#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242122.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_2242122
loop_
_publ_author_name
'Sulovari, Aron'
'Tanski, Joseph M.'
_publ_section_title
;
 Crystallographic and spectroscopic characterization of
 5-chloropyridine-2,3-diamine
;
_journal_coeditor_code           FY2122
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1213
_journal_page_last               1217
_journal_paper_doi               10.1107/S2056989017010489
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C5 H6 Cl N3'
_chemical_formula_moiety         'C5 H6 Cl N3'
_chemical_formula_sum            'C5 H6 Cl N3'
_chemical_formula_weight         143.58
_chemical_name_systematic
;
5-Chloropyridine-2,3-diamine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.7565(8)
_cell_length_b                   8.7002(17)
_cell_length_c                   18.350(4)
_cell_measurement_reflns_used    4306
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      29.7262
_cell_measurement_theta_min      2.5909
_cell_volume                     599.7(2)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009) and Mercury
(Macrae et al.,  2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0874
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14989
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.383
_refine_ls_abs_structure_details
;
Flack x determined using 511 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0308P)²+0.2158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                1477
_reflns_number_total             1845
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fy2122sup1.cif
_cod_data_source_block           I
_cod_database_code               2242122
_cod_database_fobs_code          2242122
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_occupancy
Cl Cl1 0.5035(2) 0.46707(8) 0.47194(3) 0.01872(16) Uani d 1
N N1 0.8538(6) 0.4647(3) 0.67658(12) 0.0148(5) Uani d 1
N N2 0.5894(7) 0.8717(3) 0.67694(14) 0.0153(5) Uani d 1
H H11 0.464(9) 0.928(3) 0.6466(14) 0.018 Uiso d 1
H H12 0.530(10) 0.872(3) 0.7224(12) 0.018 Uiso d 1
N N3 0.8976(7) 0.6490(3) 0.76777(13) 0.0154(5) Uani d 1
H H21 1.032(9) 0.580(3) 0.7905(15) 0.018 Uiso d 1
H H22 0.955(10) 0.748(3) 0.7772(16) 0.018 Uiso d 1
C C1 0.7608(8) 0.4231(3) 0.60820(16) 0.0157(6) Uani d 1
H H1 0.7977 0.3199 0.5931 0.019 Uiso calc 1
C C2 0.6148(7) 0.5258(4) 0.56011(14) 0.0138(5) Uani d 1
C C3 0.5497(7) 0.6759(3) 0.58152(14) 0.0121(6) Uani d 1
H H3 0.445 0.747 0.5486 0.015 Uiso calc 1
C C4 0.6388(7) 0.7209(3) 0.65122(15) 0.0122(6) Uani d 1
C C5 0.8035(7) 0.6100(3) 0.69716(15) 0.0125(6) Uani 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'
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
C5 N1 C1 118.7(3)
C4 N2 H11 112.(2)
C4 N2 H12 111.(2)
H11 N2 H12 118.(3)
C5 N3 H21 115.(2)
C5 N3 H22 118.(2)
H21 N3 H22 114.(3)
N1 C1 C2 121.8(3)
N1 C1 H1 119.1
C2 C1 H1 119.1
C1 C2 C3 120.2(3)
C1 C2 Cl1 120.1(2)
C3 C2 Cl1 119.7(2)
C4 C3 C2 119.2(3)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 N2 123.0(3)
C3 C4 C5 117.5(3)
N2 C4 C5 119.4(3)
N1 C5 N3 117.5(3)
N1 C5 C4 122.5(2)
N3 C5 C4 119.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.748(3)
N1 C5 1.333(4)
N1 C1 1.352(4)
N2 C4 1.406(4)
N2 H11 0.88(2)
N2 H12 0.86(2)
N3 C5 1.385(4)
N3 H21 0.89(2)
N3 H22 0.90(2)
C1 C2 1.371(4)
C1 H1 0.95
C2 C3 1.385(4)
C3 C4 1.379(4)
C3 H3 0.95
C4 C5 1.423(4)
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
N2 H12 N1 3_656 0.86(2) 2.48(3) 3.264(3) 151.(3) y
N3 H21 N2 3_746 0.89(2) 2.38(2) 3.250(4) 166.(3) y
N3 H22 N1 3_756 0.90(2) 2.19(2) 3.075(4) 167.(3) y
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 N1 C1 C2 -0.5(4)
N1 C1 C2 C3 -1.7(4)
N1 C1 C2 Cl1 179.3(2)
C1 C2 C3 C4 1.0(4)
Cl1 C2 C3 C4 -180.0(2)
C2 C3 C4 N2 178.5(3)
C2 C3 C4 C5 1.7(4)
C1 N1 C5 N3 179.3(2)
C1 N1 C5 C4 3.3(4)
C3 C4 C5 N1 -4.0(4)
N2 C4 C5 N1 179.0(3)
C3 C4 C5 N3 -179.8(3)
N2 C4 C5 N3 3.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 1268254
