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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kh744

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Br1 N3 O1'
_chemical_formula_weight         278.10

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.8743(6)
_cell_length_b                   7.5065(7)
_cell_length_c                   13.3959(9)
_cell_angle_alpha                101.489(7)
_cell_angle_beta                 96.656(7)
_cell_angle_gamma                110.390(8)
_cell_volume                     531.44(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4449
_cell_measurement_theta_min      1.58
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.068
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    3.847
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4451
_exptl_absorpt_correction_T_max  0.7861
_exptl_absorpt_process_details   'shape of crystal determined optically'

_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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4449
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2096
_reflns_number_gt                1566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0669P)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         2096
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.007
_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 0.9818(10) 0.7202(8) 1.3615(4) 0.0505(12) Uani 1 1 d . . .
H1 H 0.8377 0.7010 1.3877 0.061 Uiso 1 1 calc R . .
C2 C 1.1982(10) 0.7440(9) 1.4265(4) 0.0515(13) Uani 1 1 d . . .
H2 H 1.1929 0.7379 1.4949 0.062 Uiso 1 1 calc R . .
C3 C 1.4039(9) 0.7797(7) 1.2961(3) 0.0414(10) Uani 1 1 d . . .
H3 H 1.5483 0.8004 1.2700 0.050 Uiso 1 1 calc R . .
C4 C 1.1898(8) 0.7551(6) 1.2315(3) 0.0342(9) Uani 1 1 d . . .
C5 C 1.2015(9) 0.7659(6) 1.1200(3) 0.0352(9) Uani 1 1 d . . .
C6 C 0.9298(9) 0.7453(6) 0.9575(3) 0.0352(9) Uani 1 1 d . . .
C7 C 1.1094(9) 0.8056(7) 0.9007(3) 0.0443(11) Uani 1 1 d . . .
H7 H 1.2758 0.8471 0.9314 0.053 Uiso 1 1 calc R . .
C8 C 1.0427(10) 0.8046(8) 0.7973(4) 0.0469(12) Uani 1 1 d . . .
H8 H 1.1643 0.8445 0.7587 0.056 Uiso 1 1 calc R . .
C9 C 0.7969(9) 0.7447(7) 0.7524(3) 0.0389(10) Uani 1 1 d . . .
C10 C 0.6169(9) 0.6837(8) 0.8078(3) 0.0445(11) Uani 1 1 d . . .
H10 H 0.4508 0.6421 0.7767 0.053 Uiso 1 1 calc R . .
C11 C 0.6825(9) 0.6839(8) 0.9109(3) 0.0440(11) Uani 1 1 d . . .
H11 H 0.5599 0.6427 0.9488 0.053 Uiso 1 1 calc R . .
N1 N 0.9764(7) 0.7245(6) 1.2623(3) 0.0443(9) Uani 1 1 d . . .
N2 N 1.4099(8) 0.7746(7) 1.3959(3) 0.0473(10) Uani 1 1 d . . .
N3 N 0.9816(7) 0.7427(6) 1.0625(3) 0.0394(9) Uani 1 1 d . . .
H3B H 0.8593 0.7243 1.0942 0.047 Uiso 1 1 calc R . .
O1 O 1.3894(7) 0.7882(6) 1.0888(3) 0.0552(9) Uani 1 1 d . . .
Br1 Br 0.70383(11) 0.74380(8) 0.61180(3) 0.0524(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.045(3) 0.078(4) 0.036(2) 0.020(2) 0.014(2) 0.027(3)
C2 0.058(3) 0.080(4) 0.028(2) 0.023(2) 0.009(2) 0.036(3)
C3 0.035(3) 0.058(3) 0.037(2) 0.017(2) 0.011(2) 0.020(2)
C4 0.040(3) 0.041(2) 0.0257(19) 0.0090(17) 0.0064(18) 0.020(2)
C5 0.038(3) 0.044(2) 0.0266(19) 0.0098(17) 0.0086(18) 0.018(2)
C6 0.043(3) 0.038(2) 0.0260(19) 0.0083(16) 0.0063(18) 0.018(2)
C7 0.043(3) 0.057(3) 0.033(2) 0.020(2) 0.005(2) 0.017(2)
C8 0.052(3) 0.062(3) 0.037(2) 0.023(2) 0.018(2) 0.025(3)
C9 0.052(3) 0.045(3) 0.0268(19) 0.0124(18) 0.007(2) 0.027(2)
C10 0.037(3) 0.061(3) 0.034(2) 0.010(2) -0.001(2) 0.020(2)
C11 0.039(3) 0.064(3) 0.035(2) 0.017(2) 0.013(2) 0.023(2)
N1 0.038(2) 0.069(3) 0.0292(18) 0.0176(18) 0.0045(16) 0.021(2)
N2 0.046(2) 0.070(3) 0.036(2) 0.0211(19) 0.0071(18) 0.030(2)
N3 0.038(2) 0.055(2) 0.0265(17) 0.0126(16) 0.0074(15) 0.0180(18)
O1 0.048(2) 0.090(3) 0.0380(17) 0.0272(18) 0.0137(16) 0.0308(19)
Br1 0.0719(4) 0.0635(4) 0.0262(2) 0.01340(19) 0.0035(2) 0.0321(3)

_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 N1 1.333(6) . ?
C1 C2 1.389(7) . ?
C1 H1 0.9300 . ?
C2 N2 1.313(7) . ?
C2 H2 0.9300 . ?
C3 N2 1.342(6) . ?
C3 C4 1.373(6) . ?
C3 H3 0.9300 . ?
C4 N1 1.323(6) . ?
C4 C5 1.520(5) . ?
C5 O1 1.194(5) . ?
C5 N3 1.360(6) . ?
C6 C7 1.373(6) . ?
C6 C11 1.386(7) . ?
C6 N3 1.411(5) . ?
C7 C8 1.394(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(7) . ?
C9 Br1 1.898(4) . ?
C10 C11 1.389(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
N3 H3B 0.8600 . ?

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
N1 C1 C2 121.4(4) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
N2 C2 C1 123.0(4) . . ?
N2 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
N2 C3 C4 121.7(4) . . ?
N2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
N1 C4 C3 123.0(4) . . ?
N1 C4 C5 119.0(4) . . ?
C3 C4 C5 118.0(4) . . ?
O1 C5 N3 125.5(4) . . ?
O1 C5 C4 120.8(4) . . ?
N3 C5 C4 113.7(4) . . ?
C7 C6 C11 119.4(4) . . ?
C7 C6 N3 123.6(4) . . ?
C11 C6 N3 117.0(4) . . ?
C6 C7 C8 120.1(5) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 Br1 119.2(3) . . ?
C8 C9 Br1 120.2(3) . . ?
C9 C10 C11 119.8(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C10 120.3(4) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C4 N1 C1 115.5(4) . . ?
C2 N2 C3 115.4(4) . . ?
C5 N3 C6 127.9(4) . . ?
C5 N3 H3B 116.0 . . ?
C6 N3 H3B 116.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 1.0(9) . . . . ?
N2 C3 C4 N1 -0.2(8) . . . . ?
N2 C3 C4 C5 179.2(4) . . . . ?
N1 C4 C5 O1 -178.0(4) . . . . ?
C3 C4 C5 O1 2.6(7) . . . . ?
N1 C4 C5 N3 0.3(6) . . . . ?
C3 C4 C5 N3 -179.1(4) . . . . ?
C11 C6 C7 C8 -0.1(7) . . . . ?
N3 C6 C7 C8 -179.6(5) . . . . ?
C6 C7 C8 C9 0.5(8) . . . . ?
C7 C8 C9 C10 -0.8(8) . . . . ?
C7 C8 C9 Br1 179.7(4) . . . . ?
C8 C9 C10 C11 0.6(7) . . . . ?
Br1 C9 C10 C11 -179.9(4) . . . . ?
C7 C6 C11 C10 -0.1(7) . . . . ?
N3 C6 C11 C10 179.5(4) . . . . ?
C9 C10 C11 C6 -0.2(7) . . . . ?
C3 C4 N1 C1 0.5(7) . . . . ?
C5 C4 N1 C1 -178.9(4) . . . . ?
C2 C1 N1 C4 -0.8(8) . . . . ?
C1 C2 N2 C3 -0.7(8) . . . . ?
C4 C3 N2 C2 0.2(7) . . . . ?
O1 C5 N3 C6 -1.9(8) . . . . ?
C4 C5 N3 C6 179.9(4) . . . . ?
C7 C6 N3 C5 -11.5(7) . . . . ?
C11 C6 N3 C5 168.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.110
_database_code_depnum_ccdc_archive 'CCDC 951196'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_khb7-abs1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 Br1 N4 O1'
_chemical_formula_weight         279.10

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   7.287(2)
_cell_length_b                   24.367(5)
_cell_length_c                   12.004(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.65(2)
_cell_angle_gamma                90.00
_cell_volume                     2094.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    16845
_cell_measurement_theta_min      1.92
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    3.907
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_T_max  0.9399
_exptl_absorpt_process_details   'shape of crystal determined optically'

_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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16845
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4092
_reflns_number_gt                3815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0639P)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         4092
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2004
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.2016
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.892
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6453(16) 0.2339(5) 1.2990(8) 0.052(3) Uani 1 1 d . . .
H1 H 0.6859 0.2695 1.2890 0.063 Uiso 1 1 calc R . .
C2 C 0.6486(18) 0.2156(6) 1.4041(11) 0.069(4) Uani 1 1 d . . .
H2 H 0.6879 0.2395 1.4642 0.083 Uiso 1 1 calc R . .
C3 C 0.5376(16) 0.1323(5) 1.3367(8) 0.054(3) Uani 1 1 d . . .
H3 H 0.5003 0.0965 1.3473 0.065 Uiso 1 1 calc R . .
C4 C 0.5303(14) 0.1518(4) 1.2281(8) 0.041(2) Uani 1 1 d . . .
C5 C 0.4615(13) 0.1151(4) 1.1288(8) 0.040(2) Uani 1 1 d . . .
C6 C 0.4216(14) 0.1117(4) 0.9182(8) 0.043(2) Uani 1 1 d . . .
C7 C 0.3623(16) 0.0576(5) 0.9025(8) 0.056(3) Uani 1 1 d . . .
H7 H 0.3510 0.0357 0.9642 0.067 Uiso 1 1 calc R . .
C8 C 0.3210(15) 0.0372(4) 0.7948(9) 0.052(3) Uani 1 1 d . . .
H8 H 0.2749 0.0018 0.7813 0.063 Uiso 1 1 calc R . .
C9 C 0.3491(16) 0.0700(5) 0.7074(8) 0.052(3) Uani 1 1 d . . .
C10 C 0.4059(15) 0.1233(4) 0.7262(9) 0.048(3) Uani 1 1 d . . .
H10 H 0.4175 0.1456 0.6651 0.057 Uiso 1 1 calc R . .
C11 C 0.8855(18) 0.1258(5) 1.6821(10) 0.062(3) Uani 1 1 d . . .
H11 H 0.8994 0.1566 1.6388 0.074 Uiso 1 1 calc R . .
C12 C 0.8366(15) 0.0754(6) 1.6265(9) 0.060(3) Uani 1 1 d . . .
H12 H 0.8240 0.0736 1.5481 0.072 Uiso 1 1 calc R . .
C13 C 0.8276(15) 0.0368(5) 1.7958(8) 0.053(3) Uani 1 1 d . . .
H13 H 0.8038 0.0068 1.8387 0.064 Uiso 1 1 calc R . .
C14 C 0.8813(15) 0.0855(5) 1.8498(8) 0.048(3) Uani 1 1 d . . .
C15 C 0.9049(15) 0.0889(5) 1.9768(8) 0.049(3) Uani 1 1 d . . .
C16 C 1.0165(16) 0.1545(5) 2.1350(9) 0.053(3) Uani 1 1 d . . .
C17 C 1.0029(16) 0.1203(4) 2.2237(8) 0.049(3) Uani 1 1 d . . .
H17 H 0.9637 0.0841 2.2115 0.059 Uiso 1 1 calc R . .
C18 C 1.0498(15) 0.1417(5) 2.3331(9) 0.053(3) Uani 1 1 d . . .
H18 H 1.0444 0.1201 2.3963 0.063 Uiso 1 1 calc R . .
C19 C 1.1047(14) 0.1960(4) 2.3444(7) 0.043(3) Uani 1 1 d . . .
C20 C 1.1197(15) 0.2255(5) 2.2504(8) 0.047(3) Uani 1 1 d . . .
H20 H 1.1640 0.2613 2.2604 0.056 Uiso 1 1 calc R . .
N1 N 0.5856(13) 0.2028(4) 1.2071(8) 0.056(2) Uani 1 1 d . . .
N2 N 0.5981(15) 0.1643(5) 1.4280(7) 0.067(3) Uani 1 1 d . . .
N3 N 0.4654(12) 0.1371(3) 1.0248(6) 0.044(2) Uani 1 1 d . . .
H3B H 0.4990 0.1710 1.0245 0.053 Uiso 1 1 calc R . .
N4 N 0.4456(12) 0.1439(4) 0.8331(7) 0.051(2) Uani 1 1 d . . .
N5 N 0.9121(13) 0.1305(4) 1.7934(7) 0.053(2) Uani 1 1 d . . .
N6 N 0.8086(14) 0.0312(4) 1.6829(8) 0.061(3) Uani 1 1 d . . .
N7 N 0.9723(12) 0.1385(3) 2.0205(7) 0.048(2) Uani 1 1 d . . .
H7B H 0.9898 0.1629 1.9718 0.057 Uiso 1 1 calc R . .
N8 N 1.0752(12) 0.2064(4) 2.1455(7) 0.050(2) Uani 1 1 d . . .
O1 O 0.4112(13) 0.0689(3) 1.1461(6) 0.068(2) Uani 1 1 d . . .
O2 O 0.8631(12) 0.0507(3) 2.0327(6) 0.069(2) Uani 1 1 d . . .
Br1 Br 0.30428(19) 0.04252(5) 0.55550(10) 0.0660(4) Uani 1 1 d . . .
Br2 Br 1.1693(2) 0.22704(5) 2.49109(9) 0.0686(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.067(8) 0.045(7) 0.040(6) -0.003(5) -0.003(5) -0.002(6)
C2 0.067(9) 0.068(10) 0.075(9) -0.005(7) 0.021(7) 0.009(7)
C3 0.064(8) 0.055(8) 0.044(6) 0.003(5) 0.011(5) 0.001(6)
C4 0.035(6) 0.040(7) 0.048(6) 0.001(5) 0.005(4) 0.009(5)
C5 0.034(6) 0.045(7) 0.043(6) -0.006(5) 0.013(4) -0.014(5)
C6 0.035(6) 0.032(6) 0.057(6) -0.006(5) -0.005(5) 0.004(5)
C7 0.067(8) 0.061(8) 0.040(6) 0.003(5) 0.009(5) -0.003(6)
C8 0.062(8) 0.037(7) 0.054(7) 0.003(5) -0.001(5) -0.001(5)
C9 0.053(8) 0.056(8) 0.044(6) -0.005(5) -0.004(5) 0.005(6)
C10 0.048(7) 0.047(7) 0.047(6) 0.000(5) 0.006(5) -0.007(5)
C11 0.081(10) 0.049(8) 0.057(7) 0.003(6) 0.018(6) -0.008(6)
C12 0.053(8) 0.085(10) 0.036(6) 0.016(6) -0.005(5) -0.003(7)
C13 0.063(8) 0.050(8) 0.045(6) 0.004(5) 0.008(5) -0.006(6)
C14 0.046(7) 0.047(7) 0.052(6) 0.002(5) 0.009(5) -0.004(5)
C15 0.054(8) 0.058(8) 0.036(5) 0.008(5) 0.017(5) 0.014(6)
C16 0.059(8) 0.047(8) 0.051(6) -0.004(5) 0.006(5) 0.008(6)
C17 0.070(8) 0.034(6) 0.046(6) 0.011(5) 0.016(5) 0.001(5)
C18 0.052(8) 0.045(7) 0.059(7) 0.014(5) 0.007(5) 0.003(5)
C19 0.038(7) 0.059(8) 0.030(5) -0.005(5) -0.001(4) 0.003(5)
C20 0.048(7) 0.045(7) 0.047(6) 0.007(5) 0.008(5) -0.001(5)
N1 0.066(7) 0.037(6) 0.065(6) 0.008(4) 0.014(5) 0.002(5)
N2 0.080(8) 0.074(8) 0.046(5) 0.000(5) 0.006(5) 0.010(6)
N3 0.053(6) 0.034(5) 0.044(5) 0.000(4) 0.008(4) 0.000(4)
N4 0.051(6) 0.042(6) 0.056(5) 0.004(4) 0.001(4) -0.010(4)
N5 0.072(7) 0.046(6) 0.041(5) 0.005(4) 0.008(4) -0.003(5)
N6 0.066(7) 0.058(7) 0.056(6) -0.011(5) 0.001(5) -0.006(5)
N7 0.056(6) 0.036(5) 0.048(5) 0.000(4) 0.002(4) -0.004(4)
N8 0.044(6) 0.045(6) 0.057(6) 0.001(4) 0.003(4) -0.004(4)
O1 0.096(7) 0.050(5) 0.063(5) 0.000(4) 0.025(4) -0.019(5)
O2 0.086(6) 0.055(6) 0.061(5) 0.009(4) -0.002(4) -0.015(4)
Br1 0.0746(9) 0.0660(9) 0.0551(7) -0.0095(6) 0.0057(6) 0.0044(7)
Br2 0.0913(11) 0.0600(8) 0.0487(6) -0.0091(5) -0.0022(6) 0.0103(7)

_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 1.335(16) . ?
C1 N1 1.342(13) . ?
C1 H1 0.9300 . ?
C2 N2 1.348(15) . ?
C2 H2 0.9300 . ?
C3 N2 1.351(14) . ?
C3 C4 1.379(14) . ?
C3 H3 0.9300 . ?
C4 N1 1.345(13) . ?
C4 C5 1.500(14) . ?
C5 O1 1.214(11) . ?
C5 N3 1.364(12) . ?
C6 N4 1.325(13) . ?
C6 C7 1.389(14) . ?
C6 N3 1.404(12) . ?
C7 C8 1.366(14) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(15) . ?
C9 Br1 1.913(10) . ?
C10 N4 1.358(13) . ?
C10 H10 0.9300 . ?
C11 N5 1.320(13) . ?
C11 C12 1.411(16) . ?
C11 H11 0.9300 . ?
C12 N6 1.308(14) . ?
C12 H12 0.9300 . ?
C13 N6 1.343(13) . ?
C13 C14 1.374(15) . ?
C13 H13 0.9300 . ?
C14 N5 1.329(13) . ?
C14 C15 1.504(14) . ?
C15 O2 1.218(12) . ?
C15 N7 1.372(13) . ?
C16 N8 1.335(13) . ?
C16 C17 1.371(14) . ?
C16 N7 1.408(13) . ?
C17 C18 1.395(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(13) . ?
C19 Br2 1.895(9) . ?
C20 N8 1.325(13) . ?
C20 H20 0.9300 . ?
N3 H3B 0.8600 . ?
N7 H7B 0.8600 . ?

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 N1 122.3(12) . . ?
C2 C1 H1 118.9 . . ?
N1 C1 H1 118.9 . . ?
C1 C2 N2 123.6(12) . . ?
C1 C2 H2 118.2 . . ?
N2 C2 H2 118.2 . . ?
N2 C3 C4 121.2(11) . . ?
N2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
N1 C4 C3 122.3(10) . . ?
N1 C4 C5 118.0(9) . . ?
C3 C4 C5 119.7(10) . . ?
O1 C5 N3 125.4(9) . . ?
O1 C5 C4 118.9(9) . . ?
N3 C5 C4 115.6(9) . . ?
N4 C6 C7 122.6(9) . . ?
N4 C6 N3 113.7(9) . . ?
C7 C6 N3 123.7(9) . . ?
C8 C7 C6 118.9(10) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C9 C8 C7 118.5(11) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 120.8(9) . . ?
C8 C9 Br1 120.3(9) . . ?
C10 C9 Br1 118.9(8) . . ?
N4 C10 C9 120.8(9) . . ?
N4 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N5 C11 C12 122.1(10) . . ?
N5 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
N6 C12 C11 121.5(10) . . ?
N6 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
N6 C13 C14 122.1(10) . . ?
N6 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
N5 C14 C13 122.1(10) . . ?
N5 C14 C15 118.2(10) . . ?
C13 C14 C15 119.7(9) . . ?
O2 C15 N7 124.8(9) . . ?
O2 C15 C14 121.5(11) . . ?
N7 C15 C14 113.6(9) . . ?
N8 C16 C17 124.9(10) . . ?
N8 C16 N7 111.5(9) . . ?
C17 C16 N7 123.7(10) . . ?
C16 C17 C18 117.6(10) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C19 C18 C17 117.8(9) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
C20 C19 C18 119.4(9) . . ?
C20 C19 Br2 121.0(8) . . ?
C18 C19 Br2 119.5(7) . . ?
N8 C20 C19 124.1(10) . . ?
N8 C20 H20 118.0 . . ?
C19 C20 H20 118.0 . . ?
C1 N1 C4 115.5(9) . . ?
C2 N2 C3 115.1(10) . . ?
C5 N3 C6 128.4(9) . . ?
C5 N3 H3B 115.8 . . ?
C6 N3 H3B 115.8 . . ?
C6 N4 C10 118.3(9) . . ?
C11 N5 C14 116.0(9) . . ?
C12 N6 C13 116.2(10) . . ?
C15 N7 C16 128.1(9) . . ?
C15 N7 H7B 115.9 . . ?
C16 N7 H7B 115.9 . . ?
C20 N8 C16 116.1(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 2(2) . . . . ?
N2 C3 C4 N1 1.3(17) . . . . ?
N2 C3 C4 C5 -179.7(10) . . . . ?
N1 C4 C5 O1 179.9(10) . . . . ?
C3 C4 C5 O1 0.9(15) . . . . ?
N1 C4 C5 N3 1.3(13) . . . . ?
C3 C4 C5 N3 -177.7(9) . . . . ?
N4 C6 C7 C8 -2.3(17) . . . . ?
N3 C6 C7 C8 179.2(10) . . . . ?
C6 C7 C8 C9 3.4(16) . . . . ?
C7 C8 C9 C10 -4.1(17) . . . . ?
C7 C8 C9 Br1 177.2(9) . . . . ?
C8 C9 C10 N4 3.6(17) . . . . ?
Br1 C9 C10 N4 -177.7(8) . . . . ?
N5 C11 C12 N6 2.5(19) . . . . ?
N6 C13 C14 N5 2.1(18) . . . . ?
N6 C13 C14 C15 -178.4(10) . . . . ?
N5 C14 C15 O2 173.4(10) . . . . ?
C13 C14 C15 O2 -6.1(16) . . . . ?
N5 C14 C15 N7 -5.2(14) . . . . ?
C13 C14 C15 N7 175.3(10) . . . . ?
N8 C16 C17 C18 1.5(18) . . . . ?
N7 C16 C17 C18 -179.5(10) . . . . ?
C16 C17 C18 C19 0.7(16) . . . . ?
C17 C18 C19 C20 -3.2(16) . . . . ?
C17 C18 C19 Br2 179.8(8) . . . . ?
C18 C19 C20 N8 3.8(16) . . . . ?
Br2 C19 C20 N8 -179.3(8) . . . . ?
C2 C1 N1 C4 -0.4(16) . . . . ?
C3 C4 N1 C1 -1.2(15) . . . . ?
C5 C4 N1 C1 179.8(9) . . . . ?
C1 C2 N2 C3 -1.8(18) . . . . ?
C4 C3 N2 C2 0.2(17) . . . . ?
O1 C5 N3 C6 -2.9(17) . . . . ?
C4 C5 N3 C6 175.6(9) . . . . ?
N4 C6 N3 C5 -177.8(10) . . . . ?
C7 C6 N3 C5 0.9(16) . . . . ?
C7 C6 N4 C10 1.7(16) . . . . ?
N3 C6 N4 C10 -179.6(9) . . . . ?
C9 C10 N4 C6 -2.4(16) . . . . ?
C12 C11 N5 C14 -3.1(17) . . . . ?
C13 C14 N5 C11 0.9(16) . . . . ?
C15 C14 N5 C11 -178.6(10) . . . . ?
C11 C12 N6 C13 0.5(17) . . . . ?
C14 C13 N6 C12 -2.7(17) . . . . ?
O2 C15 N7 C16 3.9(18) . . . . ?
C14 C15 N7 C16 -177.5(10) . . . . ?
N8 C16 N7 C15 -178.7(10) . . . . ?
C17 C16 N7 C15 2.2(18) . . . . ?
C19 C20 N8 C16 -1.6(16) . . . . ?
C17 C16 N8 C20 -1.1(17) . . . . ?
N7 C16 N8 C20 179.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.126
_database_code_depnum_ccdc_archive 'CCDC 951197'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_d:\determination\solution\857\new-kh857

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Cl1 N3 O1'
_chemical_formula_weight         233.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.8988(19)
_cell_length_b                   7.408(3)
_cell_length_c                   13.191(4)
_cell_angle_alpha                101.56(3)
_cell_angle_beta                 96.55(2)
_cell_angle_gamma                110.55(3)
_cell_volume                     518.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4692
_cell_measurement_theta_min      1.61
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9414
_exptl_absorpt_correction_T_max  0.9696
_exptl_absorpt_process_details   'shape of crystal determined optically'

_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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4692
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_sigmaI/netI    0.0985
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2260
_reflns_number_gt                2048
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.2000P)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         2260
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.5133(16) 0.2682(13) 0.1347(6) 0.069(2) Uani 1 1 d . . .
H1 H 0.6555 0.2881 0.1070 0.083 Uiso 1 1 calc R . .
C2 C 0.2955(16) 0.2433(14) 0.0698(6) 0.070(2) Uani 1 1 d . . .
H2 H 0.2977 0.2434 -0.0006 0.084 Uiso 1 1 calc R . .
C3 C 0.1008(15) 0.2171(12) 0.2028(6) 0.0589(19) Uani 1 1 d . . .
H3 H -0.0411 0.1999 0.2307 0.071 Uiso 1 1 calc R . .
C4 C 0.3117(14) 0.2385(12) 0.2685(5) 0.0562(18) Uani 1 1 d . . .
C5 C 0.3092(14) 0.2326(11) 0.3815(5) 0.0541(18) Uani 1 1 d . . .
C6 C 0.5739(14) 0.2548(12) 0.5461(6) 0.0580(18) Uani 1 1 d . . .
C7 C 0.3967(14) 0.1968(12) 0.6059(6) 0.062(2) Uani 1 1 d . . .
H7 H 0.2303 0.1538 0.5754 0.074 Uiso 1 1 calc R . .
C8 C 0.4651(15) 0.2023(13) 0.7112(6) 0.065(2) Uani 1 1 d . . .
H8 H 0.3454 0.1656 0.7515 0.078 Uiso 1 1 calc R . .
C9 C 0.7074(16) 0.2615(13) 0.7544(6) 0.066(2) Uani 1 1 d . . .
C10 C 0.8899(16) 0.3194(14) 0.6985(6) 0.070(2) Uani 1 1 d . . .
H10 H 1.0552 0.3615 0.7303 0.084 Uiso 1 1 calc R . .
C11 C 0.8231(15) 0.3138(13) 0.5935(7) 0.066(2) Uani 1 1 d . . .
H11 H 0.9446 0.3496 0.5538 0.079 Uiso 1 1 calc R . .
N1 N 0.5233(12) 0.2644(11) 0.2358(5) 0.0627(17) Uani 1 1 d . . .
N2 N 0.0871(14) 0.2195(12) 0.1022(6) 0.074(2) Uani 1 1 d . . .
N3 N 0.5243(11) 0.2565(10) 0.4395(5) 0.0598(17) Uani 1 1 d . . .
H3A H 0.6469 0.2752 0.4078 0.072 Uiso 1 1 calc R . .
O1 O 0.1174(11) 0.2129(10) 0.4146(5) 0.0747(17) Uani 1 1 d . . .
Cl1 Cl 0.7964(5) 0.2638(4) 0.88659(16) 0.0790(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.075(5) 0.109(7) 0.041(4) 0.031(4) 0.032(4) 0.043(5)
C2 0.067(5) 0.104(7) 0.043(4) 0.024(4) 0.016(4) 0.034(5)
C3 0.054(4) 0.078(5) 0.051(4) 0.022(4) 0.014(3) 0.028(4)
C4 0.062(5) 0.071(5) 0.037(3) 0.018(3) 0.009(3) 0.025(4)
C5 0.059(5) 0.065(5) 0.044(4) 0.023(3) 0.023(3) 0.022(4)
C6 0.055(4) 0.071(5) 0.053(4) 0.018(4) 0.018(4) 0.026(4)
C7 0.051(4) 0.081(5) 0.055(4) 0.030(4) 0.007(3) 0.022(4)
C8 0.058(5) 0.091(6) 0.049(4) 0.036(4) 0.014(4) 0.022(4)
C9 0.079(6) 0.085(6) 0.038(4) 0.026(4) 0.023(4) 0.028(5)
C10 0.061(5) 0.107(7) 0.045(4) 0.019(4) 0.014(4) 0.036(5)
C11 0.055(5) 0.089(6) 0.063(5) 0.029(4) 0.027(4) 0.030(4)
N1 0.057(4) 0.091(5) 0.048(3) 0.031(3) 0.022(3) 0.026(3)
N2 0.067(4) 0.099(5) 0.065(4) 0.038(4) 0.011(4) 0.033(4)
N3 0.056(4) 0.089(5) 0.042(3) 0.022(3) 0.019(3) 0.031(3)
O1 0.068(4) 0.115(5) 0.060(3) 0.043(3) 0.034(3) 0.040(3)
Cl1 0.0975(18) 0.1019(18) 0.0437(11) 0.0281(10) 0.0158(10) 0.0399(14)

_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 N1 1.334(9) . ?
C1 C2 1.392(11) . ?
C2 N2 1.313(11) . ?
C3 N2 1.325(10) . ?
C3 C4 1.373(10) . ?
C4 N1 1.330(10) . ?
C4 C5 1.502(9) . ?
C5 O1 1.230(8) . ?
C5 N3 1.339(10) . ?
C6 C7 1.381(10) . ?
C6 C11 1.404(11) . ?
C6 N3 1.407(10) . ?
C7 C8 1.390(10) . ?
C8 C9 1.354(12) . ?
C9 C10 1.368(11) . ?
C9 Cl1 1.757(8) . ?
C10 C11 1.385(11) . ?

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
N1 C1 C2 121.7(7) . . ?
N2 C2 C1 123.8(7) . . ?
N2 C3 C4 123.9(7) . . ?
N1 C4 C3 122.3(7) . . ?
N1 C4 C5 117.5(6) . . ?
C3 C4 C5 120.2(7) . . ?
O1 C5 N3 125.2(6) . . ?
O1 C5 C4 119.0(7) . . ?
N3 C5 C4 115.8(6) . . ?
C7 C6 C11 118.5(7) . . ?
C7 C6 N3 124.9(7) . . ?
C11 C6 N3 116.6(7) . . ?
C6 C7 C8 120.5(7) . . ?
C9 C8 C7 119.4(7) . . ?
C8 C9 C10 122.3(7) . . ?
C8 C9 Cl1 120.0(6) . . ?
C10 C9 Cl1 117.7(7) . . ?
C9 C10 C11 118.5(8) . . ?
C10 C11 C6 120.7(7) . . ?
C4 N1 C1 114.6(7) . . ?
C2 N2 C3 113.7(7) . . ?
C5 N3 C6 127.8(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 1.8(15) . . . . ?
N2 C3 C4 N1 0.2(13) . . . . ?
N2 C3 C4 C5 -179.6(7) . . . . ?
N1 C4 C5 O1 178.5(7) . . . . ?
C3 C4 C5 O1 -1.6(12) . . . . ?
N1 C4 C5 N3 0.7(11) . . . . ?
C3 C4 C5 N3 -179.4(7) . . . . ?
C11 C6 C7 C8 1.7(13) . . . . ?
N3 C6 C7 C8 -179.4(7) . . . . ?
C6 C7 C8 C9 -1.2(13) . . . . ?
C7 C8 C9 C10 0.9(14) . . . . ?
C7 C8 C9 Cl1 -178.5(6) . . . . ?
C8 C9 C10 C11 -1.0(14) . . . . ?
Cl1 C9 C10 C11 178.4(6) . . . . ?
C9 C10 C11 C6 1.5(13) . . . . ?
C7 C6 C11 C10 -1.9(13) . . . . ?
N3 C6 C11 C10 179.1(7) . . . . ?
C3 C4 N1 C1 0.1(12) . . . . ?
C5 C4 N1 C1 180.0(7) . . . . ?
C2 C1 N1 C4 -1.1(13) . . . . ?
C1 C2 N2 C3 -1.4(13) . . . . ?
C4 C3 N2 C2 0.4(12) . . . . ?
O1 C5 N3 C6 3.3(13) . . . . ?
C4 C5 N3 C6 -179.0(7) . . . . ?
C7 C6 N3 C5 10.6(13) . . . . ?
C11 C6 N3 C5 -170.5(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.158
_database_code_depnum_ccdc_archive 'CCDC 951198'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kh550

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 Cl1 N4 O1'
_chemical_formula_weight         234.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.375(4)
_cell_length_b                   10.920(5)
_cell_length_c                   13.606(7)
_cell_angle_alpha                86.20(4)
_cell_angle_beta                 83.56(4)
_cell_angle_gamma                73.19(4)
_cell_volume                     1041.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    11598
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      29.32

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   'shape of crystal determined optically'

_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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11598
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         29.32
_reflns_number_total             5587
_reflns_number_gt                4985
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0484P)²+0.1222P] 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         5587
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1620
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.5775(5) 0.2633(3) 0.2120(2) 0.0596(8) Uani 1 1 d . . .
H1 H 0.5369 0.2410 0.2760 0.072 Uiso 1 1 calc R . .
C2 C 0.5835(5) 0.3883(3) 0.1900(3) 0.0626(8) Uani 1 1 d . . .
H2 H 0.5489 0.4464 0.2405 0.075 Uiso 1 1 calc R . .
C3 C 0.6854(4) 0.3390(3) 0.0320(2) 0.0546(8) Uani 1 1 d . . .
H3 H 0.7213 0.3624 -0.0326 0.065 Uiso 1 1 calc R . .
C4 C 0.6847(4) 0.2141(2) 0.0538(2) 0.0440(6) Uani 1 1 d . . .
C5 C 0.7479(4) 0.1169(3) -0.0253(2) 0.0474(7) Uani 1 1 d . . .
C6 C 0.7951(4) -0.1156(2) -0.0460(2) 0.0461(7) Uani 1 1 d . . .
C7 C 0.8690(4) -0.1236(3) -0.1438(2) 0.0499(7) Uani 1 1 d . . .
H7 H 0.8894 -0.0522 -0.1793 0.060 Uiso 1 1 calc R . .
C8 C 0.9120(4) -0.2402(3) -0.1878(2) 0.0514(7) Uani 1 1 d . . .
H8 H 0.9598 -0.2489 -0.2540 0.062 Uiso 1 1 calc R . .
C9 C 0.8825(4) -0.3426(3) -0.1317(2) 0.0493(7) Uani 1 1 d . . .
C10 C 0.8079(4) -0.3280(3) -0.0349(2) 0.0521(7) Uani 1 1 d . . .
H10 H 0.7877 -0.3985 0.0020 0.063 Uiso 1 1 calc R . .
C11 C 0.5933(5) 0.7621(4) 0.2568(3) 0.0774(10) Uani 1 1 d . . .
H11 H 0.6284 0.7454 0.1901 0.093 Uiso 1 1 calc R . .
C12 C 0.4847(6) 0.8837(4) 0.2832(3) 0.0820(11) Uani 1 1 d . . .
H12 H 0.4511 0.9461 0.2333 0.098 Uiso 1 1 calc R . .
C13 C 0.4840(5) 0.8217(3) 0.4426(3) 0.0666(9) Uani 1 1 d . . .
H13 H 0.4486 0.8389 0.5091 0.080 Uiso 1 1 calc R . .
C14 C 0.5933(4) 0.7008(3) 0.4174(2) 0.0530(7) Uani 1 1 d . . .
C15 C 0.6537(4) 0.6003(3) 0.4949(2) 0.0526(7) Uani 1 1 d . . .
C16 C 0.8595(4) 0.3764(3) 0.5127(2) 0.0496(7) Uani 1 1 d . . .
C17 C 0.8328(5) 0.3617(3) 0.6149(2) 0.0582(8) Uani 1 1 d . . .
H17 H 0.7576 0.4289 0.6529 0.070 Uiso 1 1 calc R . .
C18 C 0.9186(5) 0.2472(3) 0.6582(2) 0.0599(8) Uani 1 1 d . . .
H18 H 0.9026 0.2341 0.7264 0.072 Uiso 1 1 calc R . .
C19 C 1.0305(4) 0.1503(3) 0.5988(2) 0.0570(8) Uani 1 1 d . . .
C20 C 1.0514(5) 0.1725(3) 0.4993(2) 0.0602(8) Uani 1 1 d . . .
H20 H 1.1280 0.1069 0.4601 0.072 Uiso 1 1 calc R . .
N1 N 0.6283(3) 0.1749(2) 0.14374(17) 0.0502(6) Uani 1 1 d . . .
N2 N 0.6358(4) 0.4279(2) 0.1011(2) 0.0627(7) Uani 1 1 d . . .
N3 N 0.7458(3) -0.0024(2) 0.00666(17) 0.0511(6) Uani 1 1 d . . .
H3B H 0.7088 -0.0103 0.0684 0.061 Uiso 1 1 calc R . .
N4 N 0.7632(4) -0.2143(2) 0.00838(17) 0.0513(6) Uani 1 1 d . . .
N5 N 0.6484(4) 0.6693(3) 0.32373(19) 0.0631(7) Uani 1 1 d . . .
N6 N 0.4271(4) 0.9151(3) 0.3750(3) 0.0772(8) Uani 1 1 d . . .
N7 N 0.7766(3) 0.4897(2) 0.46152(18) 0.0544(6) Uani 1 1 d . . .
H7B H 0.8083 0.4894 0.3987 0.065 Uiso 1 1 calc R . .
N8 N 0.9672(4) 0.2840(2) 0.45524(18) 0.0595(7) Uani 1 1 d . . .
O1 O 0.7960(4) 0.1464(2) -0.10939(16) 0.0748(7) Uani 1 1 d . . .
O2 O 0.5952(4) 0.6186(2) 0.58148(17) 0.0816(7) Uani 1 1 d . . .
Cl1 Cl 0.93971(14) -0.49324(7) -0.18199(7) 0.0730(3) Uani 1 1 d . . .
Cl2 Cl 1.14132(15) 0.00247(9) 0.65026(7) 0.0802(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.066(2) 0.0585(19) 0.0469(18) -0.0085(14) 0.0036(15) -0.0073(15)
C2 0.066(2) 0.0568(19) 0.060(2) -0.0178(16) -0.0030(17) -0.0072(16)
C3 0.067(2) 0.0470(16) 0.0484(18) -0.0004(13) -0.0053(15) -0.0148(14)
C4 0.0462(17) 0.0415(14) 0.0428(16) -0.0019(12) -0.0060(13) -0.0095(12)
C5 0.0533(18) 0.0469(16) 0.0407(17) -0.0032(12) -0.0035(14) -0.0120(13)
C6 0.0479(17) 0.0440(15) 0.0430(16) -0.0053(12) -0.0009(13) -0.0081(12)
C7 0.0560(19) 0.0494(16) 0.0413(16) -0.0008(12) 0.0013(13) -0.0128(13)
C8 0.0558(19) 0.0561(17) 0.0383(15) -0.0053(13) -0.0011(13) -0.0100(14)
C9 0.0493(18) 0.0422(15) 0.0529(18) -0.0126(13) -0.0076(14) -0.0042(13)
C10 0.062(2) 0.0424(15) 0.0524(18) -0.0025(13) -0.0020(15) -0.0158(14)
C11 0.079(3) 0.087(3) 0.053(2) 0.0015(19) -0.0009(18) -0.006(2)
C12 0.075(3) 0.084(3) 0.082(3) 0.016(2) -0.014(2) -0.016(2)
C13 0.062(2) 0.067(2) 0.064(2) -0.0136(17) 0.0039(17) -0.0086(17)
C14 0.0452(17) 0.0637(18) 0.0495(18) -0.0105(14) 0.0033(14) -0.0154(14)
C15 0.0541(19) 0.0589(18) 0.0454(18) -0.0090(14) 0.0029(14) -0.0184(15)
C16 0.0518(19) 0.0561(17) 0.0449(17) -0.0068(13) -0.0022(14) -0.0214(14)
C17 0.069(2) 0.064(2) 0.0411(17) -0.0131(14) 0.0030(15) -0.0193(16)
C18 0.066(2) 0.076(2) 0.0421(17) -0.0039(15) -0.0005(15) -0.0272(18)
C19 0.057(2) 0.0623(19) 0.057(2) 0.0020(15) -0.0046(16) -0.0263(16)
C20 0.066(2) 0.0595(19) 0.052(2) -0.0100(15) 0.0031(16) -0.0146(16)
N1 0.0590(16) 0.0446(12) 0.0422(13) -0.0021(10) 0.0024(11) -0.0100(11)
N2 0.0774(19) 0.0466(14) 0.0627(18) -0.0094(12) -0.0065(14) -0.0139(13)
N3 0.0687(17) 0.0421(12) 0.0381(13) -0.0046(10) 0.0086(12) -0.0133(11)
N4 0.0686(17) 0.0413(12) 0.0418(13) -0.0021(10) 0.0038(12) -0.0154(11)
N5 0.0659(18) 0.0706(17) 0.0466(16) -0.0098(13) 0.0049(13) -0.0116(14)
N6 0.069(2) 0.073(2) 0.080(2) -0.0079(17) -0.0013(17) -0.0074(15)
N7 0.0649(17) 0.0573(14) 0.0379(13) -0.0105(11) 0.0040(12) -0.0142(13)
N8 0.0679(18) 0.0626(16) 0.0458(15) -0.0118(12) 0.0062(13) -0.0174(14)
O1 0.126(2) 0.0550(12) 0.0425(13) -0.0017(10) 0.0051(13) -0.0299(13)
O2 0.0989(19) 0.0821(16) 0.0469(14) -0.0113(11) 0.0144(13) -0.0052(14)
Cl1 0.0887(7) 0.0526(4) 0.0740(6) -0.0252(4) -0.0053(5) -0.0102(4)
Cl2 0.0860(7) 0.0711(6) 0.0777(6) 0.0111(4) -0.0048(5) -0.0174(5)

_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 N1 1.329(4) . ?
C1 C2 1.390(4) . ?
C1 H1 0.9300 . ?
C2 N2 1.312(4) . ?
C2 H2 0.9300 . ?
C3 N2 1.341(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.331(3) . ?
C4 C5 1.502(4) . ?
C5 O1 1.210(3) . ?
C5 N3 1.349(3) . ?
C6 N4 1.330(3) . ?
C6 C7 1.378(4) . ?
C6 N3 1.405(3) . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(4) . ?
C9 Cl1 1.742(3) . ?
C10 N4 1.346(3) . ?
C10 H10 0.9300 . ?
C11 N5 1.321(4) . ?
C11 C12 1.385(5) . ?
C11 H11 0.9300 . ?
C12 N6 1.308(5) . ?
C12 H12 0.9300 . ?
C13 N6 1.333(4) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 N5 1.329(4) . ?
C14 C15 1.478(4) . ?
C15 O2 1.218(3) . ?
C15 N7 1.354(4) . ?
C16 N8 1.328(4) . ?
C16 C17 1.388(4) . ?
C16 N7 1.390(4) . ?
C17 C18 1.356(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(4) . ?
C19 Cl2 1.726(3) . ?
C20 N8 1.333(4) . ?
C20 H20 0.9300 . ?
N3 H3B 0.8600 . ?
N7 H7B 0.8600 . ?

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
N1 C1 C2 121.7(3) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
N2 C2 C1 122.9(3) . . ?
N2 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
N2 C3 C4 122.0(3) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
N1 C4 C3 122.3(2) . . ?
N1 C4 C5 117.7(2) . . ?
C3 C4 C5 120.0(3) . . ?
O1 C5 N3 124.7(3) . . ?
O1 C5 C4 121.3(2) . . ?
N3 C5 C4 114.0(2) . . ?
N4 C6 C7 123.5(2) . . ?
N4 C6 N3 112.9(2) . . ?
C7 C6 N3 123.6(3) . . ?
C6 C7 C8 118.4(3) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 118.4(3) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 Cl1 120.6(2) . . ?
C10 C9 Cl1 119.1(2) . . ?
N4 C10 C9 121.8(3) . . ?
N4 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
N5 C11 C12 121.7(4) . . ?
N5 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
N6 C12 C11 123.2(4) . . ?
N6 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
N6 C13 C14 122.3(3) . . ?
N6 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
N5 C14 C13 122.1(3) . . ?
N5 C14 C15 117.4(3) . . ?
C13 C14 C15 120.5(3) . . ?
O2 C15 N7 124.0(3) . . ?
O2 C15 C14 121.1(3) . . ?
N7 C15 C14 114.8(3) . . ?
N8 C16 C17 123.0(3) . . ?
N8 C16 N7 114.1(3) . . ?
C17 C16 N7 122.9(3) . . ?
C18 C17 C16 118.6(3) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 118.7(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 119.2(3) . . ?
C20 C19 Cl2 120.3(3) . . ?
C18 C19 Cl2 120.4(3) . . ?
N8 C20 C19 123.0(3) . . ?
N8 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
C1 N1 C4 115.7(2) . . ?
C2 N2 C3 115.5(3) . . ?
C5 N3 C6 129.5(2) . . ?
C5 N3 H3B 115.2 . . ?
C6 N3 H3B 115.2 . . ?
C6 N4 C10 117.7(2) . . ?
C11 N5 C14 115.6(3) . . ?
C12 N6 C13 115.1(3) . . ?
C15 N7 C16 130.2(3) . . ?
C15 N7 H7B 114.9 . . ?
C16 N7 H7B 114.9 . . ?
C16 N8 C20 117.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 1.3(5) . . . . ?
N2 C3 C4 N1 2.5(5) . . . . ?
N2 C3 C4 C5 -177.8(3) . . . . ?
N1 C4 C5 O1 177.9(3) . . . . ?
C3 C4 C5 O1 -1.7(4) . . . . ?
N1 C4 C5 N3 -2.2(4) . . . . ?
C3 C4 C5 N3 178.1(3) . . . . ?
N4 C6 C7 C8 0.1(4) . . . . ?
N3 C6 C7 C8 -180.0(3) . . . . ?
C6 C7 C8 C9 -1.2(4) . . . . ?
C7 C8 C9 C10 1.5(4) . . . . ?
C7 C8 C9 Cl1 -178.3(2) . . . . ?
C8 C9 C10 N4 -0.7(5) . . . . ?
Cl1 C9 C10 N4 179.2(2) . . . . ?
N5 C11 C12 N6 -0.9(6) . . . . ?
N6 C13 C14 N5 -0.3(5) . . . . ?
N6 C13 C14 C15 179.8(3) . . . . ?
N5 C14 C15 O2 -173.5(3) . . . . ?
C13 C14 C15 O2 6.4(5) . . . . ?
N5 C14 C15 N7 6.6(4) . . . . ?
C13 C14 C15 N7 -173.5(3) . . . . ?
N8 C16 C17 C18 -0.8(5) . . . . ?
N7 C16 C17 C18 179.5(3) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C17 C18 C19 Cl2 -179.5(3) . . . . ?
C18 C19 C20 N8 -0.6(5) . . . . ?
Cl2 C19 C20 N8 179.0(3) . . . . ?
C2 C1 N1 C4 -0.1(4) . . . . ?
C3 C4 N1 C1 -1.7(4) . . . . ?
C5 C4 N1 C1 178.6(3) . . . . ?
C1 C2 N2 C3 -0.6(5) . . . . ?
C4 C3 N2 C2 -1.2(5) . . . . ?
O1 C5 N3 C6 -0.2(5) . . . . ?
C4 C5 N3 C6 180.0(3) . . . . ?
N4 C6 N3 C5 -175.8(3) . . . . ?
C7 C6 N3 C5 4.3(5) . . . . ?
C7 C6 N4 C10 0.7(4) . . . . ?
N3 C6 N4 C10 -179.2(3) . . . . ?
C9 C10 N4 C6 -0.5(4) . . . . ?
C12 C11 N5 C14 -0.3(5) . . . . ?
C13 C14 N5 C11 0.8(5) . . . . ?
C15 C14 N5 C11 -179.3(3) . . . . ?
C11 C12 N6 C13 1.4(6) . . . . ?
C14 C13 N6 C12 -0.8(5) . . . . ?
O2 C15 N7 C16 1.0(5) . . . . ?
C14 C15 N7 C16 -179.2(3) . . . . ?
N8 C16 N7 C15 176.8(3) . . . . ?
C17 C16 N7 C15 -3.5(5) . . . . ?
C17 C16 N8 C20 0.3(4) . . . . ?
N7 C16 N8 C20 -180.0(3) . . . . ?
C19 C20 N8 C16 0.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        29.32
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 951199'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_new

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 F1 N3 O1'
_chemical_formula_weight         217.20

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   6.0141(15)
_cell_length_b                   23.974(5)
_cell_length_c                   13.582(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.58(2)
_cell_angle_gamma                90.00
_cell_volume                     1956.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    21289
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      29.22

_exptl_crystal_description       CPlate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'SADABS (Sheldric, 1998a)'

_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  'APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21289
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_sigmaI/netI    0.1026
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         29.22
_reflns_number_total             5283
_reflns_number_gt                4152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0405P)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         5283
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1738
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_restrained_S_all      0.864
_refine_ls_shift/su_max          0.002
_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
C1 C 0.9869(4) 0.18922(9) 0.9255(2) 0.0649(7) Uani 1 1 d . . .
H1 H 1.1271 0.2053 0.9222 0.078 Uiso 1 1 calc R . .
C2 C 0.8108(4) 0.22254(9) 0.9471(2) 0.0625(7) Uani 1 1 d . . .
H2 H 0.8356 0.2604 0.9580 0.075 Uiso 1 1 calc R . .
C3 C 0.5841(4) 0.14806(9) 0.93600(18) 0.0554(6) Uani 1 1 d . . .
H3 H 0.4436 0.1321 0.9389 0.066 Uiso 1 1 calc R . .
C4 C 0.7604(4) 0.11458(8) 0.91459(17) 0.0438(5) Uani 1 1 d . . .
C5 C 0.7227(4) 0.05341(9) 0.89680(16) 0.0452(6) Uani 1 1 d . . .
C6 C 0.9287(4) -0.03383(8) 0.86309(16) 0.0428(5) Uani 1 1 d . . .
C7 C 0.7585(4) -0.07160(9) 0.87567(18) 0.0544(7) Uani 1 1 d . . .
H7 H 0.6237 -0.0596 0.8991 0.065 Uiso 1 1 calc R . .
C8 C 0.7889(4) -0.12730(9) 0.8535(2) 0.0597(7) Uani 1 1 d . . .
H8 H 0.6742 -0.1528 0.8606 0.072 Uiso 1 1 calc R . .
C9 C 0.9869(4) -0.14420(9) 0.82124(19) 0.0559(7) Uani 1 1 d . . .
C10 C 1.1598(4) -0.10843(10) 0.80988(19) 0.0593(7) Uani 1 1 d . . .
H10 H 1.2954 -0.1212 0.7885 0.071 Uiso 1 1 calc R . .
C11 C 1.1285(4) -0.05244(9) 0.83093(18) 0.0550(6) Uani 1 1 d . . .
H11 H 1.2441 -0.0273 0.8232 0.066 Uiso 1 1 calc R . .
C12 C 0.5090(4) -0.13399(9) 0.59073(19) 0.0583(7) Uani 1 1 d . . .
H12 H 0.3688 -0.1501 0.5945 0.070 Uiso 1 1 calc R . .
C13 C 0.6848(4) -0.16722(9) 0.56846(18) 0.0557(7) Uani 1 1 d . . .
H13 H 0.6595 -0.2050 0.5574 0.067 Uiso 1 1 calc R . .
C14 C 0.9127(4) -0.09308(9) 0.57840(18) 0.0510(6) Uani 1 1 d . . .
H14 H 1.0530 -0.0772 0.5744 0.061 Uiso 1 1 calc R . .
C15 C 0.7363(4) -0.05923(8) 0.60108(16) 0.0417(5) Uani 1 1 d . . .
C16 C 0.7754(4) 0.00196(9) 0.61928(16) 0.0462(6) Uani 1 1 d . . .
C17 C 0.5681(4) 0.08879(8) 0.65530(16) 0.0437(5) Uani 1 1 d . . .
C18 C 0.7387(4) 0.12658(8) 0.64397(18) 0.0513(6) Uani 1 1 d . . .
H18 H 0.8755 0.1145 0.6227 0.062 Uiso 1 1 calc R . .
C19 C 0.7049(4) 0.18244(9) 0.66444(19) 0.0564(7) Uani 1 1 d . . .
H19 H 0.8188 0.2081 0.6570 0.068 Uiso 1 1 calc R . .
C20 C 0.5058(4) 0.19944(9) 0.69521(19) 0.0573(7) Uani 1 1 d . . .
C21 C 0.3337(4) 0.16328(10) 0.7064(2) 0.0627(7) Uani 1 1 d . . .
H21 H 0.1973 0.1759 0.7272 0.075 Uiso 1 1 calc R . .
C22 C 0.3665(4) 0.10722(9) 0.68629(18) 0.0554(6) Uani 1 1 d . . .
H22 H 0.2513 0.0819 0.6938 0.066 Uiso 1 1 calc R . .
N1 N 0.9657(3) 0.13479(7) 0.90919(15) 0.0556(5) Uani 1 1 d . . .
N2 N 0.6060(3) 0.20267(7) 0.95289(16) 0.0638(6) Uani 1 1 d . . .
N3 N 0.9086(3) 0.02396(7) 0.88345(14) 0.0488(5) Uani 1 1 d . . .
H3B H 1.0312 0.0425 0.8878 0.059 Uiso 1 1 calc R . .
N4 N 0.5314(3) -0.07918(7) 0.60734(15) 0.0516(5) Uani 1 1 d . . .
N5 N 0.8897(3) -0.14759(7) 0.56206(16) 0.0568(5) Uani 1 1 d . . .
N6 N 0.5889(3) 0.03112(7) 0.63467(14) 0.0493(5) Uani 1 1 d . . .
H6 H 0.4668 0.0124 0.6316 0.059 Uiso 1 1 calc R . .
O1 O 0.5344(3) 0.03439(6) 0.89436(14) 0.0668(5) Uani 1 1 d . . .
O2 O 0.9630(3) 0.02120(6) 0.61961(13) 0.0647(5) Uani 1 1 d . . .
F1 F 1.0163(3) -0.19917(5) 0.79876(13) 0.0830(5) Uani 1 1 d . . .
F2 F 0.4751(3) 0.25423(5) 0.71727(13) 0.0880(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0563(16) 0.0358(12) 0.102(2) -0.0088(13) 0.0015(14) -0.0053(11)
C2 0.0665(17) 0.0322(12) 0.088(2) -0.0092(12) -0.0023(15) 0.0019(12)
C3 0.0540(15) 0.0392(12) 0.0732(18) 0.0020(12) 0.0075(13) 0.0043(11)
C4 0.0505(14) 0.0330(11) 0.0475(14) 0.0009(10) -0.0036(11) 0.0016(10)
C5 0.0497(14) 0.0336(11) 0.0519(15) 0.0021(10) -0.0016(11) -0.0014(11)
C6 0.0461(13) 0.0324(11) 0.0496(15) -0.0031(10) -0.0016(11) 0.0021(10)
C7 0.0494(14) 0.0370(12) 0.0777(19) 0.0013(12) 0.0126(13) -0.0005(11)
C8 0.0513(15) 0.0342(12) 0.093(2) 0.0011(12) 0.0022(13) -0.0024(11)
C9 0.0587(16) 0.0327(12) 0.0753(18) -0.0061(11) -0.0074(13) 0.0090(11)
C10 0.0505(14) 0.0520(15) 0.0754(19) -0.0082(13) 0.0039(13) 0.0096(12)
C11 0.0502(14) 0.0421(13) 0.0728(18) -0.0034(12) 0.0023(12) -0.0050(11)
C12 0.0511(14) 0.0396(12) 0.084(2) -0.0030(13) 0.0018(13) -0.0087(11)
C13 0.0618(17) 0.0294(11) 0.0755(19) -0.0028(11) 0.0000(14) -0.0037(11)
C14 0.0489(14) 0.0405(12) 0.0637(17) 0.0015(11) 0.0044(12) -0.0056(11)
C15 0.0464(13) 0.0325(11) 0.0462(14) 0.0015(10) 0.0020(10) -0.0051(10)
C16 0.0546(15) 0.0344(11) 0.0494(15) 0.0011(10) -0.0005(11) -0.0049(11)
C17 0.0473(13) 0.0330(11) 0.0502(15) -0.0014(10) -0.0029(11) -0.0043(10)
C18 0.0515(14) 0.0344(12) 0.0683(17) 0.0013(11) 0.0077(12) -0.0023(10)
C19 0.0584(15) 0.0300(11) 0.0803(19) 0.0048(11) -0.0025(13) -0.0068(11)
C20 0.0607(16) 0.0329(12) 0.0777(19) -0.0048(12) -0.0050(13) 0.0079(11)
C21 0.0491(14) 0.0506(15) 0.088(2) -0.0076(14) 0.0026(13) 0.0073(12)
C22 0.0465(14) 0.0423(13) 0.0771(19) -0.0021(12) -0.0006(12) -0.0081(11)
N1 0.0524(12) 0.0349(10) 0.0791(15) -0.0077(10) 0.0000(10) 0.0007(9)
N2 0.0632(14) 0.0380(11) 0.0902(17) -0.0067(11) 0.0046(12) 0.0109(10)
N3 0.0481(11) 0.0308(9) 0.0675(14) -0.0045(9) 0.0011(9) -0.0017(8)
N4 0.0472(12) 0.0357(10) 0.0719(14) -0.0059(9) 0.0031(10) -0.0044(9)
N5 0.0564(13) 0.0367(10) 0.0776(15) -0.0014(10) 0.0071(11) 0.0015(9)
N6 0.0481(11) 0.0310(9) 0.0687(14) -0.0042(9) 0.0018(10) -0.0090(8)
O1 0.0526(10) 0.0392(9) 0.1087(15) -0.0008(9) 0.0060(10) -0.0039(8)
O2 0.0552(10) 0.0398(9) 0.0994(14) -0.0047(9) 0.0058(9) -0.0107(8)
F1 0.0860(11) 0.0355(7) 0.1269(14) -0.0143(8) -0.0012(10) 0.0128(7)
F2 0.0887(11) 0.0358(7) 0.1393(15) -0.0136(9) 0.0016(10) 0.0108(7)

_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 N1 1.329(3) . ?
C1 C2 1.369(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.326(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.335(3) . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.332(3) . ?
C4 C5 1.502(3) . ?
C5 O1 1.220(2) . ?
C5 N3 1.341(3) . ?
C6 C11 1.371(3) . ?
C6 C7 1.383(3) . ?
C6 N3 1.419(2) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.349(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(3) . ?
C9 F1 1.366(2) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 N4 1.339(3) . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 N5 1.326(3) . ?
C13 H13 0.9300 . ?
C14 N5 1.332(3) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9300 . ?
C15 N4 1.328(3) . ?
C15 C16 1.504(3) . ?
C16 O2 1.219(3) . ?
C16 N6 1.346(3) . ?
C17 C22 1.374(3) . ?
C17 C18 1.383(3) . ?
C17 N6 1.417(3) . ?
C18 C19 1.385(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.349(3) . ?
C19 H19 0.9300 . ?
C20 F2 1.362(2) . ?
C20 C21 1.364(3) . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N3 H3B 0.8600 . ?
N6 H6 0.8600 . ?

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
N1 C1 C2 122.7(2) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
N2 C2 C1 122.2(2) . . ?
N2 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
N2 C3 C4 122.6(2) . . ?
N2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
N1 C4 C3 121.8(2) . . ?
N1 C4 C5 118.7(2) . . ?
C3 C4 C5 119.5(2) . . ?
O1 C5 N3 125.3(2) . . ?
O1 C5 C4 120.2(2) . . ?
N3 C5 C4 114.5(2) . . ?
C11 C6 C7 119.4(2) . . ?
C11 C6 N3 117.6(2) . . ?
C7 C6 N3 123.0(2) . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 122.5(2) . . ?
C8 C9 F1 119.2(2) . . ?
C10 C9 F1 118.3(2) . . ?
C9 C10 C11 118.3(2) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C6 C11 C10 120.6(2) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N4 C12 C13 122.4(2) . . ?
N4 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
N5 C13 C12 122.5(2) . . ?
N5 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
N5 C14 C15 122.6(2) . . ?
N5 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
N4 C15 C14 121.8(2) . . ?
N4 C15 C16 118.6(2) . . ?
C14 C15 C16 119.6(2) . . ?
O2 C16 N6 125.5(2) . . ?
O2 C16 C15 120.5(2) . . ?
N6 C16 C15 114.0(2) . . ?
C22 C17 C18 119.5(2) . . ?
C22 C17 N6 117.4(2) . . ?
C18 C17 N6 123.0(2) . . ?
C17 C18 C19 119.7(2) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 F2 119.4(2) . . ?
C19 C20 C21 122.1(2) . . ?
F2 C20 C21 118.5(2) . . ?
C20 C21 C22 118.6(2) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C17 C22 C21 120.5(2) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C1 N1 C4 115.5(2) . . ?
C2 N2 C3 115.3(2) . . ?
C5 N3 C6 128.23(19) . . ?
C5 N3 H3B 115.9 . . ?
C6 N3 H3B 115.9 . . ?
C15 N4 C12 115.4(2) . . ?
C13 N5 C14 115.3(2) . . ?
C16 N6 C17 128.22(19) . . ?
C16 N6 H6 115.9 . . ?
C17 N6 H6 115.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.2(4) . . . . ?
N2 C3 C4 N1 -0.1(4) . . . . ?
N2 C3 C4 C5 179.8(2) . . . . ?
N1 C4 C5 O1 -174.8(2) . . . . ?
C3 C4 C5 O1 5.3(3) . . . . ?
N1 C4 C5 N3 4.4(3) . . . . ?
C3 C4 C5 N3 -175.5(2) . . . . ?
C11 C6 C7 C8 -1.7(4) . . . . ?
N3 C6 C7 C8 179.4(2) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C7 C8 C9 F1 -179.6(2) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
F1 C9 C10 C11 178.8(2) . . . . ?
C7 C6 C11 C10 0.8(4) . . . . ?
N3 C6 C11 C10 179.9(2) . . . . ?
C9 C10 C11 C6 0.5(4) . . . . ?
N4 C12 C13 N5 0.2(4) . . . . ?
N5 C14 C15 N4 -0.5(4) . . . . ?
N5 C14 C15 C16 179.6(2) . . . . ?
N4 C15 C16 O2 175.9(2) . . . . ?
C14 C15 C16 O2 -4.1(3) . . . . ?
N4 C15 C16 N6 -3.8(3) . . . . ?
C14 C15 C16 N6 176.1(2) . . . . ?
C22 C17 C18 C19 0.3(3) . . . . ?
N6 C17 C18 C19 179.2(2) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 F2 178.6(2) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C22 0.6(4) . . . . ?
F2 C20 C21 C22 -178.4(2) . . . . ?
C18 C17 C22 C21 -0.2(4) . . . . ?
N6 C17 C22 C21 -179.1(2) . . . . ?
C20 C21 C22 C17 -0.3(4) . . . . ?
C2 C1 N1 C4 0.4(4) . . . . ?
C3 C4 N1 C1 -0.2(4) . . . . ?
C5 C4 N1 C1 179.9(2) . . . . ?
C1 C2 N2 C3 -0.2(4) . . . . ?
C4 C3 N2 C2 0.3(4) . . . . ?
O1 C5 N3 C6 0.7(4) . . . . ?
C4 C5 N3 C6 -178.5(2) . . . . ?
C11 C6 N3 C5 165.9(2) . . . . ?
C7 C6 N3 C5 -15.1(4) . . . . ?
C14 C15 N4 C12 0.3(3) . . . . ?
C16 C15 N4 C12 -179.7(2) . . . . ?
C13 C12 N4 C15 -0.2(4) . . . . ?
C12 C13 N5 C14 -0.3(4) . . . . ?
C15 C14 N5 C13 0.4(4) . . . . ?
O2 C16 N6 C17 -0.8(4) . . . . ?
C15 C16 N6 C17 178.9(2) . . . . ?
C22 C17 N6 C16 -168.2(2) . . . . ?
C18 C17 N6 C16 13.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.22
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 951200'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kh741

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 F1 N4 O1'
_chemical_formula_weight         218.20

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   3.7671(5)
_cell_length_b                   15.7465(19)
_cell_length_c                   16.358(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.991(11)
_cell_angle_gamma                90.00
_cell_volume                     969.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7855
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_process_details   'shape of crystal determined optically'

_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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7855
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1903
_reflns_number_gt                1206
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0340P)²+0.0379P] 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         1903
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.002
_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
C1 C 0.1620(5) 0.58572(13) 0.13543(14) 0.0561(5) Uani 1 1 d . . .
H1 H 0.0474 0.6188 0.0950 0.067 Uiso 1 1 calc R . .
C2 C 0.2343(6) 0.62065(14) 0.21181(15) 0.0623(6) Uani 1 1 d . . .
H2 H 0.1677 0.6766 0.2210 0.075 Uiso 1 1 calc R . .
C3 C 0.4820(5) 0.49786(13) 0.25469(12) 0.0550(5) Uani 1 1 d . . .
H3 H 0.5946 0.4650 0.2955 0.066 Uiso 1 1 calc R . .
C4 C 0.4130(5) 0.46212(12) 0.17884(11) 0.0446(5) Uani 1 1 d . . .
C5 C 0.5223(5) 0.37263(12) 0.16213(12) 0.0483(5) Uani 1 1 d . . .
C6 C 0.5163(4) 0.27014(11) 0.04575(11) 0.0444(5) Uani 1 1 d . . .
C7 C 0.6813(5) 0.20197(12) 0.08551(12) 0.0491(5) Uani 1 1 d . . .
H7 H 0.7600 0.2058 0.1402 0.059 Uiso 1 1 calc R . .
C8 C 0.7252(5) 0.12853(13) 0.04186(13) 0.0533(5) Uani 1 1 d . . .
H8 H 0.8335 0.0811 0.0662 0.064 Uiso 1 1 calc R . .
C9 C 0.6054(5) 0.12734(12) -0.03804(12) 0.0524(5) Uani 1 1 d . . .
C10 C 0.4469(5) 0.19689(13) -0.07403(12) 0.0535(5) Uani 1 1 d . . .
H10 H 0.3692 0.1942 -0.1289 0.064 Uiso 1 1 calc R . .
N1 N 0.2509(4) 0.50624(10) 0.11775(10) 0.0516(4) Uani 1 1 d . . .
N2 N 0.3947(5) 0.57763(11) 0.27233(11) 0.0643(5) Uani 1 1 d . . .
N3 N 0.4551(4) 0.34844(9) 0.08371(9) 0.0505(4) Uani 1 1 d . . .
H3B H 0.3603 0.3868 0.0522 0.061 Uiso 1 1 calc R . .
N4 N 0.4007(4) 0.26863(9) -0.03247(10) 0.0490(4) Uani 1 1 d . . .
O1 O 0.6608(4) 0.32760(9) 0.21564(8) 0.0707(5) Uani 1 1 d . . .
F1 F 0.6443(4) 0.05586(8) -0.08331(8) 0.0806(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0520(12) 0.0474(13) 0.0684(15) 0.0104(11) -0.0003(10) 0.0048(9)
C2 0.0631(14) 0.0467(13) 0.0776(16) -0.0046(12) 0.0089(12) 0.0015(10)
C3 0.0589(12) 0.0547(13) 0.0509(12) 0.0028(10) -0.0031(10) 0.0008(10)
C4 0.0414(10) 0.0474(11) 0.0447(11) 0.0034(9) 0.0002(8) -0.0024(8)
C5 0.0489(11) 0.0483(12) 0.0468(12) 0.0039(9) -0.0050(9) 0.0003(9)
C6 0.0426(10) 0.0457(12) 0.0445(11) 0.0045(9) -0.0008(9) -0.0012(8)
C7 0.0511(11) 0.0483(12) 0.0473(12) 0.0043(10) -0.0026(9) 0.0018(9)
C8 0.0535(12) 0.0457(12) 0.0610(14) 0.0087(10) 0.0053(10) 0.0036(9)
C9 0.0565(12) 0.0455(12) 0.0558(13) -0.0058(10) 0.0091(10) -0.0017(9)
C10 0.0586(12) 0.0559(13) 0.0452(12) -0.0011(10) -0.0032(10) -0.0034(10)
N1 0.0516(9) 0.0485(10) 0.0540(10) 0.0058(8) -0.0043(8) 0.0031(8)
N2 0.0721(12) 0.0576(12) 0.0630(12) -0.0086(10) 0.0026(10) 0.0001(9)
N3 0.0631(10) 0.0433(10) 0.0439(10) 0.0027(7) -0.0096(8) 0.0075(7)
N4 0.0554(9) 0.0475(10) 0.0434(9) 0.0025(8) -0.0052(7) 0.0002(8)
O1 0.0977(11) 0.0588(10) 0.0532(9) 0.0033(7) -0.0190(8) 0.0191(8)
F1 0.1073(10) 0.0583(8) 0.0765(9) -0.0178(7) 0.0071(7) 0.0071(7)

_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 N1 1.331(2) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.320(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.334(2) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.338(2) . ?
C4 C5 1.497(3) . ?
C5 O1 1.222(2) . ?
C5 N3 1.349(2) . ?
C6 N4 1.330(2) . ?
C6 C7 1.385(2) . ?
C6 N3 1.405(2) . ?
C7 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(3) . ?
C8 H8 0.9300 . ?
C9 F1 1.359(2) . ?
C9 C10 1.366(3) . ?
C10 N4 1.335(2) . ?
C10 H10 0.9300 . ?
N3 H3B 0.8600 . ?

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
N1 C1 C2 122.12(19) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
N2 C2 C1 122.4(2) . . ?
N2 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
N2 C3 C4 122.93(18) . . ?
N2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
N1 C4 C3 121.26(18) . . ?
N1 C4 C5 118.12(17) . . ?
C3 C4 C5 120.62(16) . . ?
O1 C5 N3 124.69(18) . . ?
O1 C5 C4 121.76(17) . . ?
N3 C5 C4 113.55(16) . . ?
N4 C6 C7 123.65(18) . . ?
N4 C6 N3 112.81(15) . . ?
C7 C6 N3 123.54(17) . . ?
C8 C7 C6 118.13(18) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C9 C8 C7 117.91(19) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
F1 C9 C8 119.67(18) . . ?
F1 C9 C10 119.09(18) . . ?
C8 C9 C10 121.24(19) . . ?
N4 C10 C9 121.66(18) . . ?
N4 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C1 N1 C4 115.85(17) . . ?
C2 N2 C3 115.44(18) . . ?
C5 N3 C6 129.86(16) . . ?
C5 N3 H3B 115.1 . . ?
C6 N3 H3B 115.1 . . ?
C6 N4 C10 117.40(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.3(3) . . . . ?
N2 C3 C4 N1 -0.2(3) . . . . ?
N2 C3 C4 C5 179.03(19) . . . . ?
N1 C4 C5 O1 -177.55(19) . . . . ?
C3 C4 C5 O1 3.2(3) . . . . ?
N1 C4 C5 N3 2.9(2) . . . . ?
C3 C4 C5 N3 -176.29(19) . . . . ?
N4 C6 C7 C8 -0.5(3) . . . . ?
N3 C6 C7 C8 179.82(18) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 F1 179.94(17) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
F1 C9 C10 N4 179.77(19) . . . . ?
C8 C9 C10 N4 -0.4(3) . . . . ?
C2 C1 N1 C4 0.4(3) . . . . ?
C3 C4 N1 C1 -0.2(3) . . . . ?
C5 C4 N1 C1 -179.40(17) . . . . ?
C1 C2 N2 C3 -0.1(3) . . . . ?
C4 C3 N2 C2 0.3(3) . . . . ?
O1 C5 N3 C6 1.2(3) . . . . ?
C4 C5 N3 C6 -179.30(17) . . . . ?
N4 C6 N3 C5 177.29(19) . . . . ?
C7 C6 N3 C5 -3.0(3) . . . . ?
C7 C6 N4 C10 0.3(3) . . . . ?
N3 C6 N4 C10 179.94(16) . . . . ?
C9 C10 N4 C6 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.027
_database_code_depnum_ccdc_archive 'CCDC 951201'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_khc188

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 I1 N4 O1'
_chemical_formula_weight         326.10

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   5.7717(3)
_cell_length_b                   24.9374(8)
_cell_length_c                   7.5654(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.819(4)
_cell_angle_gamma                90.00
_cell_volume                     1085.05(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8834
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    2.935
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_T_max  0.586
_exptl_absorpt_process_details   'shape of crystal determined optically'

_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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8834
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_sigmaI/netI    0.0847
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2130
_reflns_number_gt                1914
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0440P)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         2130
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_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
C1 C 1.005(3) -0.1016(7) 0.8576(18) 0.058(4) Uani 1 1 d . . .
H1 H 1.1423 -0.0936 0.9257 0.070 Uiso 1 1 calc R . .
C2 C 0.974(3) -0.1531(6) 0.792(2) 0.062(4) Uani 1 1 d . . .
H2 H 1.0933 -0.1780 0.8138 0.075 Uiso 1 1 calc R . .
C3 C 0.622(2) -0.1299(6) 0.6678(17) 0.055(4) Uani 1 1 d . . .
H3 H 0.4829 -0.1383 0.6030 0.066 Uiso 1 1 calc R . .
C4 C 0.658(2) -0.0781(6) 0.7287(16) 0.047(3) Uani 1 1 d . . .
C5 C 0.475(2) -0.0353(6) 0.6921(16) 0.055(4) Uani 1 1 d . . .
C6 C 0.378(2) 0.0575(6) 0.7662(16) 0.050(3) Uani 1 1 d . . .
C7 C 0.161(2) 0.0590(6) 0.6895(17) 0.056(4) Uani 1 1 d . . .
H7 H 0.0883 0.0285 0.6405 0.067 Uiso 1 1 calc R . .
C8 C 0.051(2) 0.1070(6) 0.6864(18) 0.057(4) Uani 1 1 d . . .
H8 H -0.0998 0.1095 0.6324 0.069 Uiso 1 1 calc R . .
C9 C 0.154(3) 0.1517(5) 0.7603(16) 0.048(3) Uani 1 1 d . . .
C10 C 0.379(3) 0.1452(6) 0.8355(19) 0.060(4) Uani 1 1 d . . .
H10 H 0.4555 0.1751 0.8850 0.072 Uiso 1 1 calc R . .
N1 N 0.851(2) -0.0641(5) 0.8284(14) 0.058(3) Uani 1 1 d . . .
N2 N 0.781(3) -0.1678(5) 0.6994(16) 0.068(4) Uani 1 1 d . . .
N3 N 0.517(2) 0.0108(4) 0.7792(14) 0.052(3) Uani 1 1 d . . .
H3B H 0.6405 0.0122 0.8507 0.063 Uiso 1 1 calc R . .
N4 N 0.492(2) 0.0980(5) 0.8412(14) 0.059(3) Uani 1 1 d . . .
O1 O 0.3094(18) -0.0456(4) 0.5905(12) 0.070(3) Uani 1 1 d . . .
I1 I -0.0152(2) 0.22467(4) 0.76583(14) 0.0686(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.052(10) 0.061(11) 0.060(9) 0.003(8) -0.006(7) -0.002(8)
C2 0.057(10) 0.069(11) 0.063(11) 0.026(9) 0.013(8) 0.018(9)
C3 0.052(9) 0.063(11) 0.049(8) 0.007(7) 0.003(7) 0.015(8)
C4 0.055(10) 0.048(9) 0.039(8) -0.004(6) 0.017(7) -0.005(7)
C5 0.057(11) 0.068(11) 0.039(9) 0.003(7) 0.001(8) -0.022(8)
C6 0.053(9) 0.058(10) 0.038(8) -0.002(7) -0.007(7) 0.009(7)
C7 0.040(9) 0.072(11) 0.055(9) -0.010(7) -0.001(7) 0.000(8)
C8 0.040(9) 0.071(11) 0.060(9) -0.012(8) 0.001(7) -0.001(8)
C9 0.060(10) 0.039(8) 0.046(8) -0.001(6) 0.003(7) 0.002(7)
C10 0.061(11) 0.042(9) 0.077(10) -0.009(8) 0.002(8) -0.019(8)
N1 0.048(8) 0.072(9) 0.054(7) 0.003(6) 0.001(6) -0.005(7)
N2 0.086(10) 0.054(8) 0.066(8) 0.010(6) 0.023(8) 0.018(8)
N3 0.045(7) 0.057(8) 0.052(8) 0.001(6) -0.010(6) -0.021(6)
N4 0.062(8) 0.060(9) 0.056(7) -0.014(6) 0.009(7) -0.003(7)
O1 0.060(7) 0.086(8) 0.063(6) -0.027(6) -0.004(5) -0.007(6)
I1 0.0653(6) 0.0590(6) 0.0818(7) 0.0044(8) 0.0084(4) 0.0028(8)

_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 N1 1.297(18) . ?
C1 C2 1.38(2) . ?
C1 H1 0.9300 . ?
C2 N2 1.32(2) . ?
C2 H2 0.9300 . ?
C3 N2 1.324(17) . ?
C3 C4 1.382(18) . ?
C3 H3 0.9300 . ?
C4 N1 1.337(16) . ?
C4 C5 1.511(19) . ?
C5 O1 1.205(14) . ?
C5 N3 1.336(17) . ?
C6 N4 1.308(17) . ?
C6 C7 1.339(17) . ?
C6 N3 1.410(18) . ?
C7 C8 1.353(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(19) . ?
C9 I1 2.068(13) . ?
C10 N4 1.347(18) . ?
C10 H10 0.9300 . ?
N3 H3B 0.8600 . ?

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
N1 C1 C2 123.0(15) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
N2 C2 C1 121.7(14) . . ?
N2 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
N2 C3 C4 121.7(14) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C4 C3 121.8(14) . . ?
N1 C4 C5 117.1(13) . . ?
C3 C4 C5 121.0(13) . . ?
O1 C5 N3 126.7(15) . . ?
O1 C5 C4 118.2(14) . . ?
N3 C5 C4 115.1(12) . . ?
N4 C6 C7 125.8(15) . . ?
N4 C6 N3 110.2(12) . . ?
C7 C6 N3 124.0(15) . . ?
C6 C7 C8 117.1(14) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
C7 C8 C9 121.8(14) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 116.0(13) . . ?
C8 C9 I1 122.4(11) . . ?
C10 C9 I1 121.6(10) . . ?
N4 C10 C9 123.6(13) . . ?
N4 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C1 N1 C4 115.6(13) . . ?
C2 N2 C3 116.0(13) . . ?
C5 N3 C6 126.8(13) . . ?
C5 N3 H3B 116.6 . . ?
C6 N3 H3B 116.6 . . ?
C6 N4 C10 115.8(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -2(2) . . . . ?
N2 C3 C4 N1 -3(2) . . . . ?
N2 C3 C4 C5 -179.7(11) . . . . ?
N1 C4 C5 O1 173.8(11) . . . . ?
C3 C4 C5 O1 -9.0(18) . . . . ?
N1 C4 C5 N3 -6.6(16) . . . . ?
C3 C4 C5 N3 170.7(11) . . . . ?
N4 C6 C7 C8 1(2) . . . . ?
N3 C6 C7 C8 -179.6(12) . . . . ?
C6 C7 C8 C9 -1(2) . . . . ?
C7 C8 C9 C10 1(2) . . . . ?
C7 C8 C9 I1 -177.5(10) . . . . ?
C8 C9 C10 N4 -1(2) . . . . ?
I1 C9 C10 N4 177.3(10) . . . . ?
C2 C1 N1 C4 0(2) . . . . ?
C3 C4 N1 C1 2.7(19) . . . . ?
C5 C4 N1 C1 179.9(11) . . . . ?
C1 C2 N2 C3 2(2) . . . . ?
C4 C3 N2 C2 0.0(19) . . . . ?
O1 C5 N3 C6 -2(2) . . . . ?
C4 C5 N3 C6 178.3(11) . . . . ?
N4 C6 N3 C5 -167.3(12) . . . . ?
C7 C6 N3 C5 13(2) . . . . ?
C7 C6 N4 C10 -2(2) . . . . ?
N3 C6 N4 C10 179.3(11) . . . . ?
C9 C10 N4 C6 1(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.137
_database_code_depnum_ccdc_archive 'CCDC 951202'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_new

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 I1 N3 O1'
_chemical_formula_sum            'C11 H8 I1 N3 O1'
_chemical_formula_weight         325.10

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

_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                   5.9550(8)
_cell_length_b                   7.7126(11)
_cell_length_c                   12.9998(17)
_cell_angle_alpha                78.850(11)
_cell_angle_beta                 85.640(11)
_cell_angle_gamma                70.594(11)
_cell_volume                     552.47(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    998
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      29.22

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    2.879
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.776
_exptl_absorpt_process_details   'shape of crystal determined optically'

_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 SMART 1000 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            6693
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         29.22
_reflns_number_total             2920
_reflns_number_gt                2591
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0271P)²+0.2837P] 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         2920
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.002
_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
C1 C 0.9580(6) 0.4869(5) 0.7809(2) 0.0579(8) Uani 1 1 d . . .
H1 H 0.8173 0.4738 0.8119 0.069 Uiso 1 1 calc R . .
C2 C 1.1659(6) 0.4065(5) 0.8365(2) 0.0567(7) Uani 1 1 d . . .
H2 H 1.1601 0.3417 0.9043 0.068 Uiso 1 1 calc R . .
C3 C 1.3684(5) 0.5141(4) 0.7003(2) 0.0507(6) Uani 1 1 d . . .
H3 H 1.5095 0.5268 0.6694 0.061 Uiso 1 1 calc R . .
C4 C 1.1606(5) 0.5958(4) 0.64401(19) 0.0429(5) Uani 1 1 d . . .
C5 C 1.1675(5) 0.7024(4) 0.53475(19) 0.0455(5) Uani 1 1 d . . .
C6 C 0.9020(5) 0.8740(4) 0.38453(19) 0.0440(5) Uani 1 1 d . . .
C7 C 0.6630(5) 0.9524(5) 0.3580(2) 0.0546(7) Uani 1 1 d . . .
H7 H 0.5469 0.9373 0.4077 0.066 Uiso 1 1 calc R . .
C8 C 0.5957(5) 1.0526(5) 0.2588(2) 0.0565(7) Uani 1 1 d . . .
H8 H 0.4353 1.1049 0.2419 0.068 Uiso 1 1 calc R . .
C9 C 0.7676(5) 1.0746(4) 0.1848(2) 0.0450(5) Uani 1 1 d . . .
C10 C 1.0049(5) 1.0012(4) 0.2105(2) 0.0510(6) Uani 1 1 d . . .
H10 H 1.1199 1.0191 0.1609 0.061 Uiso 1 1 calc R . .
C11 C 1.0731(5) 0.9006(4) 0.3100(2) 0.0516(6) Uani 1 1 d . . .
H11 H 1.2336 0.8509 0.3269 0.062 Uiso 1 1 calc R . .
N1 N 0.9527(4) 0.5834(4) 0.68335(18) 0.0517(6) Uani 1 1 d . . .
N2 N 1.3738(5) 0.4173(4) 0.7977(2) 0.0554(6) Uani 1 1 d . . .
N3 N 0.9554(4) 0.7685(4) 0.48568(17) 0.0496(5) Uani 1 1 d . . .
H3A H 0.8387 0.7427 0.5209 0.060 Uiso 1 1 calc R . .
O1 O 1.3526(4) 0.7231(4) 0.49748(18) 0.0637(6) Uani 1 1 d . . .
I1 I 0.66183(4) 1.21684(3) 0.033134(14) 0.05838(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0518(15) 0.080(2) 0.0386(13) 0.0117(13) -0.0039(11) -0.0287(15)
C2 0.0571(16) 0.0716(19) 0.0379(13) 0.0131(12) -0.0096(12) -0.0274(15)
C3 0.0432(13) 0.0611(16) 0.0432(13) 0.0032(12) -0.0019(11) -0.0177(12)
C4 0.0483(13) 0.0441(12) 0.0348(11) 0.0001(9) -0.0024(10) -0.0166(11)
C5 0.0500(14) 0.0482(14) 0.0345(11) 0.0019(10) -0.0014(10) -0.0160(11)
C6 0.0496(14) 0.0485(13) 0.0327(11) 0.0028(10) -0.0029(10) -0.0194(11)
C7 0.0443(14) 0.0726(19) 0.0439(13) 0.0081(13) -0.0012(11) -0.0253(13)
C8 0.0461(14) 0.0696(19) 0.0471(15) 0.0102(13) -0.0055(12) -0.0205(14)
C9 0.0557(15) 0.0456(13) 0.0333(11) 0.0025(9) -0.0047(10) -0.0202(12)
C10 0.0530(15) 0.0635(17) 0.0338(12) 0.0005(11) 0.0012(11) -0.0209(13)
C11 0.0449(14) 0.0661(17) 0.0367(12) 0.0039(12) -0.0031(10) -0.0154(13)
N1 0.0466(12) 0.0669(15) 0.0381(11) 0.0090(10) -0.0078(9) -0.0226(11)
N2 0.0508(13) 0.0658(15) 0.0439(12) 0.0072(11) -0.0109(10) -0.0186(12)
N3 0.0501(12) 0.0600(14) 0.0339(10) 0.0078(9) -0.0035(9) -0.0200(11)
O1 0.0540(12) 0.0803(15) 0.0485(11) 0.0141(11) -0.0010(9) -0.0251(11)
I1 0.06625(14) 0.06311(13) 0.03816(10) 0.01049(8) -0.01042(8) -0.01977(10)

_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 N1 1.337(3) . ?
C1 C2 1.376(4) . ?
C1 H1 0.9300 . ?
C2 N2 1.324(4) . ?
C2 H2 0.9300 . ?
C3 N2 1.336(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.330(3) . ?
C4 C5 1.502(3) . ?
C5 O1 1.217(3) . ?
C5 N3 1.354(3) . ?
C6 C11 1.389(4) . ?
C6 C7 1.390(4) . ?
C6 N3 1.404(3) . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(4) . ?
C9 I1 2.093(2) . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
N3 H3A 0.8600 . ?

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
N1 C1 C2 121.8(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
N2 C2 C1 122.9(3) . . ?
N2 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
N2 C3 C4 122.2(3) . . ?
N2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
N1 C4 C3 122.1(2) . . ?
N1 C4 C5 118.5(2) . . ?
C3 C4 C5 119.4(2) . . ?
O1 C5 N3 125.5(2) . . ?
O1 C5 C4 120.5(2) . . ?
N3 C5 C4 114.0(2) . . ?
C11 C6 C7 118.9(2) . . ?
C11 C6 N3 123.9(2) . . ?
C7 C6 N3 117.2(2) . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 I1 120.85(19) . . ?
C8 C9 I1 119.0(2) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C4 N1 C1 115.7(2) . . ?
C2 N2 C3 115.3(2) . . ?
C5 N3 C6 128.1(2) . . ?
C5 N3 H3A 116.0 . . ?
C6 N3 H3A 116.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.6(6) . . . . ?
N2 C3 C4 N1 0.0(5) . . . . ?
N2 C3 C4 C5 -179.9(3) . . . . ?
N1 C4 C5 O1 177.2(3) . . . . ?
C3 C4 C5 O1 -2.9(4) . . . . ?
N1 C4 C5 N3 -2.9(4) . . . . ?
C3 C4 C5 N3 177.0(3) . . . . ?
C11 C6 C7 C8 1.1(5) . . . . ?
N3 C6 C7 C8 -177.7(3) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C7 C8 C9 I1 177.3(3) . . . . ?
C8 C9 C10 C11 1.6(5) . . . . ?
I1 C9 C10 C11 -177.3(2) . . . . ?
C9 C10 C11 C6 -0.2(5) . . . . ?
C7 C6 C11 C10 -1.1(5) . . . . ?
N3 C6 C11 C10 177.6(3) . . . . ?
C3 C4 N1 C1 0.1(5) . . . . ?
C5 C4 N1 C1 -180.0(3) . . . . ?
C2 C1 N1 C4 0.1(5) . . . . ?
C1 C2 N2 C3 0.7(5) . . . . ?
C4 C3 N2 C2 -0.4(5) . . . . ?
O1 C5 N3 C6 -0.7(5) . . . . ?
C4 C5 N3 C6 179.4(3) . . . . ?
C11 C6 N3 C5 11.9(5) . . . . ?
C7 C6 N3 C5 -169.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        29.22
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 877918'
