#------------------------------------------------------------------------------
#$Date: 2021-04-23 12:55:31 +0300 (Fri, 23 Apr 2021) $
#$Revision: 264474 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022362.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_2022362
loop_
_publ_author_name
'Szczesio, Małgorzata'
'Gobis, Katarzyna'
'Korona-Głowniak, Izabela'
'Mazerant-Politowicz, Ida'
'Ziembicka, Dagmara'
'Foks, Henryk'
'Główka, Marek'
'Olczak, Andrzej'
_publ_section_title
;
 Synthesis, structure and biological activity of four new
 picolinohydrazonamide derivatives
;
_journal_coeditor_code           FM3063
_journal_issue                   7
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              673
_journal_page_last               680
_journal_paper_doi               10.1107/S2053229620007822
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C6 H7 Cl N4'
_chemical_formula_moiety         'C6 H7 Cl N4'
_chemical_formula_sum            'C6 H7 Cl N4'
_chemical_formula_weight         170.61
_chemical_name_common
;
6-Chloropicolinohydrazonamide
;
_chemical_name_systematic
;
N'-Amino-6-chloropyridine-2-carboximidamide
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   3.77379(4)
_cell_length_b                   5.63483(4)
_cell_length_c                   32.9783(2)
_cell_measurement_reflns_used    16896
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.5140
_cell_measurement_theta_min      4.0280
_cell_volume                     701.273(10)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9765
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy Dualflex Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            19459
_diffrn_reflns_theta_full        66.9682
_diffrn_reflns_theta_max         78.6751
_diffrn_reflns_theta_min         4.0214
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.264
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2019)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.217
_refine_ls_abs_structure_details
;
Flack x determined using 533 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.014(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0206
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0336P)²+0.1754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0564
_reflns_number_gt                1460
_reflns_number_total             1471
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fm3063sup1.cif
_cod_data_source_block           6
_cod_depositor_comments          'Adding Fobs data.'
_cod_database_code               2022362
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2.014
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C4 0.4858(4) 0.5683(3) 0.56871(5) 0.0101(3) Uani d 1 . .
C C41 0.3457(4) 0.4871(3) 0.60868(5) 0.0105(3) Uani d 1 . .
C C43 0.3056(4) 0.5605(3) 0.67637(5) 0.0126(3) Uani d 1 . .
C C44 0.1294(5) 0.3501(3) 0.68446(5) 0.0145(3) Uani d 1 . .
H H44 0.0606 0.3092 0.7106 0.017 Uiso calc 1 . .
C C45 0.0607(5) 0.2030(3) 0.65155(5) 0.0143(3) Uani d 1 . .
H H45 -0.0579 0.0600 0.6553 0.017 Uiso calc 1 . .
C C46 0.1700(4) 0.2708(3) 0.61310(5) 0.0125(3) Uani d 1 . .
H H46 0.1271 0.1742 0.5908 0.015 Uiso calc 1 . .
Cl Cl43 0.40807(11) 0.75195(7) 0.71649(2) 0.01704(13) Uani d 1 . .
N N2 0.5959(4) 0.5093(3) 0.50120(4) 0.0121(3) Uani d 1 . .
H H2A 0.789(6) 0.591(4) 0.5045(6) 0.015 Uiso d 1 . .
H H2B 0.651(6) 0.382(4) 0.4876(6) 0.015 Uiso d 1 . .
N N3 0.4582(4) 0.4232(2) 0.53853(4) 0.0110(3) Uani d 1 . .
N N4 0.6340(4) 0.7887(2) 0.56824(4) 0.0137(3) Uani d 1 . .
H H4A 0.764(6) 0.841(4) 0.5478(6) 0.016 Uiso d 1 . .
H H4B 0.658(6) 0.847(4) 0.5915(7) 0.016 Uiso d 1 . .
N N42 0.4116(4) 0.6328(2) 0.64006(4) 0.0118(3) 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
N3 C4 N4 . . 126.95(15)
N3 C4 C41 . . 117.23(14)
N4 C4 C41 . . 115.81(14)
N42 C41 C46 . . 122.76(15)
N42 C41 C4 . . 115.28(14)
C46 C41 C4 . . 121.92(14)
N42 C43 C44 . . 125.55(15)
N42 C43 Cl43 . . 115.23(13)
C44 C43 Cl43 . . 119.21(12)
C43 C44 C45 . . 116.72(15)
C43 C44 H44 . . 121.6
C45 C44 H44 . . 121.6
C46 C45 C44 . . 119.62(16)
C46 C45 H45 . . 120.2
C44 C45 H45 . . 120.2
C45 C46 C41 . . 118.51(16)
C45 C46 H46 . . 120.7
C41 C46 H46 . . 120.7
N3 N2 H2A . . 112.3(13)
N3 N2 H2B . . 104.6(14)
H2A N2 H2B . . 108(2)
C4 N3 N2 . . 114.95(13)
C4 N4 H4A . . 122.5(14)
C4 N4 H4B . . 113.0(15)
H4A N4 H4B . . 121(2)
C43 N42 C41 . . 116.83(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C4 N3 . 1.292(2)
C4 N4 . 1.362(2)
C4 C41 . 1.492(2)
C41 N42 . 1.344(2)
C41 C46 . 1.395(2)
C43 N42 . 1.327(2)
C43 C44 . 1.385(3)
C43 Cl43 . 1.7506(16)
C44 C45 . 1.390(2)
C44 H44 . 0.9300
C45 C46 . 1.387(2)
C45 H45 . 0.9300
C46 H46 . 0.9300
N2 N3 . 1.4216(17)
N2 H2A . 0.87(2)
N2 H2B . 0.87(2)
N4 H4A . 0.88(2)
N4 H4B . 0.84(2)
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
N4 H4B N42 . 0.84(2) 2.21(2) 2.662(2) 113.8(19)
N4 H4A N2 4_566 0.88(2) 2.21(2) 3.095(2) 176.4(19)
N2 H2B N3 4_556 0.87(2) 2.25(2) 3.0862(19) 162(2)
N2 H2A N2 4_566 0.87(2) 2.54(2) 3.306(2) 147.5(19)
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
N3 C4 C41 N42 . . . . 173.55(15)
N4 C4 C41 N42 . . . . -5.7(2)
N3 C4 C41 C46 . . . . -4.3(2)
N4 C4 C41 C46 . . . . 176.46(15)
N42 C43 C44 C45 . . . . 0.3(3)
Cl43 C43 C44 C45 . . . . -178.87(13)
C43 C44 C45 C46 . . . . 0.3(2)
C44 C45 C46 C41 . . . . -0.3(2)
N42 C41 C46 C45 . . . . -0.4(3)
C4 C41 C46 C45 . . . . 177.31(15)
N4 C4 N3 N2 . . . . -0.8(2)
C41 C4 N3 N2 . . . . -179.96(14)
C44 C43 N42 C41 . . . . -1.0(3)
Cl43 C43 N42 C41 . . . . 178.26(12)
C46 C41 N42 C43 . . . . 1.0(2)
C4 C41 N42 C43 . . . . -176.86(14)

_cod_database_fobs_code 2022362
