#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/08/2220873.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_2220873
loop_
_publ_author_name
'Hua, Yu-Peng'
'Xu, Ying'
'Wei, Xue-Hong'
'Tong, Hong-Bo'
_publ_section_title
;
 2-Chloropyridine-3-carboxamide
;
_journal_coeditor_code           NC2131
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o373
_journal_paper_doi               10.1107/S1600536809002256
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H5 Cl N2 O'
_chemical_formula_moiety         'C6 H5 Cl N2 O'
_chemical_formula_sum            'C6 H5 Cl N2 O'
_chemical_formula_weight         156.57
_chemical_name_common            2-Chloronicotinamide
_chemical_name_systematic
;
2-Chloropyridine-3-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.82(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.980(5)
_cell_length_b                   13.627(9)
_cell_length_c                   7.108(5)
_cell_measurement_reflns_used    1764
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.86
_cell_volume                     675.7(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_max  0.9090
_exptl_absorpt_correction_T_min  0.8678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.234
_refine_ls_extinction_coef       0.051(8)
_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   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0551P)²+0.1035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                1083
_reflns_number_total             1188
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2131.cif
_cod_data_source_block           I
_cod_original_cell_volume        675.8(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220873
_cod_database_fobs_code          2220873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.14993(7) 0.10791(4) 0.88571(7) 0.0533(2) Uani d . 1 . .
C C1 0.3716(2) 0.07827(13) 0.7965(2) 0.0349(4) Uani d . 1 . .
N N1 0.4064(2) -0.01655(11) 0.7824(2) 0.0446(4) Uani d . 1 . .
O O 0.5546(2) 0.30761(9) 0.8932(2) 0.0507(4) Uani d . 1 . .
C C6 0.4574(2) 0.25974(12) 0.7786(2) 0.0351(4) Uani d . 1 . .
N N2 0.3180(2) 0.29749(11) 0.6708(2) 0.0446(4) Uani d . 1 . .
H H2A 0.2909 0.3589 0.6786 0.054 Uiso calc R 1 . .
H H2B 0.2545 0.2606 0.5930 0.054 Uiso calc R 1 . .
C C3 0.6760(3) 0.12278(14) 0.6910(3) 0.0430(5) Uani d . 1 . .
H H3 0.7681 0.1692 0.6616 0.052 Uiso calc R 1 . .
C C4 0.7153(3) 0.02376(16) 0.6735(3) 0.0505(5) Uani d . 1 . .
H H4 0.8331 0.0026 0.6312 0.061 Uiso calc R 1 . .
C C2 0.4989(2) 0.15240(12) 0.7524(2) 0.0325(4) Uani d . 1 . .
C C5 0.5774(3) -0.04231(14) 0.7198(3) 0.0506(6) Uani d . 1 . .
H H5 0.6042 -0.1088 0.7071 0.061 Uiso calc R 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
Cl 0.0357(3) 0.0599(4) 0.0647(4) -0.0034(2) 0.0066(2) 0.0116(2)
C1 0.0347(9) 0.0346(9) 0.0350(9) -0.0023(7) -0.0060(7) 0.0017(7)
N1 0.0541(10) 0.0302(8) 0.0485(9) -0.0029(7) -0.0125(8) 0.0009(6)
O 0.0548(9) 0.0356(7) 0.0603(9) -0.0041(6) -0.0181(7) -0.0060(6)
C6 0.0333(9) 0.0319(9) 0.0399(9) -0.0025(7) -0.0003(7) 0.0020(7)
N2 0.0456(9) 0.0300(8) 0.0573(10) 0.0039(6) -0.0124(8) -0.0020(7)
C3 0.0336(10) 0.0493(12) 0.0460(10) 0.0009(8) -0.0022(8) -0.0017(8)
C4 0.0431(11) 0.0566(13) 0.0512(12) 0.0162(9) -0.0069(9) -0.0109(9)
C2 0.0298(9) 0.0335(9) 0.0337(9) 0.0002(7) -0.0051(7) -0.0002(7)
C5 0.0649(14) 0.0346(10) 0.0509(11) 0.0130(9) -0.0191(10) -0.0081(8)
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
N1 C1 C2 . . 125.08(18) ?
N1 C1 Cl . . 115.07(14) ?
C2 C1 Cl . . 119.80(14) ?
C1 N1 C5 . . 116.88(16) ?
O C6 N2 . . 123.86(17) ?
O C6 C2 . . 119.55(15) ?
N2 C6 C2 . . 116.57(15) ?
C6 N2 H2A . . 120.0 ?
C6 N2 H2B . . 120.0 ?
H2A N2 H2B . . 120.0 ?
C4 C3 C2 . . 119.63(19) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C5 C4 C3 . . 118.6(2) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 120.7 ?
C3 C2 C1 . . 116.34(17) ?
C3 C2 C6 . . 120.00(16) ?
C1 C2 C6 . . 123.56(16) ?
N1 C5 C4 . . 123.49(18) ?
N1 C5 H5 . . 118.3 ?
C4 C5 H5 . . 118.3 ?
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
Cl C1 . 1.738(2) ?
C1 N1 . 1.319(2) ?
C1 C2 . 1.388(3) ?
N1 C5 . 1.334(3) ?
O C6 . 1.230(2) ?
C6 N2 . 1.324(2) ?
C6 C2 . 1.504(3) ?
N2 H2A . 0.8600 ?
N2 H2B . 0.8600 ?
C3 C4 . 1.383(3) ?
C3 C2 . 1.385(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.366(3) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A N1 2_556 0.86 2.21 3.003(3) 153.5
N2 H2B O 4_565 0.86 2.17 3.015(3) 168.4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 74530
