#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/78/7127807.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_7127807
loop_
_publ_author_name
'Edukondalu, Athukuri'
'Vagh, Sandip Sambhaji'
'Lin, Ting-Han'
'Lin, Wenwei'
_publ_section_title
;
 Construction of indeno[1,2-b]pyrroles via chemoselective
 N-acylation/cyclization/Wittig reaction sequence.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2045
_journal_page_last               2048
_journal_paper_doi               10.1039/d0cc08184a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C28 H23 Br N2 O2'
_chemical_formula_sum            'C28 H23 Br N2 O2'
_chemical_formula_weight         499.39
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-06-14 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.2390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.2881(7)
_cell_length_b                   16.3136(7)
_cell_length_c                   9.3609(4)
_cell_measurement_reflns_used    4103
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.455
_cell_measurement_theta_min      2.497
_cell_volume                     2425.87(18)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 Venture'
_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  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16214
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  0.9664
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4042
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+1.1628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                3080
_reflns_number_total             4042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc08184a2.cif
_cod_data_source_block           d22219
_cod_depositor_comments
'Adding full bibliography for 7127803--7127811.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7127807
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7367(3) 0.4624(3) 0.6435(6) 0.0471(12) Uani 1 1 d . . .
C2 C 0.6907(3) 0.3963(3) 0.5622(5) 0.0449(11) Uani 1 1 d . . .
H2 H 0.7162 0.3552 0.5234 0.054 Uiso 1 1 calc R . .
C3 C 0.6053(3) 0.3908(3) 0.5378(5) 0.0384(10) Uani 1 1 d . . .
H3 H 0.5732 0.3450 0.4838 0.046 Uiso 1 1 calc R . .
C4 C 0.5669(3) 0.4522(3) 0.5922(4) 0.0348(10) Uani 1 1 d . . .
C5 C 0.6170(3) 0.5166(3) 0.6753(5) 0.0400(11) Uani 1 1 d . . .
H5 H 0.5927 0.5577 0.7165 0.048 Uiso 1 1 calc R . .
C6 C 0.7006(3) 0.5228(3) 0.6998(5) 0.0469(12) Uani 1 1 d . . .
H6 H 0.7331 0.5683 0.7550 0.056 Uiso 1 1 calc R . .
C7 C 0.4781(3) 0.4439(3) 0.5673(5) 0.0328(10) Uani 1 1 d . . .
C8 C 0.4305(3) 0.3701(2) 0.5448(4) 0.0327(9) Uani 1 1 d . . .
C9 C 0.4322(3) 0.2797(3) 0.5287(5) 0.0377(10) Uani 1 1 d . . .
C10 C 0.3449(3) 0.2516(3) 0.5016(5) 0.0392(11) Uani 1 1 d . . .
C11 C 0.3119(3) 0.1735(3) 0.4727(5) 0.0485(12) Uani 1 1 d . . .
H11 H 0.3456 0.1282 0.4691 0.058 Uiso 1 1 calc R . .
C12 C 0.2270(3) 0.1627(3) 0.4487(6) 0.0552(13) Uani 1 1 d . . .
H12 H 0.2024 0.1096 0.4276 0.066 Uiso 1 1 calc R . .
C13 C 0.1791(3) 0.2291(3) 0.4559(6) 0.0607(14) Uani 1 1 d . . .
H13 H 0.1219 0.2209 0.4402 0.073 Uiso 1 1 calc R . .
C14 C 0.2129(3) 0.3083(3) 0.4859(6) 0.0471(11) Uani 1 1 d . . .
H14 H 0.1795 0.3536 0.4910 0.057 Uiso 1 1 calc R . .
C15 C 0.2953(3) 0.3185(2) 0.5075(5) 0.0346(10) Uani 1 1 d . . .
C16 C 0.3506(3) 0.3891(2) 0.5332(4) 0.0314(9) Uani 1 1 d . . .
C17 C 0.2260(3) 0.5528(3) 0.4112(5) 0.0367(10) Uani 1 1 d . A .
C18 C 0.1541(3) 0.6028(3) 0.4239(6) 0.0522(13) Uani 1 1 d . . .
C19 C 0.1759(4) 0.6391(4) 0.5845(6) 0.0803(19) Uani 1 1 d . A .
H19A H 0.2292 0.6691 0.6165 0.120 Uiso 1 1 calc R . .
H19B H 0.1815 0.5949 0.6589 0.120 Uiso 1 1 calc R . .
H19C H 0.1312 0.6766 0.5818 0.120 Uiso 1 1 calc R . .
C20 C 0.0842(8) 0.5342(8) 0.4279(18) 0.060(4) Uiso 0.431(18) 1 d P A 1
H20A H 0.1107 0.4970 0.5161 0.090 Uiso 0.431(18) 1 calc PR A 1
H20B H 0.0636 0.5027 0.3309 0.090 Uiso 0.431(18) 1 calc PR A 1
H20C H 0.0368 0.5624 0.4392 0.090 Uiso 0.431(18) 1 calc PR A 1
C21 C 0.1136(12) 0.6549(11) 0.2935(17) 0.072(5) Uiso 0.431(18) 1 d P A 1
H21A H 0.0681 0.6851 0.3076 0.108 Uiso 0.431(18) 1 calc PR A 1
H21B H 0.0902 0.6217 0.1987 0.108 Uiso 0.431(18) 1 calc PR A 1
H21C H 0.1546 0.6938 0.2844 0.108 Uiso 0.431(18) 1 calc PR A 1
C20' C 0.0762(9) 0.5649(10) 0.345(2) 0.103(5) Uiso 0.569(18) 1 d P A 2
H20D H 0.0316 0.5984 0.3554 0.154 Uiso 0.569(18) 1 calc PR A 2
H20E H 0.0764 0.5105 0.3896 0.154 Uiso 0.569(18) 1 calc PR A 2
H20F H 0.0659 0.5594 0.2347 0.154 Uiso 0.569(18) 1 calc PR A 2
C21' C 0.1510(8) 0.6885(7) 0.3271(12) 0.062(3) Uiso 0.569(18) 1 d P A 2
H21D H 0.2043 0.7180 0.3769 0.092 Uiso 0.569(18) 1 calc PR A 2
H21E H 0.1046 0.7229 0.3276 0.092 Uiso 0.569(18) 1 calc PR A 2
H21F H 0.1421 0.6752 0.2196 0.092 Uiso 0.569(18) 1 calc PR A 2
C22 C 0.4229(3) 0.5069(2) 0.5660(4) 0.0301(9) Uani 1 1 d . . .
C23 C 0.4286(2) 0.5973(3) 0.5569(4) 0.0310(9) Uani 1 1 d . . .
C24 C 0.4078(3) 0.6489(3) 0.6529(5) 0.0382(10) Uani 1 1 d . . .
H24 H 0.3951 0.6266 0.7348 0.046 Uiso 1 1 calc R . .
C25 C 0.4053(3) 0.7333(3) 0.6313(5) 0.0489(12) Uani 1 1 d . . .
H25 H 0.3903 0.7681 0.6975 0.059 Uiso 1 1 calc R . .
C26 C 0.4246(3) 0.7664(3) 0.5145(5) 0.0481(12) Uani 1 1 d . . .
H26 H 0.4220 0.8240 0.4985 0.058 Uiso 1 1 calc R . .
C27 C 0.4478(3) 0.7156(3) 0.4206(5) 0.0458(12) Uani 1 1 d . . .
H27 H 0.4633 0.7387 0.3425 0.055 Uiso 1 1 calc R . .
C28 C 0.4488(3) 0.6320(3) 0.4384(5) 0.0357(10) Uani 1 1 d . . .
H28 H 0.4632 0.5976 0.3707 0.043 Uiso 1 1 calc R . .
Br1 Br 0.85246(4) 0.46946(3) 0.67890(5) 0.06587(19) Uani 1 1 d . . .
N1 N 0.3465(2) 0.4707(2) 0.5484(4) 0.0325(8) Uani 1 1 d . A .
N2 N 0.2759(2) 0.5137(2) 0.5436(4) 0.0351(8) Uani 1 1 d . . .
H2A H 0.2636 0.5155 0.6262 0.042 Uiso 1 1 calc R A .
O1 O 0.4897(2) 0.23480(19) 0.5315(4) 0.0534(8) Uani 1 1 d . . .
O2 O 0.2404(2) 0.5477(2) 0.2939(4) 0.0444(9) Uani 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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 121.4(4) . . ?
C6 C1 Br1 119.7(4) . . ?
C2 C1 Br1 118.9(4) . . ?
C1 C2 C3 118.7(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 117.6(4) . . ?
C5 C4 C7 122.7(4) . . ?
C3 C4 C7 119.6(4) . . ?
C6 C5 C4 122.1(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 119.3(5) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C22 C7 C8 105.5(4) . . ?
C22 C7 C4 127.1(5) . . ?
C8 C7 C4 127.4(4) . . ?
C16 C8 C7 108.8(3) . . ?
C16 C8 C9 105.9(4) . . ?
C7 C8 C9 145.2(4) . . ?
O1 C9 C8 129.7(4) . . ?
O1 C9 C10 125.0(4) . . ?
C8 C9 C10 105.2(3) . . ?
C11 C10 C15 121.0(4) . . ?
C11 C10 C9 128.8(4) . . ?
C15 C10 C9 110.2(4) . . ?
C10 C11 C12 118.1(4) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.5(5) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 118.0(4) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 121.1(4) . . ?
C14 C15 C16 134.4(4) . . ?
C10 C15 C16 104.5(4) . . ?
N1 C16 C8 108.0(3) . . ?
N1 C16 C15 138.0(4) . . ?
C8 C16 C15 114.1(3) . . ?
O2 C17 N2 120.4(4) . . ?
O2 C17 C18 124.5(4) . . ?
N2 C17 C18 115.0(4) . . ?
C20' C18 C21 76.4(9) . . ?
C20' C18 C19 120.4(8) . . ?
C21 C18 C19 117.5(8) . . ?
C20' C18 C17 111.5(7) . . ?
C21 C18 C17 113.1(7) . . ?
C19 C18 C17 113.1(4) . . ?
C20' C18 C21' 105.5(8) . . ?
C21 C18 C21' 29.3(7) . . ?
C19 C18 C21' 98.9(6) . . ?
C17 C18 C21' 105.1(5) . . ?
C20' C18 C20 32.4(7) . . ?
C21 C18 C20 107.8(9) . . ?
C19 C18 C20 98.0(7) . . ?
C17 C18 C20 105.3(6) . . ?
C21' C18 C20 135.7(7) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C20' H20D 109.5 . . ?
C18 C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C18 C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C18 C21' H21D 109.5 . . ?
C18 C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C18 C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
N1 C22 C7 107.5(4) . . ?
N1 C22 C23 119.6(3) . . ?
C7 C22 C23 132.1(4) . . ?
C24 C23 C28 118.5(4) . . ?
C24 C23 C22 122.0(4) . . ?
C28 C23 C22 119.2(3) . . ?
C23 C24 C25 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 120.1(4) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.6(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 120.9(4) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C23 120.0(4) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C16 N1 N2 125.3(3) . . ?
C16 N1 C22 110.1(3) . . ?
N2 N1 C22 124.6(3) . . ?
C17 N2 N1 119.9(3) . . ?
C17 N2 H2A 120.0 . . ?
N1 N2 H2A 120.0 . . ?
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
C1 C6 1.379(6) . ?
C1 C2 1.377(6) . ?
C1 Br1 1.898(4) . ?
C2 C3 1.405(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(6) . ?
C4 C7 1.466(6) . ?
C5 C6 1.374(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C22 1.399(6) . ?
C7 C8 1.426(7) . ?
C8 C16 1.378(5) . ?
C8 C9 1.484(6) . ?
C9 O1 1.227(5) . ?
C9 C10 1.500(6) . ?
C10 C11 1.379(6) . ?
C10 C15 1.402(6) . ?
C11 C12 1.406(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.368(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.455(6) . ?
C16 N1 1.344(5) . ?
C17 O2 1.221(5) . ?
C17 N2 1.358(5) . ?
C17 C18 1.529(6) . ?
C18 C20' 1.399(15) . ?
C18 C21 1.424(14) . ?
C18 C19 1.519(7) . ?
C18 C21' 1.655(12) . ?
C18 C20 1.659(14) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C21' H21D 0.9800 . ?
C21' H21E 0.9800 . ?
C21' H21F 0.9800 . ?
C22 N1 1.396(5) . ?
C22 C23 1.482(6) . ?
C23 C24 1.378(5) . ?
C23 C28 1.407(6) . ?
C24 C25 1.389(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.374(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.377(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.374(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N1 N2 1.393(4) . ?
N2 H2A 0.8800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352511
