#------------------------------------------------------------------------------
#$Date: 2024-04-06 02:41:39 +0300 (Sat, 06 Apr 2024) $
#$Revision: 291112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023036.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_2023036
loop_
_publ_author_name
'Dhote, Pawan'
'Tothadi, Srinu'
'Ramana, Chepuri V.'
_publ_section_title
;
 Synthesis, characterization, and crystal structure of
 2-(2-azido-phen-yl)-3-oxo-3H-indole 1-oxide.
;
_journal_coeditor_code           DX2056
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              310
_journal_page_last               313
_journal_paper_doi               10.1107/S2056989024001440
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C14 H8 N4 O2'
_chemical_formula_moiety         'C14 H8 N4 O2'
_chemical_formula_sum            'C14 H8 N4 O2'
_chemical_formula_weight         264.24
_chemical_name_systematic
;
2-(2-Azidophenyl)-3-oxo-3H-indole 1-oxide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                95.473(16)
_cell_angle_beta                 105.226(12)
_cell_angle_gamma                113.116(13)
_cell_formula_units_Z            2
_cell_length_a                   7.166(2)
_cell_length_b                   7.686(3)
_cell_length_c                   12.172(4)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.56
_cell_measurement_theta_min      3.10
_cell_volume                     579.9(3)
_computing_cell_refinement
;
SAINT v8.37A (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT v8.37A (Bruker, 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
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            45548
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.205
_diffrn_reflns_theta_min         2.956
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0422
_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)+(0.0660P)²+0.1514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                3946
_reflns_number_total             4818
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dx2056sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023036.cif.'
_cod_database_code               2023036
_cod_database_fobs_code          2023036
_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   0.987
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O O1 0.67828(11) -0.03978(9) 0.35537(6) 0.01840(14) Uani d 1 . .
O O2 0.33615(11) 0.29764(9) 0.15423(6) 0.01970(14) Uani d 1 . .
N N4 1.05131(16) 0.87935(13) 0.27516(9) 0.02787(19) Uani d 1 . .
N N2 0.81071(12) 0.56952(10) 0.28504(6) 0.01489(14) Uani d 1 . .
N N3 0.93852(12) 0.73575(11) 0.28689(7) 0.01669(14) Uani d 1 . .
C C10 0.77636(12) 0.53396(11) 0.39246(7) 0.01172(14) Uani d 1 . .
C C9 0.64747(12) 0.34085(11) 0.39218(7) 0.01194(14) Uani d 1 . .
C C8 0.54989(12) 0.18621(11) 0.28650(7) 0.01240(14) Uani d 1 . .
N N1A 0.40687(13) 0.17681(11) 0.17988(8) 0.01765(16) Uani d 0.5 A 1
C C14 0.34033(13) -0.00926(12) 0.09961(7) 0.01469(15) Uani d 1 . .
C C2 0.20365(14) -0.08622(14) -0.01379(8) 0.01915(17) Uani d 1 . .
H H2 0.134768 -0.017372 -0.055149 0.023 Uiso calc 1 . .
C C3 0.17122(15) -0.27158(15) -0.06522(8) 0.02109(18) Uani d 1 . .
H H3 0.077902 -0.330058 -0.143374 0.025 Uiso calc 1 . .
C C11 0.86772(13) 0.67870(12) 0.49428(7) 0.01393(15) Uani d 1 . .
H H11 0.955317 0.808707 0.493893 0.017 Uiso calc 1 . .
C C12 0.83019(14) 0.63213(13) 0.59624(7) 0.01570(15) Uani d 1 . .
H H12 0.891796 0.730900 0.665580 0.019 Uiso calc 1 . .
C C13 0.70271(14) 0.44142(13) 0.59774(7) 0.01594(15) Uani d 1 . .
H H13 0.677285 0.410403 0.667753 0.019 Uiso calc 1 . .
C C15 0.61299(13) 0.29688(12) 0.49620(7) 0.01451(15) Uani d 1 . .
H H15 0.527337 0.166823 0.497471 0.017 Uiso calc 1 . .
C C17 0.57040(12) 0.01171(11) 0.27811(7) 0.01585(15) Uani d 0.5 A 1
C C6 0.44015(13) -0.11001(12) 0.16023(7) 0.01356(14) Uani d 1 . .
C C5 0.41071(14) -0.29159(12) 0.11154(8) 0.01623(15) Uani d 1 . .
H H5 0.479954 -0.359268 0.153933 0.019 Uiso calc 1 . .
C C4 0.27263(15) -0.37139(13) -0.00430(8) 0.01966(17) Uani d 1 . .
H H4 0.247984 -0.496292 -0.041850 0.024 Uiso calc 1 . .
C C1B 0.40687(13) 0.17681(11) 0.17988(8) 0.01765(16) Uani d 0.5 A 2
N N17A 0.57040(12) 0.01171(11) 0.27811(7) 0.01585(15) Uani d 0.5 A 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 N2 C10 . . 116.77(7) ?
N4 N3 N2 . . 171.89(9) ?
C9 C10 N2 . . 116.31(7) ?
C11 C10 N2 . . 123.03(8) ?
C11 C10 C9 . . 120.64(8) ?
C10 C9 C8 . . 121.71(7) ?
C15 C9 C10 . . 118.70(7) ?
C15 C9 C8 . . 119.59(7) ?
N1A C8 C9 . . 126.97(7) ?
N1A C8 C17 . . 107.79(7) ?
C17 C8 C9 . . 125.04(7) ?
C1B C8 C9 . . 126.97(7) ?
C1B C8 N17A . . 107.79(7) ?
N17A C8 C9 . . 125.04(7) ?
O2 N1A C8 . . 127.81(8) ?
O2 N1A C14 . . 123.50(8) ?
C8 N1A C14 . . 108.64(7) ?
C2 C14 N1A . . 131.01(8) ?
C2 C14 C6 . . 121.74(8) ?
C2 C14 C1B . . 131.01(8) ?
C6 C14 N1A . . 107.23(8) ?
C6 C14 C1B . . 107.23(8) ?
C14 C2 H2 . . 121.7 ?
C14 C2 C3 . . 116.59(8) ?
C3 C2 H2 . . 121.7 ?
C2 C3 H3 . . 119.3 ?
C4 C3 C2 . . 121.42(8) ?
C4 C3 H3 . . 119.3 ?
C10 C11 H11 . . 120.1 ?
C12 C11 C10 . . 119.71(8) ?
C12 C11 H11 . . 120.1 ?
C11 C12 H12 . . 119.7 ?
C11 C12 C13 . . 120.52(8) ?
C13 C12 H12 . . 119.7 ?
C12 C13 H13 . . 120.2 ?
C15 C13 C12 . . 119.67(8) ?
C15 C13 H13 . . 120.2 ?
C9 C15 H15 . . 119.6 ?
C13 C15 C9 . . 120.76(8) ?
C13 C15 H15 . . 119.6 ?
O1 C17 C8 . . 127.91(8) ?
O1 C17 C6 . . 123.29(8) ?
C8 C17 C6 . . 108.80(7) ?
C14 C6 C17 . . 107.50(7) ?
C14 C6 N17A . . 107.50(7) ?
C5 C6 C14 . . 122.61(8) ?
C5 C6 C17 . . 129.89(8) ?
C5 C6 N17A . . 129.89(8) ?
C6 C5 H5 . . 121.9 ?
C6 C5 C4 . . 116.25(8) ?
C4 C5 H5 . . 121.9 ?
C3 C4 C5 . . 121.38(8) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
O2 C1B C8 . . 127.81(8) ?
O2 C1B C14 . . 123.50(8) ?
C8 C1B C14 . . 108.64(7) ?
O1 N17A C8 . . 127.91(8) ?
O1 N17A C6 . . 123.29(8) ?
C8 N17A C6 . . 108.80(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C17 . 1.2523(11) ?
O1 N17A . 1.2523(11) ?
O2 N1A . 1.2485(11) ?
O2 C1B . 1.2485(11) ?
N4 N3 . 1.1323(12) ?
N2 N3 . 1.2396(11) ?
N2 C10 . 1.4245(11) ?
C10 C9 . 1.4061(12) ?
C10 C11 . 1.3933(12) ?
C9 C8 . 1.4628(12) ?
C9 C15 . 1.3996(12) ?
C8 N1A . 1.4019(13) ?
C8 C17 . 1.4028(12) ?
C8 C1B . 1.4019(13) ?
C8 N17A . 1.4028(12) ?
N1A C14 . 1.4767(12) ?
C14 C2 . 1.3762(13) ?
C14 C6 . 1.3865(12) ?
C14 C1B . 1.4767(12) ?
C2 H2 . 0.9500 ?
C2 C3 . 1.4033(15) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.3892(14) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.3876(12) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.3950(13) ?
C13 H13 . 0.9500 ?
C13 C15 . 1.3911(12) ?
C15 H15 . 0.9500 ?
C17 C6 . 1.4697(12) ?
C6 C5 . 1.3744(12) ?
C6 N17A . 1.4697(12) ?
C5 H5 . 0.9500 ?
C5 C4 . 1.4033(13) ?
C4 H4 . 0.9500 ?
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
C5 H5 O2 1_545 0.95 2.43 3.1077(16) 128
C11 H11 O1 2_766 0.95 2.57 3.2327(17) 127
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
_geom_torsion_publ_flag
O1 C17 C6 C14 . . . . 178.78(8) ?
O1 C17 C6 C5 . . . . -0.58(14) ?
O2 N1A C14 C2 . . . . 2.51(14) ?
O2 N1A C14 C6 . . . . -176.07(8) ?
N2 C10 C9 C8 . . . . -1.48(11) ?
N2 C10 C9 C15 . . . . 178.39(7) ?
N2 C10 C11 C12 . . . . -178.73(7) ?
N3 N2 C10 C9 . . . . -174.08(7) ?
N3 N2 C10 C11 . . . . 4.34(12) ?
C10 C9 C8 N1A . . . . -59.12(12) ?
C10 C9 C8 C17 . . . . 126.65(9) ?
C10 C9 C8 C1B . . . . -59.12(12) ?
C10 C9 C8 N17A . . . . 126.65(9) ?
C10 C9 C15 C13 . . . . 0.57(12) ?
C10 C11 C12 C13 . . . . 0.35(12) ?
C9 C10 C11 C12 . . . . -0.38(12) ?
C9 C8 N1A O2 . . . . 0.35(14) ?
C9 C8 N1A C14 . . . . -177.02(7) ?
C9 C8 C17 O1 . . . . -2.70(13) ?
C9 C8 C17 C6 . . . . 176.94(7) ?
C9 C8 C1B O2 . . . . 0.35(14) ?
C9 C8 C1B C14 . . . . -177.02(7) ?
C9 C8 N17A O1 . . . . -2.70(13) ?
C9 C8 N17A C6 . . . . 176.94(7) ?
C8 C9 C15 C13 . . . . -179.56(7) ?
C8 N1A C14 C2 . . . . -179.99(9) ?
C8 N1A C14 C6 . . . . 1.43(9) ?
C8 C17 C6 C14 . . . . -0.88(9) ?
C8 C17 C6 C5 . . . . 179.76(8) ?
N1A C8 C17 O1 . . . . -177.87(8) ?
N1A C8 C17 C6 . . . . 1.78(9) ?
N1A C14 C2 C3 . . . . -178.72(8) ?
N1A C14 C6 C17 . . . . -0.32(9) ?
N1A C14 C6 C5 . . . . 179.09(7) ?
C14 C2 C3 C4 . . . . -0.07(13) ?
C14 C6 C5 C4 . . . . 0.01(12) ?
C14 C6 N17A O1 . . . . 178.78(8) ?
C14 C6 N17A C8 . . . . -0.88(9) ?
C2 C14 C6 C17 . . . . -179.07(7) ?
C2 C14 C6 C5 . . . . 0.35(13) ?
C2 C14 C6 N17A . . . . -179.07(7) ?
C2 C14 C1B O2 . . . . 2.51(14) ?
C2 C14 C1B C8 . . . . -179.99(9) ?
C2 C3 C4 C5 . . . . 0.43(14) ?
C11 C10 C9 C8 . . . . -179.94(7) ?
C11 C10 C9 C15 . . . . -0.08(11) ?
C11 C12 C13 C15 . . . . 0.14(13) ?
C12 C13 C15 C9 . . . . -0.61(12) ?
C15 C9 C8 N1A . . . . 121.02(9) ?
C15 C9 C8 C17 . . . . -53.22(11) ?
C15 C9 C8 C1B . . . . 121.02(9) ?
C15 C9 C8 N17A . . . . -53.22(11) ?
C17 C8 N1A O2 . . . . 175.39(8) ?
C17 C8 N1A C14 . . . . -1.97(9) ?
C17 C6 C5 C4 . . . . 179.29(8) ?
C6 C14 C2 C3 . . . . -0.31(13) ?
C6 C14 C1B O2 . . . . -176.07(8) ?
C6 C14 C1B C8 . . . . 1.43(9) ?
C6 C5 C4 C3 . . . . -0.39(13) ?
C5 C6 N17A O1 . . . . -0.58(14) ?
C5 C6 N17A C8 . . . . 179.76(8) ?
C1B C8 N17A O1 . . . . -177.87(8) ?
C1B C8 N17A C6 . . . . 1.78(9) ?
C1B C14 C2 C3 . . . . -178.72(8) ?
C1B C14 C6 C5 . . . . 179.09(7) ?
C1B C14 C6 N17A . . . . -0.32(9) ?
N17A C8 C1B O2 . . . . 175.39(8) ?
N17A C8 C1B C14 . . . . -1.97(9) ?
N17A C6 C5 C4 . . . . 179.29(8) ?
