#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/78/7127825.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7127825
loop_
_publ_author_name
'Gogoi, Kongkona'
'Bora, Bidisha R.'
'Borah, Geetika'
'Sarma, Bipul'
'Gogoi, Sanjib'
_publ_section_title
;
 Synthesis of quaternary carbon-centered
 indolo[1,2-a]quinazolinones and indazolo[1,2-a]indazolones
 via C-H functionalization.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1388
_journal_page_last               1391
_journal_paper_doi               10.1039/d0cc07419e
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-11 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.502(13)
_cell_angle_beta                 107.431(13)
_cell_angle_gamma                91.458(14)
_cell_formula_units_Z            2
_cell_length_a                   8.213(10)
_cell_length_b                   9.582(12)
_cell_length_c                   11.527(14)
_cell_measurement_reflns_used    4839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.60
_cell_volume                     865.1(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28815
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.990
_diffrn_reflns_theta_min         1.852
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0491
_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)+(0.1000P)²+0.0596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3142
_reflns_number_total             4523
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc07419e2.cif
_cod_data_source_block           BS_KGH_24_1_0m
_cod_depositor_comments
'Adding full bibliography for 7127823--7127825.cif.'
_cod_original_cell_volume        865.1(19)
_cod_database_code               7127825
_shelx_shelxl_version_number     2014/7
_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   0.978
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05512(15) 0.84427(11) 0.59252(9) 0.0414(3) Uani 1 1 d . . . . .
N1 N 0.02042(16) 0.85920(12) 0.39124(11) 0.0328(3) Uani 1 1 d . . . . .
N2 N 0.07257(17) 0.66409(12) 0.27935(11) 0.0359(3) Uani 1 1 d . . . . .
C3 C 0.16026(18) 0.66075(14) 0.49681(13) 0.0327(3) Uani 1 1 d . . . . .
C2 C 0.07666(18) 0.79561(14) 0.49879(13) 0.0313(3) Uani 1 1 d . . . . .
C18 C 0.25358(18) 0.87751(14) 0.29599(12) 0.0321(3) Uani 1 1 d . . . . .
C1 C 0.07511(18) 0.81668(14) 0.28681(12) 0.0314(3) Uani 1 1 d . . . . .
C15 C -0.05836(19) 0.85762(16) 0.16858(13) 0.0353(3) Uani 1 1 d . . . . .
C4 C 0.14923(19) 0.59359(14) 0.38647(14) 0.0347(3) Uani 1 1 d . . . . .
C5 C 0.2419(2) 0.59745(16) 0.60619(15) 0.0421(4) Uani 1 1 d . . . . .
H5 H 0.2511 0.6433 0.6794 0.051 Uiso 1 1 calc R U . . .
C23 C 0.3625(2) 0.80553(16) 0.24823(14) 0.0402(4) Uani 1 1 d . . . . .
H23 H 0.3321 0.7156 0.2170 0.048 Uiso 1 1 calc R U . . .
C14 C -0.1290(2) 0.72760(18) 0.10438(14) 0.0419(4) Uani 1 1 d . . . . .
C9 C -0.0526(2) 0.61537(16) 0.17453(13) 0.0385(3) Uani 1 1 d . . . . .
C8 C 0.2192(2) 0.46167(16) 0.38780(16) 0.0460(4) Uani 1 1 d . . . . .
H8 H 0.2139 0.4158 0.3153 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2962(2) 0.40050(17) 0.49777(18) 0.0530(5) Uani 1 1 d . . . . .
H7 H 0.3404 0.3120 0.4984 0.064 Uiso 1 1 calc R U . . .
C19 C 0.3025(2) 1.01026(17) 0.34419(17) 0.0484(4) Uani 1 1 d . . . . .
H19 H 0.2321 1.0593 0.3790 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3093(2) 0.46683(18) 0.60644(17) 0.0527(4) Uani 1 1 d . . . . .
H6 H 0.3632 0.4242 0.6796 0.063 Uiso 1 1 calc R U . . .
C22 C 0.5167(2) 0.8655(2) 0.24625(17) 0.0510(4) Uani 1 1 d . . . . .
H22 H 0.5895 0.8158 0.2142 0.061 Uiso 1 1 calc R U . . .
C10 C -0.1019(3) 0.47821(19) 0.13792(17) 0.0539(5) Uani 1 1 d . . . . .
H10 H -0.0515 0.4036 0.1851 0.065 Uiso 1 1 calc R U . . .
C21 C 0.5623(2) 0.9989(2) 0.29182(18) 0.0558(5) Uani 1 1 d . . . . .
H21 H 0.6649 1.0402 0.2893 0.067 Uiso 1 1 calc R U . . .
C16 C -0.0948(2) 0.99016(18) 0.14219(16) 0.0496(4) Uani 1 1 d . . . . .
H16 H -0.0305 1.0570 0.1971 0.060 Uiso 1 1 calc R U . . .
C20 C 0.4561(3) 1.0702(2) 0.3407(2) 0.0616(5) Uani 1 1 d . . . . .
H20 H 0.4873 1.1600 0.3721 0.074 Uiso 1 1 calc R U . . .
C13 C -0.2548(3) 0.7011(2) -0.00618(18) 0.0622(5) Uani 1 1 d . . . . .
H13 H -0.3054 0.7746 -0.0547 0.075 Uiso 1 1 calc R U . . .
C11 C -0.2292(3) 0.4568(2) 0.0281(2) 0.0750(7) Uani 1 1 d . . . . .
H11 H -0.2651 0.3659 0.0020 0.090 Uiso 1 1 calc R U . . .
C17 C -0.2265(3) 1.0432(3) 0.0351(2) 0.0789(7) Uani 1 1 d . . . . .
H17A H -0.1982 1.0196 -0.0375 0.118 Uiso 1 1 calc R U . . .
H17B H -0.2309 1.1428 0.0422 0.118 Uiso 1 1 calc R U . . .
H17C H -0.3357 1.0017 0.0311 0.118 Uiso 1 1 calc R U . . .
C12 C -0.3035(3) 0.5653(3) -0.0428(2) 0.0797(7) Uani 1 1 d . . . . .
H12 H -0.3876 0.5472 -0.1163 0.096 Uiso 1 1 calc R U . . .
H1A H -0.024(2) 0.950(2) 0.3859(17) 0.056(5) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 121.48(14) . . ?
C2 N1 H1A 121.1(12) . . ?
C1 N1 H1A 114.3(11) . . ?
C4 N2 C9 128.98(14) . . ?
C4 N2 C1 117.11(12) . . ?
C9 N2 C1 110.59(12) . . ?
C5 C3 C4 120.08(16) . . ?
C5 C3 C2 119.26(14) . . ?
C4 C3 C2 120.57(13) . . ?
O1 C2 N1 122.11(15) . . ?
O1 C2 C3 122.14(13) . . ?
N1 C2 C3 115.72(13) . . ?
C23 C18 C19 118.78(15) . . ?
C23 C18 C1 120.67(15) . . ?
C19 C18 C1 120.37(13) . . ?
N2 C1 N1 108.93(11) . . ?
N2 C1 C15 103.62(12) . . ?
N1 C1 C15 109.80(14) . . ?
N2 C1 C18 110.76(12) . . ?
N1 C1 C18 111.46(12) . . ?
C15 C1 C18 111.97(13) . . ?
C16 C15 C14 131.67(17) . . ?
C16 C15 C1 121.80(14) . . ?
C14 C15 C1 106.50(14) . . ?
N2 C4 C3 117.84(15) . . ?
N2 C4 C8 122.96(15) . . ?
C3 C4 C8 119.17(14) . . ?
C6 C5 C3 120.26(16) . . ?
C6 C5 H5 119.9 . . ?
C3 C5 H5 119.9 . . ?
C18 C23 C22 120.78(17) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C13 C14 C9 119.17(18) . . ?
C13 C14 C15 131.81(17) . . ?
C9 C14 C15 108.99(16) . . ?
C10 C9 C14 121.40(17) . . ?
C10 C9 N2 128.45(15) . . ?
C14 C9 N2 110.15(15) . . ?
C7 C8 C4 119.32(16) . . ?
C7 C8 H8 120.3 . . ?
C4 C8 H8 120.3 . . ?
C6 C7 C8 121.73(17) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C18 C19 C20 120.12(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C7 C6 C5 119.41(16) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C21 C22 C23 119.93(16) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C11 C10 C9 117.42(18) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
C20 C21 C22 119.66(17) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C15 C16 C17 127.20(19) . . ?
C15 C16 H16 116.4 . . ?
C17 C16 H16 116.4 . . ?
C21 C20 C19 120.70(19) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C12 C11 C10 122.0(2) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.235(2) . ?
N1 C2 1.344(2) . ?
N1 C1 1.463(2) . ?
N1 H1A 0.94(2) . ?
N2 C4 1.396(2) . ?
N2 C9 1.399(2) . ?
N2 C1 1.463(2) . ?
C3 C5 1.391(2) . ?
C3 C4 1.398(3) . ?
C3 C2 1.482(2) . ?
C18 C23 1.378(2) . ?
C18 C19 1.384(3) . ?
C18 C1 1.537(3) . ?
C1 C15 1.533(2) . ?
C15 C16 1.329(3) . ?
C15 C14 1.458(3) . ?
C4 C8 1.400(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C23 C22 1.384(3) . ?
C23 H23 0.9300 . ?
C14 C13 1.396(3) . ?
C14 C9 1.396(3) . ?
C9 C10 1.389(3) . ?
C8 C7 1.379(3) . ?
C8 H8 0.9300 . ?
C7 C6 1.373(3) . ?
C7 H7 0.9300 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9300 . ?
C6 H6 0.9300 . ?
C22 C21 1.377(3) . ?
C22 H22 0.9300 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9300 . ?
C21 C20 1.365(3) . ?
C21 H21 0.9300 . ?
C16 C17 1.480(3) . ?
C16 H16 0.9300 . ?
C20 H20 0.9300 . ?
C13 C12 1.376(3) . ?
C13 H13 0.9300 . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C12 H12 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352524
