# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_C5CL5N_200K
_database_code_depnum_ccdc_archive 'CCDC 1400022'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Pentachloropyridine
_chemical_name_common            C5CL5N_200K
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 Cl5 N'
_chemical_formula_sum            'C5 Cl5 N'
_chemical_formula_weight         251.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.3290(14)
_cell_length_b                   5.1935(13)
_cell_length_c                   14.949(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.833(5)
_cell_angle_gamma                90
_cell_volume                     407.66(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    499
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.74

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.047
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.701
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2974
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.766
_diffrn_reflns_theta_max         30.771
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.751
_diffrn_reflns_point_group_measured_fraction_full 0.871
_reflns_number_total             1926
_reflns_number_gt                1551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_max     0.595
_reflns_Friedel_fraction_full    0.743

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0400P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 460 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1926
_refine_ls_number_parameters     100
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1144(3) 0.6748(4) 0.33204(11) 0.0345(4) Uani 1 1 d . . . . .
Cl2 Cl 0.5285(3) 1.1050(4) 0.32389(10) 0.0363(5) Uani 1 1 d . . . . .
Cl3 Cl 0.9611(3) 1.1745(3) 0.49191(12) 0.0337(4) Uani 1 1 d . . . . .
Cl4 Cl 0.9700(3) 0.8150(4) 0.65997(12) 0.0372(4) Uani 1 1 d . . . . .
Cl5 Cl 0.5361(3) 0.3993(4) 0.65424(11) 0.0354(5) Uani 1 1 d . . . . .
C1 C 0.3582(12) 0.7241(14) 0.4220(4) 0.0259(15) Uani 1 1 d . . . . .
C2 C 0.5375(13) 0.9145(14) 0.4175(4) 0.0235(14) Uani 1 1 d . . . . .
C3 C 0.7335(13) 0.9460(14) 0.4929(5) 0.0253(14) Uani 1 1 d . . . . .
C4 C 0.7334(12) 0.7850(13) 0.5674(4) 0.0232(13) Uani 1 1 d . . . . .
C5 C 0.5424(14) 0.6043(13) 0.5640(5) 0.0250(15) Uani 1 1 d . . . . .
N1 N 0.3616(11) 0.5732(12) 0.4935(4) 0.0242(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
Cl1 0.0304(9) 0.0412(10) 0.0284(8) -0.0037(9) -0.0049(7) -0.0025(9)
Cl2 0.0456(13) 0.0353(11) 0.0278(8) 0.0099(8) 0.0060(9) 0.0006(8)
Cl3 0.0293(8) 0.0322(9) 0.0405(9) -0.0042(8) 0.0081(7) -0.0083(8)
Cl4 0.0316(10) 0.0468(12) 0.0295(8) -0.0019(9) -0.0058(7) 0.0006(10)
Cl5 0.0420(11) 0.0360(12) 0.0286(8) 0.0078(8) 0.0074(8) -0.0006(9)
C1 0.019(3) 0.033(4) 0.025(3) -0.001(3) 0.005(3) 0.000(3)
C2 0.023(3) 0.027(4) 0.022(3) -0.006(2) 0.007(2) 0.002(3)
C3 0.023(3) 0.024(3) 0.030(3) -0.001(3) 0.007(3) 0.000(3)
C4 0.025(3) 0.024(4) 0.020(3) -0.006(3) 0.000(2) 0.004(3)
C5 0.029(4) 0.022(4) 0.024(3) 0.002(3) 0.003(3) 0.006(3)
N1 0.022(3) 0.026(3) 0.025(3) -0.003(2) 0.003(2) -0.005(2)

_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
Cl1 C1 1.722(7) . ?
Cl2 C2 1.708(7) . ?
Cl3 C3 1.699(7) . ?
Cl4 C4 1.712(6) . ?
Cl5 C5 1.723(7) . ?
C1 N1 1.323(9) . ?
C1 C2 1.384(9) . ?
C2 C3 1.410(10) . ?
C3 C4 1.392(9) . ?
C4 C5 1.379(9) . ?
C5 N1 1.311(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.2(6) . . ?
N1 C1 Cl1 116.6(5) . . ?
C2 C1 Cl1 120.2(5) . . ?
C1 C2 C3 117.9(6) . . ?
C1 C2 Cl2 122.0(5) . . ?
C3 C2 Cl2 120.1(6) . . ?
C4 C3 C2 117.9(6) . . ?
C4 C3 Cl3 121.6(6) . . ?
C2 C3 Cl3 120.4(6) . . ?
C5 C4 C3 118.7(6) . . ?
C5 C4 Cl4 121.9(5) . . ?
C3 C4 Cl4 119.4(5) . . ?
N1 C5 C4 123.3(6) . . ?
N1 C5 Cl5 116.3(6) . . ?
C4 C5 Cl5 120.3(5) . . ?
C5 N1 C1 118.9(6) . . ?

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-2

_shelx_res_file                  
;
TITL a14_96 in Pc
CELL 0.71073   5.3290   5.1935  14.9491  90.000  99.833  90.000
ZERR    2.00   0.0014   0.0013   0.0040   0.000   0.005   0.000
LATT -1
SYMM X, -Y, 0.5+Z
SFAC  C   N   CL
UNIT   10    2  10
TEMP -73
L.S. 8
ACTA
SIZE 0.26 0.24 0.06
BOND
FMAP 2
PLAN -20
WGHT    0.040000
FVAR       0.26595
CL1   3    0.114430    0.674843    0.332038    11.00000    0.03044    0.04123 =
         0.02844   -0.00367   -0.00494   -0.00247
CL2   3    0.528532    1.104992    0.323893    11.00000    0.04562    0.03527 =
         0.02781    0.00987    0.00601    0.00057
CL3   3    0.961096    1.174543    0.491907    11.00000    0.02926    0.03223 =
         0.04051   -0.00423    0.00810   -0.00827
CL4   3    0.969965    0.815006    0.659971    11.00000    0.03157    0.04683 =
         0.02948   -0.00194   -0.00576    0.00061
CL5   3    0.536135    0.399271    0.654235    11.00000    0.04195    0.03599 =
         0.02862    0.00782    0.00743   -0.00059
C1    1    0.358249    0.724133    0.421989    11.00000    0.01942    0.03316 =
         0.02533   -0.00080    0.00481    0.00031
C2    1    0.537505    0.914492    0.417526    11.00000    0.02284    0.02668 =
         0.02210   -0.00563    0.00700    0.00161
C3    1    0.733546    0.946002    0.492938    11.00000    0.02327    0.02359 =
         0.02993   -0.00085    0.00729    0.00011
C4    1    0.733426    0.784998    0.567402    11.00000    0.02459    0.02371 =
         0.02008   -0.00558    0.00008    0.00428
C5    1    0.542416    0.604313    0.564020    11.00000    0.02928    0.02159 =
         0.02356    0.00242    0.00323    0.00600
N1    2    0.361631    0.573211    0.493491    11.00000    0.02163    0.02592 =
         0.02478   -0.00253    0.00290   -0.00497
HKLF 4

REM  a14_96 in Pc
REM R1 =  0.0474 for    1551 Fo > 4sig(Fo)  and  0.0638 for all    1926 data
REM    100 parameters refined using      2 restraints

END

WGHT      0.0402      0.0000

REM Highest difference peak  0.583,  deepest hole -0.383,  1-sigma level  0.099
Q1    1   1.1269  1.3128  0.4920  11.00000  0.05    0.58
Q2    1   0.3792  0.9841  0.2982  11.00000  0.05    0.42
Q3    1   0.7002  0.8778  0.5316  11.00000  0.05    0.41
Q4    1   0.3939  0.6027  0.4547  11.00000  0.05    0.39
Q5    1   1.1169  0.7056  0.6774  11.00000  0.05    0.37
Q6    1   0.8397  0.6855  0.6326  11.00000  0.05    0.37
Q7    1   1.1155  0.9589  0.6583  11.00000  0.05    0.36
Q8    1   0.3501  1.1879  0.3066  11.00000  0.05    0.34
Q9    1  -0.0285  0.5354  0.3163  11.00000  0.05    0.34
Q10   1   0.5148  0.5862  0.5070  11.00000  0.05    0.33
Q11   1   0.3452  0.3947  0.2781  11.00000  0.05    0.33
Q12   1   1.0043  1.0626  0.6520  11.00000  0.05    0.32
Q13   1   0.6624  1.2303  0.3403  11.00000  0.05    0.32
Q14   1  -0.0348  0.7946  0.3178  11.00000  0.05    0.32
Q15   1   0.8121  1.2860  0.4875  11.00000  0.05    0.32
Q16   1   1.1185  1.0890  0.5090  11.00000  0.05    0.32
Q17   1   0.3944  1.1681  0.2505  11.00000  0.05    0.32
Q18   1   0.1249  0.6516  0.3127  11.00000  0.05    0.32
Q19   1   0.4352  0.2354  0.6431  11.00000  0.05    0.31
Q20   1   0.6833  0.5165  0.6861  11.00000  0.05    0.31
;
_shelx_res_checksum              44049
####################################################################### 
# 
# 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_C5CL5N_150K
_database_code_depnum_ccdc_archive 'CCDC 1400028'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Pentachloropyridine
_chemical_name_common            C5CL5N_150K
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 Cl5 N'
_chemical_formula_sum            'C5 Cl5 N'
_chemical_formula_weight         251.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.3191(16)
_cell_length_b                   5.1827(16)
_cell_length_c                   14.894(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.704(5)
_cell_angle_gamma                90
_cell_volume                     404.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1894
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      29.97

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.062
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.713
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5904
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2934
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.775
_diffrn_reflns_theta_max         30.904
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.733
_diffrn_reflns_point_group_measured_fraction_full 0.868
_reflns_number_total             1894
_reflns_number_gt                1769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_max     0.581
_reflns_Friedel_fraction_full    0.736

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0491P)²+0.0598P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.16(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1894
_refine_ls_number_parameters     100
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1125(2) 0.6767(3) 0.33176(9) 0.0251(3) Uani 1 1 d . . . . .
Cl2 Cl 0.5279(2) 1.1081(3) 0.32354(8) 0.0264(4) Uani 1 1 d . . . . .
Cl3 Cl 0.9619(3) 1.1754(2) 0.49192(10) 0.0250(3) Uani 1 1 d . . . . .
Cl4 Cl 0.9719(2) 0.8141(3) 0.66042(9) 0.0270(3) Uani 1 1 d . . . . .
Cl5 Cl 0.5366(3) 0.3961(3) 0.65471(9) 0.0257(3) Uani 1 1 d . . . . .
C1 C 0.3565(10) 0.7238(10) 0.4211(3) 0.0178(10) Uani 1 1 d . . . . .
C2 C 0.5379(12) 0.9144(11) 0.4172(4) 0.0194(11) Uani 1 1 d . . . . .
C3 C 0.7342(11) 0.9464(11) 0.4927(4) 0.0176(10) Uani 1 1 d . . . . .
C4 C 0.7366(11) 0.7841(10) 0.5675(4) 0.0193(11) Uani 1 1 d . . . . .
C5 C 0.5429(12) 0.6016(10) 0.5638(4) 0.0192(11) Uani 1 1 d . . . . .
N1 N 0.3621(10) 0.5711(9) 0.4940(3) 0.0181(9) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0217(7) 0.0304(7) 0.0211(6) -0.0022(6) -0.0026(5) -0.0008(6)
Cl2 0.0324(9) 0.0256(7) 0.0215(6) 0.0074(5) 0.0054(6) 0.0001(5)
Cl3 0.0215(6) 0.0230(6) 0.0314(6) -0.0025(6) 0.0074(5) -0.0057(5)
Cl4 0.0227(8) 0.0339(7) 0.0221(6) -0.0017(6) -0.0029(5) -0.0009(6)
Cl5 0.0315(8) 0.0249(7) 0.0214(6) 0.0047(5) 0.0061(6) -0.0006(6)
C1 0.015(3) 0.020(3) 0.019(2) -0.0032(19) 0.003(2) 0.002(2)
C2 0.021(3) 0.020(2) 0.017(2) -0.0010(18) 0.006(2) 0.002(2)
C3 0.015(2) 0.015(2) 0.022(2) -0.003(2) 0.0023(19) -0.002(2)
C4 0.021(3) 0.022(3) 0.016(2) 0.000(2) 0.004(2) 0.003(2)
C5 0.021(3) 0.018(3) 0.019(2) 0.0025(19) 0.005(2) 0.004(2)
N1 0.018(2) 0.019(2) 0.0177(19) -0.0029(18) 0.0044(19) -0.0005(17)

_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
Cl1 C1 1.713(6) . ?
Cl2 C2 1.712(5) . ?
Cl3 C3 1.697(6) . ?
Cl4 C4 1.709(6) . ?
Cl5 C5 1.727(6) . ?
C1 N1 1.339(7) . ?
C1 C2 1.389(8) . ?
C2 C3 1.410(8) . ?
C3 C4 1.394(8) . ?
C4 C5 1.393(8) . ?
C5 N1 1.302(8) . ?

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 122.3(5) . . ?
N1 C1 Cl1 117.1(4) . . ?
C2 C1 Cl1 120.6(4) . . ?
C1 C2 C3 118.4(5) . . ?
C1 C2 Cl2 121.7(4) . . ?
C3 C2 Cl2 119.9(4) . . ?
C4 C3 C2 118.2(5) . . ?
C4 C3 Cl3 121.2(5) . . ?
C2 C3 Cl3 120.7(4) . . ?
C5 C4 C3 118.1(5) . . ?
C5 C4 Cl4 122.0(4) . . ?
C3 C4 Cl4 119.9(4) . . ?
N1 C5 C4 123.8(5) . . ?
N1 C5 Cl5 116.2(4) . . ?
C4 C5 Cl5 120.0(5) . . ?
C5 N1 C1 119.2(5) . . ?

_refine_diff_density_max         0.680
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.107

_shelxl_version_number           2013-2

_shelx_res_file                  
;
TITL C5Cl5N in Pc
CELL 0.71073   5.3191   5.1827  14.8936  90.000  99.704  90.000
ZERR    2.00   0.0016   0.0016   0.0047   0.000   0.005   0.000
LATT -1
SYMM X, -Y, 0.5+Z
SFAC  C   N   CL
UNIT   10    2  10
TEMP -123
L.S. 8
SIZE 0.26 0.24 0.06
BOND
ACTA
FMAP 2
PLAN -30
WGHT    0.049100    0.059800
FVAR       0.25803
CL1   3    0.112521    0.676739    0.331762    11.00000    0.02173    0.03043 =
         0.02112   -0.00221   -0.00260   -0.00084
CL2   3    0.527909    1.108136    0.323536    11.00000    0.03236    0.02560 =
         0.02151    0.00744    0.00536    0.00005
CL3   3    0.961855    1.175447    0.491922    11.00000    0.02152    0.02298 =
         0.03143   -0.00245    0.00743   -0.00568
CL4   3    0.971928    0.814135    0.660417    11.00000    0.02271    0.03390 =
         0.02212   -0.00166   -0.00286   -0.00092
CL5   3    0.536567    0.396067    0.654706    11.00000    0.03145    0.02492 =
         0.02139    0.00474    0.00608   -0.00062
C1    1    0.356520    0.723845    0.421131    11.00000    0.01504    0.01950 =
         0.01888   -0.00323    0.00268    0.00219
C2    1    0.537942    0.914412    0.417196    11.00000    0.02118    0.02041 =
         0.01746   -0.00103    0.00612    0.00158
C3    1    0.734214    0.946406    0.492734    11.00000    0.01527    0.01523 =
         0.02209   -0.00306    0.00234   -0.00175
C4    1    0.736559    0.784106    0.567522    11.00000    0.02064    0.02155 =
         0.01589    0.00006    0.00379    0.00280
C5    1    0.542900    0.601592    0.563819    11.00000    0.02085    0.01800 =
         0.01901    0.00250    0.00452    0.00388
N1    2    0.362092    0.571116    0.493969    11.00000    0.01843    0.01861 =
         0.01767   -0.00291    0.00439   -0.00048
HKLF 4

REM  C5Cl5N in Pc
REM R1 =  0.0388 for    1769 Fo > 4sig(Fo)  and  0.0427 for all    1894 data
REM    100 parameters refined using      2 restraints

END

WGHT      0.0452      0.0998

REM Highest difference peak  0.680,  deepest hole -0.407,  1-sigma level  0.107
Q1    1   1.1231  1.3085  0.4964  11.00000  0.05    0.68
Q2    1   0.7080  0.9100  0.5397  11.00000  0.05    0.51
Q3    1   1.1016  0.6922  0.6750  11.00000  0.05    0.50
Q4    1   0.8398  0.7152  0.6469  11.00000  0.05    0.49
Q5    1   0.2436  0.7644  0.3512  11.00000  0.05    0.48
Q6    1   0.8427  1.2837  0.4752  11.00000  0.05    0.44
Q7    1  -0.0147  0.5643  0.3109  11.00000  0.05    0.43
Q8    1   0.3752  0.5886  0.4475  11.00000  0.05    0.41
Q9    1   0.3042  0.6729  0.4620  11.00000  0.05    0.41
Q10   1   0.4278  0.5115  0.6362  11.00000  0.05    0.39
Q11   1   0.6945  1.1599  0.3399  11.00000  0.05    0.38
Q12   1   0.4785  0.5054  0.5144  11.00000  0.05    0.38
Q13   1   0.3966  0.3251  0.6355  11.00000  0.05    0.38
Q14   1   1.0187  0.7533  0.6185  11.00000  0.05    0.38
Q15   1   0.5848  0.5225  0.5997  11.00000  0.05    0.37
Q16   1   0.1728  0.5910  0.3504  11.00000  0.05    0.37
Q17   1   0.3692  1.0184  0.3091  11.00000  0.05    0.36
Q18   1   0.3921  0.6452  0.5094  11.00000  0.05    0.36
Q19   1   0.5137  1.0115  0.3821  11.00000  0.05    0.35
Q20   1   0.3966  1.2301  0.3069  11.00000  0.05    0.35
Q21   1   0.6485  0.3126  0.6807  11.00000  0.05    0.34
Q22   1   0.6027  0.7161  0.5699  11.00000  0.05    0.34
Q23   1   0.6203  0.9907  0.3449  11.00000  0.05    0.34
Q24   1   0.8240  1.0871  0.4811  11.00000  0.05    0.34
Q25   1  -0.0389  0.8170  0.3265  11.00000  0.05    0.33
Q26   1   1.0149  1.2680  0.4392  11.00000  0.05    0.32
Q27   1   0.7065  0.6403  0.5697  11.00000  0.05    0.32
Q28   1   0.6482  0.4858  0.6783  11.00000  0.05    0.32
Q29   1   0.4784  0.8031  0.4159  11.00000  0.05    0.32
Q30   1   0.6568  0.8875  0.4450  11.00000  0.05    0.31
;
_shelx_res_checksum              99526
####################################################################### 
# 
# 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_C5CL5N_100K
_database_code_depnum_ccdc_archive 'CCDC 1400034'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Pentachloropyridine
_chemical_name_common            C5CL5N_100K
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 Cl5 N'
_chemical_formula_sum            'C5 Cl5 N'
_chemical_formula_weight         251.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.3122(2)
_cell_length_b                   5.1770(2)
_cell_length_c                   14.8307(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.493(2)
_cell_angle_gamma                90
_cell_volume                     402.28(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1878
_cell_measurement_theta_min      24.17
_cell_measurement_theta_max      42.46

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.075
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.724
_shelx_estimated_absorpt_T_min   0.663
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7866
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29541
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.785
_diffrn_reflns_theta_max         49.718
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7455
_reflns_number_gt                6543
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.819
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0419P)²+0.0822P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2633 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7455
_refine_ls_number_parameters     100
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11089(8) 0.67833(10) 0.33158(3) 0.01608(7) Uani 1 1 d . . . . .
Cl2 Cl 0.52677(8) 1.11133(10) 0.32314(3) 0.01650(8) Uani 1 1 d . . . . .
Cl3 Cl 0.96263(9) 1.17687(8) 0.49186(3) 0.01503(6) Uani 1 1 d . . . . .
Cl4 Cl 0.97371(8) 0.81227(10) 0.66087(3) 0.01657(7) Uani 1 1 d . . . . .
Cl5 Cl 0.53729(9) 0.39356(9) 0.65500(3) 0.01629(7) Uani 1 1 d . . . . .
C1 C 0.3566(3) 0.7247(3) 0.42143(11) 0.0118(2) Uani 1 1 d . . . . .
C2 C 0.5391(3) 0.9172(3) 0.41700(11) 0.0116(2) Uani 1 1 d . . . . .
C3 C 0.7333(3) 0.9459(3) 0.49222(12) 0.0118(2) Uani 1 1 d . . . . .
C4 C 0.7382(3) 0.7843(3) 0.56807(11) 0.0118(2) Uani 1 1 d . . . . .
C5 C 0.5450(3) 0.6008(3) 0.56445(11) 0.0119(2) Uani 1 1 d . . . . .
N1 N 0.3599(3) 0.5715(3) 0.49341(10) 0.0126(2) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01394(16) 0.01948(17) 0.01339(13) -0.00134(12) -0.00197(10) -0.00135(13)
Cl2 0.01958(19) 0.01634(18) 0.01353(13) 0.00405(11) 0.00254(12) -0.00028(12)
Cl3 0.01301(14) 0.01353(14) 0.01898(15) -0.00139(12) 0.00391(10) -0.00342(11)
Cl4 0.01422(15) 0.02058(18) 0.01336(13) -0.00091(13) -0.00226(10) -0.00058(13)
Cl5 0.02013(18) 0.01586(16) 0.01308(13) 0.00330(12) 0.00331(11) -0.00081(13)
C1 0.0112(5) 0.0130(5) 0.0111(4) -0.0002(4) 0.0012(4) -0.0002(4)
C2 0.0117(5) 0.0112(5) 0.0117(5) 0.0007(4) 0.0014(4) -0.0008(4)
C3 0.0103(5) 0.0120(5) 0.0131(5) -0.0008(4) 0.0020(4) -0.0009(4)
C4 0.0116(5) 0.0124(5) 0.0111(4) -0.0005(4) 0.0006(4) -0.0005(4)
C5 0.0127(5) 0.0118(5) 0.0110(4) 0.0000(4) 0.0019(4) -0.0001(4)
N1 0.0125(5) 0.0132(5) 0.0118(4) 0.0002(4) 0.0008(3) -0.0017(4)

_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
Cl1 C1 1.7213(16) . ?
Cl2 C2 1.7093(17) . ?
Cl3 C3 1.7077(18) . ?
Cl4 C4 1.7063(17) . ?
Cl5 C5 1.7247(17) . ?
C1 N1 1.328(2) . ?
C1 C2 1.400(3) . ?
C2 C3 1.397(2) . ?
C3 C4 1.399(2) . ?
C4 C5 1.393(2) . ?
C5 N1 1.326(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.06(15) . . ?
N1 C1 Cl1 116.55(13) . . ?
C2 C1 Cl1 120.39(13) . . ?
C3 C2 C1 117.67(16) . . ?
C3 C2 Cl2 120.80(14) . . ?
C1 C2 Cl2 121.53(13) . . ?
C2 C3 C4 119.49(16) . . ?
C2 C3 Cl3 120.34(14) . . ?
C4 C3 Cl3 120.17(13) . . ?
C5 C4 C3 117.44(15) . . ?
C5 C4 Cl4 121.76(13) . . ?
C3 C4 Cl4 120.80(14) . . ?
N1 C5 C4 123.63(16) . . ?
N1 C5 Cl5 115.97(14) . . ?
C4 C5 Cl5 120.40(13) . . ?
C5 N1 C1 118.71(16) . . ?

_refine_diff_density_max         1.097
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.121

_shelxl_version_number           2013-2

_shelx_res_file                  
;
TITL a14_alldata_p2m in Pc
CELL  0.71073    5.3122    5.1770   14.8307   90.0000   99.4932   90.0000
ZERR   2.00      0.0002    0.0002    0.0006    0.0000    0.0021    0.0000
LATT -1
SYMM X, -Y, 0.5+Z
SFAC  C   N   CL
UNIT   10    2  10
TEMP -173
SIZE 0.26 0.24 0.06
OMIT -3
L.S. 8
BOND
ACTA
FMAP 2
PLAN -20
WGHT    0.041900    0.082200
FVAR       0.81508
CL1   3    0.110891    0.678335    0.331582    11.00000    0.01394    0.01948 =
         0.01339   -0.00134   -0.00197   -0.00135
CL2   3    0.526767    1.111335    0.323143    11.00000    0.01958    0.01634 =
         0.01353    0.00405    0.00254   -0.00028
CL3   3    0.962635    1.176874    0.491857    11.00000    0.01301    0.01353 =
         0.01898   -0.00139    0.00391   -0.00342
CL4   3    0.973707    0.812274    0.660865    11.00000    0.01422    0.02058 =
         0.01336   -0.00091   -0.00226   -0.00058
CL5   3    0.537292    0.393565    0.654995    11.00000    0.02013    0.01586 =
         0.01308    0.00330    0.00331   -0.00081
C1    1    0.356571    0.724749    0.421431    11.00000    0.01118    0.01296 =
         0.01109   -0.00020    0.00125   -0.00015
C2    1    0.539130    0.917239    0.417004    11.00000    0.01166    0.01121 =
         0.01170    0.00075    0.00145   -0.00078
C3    1    0.733283    0.945930    0.492224    11.00000    0.01035    0.01200 =
         0.01313   -0.00080    0.00203   -0.00094
C4    1    0.738240    0.784347    0.568072    11.00000    0.01156    0.01240 =
         0.01114   -0.00054    0.00063   -0.00046
C5    1    0.544957    0.600839    0.564447    11.00000    0.01274    0.01180 =
         0.01103    0.00002    0.00192   -0.00011
N1    2    0.359947    0.571489    0.493408    11.00000    0.01250    0.01320 =
         0.01180    0.00020    0.00075   -0.00173
HKLF 4

REM  a14_alldata_p2m in Pc
REM R1 =  0.0369 for    6543 Fo > 4sig(Fo)  and  0.0446 for all    7455 data
REM    100 parameters refined using      2 restraints

END

WGHT      0.0382      0.0994

REM Highest difference peak  1.097,  deepest hole -0.673,  1-sigma level  0.121
Q1    1   1.1189  1.3254  0.4926  11.00000  0.05    1.10
Q2    1   0.6422  1.1069  0.3210  11.00000  0.05    1.10
Q3    1   0.2123  0.6720  0.3291  11.00000  0.05    0.90
Q4    1   0.4397  0.3977  0.6578  11.00000  0.05    0.86
Q5    1   0.4124  1.1009  0.3228  11.00000  0.05    0.82
Q6    1   0.8705  0.8066  0.6668  11.00000  0.05    0.78
Q7    1   0.8538  1.1787  0.4902  11.00000  0.05    0.73
Q8    1   0.4702  0.5728  0.5098  11.00000  0.05    0.67
Q9    1   0.9758  0.9494  0.6612  11.00000  0.05    0.66
Q10   1   0.0134  0.6677  0.3418  11.00000  0.05    0.63
Q11   1   0.6514  0.3999  0.6605  11.00000  0.05    0.61
Q12   1   1.0811  0.8228  0.6557  11.00000  0.05    0.61
Q13   1   0.1088  0.7871  0.3300  11.00000  0.05    0.60
Q14   1   0.1078  0.6783  0.3095  11.00000  0.05    0.59
Q15   1   0.3565  0.6708  0.4612  11.00000  0.05    0.59
Q16   1   0.6326  0.9248  0.4592  11.00000  0.05    0.59
Q17   1   0.0894  0.5507  0.3181  11.00000  0.05    0.59
Q18   1   0.5136  0.5366  0.6526  11.00000  0.05    0.57
Q19   1   1.0710  1.1916  0.4841  11.00000  0.05    0.55
Q20   1   0.4766  0.7748  0.4181  11.00000  0.05    0.54
;
_shelx_res_checksum              69629
####################################################################### 
# 
# 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_C5CL5N_250K
_database_code_depnum_ccdc_archive 'CCDC 1402263'
_audit_update_record             
;
2015-05-21 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Pentachloropyridine
_chemical_name_common            C5CL5N_250K
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 Cl5 N'
_chemical_formula_sum            'C5 Cl5 N'
_chemical_formula_weight         251.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.3426(15)
_cell_length_b                   5.2051(15)
_cell_length_c                   15.021(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.003(6)
_cell_angle_gamma                90
_cell_volume                     411.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    499
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.74

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.029
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.686
_shelx_estimated_absorpt_T_min   0.6077
_shelx_estimated_absorpt_T_max   0.7461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2999
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.754
_diffrn_reflns_theta_max         30.760
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_point_group_measured_fraction_full 0.873
_reflns_number_total             1939
_reflns_number_gt                1361
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_max     0.593
_reflns_Friedel_fraction_full    0.746

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0336P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 370 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1939
_refine_ls_number_parameters     100
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.007
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1167(3) 0.6729(5) 0.33222(12) 0.0448(5) Uani 1 1 d . . . . .
Cl2 Cl 0.5295(3) 1.1006(4) 0.32424(12) 0.0476(7) Uani 1 1 d . . . . .
Cl3 Cl 0.9599(4) 1.1728(4) 0.49197(14) 0.0437(5) Uani 1 1 d . . . . .
Cl4 Cl 0.9680(3) 0.8170(5) 0.65954(13) 0.0476(6) Uani 1 1 d . . . . .
Cl5 Cl 0.5350(4) 0.4024(4) 0.65386(13) 0.0454(6) Uani 1 1 d . . . . .
C1 C 0.3603(13) 0.7224(16) 0.4223(5) 0.0311(17) Uani 1 1 d . . . . .
C2 C 0.5388(15) 0.9107(15) 0.4178(5) 0.0299(17) Uani 1 1 d . . . . .
C3 C 0.5450(15) 0.6053(14) 0.5641(5) 0.0308(18) Uani 1 1 d . . . . .
C4 C 0.7318(15) 0.9432(15) 0.4927(5) 0.0319(17) Uani 1 1 d . . . . .
C5 C 0.7352(13) 0.7844(15) 0.5675(5) 0.0303(16) Uani 1 1 d . . . . .
N1 N 0.3611(12) 0.5730(13) 0.4934(5) 0.0313(15) 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
Cl1 0.0397(11) 0.0545(13) 0.0358(10) -0.0028(11) -0.0060(8) -0.0026(11)
Cl2 0.0624(17) 0.0433(14) 0.0364(11) 0.0132(10) 0.0068(11) 0.0001(10)
Cl3 0.0392(10) 0.0403(11) 0.0531(11) -0.0065(10) 0.0121(8) -0.0123(10)
Cl4 0.0419(13) 0.0598(15) 0.0355(10) -0.0046(12) -0.0082(9) 0.0005(12)
Cl5 0.0554(14) 0.0459(15) 0.0358(10) 0.0106(10) 0.0105(10) -0.0005(11)
C1 0.026(4) 0.036(5) 0.030(4) -0.002(3) 0.001(3) 0.000(3)
C2 0.032(4) 0.032(5) 0.027(3) -0.001(3) 0.008(3) 0.002(3)
C3 0.033(4) 0.031(5) 0.027(3) 0.000(3) 0.003(3) 0.005(3)
C4 0.034(4) 0.028(4) 0.035(4) -0.009(3) 0.010(3) -0.002(3)
C5 0.028(4) 0.034(4) 0.028(4) -0.007(3) 0.005(3) 0.005(3)
N1 0.029(4) 0.032(4) 0.032(3) -0.002(3) 0.003(3) -0.001(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
Cl1 C1 1.726(7) . ?
Cl2 C2 1.712(7) . ?
Cl3 C4 1.708(8) . ?
Cl4 C5 1.700(7) . ?
Cl5 C3 1.721(8) . ?
C1 N1 1.321(10) . ?
C1 C2 1.378(10) . ?
C2 C4 1.399(11) . ?
C3 N1 1.326(10) . ?
C3 C5 1.373(10) . ?
C4 C5 1.392(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.6(7) . . ?
N1 C1 Cl1 116.3(6) . . ?
C2 C1 Cl1 120.1(6) . . ?
C1 C2 C4 117.8(7) . . ?
C1 C2 Cl2 122.0(6) . . ?
C4 C2 Cl2 120.2(6) . . ?
N1 C3 C5 123.8(7) . . ?
N1 C3 Cl5 115.4(6) . . ?
C5 C3 Cl5 120.8(6) . . ?
C5 C4 C2 118.8(7) . . ?
C5 C4 Cl3 120.8(6) . . ?
C2 C4 Cl3 120.4(6) . . ?
C3 C5 C4 117.9(7) . . ?
C3 C5 Cl4 122.0(6) . . ?
C4 C5 Cl4 120.1(6) . . ?
C1 N1 C3 118.1(7) . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-2

_shelx_res_file                  
;
TITL a14_95 in Pc
CELL 0.71073   5.3426   5.2051  15.0207  90.000 100.003  90.000
ZERR    2.00   0.0015   0.0015   0.0044   0.000   0.006   0.000
LATT -1
SYMM X, -Y, 0.5+Z
SFAC  C   N   CL
UNIT   10    2  10
TEMP -23
L.S. 12
BOND
ACTA
FMAP 2
PLAN -20
WGHT    0.033600
FVAR       0.28487
CL1   3    0.116690    0.672876    0.332217    11.00000    0.03968    0.05450 =
         0.03577   -0.00285   -0.00597   -0.00256
CL2   3    0.529466    1.100608    0.324243    11.00000    0.06236    0.04333 =
         0.03645    0.01322    0.00682    0.00007
CL3   3    0.959909    1.172838    0.491972    11.00000    0.03925    0.04027 =
         0.05309   -0.00646    0.01208   -0.01225
CL4   3    0.967980    0.817033    0.659542    11.00000    0.04192    0.05983 =
         0.03553   -0.00461   -0.00825    0.00055
CL5   3    0.534950    0.402430    0.653860    11.00000    0.05542    0.04592 =
         0.03576    0.01062    0.01048   -0.00048
C1    1    0.360286    0.722376    0.422313    11.00000    0.02581    0.03620 =
         0.02977   -0.00204    0.00077    0.00042
C2    1    0.538788    0.910728    0.417794    11.00000    0.03152    0.03247 =
         0.02679   -0.00142    0.00782    0.00158
C3    1    0.545043    0.605342    0.564087    11.00000    0.03269    0.03125 =
         0.02747    0.00042    0.00281    0.00515
C4    1    0.731816    0.943247    0.492734    11.00000    0.03352    0.02832 =
         0.03529   -0.00866    0.01003   -0.00172
C5    1    0.735210    0.784434    0.567464    11.00000    0.02841    0.03436 =
         0.02810   -0.00717    0.00496    0.00466
N1    2    0.361116    0.572995    0.493424    11.00000    0.02882    0.03207 =
         0.03210   -0.00235    0.00287   -0.00092
HKLF 4

REM  a14_95 in Pc
REM R1 =  0.0490 for    1361 Fo > 4sig(Fo)  and  0.0821 for all    1939 data
REM    100 parameters refined using      2 restraints

END

WGHT      0.0335      0.0000

REM Highest difference peak  0.399,  deepest hole -0.387,  1-sigma level  0.094
Q1    1   0.5956  0.5204  0.6027  11.00000  0.05    0.40
Q2    1   1.1355  1.3223  0.4933  11.00000  0.05    0.39
Q3    1   0.5162  0.5717  0.4912  11.00000  0.05    0.37
Q4    1   1.0713  1.2144  0.5528  11.00000  0.05    0.37
Q5    1   1.0250  1.3031  0.4377  11.00000  0.05    0.35
Q6    1   0.8438  0.6950  0.6624  11.00000  0.05    0.35
Q7    1   0.4255  0.5199  0.6319  11.00000  0.05    0.34
Q8    1   0.9964  0.7558  0.5905  11.00000  0.05    0.33
Q9    1   0.5475  0.9376  0.4964  11.00000  0.05    0.33
Q10   1   0.4494  0.8079  0.4019  11.00000  0.05    0.33
Q11   1   0.6696  1.0119  0.3610  11.00000  0.05    0.32
Q12   1   0.8442  1.0703  0.5314  11.00000  0.05    0.30
Q13   1   0.2752  0.6686  0.4722  11.00000  0.05    0.30
Q14   1  -0.0275  0.5191  0.3264  11.00000  0.05    0.30
Q15   1   0.4364  0.6807  0.5110  11.00000  0.05    0.30
Q16   1   0.1206  0.5266  0.2885  11.00000  0.05    0.29
Q17   1   1.1068  0.6878  0.6548  11.00000  0.05    0.29
Q18   1   1.2152  1.3292  0.5783  11.00000  0.05    0.29
Q19   1   0.4925  0.9832  0.3831  11.00000  0.05    0.29
Q20   1   0.5347  1.1573  0.3167  11.00000  0.05    0.29
;
_shelx_res_checksum              87495
####################################################################### 
# 
# 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_C5CL5N_300K
_database_code_depnum_ccdc_archive 'CCDC 1402264'
_audit_update_record             
;
2015-05-21 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Pentachloropyridine
_chemical_name_common            C5CL5N_300K
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 Cl5 N'
_chemical_formula_sum            'C5 Cl5 N'
_chemical_formula_weight         251.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.359(4)
_cell_length_b                   5.224(4)
_cell_length_c                   15.101(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.228(18)
_cell_angle_gamma                90
_cell_volume                     416.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    499
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.74

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.006
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.667
_shelx_estimated_absorpt_T_min   0.5633
_shelx_estimated_absorpt_T_max   0.7461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3012
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.741
_diffrn_reflns_theta_max         30.624
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_point_group_measured_fraction_full 0.862
_reflns_number_total             1936
_reflns_number_gt                1172
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_max     0.587
_reflns_Friedel_fraction_full    0.725

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0563P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     100
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1185(4) 0.6708(6) 0.33238(14) 0.0572(7) Uani 1 1 d . . . . .
Cl2 Cl 0.5309(4) 1.0973(5) 0.32478(15) 0.0607(9) Uani 1 1 d . . . . .
Cl3 Cl 0.9582(5) 1.1724(4) 0.49192(18) 0.0559(6) Uani 1 1 d . . . . .
Cl4 Cl 0.9659(4) 0.8200(6) 0.65956(15) 0.0601(7) Uani 1 1 d . . . . .
Cl5 Cl 0.5349(5) 0.4062(5) 0.65336(15) 0.0572(8) Uani 1 1 d . . . . .
C1 C 0.3589(16) 0.7219(18) 0.4213(6) 0.039(2) Uani 1 1 d . . . . .
C2 C 0.5392(18) 0.9080(17) 0.4180(6) 0.039(2) Uani 1 1 d . . . . .
C3 C 0.5433(18) 0.6051(16) 0.5631(6) 0.039(2) Uani 1 1 d . . . . .
C4 C 0.7316(17) 0.9418(18) 0.4913(6) 0.0398(19) Uani 1 1 d . . . . .
C5 C 0.7326(16) 0.7844(17) 0.5675(5) 0.040(2) Uani 1 1 d . . . . .
N1 N 0.3639(14) 0.5758(15) 0.4932(5) 0.0397(18) 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
Cl1 0.0495(14) 0.0697(16) 0.0466(12) -0.0074(13) -0.0076(10) -0.0035(14)
Cl2 0.077(2) 0.0572(19) 0.0475(13) 0.0179(12) 0.0110(14) 0.0027(13)
Cl3 0.0501(12) 0.0500(14) 0.0696(14) -0.0079(12) 0.0166(11) -0.0153(12)
Cl4 0.0510(16) 0.0772(19) 0.0453(12) -0.0037(14) -0.0096(11) 0.0003(16)
Cl5 0.0706(18) 0.0579(19) 0.0442(12) 0.0121(12) 0.0133(12) -0.0010(14)
C1 0.031(4) 0.041(6) 0.042(4) -0.001(4) 0.001(4) 0.007(4)
C2 0.043(5) 0.038(6) 0.036(4) 0.002(3) 0.010(4) -0.002(4)
C3 0.045(5) 0.039(6) 0.031(4) 0.000(3) 0.005(3) 0.005(4)
C4 0.039(4) 0.040(5) 0.041(4) -0.006(4) 0.009(4) -0.007(4)
C5 0.041(5) 0.044(5) 0.031(4) -0.007(4) 0.000(3) 0.002(4)
N1 0.038(4) 0.040(4) 0.040(4) -0.001(3) 0.004(3) -0.004(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
Cl1 C1 1.709(9) . ?
Cl2 C2 1.714(8) . ?
Cl3 C4 1.710(10) . ?
Cl4 C5 1.707(8) . ?
Cl5 C3 1.721(9) . ?
C1 N1 1.323(12) . ?
C1 C2 1.378(12) . ?
C2 C4 1.384(13) . ?
C3 N1 1.304(12) . ?
C3 C5 1.373(12) . ?
C4 C5 1.414(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.6(8) . . ?
N1 C1 Cl1 117.2(7) . . ?
C2 C1 Cl1 121.2(7) . . ?
C1 C2 C4 119.2(8) . . ?
C1 C2 Cl2 121.4(7) . . ?
C4 C2 Cl2 119.4(7) . . ?
N1 C3 C5 123.5(8) . . ?
N1 C3 Cl5 116.8(8) . . ?
C5 C3 Cl5 119.8(7) . . ?
C2 C4 C5 118.1(9) . . ?
C2 C4 Cl3 121.5(7) . . ?
C5 C4 Cl3 120.4(7) . . ?
C3 C5 C4 117.5(8) . . ?
C3 C5 Cl4 122.8(7) . . ?
C4 C5 Cl4 119.7(7) . . ?
C3 N1 C1 120.1(9) . . ?

_refine_diff_density_max         0.483
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-2

_shelx_res_file                  
;
TITL a14_94 in Pc
CELL 0.71073   5.3594   5.2238  15.1010  90.000 100.228  90.000
ZERR    2.00   0.0044   0.0042   0.0132   0.000   0.018   0.000
LATT -1
SYMM X, -Y, 0.5+Z
SFAC  C   N   CL
UNIT   10    2  10
TEMP 27
L.S. 8
BOND
ACTA
FMAP 2
PLAN -20
WGHT    0.056300
FVAR       0.91220
CL1   3    0.118458    0.670796    0.332375    11.00000    0.04955    0.06971 =
         0.04658   -0.00738   -0.00756   -0.00346
CL2   3    0.530864    1.097332    0.324778    11.00000    0.07730    0.05722 =
         0.04747    0.01786    0.01098    0.00267
CL3   3    0.958236    1.172445    0.491919    11.00000    0.05009    0.05004 =
         0.06963   -0.00792    0.01656   -0.01532
CL4   3    0.965893    0.820027    0.659562    11.00000    0.05104    0.07717 =
         0.04531   -0.00367   -0.00964    0.00031
CL5   3    0.534883    0.406184    0.653360    11.00000    0.07064    0.05787 =
         0.04416    0.01212    0.01331   -0.00097
C1    1    0.358872    0.721887    0.421301    11.00000    0.03070    0.04150 =
         0.04208   -0.00075    0.00070    0.00706
C2    1    0.539210    0.907971    0.417963    11.00000    0.04319    0.03825 =
         0.03649    0.00223    0.01040   -0.00211
C3    1    0.543317    0.605137    0.563083    11.00000    0.04528    0.03851 =
         0.03124    0.00039    0.00534    0.00479
C4    1    0.731585    0.941799    0.491296    11.00000    0.03862    0.04031 =
         0.04122   -0.00567    0.00895   -0.00667
C5    1    0.732559    0.784440    0.567505    11.00000    0.04104    0.04424 =
         0.03107   -0.00661    0.00041    0.00223
N1    2    0.363903    0.575841    0.493194    11.00000    0.03750    0.04044 =
         0.04011   -0.00122    0.00369   -0.00361
HKLF 4

REM  a14_94 in Pc
REM R1 =  0.0525 for    1172 Fo > 4sig(Fo)  and  0.1006 for all    1936 data
REM    100 parameters refined using      2 restraints

END

WGHT      0.0564      0.0000

REM Highest difference peak  0.483,  deepest hole -0.327,  1-sigma level  0.091
Q1    1   1.1414  1.3435  0.5007  11.00000  0.05    0.48
Q2    1   0.3439  0.4009  0.5188  11.00000  0.05    0.41
Q3    1   0.7600  1.1339  0.4581  11.00000  0.05    0.38
Q4    1   0.6870  0.9189  0.5455  11.00000  0.05    0.35
Q5    1   1.0643  1.0118  0.6771  11.00000  0.05    0.33
Q6    1   0.6766  0.3030  0.5989  11.00000  0.05    0.33
Q7    1   0.4201  0.6503  0.5269  11.00000  0.05    0.32
Q8    1   0.2923  0.6372  0.3786  11.00000  0.05    0.32
Q9    1   0.7036  1.0614  0.3535  11.00000  0.05    0.31
Q10   1  -0.0358  0.8446  0.3216  11.00000  0.05    0.30
Q11   1   0.8988  1.0052  0.4523  11.00000  0.05    0.30
Q12   1   0.4662  0.2891  0.6376  11.00000  0.05    0.30
Q13   1   1.0165  1.0290  0.6871  11.00000  0.05    0.30
Q14   1   0.4072  1.1834  0.3830  11.00000  0.05    0.30
Q15   1   0.3098  0.6734  0.4728  11.00000  0.05    0.30
Q16   1   0.2216  0.5760  0.2788  11.00000  0.05    0.29
Q17   1   0.4529  0.5081  0.6288  11.00000  0.05    0.29
Q18   1   0.6291  1.2321  0.3472  11.00000  0.05    0.29
Q19   1  -0.0408  0.4819  0.3270  11.00000  0.05    0.29
Q20   1   0.6476  0.8267  0.4668  11.00000  0.05    0.29
;
_shelx_res_checksum              9633
