#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546675.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_1546675
loop_
_publ_author_name
'Mohamed Abdelahi, Mohamed Mokhtar'
'Sebbar, Nada Kheira'
'Jasinski, Jerry P.'
'Kaur, Manpreet'
'Essassi, El Mokhtar'
'Benchidmi, Mohammed'
_publ_section_title
;
 3-Chloro-1-ethyl-6-nitro-1H-indazole
;
_journal_coeditor_code           HB4155
_journal_issue                   7
_journal_name_full               IUCrData
_journal_page_first              x170972
_journal_paper_doi               10.1107/S2414314617009725
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C9 H8 Cl N3 O2'
_chemical_formula_moiety         'C9 H8 Cl N3 O2'
_chemical_formula_sum            'C9 H8 Cl N3 O2'
_chemical_formula_weight         225.63
_chemical_name_systematic
;
3-Chloro-1-ethyl-6-nitro-1H-indazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.403(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4984(3)
_cell_length_b                   16.2805(7)
_cell_length_c                   8.3363(3)
_cell_measurement_reflns_used    1252
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8700
_cell_measurement_theta_min      5.9930
_cell_volume                     1009.19(7)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3567
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.390
_diffrn_reflns_theta_min         5.434
_exptl_absorpt_coefficient_mu    3.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0418
_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)+(0.0591P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                1572
_reflns_number_total             1916
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4155sup1.cif
_cod_data_source_block           I
_cod_database_code               1546675
_cod_database_fobs_code          1546675
_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           2014/6
loop_
_space_group_symop_operation_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_occupancy
Cl Cl1 0.34194(8) 0.57002(5) 0.22541(6) 0.0741(2) Uani d 1
O O1 0.0801(2) 0.38775(13) 1.0161(2) 0.0801(5) Uani d 1
O O2 0.0722(3) 0.28363(12) 0.8569(3) 0.1041(8) Uani d 1
N N1 0.3183(2) 0.63770(11) 0.5077(2) 0.0555(4) Uani d 1
N N2 0.2742(2) 0.61772(10) 0.6560(2) 0.0506(4) Uani d 1
N N3 0.0963(2) 0.35657(12) 0.8854(3) 0.0628(5) Uani d 1
C C1 0.2999(2) 0.57001(14) 0.4224(2) 0.0516(4) Uani d 1
C C2 0.2448(2) 0.50247(12) 0.5101(2) 0.0453(4) Uani d 1
C C3 0.2059(2) 0.41950(13) 0.4800(3) 0.0528(5) Uani d 1
H H3 0.2124 0.3969 0.3785 0.063 Uiso calc 1
C C4 0.1581(3) 0.37243(12) 0.6036(3) 0.0556(5) Uani d 1
H H4 0.1329 0.3169 0.5876 0.067 Uiso calc 1
C C5 0.1473(2) 0.40879(12) 0.7548(2) 0.0487(4) Uani d 1
C C6 0.1812(2) 0.48984(12) 0.7903(2) 0.0459(4) Uani d 1
H H6 0.1710 0.5121 0.8914 0.055 Uiso calc 1
C C7 0.2320(2) 0.53656(11) 0.6633(2) 0.0432(4) Uani d 1
C C8 0.3023(3) 0.67764(13) 0.7875(3) 0.0585(5) Uani d 1
H H8A 0.2237 0.6646 0.8677 0.070 Uiso calc 1
H H8B 0.2704 0.7319 0.7451 0.070 Uiso calc 1
C C9 0.4930(3) 0.67852(18) 0.8667(4) 0.0791(7) Uani d 1
H H9A 0.5700 0.6969 0.7905 0.119 Uiso calc 1
H H9B 0.5276 0.6241 0.9027 0.119 Uiso calc 1
H H9C 0.5038 0.7151 0.9577 0.119 Uiso calc 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'
O O 0.0492 0.0322 '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
C1 N1 N2 105.75(17)
N1 N2 C7 110.95(16)
N1 N2 C8 119.57(17)
C7 N2 C8 128.75(17)
O1 N3 C5 119.02(19)
O2 N3 O1 123.3(2)
O2 N3 C5 117.7(2)
N1 C1 Cl1 120.10(17)
N1 C1 C2 113.08(18)
C2 C1 Cl1 126.83(17)
C3 C2 C1 136.70(19)
C3 C2 C7 120.51(18)
C7 C2 C1 102.79(17)
C2 C3 H3 120.8
C4 C3 C2 118.32(18)
C4 C3 H3 120.8
C3 C4 H4 120.3
C3 C4 C5 119.39(18)
C5 C4 H4 120.3
C4 C5 N3 118.12(19)
C6 C5 N3 117.14(18)
C6 C5 C4 124.74(19)
C5 C6 H6 122.5
C5 C6 C7 115.00(17)
C7 C6 H6 122.5
N2 C7 C2 107.41(16)
N2 C7 C6 130.55(17)
C6 C7 C2 122.03(17)
N2 C8 H8A 109.2
N2 C8 H8B 109.2
N2 C8 C9 112.00(18)
H8A C8 H8B 107.9
C9 C8 H8A 109.2
C9 C8 H8B 109.2
C8 C9 H9A 109.5
C8 C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.712(2)
O1 N3 1.222(3)
O2 N3 1.220(3)
N1 N2 1.360(2)
N1 C1 1.309(3)
N2 C7 1.362(2)
N2 C8 1.462(3)
N3 C5 1.470(3)
C1 C2 1.411(3)
C2 C3 1.398(3)
C2 C7 1.407(2)
C3 H3 0.9300
C3 C4 1.369(3)
C4 H4 0.9300
C4 C5 1.404(3)
C5 C6 1.369(3)
C6 H6 0.9300
C6 C7 1.396(3)
C8 H8A 0.9700
C8 H8B 0.9700
C8 C9 1.496(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
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
C4 H4 O2 4_565 0.93 2.52 3.280(3) 139
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139050514
