# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1003925'
_audit_update_record             
;
2014-05-19 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N4 O, 2(N O3), 2(H2 O)'
_chemical_formula_sum            'C12 H14 N6 O9'
_chemical_formula_weight         386.29

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.4845(15)
_cell_length_b                   18.648(4)
_cell_length_c                   11.768(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.46(3)
_cell_angle_gamma                90.00
_cell_volume                     1642.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16990
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle-shaped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16990
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3759
_reflns_number_gt                2199
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0757P)²+0.2713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1657
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8730(3) 0.73305(14) 0.9424(2) 0.0361(6) Uani 1 1 d . . .
H1 H 0.8148 0.7240 1.0104 0.043 Uiso 1 1 calc R . .
C2 C 0.9397(4) 0.67782(15) 0.8788(2) 0.0418(7) Uani 1 1 d . . .
H2 H 0.9259 0.6307 0.9030 0.050 Uiso 1 1 calc R . .
N1 N 1.0244(3) 0.69180(13) 0.7822(2) 0.0451(6) Uani 1 1 d . . .
H3 H 1.0645 0.6565 0.7430 0.054 Uiso 1 1 calc R . .
C3 C 1.0495(4) 0.75829(18) 0.7439(2) 0.0474(8) Uani 1 1 d . . .
H4 H 1.1113 0.7656 0.6767 0.057 Uiso 1 1 calc R . .
C4 C 0.9851(4) 0.81604(15) 0.8029(2) 0.0406(7) Uani 1 1 d . . .
H5 H 1.0019 0.8625 0.7765 0.049 Uiso 1 1 calc R . .
C5 C 0.8939(3) 0.80308(13) 0.9033(2) 0.0319(6) Uani 1 1 d . . .
C6 C 0.8204(3) 0.86428(14) 0.9639(2) 0.0312(6) Uani 1 1 d . . .
N2 N 0.8201(3) 0.93048(12) 0.93222(19) 0.0401(6) Uani 1 1 d . . .
N3 N 0.7302(3) 0.96841(12) 1.01648(19) 0.0395(6) Uani 1 1 d . . .
C7 C 0.6827(3) 0.92184(13) 1.0909(2) 0.0297(6) Uani 1 1 d . . .
O1 O 0.7357(2) 0.85415(9) 1.06457(14) 0.0319(4) Uani 1 1 d . . .
C8 C 0.5785(3) 0.93443(13) 1.1935(2) 0.0304(6) Uani 1 1 d . . .
C9 C 0.5292(3) 0.87839(14) 1.2645(2) 0.0351(6) Uani 1 1 d . . .
H6 H 0.5637 0.8316 1.2487 0.042 Uiso 1 1 calc R . .
C10 C 0.4287(4) 0.89360(15) 1.3583(2) 0.0390(7) Uani 1 1 d . . .
H7 H 0.3947 0.8569 1.4071 0.047 Uiso 1 1 calc R . .
N4 N 0.3798(3) 0.96072(12) 1.37938(19) 0.0385(6) Uani 1 1 d . . .
H8 H 0.3154 0.9691 1.4381 0.046 Uiso 1 1 calc R . .
C11 C 0.4263(4) 1.01550(15) 1.3136(2) 0.0399(7) Uani 1 1 d . . .
H9 H 0.3891 1.0617 1.3317 0.048 Uiso 1 1 calc R . .
C12 C 0.5286(3) 1.00425(14) 1.2195(2) 0.0359(6) Uani 1 1 d . . .
H10 H 0.5638 1.0424 1.1739 0.043 Uiso 1 1 calc R . .
N5 N 0.1265(3) 0.96881(14) 0.6118(2) 0.0436(6) Uani 1 1 d . . .
O2 O 0.1960(3) 1.01821(11) 0.55469(17) 0.0489(5) Uani 1 1 d . . .
O3 O 0.1604(3) 0.90548(12) 0.5860(2) 0.0660(7) Uani 1 1 d . . .
O4 O 0.0276(3) 0.98384(14) 0.69085(19) 0.0746(8) Uani 1 1 d . . .
N6 N 0.3711(3) 0.69773(13) 0.4565(2) 0.0415(6) Uani 1 1 d . . .
O5 O 0.4675(3) 0.72366(13) 0.3814(2) 0.0698(7) Uani 1 1 d . . .
O6 O 0.3463(3) 0.63249(11) 0.4600(2) 0.0658(7) Uani 1 1 d . . .
O7 O 0.3034(3) 0.73791(14) 0.5270(2) 0.0799(8) Uani 1 1 d . . .
O8 O 0.1205(3) 0.91322(10) 0.14107(17) 0.0501(5) Uani 1 1 d . . .
H11 H 0.0998 0.9535 0.1721 0.075 Uiso 1 1 d R . .
H12 H 0.0600 0.9098 0.0798 0.075 Uiso 1 1 d R . .
O9 O 0.5824(3) 0.81075(13) 0.6577(2) 0.0730(7) Uani 1 1 d . . .
H13 H 0.5593 0.8068 0.7202 0.109 Uiso 1 1 d R . .
H14 H 0.4918 0.8135 0.6139 0.109 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.369(4) . ?
C1 C5 1.394(4) . ?
C1 H1 0.9300 . ?
C2 N1 1.332(4) . ?
C2 H2 0.9300 . ?
N1 C3 1.333(4) . ?
N1 H3 0.8600 . ?
C3 C4 1.371(4) . ?
C3 H4 0.9300 . ?
C4 C5 1.391(3) . ?
C4 H5 0.9300 . ?
C5 C6 1.456(3) . ?
C6 N2 1.290(3) . ?
C6 O1 1.361(3) . ?
N2 N3 1.395(3) . ?
N3 C7 1.285(3) . ?
C7 O1 1.360(3) . ?
C7 C8 1.462(3) . ?
C8 C12 1.389(4) . ?
C8 C9 1.389(3) . ?
C9 C10 1.371(4) . ?
C9 H6 0.9300 . ?
C10 N4 1.328(3) . ?
C10 H7 0.9300 . ?
N4 C11 1.330(3) . ?
N4 H8 0.8600 . ?
C11 C12 1.368(4) . ?
C11 H9 0.9300 . ?
C12 H10 0.9300 . ?
N5 O4 1.226(3) . ?
N5 O3 1.246(3) . ?
N5 O2 1.255(3) . ?
N6 O7 1.230(3) . ?
N6 O6 1.232(3) . ?
N6 O5 1.243(3) . ?
O8 H11 0.8500 . ?
O8 H12 0.8500 . ?
O9 H13 0.7604 . ?
O9 H14 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 118.8(2) . . ?
C2 C1 H1 120.6 . . ?
C5 C1 H1 120.6 . . ?
N1 C2 C1 119.8(3) . . ?
N1 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 N1 C3 122.7(2) . . ?
C2 N1 H3 118.7 . . ?
C3 N1 H3 118.7 . . ?
N1 C3 C4 120.6(3) . . ?
N1 C3 H4 119.7 . . ?
C4 C3 H4 119.7 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 H5 121.0 . . ?
C5 C4 H5 121.0 . . ?
C4 C5 C1 120.0(2) . . ?
C4 C5 C6 118.0(2) . . ?
C1 C5 C6 122.0(2) . . ?
N2 C6 O1 112.6(2) . . ?
N2 C6 C5 127.5(2) . . ?
O1 C6 C5 119.9(2) . . ?
C6 N2 N3 106.2(2) . . ?
C7 N3 N2 106.2(2) . . ?
N3 C7 O1 112.9(2) . . ?
N3 C7 C8 127.3(2) . . ?
O1 C7 C8 119.7(2) . . ?
C7 O1 C6 102.01(18) . . ?
C12 C8 C9 120.0(2) . . ?
C12 C8 C7 118.6(2) . . ?
C9 C8 C7 121.4(2) . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 H6 120.7 . . ?
C8 C9 H6 120.7 . . ?
N4 C10 C9 120.0(2) . . ?
N4 C10 H7 120.0 . . ?
C9 C10 H7 120.0 . . ?
C10 N4 C11 122.8(2) . . ?
C10 N4 H8 118.6 . . ?
C11 N4 H8 118.6 . . ?
N4 C11 C12 120.3(2) . . ?
N4 C11 H9 119.9 . . ?
C12 C11 H9 119.9 . . ?
C11 C12 C8 118.4(2) . . ?
C11 C12 H10 120.8 . . ?
C8 C12 H10 120.8 . . ?
O4 N5 O3 121.8(3) . . ?
O4 N5 O2 119.6(3) . . ?
O3 N5 O2 118.6(2) . . ?
O7 N6 O6 121.1(3) . . ?
O7 N6 O5 119.1(3) . . ?
O6 N6 O5 119.7(2) . . ?
H11 O8 H12 109.5 . . ?
H13 O9 H14 113.9 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.078
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1003926'
_audit_update_record             
;
2014-05-19 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N4 O, H P O4'
_chemical_formula_sum            'C12 H11 N4 O5 P'
_chemical_formula_weight         322.22

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   14.716(3)
_cell_length_b                   17.249(3)
_cell_length_c                   10.967(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.24(3)
_cell_angle_gamma                90.00
_cell_volume                     2776.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14250
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14250
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3184
_reflns_number_gt                1801
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0792P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3180
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1673
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1686(2) 0.45381(16) 0.8412(3) 0.0395(7) Uani 1 1 d . . .
H1 H 0.1913 0.4920 0.8950 0.047 Uiso 1 1 calc R . .
C2 C 0.1803(2) 0.37621(17) 0.8696(3) 0.0441(8) Uani 1 1 d . . .
H2 H 0.2117 0.3630 0.9434 0.053 Uiso 1 1 calc R . .
N1 N 0.14895(17) 0.32011(14) 0.7966(2) 0.0441(7) Uani 1 1 d . . .
H3 H 0.1573 0.2723 0.8169 0.053 Uiso 1 1 calc R . .
C3 C 0.1037(2) 0.33890(18) 0.6900(3) 0.0470(8) Uani 1 1 d . . .
H4 H 0.0811 0.2992 0.6390 0.056 Uiso 1 1 calc R . .
C4 C 0.0894(2) 0.41353(17) 0.6533(3) 0.0407(7) Uani 1 1 d . . .
H5 H 0.0584 0.4246 0.5783 0.049 Uiso 1 1 calc R . .
C5 C 0.12240(18) 0.47341(16) 0.7311(3) 0.0346(7) Uani 1 1 d . . .
C6 C 0.10480(18) 0.55349(16) 0.6946(2) 0.0336(7) Uani 1 1 d . . .
N2 N 0.05795(17) 0.57748(14) 0.5982(2) 0.0416(6) Uani 1 1 d . . .
N3 N 0.05777(17) 0.65838(14) 0.6042(2) 0.0434(7) Uani 1 1 d . . .
C7 C 0.10410(19) 0.67683(15) 0.7041(3) 0.0338(7) Uani 1 1 d . . .
O1 O 0.13588(12) 0.61305(11) 0.76833(16) 0.0371(5) Uani 1 1 d . . .
C8 C 0.11947(18) 0.75398(16) 0.7536(2) 0.0347(7) Uani 1 1 d . . .
C9 C 0.1482(2) 0.76710(18) 0.8749(3) 0.0453(8) Uani 1 1 d . . .
H6 H 0.1610 0.7258 0.9280 0.054 Uiso 1 1 calc R . .
C10 C 0.1576(2) 0.84263(19) 0.9157(3) 0.0505(8) Uani 1 1 d . . .
H7 H 0.1754 0.8515 0.9976 0.061 Uiso 1 1 calc R . .
N4 N 0.14194(18) 0.90311(14) 0.8420(3) 0.0501(7) Uani 1 1 d . . .
H8 H 0.1498 0.9496 0.8691 0.060 Uiso 1 1 calc R . .
C11 C 0.1139(2) 0.89024(18) 0.7256(3) 0.0475(8) Uani 1 1 d . . .
H9 H 0.1023 0.9327 0.6746 0.057 Uiso 1 1 calc R . .
C12 C 0.1014(2) 0.81722(16) 0.6771(3) 0.0411(8) Uani 1 1 d . . .
H10 H 0.0813 0.8103 0.5954 0.049 Uiso 1 1 calc R . .
P1 P 0.12932(6) 0.11171(5) 0.83938(7) 0.0413(3) Uani 1 1 d . . .
O2 O 0.04215(16) 0.12420(17) 0.9012(2) 0.0801(9) Uani 1 1 d . . .
H11 H -0.0015 0.1125 0.8541 0.120 Uiso 1 1 calc R . .
O3 O 0.19203(15) 0.18171(12) 0.8696(2) 0.0591(7) Uani 1 1 d . . .
O4 O 0.18508(18) 0.04522(13) 0.9028(2) 0.0706(8) Uani 1 1 d . . .
O5 O 0.11141(15) 0.09652(15) 0.70571(19) 0.0610(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(4) . ?
C1 C5 1.384(4) . ?
C1 H1 0.9300 . ?
C2 N1 1.318(4) . ?
C2 H2 0.9300 . ?
N1 C3 1.342(4) . ?
N1 H3 0.8600 . ?
C3 C4 1.360(4) . ?
C3 H4 0.9300 . ?
C4 C5 1.404(4) . ?
C4 H5 0.9300 . ?
C5 C6 1.456(4) . ?
C6 N2 1.287(3) . ?
C6 O1 1.365(3) . ?
N2 N3 1.397(3) . ?
N3 C7 1.287(3) . ?
C7 O1 1.370(3) . ?
C7 C8 1.449(4) . ?
C8 C9 1.384(4) . ?
C8 C12 1.390(4) . ?
C9 C10 1.381(4) . ?
C9 H6 0.9300 . ?
C10 N4 1.329(4) . ?
C10 H7 0.9300 . ?
N4 C11 1.331(4) . ?
N4 H8 0.8600 . ?
C11 C12 1.374(4) . ?
C11 H9 0.9300 . ?
C12 H10 0.9300 . ?
P1 O5 1.493(2) . ?
P1 O2 1.510(3) . ?
P1 O3 1.541(2) . ?
P1 O4 1.545(2) . ?
O2 H11 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 118.6(3) . . ?
C2 C1 H1 120.7 . . ?
C5 C1 H1 120.7 . . ?
N1 C2 C1 122.8(3) . . ?
N1 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 N1 C3 118.8(3) . . ?
C2 N1 H3 120.6 . . ?
C3 N1 H3 120.6 . . ?
N1 C3 C4 122.9(3) . . ?
N1 C3 H4 118.6 . . ?
C4 C3 H4 118.6 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 H5 120.7 . . ?
C5 C4 H5 120.7 . . ?
C1 C5 C4 118.5(3) . . ?
C1 C5 C6 122.6(3) . . ?
C4 C5 C6 119.0(3) . . ?
N2 C6 O1 112.4(2) . . ?
N2 C6 C5 127.2(3) . . ?
O1 C6 C5 120.4(2) . . ?
C6 N2 N3 106.6(2) . . ?
C7 N3 N2 106.5(2) . . ?
N3 C7 O1 112.2(2) . . ?
N3 C7 C8 127.2(3) . . ?
O1 C7 C8 120.5(2) . . ?
C6 O1 C7 102.3(2) . . ?
C9 C8 C12 118.9(3) . . ?
C9 C8 C7 122.6(3) . . ?
C12 C8 C7 118.5(3) . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H6 120.6 . . ?
C8 C9 H6 120.6 . . ?
N4 C10 C9 122.4(3) . . ?
N4 C10 H7 118.8 . . ?
C9 C10 H7 118.8 . . ?
C10 N4 C11 118.7(3) . . ?
C10 N4 H8 120.7 . . ?
C11 N4 H8 120.7 . . ?
N4 C11 C12 123.2(3) . . ?
N4 C11 H9 118.4 . . ?
C12 C11 H9 118.4 . . ?
C11 C12 C8 118.1(3) . . ?
C11 C12 H10 121.0 . . ?
C8 C12 H10 121.0 . . ?
O5 P1 O2 111.84(13) . . ?
O5 P1 O3 114.08(15) . . ?
O2 P1 O3 107.86(15) . . ?
O5 P1 O4 111.15(14) . . ?
O2 P1 O4 110.12(16) . . ?
O3 P1 O4 101.25(12) . . ?
P1 O2 H11 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1003927'
_audit_update_record             
;
2014-05-19 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C12 H10 N4 O), C12 H9 N4 O, 3(I3), 2(I), 2(H2 O)'
_chemical_formula_sum            'C36 H33 I11 N12 O5'
_chemical_formula_weight         2109.64

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'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.637(2)
_cell_length_b                   13.967(3)
_cell_length_c                   21.237(4)
_cell_angle_alpha                82.92(3)
_cell_angle_beta                 76.08(3)
_cell_angle_gamma                69.64(3)
_cell_volume                     2868.4(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    29862
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       lamellar
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1912
_exptl_absorpt_coefficient_mu    5.987
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.224
_exptl_absorpt_correction_T_max  0.321
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29862
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0764
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             13137
_reflns_number_gt                7606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0250P)²+3.9341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13137
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8851(8) -0.0998(6) 0.4530(4) 0.046(2) Uani 1 1 d . . .
H1 H 0.8903 -0.0343 0.4503 0.056 Uiso 1 1 calc R . .
C2 C 0.9893(8) -0.1771(7) 0.4189(4) 0.053(2) Uani 1 1 d . . .
H2 H 1.0653 -0.1640 0.3923 0.064 Uiso 1 1 calc R . .
N1 N 0.9809(7) -0.2702(5) 0.4241(3) 0.0508(18) Uani 1 1 d . . .
H3 H 1.0476 -0.3181 0.4032 0.061 Uiso 1 1 calc R . .
C3 C 0.8739(8) -0.2924(6) 0.4603(4) 0.048(2) Uani 1 1 d . . .
H4 H 0.8719 -0.3588 0.4624 0.058 Uiso 1 1 calc R . .
C4 C 0.7666(8) -0.2188(6) 0.4944(4) 0.046(2) Uani 1 1 d . . .
H5 H 0.6905 -0.2339 0.5193 0.055 Uiso 1 1 calc R . .
C5 C 0.7732(7) -0.1213(5) 0.4912(3) 0.0345(17) Uani 1 1 d . . .
C6 C 0.6609(8) -0.0446(6) 0.5304(3) 0.0366(18) Uani 1 1 d . . .
N2 N 0.5527(6) -0.0579(5) 0.5693(3) 0.0441(16) Uani 1 1 d . . .
N3 N 0.4762(6) 0.0352(5) 0.5983(3) 0.0461(17) Uani 1 1 d . . .
C7 C 0.5448(7) 0.0966(6) 0.5753(3) 0.0367(18) Uani 1 1 d . . .
O1 O 0.6608(5) 0.0531(4) 0.5309(2) 0.0371(12) Uani 1 1 d . . .
C8 C 0.5085(7) 0.2019(5) 0.5932(3) 0.0371(18) Uani 1 1 d . . .
C9 C 0.3995(8) 0.2362(6) 0.6456(4) 0.049(2) Uani 1 1 d . . .
H6 H 0.3511 0.1934 0.6672 0.059 Uiso 1 1 calc R . .
C10 C 0.3642(9) 0.3341(7) 0.6650(4) 0.065(3) Uani 1 1 d . . .
H7 H 0.2927 0.3580 0.7004 0.078 Uiso 1 1 calc R . .
N4 N 0.4330(8) 0.3940(5) 0.6329(4) 0.062(2) Uani 1 1 d . . .
H8 H 0.4094 0.4553 0.6452 0.075 Uiso 1 1 calc R . .
C11 C 0.5358(10) 0.3642(7) 0.5830(5) 0.064(3) Uani 1 1 d . . .
H9 H 0.5813 0.4091 0.5620 0.077 Uiso 1 1 calc R . .
C12 C 0.5762(8) 0.2669(6) 0.5618(4) 0.049(2) Uani 1 1 d . . .
H10 H 0.6488 0.2456 0.5264 0.059 Uiso 1 1 calc R . .
C13 C 1.1485(8) 0.7197(6) 0.0852(4) 0.048(2) Uani 1 1 d . . .
H11 H 1.1456 0.7873 0.0774 0.058 Uiso 1 1 calc R . .
C14 C 1.2226(8) 0.6475(6) 0.0395(4) 0.050(2) Uani 1 1 d . . .
H12 H 1.2731 0.6671 0.0011 0.060 Uiso 1 1 calc R . .
N5 N 1.2249(7) 0.5523(5) 0.0479(3) 0.0489(17) Uani 1 1 d . . .
C15 C 1.1557(9) 0.5216(6) 0.1040(4) 0.058(2) Uani 1 1 d . . .
H13 H 1.1593 0.4537 0.1098 0.070 Uiso 1 1 calc R . .
C16 C 1.0804(8) 0.5872(6) 0.1526(4) 0.045(2) Uani 1 1 d . . .
H14 H 1.0321 0.5652 0.1908 0.054 Uiso 1 1 calc R . .
C17 C 1.0787(7) 0.6880(6) 0.1430(3) 0.0348(17) Uani 1 1 d . . .
C18 C 1.0027(7) 0.7577(6) 0.1965(4) 0.0370(18) Uani 1 1 d . . .
N6 N 0.9500(6) 0.7361(4) 0.2537(3) 0.0404(15) Uani 1 1 d . . .
N7 N 0.8900(6) 0.8283(5) 0.2856(3) 0.0393(15) Uani 1 1 d . . .
C19 C 0.9088(7) 0.8974(6) 0.2439(3) 0.0336(17) Uani 1 1 d . . .
O2 O 0.9769(5) 0.8609(4) 0.1834(2) 0.0382(12) Uani 1 1 d . . .
C20 C 0.8600(7) 1.0075(6) 0.2510(4) 0.0374(18) Uani 1 1 d . . .
C21 C 0.7775(7) 1.0433(6) 0.3098(4) 0.0437(19) Uani 1 1 d . . .
H15 H 0.7513 0.9986 0.3423 0.052 Uiso 1 1 calc R . .
C22 C 0.7349(8) 1.1454(7) 0.3194(4) 0.056(2) Uani 1 1 d . . .
H16 H 0.6818 1.1706 0.3593 0.068 Uiso 1 1 calc R . .
N8 N 0.7694(7) 1.2096(5) 0.2713(4) 0.0560(19) Uani 1 1 d . . .
H17 H 0.7386 1.2743 0.2771 0.067 Uiso 1 1 calc R . .
C23 C 0.8489(10) 1.1754(7) 0.2159(4) 0.066(3) Uani 1 1 d . . .
H18 H 0.8742 1.2216 0.1844 0.079 Uiso 1 1 calc R . .
C24 C 0.8963(8) 1.0740(6) 0.2026(4) 0.049(2) Uani 1 1 d . . .
H19 H 0.9508 1.0509 0.1625 0.059 Uiso 1 1 calc R . .
C25 C 0.5521(9) 0.7714(6) 0.0600(4) 0.057(2) Uani 1 1 d . . .
H20 H 0.4858 0.8335 0.0530 0.068 Uiso 1 1 calc R . .
C26 C 0.5784(9) 0.6918(7) 0.0222(4) 0.060(2) Uani 1 1 d . . .
H21 H 0.5331 0.7003 -0.0116 0.072 Uiso 1 1 calc R . .
N9 N 0.6708(7) 0.6005(5) 0.0340(3) 0.0510(18) Uani 1 1 d . . .
H22 H 0.6860 0.5499 0.0107 0.061 Uiso 1 1 calc R . .
C27 C 0.7378(8) 0.5877(7) 0.0806(4) 0.057(2) Uani 1 1 d . . .
H23 H 0.8011 0.5239 0.0872 0.068 Uiso 1 1 calc R . .
C28 C 0.7182(8) 0.6648(6) 0.1197(4) 0.048(2) Uani 1 1 d . . .
H24 H 0.7662 0.6544 0.1526 0.058 Uiso 1 1 calc R . .
C29 C 0.6213(7) 0.7612(6) 0.1078(3) 0.0374(18) Uani 1 1 d . . .
C30 C 0.6018(8) 0.8430(6) 0.1499(3) 0.0399(18) Uani 1 1 d . . .
N10 N 0.6690(7) 0.8378(5) 0.1944(3) 0.0467(17) Uani 1 1 d . . .
N11 N 0.6112(6) 0.9316(5) 0.2234(3) 0.0460(17) Uani 1 1 d . . .
C31 C 0.5117(8) 0.9844(6) 0.1943(3) 0.043(2) Uani 1 1 d . . .
O3 O 0.4998(5) 0.9329(4) 0.1474(2) 0.0366(12) Uani 1 1 d . . .
C32 C 0.4159(8) 1.0863(6) 0.2103(3) 0.0387(18) Uani 1 1 d . . .
C33 C 0.4332(9) 1.1314(7) 0.2608(4) 0.061(2) Uani 1 1 d . . .
H25 H 0.5042 1.0977 0.2823 0.073 Uiso 1 1 calc R . .
C34 C 0.3431(11) 1.2273(7) 0.2786(4) 0.064(3) Uani 1 1 d . . .
H26 H 0.3556 1.2608 0.3106 0.077 Uiso 1 1 calc R . .
N12 N 0.2418(8) 1.2694(6) 0.2504(4) 0.065(2) Uani 1 1 d . . .
H27 H 0.1833 1.3267 0.2645 0.078 Uiso 1 1 calc R . .
C35 C 0.2198(10) 1.2310(7) 0.2004(4) 0.066(3) Uani 1 1 d . . .
H28 H 0.1465 1.2662 0.1807 0.079 Uiso 1 1 calc R . .
C36 C 0.3097(9) 1.1383(7) 0.1801(4) 0.057(2) Uani 1 1 d . . .
H29 H 0.2989 1.1098 0.1452 0.068 Uiso 1 1 calc R . .
I1 I 0.69939(6) 0.21992(5) 0.74374(3) 0.06214(18) Uani 1 1 d . . .
I2 I 0.58271(5) 0.42708(5) 0.80014(3) 0.05272(15) Uani 1 1 d . . .
I3 I 0.47175(7) 0.62513(5) 0.85605(3) 0.06886(19) Uani 1 1 d . . .
I4 I 0.18047(7) 0.56383(5) 0.54196(3) 0.06754(19) Uani 1 1 d . . .
I5 I 0.03507(6) 0.76212(4) 0.59750(3) 0.05260(16) Uani 1 1 d . . .
I6 I -0.12850(6) 0.96315(5) 0.65277(3) 0.05811(17) Uani 1 1 d . . .
I7 I 0.95166(7) 0.72053(5) -0.05691(3) 0.0730(2) Uani 1 1 d . . .
I8 I 0.82967(6) 0.92109(5) 0.00186(3) 0.05821(16) Uani 1 1 d . . .
I9 I 0.70383(7) 1.11500(5) 0.06542(3) 0.06723(19) Uani 1 1 d . . .
I10 I 0.83184(6) 0.43841(4) 0.23927(3) 0.05483(16) Uani 1 1 d . . .
I11 I 0.53929(6) 0.62553(4) 0.60253(3) 0.05657(17) Uani 1 1 d . . .
O4 O -0.0921(7) 0.5475(6) 0.7002(4) 0.113(3) Uani 1 1 d . . .
O5 O -0.1802(6) 0.4256(5) 0.6402(3) 0.0767(19) Uani 1 1 d . . .
H1O4 H -0.1206 0.5194 0.6740 0.115 Uiso 1 1 d R . .
H2O4 H -0.0035 0.5188 0.6909 0.115 Uiso 1 1 d R . .
H1O5 H -0.2237 0.4090 0.6766 0.115 Uiso 1 1 d R . .
H2O5 H -0.2388 0.4665 0.6199 0.115 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.374(10) . ?
C1 C2 1.376(10) . ?
C1 H1 0.9300 . ?
C2 N1 1.323(9) . ?
C2 H2 0.9300 . ?
N1 C3 1.321(9) . ?
N1 H3 0.8600 . ?
C3 C4 1.361(10) . ?
C3 H4 0.9300 . ?
C4 C5 1.380(10) . ?
C4 H5 0.9300 . ?
C5 C6 1.456(10) . ?
C6 N2 1.301(8) . ?
C6 O1 1.366(8) . ?
N2 N3 1.397(8) . ?
N3 C7 1.292(9) . ?
C7 O1 1.356(8) . ?
C7 C8 1.458(9) . ?
C8 C12 1.364(10) . ?
C8 C9 1.393(9) . ?
C9 C10 1.375(10) . ?
C9 H6 0.9300 . ?
C10 N4 1.321(10) . ?
C10 H7 0.9300 . ?
N4 C11 1.313(10) . ?
N4 H8 0.8600 . ?
C11 C12 1.374(11) . ?
C11 H9 0.9300 . ?
C12 H10 0.9300 . ?
C13 C14 1.378(10) . ?
C13 C17 1.383(9) . ?
C13 H11 0.9300 . ?
C14 N5 1.313(9) . ?
C14 H12 0.9300 . ?
N5 C15 1.348(10) . ?
C15 C16 1.369(10) . ?
C15 H13 0.9300 . ?
C16 C17 1.391(9) . ?
C16 H14 0.9300 . ?
C17 C18 1.475(9) . ?
C18 N6 1.258(8) . ?
C18 O2 1.375(8) . ?
N6 N7 1.400(8) . ?
N7 C19 1.263(8) . ?
C19 O2 1.375(8) . ?
C19 C20 1.456(10) . ?
C20 C24 1.375(10) . ?
C20 C21 1.379(9) . ?
C21 C22 1.363(10) . ?
C21 H15 0.9300 . ?
C22 N8 1.344(10) . ?
C22 H16 0.9300 . ?
N8 C23 1.307(10) . ?
N8 H17 0.8600 . ?
C23 C24 1.370(11) . ?
C23 H18 0.9300 . ?
C24 H19 0.9300 . ?
C25 C29 1.358(10) . ?
C25 C26 1.362(10) . ?
C25 H20 0.9300 . ?
C26 N9 1.351(10) . ?
C26 H21 0.9300 . ?
N9 C27 1.314(10) . ?
N9 H22 0.8600 . ?
C27 C28 1.368(10) . ?
C27 H23 0.9300 . ?
C28 C29 1.420(10) . ?
C28 H24 0.9300 . ?
C29 C30 1.464(9) . ?
C30 N10 1.297(8) . ?
C30 O3 1.348(8) . ?
N10 N11 1.388(8) . ?
N11 C31 1.305(9) . ?
C31 O3 1.351(8) . ?
C31 C32 1.457(10) . ?
C32 C36 1.371(10) . ?
C32 C33 1.385(10) . ?
C33 C34 1.384(11) . ?
C33 H25 0.9300 . ?
C34 N12 1.285(11) . ?
C34 H26 0.9300 . ?
N12 C35 1.348(10) . ?
N12 H27 0.8600 . ?
C35 C36 1.362(11) . ?
C35 H28 0.9300 . ?
C36 H29 0.9300 . ?
I1 I2 2.9978(13) . ?
I2 I3 2.8842(13) . ?
I4 I5 2.8984(14) . ?
I5 I6 2.9529(14) . ?
I7 I8 2.9396(14) . ?
I8 I9 2.9083(14) . ?
O4 H1O4 0.8796 . ?
O4 H2O4 0.8682 . ?
O5 H1O5 0.8499 . ?
O5 H2O5 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 118.7(7) . . ?
C5 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
N1 C2 C1 119.7(8) . . ?
N1 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C3 N1 C2 122.5(7) . . ?
C3 N1 H3 118.7 . . ?
C2 N1 H3 118.7 . . ?
N1 C3 C4 120.5(8) . . ?
N1 C3 H4 119.7 . . ?
C4 C3 H4 119.7 . . ?
C3 C4 C5 118.6(8) . . ?
C3 C4 H5 120.7 . . ?
C5 C4 H5 120.7 . . ?
C1 C5 C4 119.9(7) . . ?
C1 C5 C6 122.1(7) . . ?
C4 C5 C6 118.0(7) . . ?
N2 C6 O1 111.6(6) . . ?
N2 C6 C5 126.8(7) . . ?
O1 C6 C5 121.6(6) . . ?
C6 N2 N3 106.7(6) . . ?
C7 N3 N2 106.0(6) . . ?
N3 C7 O1 112.9(6) . . ?
N3 C7 C8 126.3(7) . . ?
O1 C7 C8 120.8(6) . . ?
C7 O1 C6 102.8(5) . . ?
C12 C8 C9 119.1(7) . . ?
C12 C8 C7 123.5(7) . . ?
C9 C8 C7 117.3(7) . . ?
C10 C9 C8 119.1(8) . . ?
C10 C9 H6 120.4 . . ?
C8 C9 H6 120.4 . . ?
N4 C10 C9 119.3(8) . . ?
N4 C10 H7 120.3 . . ?
C9 C10 H7 120.3 . . ?
C11 N4 C10 123.1(8) . . ?
C11 N4 H8 118.4 . . ?
C10 N4 H8 118.4 . . ?
N4 C11 C12 120.1(9) . . ?
N4 C11 H9 119.9 . . ?
C12 C11 H9 119.9 . . ?
C8 C12 C11 119.2(8) . . ?
C8 C12 H10 120.4 . . ?
C11 C12 H10 120.4 . . ?
C14 C13 C17 117.7(7) . . ?
C14 C13 H11 121.2 . . ?
C17 C13 H11 121.2 . . ?
N5 C14 C13 122.8(8) . . ?
N5 C14 H12 118.6 . . ?
C13 C14 H12 118.6 . . ?
C14 N5 C15 119.5(7) . . ?
N5 C15 C16 122.1(8) . . ?
N5 C15 H13 119.0 . . ?
C16 C15 H13 119.0 . . ?
C15 C16 C17 117.7(7) . . ?
C15 C16 H14 121.1 . . ?
C17 C16 H14 121.1 . . ?
C13 C17 C16 120.1(7) . . ?
C13 C17 C18 122.0(7) . . ?
C16 C17 C18 117.9(7) . . ?
N6 C18 O2 113.4(6) . . ?
N6 C18 C17 128.2(7) . . ?
O2 C18 C17 118.3(6) . . ?
C18 N6 N7 106.4(6) . . ?
C19 N7 N6 106.4(6) . . ?
N7 C19 O2 113.2(6) . . ?
N7 C19 C20 128.6(7) . . ?
O2 C19 C20 118.0(6) . . ?
C19 O2 C18 100.4(6) . . ?
C24 C20 C21 120.5(7) . . ?
C24 C20 C19 122.4(7) . . ?
C21 C20 C19 117.0(7) . . ?
C22 C21 C20 118.7(8) . . ?
C22 C21 H15 120.6 . . ?
C20 C21 H15 120.6 . . ?
N8 C22 C21 120.1(8) . . ?
N8 C22 H16 120.0 . . ?
C21 C22 H16 120.0 . . ?
C23 N8 C22 121.0(8) . . ?
C23 N8 H17 119.5 . . ?
C22 N8 H17 119.5 . . ?
N8 C23 C24 122.3(8) . . ?
N8 C23 H18 118.8 . . ?
C24 C23 H18 118.8 . . ?
C23 C24 C20 117.2(8) . . ?
C23 C24 H19 121.4 . . ?
C20 C24 H19 121.4 . . ?
C29 C25 C26 120.9(8) . . ?
C29 C25 H20 119.6 . . ?
C26 C25 H20 119.6 . . ?
N9 C26 C25 119.5(8) . . ?
N9 C26 H21 120.3 . . ?
C25 C26 H21 120.3 . . ?
C27 N9 C26 121.1(7) . . ?
C27 N9 H22 119.5 . . ?
C26 N9 H22 119.5 . . ?
N9 C27 C28 122.5(8) . . ?
N9 C27 H23 118.7 . . ?
C28 C27 H23 118.7 . . ?
C27 C28 C29 117.0(8) . . ?
C27 C28 H24 121.5 . . ?
C29 C28 H24 121.5 . . ?
C25 C29 C28 119.0(7) . . ?
C25 C29 C30 124.6(7) . . ?
C28 C29 C30 116.4(7) . . ?
N10 C30 O3 113.0(6) . . ?
N10 C30 C29 126.7(7) . . ?
O3 C30 C29 120.1(6) . . ?
C30 N10 N11 106.2(6) . . ?
C31 N11 N10 105.6(6) . . ?
N11 C31 O3 112.9(7) . . ?
N11 C31 C32 126.1(7) . . ?
O3 C31 C32 121.0(7) . . ?
C30 O3 C31 102.3(6) . . ?
C36 C32 C33 118.8(8) . . ?
C36 C32 C31 124.5(7) . . ?
C33 C32 C31 116.7(7) . . ?
C34 C33 C32 118.8(9) . . ?
C34 C33 H25 120.6 . . ?
C32 C33 H25 120.6 . . ?
N12 C34 C33 119.1(9) . . ?
N12 C34 H26 120.4 . . ?
C33 C34 H26 120.4 . . ?
C34 N12 C35 125.2(9) . . ?
C34 N12 H27 117.4 . . ?
C35 N12 H27 117.4 . . ?
N12 C35 C36 117.0(9) . . ?
N12 C35 H28 121.5 . . ?
C36 C35 H28 121.5 . . ?
C35 C36 C32 120.9(8) . . ?
C35 C36 H29 119.6 . . ?
C32 C36 H29 119.6 . . ?
I3 I2 I1 179.20(3) . . ?
I4 I5 I6 176.54(3) . . ?
I9 I8 I7 177.37(3) . . ?
H1O4 O4 H2O4 103.5 . . ?
H1O5 O5 H2O5 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.332
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.146
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1003928'
_audit_update_record             
;
2014-05-19 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H9 N4 O), 2(F6 P), H2 O'
_chemical_formula_sum            'C24 H20 F12 N8 O3 P2'
_chemical_formula_weight         758.42

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'
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'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.491(2)
_cell_length_b                   10.784(2)
_cell_length_c                   14.359(3)
_cell_angle_alpha                73.30(3)
_cell_angle_beta                 76.73(3)
_cell_angle_gamma                80.13(3)
_cell_volume                     1504.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13015
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.0

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             764
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13015
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.0
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5303
_reflns_number_gt                3404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.1131P)²+1.3698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5303
_refine_ls_number_parameters     479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0770
_refine_ls_wR_factor_ref         0.2344
_refine_ls_wR_factor_gt          0.2014
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5443(5) -0.0397(4) 0.3014(4) 0.0650(13) Uani 1 1 d . . .
H1 H 0.5804 -0.0655 0.3583 0.078 Uiso 1 1 calc R . .
C2 C 0.4794(6) -0.1238(5) 0.2770(4) 0.0742(15) Uani 1 1 d . . .
H2 H 0.4733 -0.2074 0.3184 0.089 Uiso 1 1 calc R . .
N1 N 0.4257(4) -0.0898(4) 0.1971(3) 0.0635(11) Uani 1 1 d . . .
C3 C 0.4355(5) 0.0295(5) 0.1360(4) 0.0646(14) Uani 1 1 d . . .
H3 H 0.3973 0.0530 0.0801 0.078 Uiso 1 1 calc R . .
C4 C 0.5003(4) 0.1176(5) 0.1535(3) 0.0581(12) Uani 1 1 d . . .
H4 H 0.5083 0.1990 0.1090 0.070 Uiso 1 1 calc R . .
C5 C 0.5540(4) 0.0846(4) 0.2382(3) 0.0470(10) Uani 1 1 d . . .
C6 C 0.6148(4) 0.1811(4) 0.2620(3) 0.0464(10) Uani 1 1 d . . .
N2 N 0.6160(4) 0.3031(4) 0.2190(3) 0.0564(10) Uani 1 1 d . . .
N3 N 0.6745(4) 0.3542(3) 0.2757(3) 0.0568(10) Uani 1 1 d . . .
C7 C 0.7041(4) 0.2575(4) 0.3474(3) 0.0455(10) Uani 1 1 d . . .
O1 O 0.6691(3) 0.1440(3) 0.3441(2) 0.0450(7) Uani 1 1 d . . .
C8 C 0.7647(4) 0.2580(4) 0.4290(3) 0.0497(10) Uani 1 1 d . . .
C9 C 0.8053(5) 0.1445(5) 0.4942(4) 0.0652(13) Uani 1 1 d . . .
H5 H 0.7960 0.0637 0.4869 0.078 Uiso 1 1 calc R . .
C10 C 0.8598(6) 0.1530(5) 0.5702(4) 0.0738(15) Uani 1 1 d . . .
H6 H 0.8862 0.0768 0.6150 0.089 Uiso 1 1 calc R . .
N4 N 0.8756(4) 0.2661(5) 0.5814(3) 0.0687(12) Uani 1 1 d . . .
H7 H 0.9092 0.2688 0.6299 0.082 Uiso 1 1 calc R . .
C11 C 0.8405(6) 0.3739(5) 0.5191(4) 0.0762(16) Uani 1 1 d . . .
H8 H 0.8550 0.4527 0.5269 0.091 Uiso 1 1 calc R . .
C12 C 0.7829(6) 0.3747(5) 0.4425(4) 0.0722(15) Uani 1 1 d . . .
H9 H 0.7563 0.4532 0.4001 0.087 Uiso 1 1 calc R . .
C13 C 0.7707(5) 0.3203(4) -0.0272(3) 0.0542(11) Uani 1 1 d . . .
H10 H 0.8219 0.2952 0.0215 0.065 Uiso 1 1 calc R . .
C14 C 0.7531(5) 0.2321(5) -0.0751(4) 0.0620(12) Uani 1 1 d . . .
H11 H 0.7932 0.1469 -0.0582 0.074 Uiso 1 1 calc R . .
N5 N 0.6801(4) 0.2660(4) -0.1449(3) 0.0621(11) Uani 1 1 d . . .
H12 H 0.6676 0.2088 -0.1720 0.075 Uiso 1 1 calc R . .
C15 C 0.6263(5) 0.3889(5) -0.1727(4) 0.0649(13) Uani 1 1 d . . .
H13 H 0.5781 0.4120 -0.2232 0.078 Uiso 1 1 calc R . .
C16 C 0.6400(5) 0.4822(5) -0.1291(3) 0.0576(12) Uani 1 1 d . . .
H14 H 0.6025 0.5676 -0.1500 0.069 Uiso 1 1 calc R . .
C17 C 0.7111(4) 0.4464(4) -0.0530(3) 0.0475(10) Uani 1 1 d . . .
C18 C 0.7150(4) 0.5411(4) 0.0006(3) 0.0465(10) Uani 1 1 d . . .
N6 N 0.6334(4) 0.6444(4) 0.0062(3) 0.0551(10) Uani 1 1 d . . .
N7 N 0.6734(4) 0.7001(4) 0.0700(3) 0.0555(9) Uani 1 1 d . . .
C19 C 0.7766(4) 0.6269(4) 0.0961(3) 0.0466(10) Uani 1 1 d . . .
O2 O 0.8090(3) 0.5229(3) 0.0563(2) 0.0470(7) Uani 1 1 d . . .
C20 C 0.8559(4) 0.6437(4) 0.1623(3) 0.0484(10) Uani 1 1 d . . .
C21 C 0.9485(5) 0.5461(4) 0.2014(3) 0.0557(11) Uani 1 1 d . . .
H15 H 0.9625 0.4660 0.1863 0.067 Uiso 1 1 calc R . .
C22 C 1.0189(5) 0.5699(5) 0.2626(3) 0.0608(12) Uani 1 1 d . . .
H16 H 1.0822 0.5053 0.2878 0.073 Uiso 1 1 calc R . .
N8 N 0.9994(4) 0.6842(4) 0.2877(3) 0.0607(11) Uani 1 1 d . . .
C23 C 0.9101(5) 0.7768(5) 0.2502(4) 0.0641(13) Uani 1 1 d . . .
H17 H 0.8961 0.8553 0.2678 0.077 Uiso 1 1 calc R . .
C24 C 0.8375(5) 0.7616(5) 0.1866(3) 0.0598(12) Uani 1 1 d . . .
H18 H 0.7773 0.8291 0.1605 0.072 Uiso 1 1 calc R . .
P1 P 0.04102(14) 0.13066(13) 0.16327(10) 0.0670(4) Uani 1 1 d . . .
F1 F 0.1647(4) 0.1803(4) 0.1759(4) 0.1313(16) Uani 1 1 d . A .
F2 F -0.0823(4) 0.0801(4) 0.1470(4) 0.1313(16) Uani 1 1 d . A .
F3 F 0.1018(4) -0.0151(4) 0.2045(4) 0.1249(15) Uani 1 1 d . A .
F4 F 0.1171(7) 0.1103(6) 0.0598(4) 0.184(3) Uani 1 1 d . A 1
F5 F -0.0232(12) 0.155(2) 0.2621(10) 0.164(6) Uani 0.65(2) 1 d P A 1
F5' F -0.025(3) 0.073(3) 0.2804(14) 0.149(10) Uani 0.35(2) 1 d P A 1
F6 F -0.036(2) 0.2687(10) 0.1391(18) 0.183(8) Uani 0.65(2) 1 d P A 1
F6' F 0.0241(17) 0.263(2) 0.0848(14) 0.117(8) Uani 0.35(2) 1 d P A 1
O3 O 0.4942(13) 0.5782(12) 0.3922(10) 0.335(7) Uani 1 1 d . B 1
H19 H 0.5603 0.6043 0.4027 0.502 Uiso 1 1 d R B 1
H20 H 0.5204 0.5168 0.3637 0.502 Uiso 1 1 d R B 1
P2 P 0.28007(16) 0.25769(16) 0.45435(12) 0.0826(5) Uani 1 1 d . A 1
F9 F 0.2173(5) 0.1454(3) 0.5398(3) 0.1299(15) Uani 1 1 d . A 1
F10 F 0.2885(6) 0.3213(4) 0.5393(4) 0.1439(18) Uani 1 1 d . A 1
F11 F 0.3428(7) 0.3734(7) 0.3758(4) 0.217(3) Uani 1 1 d . A 1
F12 F 0.1455(4) 0.3379(4) 0.4467(4) 0.1408(17) Uani 1 1 d . A 1
F7 F 0.3006(19) 0.1997(16) 0.3691(9) 0.175(6) Uani 0.65(2) 1 d P A 1
F7' F 0.206(4) 0.186(3) 0.395(2) 0.178(13) Uani 0.35(2) 1 d P A 1
F8 F 0.4300(11) 0.209(2) 0.4685(10) 0.164(6) Uani 0.65(2) 1 d P A 1
F8' F 0.389(2) 0.1388(19) 0.4629(16) 0.115(7) Uani 0.35(2) 1 d P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(6) . ?
C1 C5 1.391(6) . ?
C1 H1 0.9300 . ?
C2 N1 1.324(6) . ?
C2 H2 0.9300 . ?
N1 C3 1.339(6) . ?
C3 C4 1.366(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.462(5) . ?
C6 N2 1.283(5) . ?
C6 O1 1.355(5) . ?
N2 N3 1.396(5) . ?
N3 C7 1.290(5) . ?
C7 O1 1.352(5) . ?
C7 C8 1.457(5) . ?
C8 C12 1.378(6) . ?
C8 C9 1.380(6) . ?
C9 C10 1.374(6) . ?
C9 H5 0.9300 . ?
C10 N4 1.318(6) . ?
C10 H6 0.9300 . ?
N4 C11 1.301(6) . ?
N4 H7 0.8600 . ?
C11 C12 1.369(6) . ?
C11 H8 0.9300 . ?
C12 H9 0.9300 . ?
C13 C17 1.380(6) . ?
C13 C14 1.381(6) . ?
C13 H10 0.9300 . ?
C14 N5 1.330(6) . ?
C14 H11 0.9300 . ?
N5 C15 1.333(6) . ?
N5 H12 0.8600 . ?
C15 C16 1.370(6) . ?
C15 H13 0.9300 . ?
C16 C17 1.390(6) . ?
C16 H14 0.9300 . ?
C17 C18 1.455(5) . ?
C18 N6 1.293(5) . ?
C18 O2 1.362(4) . ?
N6 N7 1.399(5) . ?
N7 C19 1.288(5) . ?
C19 O2 1.359(5) . ?
C19 C20 1.465(5) . ?
C20 C24 1.383(6) . ?
C20 C21 1.388(6) . ?
C21 C22 1.370(6) . ?
C21 H15 0.9300 . ?
C22 N8 1.350(6) . ?
C22 H16 0.9300 . ?
N8 C23 1.329(6) . ?
C23 C24 1.374(6) . ?
C23 H17 0.9300 . ?
C24 H18 0.9300 . ?
P1 F5 1.500(9) . ?
P1 F6 1.551(9) . ?
P1 F1 1.551(4) . ?
P1 F6' 1.554(16) . ?
P1 F4 1.574(5) . ?
P1 F2 1.575(4) . ?
P1 F3 1.588(4) . ?
P1 F5' 1.644(19) . ?
F5 F5' 0.85(3) . ?
F6 F6' 0.89(2) . ?
O3 H19 0.8500 . ?
O3 H20 0.8500 . ?
P2 F7 1.486(11) . ?
P2 F12 1.534(4) . ?
P2 F11 1.547(6) . ?
P2 F9 1.567(4) . ?
P2 F10 1.587(5) . ?
P2 F8 1.611(11) . ?
P2 F7' 1.672(19) . ?
F7 F7' 1.00(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 118.1(4) . . ?
C2 C1 H1 121.0 . . ?
C5 C1 H1 121.0 . . ?
N1 C2 C1 122.6(5) . . ?
N1 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 N1 C3 119.5(4) . . ?
N1 C3 C4 121.7(4) . . ?
N1 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C1 118.7(4) . . ?
C4 C5 C6 120.1(4) . . ?
C1 C5 C6 121.1(4) . . ?
N2 C6 O1 113.0(3) . . ?
N2 C6 C5 128.5(4) . . ?
O1 C6 C5 118.3(4) . . ?
C6 N2 N3 106.0(3) . . ?
C7 N3 N2 106.0(3) . . ?
N3 C7 O1 112.9(3) . . ?
N3 C7 C8 128.4(4) . . ?
O1 C7 C8 118.7(4) . . ?
C7 O1 C6 102.1(3) . . ?
C12 C8 C9 118.1(4) . . ?
C12 C8 C7 119.8(4) . . ?
C9 C8 C7 122.1(4) . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 H5 120.6 . . ?
C8 C9 H5 120.6 . . ?
N4 C10 C9 121.8(5) . . ?
N4 C10 H6 119.1 . . ?
C9 C10 H6 119.1 . . ?
C11 N4 C10 120.2(4) . . ?
C11 N4 H7 119.9 . . ?
C10 N4 H7 119.9 . . ?
N4 C11 C12 122.0(5) . . ?
N4 C11 H8 119.0 . . ?
C12 C11 H8 119.0 . . ?
C11 C12 C8 119.2(5) . . ?
C11 C12 H9 120.4 . . ?
C8 C12 H9 120.4 . . ?
C17 C13 C14 118.8(4) . . ?
C17 C13 H10 120.6 . . ?
C14 C13 H10 120.6 . . ?
N5 C14 C13 121.5(5) . . ?
N5 C14 H11 119.2 . . ?
C13 C14 H11 119.2 . . ?
C14 N5 C15 119.9(4) . . ?
C14 N5 H12 120.0 . . ?
C15 N5 H12 120.0 . . ?
N5 C15 C16 121.9(4) . . ?
N5 C15 H13 119.0 . . ?
C16 C15 H13 119.0 . . ?
C15 C16 C17 118.6(4) . . ?
C15 C16 H14 120.7 . . ?
C17 C16 H14 120.7 . . ?
C13 C17 C16 119.1(4) . . ?
C13 C17 C18 121.8(4) . . ?
C16 C17 C18 119.1(4) . . ?
N6 C18 O2 112.3(3) . . ?
N6 C18 C17 127.3(4) . . ?
O2 C18 C17 120.3(4) . . ?
C18 N6 N7 106.4(3) . . ?
C19 N7 N6 106.0(3) . . ?
N7 C19 O2 113.0(3) . . ?
N7 C19 C20 127.4(4) . . ?
O2 C19 C20 119.7(4) . . ?
C19 O2 C18 102.3(3) . . ?
C24 C20 C21 119.0(4) . . ?
C24 C20 C19 118.6(4) . . ?
C21 C20 C19 122.5(4) . . ?
C22 C21 C20 118.8(4) . . ?
C22 C21 H15 120.6 . . ?
C20 C21 H15 120.6 . . ?
N8 C22 C21 122.2(5) . . ?
N8 C22 H16 118.9 . . ?
C21 C22 H16 118.9 . . ?
C23 N8 C22 118.5(4) . . ?
N8 C23 C24 122.8(4) . . ?
N8 C23 H17 118.6 . . ?
C24 C23 H17 118.6 . . ?
C23 C24 C20 118.7(5) . . ?
C23 C24 H18 120.7 . . ?
C20 C24 H18 120.7 . . ?
F5 P1 F6 74.9(16) . . ?
F5 P1 F1 86.4(6) . . ?
F6 P1 F1 94.0(6) . . ?
F5 P1 F6' 106.5(16) . . ?
F6 P1 F6' 33.4(8) . . ?
F1 P1 F6' 85.6(8) . . ?
F5 P1 F4 175.8(7) . . ?
F6 P1 F4 104.8(10) . . ?
F1 P1 F4 89.5(3) . . ?
F6' P1 F4 72.5(10) . . ?
F5 P1 F2 95.4(6) . . ?
F6 P1 F2 86.3(5) . . ?
F1 P1 F2 178.2(3) . . ?
F6' P1 F2 93.7(8) . . ?
F4 P1 F2 88.8(3) . . ?
F5 P1 F3 96.6(8) . . ?
F6 P1 F3 170.5(11) . . ?
F1 P1 F3 89.7(2) . . ?
F6' P1 F3 156.0(9) . . ?
F4 P1 F3 84.0(3) . . ?
F2 P1 F3 90.3(2) . . ?
F5 P1 F5' 30.9(10) . . ?
F6 P1 F5' 101.7(17) . . ?
F1 P1 F5' 99.6(10) . . ?
F6' P1 F5' 135.0(16) . . ?
F4 P1 F5' 151.3(12) . . ?
F2 P1 F5' 82.1(10) . . ?
F3 P1 F5' 69.0(10) . . ?
F5' F5 P1 84(2) . . ?
F5 F5' P1 65.2(15) . . ?
F6' F6 P1 73.5(14) . . ?
F6 F6' P1 73.1(14) . . ?
H19 O3 H20 109.5 . . ?
F7 P2 F12 100.7(7) . . ?
F7 P2 F11 84.0(8) . . ?
F12 P2 F11 87.6(3) . . ?
F7 P2 F9 100.1(8) . . ?
F12 P2 F9 92.3(3) . . ?
F11 P2 F9 175.8(4) . . ?
F7 P2 F10 168.7(8) . . ?
F12 P2 F10 88.5(3) . . ?
F11 P2 F10 89.8(4) . . ?
F9 P2 F10 86.1(2) . . ?
F7 P2 F8 91.1(7) . . ?
F12 P2 F8 164.3(9) . . ?
F11 P2 F8 83.3(7) . . ?
F9 P2 F8 95.8(7) . . ?
F10 P2 F8 78.7(8) . . ?
F7 P2 F7' 36.3(11) . . ?
F12 P2 F7' 74.0(14) . . ?
F11 P2 F7' 106.9(11) . . ?
F9 P2 F7' 77.0(11) . . ?
F10 P2 F7' 154.9(16) . . ?
F8 P2 F7' 121.0(11) . . ?
F7' F7 P2 82.0(18) . . ?
F7 F7' P2 61.7(13) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.067
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1003929'
_audit_update_record             
;
2014-05-19 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N4 O, 2(B F4), H2 O'
_chemical_formula_sum            'C12 H12 B2 F8 N4 O2'
_chemical_formula_weight         417.88

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   5.4030(11)
_cell_length_b                   19.358(4)
_cell_length_c                   16.265(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.94(3)
_cell_angle_gamma                90.00
_cell_volume                     1692.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17285
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17285
_diffrn_reflns_av_R_equivalents  0.1298
_diffrn_reflns_av_sigmaI/netI    0.1197
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3859
_reflns_number_gt                1650
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.1020P)²+1.2582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3859
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2162
_refine_ls_R_factor_gt           0.0915
_refine_ls_wR_factor_ref         0.2614
_refine_ls_wR_factor_gt          0.2035
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4739(9) 0.2037(2) 0.9921(3) 0.0477(12) Uani 1 1 d . . .
H1 H 0.3568 0.2252 0.9547 0.057 Uiso 1 1 calc R . .
C2 C 0.4459(9) 0.1355(3) 1.0139(3) 0.0542(13) Uani 1 1 d . . .
H2 H 0.3099 0.1102 0.9907 0.065 Uiso 1 1 calc R . .
N1 N 0.6158(8) 0.1061(2) 1.0687(2) 0.0549(11) Uani 1 1 d . . .
H3 H 0.5954 0.0635 1.0813 0.066 Uiso 1 1 calc R . .
C3 C 0.8152(10) 0.1392(2) 1.1047(3) 0.0537(13) Uani 1 1 d . . .
H4 H 0.9270 0.1166 1.1429 0.064 Uiso 1 1 calc R . .
C4 C 0.8527(9) 0.2067(2) 1.0845(3) 0.0494(12) Uani 1 1 d . . .
H5 H 0.9911 0.2306 1.1086 0.059 Uiso 1 1 calc R . .
C5 C 0.6809(8) 0.2393(2) 1.0275(3) 0.0401(11) Uani 1 1 d . . .
C6 C 0.7274(8) 0.3109(2) 1.0046(3) 0.0402(11) Uani 1 1 d . . .
N2 N 0.9223(7) 0.34744(19) 1.0261(2) 0.0522(11) Uani 1 1 d . . .
N3 N 0.8804(8) 0.41143(19) 0.9867(2) 0.0544(11) Uani 1 1 d . . .
O1 O 0.5539(5) 0.34495(14) 0.95398(17) 0.0417(8) Uani 1 1 d . . .
C7 C 0.6632(8) 0.4074(2) 0.9458(3) 0.0409(11) Uani 1 1 d . . .
C8 C 0.5350(8) 0.4604(2) 0.8950(3) 0.0421(11) Uani 1 1 d . . .
C9 C 0.3148(9) 0.4457(3) 0.8449(3) 0.0517(13) Uani 1 1 d . . .
H6 H 0.2474 0.4015 0.8432 0.062 Uiso 1 1 calc R . .
C10 C 0.2003(9) 0.4982(3) 0.7984(3) 0.0568(14) Uani 1 1 d . . .
H7 H 0.0545 0.4895 0.7643 0.068 Uiso 1 1 calc R . .
N4 N 0.2981(8) 0.5616(2) 0.8019(2) 0.0548(11) Uani 1 1 d . . .
H8 H 0.2229 0.5938 0.7727 0.066 Uiso 1 1 calc R . .
C11 C 0.5078(10) 0.5768(3) 0.8489(3) 0.0530(13) Uani 1 1 d . . .
H9 H 0.5712 0.6215 0.8491 0.064 Uiso 1 1 calc R . .
C12 C 0.6293(9) 0.5271(2) 0.8965(3) 0.0489(12) Uani 1 1 d . . .
H10 H 0.7747 0.5378 0.9298 0.059 Uiso 1 1 calc R . .
B1 B 0.8651(11) 0.0440(3) 0.8763(4) 0.0492(14) Uani 1 1 d . . .
F1 F 1.0945(7) 0.01445(18) 0.8760(3) 0.1039(13) Uani 1 1 d . A .
F2 F 0.7049(7) 0.00681(19) 0.9183(3) 0.1111(14) Uani 1 1 d . A .
F3 F 0.9037(7) 0.10552(19) 0.9155(3) 0.1066(14) Uani 1 1 d . A .
F4 F 0.771(3) 0.0689(6) 0.8009(9) 0.089(4) Uani 0.50 1 d P A 1
O2 O 0.6168(9) 0.8304(2) 0.2183(3) 0.1127(17) Uani 1 1 d . B 2
H11 H 0.4688 0.8458 0.1857 0.169 Uiso 1 1 d R B 2
H12 H 0.5920 0.7844 0.2378 0.169 Uiso 1 1 d R B 2
B2 B 0.1165(15) 0.7056(4) 0.2330(5) 0.074(2) Uani 1 1 d . . .
F5 F 0.368(3) 0.6935(13) 0.2300(11) 0.108(8) Uani 0.246(12) 1 d P C 1
F6 F 0.1303(8) 0.7541(2) 0.2932(2) 0.1189(15) Uani 1 1 d . C .
F7 F -0.151(3) 0.7021(10) 0.2293(13) 0.080(7) Uani 0.246(12) 1 d P C 1
F8 F 0.1309(12) 0.6425(2) 0.2650(3) 0.162(2) Uani 1 1 d . C 2
F7' F -0.069(2) 0.7104(4) 0.1744(6) 0.177(5) Uani 0.754(12) 1 d PD C 2
F5' F 0.277(2) 0.7205(6) 0.1812(7) 0.234(8) Uani 0.754(12) 1 d PD C 2
F4' F 0.777(3) 0.0362(12) 0.8010(8) 0.194(10) Uani 0.50 1 d P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(6) . ?
C1 C5 1.387(6) . ?
C1 H1 0.9300 . ?
C2 N1 1.338(6) . ?
C2 H2 0.9300 . ?
N1 C3 1.335(6) . ?
N1 H3 0.8600 . ?
C3 C4 1.368(6) . ?
C3 H4 0.9300 . ?
C4 C5 1.394(6) . ?
C4 H5 0.9300 . ?
C5 C6 1.462(6) . ?
C6 N2 1.288(5) . ?
C6 O1 1.353(5) . ?
N2 N3 1.403(5) . ?
N3 C7 1.290(5) . ?
O1 C7 1.358(5) . ?
C7 C8 1.448(6) . ?
C8 C12 1.387(6) . ?
C8 C9 1.400(6) . ?
C9 C10 1.375(7) . ?
C9 H6 0.9300 . ?
C10 N4 1.334(6) . ?
C10 H7 0.9300 . ?
N4 C11 1.332(6) . ?
N4 H8 0.8600 . ?
C11 C12 1.361(6) . ?
C11 H9 0.9300 . ?
C12 H10 0.9300 . ?
B1 F4' 1.276(13) . ?
B1 F3 1.357(6) . ?
B1 F2 1.362(6) . ?
B1 F4 1.365(13) . ?
B1 F1 1.365(6) . ?
O2 H11 0.9600 . ?
O2 H12 0.9600 . ?
B2 F5' 1.302(10) . ?
B2 F7' 1.315(10) . ?
B2 F8 1.326(8) . ?
B2 F6 1.353(8) . ?
B2 F5 1.384(17) . ?
B2 F7 1.440(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 118.3(4) . . ?
C2 C1 H1 120.8 . . ?
C5 C1 H1 120.8 . . ?
N1 C2 C1 119.5(4) . . ?
N1 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C3 N1 C2 123.6(4) . . ?
C3 N1 H3 118.2 . . ?
C2 N1 H3 118.2 . . ?
N1 C3 C4 119.1(5) . . ?
N1 C3 H4 120.5 . . ?
C4 C3 H4 120.5 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H5 120.4 . . ?
C5 C4 H5 120.4 . . ?
C1 C5 C4 120.2(4) . . ?
C1 C5 C6 121.2(4) . . ?
C4 C5 C6 118.6(4) . . ?
N2 C6 O1 113.1(4) . . ?
N2 C6 C5 127.5(4) . . ?
O1 C6 C5 119.4(4) . . ?
C6 N2 N3 105.8(3) . . ?
C7 N3 N2 106.1(4) . . ?
C6 O1 C7 102.3(3) . . ?
N3 C7 O1 112.7(4) . . ?
N3 C7 C8 127.4(4) . . ?
O1 C7 C8 120.0(4) . . ?
C12 C8 C9 119.1(4) . . ?
C12 C8 C7 119.8(4) . . ?
C9 C8 C7 121.1(4) . . ?
C10 C9 C8 118.5(5) . . ?
C10 C9 H6 120.7 . . ?
C8 C9 H6 120.7 . . ?
N4 C10 C9 120.1(5) . . ?
N4 C10 H7 119.9 . . ?
C9 C10 H7 119.9 . . ?
C11 N4 C10 122.5(4) . . ?
C11 N4 H8 118.7 . . ?
C10 N4 H8 118.7 . . ?
N4 C11 C12 120.1(5) . . ?
N4 C11 H9 119.9 . . ?
C12 C11 H9 119.9 . . ?
C11 C12 C8 119.6(5) . . ?
C11 C12 H10 120.2 . . ?
C8 C12 H10 120.2 . . ?
F4' B1 F3 125.3(11) . . ?
F4' B1 F2 103.1(9) . . ?
F3 B1 F2 107.7(5) . . ?
F4' B1 F4 27.5(13) . . ?
F3 B1 F4 97.8(7) . . ?
F2 B1 F4 116.1(8) . . ?
F4' B1 F1 101.2(10) . . ?
F3 B1 F1 105.9(5) . . ?
F2 B1 F1 113.8(5) . . ?
F4 B1 F1 113.5(8) . . ?
H11 O2 H12 109.5 . . ?
F5' B2 F7' 91.4(8) . . ?
F5' B2 F8 116.2(10) . . ?
F7' B2 F8 111.1(6) . . ?
F5' B2 F6 108.9(7) . . ?
F7' B2 F6 117.1(8) . . ?
F8 B2 F6 111.1(7) . . ?
F5' B2 F5 45.0(8) . . ?
F7' B2 F5 131.7(12) . . ?
F8 B2 F5 80.9(10) . . ?
F6 B2 F5 99.3(11) . . ?
F5' B2 F7 135.6(11) . . ?
F7' B2 F7 44.4(7) . . ?
F8 B2 F7 89.5(9) . . ?
F6 B2 F7 92.4(9) . . ?
F5 B2 F7 166.9(14) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.076
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1003930'
_audit_update_record             
;
2014-05-19 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N4 O, B F4'
_chemical_formula_sum            'C12 H9 B F4 N4 O'
_chemical_formula_weight         312.04

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.4767(17)
_cell_length_b                   8.9502(18)
_cell_length_c                   9.2925(19)
_cell_angle_alpha                80.43(3)
_cell_angle_beta                 78.98(3)
_cell_angle_gamma                80.97(3)
_cell_volume                     676.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7084
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7084
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_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         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3093
_reflns_number_gt                2110
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.1050P)²+0.2577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3093
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.2059
_refine_ls_wR_factor_gt          0.1845
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3435(3) 0.2916(3) 0.7227(3) 0.0500(7) Uani 1 1 d . . .
H1 H 0.2646 0.3760 0.7158 0.060 Uiso 1 1 calc R . .
C2 C 0.3642(3) 0.2095(3) 0.8582(3) 0.0559(7) Uani 1 1 d . . .
H2 H 0.2986 0.2398 0.9434 0.067 Uiso 1 1 calc R . .
N1 N 0.4763(3) 0.0868(2) 0.8704(2) 0.0513(6) Uani 1 1 d . . .
C3 C 0.5741(3) 0.0447(3) 0.7495(3) 0.0520(7) Uani 1 1 d . . .
H3 H 0.6530 -0.0394 0.7597 0.062 Uiso 1 1 calc R . .
C4 C 0.5620(3) 0.1214(3) 0.6104(3) 0.0485(6) Uani 1 1 d . . .
H4 H 0.6319 0.0907 0.5274 0.058 Uiso 1 1 calc R . .
C5 C 0.4428(3) 0.2459(3) 0.5967(3) 0.0408(6) Uani 1 1 d . . .
C6 C 0.4251(3) 0.3239(3) 0.4480(3) 0.0411(6) Uani 1 1 d . . .
N2 N 0.4963(3) 0.2810(3) 0.3243(2) 0.0540(6) Uani 1 1 d . . .
H10 H 0.5675 0.2024 0.3119 0.065 Uiso 1 1 calc R . .
N3 N 0.4359(3) 0.3868(3) 0.2137(2) 0.0538(6) Uani 1 1 d . . .
C7 C 0.3336(3) 0.4852(3) 0.2815(2) 0.0413(6) Uani 1 1 d . . .
O1 O 0.3194(2) 0.45355(18) 0.43176(16) 0.0419(4) Uani 1 1 d . . .
C8 C 0.2397(3) 0.6204(3) 0.2133(2) 0.0410(6) Uani 1 1 d . . .
C9 C 0.2692(3) 0.6566(3) 0.0607(3) 0.0530(7) Uani 1 1 d . . .
H5 H 0.3453 0.5946 0.0031 0.064 Uiso 1 1 calc R . .
C10 C 0.1848(4) 0.7851(3) -0.0041(3) 0.0558(7) Uani 1 1 d . . .
H6 H 0.2043 0.8094 -0.1066 0.067 Uiso 1 1 calc R . .
N4 N 0.0759(3) 0.8762(2) 0.0753(2) 0.0518(6) Uani 1 1 d . . .
C11 C 0.0458(4) 0.8423(3) 0.2237(3) 0.0543(7) Uani 1 1 d . . .
H8 H -0.0304 0.9068 0.2785 0.065 Uiso 1 1 calc R . .
C12 C 0.1250(3) 0.7148(3) 0.2960(3) 0.0481(6) Uani 1 1 d . . .
H9 H 0.1022 0.6921 0.3986 0.058 Uiso 1 1 calc R . .
B1 B 0.0255(4) 0.2458(4) 0.3057(4) 0.0576(8) Uani 1 1 d . . .
F1 F 0.1315(3) 0.2025(3) 0.4081(2) 0.0982(8) Uani 1 1 d . . .
F2 F -0.1042(2) 0.1647(2) 0.3490(2) 0.0798(6) Uani 1 1 d . . .
F3 F -0.0250(4) 0.3947(3) 0.3037(4) 0.1310(11) Uani 1 1 d . . .
F4 F 0.1086(2) 0.2080(3) 0.1718(2) 0.0841(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(3) . ?
C1 C5 1.385(4) . ?
C1 H1 0.9300 . ?
C2 N1 1.340(3) . ?
C2 H2 0.9300 . ?
N1 C3 1.333(4) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.465(3) . ?
C6 N2 1.282(3) . ?
C6 O1 1.356(3) . ?
N2 N3 1.393(3) . ?
N2 H10 0.8600 . ?
N3 C7 1.289(3) . ?
C7 O1 1.364(3) . ?
C7 C8 1.461(3) . ?
C8 C9 1.384(3) . ?
C8 C12 1.386(4) . ?
C9 C10 1.369(4) . ?
C9 H5 0.9300 . ?
C10 N4 1.328(4) . ?
C10 H6 0.9300 . ?
N4 C11 1.345(3) . ?
C11 C12 1.372(3) . ?
C11 H8 0.9300 . ?
C12 H9 0.9300 . ?
B1 F3 1.332(4) . ?
B1 F2 1.372(4) . ?
B1 F4 1.374(4) . ?
B1 F1 1.399(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 118.7(2) . . ?
C2 C1 H1 120.7 . . ?
C5 C1 H1 120.7 . . ?
N1 C2 C1 121.6(3) . . ?
N1 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C3 N1 C2 119.8(2) . . ?
N1 C3 C4 122.2(2) . . ?
N1 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C1 C5 C4 119.5(2) . . ?
C1 C5 C6 122.1(2) . . ?
C4 C5 C6 118.4(2) . . ?
N2 C6 O1 113.1(2) . . ?
N2 C6 C5 127.2(2) . . ?
O1 C6 C5 119.7(2) . . ?
C6 N2 N3 106.5(2) . . ?
C6 N2 H10 126.7 . . ?
N3 N2 H10 126.7 . . ?
C7 N3 N2 105.8(2) . . ?
N3 C7 O1 112.9(2) . . ?
N3 C7 C8 126.7(2) . . ?
O1 C7 C8 120.3(2) . . ?
C6 O1 C7 101.65(18) . . ?
C9 C8 C12 119.1(2) . . ?
C9 C8 C7 118.5(2) . . ?
C12 C8 C7 122.4(2) . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H5 120.5 . . ?
C8 C9 H5 120.5 . . ?
N4 C10 C9 121.9(2) . . ?
N4 C10 H6 119.0 . . ?
C9 C10 H6 119.0 . . ?
C10 N4 C11 119.8(2) . . ?
N4 C11 C12 121.5(3) . . ?
N4 C11 H8 119.3 . . ?
C12 C11 H8 119.3 . . ?
C11 C12 C8 118.8(2) . . ?
C11 C12 H9 120.6 . . ?
C8 C12 H9 120.6 . . ?
F3 B1 F2 109.9(3) . . ?
F3 B1 F4 113.7(3) . . ?
F2 B1 F4 108.8(3) . . ?
F3 B1 F1 107.9(3) . . ?
F2 B1 F1 109.2(3) . . ?
F4 B1 F1 107.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1003931'
_audit_update_record             
;
2014-05-19 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N4 O2, S O4'
_chemical_formula_sum            'C12 H12 N4 O6 S'
_chemical_formula_weight         340.32

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.2667(15)
_cell_length_b                   13.421(3)
_cell_length_c                   14.883(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.05(3)
_cell_angle_gamma                90.00
_cell_volume                     1408.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14393
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14393
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3233
_reflns_number_gt                2767
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0513P)²+0.4846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3230
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9126(2) 0.38176(13) 0.80460(11) 0.0269(3) Uani 1 1 d . . .
C2 C 0.7909(2) 0.37767(12) 0.87323(11) 0.0248(3) Uani 1 1 d . . .
C3 C 0.8755(2) 0.38837(13) 0.96696(12) 0.0306(4) Uani 1 1 d . . .
H1 H 1.0064 0.3949 0.9876 0.037 Uiso 1 1 calc R . .
C4 C 0.7621(3) 0.38913(14) 1.02888(12) 0.0363(4) Uani 1 1 d . . .
H2 H 0.8165 0.3960 1.0919 0.044 Uiso 1 1 calc R . .
N1 N 0.5739(2) 0.37998(12) 0.99849(11) 0.0360(4) Uani 1 1 d . . .
H3 H 0.5054 0.3806 1.0382 0.043 Uiso 1 1 calc R . .
C5 C 0.4890(3) 0.36998(15) 0.90908(13) 0.0368(4) Uani 1 1 d . . .
H4 H 0.3578 0.3638 0.8905 0.044 Uiso 1 1 calc R . .
C6 C 0.5954(2) 0.36882(13) 0.84408(12) 0.0307(4) Uani 1 1 d . . .
H5 H 0.5368 0.3622 0.7815 0.037 Uiso 1 1 calc R . .
N2 N 0.8506(2) 0.32488(12) 0.72935(10) 0.0311(3) Uani 1 1 d . . .
H6 H 0.7529 0.2873 0.7246 0.037 Uiso 1 1 calc R . .
N3 N 0.9464(2) 0.32748(12) 0.65902(9) 0.0315(3) Uani 1 1 d . . .
H7 H 1.0640 0.3108 0.6694 0.038 Uiso 1 1 calc R . .
C7 C 0.8502(2) 0.35680(13) 0.57458(12) 0.0283(4) Uani 1 1 d . . .
C8 C 0.9652(2) 0.36636(12) 0.50257(11) 0.0258(3) Uani 1 1 d . . .
C9 C 1.1617(3) 0.36122(15) 0.52326(13) 0.0367(4) Uani 1 1 d . . .
H8 H 1.2306 0.3461 0.5829 0.044 Uiso 1 1 calc R . .
C10 C 1.2532(3) 0.37901(16) 0.45351(13) 0.0390(4) Uani 1 1 d . . .
H9 H 1.3849 0.3767 0.4666 0.047 Uiso 1 1 calc R . .
N4 N 1.1548(2) 0.39943(12) 0.36792(10) 0.0345(3) Uani 1 1 d . . .
H10 H 1.2146 0.4103 0.3256 0.041 Uiso 1 1 calc R . .
C11 C 0.9657(3) 0.40345(15) 0.34582(12) 0.0361(4) Uani 1 1 d . . .
H11 H 0.9007 0.4173 0.2852 0.043 Uiso 1 1 calc R . .
C12 C 0.8665(3) 0.38726(14) 0.41224(12) 0.0331(4) Uani 1 1 d . . .
H12 H 0.7347 0.3903 0.3969 0.040 Uiso 1 1 calc R . .
O1 O 1.05653(18) 0.43269(11) 0.81895(9) 0.0392(3) Uani 1 1 d . . .
O2 O 0.68275(19) 0.37864(13) 0.55574(10) 0.0496(4) Uani 1 1 d . . .
O3 O 0.59485(17) 0.32976(10) 0.20701(9) 0.0375(3) Uani 1 1 d . . .
O4 O 0.3697(2) 0.43347(10) 0.25665(9) 0.0417(3) Uani 1 1 d . . .
O5 O 0.29157(18) 0.26326(10) 0.21672(9) 0.0388(3) Uani 1 1 d . . .
O6 O 0.31486(19) 0.38158(12) 0.09714(9) 0.0415(3) Uani 1 1 d . . .
S1 S 0.39236(5) 0.35115(3) 0.19419(3) 0.02535(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.224(2) . ?
C1 N2 1.340(2) . ?
C1 C2 1.506(2) . ?
C2 C6 1.386(2) . ?
C2 C3 1.388(2) . ?
C3 C4 1.377(3) . ?
C3 H1 0.9300 . ?
C4 N1 1.338(3) . ?
C4 H2 0.9300 . ?
N1 C5 1.331(2) . ?
N1 H3 0.8600 . ?
C5 C6 1.377(2) . ?
C5 H4 0.9300 . ?
C6 H5 0.9300 . ?
N2 N3 1.3911(19) . ?
N2 H6 0.8600 . ?
N3 C7 1.340(2) . ?
N3 H7 0.8600 . ?
C7 O2 1.217(2) . ?
C7 C8 1.516(2) . ?
C8 C9 1.387(2) . ?
C8 C12 1.390(2) . ?
C9 C10 1.382(2) . ?
C9 H8 0.9300 . ?
C10 N4 1.329(2) . ?
C10 H9 0.9300 . ?
N4 C11 1.333(2) . ?
N4 H10 0.8600 . ?
C11 C12 1.375(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
O3 S1 1.4655(13) . ?
O4 S1 1.4785(13) . ?
O5 S1 1.4695(13) . ?
O6 S1 1.4748(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 124.33(15) . . ?
O1 C1 C2 121.31(15) . . ?
N2 C1 C2 114.36(14) . . ?
C6 C2 C3 119.56(15) . . ?
C6 C2 C1 121.14(15) . . ?
C3 C2 C1 119.22(15) . . ?
C4 C3 C2 118.85(16) . . ?
C4 C3 H1 120.6 . . ?
C2 C3 H1 120.6 . . ?
N1 C4 C3 120.09(17) . . ?
N1 C4 H2 120.0 . . ?
C3 C4 H2 120.0 . . ?
C5 N1 C4 122.36(15) . . ?
C5 N1 H3 118.8 . . ?
C4 N1 H3 118.8 . . ?
N1 C5 C6 120.03(17) . . ?
N1 C5 H4 120.0 . . ?
C6 C5 H4 120.0 . . ?
C5 C6 C2 119.11(16) . . ?
C5 C6 H5 120.4 . . ?
C2 C6 H5 120.4 . . ?
C1 N2 N3 119.10(14) . . ?
C1 N2 H6 120.4 . . ?
N3 N2 H6 120.4 . . ?
C7 N3 N2 118.07(14) . . ?
C7 N3 H7 121.0 . . ?
N2 N3 H7 121.0 . . ?
O2 C7 N3 123.48(16) . . ?
O2 C7 C8 120.60(16) . . ?
N3 C7 C8 115.87(14) . . ?
C9 C8 C12 119.10(15) . . ?
C9 C8 C7 123.59(15) . . ?
C12 C8 C7 117.20(15) . . ?
C10 C9 C8 118.77(17) . . ?
C10 C9 H8 120.6 . . ?
C8 C9 H8 120.6 . . ?
N4 C10 C9 120.68(17) . . ?
N4 C10 H9 119.7 . . ?
C9 C10 H9 119.7 . . ?
C10 N4 C11 121.80(15) . . ?
C10 N4 H10 119.1 . . ?
C11 N4 H10 119.1 . . ?
N4 C11 C12 120.32(16) . . ?
N4 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C8 119.31(16) . . ?
C11 C12 H12 120.3 . . ?
C8 C12 H12 120.3 . . ?
O3 S1 O5 110.69(8) . . ?
O3 S1 O6 108.32(8) . . ?
O5 S1 O6 110.66(8) . . ?
O3 S1 O4 109.02(8) . . ?
O5 S1 O4 108.59(8) . . ?
O6 S1 O4 109.54(9) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.051
