#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/08/2230817.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_2230817
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Arshad, Suhana'
'Chandrakantha, B.'
'Isloor, Arun M.'
'Shetty, Prakash'
_publ_section_title
;
 2,6-Dichloro-3-nitropyridine
;
_journal_coeditor_code           NG5183
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1785
_journal_paper_doi               10.1107/S1600536811023683
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H2 Cl2 N2 O2'
_chemical_formula_moiety         'C5 H2 Cl2 N2 O2'
_chemical_formula_sum            'C5 H2 Cl2 N2 O2'
_chemical_formula_weight         192.99
_chemical_name_systematic
;
2,6-Dichloro-3-nitropyridine
;
_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                 122.072(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9021(8)
_cell_length_b                   19.166(2)
_cell_length_c                   11.0987(9)
_cell_measurement_reflns_used    3419
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.69
_cell_measurement_theta_min      2.41
_cell_volume                     1424.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16845
_diffrn_reflns_theta_full        31.80
_diffrn_reflns_theta_max         31.80
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  0.8214
_exptl_absorpt_correction_T_min  0.7271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0667
_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)+(0.0527P)²+1.2999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                2323
_reflns_number_total             4817
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5183.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230817
_cod_database_fobs_code          2230817
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.51344(18) 0.68002(5) 0.26085(12) 0.0667(3) Uani d . 1 1 . .
Cl Cl2A 0.49627(16) 0.91466(4) 0.03753(9) 0.0540(3) Uani d . 1 1 . .
O O1A 0.6135(4) 1.00995(14) 0.4256(3) 0.0656(8) Uani d . 1 1 . .
O O2A 0.4472(5) 1.01996(13) 0.1975(3) 0.0641(8) Uani d . 1 1 . .
N N1A 0.5042(4) 0.80475(13) 0.1709(3) 0.0411(6) Uani d . 1 1 . .
N N2A 0.5284(4) 0.98557(14) 0.3053(3) 0.0433(6) Uani d . 1 1 . .
C C1A 0.5404(5) 0.87035(18) 0.4058(3) 0.0445(8) Uani d . 1 1 . .
H H1A 0.5538 0.8926 0.4848 0.053 Uiso calc R 1 1 . .
C C2A 0.5356(5) 0.79924(18) 0.3979(4) 0.0463(8) Uani d . 1 1 . .
H H2A 0.5436 0.7720 0.4701 0.056 Uiso calc R 1 1 . .
C C3A 0.5182(5) 0.76941(15) 0.2786(3) 0.0397(7) Uani d . 1 1 . .
C C4A 0.5072(5) 0.87406(15) 0.1788(3) 0.0359(7) Uani d . 1 1 . .
C C5A 0.5251(5) 0.90936(15) 0.2945(3) 0.0351(7) Uani d . 1 1 . .
Cl Cl1B 1.01800(19) 0.67408(5) 0.25606(12) 0.0673(3) Uani d . 1 1 . .
Cl Cl2B 0.98563(15) 0.91167(5) 0.03234(9) 0.0532(3) Uani d . 1 1 . .
O O1B 0.9156(5) 1.00415(15) 0.3366(3) 0.0731(9) Uani d . 1 1 . .
O O2B 1.1216(5) 1.01192(14) 0.2658(3) 0.0663(8) Uani d . 1 1 . .
N N1B 1.0071(4) 0.79906(13) 0.1667(3) 0.0403(6) Uani d . 1 1 . .
N N2B 1.0196(5) 0.97918(15) 0.2975(3) 0.0470(7) Uani d . 1 1 . .
C C1B 1.0342(5) 0.86410(18) 0.4000(3) 0.0450(8) Uani d . 1 1 . .
H H1B 1.0422 0.8863 0.4773 0.054 Uiso calc R 1 1 . .
C C2B 1.0342(5) 0.79259(19) 0.3928(4) 0.0481(8) Uani d . 1 1 . .
H H2B 1.0421 0.7650 0.4646 0.058 Uiso calc R 1 1 . .
C C3B 1.0218(5) 0.76313(16) 0.2741(3) 0.0427(8) Uani d . 1 1 . .
C C4B 1.0086(5) 0.86795(16) 0.1754(3) 0.0356(7) Uani d . 1 1 . .
C C5B 1.0219(5) 0.90270(16) 0.2895(3) 0.0376(7) Uani d . 1 1 . .
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C4A N1A C3A . . 117.4(3) ?
O2A N2A O1A . . 124.5(3) ?
O2A N2A C5A . . 119.0(3) ?
O1A N2A C5A . . 116.5(3) ?
C2A C1A C5A . . 119.5(3) ?
C2A C1A H1A . . 120.2 ?
C5A C1A H1A . . 120.2 ?
C1A C2A C3A . . 117.4(3) ?
C1A C2A H2A . . 121.3 ?
C3A C2A H2A . . 121.3 ?
N1A C3A C2A . . 124.8(3) ?
N1A C3A Cl1A . . 114.8(2) ?
C2A C3A Cl1A . . 120.4(2) ?
N1A C4A C5A . . 122.4(3) ?
N1A C4A Cl2A . . 113.8(2) ?
C5A C4A Cl2A . . 123.8(2) ?
C1A C5A C4A . . 118.4(3) ?
C1A C5A N2A . . 118.2(3) ?
C4A C5A N2A . . 123.3(3) ?
C4B N1B C3B . . 117.3(3) ?
O2B N2B O1B . . 125.5(3) ?
O2B N2B C5B . . 117.9(3) ?
O1B N2B C5B . . 116.6(3) ?
C2B C1B C5B . . 118.8(3) ?
C2B C1B H1B . . 120.6 ?
C5B C1B H1B . . 120.6 ?
C1B C2B C3B . . 117.3(3) ?
C1B C2B H2B . . 121.4 ?
C3B C2B H2B . . 121.4 ?
N1B C3B C2B . . 124.7(3) ?
N1B C3B Cl1B . . 115.0(3) ?
C2B C3B Cl1B . . 120.2(3) ?
N1B C4B C5B . . 122.7(3) ?
N1B C4B Cl2B . . 115.3(2) ?
C5B C4B Cl2B . . 122.0(2) ?
C4B C5B C1B . . 119.1(3) ?
C4B C5B N2B . . 122.5(3) ?
C1B C5B N2B . . 118.4(3) ?
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
Cl1A C3A . 1.723(3) ?
Cl2A C4A . 1.711(3) ?
O1A N2A . 1.224(3) ?
O2A N2A . 1.209(4) ?
N1A C4A . 1.331(4) ?
N1A C3A . 1.326(4) ?
N2A C5A . 1.465(4) ?
C1A C2A . 1.365(5) ?
C1A C5A . 1.393(4) ?
C1A H1A . 0.9300 ?
C2A C3A . 1.381(5) ?
C2A H2A . 0.9300 ?
C4A C5A . 1.391(4) ?
Cl1B C3B . 1.717(3) ?
Cl2B C4B . 1.717(3) ?
O1B N2B . 1.214(4) ?
O2B N2B . 1.211(4) ?
N1B C4B . 1.323(4) ?
N1B C3B . 1.327(4) ?
N2B C5B . 1.469(4) ?
C1B C2B . 1.373(5) ?
C1B C5B . 1.391(4) ?
C1B H1B . 0.9300 ?
C2B C3B . 1.389(5) ?
C2B H2B . 0.9300 ?
C4B C5B . 1.385(4) ?
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
C5A C1A C2A C3A . . . . 0.9(5) ?
C4A N1A C3A C2A . . . . 0.0(5) ?
C4A N1A C3A Cl1A . . . . -180.0(3) ?
C1A C2A C3A N1A . . . . -0.6(6) ?
C1A C2A C3A Cl1A . . . . 179.4(3) ?
C3A N1A C4A C5A . . . . 0.3(5) ?
C3A N1A C4A Cl2A . . . . 178.0(2) ?
C2A C1A C5A C4A . . . . -0.6(5) ?
C2A C1A C5A N2A . . . . 179.3(3) ?
N1A C4A C5A C1A . . . . 0.0(5) ?
Cl2A C4A C5A C1A . . . . -177.5(3) ?
N1A C4A C5A N2A . . . . -179.9(3) ?
Cl2A C4A C5A N2A . . . . 2.6(5) ?
O2A N2A C5A C1A . . . . -153.8(3) ?
O1A N2A C5A C1A . . . . 25.6(4) ?
O2A N2A C5A C4A . . . . 26.1(5) ?
O1A N2A C5A C4A . . . . -154.5(3) ?
C5B C1B C2B C3B . . . . 0.0(5) ?
C4B N1B C3B C2B . . . . 1.5(5) ?
C4B N1B C3B Cl1B . . . . 179.7(2) ?
C1B C2B C3B N1B . . . . -1.1(6) ?
C1B C2B C3B Cl1B . . . . -179.2(3) ?
C3B N1B C4B C5B . . . . -0.9(5) ?
C3B N1B C4B Cl2B . . . . -179.1(2) ?
N1B C4B C5B C1B . . . . 0.0(5) ?
Cl2B C4B C5B C1B . . . . 178.1(3) ?
N1B C4B C5B N2B . . . . -178.8(3) ?
Cl2B C4B C5B N2B . . . . -0.7(5) ?
C2B C1B C5B C4B . . . . 0.5(5) ?
C2B C1B C5B N2B . . . . 179.3(3) ?
O2B N2B C5B C4B . . . . -44.8(5) ?
O1B N2B C5B C4B . . . . 135.7(4) ?
O2B N2B C5B C1B . . . . 136.4(3) ?
O1B N2B C5B C1B . . . . -43.0(5) ?
