#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/65/2236548.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236548
loop_
_publ_author_name
'Zhu, Xue-mei'
'Pei, Li-jun'
'Cai, Zhao-sheng'
'Song, Zhan-qian'
'Shang, Shi-bin'
_publ_section_title
;
 2,3,6-Trichloro-5-(trichloromethyl)pyridine
;
_journal_coeditor_code           PV2577
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2723
_journal_paper_doi               10.1107/S1600536812035404
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H Cl6 N'
_chemical_formula_moiety         'C6 H Cl6 N'
_chemical_formula_sum            'C6 H Cl6 N'
_chemical_formula_weight         299.78
_chemical_name_systematic
;
2,3,6-Trichloro-5-(trichloromethyl)pyridine
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3100(17)
_cell_length_b                   17.018(3)
_cell_length_c                   7.3160(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1034.6(4)
_computing_cell_refinement       'CAD4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1985
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.607
_exptl_absorpt_correction_T_max  0.7393
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.385
_refine_ls_extinction_coef       0.077(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                779
_reflns_number_total             1033
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2577.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P b c m '
_cod_database_code               2236548
_cod_database_fobs_code          2236548
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'
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_symmetry_multiplicity
N N 0.5025(5) 0.4324(2) 0.2500 0.0467(9) Uani d S 1 2
Cl Cl1 0.8417(2) 0.26884(8) 0.2500 0.0806(6) Uani d S 1 2
C C1 0.8339(6) 0.4268(3) 0.2500 0.0478(11) Uani d S 1 2
H H1A 0.9457 0.4241 0.2500 0.057 Uiso calc SR 1 2
Cl Cl2 0.45826(19) 0.28195(8) 0.2500 0.0753(5) Uani d S 1 2
C C2 0.7445(7) 0.3584(3) 0.2500 0.0537(12) Uani d S 1 2
Cl Cl3 0.47402(13) 0.58193(7) 0.2500 0.0569(4) Uani d S 1 2
C C3 0.5783(6) 0.3642(3) 0.2500 0.0486(11) Uani d S 1 2
Cl Cl4 0.81252(10) 0.63147(5) 0.05227(15) 0.0619(4) Uani d . 1 1
C C4 0.5902(5) 0.4969(2) 0.2500 0.0399(10) Uani d S 1 2
Cl Cl5 1.06686(13) 0.55710(8) 0.2500 0.0672(5) Uani d S 1 2
C C5 0.7586(5) 0.4991(2) 0.2500 0.0418(10) Uani d S 1 2
C C6 0.8554(5) 0.5748(2) 0.2500 0.0451(11) Uani d S 1 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N 0.0472(18) 0.042(2) 0.051(2) -0.0058(15) 0.000 0.000
Cl1 0.1128(13) 0.0423(7) 0.0867(11) 0.0263(7) 0.000 0.000
C1 0.051(3) 0.042(2) 0.051(3) 0.0113(19) 0.000 0.000
Cl2 0.0977(11) 0.0433(7) 0.0849(10) -0.0220(6) 0.000 0.000
C2 0.075(3) 0.042(2) 0.044(2) 0.014(2) 0.000 0.000
Cl3 0.0372(6) 0.0463(7) 0.0872(10) 0.0073(4) 0.000 0.000
C3 0.061(3) 0.043(2) 0.042(2) -0.009(2) 0.000 0.000
Cl4 0.0572(5) 0.0552(6) 0.0734(7) 0.0006(3) 0.0064(5) 0.0182(4)
C4 0.039(2) 0.034(2) 0.046(2) 0.0056(17) 0.000 0.000
Cl5 0.0334(6) 0.0666(8) 0.1018(12) 0.0007(5) 0.000 0.000
C5 0.041(2) 0.040(2) 0.044(2) -0.0008(18) 0.000 0.000
C6 0.036(2) 0.039(2) 0.061(3) 0.0008(17) 0.000 0.000
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'
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
C4 N C3 . . 118.0(4)
C2 C1 C5 . . 120.5(4)
C2 C1 H1A . . 119.7
C5 C1 H1A . . 119.7
C1 C2 C3 . . 118.4(4)
C1 C2 Cl1 . . 119.6(4)
C3 C2 Cl1 . . 122.0(4)
N C3 C2 . . 122.6(4)
N C3 Cl2 . . 116.0(4)
C2 C3 Cl2 . . 121.4(4)
N C4 C5 . . 125.1(4)
N C4 Cl3 . . 112.7(3)
C5 C4 Cl3 . . 122.2(3)
C1 C5 C4 . . 115.4(4)
C1 C5 C6 . . 121.1(4)
C4 C5 C6 . . 123.5(4)
C5 C6 Cl4 . . 110.77(18)
C5 C6 Cl4 . 6_556 110.77(18)
Cl4 C6 Cl4 . 6_556 109.2(2)
C5 C6 Cl5 . . 112.2(3)
Cl4 C6 Cl5 . . 106.84(17)
Cl4 C6 Cl5 6_556 . 106.84(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N C4 . 1.318(6)
N C3 . 1.321(6)
Cl1 C2 . 1.724(5)
C1 C2 . 1.381(7)
C1 C5 . 1.381(6)
C1 H1A . 0.9300
Cl2 C3 . 1.719(4)
C2 C3 . 1.385(8)
Cl3 C4 . 1.739(4)
Cl4 C6 . 1.774(3)
C4 C5 . 1.400(6)
Cl5 C6 . 1.783(5)
C5 C6 . 1.519(6)
C6 Cl4 6_556 1.774(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1A Cl5 0.9300 2.4800 2.944(5) 111.00
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_4
_geom_torsion
C5 C1 C2 C3 . 0.0
C5 C1 C2 Cl1 . 180.0
C4 N C3 C2 . 0.0
C4 N C3 Cl2 . 180.0
C1 C2 C3 N . 0.0
Cl1 C2 C3 N . 180.0
C1 C2 C3 Cl2 . 180.0
Cl1 C2 C3 Cl2 . 0.0
C3 N C4 C5 . 0.0
C3 N C4 Cl3 . 180.0
C2 C1 C5 C4 . 0.0
C2 C1 C5 C6 . 180.0
N C4 C5 C1 . 0.0
Cl3 C4 C5 C1 . 180.0
N C4 C5 C6 . 180.0
Cl3 C4 C5 C6 . 0.0
C1 C5 C6 Cl4 . 119.32(19)
C4 C5 C6 Cl4 . -60.68(19)
C1 C5 C6 Cl4 6_556 -119.32(19)
C4 C5 C6 Cl4 6_556 60.68(19)
C1 C5 C6 Cl5 . 0.0
C4 C5 C6 Cl5 . 180.0
