#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/36/1543621.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_1543621
loop_
_publ_author_name
'Rejouani, Fatima-Zahra'
'Mojahidi, Souad'
'Rakib, El Mostapha'
'Mdeghri Alaoui, Abdelouahed'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 Ethyl 2-(6-nitro-2H-indazol-2-yl)acetate
;
_journal_coeditor_code           TK4019
_journal_issue                   7
_journal_name_full               IUCrData
_journal_page_first              x161074
_journal_paper_doi               10.1107/S2414314616010749
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C11 H11 N3 O4'
_chemical_formula_moiety         'C11 H11 N3 O4'
_chemical_formula_sum            'C11 H11 N3 O4'
_chemical_formula_weight         249.23
_chemical_melting_point          338
_chemical_name_systematic
;
Ethyl 2-(6-nitro-2H-indazol-2-yl)acetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 122.839(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.808(3)
_cell_length_b                   4.6312(4)
_cell_length_c                   19.0381(16)
_cell_measurement_reflns_used    3324
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.572
_cell_measurement_theta_min      2.144
_cell_volume                     2356.3(4)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEX'
_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  0.0298
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25389
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.572
_diffrn_reflns_theta_min         2.144
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2015b)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0444
_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)+(0.0714P)²+0.8343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                2517
_reflns_number_total             3324
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tk4019sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2356.3(3)
_cod_database_code               1543621
_cod_database_fobs_code          1543621
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C C1 0.33711(5) 0.4119(3) 0.46597(8) 0.0418(3) Uani d 1
C C2 0.37402(5) 0.6087(3) 0.52132(8) 0.0466(3) Uani d 1
H H2 0.3723 0.7029 0.5628 0.056 Uiso calc 1
C C3 0.41254(5) 0.6530(3) 0.51054(8) 0.0472(3) Uani d 1
C C4 0.41682(5) 0.5172(4) 0.44835(10) 0.0570(4) Uani d 1
H H4 0.4443 0.5553 0.4447 0.068 Uiso calc 1
C C5 0.38093(6) 0.3310(4) 0.39402(10) 0.0580(4) Uani d 1
H H5 0.3831 0.2427 0.3522 0.070 Uiso calc 1
C C6 0.34001(5) 0.2737(3) 0.40226(8) 0.0454(3) Uani d 1
C C7 0.29814(5) 0.0965(3) 0.36243(9) 0.0508(3) Uani d 1
H H7 0.2884 -0.0244 0.3171 0.061 Uiso calc 1
C C8 0.22800(5) 0.0023(3) 0.38266(9) 0.0516(3) Uani d 1
H H8A 0.2282 -0.0198 0.4335 0.062 Uiso calc 1
H H8B 0.2252 -0.1883 0.3594 0.062 Uiso calc 1
C C9 0.18351(5) 0.1819(3) 0.32093(8) 0.0432(3) Uani d 1
C C10 0.09600(6) 0.2351(4) 0.25660(11) 0.0614(4) Uani d 1
H H10A 0.0955 0.4089 0.2845 0.074 Uiso calc 1
H H10B 0.0940 0.2908 0.2058 0.074 Uiso calc 1
C C11 0.05359(6) 0.0510(5) 0.23640(13) 0.0792(6) Uani d 1
H H11A 0.0230 0.1540 0.2005 0.119 Uiso calc 1
H H11B 0.0542 -0.1199 0.2084 0.119 Uiso calc 1
H H11C 0.0557 -0.0022 0.2870 0.119 Uiso calc 1
N N1 0.45222(5) 0.8546(3) 0.56789(8) 0.0608(3) Uani d 1
N N2 0.29646(4) 0.3270(3) 0.46565(7) 0.0482(3) Uani d 1
N N3 0.27453(4) 0.1349(2) 0.40251(7) 0.0467(3) Uani d 1
O O1 0.48852(5) 0.8813(4) 0.56230(9) 0.0909(5) Uani d 1
O O2 0.44763(5) 0.9839(4) 0.61888(9) 0.0884(4) Uani d 1
O O3 0.18539(4) 0.3901(2) 0.28551(7) 0.0644(3) Uani d 1
O O4 0.14227(3) 0.0744(2) 0.31126(6) 0.0532(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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 C2 126.96(11)
N2 C1 C6 111.80(11)
C2 C1 C6 121.23(11)
C3 C2 C1 115.98(12)
C3 C2 H2 122.0
C1 C2 H2 122.0
C2 C3 C4 124.25(13)
C2 C3 N1 117.61(13)
C4 C3 N1 118.14(12)
C5 C4 C3 119.96(12)
C5 C4 H4 120.0
C3 C4 H4 120.0
C4 C5 C6 118.62(13)
C4 C5 H5 120.7
C6 C5 H5 120.7
C7 C6 C5 135.79(13)
C7 C6 C1 104.23(11)
C5 C6 C1 119.96(12)
N3 C7 C6 106.16(12)
N3 C7 H7 126.9
C6 C7 H7 126.9
N3 C8 C9 111.32(11)
N3 C8 H8A 109.4
C9 C8 H8A 109.4
N3 C8 H8B 109.4
C9 C8 H8B 109.4
H8A C8 H8B 108.0
O3 C9 O4 125.13(13)
O3 C9 C8 124.84(12)
O4 C9 C8 110.03(11)
C11 C10 O4 108.64(13)
C11 C10 H10A 110.0
O4 C10 H10A 110.0
C11 C10 H10B 110.0
O4 C10 H10B 110.0
H10A C10 H10B 108.3
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O2 N1 O1 123.26(14)
O2 N1 C3 118.66(12)
O1 N1 C3 118.08(15)
N3 N2 C1 103.17(10)
C7 N3 N2 114.63(11)
C7 N3 C8 127.07(12)
N2 N3 C8 118.25(11)
C9 O4 C10 116.59(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.3485(15)
C1 C2 1.4062(18)
C1 C6 1.4182(17)
C2 C3 1.3631(17)
C2 H2 0.9300
C3 C4 1.411(2)
C3 N1 1.4703(18)
C4 C5 1.355(2)
C4 H4 0.9300
C5 C6 1.4177(18)
C5 H5 0.9300
C6 C7 1.3881(18)
C7 N3 1.3411(17)
C7 H7 0.9300
C8 N3 1.4504(16)
C8 C9 1.5073(19)
C8 H8A 0.9700
C8 H8B 0.9700
C9 O3 1.1964(16)
C9 O4 1.3195(15)
C10 C11 1.460(2)
C10 O4 1.4634(17)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
N1 O2 1.2150(19)
N1 O1 1.2218(17)
N2 N3 1.3468(16)
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
C7 H7 O3 4_545 0.93 2.54 3.2743(18) 137
C8 H8A N2 7_556 0.97 2.59 3.4650(19) 149
C8 H8B O3 1_545 0.97 2.34 3.2525(18) 157
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139048819
