#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/17/2211775.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_2211775
loop_
_publ_author_name
'Hong-Fei Ma'
'Hong-Sheng Jia'
'Yi Qian'
'Fan Wen'
'Bin-Lin Chen'
_publ_section_title
;
 2,3,5-Trichloropyridine
;
_journal_coeditor_code           CI2251
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o311
_journal_page_last               o312
_journal_paper_doi               10.1107/S1600536806053414
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H2 Cl3 N'
_chemical_formula_moiety         'C5 H2 Cl3 N'
_chemical_formula_sum            'C5 H2 Cl3 N'
_chemical_formula_weight         182.43
_chemical_name_systematic
;
2,3,5-trichloropyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 97.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8860(8)
_cell_length_b                   16.144(3)
_cell_length_c                   10.959(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     681.5(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1525
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.240
_exptl_absorpt_correction_T_max  0.7895
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.369
_refine_ls_extinction_coef       0.050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0464
_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)+(0.075P)²+0.0336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                953
_reflns_number_total             1328
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2251.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211775
_cod_database_fobs_code          2211775
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl Cl1 0.2433(3) 0.60946(6) 0.71624(9) 0.0607(4) Uani d . 1
Cl Cl2 -0.2177(3) 0.59753(6) 0.45589(10) 0.0698(4) Uani d . 1
Cl Cl3 0.2167(3) 0.94095(6) 0.66074(11) 0.0724(4) Uani d . 1
N N -0.1957(7) 0.7573(2) 0.4531(2) 0.0534(8) Uani d . 1
C C1 -0.1042(9) 0.8319(2) 0.4980(3) 0.0523(9) Uani d . 1
H H1A -0.1811 0.8786 0.4526 0.063 Uiso calc R 1
C C2 0.1008(9) 0.8422(2) 0.6096(3) 0.0469(8) Uani d . 1
C C3 0.2108(8) 0.7740(2) 0.6793(3) 0.0449(8) Uani d . 1
H H3A 0.3476 0.7798 0.7552 0.054 Uiso calc R 1
C C4 0.1126(8) 0.6973(2) 0.6336(3) 0.0427(8) Uani d . 1
C C5 -0.0896(8) 0.6918(2) 0.5189(3) 0.0460(8) Uani d . 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
Cl1 0.0670(6) 0.0527(5) 0.0588(6) 0.0073(4) -0.0046(4) 0.0108(4)
Cl2 0.0728(7) 0.0634(6) 0.0682(7) -0.0020(5) -0.0092(5) -0.0181(5)
Cl3 0.0835(8) 0.0482(5) 0.0809(7) -0.0065(5) -0.0067(5) -0.0010(5)
N 0.0540(18) 0.0626(18) 0.0408(15) 0.0083(14) -0.0047(13) 0.0019(14)
C1 0.060(2) 0.054(2) 0.0416(16) 0.0058(17) 0.0002(16) 0.0074(16)
C2 0.0469(18) 0.0456(18) 0.0481(18) 0.0001(15) 0.0056(14) 0.0005(15)
C3 0.0421(18) 0.056(2) 0.0357(15) 0.0006(15) 0.0011(13) 0.0016(14)
C4 0.0385(17) 0.0460(17) 0.0433(17) 0.0057(14) 0.0047(14) 0.0050(14)
C5 0.0393(18) 0.0544(19) 0.0437(17) 0.0027(15) 0.0031(14) -0.0039(15)
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
_geom_angle_publ_flag
C5 N C1 118.4(3) yes
N C1 C2 122.1(3) yes
N C1 H1A 119.0 ?
C2 C1 H1A 119.0 ?
C3 C2 C1 119.8(3) ?
C3 C2 Cl3 120.6(3) yes
C1 C2 Cl3 119.6(3) yes
C4 C3 C2 118.0(3) ?
C4 C3 H3A 121.0 ?
C2 C3 H3A 121.0 ?
C3 C4 C5 118.9(3) ?
C3 C4 Cl1 120.2(2) yes
C5 C4 Cl1 120.9(3) yes
N C5 C4 122.8(3) yes
N C5 Cl2 116.0(2) yes
C4 C5 Cl2 121.2(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.722(3) yes
Cl2 C5 1.717(3) yes
Cl3 C2 1.729(4) yes
N C5 1.315(4) yes
N C1 1.332(4) yes
C1 C2 1.379(5) ?
C1 H1A 0.93 ?
C2 C3 1.375(4) ?
C3 C4 1.372(5) ?
C3 H3A 0.93 ?
C4 C5 1.394(5) ?
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
C5 N C1 C2 1.0(5)
N C1 C2 C3 -1.4(5)
N C1 C2 Cl3 178.7(3)
C1 C2 C3 C4 0.5(5)
Cl3 C2 C3 C4 -179.6(3)
C2 C3 C4 C5 0.6(5)
C2 C3 C4 Cl1 179.8(2)
C1 N C5 C4 0.3(5)
C1 N C5 Cl2 179.8(3)
C3 C4 C5 N -1.1(5)
Cl1 C4 C5 N 179.8(3)
C3 C4 C5 Cl2 179.4(2)
Cl1 C4 C5 Cl2 0.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25741
