
N2 C2 1.381(4) . . yes
N2 C1 1.344(5) . . yes
C1 C12 1.470(5) . . no
C2 C3 1.337(5) . . no
C4 C5 1.507(5) . . no
C5 C6 1.388(5) . . no
C5 C10 1.390(5) . . no
C6 C7 1.383(5) . . no
C7 C8 1.372(6) . . no
C8 C9 1.379(6) . . no
C9 C10 1.388(5) . . no
C12 C13 1.531(5) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4A 0.9900 . . no
C4 H4B 0.9900 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11A 0.9800 . . no
C11 H11B 0.9800 . . no
C11 H11C 0.9800 . . no
C12 H12A 0.9900 . . no
C12 H12B 0.9900 . . no
C13 H13B 0.9800 . . no
C13 H13C 0.9800 . . no
C13 H13A 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Re1 O4 108.99(13) . . . yes
O2 Re1 O4 108.96(13) . . . yes
O1 Re1 O3 109.50(13) . . . yes
O1 Re1 O4 108.82(12) . . . yes
O1 Re1 O2 110.93(14) . . . yes
O2 Re1 O3 109.61(13) . . . yes
C3 N1 C4 124.7(3) . . . yes
C1 N1 C3 109.9(3) . . . yes
C1 N1 C4 125.3(3) . . . yes
C1 N2 C2 109.1(3) . . . yes
C1 N2 C11 125.6(3) . . . yes
C2 N2 C11 125.3(3) . . . yes
N1 C1 N2 106.6(3) . . . yes
N1 C1 C12 127.7(3) . . . yes
N2 C1 C12 125.7(3) . . . yes
N2 C2 C3 107.7(3) . . . yes
N1 C3 C2 106.7(3) . . . yes
N1 C4 C5 111.8(3) . . . yes
C4 C5 C6 120.9(3) . . . no
C4 C5 C10 120.1(3) . . . no
C6 C5 C10 119.0(4) . . . no
C5 C6 C7 120.4(3) . . . no
C6 C7 C8 120.1(4) . . . no
C7 C8 C9 120.4(4) . . . no
C8 C9 C10 119.8(3) . . . no
C5 C10 C9 120.2(3) . . . no
C1 C12 C13 112.6(3) . . . no
N2 C2 H2 126.00 . . . no
C3 C2 H2 126.00 . . . no
C2 C3 H3 127.00 . . . no
N1 C3 H3 127.00 . . . no
N1 C4 H4A 109.00 . . . no
N1 C4 H4B 109.00 . . . no
C5 C4 H4A 109.00 . . . no
C5 C4 H4B 109.00 . . . no
H4A C4 H4B 108.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
C10 C9 H9 120.00 . . . no
C8 C9 H9 120.00 . . . no
C5 C10 H10 120.00 . . . no
C9 C10 H10 120.00 . . . no
N2 C11 H11B 109.00 . . . no
N2 C11 H11A 109.00 . . . no
H11A C11 H11B 109.00 . . . no
H11A C11 H11C 109.00 . . . no
N2 C11 H11C 110.00 . . . no
H11B C11 H11C 109.00 . . . no
C13 C12 H12A 109.00 . . . no
C13 C12 H12B 109.00 . . . no
C1 C12 H12A 109.00 . . . no
C1 C12 H12B 109.00 . . . no
H12A C12 H12B 108.00 . . . no
H13B C13 H13C 109.00 . . . no
C12 C13 H13A 109.00 . . . no
C12 C13 H13B 109.00 . . . no
C12 C13 H13C 109.00 . . . no
H13A C13 H13B 110.00 . . . no
H13A C13 H13C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 -0.2(4) . . . . no
C4 N1 C1 N2 175.1(3) . . . . no
C3 N1 C1 C12 179.4(3) . . . . no
C4 N1 C1 C12 -5.3(5) . . . . no
C4 N1 C3 C2 -175.5(3) . . . . no
C1 N1 C4 C5 130.7(3) . . . . no
C1 N1 C3 C2 -0.2(4) . . . . no
C3 N1 C4 C5 -54.7(4) . . . . no
C2 N2 C1 N1 0.5(4) . . . . no
C11 N2 C1 N1 -179.2(3) . . . . no
C1 N2 C2 C3 -0.7(4) . . . . no
C11 N2 C2 C3 179.1(3) . . . . no
C2 N2 C1 C12 -179.1(3) . . . . no
C11 N2 C1 C12 1.2(5) . . . . no
N1 C1 C12 C13 83.8(4) . . . . no
N2 C1 C12 C13 -96.7(4) . . . . no
N2 C2 C3 N1 0.5(4) . . . . no
N1 C4 C5 C6 92.2(4) . . . . no
N1 C4 C5 C10 -88.6(4) . . . . no
C4 C5 C6 C7 -179.5(3) . . . . no
C10 C5 C6 C7 1.3(5) . . . . no
C4 C5 C10 C9 -179.5(3) . . . . no
C6 C5 C10 C9 -0.2(5) . . . . no
C5 C6 C7 C8 -1.6(5) . . . . no
C6 C7 C8 C9 0.8(6) . . . . no
C7 C8 C9 C10 0.2(6) . . . . no
C8 C9 C10 C5 -0.5(5) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C2 H2 O1 0.9500 2.4400 3.339(4) 159.00 5_675 yes
C4 H4A O3 0.9900 2.5000 3.409(4) 152.00 5_775 yes
C7 H7 O4 0.9500 2.4800 3.424(5) 173.00 8_575 yes
C10 H10 O2 0.9500 2.5900 3.173(4) 120.00 . yes
C11 H11A O4 0.9800 2.4900 3.307(4) 140.00 5_675 yes
C11 H11B O2 0.9800 2.5100 3.451(5) 161.00 7_645 yes
C11 H11C O1 0.9800 2.3700 3.079(5) 129.00 . yes
C12 H12B O4 0.9900 2.5700 3.410(4) 143.00 7_645 yes


#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound4
_database_code_depnum_ccdc_archive 'CCDC 1030634'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA


_chemical_formula_moiety         'C14 H19 N2, O4 Re'
_chemical_formula_sum            'C14 H19 N2 O4 Re'
_chemical_formula_weight         465.52
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   12.2997(3)
_cell_length_b                   8.3808(2)
_cell_length_c                   16.4451(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.587(1)
_cell_angle_gamma                90
_cell_volume                     1576.28(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9042
_cell_measurement_theta_min      2.6640
_cell_measurement_theta_max      31.7591

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.149
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    7.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_T_max  0.7465

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             A. Poethig
scanspeed                           10 s per frame
dx                                  60 mm
6673 frames measured in 19 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            77447
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         33.20
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             6016
# number of observed reflections (> n sig(I))
_reflns_number_gt                5165
_reflns_threshold_expression     i>2σ(i)

_computing_data_collection       'APEX II Control Software (Bruker, 2013)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL2013 (Sheldrick, 2013), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     
'W=1/[Σ²(FO²)+(0.0144P)²+1.1023P] 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_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         6016
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0182
_refine_ls_wR_factor_ref         0.0367
_refine_ls_wR_factor_gt          0.0347
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.999
_refine_diff_density_rms         0.101

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N Uani 0.24957(13) 0.82178(17) 0.55074(9) 1.000 0.0187(4) d . . .
N2 N Uani 0.35477(13) 0.79471(18) 0.68744(9) 1.000 0.0205(4) d . . .
C1 C Uani 0.32502(15) 0.7231(2) 0.60898(11) 1.000 0.0191(4) d . . .
C2 C Uani 0.23104(17) 0.9552(2) 0.59263(12) 1.000 0.0237(5) d . . .
C3 C Uani 0.29738(17) 0.9380(2) 0.67830(12) 1.000 0.0236(5) d . . .
C4 C Uani 0.19207(16) 0.7941(2) 0.45596(11) 1.000 0.0216(5) d . . .
C5 C Uani 0.27063(16) 0.8245(2) 0.40552(11) 1.000 0.0223(5) d . . .
C6 C Uani 0.26258(19) 0.7262(3) 0.33592(14) 1.000 0.0317(6) d . . .
C7 C Uani 0.3284(2) 0.7567(3) 0.28478(15) 1.000 0.0362(7) d . . .
C8 C Uani 0.4050(2) 0.8826(3) 0.30419(14) 1.000 0.0360(7) d . . .
C9 C Uani 0.4139(3) 0.9799(3) 0.37318(18) 1.000 0.0540(10) d . . .
C10 C Uani 0.3461(3) 0.9520(3) 0.42355(16) 1.000 0.0472(9) d . . .
C11 C Uani 0.43143(19) 0.7330(3) 0.77275(12) 1.000 0.0316(6) d . . .
C12 C Uani 0.36686(17) 0.5673(2) 0.58704(12) 1.000 0.0246(5) d . . .
C13 C Uani 0.3335(2) 0.4246(2) 0.63087(15) 1.000 0.0340(6) d . . .
C14 C Uani 0.4980(2) 0.5720(3) 0.60368(19) 1.000 0.0466(8) d . . .
Re1 Re Uani 0.53004(2) 1.21403(2) 0.91056(2) 1.000 0.0201(1) d . . .
O1 O Uani 0.63663(16) 1.0823(2) 0.91041(11) 1.000 0.0437(6) d . . .
O2 O Uani 0.39405(14) 1.1334(2) 0.85339(10) 1.000 0.0396(5) d . . .
O3 O Uani 0.54635(14) 1.38832(18) 0.86082(11) 1.000 0.0361(5) d . . .
O4 O Uani 0.54402(14) 1.2547(2) 1.01667(10) 1.000 0.0352(5) d . . .
H2 H Uiso 0.18120 1.04250 0.56640 1.000 0.0280 c RU . .
H3 H Uiso 0.30320 1.01140 0.72380 1.000 0.0280 c RU . .
H4A H Uiso 0.12270 0.86430 0.43280 1.000 0.0260 c RU . .
H4B H Uiso 0.16430 0.68220 0.44620 1.000 0.0260 c RU . .
H6 H Uiso 0.21150 0.63680 0.32300 1.000 0.0380 c RU . .
H7 H Uiso 0.32040 0.69020 0.23610 1.000 0.0440 c RU . .
H8 H Uiso 0.45150 0.90200 0.27010 1.000 0.0430 c RU . .
H9 H Uiso 0.46680 1.06730 0.38690 1.000 0.0650 c RU . .
H10 H Uiso 0.35210 1.02150 0.47060 1.000 0.0570 c RU . .
H11A H Uiso 0.44250 0.81510 0.81750 1.000 0.0470 c RU . .
H11B H Uiso 0.50730 0.70420 0.77020 1.000 0.0470 c RU . .
H11C H Uiso 0.39560 0.63840 0.78750 1.000 0.0470 c RU . .
H12 H Uiso 0.32570 0.55220 0.52260 1.000 0.0290 c RU . .
H13A H Uiso 0.35250 0.32550 0.60740 1.000 0.0510 c RU . .
H13B H Uiso 0.24950 0.42780 0.61920 1.000 0.0510 c RU . .
H13C H Uiso 0.37720 0.42900 0.69410 1.000 0.0510 c RU . .
H14A H Uiso 0.52070 0.47290 0.58260 1.000 0.0700 c RU . .
H14B H Uiso 0.54250 0.58340 0.66650 1.000 0.0700 c RU . .
H14C H Uiso 0.51450 0.66290 0.57250 1.000 0.0700 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O3 1.7215(16) . . yes
Re1 O4 1.7234(16) . . yes
Re1 O1 1.7146(19) . . yes
Re1 O2 1.7266(18) . . yes
N1 C1 1.345(2) . . yes
N1 C4 1.474(2) . . yes
N1 C2 1.376(2) . . yes
N2 C1 1.346(2) . . yes
N2 C3 1.373(2) . . yes
N2 C11 1.467(2) . . yes
C1 C12 1.496(2) . . no
C2 C3 1.351(3) . . no
C4 C5 1.509(3) . . no
C5 C10 1.374(4) . . no
C5 C6 1.384(3) . . no
C6 C7 1.389(3) . . no
C7 C8 1.372(4) . . no
C8 C9 1.369(4) . . no
C9 C10 1.395(5) . . no
C12 C13 1.528(3) . . no
C12 C14 1.534(4) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4A 0.9900 . . no
C4 H4B 0.9900 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11B 0.9800 . . no
C11 H11C 0.9800 . . no
C11 H11A 0.9800 . . no
C12 H12 1.0000 . . no
C13 H13A 0.9800 . . no
C13 H13B 0.9800 . . no
C13 H13C 0.9800 . . no
C14 H14B 0.9800 . . no
C14 H14C 0.9800 . . no
C14 H14A 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O2 109.59(8) . . . yes
O1 Re1 O3 108.83(9) . . . yes
O1 Re1 O4 109.71(8) . . . yes
O2 Re1 O3 109.41(8) . . . yes
O2 Re1 O4 110.15(8) . . . yes
O3 Re1 O4 109.13(8) . . . yes
C2 N1 C4 123.65(15) . . . yes
C1 N1 C2 109.96(14) . . . yes
C1 N1 C4 126.39(15) . . . yes
C3 N2 C11 122.47(16) . . . yes
C1 N2 C11 127.74(16) . . . yes
C1 N2 C3 109.73(15) . . . yes
N2 C1 C12 128.63(16) . . . yes
N1 C1 N2 106.35(15) . . . yes
N1 C1 C12 125.01(15) . . . yes
N1 C2 C3 106.72(16) . . . yes
N2 C3 C2 107.24(15) . . . yes
N1 C4 C5 113.56(16) . . . yes
C4 C5 C6 119.26(18) . . . no
C4 C5 C10 122.07(19) . . . no
C6 C5 C10 118.6(2) . . . no
C5 C6 C7 120.7(2) . . . no
C6 C7 C8 120.3(2) . . . no
C7 C8 C9 119.3(3) . . . no
C8 C9 C10 120.6(3) . . . no
C5 C10 C9 120.4(2) . . . no
C13 C12 C14 112.52(18) . . . no
C1 C12 C13 113.17(17) . . . no
C1 C12 C14 111.54(17) . . . no
C3 C2 H2 127.00 . . . no
N1 C2 H2 127.00 . . . no
N2 C3 H3 126.00 . . . no
C2 C3 H3 126.00 . . . no
H4A C4 H4B 108.00 . . . no
N1 C4 H4A 109.00 . . . no
N1 C4 H4B 109.00 . . . no
C5 C4 H4A 109.00 . . . no
C5 C4 H4B 109.00 . . . no
C5 C6 H6 120.00 . . . no
C7 C6 H6 120.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C5 C10 H10 120.00 . . . no
C9 C10 H10 120.00 . . . no
H11B C11 H11C 109.00 . . . no
N2 C11 H11A 109.00 . . . no
N2 C11 H11B 109.00 . . . no
N2 C11 H11C 109.00 . . . no
H11A C11 H11B 110.00 . . . no
H11A C11 H11C 109.00 . . . no
C13 C12 H12 106.00 . . . no
C14 C12 H12 106.00 . . . no
C1 C12 H12 106.00 . . . no
H13A C13 H13B 109.00 . . . no
H13A C13 H13C 109.00 . . . no
C12 C13 H13A 109.00 . . . no
C12 C13 H13B 109.00 . . . no
C12 C13 H13C 109.00 . . . no
H13B C13 H13C 110.00 . . . no
H14B C14 H14C 109.00 . . . no
C12 C14 H14A 109.00 . . . no
C12 C14 H14B 109.00 . . . no
C12 C14 H14C 109.00 . . . no
H14A C14 H14B 110.00 . . . no
H14A C14 H14C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -0.5(2) . . . . no
C2 N1 C1 C12 -179.23(18) . . . . no
C4 N1 C1 N2 -179.54(17) . . . . no
C4 N1 C1 C12 1.7(3) . . . . no
C1 N1 C2 C3 0.4(2) . . . . no
C4 N1 C2 C3 179.55(18) . . . . no
C1 N1 C4 C5 -77.8(2) . . . . no
C2 N1 C4 C5 103.2(2) . . . . no
C3 N2 C1 N1 0.3(2) . . . . no
C3 N2 C1 C12 179.01(19) . . . . no
C11 N2 C1 N1 177.47(19) . . . . no
C11 N2 C1 C12 -3.8(3) . . . . no
C1 N2 C3 C2 0.0(2) . . . . no
C11 N2 C3 C2 -177.37(19) . . . . no
N1 C1 C12 C13 -118.3(2) . . . . no
N1 C1 C12 C14 113.6(2) . . . . no
N2 C1 C12 C13 63.2(3) . . . . no
N2 C1 C12 C14 -64.9(3) . . . . no
N1 C2 C3 N2 -0.3(2) . . . . no
N1 C4 C5 C6 142.39(18) . . . . no
N1 C4 C5 C10 -41.0(3) . . . . no
C4 C5 C6 C7 176.0(2) . . . . no
C10 C5 C6 C7 -0.7(3) . . . . no
C4 C5 C10 C9 -177.4(2) . . . . no
C6 C5 C10 C9 -0.8(4) . . . . no
C5 C6 C7 C8 1.8(4) . . . . no
C6 C7 C8 C9 -1.5(4) . . . . no
C7 C8 C9 C10 0.0(4) . . . . no
C8 C9 C10 C5 1.1(4) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C2 H2 O4 0.9500 2.3200 3.263(3) 171.00 4_474 yes
C3 H3 O2 0.9500 2.2500 3.141(2) 155.00 . yes
C4 H4A O3 0.9900 2.4000 3.268(2) 146.00 4_474 yes
C4 H4B O1 0.9900 2.2900 3.256(2) 166.00 4_464 yes


#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1030635'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 F5 N2, O4 Re'
_chemical_formula_sum            'C11 H8 F5 N2 O4 Re'
_chemical_formula_weight         513.40

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'
F F 0.0171 0.0103 ' 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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   8.0372(2)
_cell_length_b                   10.1535(2)
_cell_length_c                   17.2223(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.5967(8)
_cell_angle_gamma                90
_cell_volume                     1405.36(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.5343
_cell_measurement_theta_max      25.4083
_cell_special_details            
;
;

_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.427
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    8.726

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.179
_exptl_absorpt_correction_T_max  0.274

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             A. Poethig
scanspeed                           10 s per frame
dx                                  50
1850 frames measured in 9 data sets
phi-scan with delta_phi         = 0.5
omega-scans with delta_omega    = 0.5
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            38559
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0082
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_full        25.41
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2592
# number of observed reflections (> n sig(I))
_reflns_number_gt                2565
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0092P)²+2.3397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall

_refine_ls_extinction_method     shelxl
_refine_ls_extinction_coef       0.00093(7)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^
_refine_ls_number_reflns         2592
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0138
_refine_ls_R_factor_gt           0.0135
_refine_ls_wR_factor_ref         0.0317
_refine_ls_wR_factor_gt          0.0316
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_restrained_S_all      1.241
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.066

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

F1 F Uani 0.52986(19) 0.31342(16) 0.17169(10) 1.000 0.0279(5) d . . .
F2 F Uani 0.3785(2) 0.47533(17) 0.27095(10) 1.000 0.0321(5) d . . .
F3 F Uani 0.0411(2) 0.46845(17) 0.28540(9) 1.000 0.0296(5) d . . .
F4 F Uani -0.1402(2) 0.29469(18) 0.20050(10) 1.000 0.0293(5) d . . .
F5 F Uani 0.0135(2) 0.12898(16) 0.10147(9) 1.000 0.0251(5) d . . .
N1 N Uani 0.3067(3) 0.1698(2) -0.00512(13) 1.000 0.0165(6) d . . .
N2 N Uani 0.2618(3) 0.2898(2) -0.10627(13) 1.000 0.0182(6) d . . .
C1 C Uani 0.3179(3) 0.2908(3) -0.03372(16) 1.000 0.0182(8) d . . .
C2 C Uani 0.2126(4) 0.1632(3) -0.12437(17) 1.000 0.0217(8) d . . .
C3 C Uani 0.2409(3) 0.0884(3) -0.06150(16) 1.000 0.0194(8) d . . .
C4 C Uani 0.3573(4) 0.1308(3) 0.07388(16) 1.000 0.0202(8) d . . .
C5 C Uani 0.2753(3) 0.2184(3) 0.13235(14) 1.000 0.0160(7) d . . .
C6 C Uani 0.3632(3) 0.3074(3) 0.17717(16) 1.000 0.0182(8) d . . .
C7 C Uani 0.2874(3) 0.3916(3) 0.22816(15) 1.000 0.0207(8) d . . .
C8 C Uani 0.1174(3) 0.3878(3) 0.23583(15) 1.000 0.0201(8) d . . .
C9 C Uani 0.0257(3) 0.2992(3) 0.19244(15) 1.000 0.0199(8) d . . .
C10 C Uani 0.1045(3) 0.2165(3) 0.14210(15) 1.000 0.0176(7) d . . .
C11 C Uani 0.2525(4) 0.4060(3) -0.15628(19) 1.000 0.0282(10) d . . .
Re1 Re Uani 0.21568(1) 0.67180(1) 0.06258(1) 1.000 0.0187(1) d . . .
O1 O Uani 0.0655(3) 0.6425(2) -0.00682(13) 1.000 0.0387(8) d . . .
O2 O Uani 0.3634(3) 0.54786(19) 0.06232(12) 1.000 0.0269(6) d . . .
O3 O Uani 0.1249(3) 0.6772(2) 0.15250(13) 1.000 0.0336(7) d . . .
O4 O Uani 0.3122(3) 0.8204(2) 0.04305(15) 1.000 0.0368(7) d . . .
H1 H Uiso 0.353(4) 0.364(3) -0.0055(17) 1.000 0.020(8) d . . .
H2 H Uiso 0.165(4) 0.140(3) -0.171(2) 1.000 0.026(8) d . . .
H3 H Uiso 0.227(4) 0.005(4) -0.0501(19) 1.000 0.030(9) d . . .
H4A H Uiso 0.327(4) 0.046(3) 0.0790(18) 1.000 0.024(8) d . . .
H4B H Uiso 0.478(4) 0.138(3) 0.0796(18) 1.000 0.024(8) d . . .
H11A H Uiso 0.229(5) 0.471(5) -0.128(3) 1.000 0.057(13) d . . .
H11B H Uiso 0.353(6) 0.415(4) -0.179(3) 1.000 0.061(13) d . . .
H11C H Uiso 0.173(5) 0.391(4) -0.197(2) 1.000 0.052(11) d . . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O4 1.731(2) . . yes
Re1 O3 1.720(2) . . yes
Re1 O1 1.716(2) . . yes
Re1 O2 1.730(2) . . yes
F1 C6 1.345(3) . . yes
F2 C7 1.338(3) . . yes
F3 C8 1.337(3) . . yes
F4 C9 1.343(3) . . yes
F5 C10 1.343(3) . . yes
N1 C1 1.327(4) . . yes
N1 C3 1.377(4) . . yes
N1 C4 1.470(4) . . yes
N2 C2 1.380(4) . . yes
N2 C11 1.462(4) . . yes
N2 C1 1.324(4) . . yes
C2 C3 1.340(4) . . no
C4 C5 1.501(4) . . no
C5 C10 1.385(3) . . no
C5 C6 1.379(4) . . no
C6 C7 1.373(4) . . no
C7 C8 1.375(3) . . no
C8 C9 1.378(4) . . no
C9 C10 1.367(4) . . no
C1 H1 0.93(3) . . no
C2 H2 0.92(3) . . no
C3 H3 0.88(4) . . no
C4 H4A 0.90(3) . . no
C4 H4B 0.98(3) . . no
C11 H11B 0.91(5) . . no
C11 H11C 0.96(4) . . no
C11 H11A 0.84(5) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O3 109.32(11) . . . yes
O1 Re1 O4 109.22(11) . . . yes
O2 Re1 O3 108.85(10) . . . yes
O2 Re1 O4 108.94(11) . . . yes
O3 Re1 O4 110.03(11) . . . yes
O1 Re1 O2 110.48(10) . . . yes
C1 N1 C3 108.7(2) . . . yes
C1 N1 C4 125.0(2) . . . yes
C3 N1 C4 126.3(2) . . . yes
C2 N2 C11 127.3(2) . . . yes
C1 N2 C11 124.4(2) . . . yes
C1 N2 C2 108.3(2) . . . yes
N1 C1 N2 108.6(2) . . . yes
N2 C2 C3 107.4(3) . . . yes
N1 C3 C2 106.9(3) . . . yes
N1 C4 C5 110.0(2) . . . yes
C6 C5 C10 116.4(2) . . . no
C4 C5 C6 122.6(2) . . . no
C4 C5 C10 121.1(3) . . . no
F1 C6 C5 119.7(2) . . . yes
F1 C6 C7 117.7(2) . . . yes
C5 C6 C7 122.6(2) . . . no
F2 C7 C6 120.3(2) . . . yes
C6 C7 C8 119.5(3) . . . no
F2 C7 C8 120.2(2) . . . yes
C7 C8 C9 119.5(3) . . . no
F3 C8 C7 120.5(2) . . . yes
F3 C8 C9 120.0(2) . . . yes
F4 C9 C8 119.5(2) . . . yes
F4 C9 C10 120.8(2) . . . yes
C8 C9 C10 119.7(2) . . . no
F5 C10 C5 118.8(2) . . . yes
F5 C10 C9 118.9(2) . . . yes
C5 C10 C9 122.3(3) . . . no
N2 C1 H1 126.7(18) . . . no
N1 C1 H1 124.6(18) . . . no
C3 C2 H2 129(2) . . . no
N2 C2 H2 124(2) . . . no
N1 C3 H3 118(2) . . . no
C2 C3 H3 135(2) . . . no
C5 C4 H4A 112(2) . . . no
C5 C4 H4B 109.3(18) . . . no
N1 C4 H4A 106(2) . . . no
N1 C4 H4B 109.8(18) . . . no
H4A C4 H4B 109(3) . . . no
H11B C11 H11C 107(4) . . . no
N2 C11 H11A 108(3) . . . no
N2 C11 H11B 107(3) . . . no
N2 C11 H11C 110(2) . . . no
H11A C11 H11B 112(4) . . . no
H11A C11 H11C 113(4) . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 0.0(3) . . . . no
C4 N1 C1 N2 179.8(3) . . . . no
C1 N1 C4 C5 52.9(4) . . . . no
C3 N1 C4 C5 -127.2(3) . . . . no
C1 N1 C3 C2 -0.1(3) . . . . no
C4 N1 C3 C2 -180.0(3) . . . . no
C2 N2 C1 N1 0.2(3) . . . . no
C1 N2 C2 C3 -0.3(3) . . . . no
C11 N2 C2 C3 -179.1(3) . . . . no
C11 N2 C1 N1 179.0(3) . . . . no
N2 C2 C3 N1 0.2(3) . . . . no
N1 C4 C5 C6 -111.7(3) . . . . no
N1 C4 C5 C10 66.2(3) . . . . no
C4 C5 C6 F1 -3.1(4) . . . . no
C4 C5 C6 C7 177.0(3) . . . . no
C10 C5 C6 F1 179.0(2) . . . . no
C10 C5 C6 C7 -0.9(4) . . . . no
C4 C5 C10 F5 3.9(4) . . . . no
C4 C5 C10 C9 -177.1(3) . . . . no
C6 C5 C10 F5 -178.1(2) . . . . no
C6 C5 C10 C9 0.9(4) . . . . no
F1 C6 C7 F2 -0.6(4) . . . . no
F1 C6 C7 C8 -179.5(2) . . . . no
C5 C6 C7 F2 179.3(3) . . . . no
C5 C6 C7 C8 0.4(4) . . . . no
F2 C7 C8 F3 0.7(4) . . . . no
F2 C7 C8 C9 -178.7(3) . . . . no
C6 C7 C8 F3 179.7(3) . . . . no
C6 C7 C8 C9 0.2(4) . . . . no
F3 C8 C9 F4 -0.1(4) . . . . no
F3 C8 C9 C10 -179.7(3) . . . . no
C7 C8 C9 F4 179.4(3) . . . . no
C7 C8 C9 C10 -0.2(4) . . . . no
F4 C9 C10 F5 -1.0(4) . . . . no
F4 C9 C10 C5 -180.0(3) . . . . no
C8 C9 C10 F5 178.7(2) . . . . no
C8 C9 C10 C5 -0.4(4) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C1 H1 O2 0.93(3) 2.20(3) 3.110(4) 165(3) . yes
C3 H3 O4 0.88(4) 2.56(4) 3.310(4) 145(3) 1_545 yes
C3 H3 F5 0.88(4) 2.52(4) 3.082(3) 123(3) 3_555 yes
C4 H4A O4 0.90(3) 2.38(3) 3.216(4) 156(3) 1_545 yes
C4 H4B F1 0.98(3) 2.42(3) 2.855(3) 107(2) . yes

#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound6
_database_code_depnum_ccdc_archive 'CCDC 1030636'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F5 N2, O4 Re'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H10 F5 N2 O4 Re'
_chemical_formula_iupac          ?
_chemical_formula_weight         527.43
_chemical_compound_source        'see text'

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'
F F 0.0171 0.0103 ' 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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   13.1970(2)
_cell_length_b                   9.4355(2)
_cell_length_c                   24.8443(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.309(1)
_cell_angle_gamma                90
_cell_volume                     3074.88(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.7332
_cell_measurement_theta_max      25.2805

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.279
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1984
_exptl_absorpt_coefficient_mu    7.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.230
_exptl_absorpt_correction_T_max  0.474

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             A. Poethig
scanspeed                           5 s per frame
dx                                  35 mm
5762 frames measured in 11 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            46517
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2833
# number of observed reflections (> n sig(I))
_reflns_number_gt                2472
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 1997), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0132P)²+10.6345P] 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_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         2833
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0168
_refine_ls_wR_factor_ref         0.0367
_refine_ls_wR_factor_gt          0.0352
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.644
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.094

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

F1 F Uani 0.89927(15) 0.7097(2) 0.73873(8) 1.000 0.0318(7) d . . .
F2 F Uani 0.76299(17) 0.8818(3) 0.77718(8) 1.000 0.0396(8) d . . .
F3 F Uani 0.57711(17) 0.9189(3) 0.72116(10) 1.000 0.0486(9) d . . .
F4 F Uani 0.52390(14) 0.7701(3) 0.62861(9) 1.000 0.0368(8) d . . .
F5 F Uani 0.65971(15) 0.5929(2) 0.59046(8) 1.000 0.0277(7) d . . .
N1 N Uani 0.8964(2) 0.6015(3) 0.59158(10) 1.000 0.0161(8) d . . .
N2 N Uani 0.9783(2) 0.7170(3) 0.53540(11) 1.000 0.0163(8) d . . .
C1 C Uani 0.9675(2) 0.7015(3) 0.58799(13) 1.000 0.0163(10) d . . .
C2 C Uani 0.9122(3) 0.6266(4) 0.50534(14) 1.000 0.0202(11) d . . .
C3 C Uani 0.8611(3) 0.5547(4) 0.54010(14) 1.000 0.0213(11) d . . .
C4 C Uani 0.8607(3) 0.5485(4) 0.64173(13) 1.000 0.0194(11) d . . .
C5 C Uani 0.7845(2) 0.6471(4) 0.66310(13) 1.000 0.0165(10) d . . .
C6 C Uani 0.8066(2) 0.7216(4) 0.71047(13) 1.000 0.0193(10) d . . .
C7 C Uani 0.7375(3) 0.8101(4) 0.73099(14) 1.000 0.0248(11) d . . .
C8 C Uani 0.6427(3) 0.8267(4) 0.70311(15) 1.000 0.0275(11) d . . .
C9 C Uani 0.6167(2) 0.7528(4) 0.65588(14) 1.000 0.0242(11) d . . .
C10 C Uani 0.6872(3) 0.6641(4) 0.63692(14) 1.000 0.0202(11) d . . .
C11 C Uani 1.0494(3) 0.8139(4) 0.51294(15) 1.000 0.0242(11) d . . .
C12 C Uani 1.0219(3) 0.7809(4) 0.63324(14) 1.000 0.0236(11) d . . .
Re1 Re Uani 0.78201(1) 1.08188(1) 0.60873(1) 1.000 0.0190(1) d . . .
O1 O Uani 0.8364(2) 1.0674(3) 0.67413(11) 1.000 0.0471(10) d . . .
O2 O Uani 0.78387(18) 1.2556(3) 0.58710(10) 1.000 0.0294(8) d . . .
O3 O Uani 0.8476(2) 0.9782(3) 0.56760(12) 1.000 0.0401(10) d . . .
O4 O Uani 0.65724(18) 1.0249(3) 0.60460(10) 1.000 0.0262(8) d . . .
H2 H Uiso 0.90440 0.61720 0.46700 1.000 0.0240 c R . .
H3 H Uiso 0.81030 0.48470 0.53120 1.000 0.0260 c R . .
H4A H Uiso 0.91990 0.53680 0.66950 1.000 0.0230 c R . .
H4B H Uiso 0.82900 0.45420 0.63480 1.000 0.0230 c R . .
H11A H Uiso 1.03630 0.81410 0.47330 1.000 0.0360 c R . .
H11B H Uiso 1.11950 0.78270 0.52380 1.000 0.0360 c R . .
H11C H Uiso 1.04010 0.90980 0.52670 1.000 0.0360 c R . .
H12A H Uiso 1.08440 0.82160 0.62180 1.000 0.0350 c R . .
H12B H Uiso 1.03930 0.71690 0.66390 1.000 0.0350 c R . .
H12C H Uiso 0.97810 0.85730 0.64420 1.000 0.0350 c R . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O2 1.726(3) . . yes
Re1 O3 1.716(3) . . yes
Re1 O4 1.725(2) . . yes
Re1 O1 1.708(3) . . yes
F1 C6 1.346(3) . . yes
F2 C7 1.343(4) . . yes
F3 C8 1.339(5) . . yes
F4 C9 1.343(4) . . yes
F5 C10 1.350(4) . . yes
N1 C3 1.385(4) . . yes
N1 C4 1.468(4) . . yes
N1 C1 1.341(4) . . yes
N2 C1 1.338(4) . . yes
N2 C2 1.380(5) . . yes
N2 C11 1.464(5) . . yes
C1 C12 1.471(5) . . no
C2 C3 1.338(5) . . no
C4 C5 1.509(5) . . no
C5 C6 1.374(5) . . no
C5 C10 1.384(5) . . no
C6 C7 1.375(5) . . no
C7 C8 1.371(5) . . no
C8 C9 1.376(5) . . no
C9 C10 1.373(5) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4A 0.9900 . . no
C4 H4B 0.9900 . . no
C11 H11A 0.9800 . . no
C11 H11B 0.9800 . . no
C11 H11C 0.9800 . . no
C12 H12B 0.9800 . . no
C12 H12C 0.9800 . . no
C12 H12A 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O4 109.29(12) . . . yes
O2 Re1 O3 109.31(13) . . . yes
O2 Re1 O4 108.89(12) . . . yes
O3 Re1 O4 109.13(13) . . . yes
O1 Re1 O2 110.68(13) . . . yes
O1 Re1 O3 109.52(13) . . . yes
C1 N1 C3 109.3(3) . . . yes
C1 N1 C4 126.1(3) . . . yes
C3 N1 C4 124.7(3) . . . yes
C1 N2 C11 125.6(3) . . . yes
C1 N2 C2 109.4(3) . . . yes
C2 N2 C11 125.0(3) . . . yes
N1 C1 N2 107.0(3) . . . yes
N1 C1 C12 126.5(3) . . . yes
N2 C1 C12 126.5(3) . . . yes
N2 C2 C3 107.3(3) . . . yes
N1 C3 C2 107.0(3) . . . yes
N1 C4 C5 112.2(3) . . . yes
C4 C5 C6 122.0(3) . . . no
C4 C5 C10 121.8(3) . . . no
C6 C5 C10 116.2(3) . . . no
F1 C6 C5 119.9(3) . . . yes
F1 C6 C7 117.3(3) . . . yes
C5 C6 C7 122.8(3) . . . no
F2 C7 C8 120.2(3) . . . yes
F2 C7 C6 120.6(3) . . . yes
C6 C7 C8 119.2(3) . . . no
F3 C8 C7 119.5(3) . . . yes
F3 C8 C9 120.4(3) . . . yes
C7 C8 C9 120.1(3) . . . no
F4 C9 C10 121.1(3) . . . yes
C8 C9 C10 119.1(3) . . . no
F4 C9 C8 119.8(3) . . . yes
F5 C10 C9 117.9(3) . . . yes
F5 C10 C5 119.5(3) . . . yes
C5 C10 C9 122.6(3) . . . no
C3 C2 H2 126.00 . . . no
N2 C2 H2 126.00 . . . no
N1 C3 H3 126.00 . . . no
C2 C3 H3 127.00 . . . no
N1 C4 H4B 109.00 . . . no
N1 C4 H4A 109.00 . . . no
C5 C4 H4B 109.00 . . . no
H4A C4 H4B 108.00 . . . no
C5 C4 H4A 109.00 . . . no
H11A C11 H11B 110.00 . . . no
H11A C11 H11C 109.00 . . . no
N2 C11 H11A 110.00 . . . no
N2 C11 H11B 109.00 . . . no
N2 C11 H11C 109.00 . . . no
H11B C11 H11C 109.00 . . . no
H12B C12 H12C 109.00 . . . no
C1 C12 H12A 109.00 . . . no
C1 C12 H12B 109.00 . . . no
C1 C12 H12C 109.00 . . . no
H12A C12 H12B 110.00 . . . no
H12A C12 H12C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 -0.7(4) . . . . no
C4 N1 C1 N2 179.2(3) . . . . no
C3 N1 C1 C12 178.2(3) . . . . no
C4 N1 C1 C12 -1.8(5) . . . . no
C1 N1 C3 C2 0.5(4) . . . . no
C4 N1 C3 C2 -179.4(3) . . . . no
C1 N1 C4 C5 79.7(4) . . . . no
C3 N1 C4 C5 -100.4(4) . . . . no
C1 N2 C2 C3 -0.4(4) . . . . no
C11 N2 C2 C3 179.3(3) . . . . no
C2 N2 C1 C12 -178.3(3) . . . . no
C2 N2 C1 N1 0.7(4) . . . . no
C11 N2 C1 N1 -179.0(3) . . . . no
C11 N2 C1 C12 2.1(5) . . . . no
N2 C2 C3 N1 -0.1(4) . . . . no
N1 C4 C5 C6 -112.1(4) . . . . no
N1 C4 C5 C10 70.0(4) . . . . no
C4 C5 C6 F1 1.3(5) . . . . no
C4 C5 C6 C7 -178.9(3) . . . . no
C10 C5 C6 F1 179.3(3) . . . . no
C10 C5 C6 C7 -0.9(5) . . . . no
C4 C5 C10 F5 -1.2(5) . . . . no
C4 C5 C10 C9 179.7(3) . . . . no
C6 C5 C10 F5 -179.3(3) . . . . no
C6 C5 C10 C9 1.7(5) . . . . no
F1 C6 C7 F2 0.5(5) . . . . no
F1 C6 C7 C8 179.2(3) . . . . no
C5 C6 C7 F2 -179.3(3) . . . . no
C5 C6 C7 C8 -0.7(6) . . . . no
F2 C7 C8 F3 2.5(5) . . . . no
F2 C7 C8 C9 -179.8(3) . . . . no
C6 C7 C8 F3 -176.1(3) . . . . no
C6 C7 C8 C9 1.5(6) . . . . no
F3 C8 C9 F4 -2.0(5) . . . . no
F3 C8 C9 C10 176.9(3) . . . . no
C7 C8 C9 F4 -179.7(3) . . . . no
C7 C8 C9 C10 -0.8(6) . . . . no
F4 C9 C10 F5 -1.1(5) . . . . no
F4 C9 C10 C5 178.0(3) . . . . no
C8 C9 C10 F5 -180.0(3) . . . . no
C8 C9 C10 C5 -0.9(6) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C2 H2 O4 0.9500 2.3000 3.130(4) 145.00 7_666 yes
C4 H4A F1 0.9900 2.4100 2.848(4) 106.00 . yes
C4 H4B O2 0.9900 2.2600 3.195(5) 157.00 1_545 yes
C11 H11B O2 0.9800 2.5500 3.467(5) 156.00 5_545 yes
C12 H12B F1 0.9800 2.4700 3.305(4) 143.00 2_756 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound7
_database_code_depnum_ccdc_archive 'CCDC 1030637'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 F5 N2, O4 Re'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H12 F5 N2 O4 Re'
_chemical_formula_iupac          ?
_chemical_formula_weight         541.46
_chemical_compound_source        'see text'

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'
F F 0.0171 0.0103 ' 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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_Int_Tables_number      33

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,1/2+y,1/2+z
4 1/2+x,1/2-y,z

_cell_length_a                   10.3689(3)
_cell_length_b                   18.6571(7)
_cell_length_c                   8.4223(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1629.32(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.1831
_cell_measurement_theta_max      28.9696
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.207
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    7.533
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.330
_exptl_absorpt_correction_T_max  0.547

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             M. Kaposi
scanspeed                           20 s per frame
dx                                  40 mm
3676 frames measured in 9 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            46035
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3328
# number of observed reflections (> n sig(I))
_reflns_number_gt                2686
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 1997), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0062P)²]         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_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.308(10)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration ?

_refine_ls_number_reflns         3328
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0478
_refine_ls_wR_factor_gt          0.0441
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.925
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.110

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

F1 F Uani 0.7202(3) 0.38673(19) 0.8119(4) 1.000 0.0317(12) d . . .
F2 F Uani 0.5615(3) 0.28198(19) 0.9148(4) 1.000 0.0333(12) d . . .
F3 F Uani 0.4284(3) 0.2020(2) 0.7026(5) 1.000 0.0350(14) d . . .
F4 F Uani 0.4587(3) 0.22452(19) 0.3853(5) 1.000 0.0417(14) d . . .
F5 F Uani 0.6247(3) 0.32459(19) 0.2823(4) 1.000 0.0383(12) d . . .
N1 N Uani 0.7140(4) 0.4890(3) 0.5314(5) 1.000 0.0217(17) d . . .
N2 N Uani 0.6971(3) 0.6003(2) 0.5944(13) 1.000 0.0243(14) d . . .
C1 C Uani 0.7809(5) 0.5460(3) 0.5831(12) 1.000 0.0213(19) d . . .
C2 C Uani 0.5765(5) 0.5764(3) 0.5511(7) 1.000 0.027(2) d . . .
C3 C Uani 0.5863(5) 0.5071(3) 0.5103(7) 1.000 0.026(2) d . . .
C4 C Uani 0.7676(5) 0.4179(3) 0.4868(8) 1.000 0.024(2) d . . .
C5 C Uani 0.6783(7) 0.3587(4) 0.5452(8) 1.000 0.022(2) d . . .
C6 C Uani 0.6581(7) 0.3465(4) 0.7025(8) 1.000 0.020(3) d . . .
C7 C Uani 0.5763(7) 0.2938(4) 0.7597(9) 1.000 0.022(2) d . . .
C8 C Uani 0.5113(6) 0.2520(3) 0.6501(10) 1.000 0.025(3) d . . .
C9 C Uani 0.5262(7) 0.2637(4) 0.4920(10) 1.000 0.025(3) d . . .
C10 C Uani 0.6136(7) 0.3155(4) 0.4422(9) 1.000 0.027(3) d . . .
C11 C Uani 0.7292(5) 0.6745(3) 0.6365(8) 1.000 0.035(3) d . . .
C12 C Uani 0.9208(4) 0.5495(3) 0.6188(11) 1.000 0.027(2) d . . .
C13 C Uani 1.0001(6) 0.5851(3) 0.4896(8) 1.000 0.039(2) d . . .
Re1 Re Uani 0.75818(2) 0.59050(1) 1.09736(9) 1.000 0.0206(1) d . . .
O1 O Uani 0.6451(4) 0.6046(2) 0.9531(5) 1.000 0.0330(16) d . . .
O2 O Uani 0.7404(4) 0.5065(3) 1.1744(6) 1.000 0.0440(17) d . . .
O3 O Uani 0.7395(3) 0.6537(2) 1.2447(5) 1.000 0.0387(17) d . . .
O4 O Uani 0.9099(3) 0.5987(2) 1.0149(5) 1.000 0.0327(16) d . . .
H2 H Uiso 0.49970 0.60420 0.55020 1.000 0.0320 c R . .
H3 H Uiso 0.51890 0.47670 0.47410 1.000 0.0310 c R . .
H4A H Uiso 0.85410 0.41190 0.53460 1.000 0.0290 c R . .
H4B H Uiso 0.77660 0.41490 0.37000 1.000 0.0290 c R . .
H11A H Uiso 0.65360 0.69770 0.68380 1.000 0.0520 c R . .
H11B H Uiso 0.75510 0.70070 0.54070 1.000 0.0520 c R . .
H11C H Uiso 0.80040 0.67470 0.71300 1.000 0.0520 c R . .
H12A H Uiso 0.95350 0.50020 0.63540 1.000 0.0320 c R . .
H12B H Uiso 0.93310 0.57620 0.71920 1.000 0.0320 c R . .
H13A H Uiso 1.09100 0.58630 0.52170 1.000 0.0590 c R . .
H13B H Uiso 0.96920 0.63420 0.47300 1.000 0.0590 c R . .
H13C H Uiso 0.99150 0.55790 0.39070 1.000 0.0590 c R . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O2 1.706(6) . . yes
Re1 O3 1.723(4) . . yes
Re1 O1 1.709(4) . . yes
Re1 O4 1.726(3) . . yes
F1 C6 1.352(8) . . yes
F2 C7 1.334(8) . . yes
F3 C8 1.343(7) . . yes
F4 C9 1.353(9) . . yes
F5 C10 1.362(8) . . yes
N1 C4 1.487(8) . . yes
N1 C3 1.378(7) . . yes
N1 C1 1.342(8) . . yes
N2 C2 1.377(7) . . yes
N2 C11 1.467(7) . . yes
N2 C1 1.338(7) . . yes
C1 C12 1.483(7) . . no
C2 C3 1.342(8) . . no
C4 C5 1.523(9) . . no
C5 C10 1.361(10) . . no
C5 C6 1.361(10) . . no
C6 C7 1.385(10) . . no
C7 C8 1.384(10) . . no
C8 C9 1.358(12) . . no
C9 C10 1.390(11) . . no
C12 C13 1.517(10) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4B 0.9900 . . no
C4 H4A 0.9900 . . no
C11 H11A 0.9800 . . no
C11 H11B 0.9800 . . no
C11 H11C 0.9800 . . no
C12 H12A 0.9900 . . no
C12 H12B 0.9900 . . no
C13 H13B 0.9800 . . no
C13 H13C 0.9800 . . no
C13 H13A 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Re1 O4 109.36(17) . . . yes
O2 Re1 O4 109.45(19) . . . yes
O1 Re1 O3 109.24(18) . . . yes
O1 Re1 O4 109.0(2) . . . yes
O1 Re1 O2 109.7(2) . . . yes
O2 Re1 O3 110.0(2) . . . yes
C3 N1 C4 123.1(5) . . . yes
C1 N1 C3 110.1(5) . . . yes
C1 N1 C4 126.6(4) . . . yes
C1 N2 C2 109.0(5) . . . yes
C1 N2 C11 125.8(4) . . . yes
C2 N2 C11 125.1(4) . . . yes
N1 C1 N2 106.7(5) . . . yes
N1 C1 C12 127.3(5) . . . yes
N2 C1 C12 126.0(5) . . . yes
N2 C2 C3 108.1(5) . . . yes
N1 C3 C2 106.0(5) . . . yes
N1 C4 C5 109.8(5) . . . yes
C4 C5 C6 122.0(6) . . . no
C4 C5 C10 121.6(6) . . . no
C6 C5 C10 116.5(7) . . . no
C5 C6 C7 123.5(7) . . . no
F1 C6 C7 116.7(6) . . . yes
F1 C6 C5 119.8(6) . . . yes
F2 C7 C6 121.9(6) . . . yes
F2 C7 C8 120.3(6) . . . yes
C6 C7 C8 117.8(7) . . . no
F3 C8 C7 118.9(7) . . . yes
F3 C8 C9 120.5(6) . . . yes
C7 C8 C9 120.5(6) . . . no
F4 C9 C10 120.8(7) . . . yes
F4 C9 C8 120.4(6) . . . yes
C8 C9 C10 118.8(7) . . . no
F5 C10 C5 121.0(6) . . . yes
F5 C10 C9 116.1(6) . . . yes
C5 C10 C9 122.8(7) . . . no
C1 C12 C13 113.8(7) . . . no
N2 C2 H2 126.00 . . . no
C3 C2 H2 126.00 . . . no
C2 C3 H3 127.00 . . . no
N1 C3 H3 127.00 . . . no
C5 C4 H4A 110.00 . . . no
N1 C4 H4A 110.00 . . . no
N1 C4 H4B 110.00 . . . no
C5 C4 H4B 110.00 . . . no
H4A C4 H4B 108.00 . . . no
N2 C11 H11B 109.00 . . . no
N2 C11 H11A 109.00 . . . no
H11A C11 H11B 109.00 . . . no
H11A C11 H11C 109.00 . . . no
N2 C11 H11C 109.00 . . . no
H11B C11 H11C 109.00 . . . no
C13 C12 H12A 109.00 . . . no
C13 C12 H12B 109.00 . . . no
C1 C12 H12A 109.00 . . . no
C1 C12 H12B 109.00 . . . no
H12A C12 H12B 108.00 . . . no
H13B C13 H13C 109.00 . . . no
C12 C13 H13A 109.00 . . . no
C12 C13 H13B 110.00 . . . no
C12 C13 H13C 110.00 . . . no
H13A C13 H13B 109.00 . . . no
H13A C13 H13C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 -0.3(9) . . . . no
C4 N1 C1 N2 174.1(7) . . . . no
C3 N1 C1 C12 -179.4(8) . . . . no
C4 N1 C1 C12 -5.0(13) . . . . no
C4 N1 C3 C2 -175.0(5) . . . . no
C1 N1 C4 C5 140.4(7) . . . . no
C1 N1 C3 C2 -0.3(7) . . . . no
C3 N1 C4 C5 -45.9(7) . . . . no
C2 N2 C1 N1 0.8(11) . . . . no
C11 N2 C1 N1 -175.8(8) . . . . no
C1 N2 C2 C3 -1.0(10) . . . . no
C11 N2 C2 C3 175.6(8) . . . . no
C2 N2 C1 C12 179.9(9) . . . . no
C11 N2 C1 C12 3.3(17) . . . . no
N1 C1 C12 C13 101.9(9) . . . . no
N2 C1 C12 C13 -77.1(12) . . . . no
N2 C2 C3 N1 0.8(8) . . . . no
N1 C4 C5 C6 -65.3(8) . . . . no
N1 C4 C5 C10 114.2(7) . . . . no
C4 C5 C6 F1 -1.3(11) . . . . no
C4 C5 C6 C7 179.1(7) . . . . no
C10 C5 C6 F1 179.2(6) . . . . no
C10 C5 C6 C7 -0.4(11) . . . . no
C4 C5 C10 F5 -1.2(11) . . . . no
C4 C5 C10 C9 -176.4(7) . . . . no
C6 C5 C10 F5 178.3(6) . . . . no
C6 C5 C10 C9 3.1(11) . . . . no
F1 C6 C7 F2 -1.5(10) . . . . no
F1 C6 C7 C8 179.8(6) . . . . no
C5 C6 C7 F2 178.1(7) . . . . no
C5 C6 C7 C8 -0.5(11) . . . . no
F2 C7 C8 F3 3.4(9) . . . . no
F2 C7 C8 C9 -179.9(6) . . . . no
C6 C7 C8 F3 -178.0(6) . . . . no
C6 C7 C8 C9 -1.2(10) . . . . no
F3 C8 C9 F4 -0.8(10) . . . . no
F3 C8 C9 C10 -179.5(6) . . . . no
C7 C8 C9 F4 -177.5(6) . . . . no
C7 C8 C9 C10 3.8(10) . . . . no
F4 C9 C10 F5 1.0(10) . . . . no
F4 C9 C10 C5 176.4(7) . . . . no
C8 C9 C10 F5 179.7(6) . . . . no
C8 C9 C10 C5 -4.9(11) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C2 H2 F2 0.9500 2.4900 3.217(7) 133.00 2_664 yes
C3 H3 O1 0.9500 2.2900 3.214(7) 165.00 2_664 yes
C4 H4A O4 0.9900 2.4600 3.367(6) 152.00 2_764 yes
C4 H4B F5 0.9900 2.4200 2.862(7) 106.00 . yes
C4 H4B O2 0.9900 2.4000 3.120(8) 129.00 1_554 yes
C11 H11A F4 0.9800 2.5200 3.426(7) 154.00 2_665 yes
C12 H12A O4 0.9900 2.5400 3.390(7) 144.00 2_764 yes
C12 H12B O4 0.9900 2.5400 3.462(10) 155.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound8
_database_code_depnum_ccdc_archive 'CCDC 1030638'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 F5 N2, O4 Re'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C14 H14 F5 N2 O4 Re'
_chemical_formula_iupac          ?
_chemical_formula_weight         555.48
_chemical_compound_source        'see text'

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'
F F 0.0171 0.0103 ' 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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   9.6255(3)
_cell_length_b                   11.6206(4)
_cell_length_c                   15.4559(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1728.81(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9480
_cell_measurement_theta_min      2.6356
_cell_measurement_theta_max      33.0972

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.210
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    7.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'

_exptl_absorpt_correction_T_min  0.168
_exptl_absorpt_correction_T_max  0.314

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             M. Kaposi
scanspeed                           5 s per frame
dx                                  35 mm
4384 frames measured in 12 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_monochromator  'MONTEL optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            85286
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         33.11
_diffrn_reflns_theta_full        33.11
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             6533
# number of observed reflections (> n sig(I))
_reflns_number_gt                6286
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 1997), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'


#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0213P)²+0.7069P] 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_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.043(5)


_chemical_absolute_configuration unk

_refine_ls_number_reflns         6533
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0474
_refine_ls_wR_factor_gt          0.0470
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.293
_refine_diff_density_min         -1.351
_refine_diff_density_rms         0.092

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

F1 F Uani -0.0259(2) 0.47956(14) -0.02976(12) 1.000 0.0418(5) d . . .
F2 F Uani -0.15413(18) 0.52290(16) 0.12262(12) 1.000 0.0422(5) d . . .
F3 F Uani -0.1478(2) 0.73606(17) 0.19069(10) 1.000 0.0397(5) d . . .
F4 F Uani 0.10140(17) 0.86959(14) -0.05118(11) 1.000 0.0333(4) d . . .
F5 F Uani 0.1036(2) 0.65297(17) -0.11700(11) 1.000 0.0409(5) d . . .
N1 N Uani 0.11113(19) 0.96263(16) 0.14076(13) 1.000 0.0213(5) d . . .
N2 N Uani 0.2900(2) 1.06063(18) 0.18206(13) 1.000 0.0252(5) d . . .
C1 C Uani 0.1660(2) 1.06918(18) 0.14272(16) 1.000 0.0221(5) d . . .
C2 C Uani 0.3130(2) 0.9479(2) 0.20617(16) 1.000 0.0269(7) d . . .
C3 C Uani 0.2013(3) 0.8872(2) 0.18115(15) 1.000 0.0252(6) d . . .
C4 C Uani -0.0269(2) 0.9298(2) 0.10714(17) 1.000 0.0266(7) d . . .
C5 C Uani -0.0242(2) 0.8091(2) 0.07079(15) 1.000 0.0217(6) d . . .
C6 C Uani 0.0384(2) 0.7841(2) -0.00734(15) 1.000 0.0233(6) d . . .
C7 C Uani 0.0396(3) 0.6745(2) -0.04159(16) 1.000 0.0270(7) d . . .
C8 C Uani -0.0254(3) 0.5864(2) 0.00259(17) 1.000 0.0281(7) d . . .
C9 C Uani -0.0900(3) 0.6082(2) 0.08035(17) 1.000 0.0289(7) d . . .
C10 C Uani -0.0867(3) 0.7179(2) 0.11339(16) 1.000 0.0267(6) d . . .
C11 C Uani 0.1070(3) 1.1781(2) 0.10698(18) 1.000 0.0319(7) d . . .
C12 C Uani 0.1265(5) 1.1851(3) 0.0080(2) 1.000 0.0492(12) d . . .
C13 C Uani -0.0440(3) 1.2004(3) 0.1330(2) 1.000 0.0413(9) d . . .
C14 C Uani 0.3911(3) 1.1531(3) 0.1957(2) 1.000 0.0402(9) d . . .
Re1 Re Uani -0.21791(1) 0.98840(1) -0.14783(1) 1.000 0.0260(1) d . . .
O1 O Uani -0.2287(3) 1.0023(4) -0.03815(16) 1.000 0.0884(14) d . . .
O2 O Uani -0.0879(3) 1.0754(2) -0.1836(2) 1.000 0.0585(9) d . . .
O3 O Uani -0.3737(2) 1.0290(3) -0.19254(15) 1.000 0.0652(11) d . . .
O4 O Uani -0.1771(4) 0.8519(2) -0.1742(3) 1.000 0.1020(16) d . . .
H2 H Uiso 0.39280 0.91870 0.23500 1.000 0.0320 c R . .
H3 H Uiso 0.18690 0.80720 0.18970 1.000 0.0300 c R . .
H4A H Uiso -0.05520 0.98440 0.06130 1.000 0.0320 c R . .
H4B H Uiso -0.09620 0.93420 0.15440 1.000 0.0320 c R . .
H11 H Uiso 0.16300 1.24230 0.13230 1.000 0.0380 c R . .
H12A H Uiso 0.07180 1.12440 -0.02000 1.000 0.0740 c R . .
H12B H Uiso 0.22500 1.17480 -0.00620 1.000 0.0740 c R . .
H12C H Uiso 0.09520 1.26040 -0.01270 1.000 0.0740 c R . .
H13A H Uiso -0.06410 1.28290 0.12840 1.000 0.0620 c R . .
H13B H Uiso -0.05860 1.17520 0.19280 1.000 0.0620 c R . .
H13C H Uiso -0.10610 1.15750 0.09450 1.000 0.0620 c R . .
H14A H Uiso 0.40280 1.19670 0.14190 1.000 0.0600 c R . .
H14B H Uiso 0.48060 1.11980 0.21280 1.000 0.0600 c R . .
H14C H Uiso 0.35780 1.20460 0.24140 1.000 0.0600 c R . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O3 1.717(2) . . yes
Re1 O4 1.684(3) . . yes
Re1 O1 1.706(3) . . yes
Re1 O2 1.701(3) . . yes
F1 C8 1.339(3) . . yes
F2 C9 1.338(3) . . yes
F3 C10 1.348(3) . . yes
F4 C6 1.347(3) . . yes
F5 C7 1.342(3) . . yes
N1 C4 1.477(3) . . yes
N1 C1 1.347(3) . . yes
N1 C3 1.383(3) . . yes
N2 C14 1.465(4) . . yes
N2 C2 1.380(3) . . yes
N2 C1 1.343(3) . . yes
C1 C11 1.493(3) . . no
C2 C3 1.343(3) . . no
C4 C5 1.511(3) . . no
C5 C6 1.381(3) . . no
C5 C10 1.385(3) . . no
C6 C7 1.379(3) . . no
C7 C8 1.381(4) . . no
C8 C9 1.377(4) . . no
C9 C10 1.374(3) . . no
C11 C12 1.543(4) . . no
C11 C13 1.530(4) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4B 0.9900 . . no
C4 H4A 0.9900 . . no
C11 H11 1.0000 . . no
C12 H12A 0.9800 . . no
C12 H12B 0.9800 . . no
C12 H12C 0.9800 . . no
C13 H13A 0.9800 . . no
C13 H13B 0.9800 . . no
C13 H13C 0.9800 . . no
C14 H14B 0.9800 . . no
C14 H14C 0.9800 . . no
C14 H14A 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O2 108.15(16) . . . yes
O1 Re1 O3 108.70(13) . . . yes
O1 Re1 O4 110.1(2) . . . yes
O2 Re1 O3 110.39(14) . . . yes
O2 Re1 O4 108.03(16) . . . yes
O3 Re1 O4 111.41(18) . . . yes
C3 N1 C4 124.05(19) . . . yes
C1 N1 C3 109.06(19) . . . yes
C1 N1 C4 126.76(19) . . . yes
C2 N2 C14 123.4(2) . . . yes
C1 N2 C14 127.0(2) . . . yes
C1 N2 C2 109.58(19) . . . yes
N2 C1 C11 124.6(2) . . . yes
N1 C1 N2 106.90(19) . . . yes
N1 C1 C11 128.5(2) . . . yes
N2 C2 C3 107.01(19) . . . yes
N1 C3 C2 107.4(2) . . . yes
N1 C4 C5 110.80(17) . . . yes
C4 C5 C6 121.9(2) . . . no
C4 C5 C10 121.7(2) . . . no
C6 C5 C10 116.4(2) . . . no
F4 C6 C7 119.0(2) . . . yes
F4 C6 C5 118.8(2) . . . yes
C5 C6 C7 122.3(2) . . . no
F5 C7 C6 120.6(2) . . . yes
F5 C7 C8 120.0(2) . . . yes
C6 C7 C8 119.4(2) . . . no
C7 C8 C9 120.0(2) . . . no
F1 C8 C9 119.7(2) . . . yes
F1 C8 C7 120.3(2) . . . yes
F2 C9 C8 119.9(2) . . . yes
F2 C9 C10 121.1(2) . . . yes
C8 C9 C10 119.0(2) . . . no
F3 C10 C5 119.4(2) . . . yes
F3 C10 C9 117.7(2) . . . yes
C5 C10 C9 122.9(2) . . . no
C1 C11 C13 114.1(2) . . . no
C1 C11 C12 111.4(2) . . . no
C12 C11 C13 111.5(3) . . . no
N2 C2 H2 127.00 . . . no
C3 C2 H2 126.00 . . . no
C2 C3 H3 126.00 . . . no
N1 C3 H3 126.00 . . . no
C5 C4 H4A 109.00 . . . no
C5 C4 H4B 109.00 . . . no
N1 C4 H4B 109.00 . . . no
N1 C4 H4A 110.00 . . . no
H4A C4 H4B 108.00 . . . no
C12 C11 H11 106.00 . . . no
C1 C11 H11 106.00 . . . no
C13 C11 H11 106.00 . . . no
C11 C12 H12C 109.00 . . . no
C11 C12 H12A 110.00 . . . no
C11 C12 H12B 109.00 . . . no
H12A C12 H12C 109.00 . . . no
H12B C12 H12C 109.00 . . . no
H12A C12 H12B 109.00 . . . no
H13A C13 H13B 109.00 . . . no
H13A C13 H13C 109.00 . . . no
C11 C13 H13A 110.00 . . . no
C11 C13 H13B 109.00 . . . no
C11 C13 H13C 109.00 . . . no
H13B C13 H13C 109.00 . . . no
H14B C14 H14C 110.00 . . . no
N2 C14 H14A 109.00 . . . no
N2 C14 H14B 109.00 . . . no
N2 C14 H14C 110.00 . . . no
H14A C14 H14B 109.00 . . . no
H14A C14 H14C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 1.3(3) . . . . no
C4 N1 C1 N2 177.2(2) . . . . no
C3 N1 C1 C11 179.7(2) . . . . no
C4 N1 C1 C11 -4.4(4) . . . . no
C3 N1 C4 C5 -35.5(3) . . . . no
C1 N1 C3 C2 -1.3(3) . . . . no
C4 N1 C3 C2 -177.4(2) . . . . no
C1 N1 C4 C5 149.1(2) . . . . no
C14 N2 C1 N1 177.0(2) . . . . no
C2 N2 C1 C11 -179.3(2) . . . . no
C14 N2 C1 C11 -1.5(4) . . . . no
C2 N2 C1 N1 -0.8(3) . . . . no
C1 N2 C2 C3 0.0(3) . . . . no
C14 N2 C2 C3 -177.9(2) . . . . no
N2 C1 C11 C12 100.3(3) . . . . no
N1 C1 C11 C12 -77.9(4) . . . . no
N1 C1 C11 C13 49.5(4) . . . . no
N2 C1 C11 C13 -132.3(3) . . . . no
N2 C2 C3 N1 0.8(3) . . . . no
N1 C4 C5 C6 -74.1(3) . . . . no
N1 C4 C5 C10 107.1(2) . . . . no
C4 C5 C6 F4 1.5(3) . . . . no
C4 C5 C6 C7 -179.0(2) . . . . no
C10 C5 C6 F4 -179.6(2) . . . . no
C10 C5 C6 C7 -0.2(3) . . . . no
C4 C5 C10 F3 -2.2(4) . . . . no
C4 C5 C10 C9 177.7(2) . . . . no
C6 C5 C10 F3 179.0(2) . . . . no
C6 C5 C10 C9 -1.2(4) . . . . no
F4 C6 C7 F5 0.6(4) . . . . no
F4 C6 C7 C8 -179.6(2) . . . . no
C5 C6 C7 F5 -178.8(2) . . . . no
C5 C6 C7 C8 1.0(4) . . . . no
F5 C7 C8 F1 -0.5(4) . . . . no
F5 C7 C8 C9 179.4(3) . . . . no
C6 C7 C8 F1 179.7(2) . . . . no
C6 C7 C8 C9 -0.4(4) . . . . no
F1 C8 C9 F2 -0.7(4) . . . . no
F1 C8 C9 C10 179.0(3) . . . . no
C7 C8 C9 F2 179.3(3) . . . . no
C7 C8 C9 C10 -1.0(4) . . . . no
F2 C9 C10 F3 1.4(4) . . . . no
F2 C9 C10 C5 -178.5(2) . . . . no
C8 C9 C10 F3 -178.4(2) . . . . no
C8 C9 C10 C5 1.8(4) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C2 H2 O2 0.9500 2.2600 3.159(4) 157.00 2_575 yes
C3 H3 O4 0.9500 2.2800 3.017(4) 134.00 3_565 yes
C4 H4A O1 0.9900 2.2800 3.086(4) 138.00 . yes
C4 H4B F3 0.9900 2.4200 2.844(3) 105.00 . yes
C4 H4B O3 0.9900 2.4200 3.276(3) 144.00 2_475 yes
C14 H14B O4 0.9800 2.6000 3.410(5) 140.00 2_575 yes
C14 H14C F3 0.9800 2.3100 3.082(4) 135.00 4_555 yes



#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound9
_database_code_depnum_ccdc_archive 'CCDC 1030639'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N2, O4 Re'
_chemical_formula_sum            'C17 H17 N2 O4 Re'
_chemical_formula_weight         499.54
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   7.7420(3)
_cell_length_b                   9.7001(3)
_cell_length_c                   12.1493(4)
_cell_angle_alpha                77.4846(14)
_cell_angle_beta                 85.3240(14)
_cell_angle_gamma                72.6881(13)
_cell_volume                     850.22(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.5364
_cell_measurement_theta_max      25.4827

_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_method    none
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    7.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_T_max  0.413

_exptl_special_details           
;
Diffractometer operator             A. Poethig
scanspeed                           10 s per frame
dx                                  35.1
2823 frames measured in 9 data sets 
phi-scan with delta_phi         = 0.5
omega-scans with delta_omega    = 0.5
;
#===============================================================================

# 7. EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16 # 8 for binned mode

# number of measured reflections (redundant set)
_diffrn_reflns_number            29374
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.51
_diffrn_reflns_theta_full        25.51
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3159
# number of observed reflections (> n sig(I))
_reflns_number_gt                3078
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1998)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'PLATON (Spek, 2008)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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      sigma
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.6583P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3159
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0524
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.373
_refine_diff_density_min         -1.405
_refine_diff_density_rms         0.114

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

N1 N Uani 0.7435(4) 0.3047(3) 0.0119(2) 1.000 0.0248(8) d . . .
N2 N Uani 0.7974(4) 0.1932(3) 0.1847(2) 1.000 0.0222(7) d . . .
C1 C Uani 0.7544(4) 0.1795(4) 0.0849(3) 1.000 0.0233(9) d . . .
C2 C Uani 0.7832(5) 0.4017(4) 0.0665(3) 1.000 0.0297(10) d . . .
C3 C Uani 0.8184(5) 0.3317(4) 0.1735(3) 1.000 0.0295(10) d . . .
C4 C Uani 0.6899(5) 0.3349(4) -0.1059(3) 1.000 0.0315(10) d . . .
C5 C Uani 0.8341(5) 0.3749(4) -0.1871(3) 1.000 0.0247(9) d . . .
C6 C Uani 0.7876(5) 0.4980(4) -0.2739(3) 1.000 0.0283(10) d . . .
C7 C Uani 0.9175(5) 0.5307(4) -0.3516(3) 1.000 0.0312(10) d . . .
C8 C Uani 1.0950(5) 0.4432(4) -0.3421(3) 1.000 0.0303(10) d . . .
C9 C Uani 1.1425(5) 0.3219(4) -0.2539(3) 1.000 0.0298(10) d . . .
C10 C Uani 1.0121(5) 0.2884(4) -0.1772(3) 1.000 0.0287(9) d . . .
C11 C Uani 0.8307(5) 0.0740(4) 0.2869(3) 1.000 0.0259(9) d . . .
C12 C Uani 0.7566(5) 0.1341(3) 0.3915(3) 1.000 0.0242(9) d . . .
C13 C Uani 0.5773(5) 0.1509(4) 0.4242(3) 1.000 0.0305(10) d . . .
C14 C Uani 0.5108(5) 0.2060(5) 0.5202(3) 1.000 0.0373(11) d . . .
C15 C Uani 0.6226(6) 0.2469(4) 0.5828(3) 1.000 0.0377(11) d . . .
C16 C Uani 0.8012(5) 0.2297(4) 0.5500(3) 1.000 0.0323(10) d . . .
C17 C Uani 0.8687(5) 0.1730(4) 0.4554(3) 1.000 0.0280(10) d . . .
Re1 Re Uani 0.31170(1) 0.10475(1) 0.13959(1) 1.000 0.0244(1) d . . .
O1 O Uani 0.3435(4) 0.2622(3) 0.0568(3) 1.000 0.0458(9) d . . .
O2 O Uani 0.2255(4) 0.1403(3) 0.2691(2) 1.000 0.0395(8) d . . .
O3 O Uani 0.1628(3) 0.0438(3) 0.0783(2) 1.000 0.0361(8) d . . .
O4 O Uani 0.5171(3) -0.0287(3) 0.1572(2) 1.000 0.0393(8) d . . .
H1 H Uiso 0.731(5) 0.101(4) 0.073(3) 1.000 0.025(9) d . . .
H2 H Uiso 0.784(6) 0.487(6) 0.030(4) 1.000 0.039(12) d . . .
H3 H Uiso 0.852(6) 0.361(5) 0.227(4) 1.000 0.042(12) d . . .
H4A H Uiso 0.590(7) 0.404(6) -0.117(4) 1.000 0.040(12) d . . .
H4B H Uiso 0.671(5) 0.242(5) -0.119(3) 1.000 0.034(10) d . . .
H6 H Uiso 0.675(6) 0.553(5) -0.275(3) 1.000 0.034(11) d . . .
H7 H Uiso 0.886(6) 0.609(5) -0.415(4) 1.000 0.034(10) d . . .
H8 H Uiso 1.177(5) 0.466(4) -0.389(3) 1.000 0.027(9) d . . .
H9 H Uiso 1.258(6) 0.263(5) -0.241(3) 1.000 0.035(10) d . . .
H10 H Uiso 1.051(6) 0.214(5) -0.114(4) 1.000 0.045(12) d . . .
H11A H Uiso 0.768(5) 0.003(4) 0.275(3) 1.000 0.022(9) d . . .
H11B H Uiso 0.951(6) 0.027(5) 0.292(3) 1.000 0.032(11) d . . .
H13 H Uiso 0.499(6) 0.121(5) 0.381(3) 1.000 0.036(10) d . . .
H14 H Uiso 0.395(8) 0.221(6) 0.538(5) 1.000 0.057(15) d . . .
H15 H Uiso 0.572(6) 0.293(5) 0.643(4) 1.000 0.036(11) d . . .
H16 H Uiso 0.869(6) 0.249(5) 0.595(4) 1.000 0.043(12) d . . .
H17 H Uiso 0.984(6) 0.160(5) 0.436(3) 1.000 0.036(11) d . . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O1 1.710(3) . . yes
Re1 O2 1.723(3) . . yes
Re1 O3 1.723(3) . . yes
Re1 O4 1.721(3) . . yes
N1 C1 1.324(5) . . yes
N1 C2 1.377(5) . . yes
N1 C4 1.466(4) . . yes
N2 C3 1.377(5) . . yes
N2 C11 1.483(4) . . yes
N2 C1 1.327(4) . . yes
C2 C3 1.338(5) . . no
C4 C5 1.511(5) . . no
C5 C10 1.383(6) . . no
C5 C6 1.389(5) . . no
C6 C7 1.382(5) . . no
C7 C8 1.383(6) . . no
C8 C9 1.389(5) . . no
C9 C10 1.380(5) . . no
C11 C12 1.512(5) . . no
C12 C13 1.384(6) . . no
C12 C17 1.389(5) . . no
C13 C14 1.386(5) . . no
C14 C15 1.388(6) . . no
C15 C16 1.379(6) . . no
C16 C17 1.379(5) . . no
C1 H1 0.88(4) . . no
C2 H2 0.85(5) . . no
C3 H3 0.85(5) . . no
C4 H4B 1.00(5) . . no
C4 H4A 0.86(6) . . no
C6 H6 0.88(5) . . no
C7 H7 0.95(5) . . no
C8 H8 0.86(4) . . no
C9 H9 0.91(5) . . no
C10 H10 0.93(5) . . no
C11 H11A 0.99(4) . . no
C11 H11B 0.91(5) . . no
C13 H13 0.97(4) . . no
C14 H14 0.88(6) . . no
C15 H15 0.94(5) . . no
C16 H16 0.87(5) . . no
C17 H17 0.88(5) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O2 109.16(14) . . . yes
O1 Re1 O3 110.74(14) . . . yes
O1 Re1 O4 108.76(14) . . . yes
O2 Re1 O3 109.11(13) . . . yes
O2 Re1 O4 109.38(13) . . . yes
O3 Re1 O4 109.67(13) . . . yes
C2 N1 C4 126.4(3) . . . yes
C1 N1 C2 108.7(3) . . . yes
C1 N1 C4 124.9(3) . . . yes
C3 N2 C11 126.8(3) . . . yes
C1 N2 C11 124.9(3) . . . yes
C1 N2 C3 108.1(3) . . . yes
N1 C1 N2 108.7(3) . . . yes
N1 C2 C3 106.9(3) . . . yes
N2 C3 C2 107.6(3) . . . yes
N1 C4 C5 112.1(3) . . . yes
C6 C5 C10 119.5(4) . . . no
C4 C5 C6 119.9(3) . . . no
C4 C5 C10 120.6(3) . . . no
C5 C6 C7 120.0(4) . . . no
C6 C7 C8 120.3(3) . . . no
C7 C8 C9 119.7(4) . . . no
C8 C9 C10 119.9(4) . . . no
C5 C10 C9 120.6(3) . . . no
N2 C11 C12 111.1(3) . . . yes
C11 C12 C13 120.4(3) . . . no
C13 C12 C17 119.6(3) . . . no
C11 C12 C17 120.0(3) . . . no
C12 C13 C14 120.0(4) . . . no
C13 C14 C15 120.3(4) . . . no
C14 C15 C16 119.5(3) . . . no
C15 C16 C17 120.4(4) . . . no
C12 C17 C16 120.2(4) . . . no
N1 C1 H1 127(2) . . . no
N2 C1 H1 124(2) . . . no
C3 C2 H2 133(3) . . . no
N1 C2 H2 120(3) . . . no
N2 C3 H3 123(3) . . . no
C2 C3 H3 129(3) . . . no
N1 C4 H4A 110(3) . . . no
N1 C4 H4B 106(2) . . . no
H4A C4 H4B 109(5) . . . no
C5 C4 H4B 109(2) . . . no
C5 C4 H4A 110(4) . . . no
C5 C6 H6 117(3) . . . no
C7 C6 H6 123(3) . . . no
C6 C7 H7 121(3) . . . no
C8 C7 H7 119(3) . . . no
C9 C8 H8 120(3) . . . no
C7 C8 H8 120(3) . . . no
C8 C9 H9 124(3) . . . no
C10 C9 H9 116(3) . . . no
C9 C10 H10 118(3) . . . no
C5 C10 H10 121(3) . . . no
N2 C11 H11B 109(3) . . . no
C12 C11 H11A 111(2) . . . no
N2 C11 H11A 106(2) . . . no
H11A C11 H11B 108(4) . . . no
C12 C11 H11B 112(2) . . . no
C12 C13 H13 120(3) . . . no
C14 C13 H13 120(3) . . . no
C13 C14 H14 119(4) . . . no
C15 C14 H14 121(4) . . . no
C16 C15 H15 121(3) . . . no
C14 C15 H15 119(3) . . . no
C15 C16 H16 117(3) . . . no
C17 C16 H16 123(3) . . . no
C16 C17 H17 120(3) . . . no
C12 C17 H17 120(3) . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 0.8(4) . . . . no
C4 N1 C1 N2 -176.8(3) . . . . no
C1 N1 C4 C5 -122.1(4) . . . . no
C2 N1 C4 C5 60.8(5) . . . . no
C1 N1 C2 C3 0.1(4) . . . . no
C4 N1 C2 C3 177.6(4) . . . . no
C1 N2 C11 C12 -142.4(4) . . . . no
C1 N2 C3 C2 1.5(4) . . . . no
C11 N2 C3 C2 176.9(3) . . . . no
C3 N2 C1 N1 -1.4(4) . . . . no
C11 N2 C1 N1 -176.9(3) . . . . no
C3 N2 C11 C12 42.9(5) . . . . no
N1 C2 C3 N2 -1.0(4) . . . . no
N1 C4 C5 C6 -131.8(4) . . . . no
N1 C4 C5 C10 49.5(5) . . . . no
C4 C5 C6 C7 -176.8(3) . . . . no
C6 C5 C10 C9 -1.2(6) . . . . no
C10 C5 C6 C7 2.0(6) . . . . no
C4 C5 C10 C9 177.6(3) . . . . no
C5 C6 C7 C8 -1.4(6) . . . . no
C6 C7 C8 C9 0.0(6) . . . . no
C7 C8 C9 C10 0.8(6) . . . . no
C8 C9 C10 C5 -0.2(6) . . . . no
N2 C11 C12 C13 85.7(4) . . . . no
N2 C11 C12 C17 -94.2(4) . . . . no
C11 C12 C13 C14 180.0(3) . . . . no
C17 C12 C13 C14 -0.1(5) . . . . no
C11 C12 C17 C16 179.1(3) . . . . no
C13 C12 C17 C16 -0.8(5) . . . . no
C12 C13 C14 C15 1.1(6) . . . . no
C13 C14 C15 C16 -1.2(6) . . . . no
C14 C15 C16 C17 0.3(6) . . . . no
C15 C16 C17 C12 0.7(6) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C1 H1 O4 0.88(4) 2.40(4) 3.066(4) 133(3) . yes
C1 H1 O3 0.88(4) 2.49(4) 3.140(5) 131(3) 2_655 yes
C2 H2 O1 0.85(5) 2.37(5) 3.171(5) 156(4) 2_665 yes
C9 H9 O4 0.91(5) 2.48(5) 3.318(5) 153(4) 2_755 yes
C10 H10 O3 0.93(5) 2.60(5) 3.518(4) 170(4) 1_655 yes
C13 H13 O2 0.97(4) 2.55(5) 3.474(5) 159(4) . yes

#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound10
_database_code_depnum_ccdc_archive 'CCDC 1030640'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_formula_moiety         'C17 H12 F5 N2, O4 Re'
_chemical_formula_sum            'C17 H12 F5 N2 O4 Re'
_chemical_formula_weight         589.50

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'
F F 0.0171 0.0103 ' 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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   8.3467(2)
_cell_length_b                   10.5776(3)
_cell_length_c                   20.3571(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.458(1)
_cell_angle_gamma                90
_cell_volume                     1767.43(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.1776
_cell_measurement_theta_max      25.5193

_exptl_crystal_description       fragment
_exptl_crystal_colour            'clear pale yellow'

_exptl_crystal_size_max          0.980
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.430
_exptl_crystal_density_diffrn    2.215
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    6.955

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'

_exptl_absorpt_correction_T_min  0.056
_exptl_absorpt_correction_T_max  0.152

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed-tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            33118
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.55
_diffrn_reflns_theta_full        25.55
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3295
# number of observed reflections (> n sig(I))
_reflns_number_gt                3186
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0030P)²+2.5644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    refall

_refine_ls_extinction_method     shelxl
_refine_ls_extinction_coef       0.00424(7)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         3295
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0140
_refine_ls_R_factor_gt           0.0131
_refine_ls_wR_factor_ref         0.0293
_refine_ls_wR_factor_gt          0.0290
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.062

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

F1 F Uani 0.81375(17) 0.13382(12) 0.32393(7) 1.000 0.0194(4) d . . .
F2 F Uani 1.07685(18) 0.14137(14) 0.42380(7) 1.000 0.0240(5) d . . .
F3 F Uani 1.18665(17) 0.36688(15) 0.47676(7) 1.000 0.0269(5) d . . .
F4 F Uani 1.03351(18) 0.58371(14) 0.43118(8) 1.000 0.0275(5) d . . .
F5 F Uani 0.76866(17) 0.57612(13) 0.33306(8) 1.000 0.0231(5) d . . .
N1 N Uani 0.7759(2) 0.37516(18) 0.11809(10) 1.000 0.0137(6) d . . .
N2 N Uani 0.6631(2) 0.35969(17) 0.20487(9) 1.000 0.0115(5) d . . .
C1 C Uani 0.8053(3) 0.3709(2) 0.18436(12) 1.000 0.0130(7) d . . .
C2 C Uani 0.6109(3) 0.3672(2) 0.09598(12) 1.000 0.0165(7) d . . .
C3 C Uani 0.5402(3) 0.3575(2) 0.15002(12) 1.000 0.0161(7) d . . .
C4 C Uani 0.8986(3) 0.4006(2) 0.07575(12) 1.000 0.0166(7) d . . .
C5 C Uani 0.9133(3) 0.5405(2) 0.06470(11) 1.000 0.0146(7) d . . .
C6 C Uani 0.8078(3) 0.6018(2) 0.01445(13) 1.000 0.0181(7) d . . .
C7 C Uani 0.8202(3) 0.7319(3) 0.00571(14) 1.000 0.0238(8) d . . .
C8 C Uani 0.9378(4) 0.8003(3) 0.04769(15) 1.000 0.0277(9) d . . .
C9 C Uani 1.0443(3) 0.7390(3) 0.09726(14) 1.000 0.0264(9) d . . .
C10 C Uani 1.0331(3) 0.6093(3) 0.10578(13) 1.000 0.0207(8) d . . .
C11 C Uani 0.6327(3) 0.3484(2) 0.27386(12) 1.000 0.0150(7) d . . .
C12 C Uani 0.7860(3) 0.3547(2) 0.32506(11) 1.000 0.0131(6) d . . .
C13 C Uani 0.8690(3) 0.2458(2) 0.34892(12) 1.000 0.0134(7) d . . .
C14 C Uani 1.0031(3) 0.2485(2) 0.39933(12) 1.000 0.0156(7) d . . .
C15 C Uani 1.0587(3) 0.3630(2) 0.42696(12) 1.000 0.0177(7) d . . .
C16 C Uani 0.9794(3) 0.4730(2) 0.40392(12) 1.000 0.0183(7) d . . .
C17 C Uani 0.8453(3) 0.4682(2) 0.35364(12) 1.000 0.0151(7) d . . .
Re1 Re Uani 0.21632(1) 0.12078(1) 0.20736(1) 1.000 0.0155(1) d . . .
O1 O Uani 0.4213(2) 0.08710(17) 0.22836(9) 1.000 0.0245(6) d . . .
O2 O Uani 0.1912(2) 0.27925(18) 0.18674(10) 1.000 0.0301(6) d . . .
O3 O Uani 0.1224(2) 0.08846(19) 0.27400(10) 1.000 0.0285(6) d . . .
O4 O Uani 0.1308(3) 0.0293(2) 0.14074(10) 1.000 0.0400(7) d . . .
H1 H Uiso 0.907(3) 0.375(2) 0.2101(13) 1.000 0.014(6) d . . .
H2 H Uiso 0.563(3) 0.368(2) 0.0505(14) 1.000 0.015(6) d . . .
H3 H Uiso 0.435(3) 0.350(2) 0.1539(13) 1.000 0.017(7) d . . .
H4A H Uiso 0.996(3) 0.366(2) 0.0982(13) 1.000 0.012(6) d . . .
H4B H Uiso 0.864(3) 0.356(2) 0.0350(14) 1.000 0.016(7) d . . .
H6 H Uiso 0.731(3) 0.554(3) -0.0159(14) 1.000 0.021(7) d . . .
H7 H Uiso 0.753(3) 0.768(3) -0.0279(15) 1.000 0.023(8) d . . .
H8 H Uiso 0.946(4) 0.889(3) 0.0419(15) 1.000 0.031(8) d . . .
H9 H Uiso 1.125(4) 0.786(3) 0.1271(16) 1.000 0.040(9) d . . .
H10 H Uiso 1.109(3) 0.563(2) 0.1388(13) 1.000 0.011(6) d . . .
H11A H Uiso 0.581(3) 0.269(3) 0.2785(13) 1.000 0.018(7) d . . .
H11B H Uiso 0.558(3) 0.417(3) 0.2802(14) 1.000 0.024(7) d . . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O1 1.7238(17) . . yes
Re1 O2 1.7315(19) . . yes
Re1 O3 1.7198(19) . . yes
Re1 O4 1.713(2) . . yes
F1 C13 1.338(3) . . yes
F2 C14 1.342(3) . . yes
F3 C15 1.333(3) . . yes
F4 C16 1.339(3) . . yes
F5 C17 1.338(3) . . yes
N1 C1 1.327(3) . . yes
N1 C2 1.372(3) . . yes
N1 C4 1.478(3) . . yes
N2 C11 1.477(3) . . yes
N2 C3 1.373(3) . . yes
N2 C1 1.333(3) . . yes
C2 C3 1.343(3) . . no
C4 C5 1.505(3) . . no
C5 C10 1.388(4) . . no
C5 C6 1.384(3) . . no
C6 C7 1.394(4) . . no
C7 C8 1.383(4) . . no
C8 C9 1.380(4) . . no
C9 C10 1.388(4) . . no
C11 C12 1.498(3) . . no
C12 C17 1.386(3) . . no
C12 C13 1.386(3) . . no
C13 C14 1.375(3) . . no
C14 C15 1.380(3) . . no
C15 C16 1.378(3) . . no
C16 C17 1.374(3) . . no
C1 H1 0.91(3) . . no
C2 H2 0.94(3) . . no
C3 H3 0.90(3) . . no
C4 H4A 0.93(3) . . no
C4 H4B 0.95(3) . . no
C6 H6 0.95(3) . . no
C7 H7 0.89(3) . . no
C8 H8 0.95(3) . . no
C9 H9 0.96(3) . . no
C10 H10 0.97(3) . . no
C11 H11A 0.96(3) . . no
C11 H11B 0.98(3) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O2 109.34(8) . . . yes
O1 Re1 O3 109.71(9) . . . yes
O1 Re1 O4 109.38(10) . . . yes
O2 Re1 O3 109.34(9) . . . yes
O2 Re1 O4 109.89(10) . . . yes
O3 Re1 O4 109.16(10) . . . yes
C2 N1 C4 125.5(2) . . . yes
C1 N1 C2 108.71(19) . . . yes
C1 N1 C4 125.38(19) . . . yes
C3 N2 C11 122.71(19) . . . yes
C1 N2 C11 128.43(19) . . . yes
C1 N2 C3 108.85(19) . . . yes
N1 C1 N2 108.1(2) . . . yes
N1 C2 C3 107.5(2) . . . yes
N2 C3 C2 106.9(2) . . . yes
N1 C4 C5 110.49(19) . . . yes
C6 C5 C10 119.5(2) . . . no
C4 C5 C6 120.9(2) . . . no
C4 C5 C10 119.7(2) . . . no
C5 C6 C7 120.3(2) . . . no
C6 C7 C8 119.9(3) . . . no
C7 C8 C9 119.8(3) . . . no
C8 C9 C10 120.5(3) . . . no
C5 C10 C9 120.0(2) . . . no
N2 C11 C12 112.7(2) . . . yes
C11 C12 C13 121.1(2) . . . no
C13 C12 C17 117.1(2) . . . no
C11 C12 C17 121.7(2) . . . no
C12 C13 C14 122.1(2) . . . no
F1 C13 C14 118.69(19) . . . yes
F1 C13 C12 119.1(2) . . . yes
C13 C14 C15 119.4(2) . . . no
F2 C14 C13 121.08(19) . . . yes
F2 C14 C15 119.5(2) . . . yes
C14 C15 C16 119.8(2) . . . no
F3 C15 C14 120.1(2) . . . yes
F3 C15 C16 120.1(2) . . . yes
F4 C16 C15 119.5(2) . . . yes
F4 C16 C17 120.6(2) . . . yes
C15 C16 C17 119.9(2) . . . no
F5 C17 C12 119.6(2) . . . yes
C12 C17 C16 121.7(2) . . . no
F5 C17 C16 118.71(19) . . . yes
N1 C1 H1 124.2(16) . . . no
N2 C1 H1 127.7(16) . . . no
C3 C2 H2 129.5(16) . . . no
N1 C2 H2 123.0(16) . . . no
N2 C3 H3 121.8(17) . . . no
C2 C3 H3 131.3(17) . . . no
H4A C4 H4B 109(2) . . . no
N1 C4 H4A 106.1(16) . . . no
N1 C4 H4B 106.6(16) . . . no
C5 C4 H4A 111.8(14) . . . no
C5 C4 H4B 112.1(14) . . . no
C7 C6 H6 119.9(19) . . . no
C5 C6 H6 119.6(19) . . . no
C6 C7 H7 118(2) . . . no
C8 C7 H7 122(2) . . . no
C9 C8 H8 120(2) . . . no
C7 C8 H8 120.0(19) . . . no
C10 C9 H9 119.2(19) . . . no
C8 C9 H9 120.3(19) . . . no
C5 C10 H10 117.5(14) . . . no
C9 C10 H10 122.4(14) . . . no
H11A C11 H11B 109(2) . . . no
N2 C11 H11A 108.9(16) . . . no
N2 C11 H11B 106.8(17) . . . no
C12 C11 H11A 108.3(16) . . . no
C12 C11 H11B 111.0(16) . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 0.4(2) . . . . no
C4 N1 C1 N2 173.24(19) . . . . no
C1 N1 C4 C5 -88.3(3) . . . . no
C2 N1 C4 C5 83.4(3) . . . . no
C1 N1 C2 C3 -0.2(2) . . . . no
C4 N1 C2 C3 -173.11(19) . . . . no
C1 N2 C11 C12 1.9(3) . . . . no
C1 N2 C3 C2 0.2(2) . . . . no
C11 N2 C3 C2 -178.73(19) . . . . no
C3 N2 C1 N1 -0.3(2) . . . . no
C11 N2 C1 N1 178.50(19) . . . . no
C3 N2 C11 C12 -179.42(19) . . . . no
N1 C2 C3 N2 0.0(2) . . . . no
N1 C4 C5 C6 -84.4(3) . . . . no
N1 C4 C5 C10 95.0(3) . . . . no
C4 C5 C6 C7 178.5(2) . . . . no
C6 C5 C10 C9 1.4(4) . . . . no
C10 C5 C6 C7 -0.9(4) . . . . no
C4 C5 C10 C9 -178.0(2) . . . . no
C5 C6 C7 C8 -0.4(4) . . . . no
C6 C7 C8 C9 1.2(4) . . . . no
C7 C8 C9 C10 -0.7(4) . . . . no
C8 C9 C10 C5 -0.6(4) . . . . no
N2 C11 C12 C13 -92.9(3) . . . . no
N2 C11 C12 C17 91.2(3) . . . . no
C11 C12 C13 F1 2.3(3) . . . . no
C11 C12 C13 C14 -175.2(2) . . . . no
C17 C12 C13 F1 178.4(2) . . . . no
C17 C12 C13 C14 0.9(4) . . . . no
C11 C12 C17 F5 -3.2(4) . . . . no
C11 C12 C17 C16 175.4(2) . . . . no
C13 C12 C17 F5 -179.2(2) . . . . no
C13 C12 C17 C16 -0.7(4) . . . . no
F1 C13 C14 F2 -0.7(4) . . . . no
F1 C13 C14 C15 -178.1(2) . . . . no
C12 C13 C14 F2 176.8(2) . . . . no
C12 C13 C14 C15 -0.6(4) . . . . no
F2 C14 C15 F3 1.2(4) . . . . no
F2 C14 C15 C16 -177.3(2) . . . . no
C13 C14 C15 F3 178.7(2) . . . . no
C13 C14 C15 C16 0.1(4) . . . . no
F3 C15 C16 F4 1.1(4) . . . . no
F3 C15 C16 C17 -178.5(2) . . . . no
C14 C15 C16 F4 179.7(2) . . . . no
C14 C15 C16 C17 0.1(4) . . . . no
F4 C16 C17 F5 -0.9(4) . . . . no
F4 C16 C17 C12 -179.4(2) . . . . no
C15 C16 C17 F5 178.7(2) . . . . no
C15 C16 C17 C12 0.2(4) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C3 H3 O2 0.90(3) 2.38(3) 3.243(3) 162(2) . yes
C4 H4A O2 0.93(3) 2.38(3) 3.273(3) 160(2) 1_655 yes
C7 H7 F4 0.89(3) 2.44(3) 3.243(3) 150(3) 4_464 yes
C9 H9 O4 0.96(3) 2.59(3) 3.241(4) 126(2) 1_665 yes
C11 H11A F1 0.96(3) 2.45(3) 2.813(3) 102.0(18) . yes
C11 H11A O1 0.96(3) 2.46(3) 3.319(3) 150(2) . yes
C11 H11B O3 0.98(3) 2.48(3) 3.343(3) 146(2) 2_555 yes


#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound11
_database_code_depnum_ccdc_archive 'CCDC 1030641'
_audit_update_record             
;
2014-10-23 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H7 F10 N2, O4 Re'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H7 F10 N2 O4 Re'
_chemical_formula_iupac          ?
_chemical_formula_weight         679.46
_chemical_compound_source        'see text'

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'
F F 0.0171 0.0103 ' 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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   6.5996(2)
_cell_length_b                   12.4519(3)
_cell_length_c                   23.9499(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1968.14(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9560
_cell_measurement_theta_min      3.0310
_cell_measurement_theta_max      34.0505
_cell_special_details            
;
;

_exptl_crystal_description       prisma
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.293
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    6.297
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.139
_exptl_absorpt_correction_T_max  0.555

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             M. Kaposi
scanspeed                           10 s per frame
dx                                  50 mm
13288 frames measured in 39 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;

_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            66878
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         34.71
_diffrn_reflns_theta_full        34.71
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             8440
# number of observed reflections (> n sig(I))
_reflns_number_gt                7892
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 1997), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0109P)²]         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_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(4)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration ?

_refine_ls_number_reflns         8440
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0358
_refine_ls_wR_factor_gt          0.0351
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.085

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

F1 F Uani 1.1220(2) 0.71751(11) 0.44376(6) 1.000 0.0352(4) d . . .
F2 F Uani 1.0239(3) 0.61652(13) 0.53964(6) 1.000 0.0532(6) d . . .
F3 F Uani 0.6524(4) 0.52472(13) 0.55097(7) 1.000 0.0637(7) d . . .
F4 F Uani 0.3827(2) 0.53311(13) 0.46643(9) 1.000 0.0644(7) d . . .
F5 F Uani 0.47634(19) 0.64304(14) 0.37177(7) 1.000 0.0480(5) d . . .
F6 F Uani 0.7766(2) 0.79296(12) 0.13291(6) 1.000 0.0376(4) d . . .
F7 F Uani 1.0183(2) 0.91397(11) 0.06757(6) 1.000 0.0417(5) d . . .
F8 F Uani 1.3743(2) 0.83260(11) 0.02919(6) 1.000 0.0403(4) d . . .
F9 F Uani 1.4889(2) 0.63085(13) 0.05761(6) 1.000 0.0403(5) d . . .
F10 F Uani 1.2456(2) 0.50905(11) 0.12244(6) 1.000 0.0355(4) d . . .
N1 N Uani 0.9198(2) 0.60095(12) 0.22558(7) 1.000 0.0176(3) d . . .
N2 N Uani 0.9069(2) 0.67049(12) 0.30774(6) 1.000 0.0190(4) d . . .
C1 C Uani 0.8189(3) 0.66881(15) 0.25833(8) 1.000 0.0203(5) d . . .
C2 C Uani 1.0785(3) 0.55810(16) 0.25537(8) 1.000 0.0200(4) d . . .
C3 C Uani 1.0700(3) 0.60132(16) 0.30692(8) 1.000 0.0210(5) d . . .
C4 C Uani 0.8521(4) 0.74349(15) 0.35331(8) 1.000 0.0258(5) d . . .
C5 C Uani 0.8009(3) 0.68277(15) 0.40552(8) 1.000 0.0195(4) d . . .
C6 C Uani 0.9374(3) 0.67326(15) 0.44901(8) 1.000 0.0213(5) d . . .
C7 C Uani 0.8917(4) 0.62048(17) 0.49778(9) 1.000 0.0305(7) d . . .
C8 C Uani 0.7026(4) 0.57412(19) 0.50307(10) 1.000 0.0359(7) d . . .
C9 C Uani 0.5638(4) 0.57949(19) 0.46065(12) 1.000 0.0364(7) d . . .
C10 C Uani 0.6135(3) 0.63459(18) 0.41247(9) 1.000 0.0282(6) d . . .
C11 C Uani 0.8705(3) 0.58059(16) 0.16664(8) 1.000 0.0231(5) d . . .
C12 C Uani 1.0026(3) 0.64645(18) 0.12878(7) 1.000 0.0205(4) d . . .
C13 C Uani 0.9505(3) 0.75102(17) 0.11407(8) 1.000 0.0247(5) d . . .
C14 C Uani 1.0742(4) 0.81382(17) 0.08073(9) 1.000 0.0275(6) d . . .
C15 C Uani 1.2534(3) 0.77236(18) 0.06178(9) 1.000 0.0270(6) d . . .
C16 C Uani 1.3107(3) 0.66974(18) 0.07531(9) 1.000 0.0262(6) d . . .
C17 C Uani 1.1853(3) 0.60866(17) 0.10844(9) 1.000 0.0236(5) d . . .
Re1 Re Uani 0.64385(1) 0.35479(1) 0.27299(1) 1.000 0.0193(1) d . . .
O1 O Uani 0.4409(2) 0.39200(12) 0.23181(8) 1.000 0.0338(4) d . . .
O2 O Uani 0.8603(2) 0.35222(13) 0.23302(8) 1.000 0.0389(5) d . . .
O3 O Uani 0.6744(3) 0.44397(13) 0.32693(7) 1.000 0.0381(5) d . . .
O4 O Uani 0.5939(2) 0.22794(12) 0.29850(7) 1.000 0.0274(4) d . . .
H1 H Uiso 0.70300 0.70920 0.24790 1.000 0.0240 c R . .
H2 H Uiso 1.17540 0.50770 0.24220 1.000 0.0240 c R . .
H3 H Uiso 1.15950 0.58680 0.33700 1.000 0.0250 c R . .
H4A H Uiso 0.73420 0.78750 0.34190 1.000 0.0310 c R . .
H4B H Uiso 0.96680 0.79270 0.36090 1.000 0.0310 c R . .
H11A H Uiso 0.72650 0.59860 0.15980 1.000 0.0280 c R . .
H11B H Uiso 0.88980 0.50340 0.15830 1.000 0.0280 c R . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 O1 1.7267(16) . . yes
Re1 O2 1.7199(15) . . yes
Re1 O3 1.7153(17) . . yes
Re1 O4 1.7254(15) . . yes
F1 C6 1.343(2) . . yes
F2 C7 1.330(3) . . yes
F3 C8 1.343(3) . . yes
F4 C9 1.335(3) . . yes
F5 C10 1.334(3) . . yes
F6 C13 1.339(2) . . yes
F7 C14 1.338(3) . . yes
F8 C15 1.345(3) . . yes
F9 C16 1.341(2) . . yes
F10 C17 1.345(3) . . yes
N1 C11 1.471(3) . . yes
N1 C2 1.375(2) . . yes
N1 C1 1.331(2) . . yes
N2 C3 1.379(2) . . yes
N2 C4 1.466(2) . . yes
N2 C1 1.318(2) . . yes
C2 C3 1.348(3) . . no
C4 C5 1.500(3) . . no
C5 C6 1.382(3) . . no
C5 C10 1.385(3) . . no
C6 C7 1.374(3) . . no
C7 C8 1.381(4) . . no
C8 C9 1.370(4) . . no
C9 C10 1.382(3) . . no
C11 C12 1.502(3) . . no
C12 C17 1.383(3) . . no
C12 C13 1.392(3) . . no
C13 C14 1.384(3) . . no
C14 C15 1.368(3) . . no
C15 C16 1.371(3) . . no
C16 C17 1.376(3) . . no
C1 H1 0.9500 . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4B 0.9900 . . no
C4 H4A 0.9900 . . no
C11 H11A 0.9900 . . no
C11 H11B 0.9900 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Re1 O2 109.35(8) . . . yes
O1 Re1 O3 110.34(8) . . . yes
O1 Re1 O4 107.44(7) . . . yes
O2 Re1 O3 109.49(9) . . . yes
O2 Re1 O4 109.80(7) . . . yes
O3 Re1 O4 110.39(8) . . . yes
C2 N1 C11 126.85(15) . . . yes
C1 N1 C2 108.76(16) . . . yes
C1 N1 C11 124.35(15) . . . yes
C3 N2 C4 126.21(16) . . . yes
C1 N2 C4 124.72(16) . . . yes
C1 N2 C3 108.74(15) . . . yes
N1 C1 N2 108.58(16) . . . yes
N1 C2 C3 106.78(17) . . . yes
N2 C3 C2 107.15(17) . . . yes
N2 C4 C5 111.33(15) . . . yes
C6 C5 C10 117.03(18) . . . no
C4 C5 C6 121.64(19) . . . no
C4 C5 C10 121.33(19) . . . no
C5 C6 C7 122.6(2) . . . no
F1 C6 C5 119.05(17) . . . yes
F1 C6 C7 118.36(19) . . . yes
F2 C7 C6 121.0(2) . . . yes
C6 C7 C8 118.5(2) . . . no
F2 C7 C8 120.6(2) . . . yes
F3 C8 C7 119.5(2) . . . yes
C7 C8 C9 121.1(2) . . . no
F3 C8 C9 119.4(2) . . . yes
C8 C9 C10 119.0(2) . . . no
F4 C9 C10 120.9(2) . . . yes
F4 C9 C8 120.1(2) . . . yes
C5 C10 C9 121.8(2) . . . no
F5 C10 C5 118.94(19) . . . yes
F5 C10 C9 119.2(2) . . . yes
N1 C11 C12 110.92(15) . . . yes
C13 C12 C17 116.39(18) . . . no
C11 C12 C13 121.35(18) . . . no
C11 C12 C17 122.21(19) . . . no
F6 C13 C12 119.42(18) . . . yes
F6 C13 C14 118.66(19) . . . yes
C12 C13 C14 121.93(19) . . . no
C13 C14 C15 119.2(2) . . . no
F7 C14 C15 120.8(2) . . . yes
F7 C14 C13 120.0(2) . . . yes
C14 C15 C16 120.8(2) . . . no
F8 C15 C16 119.55(18) . . . yes
F8 C15 C14 119.67(19) . . . yes
C15 C16 C17 119.04(19) . . . no
F9 C16 C15 120.25(19) . . . yes
F9 C16 C17 120.7(2) . . . yes
C12 C17 C16 122.7(2) . . . no
F10 C17 C12 118.94(18) . . . yes
F10 C17 C16 118.40(18) . . . yes
N1 C1 H1 126.00 . . . no
N2 C1 H1 126.00 . . . no
N1 C2 H2 127.00 . . . no
C3 C2 H2 127.00 . . . no
C2 C3 H3 126.00 . . . no
N2 C3 H3 126.00 . . . no
C5 C4 H4A 109.00 . . . no
N2 C4 H4B 109.00 . . . no
N2 C4 H4A 109.00 . . . no
C5 C4 H4B 109.00 . . . no
H4A C4 H4B 108.00 . . . no
H11A C11 H11B 108.00 . . . no
N1 C11 H11A 109.00 . . . no
N1 C11 H11B 109.00 . . . no
C12 C11 H11A 109.00 . . . no
C12 C11 H11B 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -0.2(2) . . . . no
C11 N1 C1 N2 -177.81(16) . . . . no
C1 N1 C2 C3 0.4(2) . . . . no
C11 N1 C2 C3 177.91(17) . . . . no
C1 N1 C11 C12 97.3(2) . . . . no
C2 N1 C11 C12 -79.9(2) . . . . no
C3 N2 C1 N1 -0.1(2) . . . . no
C4 N2 C1 N1 173.59(16) . . . . no
C1 N2 C3 C2 0.3(2) . . . . no
C4 N2 C3 C2 -173.25(17) . . . . no
C1 N2 C4 C5 124.5(2) . . . . no
C3 N2 C4 C5 -62.9(3) . . . . no
N1 C2 C3 N2 -0.4(2) . . . . no
N2 C4 C5 C6 101.4(2) . . . . no
N2 C4 C5 C10 -79.3(3) . . . . no
C4 C5 C6 F1 -1.5(3) . . . . no
C4 C5 C6 C7 178.22(19) . . . . no
C10 C5 C6 F1 179.11(18) . . . . no
C10 C5 C6 C7 -1.2(3) . . . . no
C4 C5 C10 F5 -0.2(3) . . . . no
C4 C5 C10 C9 -179.3(2) . . . . no
C6 C5 C10 F5 179.15(18) . . . . no
C6 C5 C10 C9 0.1(3) . . . . no
F1 C6 C7 F2 2.4(3) . . . . no
F1 C6 C7 C8 -179.44(19) . . . . no
C5 C6 C7 F2 -177.32(19) . . . . no
C5 C6 C7 C8 0.8(3) . . . . no
F2 C7 C8 F3 0.0(3) . . . . no
F2 C7 C8 C9 178.7(2) . . . . no
C6 C7 C8 F3 -178.1(2) . . . . no
C6 C7 C8 C9 0.6(3) . . . . no
F3 C8 C9 F4 -2.0(4) . . . . no
F3 C8 C9 C10 177.2(2) . . . . no
C7 C8 C9 F4 179.3(2) . . . . no
C7 C8 C9 C10 -1.6(4) . . . . no
F4 C9 C10 F5 1.3(3) . . . . no
F4 C9 C10 C5 -179.7(2) . . . . no
C8 C9 C10 F5 -177.8(2) . . . . no
C8 C9 C10 C5 1.2(4) . . . . no
N1 C11 C12 C13 -86.5(2) . . . . no
N1 C11 C12 C17 91.0(2) . . . . no
C11 C12 C13 F6 -1.7(3) . . . . no
C11 C12 C13 C14 177.80(19) . . . . no
C17 C12 C13 F6 -179.25(18) . . . . no
C17 C12 C13 C14 0.2(3) . . . . no
C11 C12 C17 F10 0.9(3) . . . . no
C11 C12 C17 C16 -177.69(19) . . . . no
C13 C12 C17 F10 178.42(17) . . . . no
C13 C12 C17 C16 -0.1(3) . . . . no
F6 C13 C14 F7 -0.5(3) . . . . no
F6 C13 C14 C15 179.21(19) . . . . no
C12 C13 C14 F7 179.98(19) . . . . no
C12 C13 C14 C15 -0.3(3) . . . . no
F7 C14 C15 F8 -0.5(3) . . . . no
F7 C14 C15 C16 180.0(2) . . . . no
C13 C14 C15 F8 179.75(19) . . . . no
C13 C14 C15 C16 0.2(3) . . . . no
F8 C15 C16 F9 2.1(3) . . . . no
F8 C15 C16 C17 -179.66(19) . . . . no
C14 C15 C16 F9 -178.4(2) . . . . no
C14 C15 C16 C17 -0.1(3) . . . . no
F9 C16 C17 F10 -0.2(3) . . . . no
F9 C16 C17 C12 178.36(19) . . . . no
C15 C16 C17 F10 -178.48(19) . . . . no
C15 C16 C17 C12 0.1(3) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C1 H1 O1 0.9500 2.5100 3.274(2) 137.00 4_655 yes
C1 H1 O4 0.9500 2.2600 3.133(2) 152.00 4_655 yes
C2 H2 O1 0.9500 2.2800 3.212(2) 166.00 1_655 yes
C3 H3 F5 0.9500 2.3600 3.142(2) 140.00 1_655 yes
C4 H4A O1 0.9900 2.4800 3.364(3) 149.00 4_655 yes
C4 H4B F1 0.9900 2.4200 2.823(3) 104.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
