#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/54/2225405.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_2225405
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-5-chloropyridine--benzoic acid (1/1)
;
_journal_coeditor_code           WN2376
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o578
_journal_paper_doi               10.1107/S1600536810004447
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C5 H5 Cl N2, C7 H6 O2'
_chemical_formula_moiety         'C5 H5 Cl N2, C7 H6 O2'
_chemical_formula_sum            'C12 H11 Cl N2 O2'
_chemical_formula_weight         250.68
_chemical_name_systematic
;
2-Amino-5-chloropyridine--benzoic acid (1/1)
;
_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                 100.161(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.6114(19)
_cell_length_b                   5.3442(6)
_cell_length_c                   12.4774(13)
_cell_measurement_reflns_used    5100
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.35
_cell_volume                     1155.9(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      100.00(10)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Bruker SMART APEX DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11852
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         1.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.9785
_exptl_absorpt_correction_T_min  0.8436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.2767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                2802
_reflns_number_total             3331
_reflns_threshold_expression     >2(I)
_cod_data_source_file            wn2376.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_hbond_publ_flag' value 'Yes' changed to 'yes'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_hbond_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225405
_cod_database_fobs_code          2225405
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.029115(18) 0.29660(7) 0.17435(3) 0.02611(11) Uani d . 1 . .
N N1 0.17431(6) -0.2004(2) 0.08617(9) 0.0197(2) Uani d . 1 . .
N N2 0.22948(8) -0.2526(3) -0.06737(10) 0.0270(3) Uani d . 1 . .
C C1 0.12668(7) -0.0733(2) 0.14079(10) 0.0202(2) Uani d . 1 . .
C C2 0.08720(7) 0.1356(2) 0.09858(10) 0.0203(2) Uani d . 1 . .
C C3 0.09605(8) 0.2235(3) -0.00426(11) 0.0232(3) Uani d . 1 . .
C C4 0.14399(8) 0.0960(3) -0.06017(11) 0.0229(3) Uani d . 1 . .
C C5 0.18308(7) -0.1193(2) -0.01300(10) 0.0199(2) Uani d . 1 . .
O O1 0.30023(6) 0.33873(19) 0.06701(7) 0.0235(2) Uani d . 1 . .
O O2 0.25316(5) 0.46305(18) 0.21358(7) 0.0202(2) Uani d . 1 . .
C C6 0.35843(7) 0.1449(3) 0.34708(10) 0.0194(2) Uani d . 1 . .
C C7 0.40642(7) -0.0304(3) 0.40807(10) 0.0226(3) Uani d . 1 . .
C C8 0.44122(8) -0.2180(3) 0.35634(12) 0.0232(3) Uani d . 1 . .
C C9 0.42870(8) -0.2295(3) 0.24289(12) 0.0227(3) Uani d . 1 . .
C C10 0.38163(7) -0.0544(2) 0.18193(10) 0.0202(2) Uani d . 1 . .
C C11 0.34623(7) 0.1339(2) 0.23375(10) 0.0170(2) Uani d . 1 . .
C C12 0.29775(7) 0.3214(2) 0.16423(10) 0.0173(2) Uani d . 1 . .
H H1 0.1213(10) -0.132(3) 0.2126(14) 0.028(4) Uiso d . 1 . .
H H3 0.0695(11) 0.375(4) -0.0377(16) 0.040(5) Uiso d . 1 . .
H H4 0.1539(10) 0.154(4) -0.1271(15) 0.032(5) Uiso d . 1 . .
H H6 0.3370(10) 0.270(4) 0.3810(14) 0.026(4) Uiso d . 1 . .
H H7 0.4150(10) -0.018(4) 0.4848(14) 0.032(5) Uiso d . 1 . .
H H8 0.4762(10) -0.344(3) 0.4016(14) 0.026(4) Uiso d . 1 . .
H H9 0.4506(10) -0.362(3) 0.2061(14) 0.029(4) Uiso d . 1 . .
H H10 0.3722(9) -0.058(3) 0.1028(13) 0.024(4) Uiso d . 1 . .
H H1O2 0.2262(13) 0.590(5) 0.1647(19) 0.061(7) Uiso d . 1 . .
H H1N2 0.2563(11) -0.378(4) -0.0353(16) 0.039(5) Uiso d . 1 . .
H H2N2 0.2443(11) -0.186(4) -0.1250(16) 0.033(5) Uiso d . 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
C5 N1 C1 . . 118.92(11) ?
C5 N2 H1N2 . . 120.0(13) ?
C5 N2 H2N2 . . 119.3(13) ?
H1N2 N2 H2N2 . . 117.8(18) ?
N1 C1 C2 . . 122.21(12) ?
N1 C1 H1 . . 118.2(11) ?
C2 C1 H1 . . 119.5(11) ?
C1 C2 C3 . . 119.61(12) ?
C1 C2 Cl1 . . 120.10(10) ?
C3 C2 Cl1 . . 120.25(10) ?
C4 C3 C2 . . 118.61(12) ?
C4 C3 H3 . . 118.7(11) ?
C2 C3 H3 . . 122.6(11) ?
C3 C4 C5 . . 119.45(12) ?
C3 C4 H4 . . 121.2(11) ?
C5 C4 H4 . . 119.3(11) ?
N1 C5 N2 . . 117.98(12) ?
N1 C5 C4 . . 121.20(12) ?
N2 C5 C4 . . 120.81(12) ?
C12 O2 H1O2 . . 111.7(14) ?
C11 C6 C7 . . 119.69(12) ?
C11 C6 H6 . . 120.1(11) ?
C7 C6 H6 . . 120.1(11) ?
C8 C7 C6 . . 120.33(12) ?
C8 C7 H7 . . 120.9(11) ?
C6 C7 H7 . . 118.7(11) ?
C7 C8 C9 . . 119.92(12) ?
C7 C8 H8 . . 119.6(10) ?
C9 C8 H8 . . 120.5(10) ?
C10 C9 C8 . . 119.96(12) ?
C10 C9 H9 . . 119.2(11) ?
C8 C9 H9 . . 120.8(11) ?
C9 C10 C11 . . 120.26(12) ?
C9 C10 H10 . . 121.5(10) ?
C11 C10 H10 . . 118.3(10) ?
C6 C11 C10 . . 119.82(12) ?
C6 C11 C12 . . 122.12(11) ?
C10 C11 C12 . . 118.04(11) ?
O1 C12 O2 . . 123.17(11) ?
O1 C12 C11 . . 120.66(11) ?
O2 C12 C11 . . 116.17(10) ?
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
Cl1 C2 . 1.7382(13) ?
N1 C5 . 1.3454(16) ?
N1 C1 . 1.3532(17) ?
N2 C5 . 1.3530(18) ?
N2 H1N2 . 0.88(2) ?
N2 H2N2 . 0.881(19) ?
C1 C2 . 1.3705(18) ?
C1 H1 . 0.970(18) ?
C2 C3 . 1.4006(19) ?
C3 C4 . 1.368(2) ?
C3 H3 . 0.99(2) ?
C4 C5 . 1.4149(18) ?
C4 H4 . 0.936(18) ?
O1 C12 . 1.2250(15) ?
O2 C12 . 1.3190(15) ?
O2 H1O2 . 0.98(2) ?
C6 C11 . 1.3936(17) ?
C6 C7 . 1.3946(18) ?
C6 H6 . 0.907(18) ?
C7 C8 . 1.392(2) ?
C7 H7 . 0.945(17) ?
C8 C9 . 1.395(2) ?
C8 H8 . 1.015(18) ?
C9 C10 . 1.3854(19) ?
C9 H9 . 0.962(18) ?
C10 C11 . 1.4005(18) ?
C10 H10 . 0.972(16) ?
C11 C12 . 1.4913(17) ?
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
_geom_hbond_publ_flag
O2 H1O2 N1 1_565 0.98(2) 1.65(2) 2.6290(10) 175(2) yes
N2 H1N2 O1 1_545 0.88(2) 2.04(2) 2.898(2) 165.4(18) yes
N2 H2N2 O2 4_565 0.88(2) 2.37(2) 3.231(2) 165.8(17) yes
C3 H3 Cl1 3_565 0.99(2) 2.82(2) 3.780(2) 163.4(16) yes
C6 H6 O1 4_566 0.91(2) 2.58(2) 3.095(2) 116.3(15) yes
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
C5 N1 C1 C2 . . . . -0.16(19) ?
N1 C1 C2 C3 . . . . -0.2(2) ?
N1 C1 C2 Cl1 . . . . -178.03(10) ?
C1 C2 C3 C4 . . . . 0.34(19) ?
Cl1 C2 C3 C4 . . . . 178.12(10) ?
C2 C3 C4 C5 . . . . -0.04(19) ?
C1 N1 C5 N2 . . . . -178.39(12) ?
C1 N1 C5 C4 . . . . 0.47(19) ?
C3 C4 C5 N1 . . . . -0.37(19) ?
C3 C4 C5 N2 . . . . 178.46(13) ?
C11 C6 C7 C8 . . . . -0.9(2) ?
C6 C7 C8 C9 . . . . 0.6(2) ?
C7 C8 C9 C10 . . . . 0.0(2) ?
C8 C9 C10 C11 . . . . -0.3(2) ?
C7 C6 C11 C10 . . . . 0.60(19) ?
C7 C6 C11 C12 . . . . -177.84(11) ?
C9 C10 C11 C6 . . . . -0.01(19) ?
C9 C10 C11 C12 . . . . 178.49(11) ?
C6 C11 C12 O1 . . . . 165.21(12) ?
C10 C11 C12 O1 . . . . -13.25(18) ?
C6 C11 C12 O2 . . . . -14.87(17) ?
C10 C11 C12 O2 . . . . 166.67(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656039
