# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  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. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 920810'
#TrackingRef '1.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Br2 N2'
_chemical_formula_sum            'C15 H10 Br2 N2'
_chemical_formula_weight         378.07
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'
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/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   13.8463(13)
_cell_length_b                   10.1510(11)
_cell_length_c                   10.2472(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.449(8)
_cell_angle_gamma                90.00
_cell_volume                     1439.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    5.617
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3996
_exptl_absorpt_correction_T_max  0.4485
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5277
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2529
_reflns_number_gt                1641
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0338P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         2529
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.7206(3) 0.9117(4) 0.8954(5) 0.0448(11) Uani 1 1 d . . .
H1 H 0.6922 0.8466 0.9454 0.054 Uiso 1 1 calc R . .
C2 C 0.7016(3) 0.9099(4) 0.7686(4) 0.0371(10) Uani 1 1 d . . .
C3 C 0.6388(3) 0.8095(5) 0.7076(5) 0.0447(12) Uani 1 1 d . . .
C4 C 0.6422(4) 0.6805(5) 0.7515(6) 0.0685(16) Uani 1 1 d . . .
H4 H 0.6883 0.6554 0.8143 0.082 Uiso 1 1 calc R . .
C5 C 0.5777(7) 0.5901(7) 0.7022(9) 0.116(3) Uani 1 1 d . . .
H5 H 0.5806 0.5033 0.7312 0.139 Uiso 1 1 calc R . .
C6 C 0.5103(6) 0.6255(11) 0.6123(11) 0.129(5) Uani 1 1 d . . .
H6 H 0.4653 0.5639 0.5823 0.155 Uiso 1 1 calc R . .
C7 C 0.5074(4) 0.7507(9) 0.5648(7) 0.100(2) Uani 1 1 d . . .
H7 H 0.4618 0.7742 0.5008 0.120 Uiso 1 1 calc R . .
C8 C 0.5725(3) 0.8417(5) 0.6124(5) 0.0628(15) Uani 1 1 d . . .
H8 H 0.5714 0.9269 0.5790 0.075 Uiso 1 1 calc R . .
C9 C 0.7115(3) 1.1360(5) 0.7066(5) 0.0473(12) Uani 1 1 d . . .
C10 C 0.7937(3) 0.9797(4) 0.5747(4) 0.0335(10) Uani 1 1 d . . .
C11 C 0.7983(3) 1.0671(4) 0.4709(4) 0.0470(12) Uani 1 1 d . . .
H11 H 0.7600 1.1424 0.4691 0.056 Uiso 1 1 calc R . .
C12 C 0.8601(4) 1.0415(5) 0.3702(5) 0.0530(13) Uani 1 1 d . . .
H12 H 0.8654 1.1011 0.3018 0.064 Uiso 1 1 calc R . .
C13 C 0.9134(3) 0.9285(5) 0.3713(4) 0.0451(12) Uani 1 1 d . . .
C14 C 0.9062(3) 0.8391(5) 0.4710(5) 0.0502(12) Uani 1 1 d . . .
H14 H 0.9412 0.7610 0.4695 0.060 Uiso 1 1 calc R . .
C15 C 0.8463(3) 0.8661(4) 0.5740(4) 0.0436(12) Uani 1 1 d . . .
H15 H 0.8420 0.8067 0.6427 0.052 Uiso 1 1 calc R . .
Br1 Br 0.79953(4) 1.03349(6) 0.98309(5) 0.0718(2) Uani 1 1 d . . .
Br2 Br 1.00161(4) 0.89783(7) 0.23608(5) 0.0738(2) Uani 1 1 d . . .
N1 N 0.7358(2) 1.0104(3) 0.6844(3) 0.0381(9) Uani 1 1 d . . .
N2 N 0.6906(3) 1.2426(4) 0.7229(5) 0.0721(13) 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 0.049(3) 0.045(3) 0.041(3) 0.008(2) 0.008(2) 0.000(2)
C2 0.040(2) 0.029(2) 0.043(3) 0.007(2) 0.008(2) 0.003(2)
C3 0.044(3) 0.039(3) 0.052(3) -0.008(2) 0.018(2) -0.004(2)
C4 0.090(4) 0.040(3) 0.077(4) -0.002(3) 0.039(3) -0.011(3)
C5 0.156(8) 0.059(4) 0.138(8) -0.036(6) 0.098(6) -0.052(6)
C6 0.096(6) 0.133(9) 0.161(10) -0.102(8) 0.074(6) -0.075(7)
C7 0.054(4) 0.138(7) 0.108(6) -0.068(6) 0.008(3) -0.009(5)
C8 0.045(3) 0.068(4) 0.076(4) -0.025(3) 0.003(3) -0.004(3)
C9 0.062(3) 0.037(3) 0.043(3) 0.000(3) 0.009(2) -0.007(3)
C10 0.038(2) 0.031(3) 0.031(3) 0.001(2) -0.0001(19) -0.006(2)
C11 0.064(3) 0.034(3) 0.044(3) 0.003(2) 0.008(2) 0.000(2)
C12 0.071(3) 0.055(3) 0.033(3) 0.007(2) 0.007(2) -0.009(3)
C13 0.039(2) 0.058(3) 0.038(3) -0.012(2) 0.002(2) -0.014(3)
C14 0.047(3) 0.047(3) 0.056(3) -0.007(3) 0.006(2) 0.005(2)
C15 0.048(3) 0.040(3) 0.044(3) 0.004(2) 0.008(2) 0.004(2)
Br1 0.0746(4) 0.0966(5) 0.0438(3) -0.0117(3) -0.0060(3) -0.0091(3)
Br2 0.0548(3) 0.1156(5) 0.0517(4) -0.0271(3) 0.0145(2) -0.0190(3)
N1 0.051(2) 0.030(2) 0.034(2) 0.0014(18) 0.0074(17) -0.0041(18)
N2 0.110(4) 0.035(3) 0.072(3) -0.001(3) 0.027(3) 0.000(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 C2 1.318(6) . ?
C1 Br1 1.865(4) . ?
C2 N1 1.425(5) . ?
C2 C3 1.470(6) . ?
C3 C8 1.362(6) . ?
C3 C4 1.386(6) . ?
C4 C5 1.368(9) . ?
C5 C6 1.344(12) . ?
C6 C7 1.361(11) . ?
C7 C8 1.372(8) . ?
C9 N2 1.133(5) . ?
C9 N1 1.340(6) . ?
C10 C15 1.364(5) . ?
C10 C11 1.388(6) . ?
C10 N1 1.431(5) . ?
C11 C12 1.383(6) . ?
C12 C13 1.364(6) . ?
C13 C14 1.372(6) . ?
C13 Br2 1.896(5) . ?
C14 C15 1.385(6) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 125.7(4) . . ?
C1 C2 N1 121.7(4) . . ?
C1 C2 C3 122.0(4) . . ?
N1 C2 C3 116.1(4) . . ?
C8 C3 C4 118.5(5) . . ?
C8 C3 C2 121.3(4) . . ?
C4 C3 C2 120.1(5) . . ?
C5 C4 C3 119.8(6) . . ?
C6 C5 C4 120.6(8) . . ?
C5 C6 C7 120.6(8) . . ?
C6 C7 C8 119.3(8) . . ?
C3 C8 C7 121.2(6) . . ?
N2 C9 N1 178.6(6) . . ?
C15 C10 C11 120.1(4) . . ?
C15 C10 N1 119.9(4) . . ?
C11 C10 N1 120.0(4) . . ?
C12 C11 C10 119.5(4) . . ?
C13 C12 C11 119.8(5) . . ?
C12 C13 C14 120.9(5) . . ?
C12 C13 Br2 119.4(4) . . ?
C14 C13 Br2 119.7(4) . . ?
C13 C14 C15 119.5(4) . . ?
C10 C15 C14 120.1(4) . . ?
C9 N1 C2 119.3(4) . . ?
C9 N1 C10 119.3(4) . . ?
C2 N1 C10 121.4(3) . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.079


data_120917c
_database_code_depnum_ccdc_archive 'CCDC 920811'
#TrackingRef '120917c.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Br Cl N2'
_chemical_formula_weight         333.61
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'
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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   13.4990(12)
_cell_length_b                   10.1988(9)
_cell_length_c                   10.2864(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.0190(10)
_cell_angle_gamma                90.00
_cell_volume                     1415.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      2.504
_cell_measurement_theta_max      25.568
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    3.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3722
_exptl_absorpt_correction_T_max  0.4297
_exptl_absorpt_process_details   sadabs
_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  '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            6888
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2492
_reflns_number_gt                1727
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0358P)^2^+0.3359P] where P=(Fo^2^+2Fc^2^)/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         2492
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Br1 Br 0.19079(3) 0.46566(5) 0.01790(3) 0.07471(19) Uani 1 1 d . . .
Cl1 Cl 0.00110(7) 0.61369(12) 0.75235(9) 0.0794(4) Uani 1 1 d . . .
N1 N 0.3032(3) 0.2556(3) 0.2786(3) 0.0734(9) Uani 1 1 d . . .
N2 N 0.25856(18) 0.4890(2) 0.3162(2) 0.0394(6) Uani 1 1 d . . .
C1 C 0.2820(2) 0.3632(4) 0.2943(3) 0.0480(8) Uani 1 1 d . . .
C2 C 0.2946(2) 0.5877(3) 0.2310(3) 0.0387(7) Uani 1 1 d . A .
C3 C 0.2743(2) 0.5859(3) 0.1041(3) 0.0484(8) Uani 1 1 d . . .
H3 H 0.3040 0.6496 0.0539 0.058 Uiso 1 1 calc R . .
C4 C 0.2005(2) 0.5220(3) 0.4250(3) 0.0378(7) Uani 1 1 d . . .
C5 C 0.1468(2) 0.6365(3) 0.4231(3) 0.0462(8) Uani 1 1 d . . .
H5 H 0.1506 0.6937 0.3532 0.055 Uiso 1 1 calc R . .
C6 C 0.0868(2) 0.6664(3) 0.5259(3) 0.0517(8) Uani 1 1 d . . .
H6 H 0.0509 0.7443 0.5260 0.062 Uiso 1 1 calc R . .
C7 C 0.0813(2) 0.5800(4) 0.6269(3) 0.0506(9) Uani 1 1 d . . .
C8 C 0.1353(3) 0.4664(4) 0.6306(3) 0.0575(9) Uani 1 1 d . . .
H8 H 0.1310 0.4095 0.7008 0.069 Uiso 1 1 calc R . .
C9 C 0.1960(2) 0.4369(3) 0.5300(3) 0.0490(8) Uani 1 1 d . . .
H9 H 0.2337 0.3605 0.5323 0.059 Uiso 1 1 calc R . .
C10 C 0.3601(2) 0.6886(3) 0.2920(3) 0.0446(8) Uani 1 1 d . . .
C11 C 0.422(5) 0.643(7) 0.395(7) 0.052(6) Uani 0.53(5) 1 d P A 1
H11 H 0.4151 0.5574 0.4239 0.062 Uiso 0.53(5) 1 calc PR A 1
C12 C 0.494(2) 0.724(3) 0.455(3) 0.059(5) Uani 0.53(5) 1 d P A 1
H12 H 0.5343 0.6922 0.5226 0.070 Uiso 0.53(5) 1 calc PR A 1
C13 C 0.503(2) 0.852(3) 0.412(3) 0.059(5) Uani 0.53(5) 1 d P A 1
H13 H 0.5530 0.9047 0.4483 0.070 Uiso 0.53(5) 1 calc PR A 1
C14 C 0.440(2) 0.901(2) 0.316(3) 0.057(7) Uani 0.53(5) 1 d P A 1
H14 H 0.4438 0.9888 0.2922 0.069 Uiso 0.53(5) 1 calc PR A 1
C15 C 0.370(3) 0.819(5) 0.256(4) 0.055(6) Uani 0.53(5) 1 d P A 1
H15 H 0.3288 0.8527 0.1893 0.066 Uiso 0.53(5) 1 calc PR A 1
C11' C 0.434(6) 0.668(7) 0.384(9) 0.052(10) Uani 0.47(5) 1 d P A 2
H11' H 0.4428 0.5852 0.4201 0.063 Uiso 0.47(5) 1 calc PR A 2
C12' C 0.4951(19) 0.771(3) 0.423(3) 0.057(7) Uani 0.47(5) 1 d P A 2
H12' H 0.5451 0.7581 0.4862 0.069 Uiso 0.47(5) 1 calc PR A 2
C13' C 0.4811(19) 0.892(4) 0.367(3) 0.054(6) Uani 0.47(5) 1 d P A 2
H13' H 0.5248 0.9600 0.3888 0.064 Uiso 0.47(5) 1 calc PR A 2
C14' C 0.404(3) 0.916(3) 0.278(3) 0.059(5) Uani 0.47(5) 1 d P A 2
H14' H 0.3934 1.0003 0.2453 0.071 Uiso 0.47(5) 1 calc PR A 2
C15' C 0.341(3) 0.814(6) 0.239(5) 0.050(5) Uani 0.47(5) 1 d P A 2
H15' H 0.2892 0.8274 0.1787 0.059 Uiso 0.47(5) 1 calc PR A 2
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
Br1 0.0836(3) 0.0966(4) 0.0432(2) -0.0107(2) -0.00854(18) -0.0077(2)
Cl1 0.0608(6) 0.1264(10) 0.0521(5) -0.0320(6) 0.0178(4) -0.0239(6)
N1 0.110(3) 0.044(2) 0.068(2) -0.0045(16) 0.0227(18) 0.0008(19)
N2 0.0538(16) 0.0307(16) 0.0341(14) -0.0009(10) 0.0065(11) -0.0025(11)
C1 0.061(2) 0.044(2) 0.0397(18) -0.0003(16) 0.0088(15) -0.0074(18)
C2 0.0405(17) 0.0345(17) 0.0416(18) 0.0031(14) 0.0087(13) 0.0025(14)
C3 0.0533(19) 0.049(2) 0.0429(19) 0.0061(15) 0.0072(14) 0.0000(16)
C4 0.0428(17) 0.0378(18) 0.0326(15) -0.0029(14) 0.0000(12) -0.0090(15)
C5 0.0469(18) 0.045(2) 0.0471(19) 0.0043(15) 0.0036(14) -0.0001(16)
C6 0.049(2) 0.053(2) 0.053(2) -0.0065(17) 0.0063(15) -0.0016(16)
C7 0.0456(19) 0.068(3) 0.0382(18) -0.0169(17) 0.0078(14) -0.0159(18)
C8 0.073(2) 0.065(2) 0.0348(18) 0.0028(17) 0.0073(16) -0.017(2)
C9 0.065(2) 0.042(2) 0.0400(18) 0.0049(14) 0.0027(15) -0.0015(16)
C10 0.0452(19) 0.041(2) 0.0488(19) -0.0061(16) 0.0185(15) -0.0040(16)
C11 0.043(14) 0.050(17) 0.063(14) -0.013(11) 0.004(11) -0.014(11)
C12 0.057(6) 0.049(14) 0.070(11) -0.013(8) 0.011(7) -0.016(8)
C13 0.057(9) 0.051(15) 0.068(11) -0.003(11) 0.012(8) -0.015(10)
C14 0.05(2) 0.050(10) 0.07(2) -0.004(13) 0.010(11) -0.020(14)
C15 0.059(17) 0.049(9) 0.058(11) -0.003(8) 0.017(11) -0.016(14)
C11' 0.045(18) 0.05(2) 0.063(12) -0.007(13) 0.009(10) -0.011(13)
C12' 0.055(7) 0.05(2) 0.070(12) -0.001(13) 0.009(8) -0.020(13)
C13' 0.049(16) 0.049(14) 0.064(19) -0.008(13) 0.007(11) -0.013(12)
C14' 0.055(15) 0.056(9) 0.068(13) -0.002(8) 0.009(9) -0.010(10)
C15' 0.047(14) 0.039(9) 0.064(11) -0.007(7) 0.010(10) -0.016(12)
_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 C3 1.868(3) . ?
Cl1 C7 1.747(3) . ?
N1 C1 1.146(4) . ?
N2 C1 1.342(4) . ?
N2 C4 1.429(4) . ?
N2 C2 1.431(4) . ?
C2 C3 1.324(4) . ?
C2 C10 1.481(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 C9 1.389(4) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.367(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(5) . ?
C8 C9 1.376(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11' 1.36(9) . ?
C10 C15 1.39(5) . ?
C10 C11 1.40(7) . ?
C10 C15' 1.41(5) . ?
C11 C12 1.40(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.38(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.38(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.39(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C11' C12' 1.39(7) . ?
C11' H11' 0.9300 . ?
C12' C13' 1.38(3) . ?
C12' H12' 0.9300 . ?
C13' C14' 1.38(2) . ?
C13' H13' 0.9300 . ?
C14' C15' 1.39(6) . ?
C14' H14' 0.9300 . ?
C15' H15' 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 N2 C4 119.7(2) . . ?
C1 N2 C2 118.9(2) . . ?
C4 N2 C2 121.4(2) . . ?
N1 C1 N2 178.3(4) . . ?
C3 C2 N2 122.0(3) . . ?
C3 C2 C10 121.8(3) . . ?
N2 C2 C10 116.1(3) . . ?
C2 C3 Br1 125.3(3) . . ?
C2 C3 H3 117.3 . . ?
Br1 C3 H3 117.3 . . ?
C5 C4 C9 120.3(3) . . ?
C5 C4 N2 119.6(3) . . ?
C9 C4 N2 120.1(3) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 121.6(3) . . ?
C6 C7 Cl1 119.1(3) . . ?
C8 C7 Cl1 119.3(3) . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
C11' C10 C15 105(3) . . ?
C11' C10 C11 13(4) . . ?
C15 C10 C11 117(3) . . ?
C11' C10 C15' 122(3) . . ?
C15 C10 C15' 17(2) . . ?
C11 C10 C15' 133(3) . . ?
C11' C10 C2 127(3) . . ?
C15 C10 C2 127.8(15) . . ?
C11 C10 C2 115(3) . . ?
C15' C10 C2 111.6(16) . . ?
C12 C11 C10 121(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 119(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 121(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C10 122(2) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C10 C11' C12' 120(5) . . ?
C10 C11' H11' 120.1 . . ?
C12' C11' H11' 120.1 . . ?
C13' C12' C11' 119(4) . . ?
C13' C12' H12' 120.4 . . ?
C11' C12' H12' 120.4 . . ?
C12' C13' C14' 122(3) . . ?
C12' C13' H13' 119.2 . . ?
C14' C13' H13' 119.2 . . ?
C13' C14' C15' 120(3) . . ?
C13' C14' H14' 120.2 . . ?
C15' C14' H14' 120.2 . . ?
C14' C15' C10 118(2) . . ?
C14' C15' H15' 121.1 . . ?
C10 C15' H15' 121.1 . . ?
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
C4 N2 C1 N1 -58(12) . . . . ?
C2 N2 C1 N1 120(12) . . . . ?
C1 N2 C2 C3 58.1(4) . . . . ?
C4 N2 C2 C3 -123.4(3) . . . . ?
C1 N2 C2 C10 -119.0(3) . . . . ?
C4 N2 C2 C10 59.5(3) . . . . ?
N2 C2 C3 Br1 4.4(4) . . . . ?
C10 C2 C3 Br1 -178.6(2) . . . . ?
C1 N2 C4 C5 -156.5(3) . . . . ?
C2 N2 C4 C5 25.0(4) . . . . ?
C1 N2 C4 C9 21.5(4) . . . . ?
C2 N2 C4 C9 -157.0(3) . . . . ?
C9 C4 C5 C6 -0.8(4) . . . . ?
N2 C4 C5 C6 177.2(3) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C5 C6 C7 C8 1.7(5) . . . . ?
C5 C6 C7 Cl1 -176.8(2) . . . . ?
C6 C7 C8 C9 -0.8(5) . . . . ?
Cl1 C7 C8 C9 177.8(2) . . . . ?
C7 C8 C9 C4 -0.9(5) . . . . ?
C5 C4 C9 C8 1.7(4) . . . . ?
N2 C4 C9 C8 -176.2(3) . . . . ?
C3 C2 C10 C11' -136(5) . . . . ?
N2 C2 C10 C11' 42(5) . . . . ?
C3 C2 C10 C15 34(2) . . . . ?
N2 C2 C10 C15 -149(2) . . . . ?
C3 C2 C10 C11 -143(3) . . . . ?
N2 C2 C10 C11 34(3) . . . . ?
C3 C2 C10 C15' 41(2) . . . . ?
N2 C2 C10 C15' -142(2) . . . . ?
C11' C10 C11 C12 21(26) . . . . ?
C15 C10 C11 C12 -3(8) . . . . ?
C15' C10 C11 C12 -11(9) . . . . ?
C2 C10 C11 C12 175(4) . . . . ?
C10 C11 C12 C13 0(8) . . . . ?
C11 C12 C13 C14 3(5) . . . . ?
C12 C13 C14 C15 -4(4) . . . . ?
C13 C14 C15 C10 2(5) . . . . ?
C11' C10 C15 C14 -4(6) . . . . ?
C11 C10 C15 C14 2(6) . . . . ?
C15' C10 C15 C14 162(16) . . . . ?
C2 C10 C15 C14 -175(2) . . . . ?
C15 C10 C11' C12' 2(8) . . . . ?
C11 C10 C11' C12' -156(38) . . . . ?
C15' C10 C11' C12' -3(9) . . . . ?
C2 C10 C11' C12' 174(4) . . . . ?
C10 C11' C12' C13' -1(9) . . . . ?
C11' C12' C13' C14' 4(6) . . . . ?
C12' C13' C14' C15' -4(6) . . . . ?
C13' C14' C15' C10 0(6) . . . . ?
C11' C10 C15' C14' 3(7) . . . . ?
C15 C10 C15' C14' -13(10) . . . . ?
C11 C10 C15' C14' 11(7) . . . . ?
C2 C10 C15' C14' -174(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.068