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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546683.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_1546683
loop_
_publ_author_name
'Mohamed Abdelahi, Mohamed Mokhtar'
'El Bakri, Youness'
'Minnih, Mohamed Said'
'Benchidmi, Mohammed'
'Essassi, El Mokhtar'
'Mague, Joel T.'
_publ_section_title
;
 3-Chloro-2-ethyl-6-nitro-2H-indazole
;
_journal_coeditor_code           SJ4109
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x170652
_journal_paper_doi               10.1107/S2414314617006526
_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-2-ethyl-6-nitro-2H-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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.0510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2363(7)
_cell_length_b                   7.4063(5)
_cell_length_c                   12.1247(8)
_cell_measurement_reflns_used    8820
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.0838
_cell_measurement_theta_min      3.2875
_cell_volume                     941.67(11)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17539
_diffrn_reflns_theta_full        29.150
_diffrn_reflns_theta_max         29.169
_diffrn_reflns_theta_min         1.942
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0361
_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)+(0.0702P)²+0.0386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                2183
_reflns_number_total             2543
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj4109sup1.cif
_cod_data_source_block           I
_cod_database_code               1546683
_cod_database_fobs_code          1546683
_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.
;
_shelx_estimated_absorpt_t_min   0.881
_shelx_estimated_absorpt_t_max   0.942
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 0.74446(3) 0.21393(4) 0.48713(3) 0.02049(12) Uani d 1
O O1 0.24410(9) 0.46570(14) 0.76126(8) 0.0248(2) Uani d 1
O O2 0.13166(8) 0.34576(15) 0.59292(8) 0.0278(2) Uani d 1
N N1 0.68668(9) 0.49160(14) 0.73487(9) 0.0163(2) Uani d 1
N N2 0.75445(9) 0.42256(14) 0.67233(9) 0.0164(2) Uani d 1
N N3 0.23394(9) 0.39466(14) 0.66663(9) 0.0183(2) Uani d 1
C C1 0.56070(11) 0.31391(15) 0.58095(10) 0.0139(2) Uani d 1
C C2 0.44490(11) 0.23172(16) 0.50971(10) 0.0156(2) Uani d 1
H H2 0.4420(13) 0.161(2) 0.4443(13) 0.016(3) Uiso d 1
C C3 0.33951(11) 0.26044(16) 0.53900(11) 0.0162(2) Uani d 1
H H3 0.2548(13) 0.211(2) 0.4925(12) 0.017(4) Uiso d 1
C C4 0.34978(10) 0.36817(16) 0.63905(10) 0.0148(2) Uani d 1
C C5 0.45943(11) 0.45167(16) 0.70990(10) 0.0144(2) Uani d 1
H H5 0.4606(15) 0.530(2) 0.7734(14) 0.024(4) Uiso d 1
C C6 0.56820(11) 0.42364(15) 0.67937(10) 0.0138(2) Uani d 1
C C7 0.68450(11) 0.31794(16) 0.58110(10) 0.0155(2) Uani d 1
C C8 0.89008(11) 0.4693(2) 0.70924(12) 0.0224(3) Uani d 1
H H8A 0.8929(17) 0.595(3) 0.7003(16) 0.040(5) Uiso d 1
H H8B 0.9192(16) 0.408(2) 0.6562(15) 0.032(4) Uiso d 1
C C9 0.96158(12) 0.4151(2) 0.83598(12) 0.0252(3) Uani d 1
H H9A 1.0501(16) 0.443(2) 0.8538(14) 0.028(4) Uiso d 1
H H9B 0.9544(18) 0.279(3) 0.8467(18) 0.042(5) Uiso d 1
H H9C 0.9260(16) 0.479(2) 0.8872(15) 0.030(4) 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
N2 N1 C6 103.39(9)
C7 N2 N1 113.42(9)
C7 N2 C8 128.42(10)
N1 N2 C8 118.16(10)
O1 N3 O2 123.60(10)
O1 N3 C4 118.47(10)
O2 N3 C4 117.93(10)
C7 C1 C2 135.24(11)
C7 C1 C6 103.24(10)
C2 C1 C6 121.52(10)
C3 C2 C1 117.78(11)
C3 C2 H2 122.2(9)
C1 C2 H2 120.0(9)
C2 C3 C4 119.72(11)
C2 C3 H3 122.7(8)
C4 C3 H3 117.5(8)
C5 C4 C3 124.56(11)
C5 C4 N3 117.89(10)
C3 C4 N3 117.54(10)
C4 C5 C6 115.90(11)
C4 C5 H5 121.7(10)
C6 C5 H5 122.3(10)
N1 C6 C5 127.09(11)
N1 C6 C1 112.40(10)
C5 C6 C1 120.51(10)
N2 C7 C1 107.55(10)
N2 C7 Cl1 123.72(9)
C1 C7 Cl1 128.73(10)
N2 C8 C9 111.24(10)
N2 C8 H8A 105.9(11)
C9 C8 H8A 110.6(11)
N2 C8 H8B 104.9(10)
C9 C8 H8B 112.3(10)
H8A C8 H8B 111.6(16)
C8 C9 H9A 107.5(10)
C8 C9 H9B 110.7(11)
H9A C9 H9B 107.7(14)
C8 C9 H9C 109.4(10)
H9A C9 H9C 112.6(14)
H9B C9 H9C 109.0(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.7021(12)
O1 N3 1.2297(13)
O2 N3 1.2299(13)
N1 N2 1.3532(14)
N1 C6 1.3545(14)
N2 C7 1.3480(15)
N2 C8 1.4672(15)
N3 C4 1.4687(15)
C1 C7 1.3907(16)
C1 C2 1.4151(16)
C1 C6 1.4210(15)
C2 C3 1.3696(17)
C2 H2 0.942(15)
C3 C4 1.4216(17)
C3 H3 0.986(14)
C4 C5 1.3704(16)
C5 C6 1.4138(16)
C5 H5 0.961(16)
C8 C9 1.5102(19)
C8 H8A 0.94(2)
C8 H8B 0.938(18)
C9 H9A 0.961(17)
C9 H9B 1.03(2)
C9 H9C 0.972(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
C8 H8B Cl1 . 0.938(18) 2.689(17) 3.2158(15) 116.3(12)
C5 H5 Cg2 2_656 0.961(16) 2.698(15) 3.5418(13) 147.0(10)
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
C6 N1 N2 C7 0.66(13)
C6 N1 N2 C8 -179.85(10)
C7 C1 C2 C3 179.92(13)
C6 C1 C2 C3 -0.35(17)
C1 C2 C3 C4 -0.73(17)
C2 C3 C4 C5 1.40(19)
C2 C3 C4 N3 -179.97(10)
O1 N3 C4 C5 -11.20(16)
O2 N3 C4 C5 168.15(11)
O1 N3 C4 C3 170.07(11)
O2 N3 C4 C3 -10.58(16)
C3 C4 C5 C6 -0.82(18)
N3 C4 C5 C6 -179.46(10)
N2 N1 C6 C5 179.15(11)
N2 N1 C6 C1 -0.82(13)
C4 C5 C6 N1 179.72(11)
C4 C5 C6 C1 -0.31(16)
C7 C1 C6 N1 0.68(13)
C2 C1 C6 N1 -179.12(10)
C7 C1 C6 C5 -179.29(10)
C2 C1 C6 C5 0.91(17)
N1 N2 C7 C1 -0.26(14)
C8 N2 C7 C1 -179.68(12)
N1 N2 C7 Cl1 179.83(8)
C8 N2 C7 Cl1 0.40(18)
C2 C1 C7 N2 179.52(13)
C6 C1 C7 N2 -0.25(12)
C2 C1 C7 Cl1 -0.6(2)
C6 C1 C7 Cl1 179.66(9)
C7 N2 C8 C9 -122.97(13)
N1 N2 C8 C9 57.62(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139050520
