# Electronic Supplementary Material (ESI) for ChemComm.
# 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_002

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H12 Cl2 N2 O'
_chemical_formula_weight         391.24

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'
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

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

_cell_length_a                   7.7221(12)
_cell_length_b                   9.0481(13)
_cell_length_c                   13.843(2)
_cell_angle_alpha                80.021(2)
_cell_angle_beta                 85.860(2)
_cell_angle_gamma                73.874(2)
_cell_volume                     914.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2851
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.05

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7959
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4170
_reflns_number_gt                3091
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0989P)²+1.2858P] 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         4007
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.2228
_refine_ls_wR_factor_gt          0.2093
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4930(5) 0.1357(4) 0.1516(3) 0.0507(8) Uani 1 1 d . . .
H1 H 0.4063 0.0992 0.1912 0.061 Uiso 1 1 calc R . .
C2 C 0.6045(6) 0.0452(4) 0.0926(3) 0.0590(10) Uani 1 1 d . . .
H2 H 0.5934 -0.0542 0.0915 0.071 Uiso 1 1 calc R . .
C3 C 0.7373(6) 0.0983(5) 0.0327(3) 0.0623(10) Uani 1 1 d . . .
H3 H 0.8117 0.0343 -0.0081 0.075 Uiso 1 1 calc R . .
C4 C 0.7573(5) 0.2412(5) 0.0341(3) 0.0531(9) Uani 1 1 d . . .
H4 H 0.8461 0.2755 -0.0048 0.064 Uiso 1 1 calc R . .
C5 C 0.6418(4) 0.3390(4) 0.0955(2) 0.0420(7) Uani 1 1 d . . .
C6 C 0.6284(4) 0.4865(4) 0.1155(2) 0.0419(7) Uani 1 1 d . . .
C7 C 0.4845(4) 0.5216(4) 0.1866(2) 0.0425(7) Uani 1 1 d . . .
C8 C 0.4133(4) 0.3953(4) 0.2081(2) 0.0427(7) Uani 1 1 d . . .
C9 C 0.4474(5) 0.6644(4) 0.2319(3) 0.0514(9) Uani 1 1 d . . .
C10 C 0.7379(5) 0.5834(4) 0.0710(3) 0.0502(8) Uani 1 1 d . . .
C11 C 0.2658(5) 0.7425(4) 0.2688(2) 0.0442(7) Uani 1 1 d . . .
C12 C 0.1076(5) 0.7302(4) 0.2338(3) 0.0480(8) Uani 1 1 d . . .
H12 H 0.1130 0.6658 0.1875 0.058 Uiso 1 1 calc R . .
C13 C -0.0583(5) 0.8127(4) 0.2670(3) 0.0521(8) Uani 1 1 d . . .
H13 H -0.1643 0.8045 0.2434 0.062 Uiso 1 1 calc R . .
C14 C -0.0636(5) 0.9076(4) 0.3362(3) 0.0540(9) Uani 1 1 d . . .
C15 C 0.0932(5) 0.9218(5) 0.3719(3) 0.0567(9) Uani 1 1 d . . .
H15 H 0.0878 0.9862 0.4183 0.068 Uiso 1 1 calc R . .
C16 C 0.2555(5) 0.8398(4) 0.3379(3) 0.0503(8) Uani 1 1 d . . .
H16 H 0.3612 0.8491 0.3614 0.060 Uiso 1 1 calc R . .
C17 C 0.2643(5) 0.3668(4) 0.2756(3) 0.0485(8) Uani 1 1 d . . .
C18 C 0.1081(5) 0.3462(5) 0.2349(4) 0.0670(12) Uani 1 1 d . . .
H18 H 0.1039 0.3430 0.1684 0.080 Uiso 1 1 calc R . .
C19 C -0.0380(6) 0.3310(6) 0.2987(4) 0.0729(12) Uani 1 1 d . . .
H19 H -0.1413 0.3191 0.2740 0.087 Uiso 1 1 calc R . .
C20 C -0.0303(6) 0.3336(6) 0.3962(4) 0.0723(12) Uani 1 1 d . . .
H20 H -0.1302 0.3248 0.4362 0.087 Uiso 1 1 calc R . .
C21 C 0.1172(6) 0.3485(5) 0.4376(3) 0.0629(10) Uani 1 1 d . . .
H21 H 0.1197 0.3481 0.5048 0.075 Uiso 1 1 calc R . .
C22 C 0.2665(5) 0.3646(4) 0.3753(3) 0.0516(8) Uani 1 1 d . . .
Cl1 Cl 0.45206(16) 0.38543(14) 0.42777(8) 0.0701(4) Uani 1 1 d . . .
Cl2 Cl -0.27106(16) 1.01073(16) 0.38002(10) 0.0830(4) Uani 1 1 d . . .
N1 N 0.5097(4) 0.2839(3) 0.15245(19) 0.0412(6) Uani 1 1 d . . .
N2 N 0.8268(5) 0.6600(4) 0.0333(3) 0.0715(10) Uani 1 1 d . . .
O1 O 0.5724(4) 0.7208(4) 0.2370(3) 0.0876(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.348(5) . ?
C1 N1 1.385(4) . ?
C2 C3 1.408(6) . ?
C3 C4 1.348(6) . ?
C4 C5 1.419(5) . ?
C5 C6 1.384(5) . ?
C5 N1 1.392(4) . ?
C6 C10 1.418(5) . ?
C6 C7 1.435(4) . ?
C7 C8 1.379(5) . ?
C7 C9 1.482(5) . ?
C8 N1 1.390(4) . ?
C8 C17 1.480(5) . ?
C9 O1 1.222(4) . ?
C9 C11 1.482(5) . ?
C10 N2 1.145(5) . ?
C11 C12 1.385(5) . ?
C11 C16 1.393(5) . ?
C12 C13 1.383(5) . ?
C13 C14 1.384(5) . ?
C14 C15 1.386(6) . ?
C14 Cl2 1.741(4) . ?
C15 C16 1.364(5) . ?
C17 C22 1.378(5) . ?
C17 C18 1.437(6) . ?
C18 C19 1.404(6) . ?
C19 C20 1.359(7) . ?
C20 C21 1.361(6) . ?
C21 C22 1.415(6) . ?
C22 Cl1 1.721(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 119.0(4) . . ?
C1 C2 C3 121.3(4) . . ?
C4 C3 C2 120.4(4) . . ?
C3 C4 C5 119.5(4) . . ?
C6 C5 N1 107.3(3) . . ?
C6 C5 C4 134.1(3) . . ?
N1 C5 C4 118.6(3) . . ?
C5 C6 C10 124.8(3) . . ?
C5 C6 C7 107.7(3) . . ?
C10 C6 C7 127.5(3) . . ?
C8 C7 C6 107.8(3) . . ?
C8 C7 C9 130.5(3) . . ?
C6 C7 C9 121.3(3) . . ?
C7 C8 N1 107.5(3) . . ?
C7 C8 C17 131.4(3) . . ?
N1 C8 C17 121.1(3) . . ?
O1 C9 C7 117.9(3) . . ?
O1 C9 C11 119.3(3) . . ?
C7 C9 C11 122.9(3) . . ?
N2 C10 C6 178.5(4) . . ?
C12 C11 C16 119.0(3) . . ?
C12 C11 C9 123.2(3) . . ?
C16 C11 C9 117.7(3) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C14 118.8(3) . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 Cl2 119.6(3) . . ?
C15 C14 Cl2 119.1(3) . . ?
C16 C15 C14 118.9(3) . . ?
C15 C16 C11 121.3(4) . . ?
C22 C17 C18 118.7(4) . . ?
C22 C17 C8 122.7(3) . . ?
C18 C17 C8 118.5(3) . . ?
C19 C18 C17 118.0(5) . . ?
C20 C19 C18 120.8(4) . . ?
C19 C20 C21 122.8(4) . . ?
C20 C21 C22 117.8(4) . . ?
C17 C22 C21 121.8(4) . . ?
C17 C22 Cl1 120.4(3) . . ?
C21 C22 Cl1 117.7(3) . . ?
C1 N1 C8 129.0(3) . . ?
C1 N1 C5 121.2(3) . . ?
C8 N1 C5 109.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         1.441
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 978204'
#######################################################################
#
#                 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_0002

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 Br Cl N3 O'
_chemical_formula_weight         478.76

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_hall_group_name_H-M    'P 2ac 2ab '

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

_cell_length_a                   10.2750(12)
_cell_length_b                   11.4634(14)
_cell_length_c                   18.344(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2160.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7538
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      22.48

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    2.047
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18822
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3799
_reflns_number_gt                2864
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1157P)²+2.6536P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.99(2)
_refine_ls_number_reflns         3795
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.2067
_refine_ls_wR_factor_gt          0.1905
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.07465(9) 0.64626(9) 0.23396(5) 0.0793(4) Uani 1 1 d . . .
Cl1 Cl 0.3897(4) 0.7223(3) 0.60731(19) 0.1152(11) Uani 1 1 d . . .
N1 N 0.2222(5) 0.1081(5) 0.3928(3) 0.0471(14) Uani 1 1 d . . .
C24 C 0.1686(8) 0.0203(8) 0.5784(4) 0.060(2) Uani 1 1 d . . .
C22 C 0.3670(8) 0.5074(7) 0.5503(4) 0.062(2) Uani 1 1 d . . .
H22 H 0.4540 0.5150 0.5370 0.074 Uiso 1 1 calc R . .
C18 C 0.1724(6) 0.3931(7) 0.5558(4) 0.0493(17) Uani 1 1 d . . .
C23 C 0.3003(7) 0.4077(7) 0.5347(4) 0.0516(18) Uani 1 1 d . . .
H23 H 0.3419 0.3482 0.5092 0.062 Uiso 1 1 calc R . .
C4 C 0.1759(7) 0.2142(7) 0.4212(4) 0.0526(18) Uani 1 1 d . . .
N2 N 0.3624(8) -0.2218(6) 0.3433(4) 0.0668(18) Uani 1 1 d . . .
C12 C 0.2493(7) 0.3615(8) 0.3305(4) 0.0575(18) Uani 1 1 d . . .
H12 H 0.3299 0.3248 0.3282 0.069 Uiso 1 1 calc R . .
C11 C 0.1539(7) 0.3174(7) 0.3762(4) 0.0522(18) Uani 1 1 d . . .
C9 C 0.4172(9) -0.2459(8) 0.2717(5) 0.078(2) Uani 1 1 d . . .
H9A H 0.3485 -0.2483 0.2362 0.117 Uiso 1 1 calc R . .
H9B H 0.4612 -0.3198 0.2726 0.117 Uiso 1 1 calc R . .
H9C H 0.4779 -0.1856 0.2590 0.117 Uiso 1 1 calc R . .
C16 C 0.0350(7) 0.3741(8) 0.3785(4) 0.061(2) Uani 1 1 d . . .
H16 H -0.0303 0.3455 0.4087 0.073 Uiso 1 1 calc R . .
C5 C 0.2557(7) 0.0789(7) 0.3223(4) 0.0529(18) Uani 1 1 d . . .
H5 H 0.2491 0.1342 0.2854 0.063 Uiso 1 1 calc R . .
O1 O 0.0097(6) 0.2582(7) 0.5856(4) 0.090(2) Uani 1 1 d . . .
N3 N 0.1596(9) -0.0284(8) 0.6325(4) 0.086(2) Uani 1 1 d . . .
C1 C 0.2269(7) 0.0241(7) 0.4468(4) 0.0512(18) Uani 1 1 d . . .
C7 C 0.3105(7) -0.1166(7) 0.3605(4) 0.0516(18) Uani 1 1 d . . .
C17 C 0.1032(7) 0.2825(8) 0.5474(4) 0.057(2) Uani 1 1 d . . .
C3 C 0.1510(7) 0.1964(7) 0.4937(4) 0.0510(18) Uani 1 1 d . . .
C13 C 0.2264(7) 0.4589(7) 0.2883(4) 0.0590(19) Uani 1 1 d . . .
H13 H 0.2911 0.4879 0.2578 0.071 Uiso 1 1 calc R . .
C6 C 0.2975(7) -0.0283(7) 0.3070(4) 0.0531(18) Uani 1 1 d . . .
H6 H 0.3191 -0.0459 0.2590 0.064 Uiso 1 1 calc R . .
C2 C 0.1806(7) 0.0777(7) 0.5101(4) 0.0542(19) Uani 1 1 d . . .
C21 C 0.3038(9) 0.5969(8) 0.5860(4) 0.068(2) Uani 1 1 d . . .
C8 C 0.2717(7) -0.0872(7) 0.4310(4) 0.0509(17) Uani 1 1 d . . .
H8 H 0.2760 -0.1429 0.4678 0.061 Uiso 1 1 calc R . .
C14 C 0.1063(7) 0.5128(7) 0.2918(4) 0.0578(19) Uani 1 1 d . . .
C19 C 0.1107(9) 0.4851(9) 0.5904(5) 0.072(2) Uani 1 1 d . . .
H19 H 0.0239 0.4777 0.6041 0.087 Uiso 1 1 calc R . .
C15 C 0.0112(8) 0.4722(8) 0.3369(5) 0.064(2) Uani 1 1 d . . .
H15 H -0.0687 0.5101 0.3396 0.077 Uiso 1 1 calc R . .
C10 C 0.3695(12) -0.3123(9) 0.3975(6) 0.083(3) Uani 1 1 d . . .
H10A H 0.4245 -0.2874 0.4368 0.124 Uiso 1 1 calc R . .
H10B H 0.4048 -0.3818 0.3760 0.124 Uiso 1 1 calc R . .
H10C H 0.2838 -0.3283 0.4159 0.124 Uiso 1 1 calc R . .
C20 C 0.1760(10) 0.5872(9) 0.6047(5) 0.079(3) Uani 1 1 d . . .
H20 H 0.1332 0.6491 0.6270 0.095 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.890(8) . ?
Cl1 C21 1.731(10) . ?
N1 C1 1.382(10) . ?
N1 C5 1.380(9) . ?
N1 C4 1.406(10) . ?
C24 N3 1.142(11) . ?
C24 C2 1.420(11) . ?
C22 C23 1.363(11) . ?
C22 C21 1.380(12) . ?
C22 H22 0.9300 . ?
C18 C23 1.381(10) . ?
C18 C19 1.384(11) . ?
C18 C17 1.461(12) . ?
C23 H23 0.9300 . ?
C4 C3 1.370(11) . ?
C4 C11 1.460(11) . ?
N2 C7 1.357(11) . ?
N2 C10 1.438(12) . ?
N2 C9 1.457(11) . ?
C12 C13 1.378(12) . ?
C12 C11 1.386(11) . ?
C12 H12 0.9300 . ?
C11 C16 1.384(11) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C16 C15 1.381(12) . ?
C16 H16 0.9300 . ?
C5 C6 1.331(11) . ?
C5 H5 0.9300 . ?
O1 C17 1.222(9) . ?
C1 C8 1.388(11) . ?
C1 C2 1.397(10) . ?
C7 C8 1.394(10) . ?
C7 C6 1.416(11) . ?
C17 C3 1.478(11) . ?
C3 C2 1.428(12) . ?
C13 C14 1.382(11) . ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?
C21 C20 1.362(14) . ?
C8 H8 0.9300 . ?
C14 C15 1.362(11) . ?
C19 C20 1.374(14) . ?
C19 H19 0.9300 . ?
C15 H15 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 119.6(6) . . ?
C1 N1 C4 110.4(6) . . ?
C5 N1 C4 129.8(6) . . ?
N3 C24 C2 178.3(10) . . ?
C23 C22 C21 119.1(8) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C23 C18 C19 118.2(8) . . ?
C23 C18 C17 122.6(7) . . ?
C19 C18 C17 119.1(7) . . ?
C22 C23 C18 121.4(7) . . ?
C22 C23 H23 119.3 . . ?
C18 C23 H23 119.3 . . ?
C3 C4 N1 107.1(7) . . ?
C3 C4 C11 129.8(7) . . ?
N1 C4 C11 123.0(6) . . ?
C7 N2 C10 120.1(7) . . ?
C7 N2 C9 122.0(7) . . ?
C10 N2 C9 117.9(8) . . ?
C13 C12 C11 121.0(7) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C11 C16 118.1(7) . . ?
C12 C11 C4 121.8(7) . . ?
C16 C11 C4 120.0(7) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C16 C11 121.4(7) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C6 C5 N1 120.1(7) . . ?
C6 C5 H5 119.9 . . ?
N1 C5 H5 119.9 . . ?
N1 C1 C8 120.1(6) . . ?
N1 C1 C2 106.2(7) . . ?
C8 C1 C2 133.7(7) . . ?
N2 C7 C8 122.8(7) . . ?
N2 C7 C6 120.8(7) . . ?
C8 C7 C6 116.3(7) . . ?
O1 C17 C18 121.3(7) . . ?
O1 C17 C3 119.4(8) . . ?
C18 C17 C3 119.2(6) . . ?
C4 C3 C2 107.9(7) . . ?
C4 C3 C17 127.6(8) . . ?
C2 C3 C17 124.5(7) . . ?
C12 C13 C14 119.2(7) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C5 C6 C7 122.9(7) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C1 C2 C24 124.0(8) . . ?
C1 C2 C3 108.4(7) . . ?
C24 C2 C3 127.6(7) . . ?
C20 C21 C22 120.8(9) . . ?
C20 C21 Cl1 120.2(7) . . ?
C22 C21 Cl1 119.0(7) . . ?
C1 C8 C7 120.7(7) . . ?
C1 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C15 C14 C13 121.1(7) . . ?
C15 C14 Br1 119.6(6) . . ?
C13 C14 Br1 119.3(6) . . ?
C20 C19 C18 120.9(8) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C14 C15 C16 119.1(7) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C21 C20 C19 119.5(8) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 978827'
#######################################################################
#
#                 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_001

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H17 Cl N2 O'
_chemical_formula_weight         420.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   10.4826(16)
_cell_length_b                   10.6458(17)
_cell_length_c                   10.9600(15)
_cell_angle_alpha                71.680(5)
_cell_angle_beta                 73.572(4)
_cell_angle_gamma                67.431(5)
_cell_volume                     1053.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4444
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.29

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16987
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0746
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4861
_reflns_number_gt                2714
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0493P)²+0.2216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0088(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4815
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
C15 C 0.6547(2) 0.1443(2) 0.78818(19) 0.0435(5) Uani 1 1 d . . .
H15 H 0.5669 0.2083 0.7752 0.052 Uiso 1 1 calc R . .
C16 C 0.6862(2) 0.0947(2) 0.9121(2) 0.0507(6) Uani 1 1 d . . .
H16 H 0.6211 0.1269 0.9823 0.061 Uiso 1 1 calc R . .
Cl1 Cl 0.85296(8) -0.06926(8) 1.08713(6) 0.0832(3) Uani 1 1 d . . .
C19 C 0.8835(2) 0.0028(2) 0.7035(2) 0.0445(5) Uani 1 1 d . . .
H19 H 0.9508 -0.0266 0.6331 0.053 Uiso 1 1 calc R . .
O1 O 0.81923(14) 0.16820(16) 0.45360(14) 0.0563(4) Uani 1 1 d . . .
C22 C 0.6905(2) 0.5650(2) 0.2382(2) 0.0471(6) Uani 1 1 d . . .
H22 H 0.7241 0.6264 0.2541 0.056 Uiso 1 1 calc R . .
C7 C 0.1414(2) 0.2137(2) 0.4997(2) 0.0484(6) Uani 1 1 d . . .
H7 H 0.0658 0.1836 0.5100 0.058 Uiso 1 1 calc R . .
C8 C 0.2428(2) 0.1363(2) 0.57003(19) 0.0435(5) Uani 1 1 d . . .
H8 H 0.2340 0.0567 0.6338 0.052 Uiso 1 1 calc R . .
C27 C 0.5099(2) -0.0108(2) 0.69891(19) 0.0410(5) Uani 1 1 d . . .
N2 N 0.5282(2) -0.1131(2) 0.77769(18) 0.0582(5) Uani 1 1 d . . .
C5 C 0.2653(2) 0.3858(2) 0.38589(18) 0.0393(5) Uani 1 1 d . . .
C3 C 0.51561(19) 0.2957(2) 0.43160(18) 0.0340(5) Uani 1 1 d . . .
C13 C 0.7248(2) 0.1543(2) 0.54645(19) 0.0381(5) Uani 1 1 d . . .
C14 C 0.75351(19) 0.0991(2) 0.68250(18) 0.0361(5) Uani 1 1 d . . .
C17 C 0.8146(2) -0.0026(2) 0.9303(2) 0.0507(6) Uani 1 1 d . . .
C18 C 0.9138(2) -0.0497(2) 0.8275(2) 0.0514(6) Uani 1 1 d . . .
H18 H 1.0003 -0.1162 0.8417 0.062 Uiso 1 1 calc R . .
C20 C 0.57821(19) 0.3890(2) 0.32206(18) 0.0363(5) Uani 1 1 d . . .
C21 C 0.63039(19) 0.4803(2) 0.3424(2) 0.0403(5) Uani 1 1 d . . .
H21 H 0.6249 0.4847 0.4273 0.048 Uiso 1 1 calc R . .
C24 C 0.6504(3) 0.4688(3) 0.0912(2) 0.0667(7) Uani 1 1 d . . .
H24 H 0.6568 0.4642 0.0063 0.080 Uiso 1 1 calc R . .
C9 C 0.0353(2) 0.4325(3) 0.3475(2) 0.0602(7) Uani 1 1 d . . .
H9 H -0.0420 0.4044 0.3589 0.072 Uiso 1 1 calc R . .
C10 C 0.0362(3) 0.5615(3) 0.2710(3) 0.0669(7) Uani 1 1 d . . .
H10 H -0.0391 0.6197 0.2296 0.080 Uiso 1 1 calc R . .
C11 C 0.1487(3) 0.6051(3) 0.2555(2) 0.0643(7) Uani 1 1 d . . .
H11 H 0.1474 0.6942 0.2058 0.077 Uiso 1 1 calc R . .
C12 C 0.2634(2) 0.5182(2) 0.3127(2) 0.0507(6) Uani 1 1 d . . .
H12 H 0.3389 0.5485 0.3020 0.061 Uiso 1 1 calc R . .
N1 N 0.38006(16) 0.29107(16) 0.44782(14) 0.0356(4) Uani 1 1 d . . .
C2 C 0.57930(19) 0.1899(2) 0.52807(18) 0.0354(5) Uani 1 1 d . . .
C23 C 0.7020(2) 0.5610(2) 0.1110(2) 0.0540(6) Uani 1 1 d . . .
C25 C 0.5898(3) 0.3838(3) 0.1943(2) 0.0590(7) Uani 1 1 d . . .
H25 H 0.5564 0.3224 0.1782 0.071 Uiso 1 1 calc R . .
C26 C 0.7669(3) 0.6545(3) -0.0033(3) 0.0885(10) Uani 1 1 d . . .
H26A H 0.7256 0.7491 0.0065 0.133 Uiso 1 1 calc R . .
H26B H 0.7500 0.6495 -0.0830 0.133 Uiso 1 1 calc R . .
H26C H 0.8663 0.6242 -0.0060 0.133 Uiso 1 1 calc R . .
C6 C 0.1486(2) 0.3421(2) 0.4088(2) 0.0446(5) Uani 1 1 d . . .
C4 C 0.3638(2) 0.1760(2) 0.54697(17) 0.0364(5) Uani 1 1 d . . .
C1 C 0.4848(2) 0.1147(2) 0.60040(18) 0.0364(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C15 C16 1.379(3) . ?
C15 C14 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(3) . ?
C16 H16 0.9300 . ?
Cl1 C17 1.739(2) . ?
C19 C18 1.375(3) . ?
C19 C14 1.384(3) . ?
C19 H19 0.9300 . ?
O1 C13 1.218(2) . ?
C22 C21 1.377(3) . ?
C22 C23 1.378(3) . ?
C22 H22 0.9300 . ?
C7 C8 1.340(3) . ?
C7 C6 1.431(3) . ?
C7 H7 0.9300 . ?
C8 C4 1.419(3) . ?
C8 H8 0.9300 . ?
C27 N2 1.144(2) . ?
C27 C1 1.416(3) . ?
C5 C12 1.381(3) . ?
C5 C6 1.402(3) . ?
C5 N1 1.423(2) . ?
C3 C2 1.381(3) . ?
C3 N1 1.400(2) . ?
C3 C20 1.471(3) . ?
C13 C2 1.481(3) . ?
C13 C14 1.492(3) . ?
C17 C18 1.377(3) . ?
C18 H18 0.9300 . ?
C20 C21 1.382(3) . ?
C20 C25 1.387(3) . ?
C21 H21 0.9300 . ?
C24 C25 1.375(3) . ?
C24 C23 1.382(3) . ?
C24 H24 0.9300 . ?
C9 C10 1.368(3) . ?
C9 C6 1.399(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 C4 1.389(2) . ?
C2 C1 1.420(3) . ?
C23 C26 1.508(3) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C4 C1 1.386(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C22 C23 121.6(2) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C4 119.77(19) . . ?
C7 C8 H8 120.1 . . ?
C4 C8 H8 120.1 . . ?
N2 C27 C1 178.5(2) . . ?
C12 C5 C6 120.66(19) . . ?
C12 C5 N1 122.39(18) . . ?
C6 C5 N1 116.84(17) . . ?
C2 C3 N1 107.28(16) . . ?
C2 C3 C20 128.16(17) . . ?
N1 C3 C20 124.28(16) . . ?
O1 C13 C2 121.36(18) . . ?
O1 C13 C14 120.58(18) . . ?
C2 C13 C14 118.06(17) . . ?
C19 C14 C15 119.14(18) . . ?
C19 C14 C13 118.97(18) . . ?
C15 C14 C13 121.87(18) . . ?
C16 C17 C18 121.5(2) . . ?
C16 C17 Cl1 119.33(19) . . ?
C18 C17 Cl1 119.13(18) . . ?
C19 C18 C17 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C21 C20 C25 118.21(18) . . ?
C21 C20 C3 121.72(17) . . ?
C25 C20 C3 120.04(18) . . ?
C22 C21 C20 120.60(19) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C25 C24 C23 121.5(2) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C10 C9 C6 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C6 C9 H9 119.5 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C5 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C5 C12 H12 120.2 . . ?
C4 N1 C3 109.11(15) . . ?
C4 N1 C5 120.37(16) . . ?
C3 N1 C5 130.41(16) . . ?
C3 C2 C1 108.08(17) . . ?
C3 C2 C13 125.88(17) . . ?
C1 C2 C13 125.89(17) . . ?
C22 C23 C24 117.5(2) . . ?
C22 C23 C26 121.7(2) . . ?
C24 C23 C26 120.8(2) . . ?
C24 C25 C20 120.5(2) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C9 C6 C5 117.9(2) . . ?
C9 C6 C7 121.0(2) . . ?
C5 C6 C7 120.91(18) . . ?
C1 C4 N1 107.53(16) . . ?
C1 C4 C8 132.17(19) . . ?
N1 C4 C8 120.13(17) . . ?
C4 C1 C27 123.58(18) . . ?
C4 C1 C2 107.76(17) . . ?
C27 C1 C2 128.23(18) . . ?

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
C14 C15 C16 C17 -1.8(3) . . . . ?
C6 C7 C8 C4 -5.0(3) . . . . ?
C18 C19 C14 C15 1.3(3) . . . . ?
C18 C19 C14 C13 179.65(19) . . . . ?
C16 C15 C14 C19 0.5(3) . . . . ?
C16 C15 C14 C13 -177.83(19) . . . . ?
O1 C13 C14 C19 -32.0(3) . . . . ?
C2 C13 C14 C19 147.30(19) . . . . ?
O1 C13 C14 C15 146.3(2) . . . . ?
C2 C13 C14 C15 -34.4(3) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
C15 C16 C17 Cl1 -178.16(17) . . . . ?
C14 C19 C18 C17 -1.7(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
Cl1 C17 C18 C19 179.91(17) . . . . ?
C2 C3 C20 C21 -62.6(3) . . . . ?
N1 C3 C20 C21 124.3(2) . . . . ?
C2 C3 C20 C25 115.5(2) . . . . ?
N1 C3 C20 C25 -57.6(3) . . . . ?
C23 C22 C21 C20 -0.6(3) . . . . ?
C25 C20 C21 C22 0.8(3) . . . . ?
C3 C20 C21 C22 178.97(18) . . . . ?
C6 C9 C10 C11 -1.2(4) . . . . ?
C9 C10 C11 C12 2.2(4) . . . . ?
C10 C11 C12 C5 0.3(4) . . . . ?
C6 C5 C12 C11 -3.7(3) . . . . ?
N1 C5 C12 C11 -179.8(2) . . . . ?
C2 C3 N1 C4 -4.8(2) . . . . ?
C20 C3 N1 C4 169.58(17) . . . . ?
C2 C3 N1 C5 171.38(18) . . . . ?
C20 C3 N1 C5 -14.2(3) . . . . ?
C12 C5 N1 C4 162.87(19) . . . . ?
C6 C5 N1 C4 -13.4(3) . . . . ?
C12 C5 N1 C3 -12.9(3) . . . . ?
C6 C5 N1 C3 170.80(19) . . . . ?
N1 C3 C2 C1 3.0(2) . . . . ?
C20 C3 C2 C1 -171.13(18) . . . . ?
N1 C3 C2 C13 178.69(18) . . . . ?
C20 C3 C2 C13 4.6(3) . . . . ?
O1 C13 C2 C3 -33.4(3) . . . . ?
C14 C13 C2 C3 147.27(19) . . . . ?
O1 C13 C2 C1 141.6(2) . . . . ?
C14 C13 C2 C1 -37.7(3) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C21 C22 C23 C26 179.5(2) . . . . ?
C25 C24 C23 C22 -0.1(4) . . . . ?
C25 C24 C23 C26 -179.4(2) . . . . ?
C23 C24 C25 C20 0.3(4) . . . . ?
C21 C20 C25 C24 -0.7(3) . . . . ?
C3 C20 C25 C24 -178.9(2) . . . . ?
C10 C9 C6 C5 -2.2(4) . . . . ?
C10 C9 C6 C7 173.3(2) . . . . ?
C12 C5 C6 C9 4.6(3) . . . . ?
N1 C5 C6 C9 -179.06(19) . . . . ?
C12 C5 C6 C7 -170.8(2) . . . . ?
N1 C5 C6 C7 5.5(3) . . . . ?
C8 C7 C6 C9 -171.7(2) . . . . ?
C8 C7 C6 C5 3.6(3) . . . . ?
C3 N1 C4 C1 4.8(2) . . . . ?
C5 N1 C4 C1 -171.87(16) . . . . ?
C3 N1 C4 C8 -170.96(17) . . . . ?
C5 N1 C4 C8 12.4(3) . . . . ?
C7 C8 C4 C1 -177.4(2) . . . . ?
C7 C8 C4 N1 -2.9(3) . . . . ?
N1 C4 C1 C27 -175.90(17) . . . . ?
C8 C4 C1 C27 -0.9(3) . . . . ?
N1 C4 C1 C2 -2.9(2) . . . . ?
C8 C4 C1 C2 172.1(2) . . . . ?
N2 C27 C1 C4 24(10) . . . . ?
N2 C27 C1 C2 -148(10) . . . . ?
C3 C2 C1 C4 -0.1(2) . . . . ?
C13 C2 C1 C4 -175.81(18) . . . . ?
C3 C2 C1 C27 172.54(19) . . . . ?
C13 C2 C1 C27 -3.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 970814'
#######################################################################
#
#                 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_0509

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 Cl N2 O'
_chemical_formula_weight         356.79

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           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   23.071(3)
_cell_length_b                   10.7768(13)
_cell_length_c                   14.3886(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.951(4)
_cell_angle_gamma                90.00
_cell_volume                     3486.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5829
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.32

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23001
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4013
_reflns_number_gt                2215
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1059P)²+4.5018P] 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         4022
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2268
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.71995(16) 0.6729(3) 0.7682(3) 0.0617(10) Uani 1 1 d . . .
H1 H 0.7401 0.5975 0.7779 0.074 Uiso 1 1 calc R . .
C2 C 0.71736(18) 0.7384(4) 0.6867(3) 0.0704(11) Uani 1 1 d . . .
H2 H 0.7355 0.7073 0.6400 0.084 Uiso 1 1 calc R . .
C3 C 0.68740(17) 0.8532(3) 0.6725(3) 0.0612(9) Uani 1 1 d . . .
H3 H 0.6862 0.8976 0.6167 0.073 Uiso 1 1 calc R . .
C4 C 0.66061(15) 0.8989(3) 0.7386(2) 0.0539(8) Uani 1 1 d . . .
H4 H 0.6407 0.9745 0.7286 0.065 Uiso 1 1 calc R . .
C5 C 0.66272(11) 0.8336(2) 0.82145(18) 0.0297(6) Uani 1 1 d . . .
C6 C 0.63791(14) 0.8634(3) 0.8979(2) 0.0452(7) Uani 1 1 d . . .
C7 C 0.65053(13) 0.7682(3) 0.9630(2) 0.0445(7) Uani 1 1 d . . .
C8 C 0.68376(14) 0.6773(3) 0.9255(2) 0.0461(7) Uani 1 1 d . . .
C9 C 0.63404(14) 0.7704(3) 1.0559(2) 0.0487(8) Uani 1 1 d . . .
C10 C 0.61484(14) 0.6563(3) 1.0981(2) 0.0466(7) Uani 1 1 d . . .
C11 C 0.58877(15) 0.5579(3) 1.0431(2) 0.0551(9) Uani 1 1 d . . .
H11 H 0.5847 0.5598 0.9773 0.066 Uiso 1 1 calc R . .
C12 C 0.56868(18) 0.4563(3) 1.0854(3) 0.0668(10) Uani 1 1 d . . .
H12 H 0.5511 0.3904 1.0478 0.080 Uiso 1 1 calc R . .
C13 C 0.57441(19) 0.4519(3) 1.1818(3) 0.0720(11) Uani 1 1 d . . .
H13 H 0.5606 0.3835 1.2099 0.086 Uiso 1 1 calc R . .
C14 C 0.6007(2) 0.5491(4) 1.2371(3) 0.0800(13) Uani 1 1 d . . .
H14 H 0.6053 0.5459 1.3029 0.096 Uiso 1 1 calc R . .
C15 C 0.62036(18) 0.6509(3) 1.1960(3) 0.0640(10) Uani 1 1 d . . .
H15 H 0.6375 0.7168 1.2340 0.077 Uiso 1 1 calc R . .
C16 C 0.60260(15) 0.9778(3) 0.8974(2) 0.0476(8) Uani 1 1 d . . .
C17 C 0.63087(17) 1.0934(3) 0.9076(3) 0.0595(9) Uani 1 1 d . . .
H17 H 0.6720 1.0975 0.9157 0.071 Uiso 1 1 calc R . .
C18 C 0.54121(15) 0.9759(3) 0.8854(2) 0.0551(9) Uani 1 1 d . . .
C19 C 0.5985(2) 1.2012(3) 0.9059(3) 0.0720(11) Uani 1 1 d . . .
H19 H 0.6179 1.2774 0.9143 0.086 Uiso 1 1 calc R . .
C20 C 0.50876(18) 1.0840(4) 0.8815(3) 0.0719(11) Uani 1 1 d . . .
H20 H 0.4676 1.0813 0.8719 0.086 Uiso 1 1 calc R . .
C21 C 0.5382(2) 1.1965(4) 0.8919(3) 0.0762(12) Uani 1 1 d . . .
H21 H 0.5167 1.2697 0.8893 0.091 Uiso 1 1 calc R . .
C22 C 0.70684(16) 0.5632(3) 0.9658(3) 0.0577(9) Uani 1 1 d . . .
Cl1 Cl 0.50414(5) 0.83558(11) 0.87562(8) 0.0827(4) Uani 1 1 d . . .
N1 N 0.69174(14) 0.7205(3) 0.8380(2) 0.0675(9) Uani 1 1 d . . .
N2 N 0.72444(17) 0.4694(3) 0.9950(3) 0.0885(12) Uani 1 1 d . . .
O1 O 0.63530(13) 0.8695(2) 1.09841(17) 0.0673(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.358(5) . ?
C1 N1 1.410(4) . ?
C2 C3 1.410(5) . ?
C3 C4 1.339(5) . ?
C4 C5 1.376(4) . ?
C5 N1 1.384(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.376(4) . ?
C6 C16 1.476(4) . ?
C7 C8 1.423(4) . ?
C7 C9 1.469(4) . ?
C8 N1 1.393(4) . ?
C8 C22 1.412(5) . ?
C9 O1 1.229(4) . ?
C9 C10 1.482(4) . ?
C10 C11 1.379(5) . ?
C10 C15 1.387(5) . ?
C11 C12 1.382(5) . ?
C12 C13 1.364(6) . ?
C13 C14 1.371(6) . ?
C14 C15 1.370(5) . ?
C16 C18 1.388(5) . ?
C16 C17 1.398(5) . ?
C17 C19 1.378(5) . ?
C18 C20 1.380(5) . ?
C18 Cl1 1.727(4) . ?
C19 C21 1.361(6) . ?
C20 C21 1.381(6) . ?
C22 N2 1.134(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 119.1(3) . . ?
C1 C2 C3 120.5(3) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 119.6(3) . . ?
C4 C5 N1 121.4(3) . . ?
C4 C5 C6 128.9(3) . . ?
N1 C5 C6 109.7(2) . . ?
C7 C6 C5 107.7(3) . . ?
C7 C6 C16 131.2(3) . . ?
C5 C6 C16 121.0(3) . . ?
C6 C7 C8 107.8(3) . . ?
C6 C7 C9 123.3(3) . . ?
C8 C7 C9 128.9(3) . . ?
N1 C8 C22 123.3(3) . . ?
N1 C8 C7 107.7(3) . . ?
C22 C8 C7 129.0(3) . . ?
O1 C9 C7 119.0(3) . . ?
O1 C9 C10 119.5(3) . . ?
C7 C9 C10 121.5(3) . . ?
C11 C10 C15 118.6(3) . . ?
C11 C10 C9 122.4(3) . . ?
C15 C10 C9 118.9(3) . . ?
C10 C11 C12 120.2(3) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C14 119.4(3) . . ?
C15 C14 C13 120.5(4) . . ?
C14 C15 C10 120.5(3) . . ?
C18 C16 C17 117.7(3) . . ?
C18 C16 C6 122.3(3) . . ?
C17 C16 C6 120.0(3) . . ?
C19 C17 C16 120.8(4) . . ?
C20 C18 C16 121.4(3) . . ?
C20 C18 Cl1 118.8(3) . . ?
C16 C18 Cl1 119.8(3) . . ?
C21 C19 C17 120.1(4) . . ?
C18 C20 C21 119.2(4) . . ?
C19 C21 C20 120.8(4) . . ?
N2 C22 C8 177.4(5) . . ?
C5 N1 C8 107.0(3) . . ?
C5 N1 C1 118.8(3) . . ?
C8 N1 C1 134.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 939543'
#######################################################################
#
#                 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_0509

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H12 Br Cl N2 O'
_chemical_formula_sum            'C22 H12 Br Cl N2 O'
_chemical_formula_weight         435.69

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7273(16)
_cell_length_b                   8.9408(18)
_cell_length_c                   14.824(3)
_cell_angle_alpha                76.526(6)
_cell_angle_beta                 80.859(6)
_cell_angle_gamma                70.826(6)
_cell_volume                     936.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.30

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8463
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3220
_reflns_number_gt                2134
_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)+(0.0636P)²+1.6047P] 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         3220
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.88205(9) 0.03003(12) 0.11414(6) 0.1183(4) Uani 1 1 d . . .
Cl2 Cl 0.7907(2) 0.6475(3) 0.05344(12) 0.1169(8) Uani 1 1 d . . .
C1 C 0.0077(5) 0.7227(4) 0.3572(2) 0.0278(8) Uani 1 1 d . . .
C19 C 0.6438(7) 0.1206(7) 0.1710(4) 0.0660(15) Uani 1 1 d . . .
C22 C -0.2235(6) 0.4185(6) 0.4332(3) 0.0501(12) Uani 1 1 d . . .
C14 C 0.1170(6) 0.6116(5) 0.3047(3) 0.0440(11) Uani 1 1 d . . .
C7 C 0.0469(6) 0.4820(5) 0.3247(3) 0.0427(10) Uani 1 1 d . . .
C9 C 0.2830(7) 0.6354(6) 0.1473(3) 0.0523(12) Uani 1 1 d . . .
H9 H 0.1825 0.6272 0.1238 0.063 Uiso 1 1 calc R . .
C6 C -0.1098(6) 0.5165(5) 0.3900(3) 0.0434(10) Uani 1 1 d . . .
C8 C 0.2734(6) 0.6415(5) 0.2404(3) 0.0438(10) Uani 1 1 d . . .
C16 C 0.2962(6) 0.2598(5) 0.2480(3) 0.0471(11) Uani 1 1 d . . .
C10 C 0.4396(7) 0.6411(6) 0.0887(3) 0.0587(13) Uani 1 1 d . . .
H10 H 0.4450 0.6369 0.0262 0.070 Uiso 1 1 calc R . .
C20 C 0.6248(7) 0.2050(6) 0.2398(4) 0.0602(13) Uani 1 1 d . . .
H20 H 0.7274 0.2157 0.2599 0.072 Uiso 1 1 calc R . .
C5 C -0.2606(7) 0.7621(6) 0.4693(3) 0.0562(13) Uani 1 1 d . . .
H5 H -0.3549 0.7264 0.5051 0.067 Uiso 1 1 calc R . .
C4 C -0.2434(7) 0.9058(6) 0.4724(4) 0.0658(15) Uani 1 1 d . . .
H4 H -0.3248 0.9688 0.5122 0.079 Uiso 1 1 calc R . .
C11 C 0.5874(7) 0.6532(7) 0.1242(4) 0.0647(14) Uani 1 1 d . . .
C15 C 0.1044(7) 0.3337(6) 0.2859(3) 0.0525(12) Uani 1 1 d . . .
C21 C 0.4495(6) 0.2745(5) 0.2788(3) 0.0500(12) Uani 1 1 d . . .
H21 H 0.4344 0.3315 0.3260 0.060 Uiso 1 1 calc R . .
C2 C 0.0181(7) 0.8725(6) 0.3594(4) 0.0556(13) Uani 1 1 d . . .
H2 H 0.1085 0.9114 0.3218 0.067 Uiso 1 1 calc R . .
C18 C 0.4942(8) 0.1005(7) 0.1409(4) 0.0698(16) Uani 1 1 d . . .
H18 H 0.5107 0.0406 0.0949 0.084 Uiso 1 1 calc R . .
C12 C 0.5785(7) 0.6682(7) 0.2146(4) 0.0648(15) Uani 1 1 d . . .
H12 H 0.6771 0.6824 0.2367 0.078 Uiso 1 1 calc R . .
C3 C -0.1035(7) 0.9622(6) 0.4164(4) 0.0625(14) Uani 1 1 d . . .
H3 H -0.0954 1.0626 0.4189 0.075 Uiso 1 1 calc R . .
C13 C 0.4215(7) 0.6622(6) 0.2728(3) 0.0546(12) Uani 1 1 d . . .
H13 H 0.4148 0.6722 0.3344 0.065 Uiso 1 1 calc R . .
C17 C 0.3201(7) 0.1701(6) 0.1797(3) 0.0586(13) Uani 1 1 d . . .
H17 H 0.2185 0.1570 0.1600 0.070 Uiso 1 1 calc R . .
N1 N -0.1316(6) 0.6670(5) 0.4101(3) 0.0672(12) Uani 1 1 d . . .
N2 N -0.3186(6) 0.3427(5) 0.4700(3) 0.0693(13) Uani 1 1 d . . .
O1 O -0.0108(5) 0.2679(5) 0.2861(3) 0.0887(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C19 1.898(5) . ?
Cl2 C11 1.737(5) . ?
C1 C2 1.376(6) . ?
C1 C14 1.381(6) . ?
C1 N1 1.387(6) . ?
C19 C20 1.367(7) . ?
C19 C18 1.381(8) . ?
C22 N2 1.151(6) . ?
C22 C6 1.420(7) . ?
C14 C7 1.388(6) . ?
C14 C8 1.472(6) . ?
C7 C6 1.422(6) . ?
C7 C15 1.473(6) . ?
C9 C10 1.381(6) . ?
C9 C8 1.384(6) . ?
C9 H9 0.9300 . ?
C6 N1 1.395(6) . ?
C8 C13 1.389(6) . ?
C16 C17 1.388(6) . ?
C16 C21 1.389(6) . ?
C16 C15 1.488(6) . ?
C10 C11 1.375(7) . ?
C10 H10 0.9300 . ?
C20 C21 1.386(6) . ?
C20 H20 0.9300 . ?
C5 C4 1.346(7) . ?
C5 N1 1.414(6) . ?
C5 H5 0.9300 . ?
C4 C3 1.411(8) . ?
C4 H4 0.9300 . ?
C11 C12 1.367(7) . ?
C15 O1 1.217(5) . ?
C21 H21 0.9300 . ?
C2 C3 1.345(7) . ?
C2 H2 0.9300 . ?
C18 C17 1.378(7) . ?
C18 H18 0.9300 . ?
C12 C13 1.382(7) . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C17 H17 0.9300 . ?

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 C14 129.1(4) . . ?
C2 C1 N1 120.5(4) . . ?
C14 C1 N1 110.3(4) . . ?
C20 C19 C18 121.9(5) . . ?
C20 C19 Br1 119.2(4) . . ?
C18 C19 Br1 118.9(4) . . ?
N2 C22 C6 177.7(5) . . ?
C1 C14 C7 107.2(4) . . ?
C1 C14 C8 121.8(4) . . ?
C7 C14 C8 131.0(4) . . ?
C14 C7 C6 108.0(4) . . ?
C14 C7 C15 130.4(4) . . ?
C6 C7 C15 121.5(4) . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
N1 C6 C22 123.7(4) . . ?
N1 C6 C7 107.5(4) . . ?
C22 C6 C7 128.7(4) . . ?
C9 C8 C13 118.4(4) . . ?
C9 C8 C14 120.2(4) . . ?
C13 C8 C14 121.1(4) . . ?
C17 C16 C21 119.4(4) . . ?
C17 C16 C15 117.3(4) . . ?
C21 C16 C15 123.3(4) . . ?
C11 C10 C9 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C19 C20 C21 118.6(5) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C4 C5 N1 118.2(5) . . ?
C4 C5 H5 120.9 . . ?
N1 C5 H5 120.9 . . ?
C5 C4 C3 121.0(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 Cl2 119.0(4) . . ?
C10 C11 Cl2 119.6(4) . . ?
O1 C15 C7 118.1(4) . . ?
O1 C15 C16 118.7(4) . . ?
C7 C15 C16 123.3(4) . . ?
C20 C21 C16 120.7(4) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C17 C18 C19 119.3(5) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C11 C12 C13 119.3(5) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C2 C3 C4 120.8(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C12 C13 C8 120.8(5) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C18 C17 C16 120.1(5) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C1 N1 C6 106.9(4) . . ?
C1 N1 C5 119.9(4) . . ?
C6 N1 C5 133.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 939542'
