# Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Kwang Lee'
_publ_contact_author_email       KMLEE@NKNU.EDU.TW

_publ_section_title              
;
Anion-Controlled Assemble of C-H---X Hydrogen
Bonded Helical Tubes or Catemers by Crescent Imidazolium Salts
;
loop_
_publ_author_name
'Kwang Lee'
'Jack C C Chen'
'Chao-June Huang'
'Ivan J. B. Lin'

data_1
_database_code_depnum_ccdc_archive 'CCDC 153355'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Br N5 O'
_chemical_formula_weight         284.13

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   26.020(6)
_cell_length_b                   7.128(2)
_cell_length_c                   11.941(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.79(2)
_cell_angle_gamma                90.00
_cell_volume                     2175.5(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10.63
_cell_measurement_theta_max      12.86

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.6
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    3.766
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_T_max  0.9360
_exptl_absorpt_process_details   ?

_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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 297
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        3.94
_diffrn_reflns_number            7247
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1908
_reflns_number_gt                1645
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_structure_solution    'Bruker SHELXS'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0663P)²+2.7284P] 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     SHELXL
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1908
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.071133(14) 0.18588(6) 0.57926(3) 0.0397(2) Uani 1 1 d . . .
O1 O 0.13521(10) 0.7624(5) 0.7768(3) 0.0472(7) Uani 1 1 d . . .
N1 N 0.15296(11) 0.6266(4) 0.4531(2) 0.0281(6) Uani 1 1 d . . .
N2 N 0.09189(11) 0.6812(4) 0.5469(3) 0.0302(7) Uani 1 1 d . . .
N3 N 0.23555(11) 0.5021(4) 0.5127(2) 0.0332(7) Uani 1 1 d . . .
N4 N 0.20815(12) 0.6100(5) 0.3224(3) 0.0385(7) Uani 1 1 d . . .
N5 N 0.05609(12) 0.7521(7) 0.8191(3) 0.0576(11) Uani 1 1 d . . .
H9 H 0.0669 0.7801 0.8896 0.069 Uiso 1 1 calc R . .
H10 H 0.0233 0.7330 0.7940 0.069 Uiso 1 1 calc R . .
C1 C 0.13849(12) 0.6032(5) 0.5533(3) 0.0293(7) Uani 1 1 d . . .
H1 H 0.1577 0.5429 0.6166 0.035 Uiso 1 1 calc R . .
C2 C 0.11398(15) 0.7190(6) 0.3795(3) 0.0367(9) Uani 1 1 d . . .
H2 H 0.1142 0.7518 0.3042 0.044 Uiso 1 1 calc R . .
C3 C 0.07548(15) 0.7522(6) 0.4385(3) 0.0369(8) Uani 1 1 d . . .
H3 H 0.0438 0.8117 0.4112 0.044 Uiso 1 1 calc R . .
C4 C 0.20239(13) 0.5744(5) 0.4275(3) 0.0284(7) Uani 1 1 d . . .
C5 C 0.25520(15) 0.5661(7) 0.3009(4) 0.0470(10) Uani 1 1 d . . .
H4 H 0.2621 0.5884 0.2284 0.056 Uiso 1 1 calc R . .
C6 C 0.29360(14) 0.4894(6) 0.3817(3) 0.0411(9) Uani 1 1 d . . .
H5 H 0.3262 0.4595 0.3656 0.049 Uiso 1 1 calc R . .
C7 C 0.28214(14) 0.4584(5) 0.4874(3) 0.0382(9) Uani 1 1 d . . .
H6 H 0.3075 0.4052 0.5436 0.046 Uiso 1 1 calc R . .
C8 C 0.06004(14) 0.6811(6) 0.6348(3) 0.0354(9) Uani 1 1 d . . .
H7 H 0.0459 0.5562 0.6402 0.042 Uiso 1 1 calc R . .
H8 H 0.0308 0.7659 0.6122 0.042 Uiso 1 1 calc R . .
C9 C 0.08929(15) 0.7387(6) 0.7504(3) 0.0384(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.189(5) . ?
N1 C1 1.330(5) . ?
N1 C2 1.379(5) . ?
N1 C4 1.426(4) . ?
N2 C1 1.323(5) . ?
N2 C3 1.381(5) . ?
N2 C8 1.454(5) . ?
N3 C4 1.310(4) . ?
N3 C7 1.340(5) . ?
N4 C4 1.317(5) . ?
N4 C5 1.334(5) . ?
N5 C9 1.301(5) . ?
C2 C3 1.349(6) . ?
C5 C6 1.367(6) . ?
C6 C7 1.368(6) . ?
C8 C9 1.503(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 109.5(3) . . ?
C1 N1 C4 125.3(3) . . ?
C2 N1 C4 125.0(3) . . ?
C1 N2 C3 109.1(3) . . ?
C1 N2 C8 126.8(3) . . ?
C3 N2 C8 124.0(3) . . ?
C4 N3 C7 114.1(3) . . ?
C4 N4 C5 114.3(3) . . ?
N2 C1 N1 107.8(3) . . ?
C3 C2 N1 106.3(3) . . ?
C2 C3 N2 107.2(3) . . ?
N3 C4 N4 129.8(3) . . ?
N3 C4 N1 115.2(3) . . ?
N4 C4 N1 115.0(3) . . ?
N4 C5 C6 122.2(4) . . ?
C5 C6 C7 117.4(3) . . ?
N3 C7 C6 122.2(4) . . ?
N2 C8 C9 113.8(3) . . ?
O1 C9 N5 125.1(4) . . ?
O1 C9 C8 126.3(4) . . ?
N5 C9 C8 108.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.102

#=END

data_2
_database_code_depnum_ccdc_archive 'CCDC 153356'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 F6 N5 O P'
_chemical_formula_weight         349.19

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.9852(16)
_cell_length_b                   24.937(2)
_cell_length_c                   8.9006(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.745(16)
_cell_angle_gamma                90.00
_cell_volume                     2787.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    21
_cell_measurement_theta_min      10.01
_cell_measurement_theta_max      12.92

_exptl_crystal_description       column
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.4
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7837
_exptl_absorpt_correction_T_max  0.8638
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 397
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        3.94
_diffrn_reflns_number            11693
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4925
_reflns_number_gt                3701
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_structure_solution    'Bruker SHELXS'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0583P)²+0.9559P] 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     SHELXL
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4925
_refine_ls_number_parameters     508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.106
_refine_ls_shift/su_mean         0.005

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
P1 P 0.36291(5) 0.34843(3) 0.49575(8) 0.0564(2) Uani 1 1 d . . .
P2 P 0.86570(5) 0.37355(3) 0.51170(7) 0.0536(2) Uani 1 1 d . . .
F1' F 0.3423(13) 0.2861(4) 0.5001(19) 0.147(5) Uani 0.448(17) 1 d P A 1
F2' F 0.2448(9) 0.3568(9) 0.496(2) 0.164(6) Uani 0.448(17) 1 d P A 1
F3' F 0.3825(11) 0.4014(5) 0.5305(17) 0.206(7) Uani 0.448(17) 1 d P A 1
F4' F 0.3930(13) 0.3304(8) 0.6690(15) 0.145(6) Uani 0.448(17) 1 d P A 1
F5' F 0.4780(7) 0.3394(7) 0.4949(17) 0.130(5) Uani 0.448(17) 1 d P A 1
F6' F 0.3285(10) 0.3661(5) 0.3242(13) 0.118(4) Uani 0.448(17) 1 d P A 1
F7' F 0.8479(9) 0.3161(4) 0.4331(15) 0.121(2) Uani 0.61(2) 1 d P B 2
F8' F 0.8916(8) 0.4305(3) 0.5524(17) 0.160(4) Uani 0.61(2) 1 d P B 2
F9' F 0.7482(6) 0.3729(5) 0.5234(11) 0.098(3) Uani 0.61(2) 1 d P B 2
F10' F 0.8960(12) 0.3588(6) 0.6885(10) 0.117(4) Uani 0.61(2) 1 d P B 2
F11' F 0.8305(6) 0.3900(4) 0.3337(9) 0.089(2) Uani 0.61(2) 1 d P B 2
F12' F 0.9836(4) 0.3673(4) 0.5023(10) 0.082(2) Uani 0.61(2) 1 d P B 2
F1 F 0.3801(8) 0.2907(3) 0.4430(11) 0.120(3) Uani 0.552(17) 1 d P A 3
F2 F 0.2476(7) 0.3382(5) 0.5030(14) 0.115(3) Uani 0.552(17) 1 d P A 3
F3 F 0.3528(9) 0.4128(3) 0.5285(8) 0.118(3) Uani 0.552(17) 1 d P A 3
F4 F 0.4061(10) 0.3454(5) 0.6771(12) 0.106(3) Uani 0.552(17) 1 d P A 3
F5 F 0.4794(6) 0.3590(6) 0.4867(15) 0.135(4) Uani 0.552(17) 1 d P A 3
F6 F 0.3210(7) 0.3531(5) 0.3147(10) 0.122(4) Uani 0.552(17) 1 d P A 3
F7 F 0.8124(17) 0.3188(8) 0.474(2) 0.134(5) Uani 0.39(2) 1 d P B 4
F8 F 0.9041(7) 0.4283(5) 0.6058(19) 0.109(4) Uani 0.39(2) 1 d P B 4
F9 F 0.7497(12) 0.3992(11) 0.5135(18) 0.120(6) Uani 0.39(2) 1 d P B 4
F10 F 0.8922(19) 0.3422(10) 0.671(2) 0.125(6) Uani 0.39(2) 1 d P B 4
F11 F 0.8422(12) 0.4020(6) 0.3531(18) 0.105(5) Uani 0.39(2) 1 d P B 4
F12 F 0.9755(10) 0.3554(7) 0.5032(17) 0.105(4) Uani 0.39(2) 1 d P B 4
O1 O 0.66454(15) 0.28261(7) 0.04826(19) 0.0639(5) Uani 1 1 d . . .
O2 O 1.10218(19) 0.21839(8) 0.5180(2) 0.0815(6) Uani 1 1 d . . .
N1 N 0.41906(13) 0.39333(7) 0.0207(2) 0.0429(4) Uani 1 1 d . . .
N2 N 0.52007(14) 0.33482(7) 0.1623(2) 0.0450(4) Uani 1 1 d . . .
N3 N 0.24232(15) 0.38770(8) -0.1121(3) 0.0617(6) Uani 1 1 d . . .
N4 N 0.34423(16) 0.46500(8) -0.1331(3) 0.0630(6) Uani 1 1 d . . .
N5 N 0.68832(18) 0.21711(8) 0.2259(2) 0.0642(6) Uani 1 1 d . . .
H10 H 0.7354 0.2010 0.1895 0.077 Uiso 1 1 calc R . .
H9 H 0.6704 0.2041 0.3051 0.077 Uiso 1 1 calc R . .
N6 N 0.88939(14) 0.09618(7) 0.5193(2) 0.0502(5) Uani 1 1 d . . .
N7 N 0.98111(16) 0.15924(8) 0.6541(2) 0.0562(5) Uani 1 1 d . . .
N8 N 0.71599(17) 0.09700(8) 0.3697(2) 0.0627(6) Uani 1 1 d . . .
N9 N 0.82320(17) 0.01906(8) 0.3845(3) 0.0658(6) Uani 1 1 d . . .
N10 N 1.15537(17) 0.27279(8) 0.7245(2) 0.0619(5) Uani 1 1 d . . .
H20 H 1.2028 0.2885 0.6881 0.074 Uiso 1 1 calc R . .
H19 H 1.1466 0.2821 0.8135 0.074 Uiso 1 1 calc R . .
C1 C 0.42696(17) 0.34213(8) 0.0660(3) 0.0455(5) Uani 1 1 d . . .
H1 H 0.3748 0.3160 0.0342 0.055 Uiso 1 1 calc R . .
C2 C 0.51207(17) 0.41901(9) 0.0931(3) 0.0559(6) Uani 1 1 d . . .
H2 H 0.5284 0.4549 0.0826 0.067 Uiso 1 1 calc R . .
C3 C 0.57443(19) 0.38243(9) 0.1815(3) 0.0609(7) Uani 1 1 d . . .
H3 H 0.6425 0.3882 0.2447 0.073 Uiso 1 1 calc R . .
C4 C 0.32842(17) 0.41710(9) -0.0827(3) 0.0464(5) Uani 1 1 d . . .
C5 C 0.1584(2) 0.41050(12) -0.2095(4) 0.0772(8) Uani 1 1 d . . .
H6 H 0.0941 0.3920 -0.2347 0.093 Uiso 1 1 calc R . .
C6 C 0.1631(2) 0.45961(12) -0.2733(4) 0.0823(9) Uani 1 1 d . . .
H5 H 0.1041 0.4747 -0.3422 0.099 Uiso 1 1 calc R . .
C7 C 0.2579(2) 0.48569(11) -0.2318(4) 0.0813(9) Uani 1 1 d . . .
H4 H 0.2632 0.5194 -0.2738 0.098 Uiso 1 1 calc R . .
C8 C 0.56198(19) 0.28435(9) 0.2354(3) 0.0513(6) Uani 1 1 d . . .
H8 H 0.5041 0.2589 0.2261 0.062 Uiso 1 1 calc R . .
H7 H 0.5939 0.2903 0.3451 0.062 Uiso 1 1 calc R . .
C9 C 0.64400(17) 0.26134(8) 0.1608(2) 0.0443(5) Uani 1 1 d . . .
C10 C 0.8887(2) 0.14772(9) 0.5606(3) 0.0519(6) Uani 1 1 d . . .
H11 H 0.8320 0.1714 0.5282 0.062 Uiso 1 1 calc R . .
C11 C 0.9869(2) 0.07515(11) 0.5926(3) 0.0712(8) Uani 1 1 d . . .
H12 H 1.0095 0.0401 0.5852 0.085 Uiso 1 1 calc R . .
C12 C 1.0432(2) 0.11453(11) 0.6763(4) 0.0767(8) Uani 1 1 d . . .
H13 H 1.1123 0.1119 0.7386 0.092 Uiso 1 1 calc R . .
C13 C 0.80322(19) 0.06886(9) 0.4173(3) 0.0505(5) Uani 1 1 d . . .
C14 C 0.6363(2) 0.07094(13) 0.2722(4) 0.0773(8) Uani 1 1 d . . .
H16 H 0.5719 0.0886 0.2336 0.093 Uiso 1 1 calc R . .
C15 C 0.6463(2) 0.01918(13) 0.2273(4) 0.0806(9) Uani 1 1 d . . .
H15 H 0.5905 0.0014 0.1592 0.097 Uiso 1 1 calc R . .
C16 C 0.7409(3) -0.00500(12) 0.2863(4) 0.0810(9) Uani 1 1 d . . .
H14 H 0.7494 -0.0402 0.2573 0.097 Uiso 1 1 calc R . .
C17 C 1.0158(2) 0.21153(10) 0.7208(3) 0.0635(7) Uani 1 1 d . . .
H17 H 1.0469 0.2079 0.8316 0.076 Uiso 1 1 calc R . .
H18 H 0.9551 0.2354 0.7056 0.076 Uiso 1 1 calc R . .
C18 C 1.0967(2) 0.23479(9) 0.6447(3) 0.0527(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
P1 F3' 1.365(11) . ?
P1 F5' 1.514(9) . ?
P1 F2 1.537(8) . ?
P1 F6' 1.542(10) . ?
P1 F1 1.548(7) . ?
P1 F2' 1.549(12) . ?
P1 F5 1.557(9) . ?
P1 F4' 1.558(13) . ?
P1 F6 1.569(8) . ?
P1 F4 1.570(10) . ?
P1 F1' 1.578(9) . ?
P1 F3 1.642(7) . ?
P2 F8' 1.482(8) . ?
P2 F12 1.516(10) . ?
P2 F7 1.528(14) . ?
P2 F11 1.540(11) . ?
P2 F9' 1.556(8) . ?
P2 F12' 1.562(6) . ?
P2 F10' 1.565(9) . ?
P2 F10 1.577(16) . ?
P2 F11' 1.587(7) . ?
P2 F7' 1.586(9) . ?
P2 F8 1.613(11) . ?
P2 F9 1.641(13) . ?
O1 C9 1.221(3) . ?
O2 C18 1.219(3) . ?
N1 C1 1.335(3) . ?
N1 C2 1.374(3) . ?
N1 C4 1.426(3) . ?
N2 C1 1.305(3) . ?
N2 C3 1.370(3) . ?
N2 C8 1.457(3) . ?
N3 C4 1.307(3) . ?
N3 C5 1.335(3) . ?
N4 C4 1.310(3) . ?
N4 C7 1.339(3) . ?
N5 C9 1.309(3) . ?
N6 C10 1.337(3) . ?
N6 C11 1.373(3) . ?
N6 C13 1.423(3) . ?
N7 C10 1.307(3) . ?
N7 C12 1.360(3) . ?
N7 C17 1.456(3) . ?
N8 C13 1.308(3) . ?
N8 C14 1.338(3) . ?
N9 C13 1.316(3) . ?
N9 C16 1.338(3) . ?
N10 C18 1.307(3) . ?
C2 C3 1.335(3) . ?
C5 C6 1.358(4) . ?
C6 C7 1.358(4) . ?
C8 C9 1.505(3) . ?
C11 C12 1.332(4) . ?
C14 C15 1.367(4) . ?
C15 C16 1.349(4) . ?
C17 C18 1.504(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
F3' P1 F5' 91.0(7) . . ?
F3' P1 F2 106.2(7) . . ?
F5' P1 F2 161.7(7) . . ?
F3' P1 F6' 86.5(8) . . ?
F5' P1 F6' 94.3(8) . . ?
F2 P1 F6' 92.8(7) . . ?
F3' P1 F1 159.3(6) . . ?
F5' P1 F1 69.0(6) . . ?
F2 P1 F1 94.3(5) . . ?
F6' P1 F1 89.6(6) . . ?
F3' P1 F2' 89.8(8) . . ?
F5' P1 F2' 179.1(8) . . ?
F2 P1 F2' 17.4(10) . . ?
F6' P1 F2' 85.8(8) . . ?
F1 P1 F2' 110.2(8) . . ?
F3' P1 F5 73.8(7) . . ?
F5' P1 F5 18.5(8) . . ?
F2 P1 F5 179.5(7) . . ?
F6' P1 F5 86.6(7) . . ?
F1 P1 F5 85.7(5) . . ?
F2' P1 F5 162.4(8) . . ?
F3' P1 F4' 94.0(10) . . ?
F5' P1 F4' 87.9(8) . . ?
F2 P1 F4' 84.9(8) . . ?
F6' P1 F4' 177.8(8) . . ?
F1 P1 F4' 90.7(9) . . ?
F2' P1 F4' 92.0(9) . . ?
F5 P1 F4' 95.6(8) . . ?
F3' P1 F6 99.0(7) . . ?
F5' P1 F6 95.2(7) . . ?
F2 P1 F6 88.2(6) . . ?
F6' P1 F6 12.6(8) . . ?
F1 P1 F6 78.3(6) . . ?
F2' P1 F6 84.8(8) . . ?
F5 P1 F6 91.3(6) . . ?
F4' P1 F6 166.6(8) . . ?
F3' P1 F4 79.4(7) . . ?
F5' P1 F4 84.4(8) . . ?
F2 P1 F4 92.6(7) . . ?
F6' P1 F4 165.8(6) . . ?
F1 P1 F4 103.0(6) . . ?
F2' P1 F4 95.6(8) . . ?
F5 P1 F4 87.9(7) . . ?
F4' P1 F4 15.0(10) . . ?
F6 P1 F4 178.4(6) . . ?
F3' P1 F1' 165.7(8) . . ?
F5' P1 F1' 91.6(7) . . ?
F2 P1 F1' 70.3(7) . . ?
F6' P1 F1' 107.3(9) . . ?
F1 P1 F1' 29.6(6) . . ?
F2' P1 F1' 87.6(7) . . ?
F5 P1 F1' 109.9(6) . . ?
F4' P1 F1' 72.1(12) . . ?
F6 P1 F1' 94.7(8) . . ?
F4 P1 F1' 86.9(7) . . ?
F3' P1 F3 14.8(8) . . ?
F5' P1 F3 105.7(6) . . ?
F2 P1 F3 91.9(5) . . ?
F6' P1 F3 83.1(5) . . ?
F1 P1 F3 170.7(4) . . ?
F2' P1 F3 75.2(8) . . ?
F5 P1 F3 88.1(5) . . ?
F4' P1 F3 96.8(7) . . ?
F6 P1 F3 95.0(5) . . ?
F4 P1 F3 83.6(5) . . ?
F1' P1 F3 159.4(8) . . ?
F8' P2 F12 98.1(7) . . ?
F8' P2 F7 166.0(10) . . ?
F12 P2 F7 95.8(8) . . ?
F8' P2 F11 76.2(7) . . ?
F12 P2 F11 93.5(8) . . ?
F7 P2 F11 103.8(11) . . ?
F8' P2 F9' 99.1(6) . . ?
F12 P2 F9' 162.0(6) . . ?
F7 P2 F9' 66.9(8) . . ?
F11 P2 F9' 95.5(6) . . ?
F8' P2 F12' 86.9(5) . . ?
F12 P2 F12' 11.7(8) . . ?
F7 P2 F12' 107.1(9) . . ?
F11 P2 F12' 88.0(6) . . ?
F9' P2 F12' 173.6(4) . . ?
F8' P2 F10' 89.8(6) . . ?
F12 P2 F10' 88.9(8) . . ?
F7 P2 F10' 89.6(10) . . ?
F11 P2 F10' 166.0(8) . . ?
F9' P2 F10' 86.0(7) . . ?
F12' P2 F10' 91.8(7) . . ?
F8' P2 F10 105.7(8) . . ?
F12 P2 F10 84.5(11) . . ?
F7 P2 F10 74.7(12) . . ?
F11 P2 F10 177.4(10) . . ?
F9' P2 F10 85.9(9) . . ?
F12' P2 F10 90.3(10) . . ?
F10' P2 F10 16.1(12) . . ?
F8' P2 F11' 89.2(5) . . ?
F12 P2 F11' 93.6(6) . . ?
F7 P2 F11' 90.8(8) . . ?
F11 P2 F11' 13.1(9) . . ?
F9' P2 F11' 91.8(4) . . ?
F12' P2 F11' 90.6(4) . . ?
F10' P2 F11' 177.4(6) . . ?
F10 P2 F11' 165.1(9) . . ?
F8' P2 F7' 166.4(8) . . ?
F12 P2 F7' 75.0(6) . . ?
F7 P2 F7' 24.4(6) . . ?
F11 P2 F7' 92.3(10) . . ?
F9' P2 F7' 89.1(4) . . ?
F12' P2 F7' 85.5(4) . . ?
F10' P2 F7' 101.7(8) . . ?
F10 P2 F7' 85.6(12) . . ?
F11' P2 F7' 79.7(7) . . ?
F8' P2 F8 16.6(8) . . ?
F12 P2 F8 96.3(7) . . ?
F7 P2 F8 158.8(12) . . ?
F11 P2 F8 92.8(8) . . ?
F9' P2 F8 98.8(6) . . ?
F12' P2 F8 86.3(4) . . ?
F10' P2 F8 73.2(7) . . ?
F10 P2 F8 89.1(9) . . ?
F11' P2 F8 105.8(6) . . ?
F7' P2 F8 170.1(6) . . ?
F8' P2 F9 77.0(10) . . ?
F12 P2 F9 174.1(9) . . ?
F7 P2 F9 89.1(8) . . ?
F11 P2 F9 82.0(9) . . ?
F9' P2 F9 23.7(8) . . ?
F12' P2 F9 162.7(9) . . ?
F10' P2 F9 94.5(9) . . ?
F10 P2 F9 100.1(13) . . ?
F11' P2 F9 83.0(7) . . ?
F7' P2 F9 109.0(8) . . ?
F8 P2 F9 80.1(8) . . ?
C1 N1 C2 108.26(17) . . ?
C1 N1 C4 125.45(18) . . ?
C2 N1 C4 126.28(18) . . ?
C1 N2 C3 108.83(18) . . ?
C1 N2 C8 126.34(19) . . ?
C3 N2 C8 124.82(19) . . ?
C4 N3 C5 114.0(2) . . ?
C4 N4 C7 113.4(2) . . ?
C10 N6 C11 107.9(2) . . ?
C10 N6 C13 125.2(2) . . ?
C11 N6 C13 126.95(19) . . ?
C10 N7 C12 109.1(2) . . ?
C10 N7 C17 126.5(2) . . ?
C12 N7 C17 124.4(2) . . ?
C13 N8 C14 114.4(2) . . ?
C13 N9 C16 113.5(2) . . ?
N2 C1 N1 108.62(18) . . ?
C3 C2 N1 106.7(2) . . ?
C2 C3 N2 107.6(2) . . ?
N3 C4 N4 130.1(2) . . ?
N3 C4 N1 114.8(2) . . ?
N4 C4 N1 115.11(19) . . ?
N3 C5 C6 122.7(3) . . ?
C5 C6 C7 116.9(2) . . ?
N4 C7 C6 122.9(3) . . ?
N2 C8 C9 110.96(18) . . ?
O1 C9 N5 124.5(2) . . ?
O1 C9 C8 121.55(19) . . ?
N5 C9 C8 113.98(19) . . ?
N7 C10 N6 108.5(2) . . ?
C12 C11 N6 107.0(2) . . ?
C11 C12 N7 107.6(2) . . ?
N8 C13 N9 129.6(2) . . ?
N8 C13 N6 115.2(2) . . ?
N9 C13 N6 115.2(2) . . ?
N8 C14 C15 122.2(3) . . ?
C16 C15 C14 117.0(3) . . ?
N9 C16 C15 123.4(3) . . ?
N7 C17 C18 109.9(2) . . ?
O2 C18 N10 125.7(2) . . ?
O2 C18 C17 120.0(2) . . ?
N10 C18 C17 114.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041


# END

data_2
_database_code_depnum_ccdc_archive 'CCDC 713462'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 N6 O4'
_chemical_formula_weight         266.23

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   P2(1)/c

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

_cell_length_a                   13.8870(4)
_cell_length_b                   7.1595(2)
_cell_length_c                   11.3891(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.5050(10)
_cell_angle_gamma                90.00
_cell_volume                     1116.80(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14511
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2764
_reflns_number_gt                2339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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)+(0.0595P)²+0.2009P] 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         2764
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.32278(7) 0.14020(13) -0.04014(8) 0.0281(2) Uani 1 1 d . . .
N2 N 0.20594(7) 0.11956(13) 0.06221(8) 0.0302(2) Uani 1 1 d . . .
N4 N 0.42971(7) 0.11449(15) -0.17605(8) 0.0353(2) Uani 1 1 d . . .
N3 N 0.47769(7) 0.26620(15) 0.01100(9) 0.0345(2) Uani 1 1 d . . .
C9 C 0.20208(8) 0.03659(16) 0.27204(10) 0.0299(2) Uani 1 1 d . . .
C6 C 0.59150(9) 0.23300(18) -0.12262(11) 0.0373(3) Uani 1 1 d . . .
C1 C 0.29372(8) 0.19086(16) 0.06177(10) 0.0301(2) Uani 1 1 d . . .
C5 C 0.52004(9) 0.1424(2) -0.20014(11) 0.0383(3) Uani 1 1 d . . .
C7 C 0.56678(9) 0.29457(18) -0.01692(12) 0.0372(3) Uani 1 1 d . . .
C3 C 0.17762(9) 0.02081(18) -0.04182(10) 0.0347(3) Uani 1 1 d . . .
C2 C 0.25001(9) 0.03291(17) -0.10612(10) 0.0332(3) Uani 1 1 d . . .
C8 C 0.15040(8) 0.13417(19) 0.15987(10) 0.0343(3) Uani 1 1 d . . .
N6 N 0.90877(7) 0.13767(15) 0.37827(9) 0.0360(2) Uani 1 1 d . . .
O4 O 0.82199(7) 0.11557(18) 0.39251(9) 0.0555(3) Uani 1 1 d . . .
O3 O 0.93648(7) 0.06481(18) 0.29050(9) 0.0555(3) Uani 1 1 d . . .
O2 O 0.96687(8) 0.22535(18) 0.45234(11) 0.0636(3) Uani 1 1 d . . .
O1 O 0.29028(6) 0.00897(14) 0.28775(8) 0.0419(2) Uani 1 1 d . . .
N5 N 0.14433(9) -0.00367(19) 0.34928(11) 0.0472(3) Uani 1 1 d . . .
H8 H 0.0875(13) 0.081(2) 0.1314(15) 0.050(4) Uiso 1 1 d . . .
H9 H 0.1667(13) -0.051(3) 0.4192(18) 0.061(5) Uiso 1 1 d . . .
C4 C 0.41640(8) 0.17828(15) -0.07087(9) 0.0276(2) Uani 1 1 d . . .
H1 H 0.3276(11) 0.264(2) 0.1191(13) 0.040(4) Uiso 1 1 d . . .
H7 H 0.1444(11) 0.262(2) 0.1763(13) 0.045(4) Uiso 1 1 d . . .
H5 H 0.6536(12) 0.246(2) -0.1409(13) 0.046(4) Uiso 1 1 d . . .
H2 H 0.2565(11) -0.019(2) -0.1815(15) 0.045(4) Uiso 1 1 d . . .
H3 H 0.1166(12) -0.044(2) -0.0576(14) 0.049(4) Uiso 1 1 d . . .
H4 H 0.5302(12) 0.094(2) -0.2740(15) 0.054(5) Uiso 1 1 d . . .
H6 H 0.6133(12) 0.354(2) 0.0397(15) 0.050(4) Uiso 1 1 d . . .
H10 H 0.0806(15) 0.016(2) 0.3302(16) 0.057(5) Uiso 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
N1 C1 1.3401(14) . ?
N1 C2 1.3875(14) . ?
N1 C4 1.4275(13) . ?
N2 C1 1.3224(14) . ?
N2 C3 1.3800(15) . ?
N2 C8 1.4582(14) . ?
N4 C4 1.3231(14) . ?
N4 C5 1.3426(15) . ?
N3 C4 1.3145(15) . ?
N3 C7 1.3428(15) . ?
C9 O1 1.2244(14) . ?
C9 N5 1.3164(15) . ?
C9 C8 1.5272(16) . ?
C6 C5 1.3768(19) . ?
C6 C7 1.3775(18) . ?
C3 C2 1.3407(17) . ?
N6 O2 1.2377(14) . ?
N6 O3 1.2436(14) . ?
N6 O4 1.2522(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 108.81(9) . . ?
C1 N1 C4 125.26(9) . . ?
C2 N1 C4 125.75(9) . . ?
C1 N2 C3 109.06(9) . . ?
C1 N2 C8 125.40(10) . . ?
C3 N2 C8 125.45(10) . . ?
C4 N4 C5 114.11(10) . . ?
C4 N3 C7 114.73(10) . . ?
O1 C9 N5 124.90(12) . . ?
O1 C9 C8 121.11(10) . . ?
N5 C9 C8 113.90(10) . . ?
C5 C6 C7 117.00(11) . . ?
N2 C1 N1 107.96(10) . . ?
N4 C5 C6 122.54(11) . . ?
N3 C7 C6 122.06(11) . . ?
C2 C3 N2 107.63(10) . . ?
C3 C2 N1 106.54(10) . . ?
N2 C8 C9 111.75(9) . . ?
O2 N6 O3 120.47(11) . . ?
O2 N6 O4 120.58(11) . . ?
O3 N6 O4 118.90(11) . . ?
N3 C4 N4 129.54(10) . . ?
N3 C4 N1 115.26(9) . . ?
N4 C4 N1 115.16(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.055

# END

data_4
_database_code_depnum_ccdc_archive 'CCDC 713463'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 B F4 N5 O'
_chemical_formula_weight         291.03

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   P2(1)/c

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

_cell_length_a                   15.0019(17)
_cell_length_b                   5.3086(6)
_cell_length_c                   15.7979(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.159(2)
_cell_angle_gamma                90.00
_cell_volume                     1165.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.87

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.80859
_exptl_absorpt_correction_T_max  0.96853
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8149
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2870
_reflns_number_gt                2235
_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)+(0.0509P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2870
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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
F1 F 0.28961(7) 0.06646(17) 0.41459(7) 0.0290(3) Uani 1 1 d . . .
F2 F 0.37376(6) 0.42615(18) 0.41916(7) 0.0272(3) Uani 1 1 d . . .
F3 F 0.24997(7) 0.42358(18) 0.47015(6) 0.0275(3) Uani 1 1 d . . .
F4 F 0.21915(7) 0.3874(2) 0.31844(6) 0.0324(3) Uani 1 1 d . . .
O1 O -0.43784(8) -0.2112(2) 0.31990(8) 0.0241(3) Uani 1 1 d . . .
N3 N -0.06603(9) -0.1967(2) 0.41519(8) 0.0165(3) Uani 1 1 d . . .
N4 N -0.04049(9) 0.1515(2) 0.33072(9) 0.0176(3) Uani 1 1 d . . .
N1 N -0.18078(8) 0.1236(2) 0.35773(8) 0.0138(3) Uani 1 1 d . . .
N2 N -0.31682(9) 0.1986(2) 0.36913(8) 0.0149(3) Uani 1 1 d . . .
N5 N -0.53185(9) -0.0674(3) 0.39216(9) 0.0199(3) Uani 1 1 d . . .
H9 H -0.5694 -0.2010 0.3778 0.024 Uiso 1 1 calc R . .
H10 H -0.5430 0.0547 0.4245 0.024 Uiso 1 1 calc R . .
B1 B 0.28289(12) 0.3273(3) 0.40527(12) 0.0177(4) Uani 1 1 d . . .
C7 C 0.02047(11) -0.2874(3) 0.42274(10) 0.0184(3) Uani 1 1 d . . .
H6 H 0.0424 -0.4402 0.4552 0.022 Uiso 1 1 calc R . .
C6 C 0.07870(11) -0.1679(3) 0.38535(10) 0.0193(3) Uani 1 1 d . . .
H5 H 0.1392 -0.2359 0.3907 0.023 Uiso 1 1 calc R . .
C5 C 0.04481(11) 0.0549(3) 0.33987(10) 0.0192(3) Uani 1 1 d . . .
H4 H 0.0836 0.1430 0.3141 0.023 Uiso 1 1 calc R . .
C4 C -0.08972(10) 0.0157(3) 0.36865(10) 0.0143(3) Uani 1 1 d . . .
C2 C -0.21871(11) 0.3357(3) 0.30576(10) 0.0171(3) Uani 1 1 d . . .
H2 H -0.1903 0.4303 0.2714 0.021 Uiso 1 1 calc R . .
C3 C -0.30307(11) 0.3818(3) 0.31328(10) 0.0171(3) Uani 1 1 d . . .
H3 H -0.3458 0.5163 0.2852 0.020 Uiso 1 1 calc R . .
C1 C -0.24230(10) 0.0421(3) 0.39540(10) 0.0150(3) Uani 1 1 d . . .
H1 H -0.2340 -0.1010 0.4337 0.018 Uiso 1 1 calc R . .
C8 C -0.39984(11) 0.1897(3) 0.39637(11) 0.0174(3) Uani 1 1 d . . .
H7 H -0.4418 0.3367 0.3701 0.021 Uiso 1 1 calc R . .
H8 H -0.3771 0.2015 0.4638 0.021 Uiso 1 1 calc R . .
C9 C -0.45798(10) -0.0501(3) 0.36487(10) 0.0156(3) 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
F1 B1 1.392(2) . ?
F2 B1 1.399(2) . ?
F3 B1 1.392(2) . ?
F4 B1 1.381(2) . ?
O1 C9 1.2203(18) . ?
N3 C4 1.320(2) . ?
N3 C7 1.3466(19) . ?
N4 C4 1.3259(19) . ?
N4 C5 1.3350(19) . ?
N1 C1 1.3444(18) . ?
N1 C2 1.3831(19) . ?
N1 C4 1.4304(18) . ?
N2 C1 1.3275(19) . ?
N2 C3 1.3798(19) . ?
N2 C8 1.4638(18) . ?
N5 C9 1.3352(19) . ?
N5 H9 0.8800 . ?
N5 H10 0.8800 . ?
C7 C6 1.380(2) . ?
C7 H6 0.9500 . ?
C6 C5 1.378(2) . ?
C6 H5 0.9500 . ?
C5 H4 0.9500 . ?
C2 C3 1.338(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C1 H1 0.9500 . ?
C8 C9 1.517(2) . ?
C8 H7 0.9900 . ?
C8 H8 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N3 C7 113.77(13) . . ?
C4 N4 C5 114.62(14) . . ?
C1 N1 C2 109.10(13) . . ?
C1 N1 C4 126.98(13) . . ?
C2 N1 C4 123.91(13) . . ?
C1 N2 C3 109.23(12) . . ?
C1 N2 C8 126.69(13) . . ?
C3 N2 C8 124.04(12) . . ?
C9 N5 H9 120.0 . . ?
C9 N5 H10 120.0 . . ?
H9 N5 H10 120.0 . . ?
F4 B1 F3 109.97(13) . . ?
F4 B1 F1 109.26(14) . . ?
F3 B1 F1 108.60(14) . . ?
F4 B1 F2 109.75(14) . . ?
F3 B1 F2 110.02(13) . . ?
F1 B1 F2 109.21(13) . . ?
N3 C7 C6 122.84(15) . . ?
N3 C7 H6 118.6 . . ?
C6 C7 H6 118.6 . . ?
C5 C6 C7 116.69(14) . . ?
C5 C6 H5 121.7 . . ?
C7 C6 H5 121.7 . . ?
N4 C5 C6 122.45(14) . . ?
N4 C5 H4 118.8 . . ?
C6 C5 H4 118.8 . . ?
N3 C4 N4 129.61(14) . . ?
N3 C4 N1 116.98(13) . . ?
N4 C4 N1 113.40(13) . . ?
C3 C2 N1 106.70(13) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 107.62(13) . . ?
C2 C3 H3 126.2 . . ?
N2 C3 H3 126.2 . . ?
N2 C1 N1 107.35(13) . . ?
N2 C1 H1 126.3 . . ?
N1 C1 H1 126.3 . . ?
N2 C8 C9 112.23(12) . . ?
N2 C8 H7 109.2 . . ?
C9 C8 H7 109.2 . . ?
N2 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
H7 C8 H8 107.9 . . ?
O1 C9 N5 123.90(14) . . ?
O1 C9 C8 122.75(14) . . ?
N5 C9 C8 113.35(13) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.056


