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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
#TrackingRef '12gyte78_12gyte78_CHirel.cif'

_chemical_name_systematic        ?
_chemical_name_common            1,1,3-trichloro-1H-isoindole
_chemical_formula_moiety         'C8 H4 Cl3 N '
_chemical_formula_sum            'C8 H4 Cl3 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         220.47

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.9288(3)
_cell_length_b                   6.9261(2)
_cell_length_c                   7.8324(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     864.11(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3568
_cell_measurement_theta_min      2.5573
_cell_measurement_theta_max      27.4827
_cell_measurement_temperature    170.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440

_exptl_absorpt_coefficient_mu    0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.85

_exptl_special_details           
;
;

_diffrn_ambient_temperature      170.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4573
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_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.
;

_reflns_number_total             834
_reflns_number_gt                798
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0623
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_refine_ls_number_reflns         834
_refine_ls_number_parameters     70
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+0.3110P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.353
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.46107(12) 0.25 0.0210(3) 0.0198(4) Uani d S 1 . .
C C2 0.54028(13) 0.25 -0.0524(3) 0.0239(5) Uani d S 1 . .
H H2 0.5476 0.25 -0.1728 0.029 Uiso calc SR 1 . .
C C3 0.60839(13) 0.25 0.0578(3) 0.0287(5) Uani d S 1 . .
H H3 0.6636 0.25 0.0121 0.034 Uiso calc SR 1 . .
C C4 0.59737(14) 0.25 0.2340(3) 0.0310(5) Uani d S 1 . .
H H4 0.6453 0.25 0.3062 0.037 Uiso calc SR 1 . .
C C5 0.51753(14) 0.25 0.3069(3) 0.0271(5) Uani d S 1 . .
H H5 0.51 0.25 0.4272 0.033 Uiso calc SR 1 . .
C C6 0.45003(12) 0.25 0.1967(3) 0.0202(4) Uani d S 1 . .
C C7 0.35646(12) 0.25 0.2264(3) 0.0208(4) Uani d S 1 . .
C C8 0.37599(13) 0.25 -0.0500(3) 0.0206(4) Uani d S 1 . .
Cl Cl1 0.32265(2) 0.04078(6) 0.34040(5) 0.02707(16) Uani d . 1 . .
Cl Cl2 0.35851(3) 0.25 -0.26481(6) 0.02851(18) Uani d S 1 . .
N N1 0.31576(10) 0.25 0.0580(2) 0.0227(4) Uani d S 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0202(10) 0.0150(9) 0.0242(10) 0 0.0005(8) 0
C2 0.0246(10) 0.0188(10) 0.0283(11) 0 0.0068(9) 0
C3 0.0175(10) 0.0249(11) 0.0435(14) 0 0.0046(9) 0
C4 0.0202(10) 0.0310(12) 0.0418(14) 0 -0.0060(10) 0
C5 0.0241(11) 0.0297(12) 0.0276(11) 0 -0.0040(9) 0
C6 0.0192(10) 0.0181(10) 0.0234(10) 0 0.0015(8) 0
C7 0.0190(10) 0.0235(11) 0.0199(10) 0 0.0016(8) 0
C8 0.0232(10) 0.0173(10) 0.0214(10) 0 -0.0013(8) 0
Cl1 0.0274(2) 0.0265(2) 0.0273(3) -0.00375(14) 0.00501(14) 0.00320(15)
Cl2 0.0315(3) 0.0347(3) 0.0193(3) 0 -0.0015(2) 0
N1 0.0190(9) 0.0273(10) 0.0220(9) 0 -0.0010(7) 0

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.386(3) ?
C1 C6 . 1.388(3) ?
C1 C8 . 1.465(3) ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.391(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.394(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.379(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.508(3) ?
C7 N1 . 1.469(3) ?
C7 Cl1 7_565 1.7853(12) ?
C7 Cl1 . 1.7853(12) ?
C8 N1 . 1.279(3) ?
C8 Cl2 . 1.706(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.76(19) ?
C2 C1 C8 . . 133.23(19) ?
C6 C1 C8 . . 105.00(17) ?
C3 C2 C1 . . 117.0(2) ?
C3 C2 H2 . . 121.5 ?
C1 C2 H2 . . 121.5 ?
C2 C3 C4 . . 121.24(19) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C3 C4 C5 . . 121.4(2) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C6 C5 C4 . . 117.1(2) ?
C6 C5 H5 . . 121.5 ?
C4 C5 H5 . . 121.5 ?
C5 C6 C1 . . 121.46(19) ?
C5 C6 C7 . . 132.38(19) ?
C1 C6 C7 . . 106.15(17) ?
N1 C7 C6 . . 107.32(16) ?
N1 C7 Cl1 . 7_565 108.40(8) ?
C6 C7 Cl1 . 7_565 112.04(9) ?
N1 C7 Cl1 . . 108.40(8) ?
C6 C7 Cl1 . . 112.04(9) ?
Cl1 C7 Cl1 7_565 . 108.52(11) ?
N1 C8 C1 . . 116.31(18) ?
N1 C8 Cl2 . . 122.01(16) ?
C1 C8 Cl2 . . 121.68(15) ?
C8 N1 C7 . . 105.22(16) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0 ?
C8 C1 C2 C3 . . . . 180.0 ?
C1 C2 C3 C4 . . . . 0 ?
C2 C3 C4 C5 . . . . 0 ?
C3 C4 C5 C6 . . . . 0 ?
C4 C5 C6 C1 . . . . 0 ?
C4 C5 C6 C7 . . . . 180.0 ?
C2 C1 C6 C5 . . . . 0 ?
C8 C1 C6 C5 . . . . 180.0 ?
C2 C1 C6 C7 . . . . 180.0 ?
C8 C1 C6 C7 . . . . 0 ?
C5 C6 C7 N1 . . . . 180.0 ?
C1 C6 C7 N1 . . . . 0 ?
C5 C6 C7 Cl1 . . . 7_565 61.12(10) ?
C1 C6 C7 Cl1 . . . 7_565 -118.88(10) ?
C5 C6 C7 Cl1 . . . . -61.12(10) ?
C1 C6 C7 Cl1 . . . . 118.88(10) ?
C2 C1 C8 N1 . . . . 180.0 ?
C6 C1 C8 N1 . . . . 0 ?
C2 C1 C8 Cl2 . . . . 0 ?
C6 C1 C8 Cl2 . . . . 180.0 ?
C1 C8 N1 C7 . . . . 0 ?
Cl2 C8 N1 C7 . . . . 180.0 ?
C6 C7 N1 C8 . . . . 0 ?
Cl1 C7 N1 C8 7_565 . . . 121.19(8) ?
Cl1 C7 N1 C8 . . . . -121.19(8) ?
_iucr_refine_instructions_details 
;
TITL 12gyte78 in Pnma
CELL 0.71073 15.9288 6.9261 7.8324 90.000 90.000 90.000
ZERR 4.00 0.0003 0.0002 0.0002 0.000 0.000 0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, 0.5-Z
SFAC C H N Cl
UNIT 32 16 4 12
L.S. 15
ACTA
BOND $H
FMAP 2
PLAN 10
CONF
SIZE 0.175 0.198 0.239
HTAB
TEMP -103.140
WGHT 0.034600 0.311000
FVAR 0.22064
MOLE 1
C1 1 0.461074 0.250000 0.020962 10.50000 0.02023 0.01502 =
0.02415 0.00000 0.00049 0.00000
C2 1 0.540284 0.250000 -0.052379 10.50000 0.02460 0.01878 =
0.02828 0.00000 0.00678 0.00000
AFIX 43
H2 2 0.547560 0.250000 -0.172764 10.50000 -1.20000
AFIX 0
C3 1 0.608390 0.250000 0.057763 10.50000 0.01754 0.02494 =
0.04352 0.00000 0.00455 0.00000
AFIX 43
H3 2 0.663637 0.250000 0.012072 10.50000 -1.20000
AFIX 0
C4 1 0.597369 0.250000 0.234003 10.50000 0.02016 0.03096 =
0.04181 0.00000 -0.00602 0.00000
AFIX 43
H4 2 0.645287 0.250000 0.306217 10.50000 -1.20000
AFIX 0
C5 1 0.517532 0.250000 0.306867 10.50000 0.02407 0.02970 =
0.02759 0.00000 -0.00395 0.00000
AFIX 43
H5 2 0.509965 0.250000 0.427178 10.50000 -1.20000
AFIX 0
C6 1 0.450029 0.250000 0.196699 10.50000 0.01920 0.01806 =
0.02344 0.00000 0.00153 0.00000
C7 1 0.356461 0.250000 0.226393 10.50000 0.01896 0.02353 =
0.01987 0.00000 0.00164 0.00000
C8 1 0.375990 0.250000 -0.049959 10.50000 0.02316 0.01725 =
0.02142 0.00000 -0.00132 0.00000
CL1 4 0.322646 0.040778 0.340403 11.00000 0.02739 0.02648 =
0.02733 0.00320 0.00501 -0.00375
CL2 4 0.358510 0.250000 -0.264810 10.50000 0.03154 0.03465 =
0.01934 0.00000 -0.00149 0.00000
N1 3 0.315756 0.250000 0.058049 10.50000 0.01899 0.02729 =
0.02197 0.00000 -0.00101 0.00000
HKLF 4

REM 12gyte78 in Pnma
REM R1 = 0.0220 for 798 Fo > 4sig(Fo) and 0.0230 for all 834 data
REM 70 parameters refined using 0 restraints

END

WGHT 0.0346 0.3105
REM Highest difference peak 0.183, deepest hole -0.353, 1-sigma level 0.081
Q1 1 0.3377 0.1449 0.2800 11.00000 0.05 0.18
Q2 1 0.4088 0.2500 0.2219 10.50000 0.05 0.17
Q3 1 0.4580 0.1949 0.1206 11.00000 0.05 0.14
Q4 1 0.4706 0.0498 -0.0445 11.00000 0.05 0.14
Q5 1 0.2423 0.1351 -0.0050 11.00000 0.05 0.13
Q6 1 0.6933 0.0680 0.2707 11.00000 0.05 0.13
Q7 1 0.6001 0.1717 0.1434 11.00000 0.05 0.13
Q8 1 0.5275 0.0629 -0.0444 11.00000 0.05 0.13
Q9 1 0.3639 -0.0850 0.2510 11.00000 0.05 0.13
Q10 1 0.3789 -0.1074 0.4170 11.00000 0.05 0.12
;


_database_code_depnum_ccdc_archive 'CCDC 876241'
#######################################################################
#
#                 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_I
#TrackingRef '12gyte190.cif'

_chemical_name_systematic        ?
_chemical_name_common            1,1,3,4,5,6,7-heptachloro-1H-isoindole
_chemical_formula_moiety         'C8 H2 Cl5 N '
_chemical_formula_sum            'C8 H2 Cl5 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         289.36

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.8916(7)
_cell_length_b                   7.1079(7)
_cell_length_c                   9.4988(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.514(7)
_cell_angle_gamma                90
_cell_volume                     528.24(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1897
_cell_measurement_theta_min      2.6033
_cell_measurement_theta_max      27.4499
_cell_measurement_temperature    299.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284

_exptl_absorpt_coefficient_mu    1.326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      299.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            3948
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_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.
;

_reflns_number_total             1015
_reflns_number_gt                868
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0984
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_number_reflns         1015
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0555P)²+0.0057P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2 v2012.4-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0617(4) 0.25 0.2660(3) 0.0383(7) Uani d S 1 . .
C C2 -0.0710(4) 0.25 0.3476(4) 0.0404(7) Uani d S 1 . .
H H2 -0.1845 0.25 0.3061 0.048 Uiso calc SR 1 . .
C C3 -0.0286(4) 0.25 0.4921(4) 0.0384(7) Uani d S 1 . .
C C4 0.1432(4) 0.25 0.5555(3) 0.0385(7) Uani d S 1 . .
C C5 0.2752(4) 0.25 0.4695(3) 0.0411(7) Uani d S 1 . .
H H5 0.3893 0.25 0.5094 0.049 Uiso calc SR 1 . .
C C6 0.2311(3) 0.25 0.3263(3) 0.0374(7) Uani d S 1 . .
C C7 0.3356(4) 0.25 0.2042(4) 0.0431(7) Uani d S 1 . .
C C8 0.0669(4) 0.25 0.1125(4) 0.0453(8) Uani d S 1 . .
Cl Cl1 0.46801(7) 0.04667(9) 0.20628(7) 0.0583(3) Uani d . 1 . .
Cl Cl2 -0.11650(11) 0.25 -0.00464(11) 0.0650(3) Uani d S 1 . .
Cl Cl3 -0.19007(10) 0.25 0.59876(10) 0.0545(3) Uani d S 1 . .
Cl Cl4 0.19157(11) 0.25 0.73712(9) 0.0507(3) Uani d S 1 . .
N N1 0.2150(4) 0.25 0.0728(3) 0.0495(7) Uani d S 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0363(15) 0.0353(15) 0.0415(18) 0 -0.0013(13) 0
C2 0.0333(15) 0.0395(16) 0.047(2) 0 -0.0001(14) 0
C3 0.0348(15) 0.0339(14) 0.047(2) 0 0.0078(14) 0
C4 0.0419(16) 0.0339(14) 0.0386(18) 0 0.0008(14) 0
C5 0.0340(16) 0.0449(17) 0.044(2) 0 0.0022(14) 0
C6 0.0303(14) 0.0377(15) 0.0433(19) 0 0.0011(13) 0
C7 0.0360(15) 0.0511(17) 0.043(2) 0 0.0065(14) 0
C8 0.0422(18) 0.0460(18) 0.046(2) 0 -0.0027(15) 0
Cl1 0.0485(4) 0.0625(5) 0.0654(5) 0.0127(3) 0.0128(3) -0.0033(3)
Cl2 0.0490(5) 0.0933(7) 0.0482(6) 0 -0.0109(4) 0
Cl3 0.0459(5) 0.0619(5) 0.0591(6) 0 0.0196(4) 0
Cl4 0.0527(5) 0.0599(5) 0.0392(5) 0 0.0048(4) 0
N1 0.0476(16) 0.0587(17) 0.0420(17) 0 0.0055(13) 0

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.382(4) ?
C1 C6 . 1.384(4) ?
C1 C8 . 1.465(5) ?
C2 C3 . 1.369(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.410(4) ?
C3 Cl3 . 1.729(3) ?
C4 C5 . 1.405(4) ?
C4 Cl4 . 1.718(3) ?
C5 C6 . 1.359(4) ?
C5 H5 . 0.93 ?
C6 C7 . 1.508(4) ?
C7 N1 . 1.467(4) ?
C7 Cl1 4_565 1.7821(18) ?
C7 Cl1 . 1.7821(18) ?
C8 N1 . 1.274(4) ?
C8 Cl2 . 1.706(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 122.0(3) ?
C2 C1 C8 . . 132.9(3) ?
C6 C1 C8 . . 105.1(3) ?
C3 C2 C1 . . 117.3(3) ?
C3 C2 H2 . . 121.4 ?
C1 C2 H2 . . 121.4 ?
C2 C3 C4 . . 121.6(3) ?
C2 C3 Cl3 . . 119.0(2) ?
C4 C3 Cl3 . . 119.4(3) ?
C5 C4 C3 . . 119.8(3) ?
C5 C4 Cl4 . . 120.0(2) ?
C3 C4 Cl4 . . 120.3(2) ?
C6 C5 C4 . . 118.0(3) ?
C6 C5 H5 . . 121.0 ?
C4 C5 H5 . . 121.0 ?
C5 C6 C1 . . 121.4(3) ?
C5 C6 C7 . . 132.4(3) ?
C1 C6 C7 . . 106.1(3) ?
N1 C7 C6 . . 107.2(2) ?
N1 C7 Cl1 . 4_565 108.87(15) ?
C6 C7 Cl1 . 4_565 111.74(15) ?
N1 C7 Cl1 . . 108.87(15) ?
C6 C7 Cl1 . . 111.74(15) ?
Cl1 C7 Cl1 4_565 . 108.39(16) ?
N1 C8 C1 . . 116.2(3) ?
N1 C8 Cl2 . . 122.7(3) ?
C1 C8 Cl2 . . 121.1(2) ?
C8 N1 C7 . . 105.4(3) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0 ?
C8 C1 C2 C3 . . . . 180.0 ?
C1 C2 C3 C4 . . . . 0 ?
C1 C2 C3 Cl3 . . . . 180.0 ?
C2 C3 C4 C5 . . . . 0 ?
Cl3 C3 C4 C5 . . . . 180.0 ?
C2 C3 C4 Cl4 . . . . 180.0 ?
Cl3 C3 C4 Cl4 . . . . 0 ?
C3 C4 C5 C6 . . . . 0 ?
Cl4 C4 C5 C6 . . . . 180.0 ?
C4 C5 C6 C1 . . . . 0 ?
C4 C5 C6 C7 . . . . 180.0 ?
C2 C1 C6 C5 . . . . 0 ?
C8 C1 C6 C5 . . . . 180.0 ?
C2 C1 C6 C7 . . . . 180.0 ?
C8 C1 C6 C7 . . . . 0 ?
C5 C6 C7 N1 . . . . 180.0 ?
C1 C6 C7 N1 . . . . 0 ?
C5 C6 C7 Cl1 . . . 4_565 -60.82(15) ?
C1 C6 C7 Cl1 . . . 4_565 119.18(15) ?
C5 C6 C7 Cl1 . . . . 60.82(15) ?
C1 C6 C7 Cl1 . . . . -119.18(15) ?
C2 C1 C8 N1 . . . . 180.0 ?
C6 C1 C8 N1 . . . . 0 ?
C2 C1 C8 Cl2 . . . . 0 ?
C6 C1 C8 Cl2 . . . . 180.0 ?
C1 C8 N1 C7 . . . . 0 ?
Cl2 C8 N1 C7 . . . . 180.0 ?
C6 C7 N1 C8 . . . . 0 ?
Cl1 C7 N1 C8 4_565 . . . -121.01(13) ?
Cl1 C7 N1 C8 . . . . 121.01(13) ?



_database_code_depnum_ccdc_archive 'CCDC 913163'
