#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/78/7127805.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_7127805
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 H22 Br Cl N2 O2'
_chemical_formula_sum            'C28 H22 Br Cl N2 O2'
_chemical_formula_weight         533.84
_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                 113.870(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.544(5)
_cell_length_b                   16.528(4)
_cell_length_c                   9.324(3)
_cell_measurement_reflns_used    5241
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.886
_cell_measurement_theta_min      2.526
_cell_volume                     2472.4(12)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0796
_diffrn_reflns_av_sigmaI/netI    0.0876
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_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            19037
_diffrn_reflns_theta_full        25.43
_diffrn_reflns_theta_max         25.43
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    1.799
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_correction_T_min  0.7742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4472
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0388P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                3306
_reflns_number_total             4472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc08184a2.cif
_cod_data_source_block           d22440
_cod_depositor_comments
'Adding full bibliography for 7127803--7127811.cif.'
_cod_original_cell_volume        2472.5(11)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7127805
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 0.7669(3) 0.5478(3) 0.6449(6) 0.0345(11) Uani 1 1 d . . .
C2 C 0.7189(3) 0.6095(3) 0.5558(5) 0.0327(11) Uani 1 1 d . . .
H2 H 0.7431 0.6493 0.5133 0.039 Uiso 1 1 calc R . .
C3 C 0.6350(3) 0.6141(3) 0.5275(5) 0.0313(10) Uani 1 1 d . . .
H3 H 0.6022 0.6578 0.4680 0.038 Uiso 1 1 calc R . .
C4 C 0.5982(3) 0.5548(2) 0.5861(5) 0.0267(10) Uani 1 1 d . . .
C5 C 0.6483(3) 0.4935(3) 0.6783(6) 0.0338(12) Uani 1 1 d . . .
H5 H 0.6249 0.4542 0.7229 0.041 Uiso 1 1 calc R . .
C6 C 0.7316(3) 0.4889(3) 0.7061(6) 0.0367(12) Uani 1 1 d . . .
H6 H 0.7648 0.4456 0.7667 0.044 Uiso 1 1 calc R . .
C7 C 0.5091(3) 0.5605(3) 0.5579(6) 0.0253(11) Uani 1 1 d . . .
C8 C 0.4602(3) 0.6324(2) 0.5341(5) 0.0255(10) Uani 1 1 d . . .
C9 C 0.4612(3) 0.7224(3) 0.5146(5) 0.0294(10) Uani 1 1 d . . .
C10 C 0.3758(3) 0.7493(3) 0.5016(5) 0.0312(11) Uani 1 1 d . . .
C11 C 0.3433(3) 0.8257(3) 0.4827(6) 0.0400(12) Uani 1 1 d . . .
H11 H 0.3748 0.8709 0.4746 0.048 Uiso 1 1 calc R . .
C12 C 0.2631(4) 0.8362(3) 0.4754(6) 0.0516(15) Uani 1 1 d . . .
H12 H 0.2392 0.8888 0.4609 0.062 Uiso 1 1 calc R . .
C13 C 0.2176(3) 0.7693(3) 0.4896(7) 0.0545(15) Uani 1 1 d . . .
H13 H 0.1635 0.7772 0.4873 0.065 Uiso 1 1 calc R . .
C14 C 0.2504(3) 0.6913(3) 0.5069(6) 0.0424(13) Uani 1 1 d . . .
H14 H 0.2191 0.6459 0.5152 0.051 Uiso 1 1 calc R . .
C15 C 0.3281(3) 0.6820(3) 0.5115(5) 0.0305(10) Uani 1 1 d . . .
C16 C 0.3836(3) 0.6123(2) 0.5285(5) 0.0256(10) Uani 1 1 d . . .
C17 C 0.2630(3) 0.4476(3) 0.4204(6) 0.0303(11) Uani 1 1 d . . .
C18 C 0.1916(3) 0.4001(3) 0.4377(5) 0.0368(12) Uani 1 1 d . . .
C19 C 0.1197(3) 0.4576(4) 0.4054(9) 0.078(2) Uani 1 1 d . . .
H19A H 0.1037 0.4816 0.3011 0.117 Uiso 1 1 calc R . .
H19B H 0.1365 0.5005 0.4847 0.117 Uiso 1 1 calc R . .
H19C H 0.0722 0.4280 0.4095 0.117 Uiso 1 1 calc R . .
C20 C 0.2172(3) 0.3623(4) 0.6007(6) 0.0550(15) Uani 1 1 d . . .
H20A H 0.1718 0.3283 0.6021 0.082 Uiso 1 1 calc R . .
H20B H 0.2291 0.4053 0.6791 0.082 Uiso 1 1 calc R . .
H20C H 0.2673 0.3292 0.6250 0.082 Uiso 1 1 calc R . .
C21 C 0.1677(4) 0.3314(4) 0.3175(7) 0.073(2) Uani 1 1 d . . .
H21A H 0.1486 0.3542 0.2117 0.110 Uiso 1 1 calc R . .
H21B H 0.1229 0.2992 0.3263 0.110 Uiso 1 1 calc R . .
H21C H 0.2163 0.2968 0.3376 0.110 Uiso 1 1 calc R . .
C22 C 0.4576(3) 0.4973(3) 0.5630(5) 0.0247(10) Uani 1 1 d . . .
C23 C 0.4658(3) 0.4087(2) 0.5457(5) 0.0256(10) Uani 1 1 d . . .
C24 C 0.4459(3) 0.3526(2) 0.6343(5) 0.0335(11) Uani 1 1 d . . .
H24 H 0.4308 0.3704 0.7162 0.040 Uiso 1 1 calc R . .
C25 C 0.4476(3) 0.2695(3) 0.6049(6) 0.0376(12) Uani 1 1 d . . .
H25 H 0.4322 0.2309 0.6640 0.045 Uiso 1 1 calc R . .
C26 C 0.4719(3) 0.2450(3) 0.4889(5) 0.0352(11) Uani 1 1 d . . .
C27 C 0.4946(3) 0.3001(3) 0.4013(6) 0.0318(11) Uani 1 1 d . . .
H27 H 0.5124 0.2821 0.3231 0.038 Uiso 1 1 calc R . .
C28 C 0.4909(3) 0.3822(3) 0.4299(5) 0.0293(10) Uani 1 1 d . . .
H28 H 0.5056 0.4206 0.3697 0.035 Uiso 1 1 calc R . .
N1 N 0.3816(2) 0.5313(2) 0.5482(4) 0.0277(8) Uani 1 1 d . . .
N2 N 0.3141(2) 0.4876(2) 0.5517(4) 0.0273(8) Uani 1 1 d . . .
H2A H 0.3049 0.4860 0.6376 0.033 Uiso 1 1 calc R . .
O1 O 0.5150(2) 0.76575(18) 0.5083(4) 0.0424(8) Uani 1 1 d . . .
O2 O 0.2733(2) 0.4508(2) 0.2994(4) 0.0387(9) Uani 1 1 d . . .
Br1 Br 0.88118(3) 0.54052(3) 0.68357(5) 0.05200(18) Uani 1 1 d . . .
Cl1 Cl 0.47208(11) 0.14308(7) 0.44242(18) 0.0617(4) 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'
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'
Br Br -0.2901 2.4595 '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'
F F 0.0171 0.0103 '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 C1 C6 120.2(4) . . ?
C2 C1 Br1 120.4(3) . . ?
C6 C1 Br1 119.3(4) . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 C7 121.0(4) . . ?
C3 C4 C7 120.4(4) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C22 C7 C8 105.7(4) . . ?
C22 C7 C4 126.8(4) . . ?
C8 C7 C4 127.2(4) . . ?
C16 C8 C7 108.9(4) . . ?
C16 C8 C9 107.2(4) . . ?
C7 C8 C9 143.9(4) . . ?
O1 C9 C8 130.0(4) . . ?
O1 C9 C10 126.0(4) . . ?
C8 C9 C10 103.9(4) . . ?
C11 C10 C15 120.4(4) . . ?
C11 C10 C9 128.8(4) . . ?
C15 C10 C9 110.8(4) . . ?
C10 C11 C12 118.8(5) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 118.0(5) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 121.5(4) . . ?
C14 C15 C16 134.7(4) . . ?
C10 C15 C16 103.8(4) . . ?
N1 C16 C8 108.3(4) . . ?
N1 C16 C15 137.3(4) . . ?
C8 C16 C15 114.3(4) . . ?
O2 C17 N2 121.6(4) . . ?
O2 C17 C18 123.5(4) . . ?
N2 C17 C18 114.9(4) . . ?
C19 C18 C21 111.2(5) . . ?
C19 C18 C20 109.9(5) . . ?
C21 C18 C20 107.9(4) . . ?
C19 C18 C17 107.9(4) . . ?
C21 C18 C17 107.2(4) . . ?
C20 C18 C17 112.8(4) . . ?
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 . . ?
C7 C22 N1 107.5(4) . . ?
C7 C22 C23 129.8(4) . . ?
N1 C22 C23 121.0(4) . . ?
C24 C23 C28 119.3(4) . . ?
C24 C23 C22 122.6(4) . . ?
C28 C23 C22 118.0(4) . . ?
C23 C24 C25 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 118.7(4) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
C25 C26 C27 121.7(4) . . ?
C25 C26 Cl1 120.9(4) . . ?
C27 C26 Cl1 117.4(4) . . ?
C26 C27 C28 118.8(4) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C27 C28 C23 120.7(4) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
C16 N1 N2 125.6(4) . . ?
C16 N1 C22 109.6(4) . . ?
N2 N1 C22 124.8(3) . . ?
C17 N2 N1 119.1(4) . . ?
C17 N2 H2A 120.5 . . ?
N1 N2 H2A 120.5 . . ?
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
C1 C2 1.369(6) . ?
C1 C6 1.394(7) . ?
C1 Br1 1.892(5) . ?
C2 C3 1.390(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(6) . ?
C4 C7 1.478(6) . ?
C5 C6 1.379(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C22 1.395(6) . ?
C7 C8 1.429(6) . ?
C8 C16 1.366(6) . ?
C8 C9 1.500(6) . ?
C9 O1 1.205(5) . ?
C9 C10 1.520(6) . ?
C10 C11 1.368(6) . ?
C10 C15 1.417(6) . ?
C11 C12 1.392(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.356(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.474(6) . ?
C16 N1 1.353(5) . ?
C17 O2 1.213(6) . ?
C17 N2 1.362(6) . ?
C17 C18 1.541(6) . ?
C18 C19 1.510(7) . ?
C18 C21 1.529(7) . ?
C18 C20 1.532(7) . ?
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 . ?
C22 N1 1.401(6) . ?
C22 C23 1.487(6) . ?
C23 C24 1.378(6) . ?
C23 C28 1.391(6) . ?
C24 C25 1.403(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.385(6) . ?
C26 Cl1 1.740(4) . ?
C27 C28 1.389(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N1 N2 1.398(5) . ?
N2 H2A 0.8800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352508
