# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_ax0260
_database_code_depnum_ccdc_archive 'CCDC 1062102'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
2,6-Dichloro-3,5-diphenylpyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 Cl2 N'
_chemical_formula_weight         300.17

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   21.3422(5)
_cell_length_b                   8.1975(2)
_cell_length_c                   8.0145(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1402.16(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9591
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      28.69

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15714
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0095
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.99
_reflns_number_total             1692
_reflns_number_gt                1599
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        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 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)+(0.0336P)²+0.5927P] 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         1692
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.45236(5) 1.04439(12) 0.31255(13) 0.0182(2) Uani 1 1 d . . .
C2 C 0.44808(4) 0.87457(13) 0.31494(12) 0.0175(2) Uani 1 1 d . . .
C3 C 0.5000 0.79258(18) 0.2500 0.0188(3) Uani 1 2 d S . .
H3 H 0.5000 0.6767 0.2500 0.023 Uiso 1 2 calc SR . .
C4 C 0.39389(5) 0.78056(14) 0.37983(13) 0.0196(2) Uani 1 1 d . . .
C5 C 0.40379(6) 0.65538(14) 0.49440(15) 0.0248(2) Uani 1 1 d . . .
H5 H 0.4449 0.6336 0.5338 0.030 Uiso 1 1 calc R . .
C6 C 0.35379(6) 0.56225(15) 0.55135(16) 0.0317(3) Uani 1 1 d . . .
H6 H 0.3607 0.4783 0.6309 0.038 Uiso 1 1 calc R . .
C7 C 0.29381(6) 0.59167(16) 0.49224(17) 0.0336(3) Uani 1 1 d . . .
H7 H 0.2597 0.5271 0.5304 0.040 Uiso 1 1 calc R . .
C8 C 0.28350(5) 0.71530(17) 0.37751(17) 0.0321(3) Uani 1 1 d . . .
H8 H 0.2424 0.7350 0.3368 0.039 Uiso 1 1 calc R . .
C9 C 0.33315(5) 0.81058(14) 0.32187(15) 0.0248(2) Uani 1 1 d . . .
H9 H 0.3258 0.8962 0.2444 0.030 Uiso 1 1 calc R . .
Cl1 Cl 0.393882(12) 1.16480(3) 0.39987(4) 0.02523(10) Uani 1 1 d . . .
N1 N 0.5000 1.12815(16) 0.2500 0.0196(2) Uani 1 2 d S . .

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 0.0159(4) 0.0215(5) 0.0172(4) -0.0013(4) -0.0019(4) 0.0030(4)
C2 0.0139(4) 0.0216(5) 0.0171(4) 0.0001(4) -0.0018(4) -0.0005(4)
C3 0.0160(6) 0.0188(6) 0.0215(7) 0.000 -0.0012(5) 0.000
C4 0.0162(5) 0.0213(5) 0.0213(5) -0.0046(4) 0.0030(4) -0.0021(4)
C5 0.0254(5) 0.0235(5) 0.0256(5) -0.0018(4) 0.0017(4) -0.0026(4)
C6 0.0403(7) 0.0235(5) 0.0312(6) -0.0019(5) 0.0106(5) -0.0075(5)
C7 0.0289(6) 0.0304(6) 0.0416(7) -0.0137(6) 0.0175(5) -0.0126(5)
C8 0.0166(5) 0.0372(7) 0.0426(7) -0.0142(6) 0.0072(5) -0.0041(5)
C9 0.0168(5) 0.0288(5) 0.0289(5) -0.0050(5) 0.0021(4) 0.0001(4)
Cl1 0.02188(15) 0.02555(16) 0.02826(16) -0.00302(10) 0.00385(9) 0.00624(9)
N1 0.0189(6) 0.0202(6) 0.0195(6) 0.000 -0.0020(5) 0.000

_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 1.3253(12) . ?
C1 C2 1.3952(15) . ?
C1 Cl1 1.7383(10) . ?
C2 C3 1.3967(12) . ?
C2 C4 1.4838(14) . ?
C3 C2 1.3967(12) 3_655 ?
C3 H3 0.9500 . ?
C4 C5 1.3931(16) . ?
C4 C9 1.3987(15) . ?
C5 C6 1.3892(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3861(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3900(16) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
N1 C1 1.3254(12) 3_655 ?

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 124.92(10) . . ?
N1 C1 Cl1 114.13(8) . . ?
C2 C1 Cl1 120.93(8) . . ?
C1 C2 C3 115.02(10) . . ?
C1 C2 C4 125.04(9) . . ?
C3 C2 C4 119.94(10) . . ?
C2 C3 C2 122.47(13) . 3_655 ?
C2 C3 H3 118.8 . . ?
C2 C3 H3 118.8 3_655 . ?
C5 C4 C9 119.28(10) . . ?
C5 C4 C2 119.69(9) . . ?
C9 C4 C2 120.96(10) . . ?
C6 C5 C4 120.32(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.10(12) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 120.03(11) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.18(11) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C4 120.08(12) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
C1 N1 C1 117.59(13) . 3_655 ?

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 C3 2.17(14) . . . . ?
Cl1 C1 C2 C3 -176.16(6) . . . . ?
N1 C1 C2 C4 -177.88(8) . . . . ?
Cl1 C1 C2 C4 3.79(14) . . . . ?
C1 C2 C3 C2 -0.97(6) . . . 3_655 ?
C4 C2 C3 C2 179.07(10) . . . 3_655 ?
C1 C2 C4 C5 -129.21(12) . . . . ?
C3 C2 C4 C5 50.74(13) . . . . ?
C1 C2 C4 C9 53.79(15) . . . . ?
C3 C2 C4 C9 -126.25(10) . . . . ?
C9 C4 C5 C6 -0.48(17) . . . . ?
C2 C4 C5 C6 -177.53(10) . . . . ?
C4 C5 C6 C7 1.08(18) . . . . ?
C5 C6 C7 C8 -0.70(19) . . . . ?
C6 C7 C8 C9 -0.27(18) . . . . ?
C7 C8 C9 C4 0.87(18) . . . . ?
C5 C4 C9 C8 -0.49(17) . . . . ?
C2 C4 C9 C8 176.52(10) . . . . ?
C2 C1 N1 C1 -1.17(7) . . . 3_655 ?
Cl1 C1 N1 C1 177.26(8) . . . 3_655 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ax0229
_database_code_depnum_ccdc_archive 'CCDC 1062103'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3-Bromo-2,6-dichloro-5-(4-tolyl)pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Br Cl2 N'
_chemical_formula_weight         317.00

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                   14.5770(3)
_cell_length_b                   10.7855(3)
_cell_length_c                   7.6172(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2980(10)
_cell_angle_gamma                90.00
_cell_volume                     1170.10(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.77

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    3.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23134
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         28.79
_reflns_number_total             3049
_reflns_number_gt                2737
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        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 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)+(0.0281P)²+0.6513P] 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         3049
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.004
_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 0.527567(11) 1.228649(16) 1.00012(2) 0.02164(6) Uani 1 1 d . . .
C1 C 0.35365(12) 1.32180(16) 0.7890(2) 0.0205(3) Uani 1 1 d . . .
C2 C 0.40431(11) 1.21853(15) 0.8625(2) 0.0181(3) Uani 1 1 d . . .
C3 C 0.36078(11) 1.10398(15) 0.8364(2) 0.0181(3) Uani 1 1 d . . .
H3 H 0.3940 1.0318 0.8852 0.022 Uiso 1 1 calc R . .
C4 C 0.26831(11) 1.09342(15) 0.7387(2) 0.0176(3) Uani 1 1 d . . .
C5 C 0.22662(11) 1.20416(16) 0.6683(2) 0.0191(3) Uani 1 1 d . . .
C6 C 0.22313(11) 0.96907(15) 0.7213(2) 0.0175(3) Uani 1 1 d . . .
C7 C 0.13578(11) 0.95030(16) 0.7645(2) 0.0216(3) Uani 1 1 d . . .
H7 H 0.1014 1.0189 0.7950 0.026 Uiso 1 1 calc R . .
C8 C 0.09922(11) 0.83164(17) 0.7628(2) 0.0231(3) Uani 1 1 d . . .
H8 H 0.0397 0.8201 0.7922 0.028 Uiso 1 1 calc R . .
C9 C 0.14771(12) 0.72907(16) 0.7191(2) 0.0218(3) Uani 1 1 d . . .
C10 C 0.23427(12) 0.74846(16) 0.6733(2) 0.0217(3) Uani 1 1 d . . .
H10 H 0.2681 0.6800 0.6408 0.026 Uiso 1 1 calc R . .
C11 C 0.27137(11) 0.86744(16) 0.6750(2) 0.0202(3) Uani 1 1 d . . .
H11 H 0.3305 0.8793 0.6440 0.024 Uiso 1 1 calc R . .
C12 C 0.10849(13) 0.59992(18) 0.7248(3) 0.0298(4) Uani 1 1 d . . .
H12A H 0.0530 0.5902 0.6274 0.045 Uiso 1 1 calc R . .
H12B H 0.0909 0.5867 0.8405 0.045 Uiso 1 1 calc R . .
H12C H 0.1562 0.5390 0.7102 0.045 Uiso 1 1 calc R . .
Cl1 Cl 0.40226(3) 1.46876(4) 0.81883(7) 0.02979(10) Uani 1 1 d . . .
Cl2 Cl 0.11418(3) 1.20423(4) 0.53198(6) 0.02612(10) Uani 1 1 d . . .
N1 N 0.26690(10) 1.31487(13) 0.69158(19) 0.0214(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
Br1 0.01890(9) 0.02371(9) 0.02102(9) 0.00045(6) 0.00137(6) -0.00351(6)
C1 0.0244(8) 0.0184(7) 0.0198(7) -0.0004(6) 0.0072(6) 0.0001(6)
C2 0.0164(7) 0.0221(8) 0.0157(7) 0.0009(6) 0.0033(6) -0.0003(6)
C3 0.0178(7) 0.0191(7) 0.0172(7) 0.0007(6) 0.0031(6) 0.0019(6)
C4 0.0161(7) 0.0220(8) 0.0153(7) -0.0003(6) 0.0043(5) -0.0003(6)
C5 0.0164(7) 0.0250(8) 0.0160(7) 0.0001(6) 0.0033(6) 0.0027(6)
C6 0.0156(7) 0.0204(7) 0.0153(7) 0.0013(6) 0.0008(5) -0.0007(6)
C7 0.0178(7) 0.0260(8) 0.0209(8) 0.0000(7) 0.0040(6) 0.0019(6)
C8 0.0173(7) 0.0316(9) 0.0204(8) 0.0021(7) 0.0037(6) -0.0034(7)
C9 0.0223(8) 0.0256(8) 0.0153(7) 0.0026(6) -0.0010(6) -0.0055(7)
C10 0.0221(8) 0.0207(8) 0.0214(8) -0.0011(6) 0.0023(6) 0.0014(6)
C11 0.0167(7) 0.0242(8) 0.0197(8) -0.0006(6) 0.0039(6) -0.0009(6)
C12 0.0326(10) 0.0273(9) 0.0284(9) 0.0026(7) 0.0037(7) -0.0098(8)
Cl1 0.0342(2) 0.01585(18) 0.0377(2) -0.00067(17) 0.00409(18) -0.00247(16)
Cl2 0.01901(19) 0.0312(2) 0.0254(2) 0.00367(17) -0.00140(15) 0.00510(16)
N1 0.0236(7) 0.0207(7) 0.0201(7) 0.0016(6) 0.0052(5) 0.0033(6)

_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 C2 1.8805(16) . ?
C1 N1 1.325(2) . ?
C1 C2 1.387(2) . ?
C1 Cl1 1.7313(17) . ?
C2 C3 1.384(2) . ?
C3 C4 1.399(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(2) . ?
C4 C6 1.488(2) . ?
C5 N1 1.326(2) . ?
C5 Cl2 1.7433(16) . ?
C6 C11 1.388(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.385(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(2) . ?
C9 C12 1.510(2) . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 122.92(15) . . ?
N1 C1 Cl1 116.11(13) . . ?
C2 C1 Cl1 120.96(13) . . ?
C3 C2 C1 118.06(15) . . ?
C3 C2 Br1 119.11(12) . . ?
C1 C2 Br1 122.81(13) . . ?
C2 C3 C4 120.65(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 115.25(15) . . ?
C5 C4 C6 126.11(14) . . ?
C3 C4 C6 118.63(14) . . ?
N1 C5 C4 125.14(15) . . ?
N1 C5 Cl2 114.37(12) . . ?
C4 C5 Cl2 120.46(13) . . ?
C11 C6 C7 118.84(15) . . ?
C11 C6 C4 119.75(14) . . ?
C7 C6 C4 121.22(14) . . ?
C8 C7 C6 120.01(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 121.52(15) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C10 118.27(15) . . ?
C8 C9 C12 120.80(16) . . ?
C10 C9 C12 120.92(16) . . ?
C11 C10 C9 120.44(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C6 C11 C10 120.91(15) . . ?
C6 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C5 117.93(14) . . ?

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 C3 -1.8(2) . . . . ?
Cl1 C1 C2 C3 178.90(12) . . . . ?
N1 C1 C2 Br1 179.78(12) . . . . ?
Cl1 C1 C2 Br1 0.5(2) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
Br1 C2 C3 C4 178.33(12) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C2 C3 C4 C6 -177.27(14) . . . . ?
C3 C4 C5 N1 -1.9(2) . . . . ?
C6 C4 C5 N1 177.10(15) . . . . ?
C3 C4 C5 Cl2 176.05(11) . . . . ?
C6 C4 C5 Cl2 -4.9(2) . . . . ?
C5 C4 C6 C11 134.20(17) . . . . ?
C3 C4 C6 C11 -46.8(2) . . . . ?
C5 C4 C6 C7 -51.0(2) . . . . ?
C3 C4 C6 C7 128.01(17) . . . . ?
C11 C6 C7 C8 0.8(2) . . . . ?
C4 C6 C7 C8 -174.09(15) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C7 C8 C9 C12 177.65(16) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C12 C9 C10 C11 -177.60(16) . . . . ?
C7 C6 C11 C10 -0.7(2) . . . . ?
C4 C6 C11 C10 174.22(15) . . . . ?
C9 C10 C11 C6 -0.3(3) . . . . ?
C2 C1 N1 C5 1.8(2) . . . . ?
Cl1 C1 N1 C5 -178.87(12) . . . . ?
C4 C5 N1 C1 0.1(2) . . . . ?
Cl2 C5 N1 C1 -177.94(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.79
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.064

#=====================  End of ax0229 =================================

#=====================  End of CIF submission =================================

