#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/78/7127806.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_7127806
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         'C30 H20 Br Cl N2 O3'
_chemical_formula_sum            'C30 H20 Br Cl N2 O3'
_chemical_formula_weight         571.84
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/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                 115.5280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.7223(10)
_cell_length_b                   6.9755(2)
_cell_length_c                   27.9045(9)
_cell_measurement_reflns_used    6773
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.053
_cell_measurement_theta_min      2.612
_cell_volume                     5396.2(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            36745
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_T_max  0.9676
_exptl_absorpt_correction_T_min  0.7775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.155
_refine_diff_density_min         -1.374
_refine_diff_density_rms         0.092
_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     335
_refine_ls_number_reflns         4758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0702
_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)+(0.0994P)²+38.1717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1973
_reflns_number_gt                3584
_reflns_number_total             4758
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc08184a2.cif
_cod_data_source_block           d22372
_cod_depositor_comments
'Adding full bibliography for 7127803--7127811.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7127806
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'
'-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 0.6027(2) 0.6845(9) 0.7795(2) 0.0479(15) Uani 1 1 d . . .
C2 C 0.5747(2) 0.8084(9) 0.7409(2) 0.0543(16) Uani 1 1 d . . .
H2 H 0.5560 0.9021 0.7484 0.065 Uiso 1 1 calc R . .
C3 C 0.5732(2) 0.7982(9) 0.6906(2) 0.0449(14) Uani 1 1 d . . .
H3 H 0.5531 0.8839 0.6637 0.054 Uiso 1 1 calc R . .
C4 C 0.60063(15) 0.6649(7) 0.67913(17) 0.0265(10) Uani 1 1 d . . .
C5 C 0.62817(17) 0.5375(8) 0.71914(18) 0.0338(11) Uani 1 1 d . . .
H5 H 0.6464 0.4415 0.7118 0.041 Uiso 1 1 calc R . .
C6 C 0.6297(2) 0.5472(9) 0.7691(2) 0.0464(14) Uani 1 1 d . . .
H6 H 0.6491 0.4604 0.7961 0.056 Uiso 1 1 calc R . .
C7 C 0.59942(15) 0.6575(6) 0.62554(17) 0.0235(9) Uani 1 1 d . . .
C8 C 0.55882(16) 0.7007(6) 0.57648(17) 0.0227(9) Uani 1 1 d . . .
C9 C 0.50817(16) 0.7583(6) 0.55251(18) 0.0224(9) Uani 1 1 d . . .
C10 C 0.49335(16) 0.7592(6) 0.49297(18) 0.0241(10) Uani 1 1 d . . .
C11 C 0.44975(17) 0.8050(6) 0.45236(19) 0.0287(10) Uani 1 1 d . . .
H11 H 0.4234 0.8451 0.4592 0.034 Uiso 1 1 calc R . .
C12 C 0.44526(17) 0.7905(7) 0.4001(2) 0.0338(11) Uani 1 1 d . . .
H12 H 0.4154 0.8213 0.3711 0.041 Uiso 1 1 calc R . .
C13 C 0.48343(19) 0.7324(7) 0.39046(19) 0.0360(12) Uani 1 1 d . . .
H13 H 0.4793 0.7215 0.3548 0.043 Uiso 1 1 calc R . .
C14 C 0.52850(18) 0.6888(7) 0.43226(18) 0.0298(10) Uani 1 1 d . . .
H14 H 0.5551 0.6517 0.4255 0.036 Uiso 1 1 calc R . .
C15 C 0.53281(16) 0.7015(6) 0.48323(17) 0.0228(9) Uani 1 1 d . . .
C16 C 0.57200(15) 0.6672(6) 0.53627(16) 0.0207(9) Uani 1 1 d . . .
C17 C 0.65667(16) 0.7339(7) 0.50811(17) 0.0248(10) Uani 1 1 d . . .
C18 C 0.67932(16) 0.6952(7) 0.47178(18) 0.0278(10) Uani 1 1 d . . .
C19 C 0.6732(2) 0.8278(8) 0.4321(2) 0.0406(13) Uani 1 1 d . . .
H19 H 0.6543 0.9394 0.4283 0.049 Uiso 1 1 calc R . .
C20 C 0.6946(2) 0.7972(9) 0.3988(2) 0.0487(15) Uani 1 1 d . . .
H20 H 0.6897 0.8869 0.3713 0.058 Uiso 1 1 calc R . .
C21 C 0.7231(2) 0.6380(10) 0.4043(2) 0.0491(15) Uani 1 1 d . . .
H21 H 0.7382 0.6192 0.3813 0.059 Uiso 1 1 calc R . .
C22 C 0.72927(19) 0.5075(9) 0.4435(2) 0.0456(14) Uani 1 1 d . . .
H22 H 0.7489 0.3977 0.4476 0.055 Uiso 1 1 calc R . .
C23 C 0.70749(17) 0.5335(7) 0.4769(2) 0.0333(11) Uani 1 1 d . . .
H23 H 0.7117 0.4409 0.5035 0.040 Uiso 1 1 calc R . .
C24 C 0.63629(15) 0.6018(6) 0.61265(16) 0.0202(9) Uani 1 1 d . . .
C25 C 0.68794(16) 0.5682(7) 0.64679(17) 0.0265(10) Uani 1 1 d . . .
C26 C 0.71393(17) 0.7143(8) 0.68175(19) 0.0363(12) Uani 1 1 d . . .
H26 H 0.6983 0.8310 0.6825 0.044 Uiso 1 1 calc R . .
C27 C 0.76285(19) 0.6892(10) 0.7156(2) 0.0479(16) Uani 1 1 d . . .
H27 H 0.7802 0.7879 0.7397 0.058 Uiso 1 1 calc R . .
C28 C 0.78585(19) 0.5233(10) 0.7140(2) 0.0464(15) Uani 1 1 d . . .
H28 H 0.8192 0.5085 0.7367 0.056 Uiso 1 1 calc R . .
C29 C 0.76145(18) 0.3796(9) 0.6804(2) 0.0416(13) Uani 1 1 d . . .
H29 H 0.7778 0.2650 0.6795 0.050 Uiso 1 1 calc R . .
C30 C 0.71243(17) 0.3999(7) 0.64736(19) 0.0301(11) Uani 1 1 d . . .
Br1 Br 0.60517(3) 0.70115(13) 0.84888(3) 0.0736(3) Uani 1 1 d . . .
Cl1 Cl 0.68209(5) 0.20651(18) 0.60780(5) 0.0404(3) Uani 1 1 d . . .
N1 N 0.61793(12) 0.6046(5) 0.55695(14) 0.0198(7) Uani 1 1 d . . .
N2 N 0.64494(13) 0.5744(5) 0.52831(14) 0.0220(8) Uani 1 1 d . . .
H1 H 0.6369 0.4482 0.5093 0.026 Uiso 1 1 d R . .
O1 O 0.48163(11) 0.7973(5) 0.57376(13) 0.0314(8) Uani 1 1 d . . .
O2 O 0.64873(12) 0.8958(4) 0.51964(13) 0.0330(8) Uani 1 1 d . . .
O3 O 0.61816(12) 0.2447(4) 0.46882(13) 0.0300(7) Uani 1 1 d . . .
H3D H 0.6319 0.1511 0.4865 0.036 Uiso 1 1 d R . .
H3C H 0.5905 0.2242 0.4557 0.036 Uiso 1 1 d R . .
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'
Cl Cl 0.1484 0.1585 '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 C1 C6 120.6(5) . . ?
C2 C1 Br1 120.0(4) . . ?
C6 C1 Br1 119.5(4) . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 117.7(4) . . ?
C3 C4 C7 120.3(4) . . ?
C5 C4 C7 122.0(4) . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.1(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C24 C7 C8 106.5(4) . . ?
C24 C7 C4 127.2(4) . . ?
C8 C7 C4 126.2(4) . . ?
C16 C8 C7 107.7(4) . . ?
C16 C8 C9 107.8(4) . . ?
C7 C8 C9 144.4(4) . . ?
O1 C9 C8 129.6(4) . . ?
O1 C9 C10 125.3(4) . . ?
C8 C9 C10 105.1(4) . . ?
C11 C10 C15 121.5(4) . . ?
C11 C10 C9 129.1(4) . . ?
C15 C10 C9 109.4(4) . . ?
C10 C11 C12 117.7(5) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.3(5) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 117.8(4) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C10 120.7(4) . . ?
C14 C15 C16 134.7(4) . . ?
C10 C15 C16 104.6(4) . . ?
N1 C16 C8 109.3(4) . . ?
N1 C16 C15 137.4(4) . . ?
C8 C16 C15 113.2(4) . . ?
O2 C17 N2 121.7(4) . . ?
O2 C17 C18 123.5(4) . . ?
N2 C17 C18 114.8(4) . . ?
C19 C18 C23 119.0(5) . . ?
C19 C18 C17 118.8(4) . . ?
C23 C18 C17 122.2(4) . . ?
C20 C19 C18 119.9(5) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 121.1(5) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 119.0(5) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 120.9(6) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C18 120.1(5) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C7 C24 N1 107.4(4) . . ?
C7 C24 C25 130.5(4) . . ?
N1 C24 C25 121.6(4) . . ?
C30 C25 C26 117.6(4) . . ?
C30 C25 C24 124.6(4) . . ?
C26 C25 C24 117.8(4) . . ?
C25 C26 C27 120.3(5) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 120.3(5) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 120.6(5) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.0(5) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C29 C30 C25 121.2(5) . . ?
C29 C30 Cl1 118.2(4) . . ?
C25 C30 Cl1 120.6(4) . . ?
C16 N1 N2 125.2(3) . . ?
C16 N1 C24 109.0(3) . . ?
N2 N1 C24 125.2(3) . . ?
C17 N2 N1 116.2(3) . . ?
C17 N2 H1 123.2 . . ?
N1 N2 H1 111.3 . . ?
H3D O3 H3C 108.1 . . ?
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 1.360(9) . ?
C1 C6 1.377(8) . ?
C1 Br1 1.908(5) . ?
C2 C3 1.386(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(7) . ?
C4 C7 1.481(6) . ?
C5 C6 1.377(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C24 1.384(6) . ?
C7 C8 1.431(6) . ?
C8 C16 1.367(6) . ?
C8 C9 1.461(6) . ?
C9 O1 1.228(5) . ?
C9 C10 1.522(6) . ?
C10 C11 1.368(6) . ?
C10 C15 1.411(6) . ?
C11 C12 1.408(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.407(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.470(6) . ?
C16 N1 1.346(5) . ?
C17 O2 1.227(6) . ?
C17 N2 1.364(6) . ?
C17 C18 1.481(6) . ?
C18 C19 1.392(7) . ?
C18 C23 1.391(7) . ?
C19 C20 1.366(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.371(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.374(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 N1 1.407(5) . ?
C24 C25 1.476(6) . ?
C25 C30 1.391(7) . ?
C25 C26 1.398(7) . ?
C26 C27 1.399(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.366(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.356(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(7) . ?
C29 H29 0.9500 . ?
C30 Cl1 1.738(5) . ?
N1 N2 1.394(5) . ?
N2 H1 1.0017 . ?
O3 H3D 0.8187 . ?
O3 H3C 0.7794 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352509
