#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/78/7127824.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_7127824
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            'C21 H21 Cl N2 O2'
_chemical_formula_weight         368.85
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-08-24 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.966(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.104(6)
_cell_length_b                   12.445(8)
_cell_length_c                   15.461(10)
_cell_measurement_reflns_used    3478
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.33
_cell_measurement_theta_min      2.63
_cell_volume                     1909(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.974
_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  0.1005
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            59131
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.428
_diffrn_reflns_theta_min         2.053
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.1565
_refine_ls_R_factor_gt           0.0702
_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+0.0437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2349
_reflns_number_total             5147
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc07419e2.cif
_cod_data_source_block           BS_NS_KGH_81_0m
_cod_depositor_comments
'Adding full bibliography for 7127823--7127825.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7127824
_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   0.942
_shelx_estimated_absorpt_t_max   0.976
_exptl_absorpt_special_details   SADABS
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_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
Cl1 Cl 0.63977(8) 0.47718(6) 0.21279(6) 0.0846(3) Uani 1 1 d . . . . .
O2 O 0.92369(19) -0.15308(16) 0.22406(16) 0.0889(7) Uani 1 1 d . . . . .
N4 N 0.6443(2) 0.01198(18) 0.17321(19) 0.0779(8) Uani 1 1 d . . . . .
N3 N 0.7791(2) -0.01008(18) 0.21133(18) 0.0778(8) Uani 1 1 d . . . . .
C22 C 0.6861(3) -0.1591(2) 0.14851(18) 0.0592(7) Uani 1 1 d . . . . .
C27 C 0.5890(2) -0.0788(2) 0.13377(17) 0.0571(7) Uani 1 1 d . . . . .
C21 C 0.8114(3) -0.1134(2) 0.1980(2) 0.0684(8) Uani 1 1 d . . . . .
C26 C 0.4598(3) -0.0988(2) 0.08596(18) 0.0650(7) Uani 1 1 d . . . . .
H26 H 0.3952 -0.0448 0.0747 0.078 Uiso 1 1 calc R U . . .
C23 C 0.6549(3) -0.2621(2) 0.1179(2) 0.0717(8) Uani 1 1 d . . . . .
H23 H 0.7192 -0.3165 0.1282 0.086 Uiso 1 1 calc R U . . .
C25 C 0.4329(3) -0.2010(2) 0.05655(19) 0.0731(8) Uani 1 1 d . . . . .
H25 H 0.3475 -0.2170 0.0248 0.088 Uiso 1 1 calc R U . . .
C24 C 0.5287(3) -0.2825(3) 0.0723(2) 0.0802(9) Uani 1 1 d . . . . .
H24 H 0.5061 -0.3515 0.0515 0.096 Uiso 1 1 calc R U . . .
C31 C 0.6347(3) 0.3379(2) 0.20170(17) 0.0601(7) Uani 1 1 d . . . . .
C30 C 0.7504(3) 0.2796(2) 0.23088(18) 0.0621(7) Uani 1 1 d . . . . .
H30 H 0.8302 0.3132 0.2571 0.075 Uiso 1 1 calc R U . . .
C28 C 0.8511(3) 0.0864(2) 0.2496(2) 0.0706(8) Uani 1 1 d . . . . .
C32 C 0.5152(3) 0.2901(2) 0.16400(19) 0.0650(7) Uani 1 1 d . . . . .
H32 H 0.4386 0.3321 0.1471 0.078 Uiso 1 1 calc R U . . .
C34 C 0.6238(2) 0.1215(2) 0.17826(18) 0.0598(7) Uani 1 1 d . . . . .
C29 C 0.7438(2) 0.1702(2) 0.21989(17) 0.0600(7) Uani 1 1 d . . . . .
C33 C 0.5074(3) 0.1802(2) 0.15089(19) 0.0639(7) Uani 1 1 d . . . . .
H33 H 0.4271 0.1472 0.1248 0.077 Uiso 1 1 calc R U . . .
C35 C 0.8826(3) 0.0744(3) 0.3507(2) 0.0892(10) Uani 1 1 d . . . . .
H35A H 0.9483 0.0173 0.3659 0.107 Uiso 1 1 calc R U . . .
H35B H 0.9242 0.1404 0.3759 0.107 Uiso 1 1 calc R U . . .
C36 C 0.9787(3) 0.1033(2) 0.2148(3) 0.0823(10) Uani 1 1 d . . . . .
H36A H 1.0224 0.1672 0.2427 0.099 Uiso 1 1 calc R U . . .
H36B H 1.0381 0.0432 0.2340 0.099 Uiso 1 1 calc R U . . .
C37 C 0.7634(4) 0.0502(4) 0.3934(3) 0.1124(13) Uani 1 1 d . . . . .
H37A H 0.7238 -0.0171 0.3696 0.135 Uiso 1 1 calc R U . . .
H37B H 0.6964 0.1059 0.3764 0.135 Uiso 1 1 calc R U . . .
C38 C 0.7925(5) 0.0420(4) 0.4934(3) 0.1416(18) Uani 1 1 d . . . . .
H38A H 0.8463 -0.0206 0.5111 0.212 Uiso 1 1 calc R U . . .
H38B H 0.7091 0.0366 0.5142 0.212 Uiso 1 1 calc R U . . .
H38C H 0.8404 0.1049 0.5179 0.212 Uiso 1 1 calc R U . . .
O3 O 0.8612(3) 0.1048(3) 0.06801(19) 0.1364(12) Uani 1 1 d . . . . .
C41 C 0.9688(4) 0.1148(3) 0.1215(4) 0.1060(13) Uani 1 1 d . . . . .
C42 C 1.0966(6) 0.1380(6) 0.0880(5) 0.197(3) Uani 1 1 d . . . . .
H42A H 1.1573 0.1730 0.1359 0.236 Uiso 1 1 calc R U . . .
H42B H 1.1365 0.0688 0.0794 0.236 Uiso 1 1 calc R U . . .
C43 C 1.1002(8) 0.1907(8) 0.0218(6) 0.292(6) Uani 1 1 d . . . . .
H43A H 1.0112 0.1954 -0.0134 0.437 Uiso 1 1 calc R U . . .
H43B H 1.1593 0.1565 -0.0116 0.437 Uiso 1 1 calc R U . . .
H43C H 1.1329 0.2616 0.0384 0.437 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 N4 C34 142.7(2) . . ?
C27 N4 N3 108.1(2) . . ?
C34 N4 N3 108.2(2) . . ?
C21 N3 N4 111.4(2) . . ?
C21 N3 C28 136.3(2) . . ?
N4 N3 C28 112.1(2) . . ?
C23 C22 C27 120.2(2) . . ?
C23 C22 C21 131.2(3) . . ?
C27 C22 C21 108.6(2) . . ?
N4 C27 C22 108.0(2) . . ?
N4 C27 C26 130.7(2) . . ?
C22 C27 C26 121.3(2) . . ?
O2 C21 N3 124.5(2) . . ?
O2 C21 C22 131.7(3) . . ?
N3 C21 C22 103.8(2) . . ?
C25 C26 C27 116.8(3) . . ?
C25 C26 H26 121.6 . . ?
C27 C26 H26 121.6 . . ?
C24 C23 C22 118.8(3) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C26 C25 C24 122.4(3) . . ?
C26 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C32 C31 C30 122.3(3) . . ?
C32 C31 Cl1 118.7(2) . . ?
C30 C31 Cl1 119.0(2) . . ?
C29 C30 C31 117.6(2) . . ?
C29 C30 H30 121.2 . . ?
C31 C30 H30 121.2 . . ?
N3 C28 C36 111.4(3) . . ?
N3 C28 C29 99.8(2) . . ?
C36 C28 C29 114.2(2) . . ?
N3 C28 C35 108.6(2) . . ?
C36 C28 C35 110.5(2) . . ?
C29 C28 C35 111.8(2) . . ?
C31 C32 C33 120.8(2) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C33 C34 N4 129.1(2) . . ?
C33 C34 C29 121.7(3) . . ?
N4 C34 C29 109.1(2) . . ?
C30 C29 C34 120.3(2) . . ?
C30 C29 C28 129.2(2) . . ?
C34 C29 C28 110.5(2) . . ?
C32 C33 C34 117.1(3) . . ?
C32 C33 H33 121.4 . . ?
C34 C33 H33 121.4 . . ?
C37 C35 C28 115.7(3) . . ?
C37 C35 H35A 108.3 . . ?
C28 C35 H35A 108.3 . . ?
C37 C35 H35B 108.3 . . ?
C28 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
C41 C36 C28 118.2(3) . . ?
C41 C36 H36A 107.8 . . ?
C28 C36 H36A 107.8 . . ?
C41 C36 H36B 107.8 . . ?
C28 C36 H36B 107.8 . . ?
H36A C36 H36B 107.1 . . ?
C35 C37 C38 116.2(3) . . ?
C35 C37 H37A 108.2 . . ?
C38 C37 H37A 108.2 . . ?
C35 C37 H37B 108.2 . . ?
C38 C37 H37B 108.2 . . ?
H37A C37 H37B 107.4 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O3 C41 C36 123.0(3) . . ?
O3 C41 C42 119.3(5) . . ?
C36 C41 C42 117.7(5) . . ?
C43 C42 C41 123.7(7) . . ?
C43 C42 H42A 106.4 . . ?
C41 C42 H42A 106.4 . . ?
C43 C42 H42B 106.4 . . ?
C41 C42 H42B 106.4 . . ?
H42A C42 H42B 106.5 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
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
Cl1 C31 1.742(3) . ?
O2 C21 1.233(3) . ?
N4 C27 1.353(3) . ?
N4 C34 1.383(3) . ?
N4 N3 1.404(3) . ?
N3 C21 1.352(3) . ?
N3 C28 1.468(3) . ?
C22 C23 1.382(4) . ?
C22 C27 1.389(3) . ?
C22 C21 1.465(4) . ?
C27 C26 1.395(4) . ?
C26 C25 1.362(4) . ?
C26 H26 0.9300 . ?
C23 C24 1.359(4) . ?
C23 H23 0.9300 . ?
C25 C24 1.390(4) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
C31 C32 1.372(4) . ?
C31 C30 1.376(3) . ?
C30 C29 1.373(4) . ?
C30 H30 0.9300 . ?
C28 C36 1.503(4) . ?
C28 C29 1.512(3) . ?
C28 C35 1.543(5) . ?
C32 C33 1.383(4) . ?
C32 H32 0.9300 . ?
C34 C33 1.381(4) . ?
C34 C29 1.397(3) . ?
C33 H33 0.9300 . ?
C35 C37 1.509(5) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C41 1.434(6) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.521(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
O3 C41 1.240(5) . ?
C41 C42 1.508(6) . ?
C42 C43 1.222(7) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352523
