#------------------------------------------------------------------------------
#$Date: 2022-08-16 00:51:12 +0300 (Tue, 16 Aug 2022) $
#$Revision: 277244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/05/7130533.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_7130533
loop_
_publ_author_name
'Mandal, Mou'
'Balamurugan, Rengarajan'
_publ_section_title
;
 TfOH-promoted synthesis of indoles and benzofurans involving cyclative
 transposition of vinyl ketone
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03730K
_journal_year                    2022
_chemical_formula_sum            'C23 H16 O2'
_chemical_formula_weight         324.36
_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-2018/3
_audit_update_record
;
2022-04-14 deposited with the CCDC.	2022-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.26(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.716(6)
_cell_length_b                   14.621(7)
_cell_length_c                   10.413(5)
_cell_measurement_temperature    300(2)
_cell_volume                     1703.4(15)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8336
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         1.820
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.313
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.313
_refine_ls_R_factor_all          0.1864
_refine_ls_R_factor_gt           0.1195
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2841
_refine_ls_wR_factor_ref         0.3502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1800
_reflns_number_total             2759
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03730k4.cif
_cod_data_source_block           rb016_0ma_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130533
_shelx_shelxl_version_number     2018/3
_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   0.984
_shelx_estimated_absorpt_t_max   0.992
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
O1 O 0.6222(2) 0.55715(18) 0.6734(2) 0.0535(8) Uani 1 1 d . . . . .
O2 O 0.8699(3) 0.31350(18) 0.7235(2) 0.0610(9) Uani 1 1 d . . . . .
C17 C 0.8443(3) 0.2693(3) 0.6199(3) 0.0470(10) Uani 1 1 d . . . . .
C18 C 0.8706(3) 0.1695(2) 0.6218(3) 0.0464(10) Uani 1 1 d . . . . .
C9 C 0.7321(3) 0.6103(2) 0.5236(3) 0.0426(9) Uani 1 1 d . . . . .
C2 C 0.6816(3) 0.4410(3) 0.5602(3) 0.0477(10) Uani 1 1 d . . . . .
C23 C 0.8170(3) 0.1122(2) 0.5125(4) 0.0554(12) Uani 1 1 d . . . . .
H23 H 0.763558 0.136778 0.435625 0.066 Uiso 1 1 calc R U . . .
C16 C 0.7914(4) 0.3132(2) 0.4859(4) 0.0534(11) Uani 1 1 d . . . . .
H16 H 0.804520 0.284904 0.411522 0.064 Uiso 1 1 calc R U . . .
C19 C 0.9511(3) 0.1299(3) 0.7358(3) 0.0545(11) Uani 1 1 d . . . . .
H19 H 0.986262 0.165904 0.810756 0.065 Uiso 1 1 calc R U . . .
C4 C 0.5830(3) 0.4764(3) 0.7127(4) 0.0532(11) Uani 1 1 d . . . . .
C8 C 0.5816(4) 0.3150(3) 0.6760(4) 0.0647(13) Uani 1 1 d . . . . .
H8 H 0.601685 0.263930 0.634086 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7100(4) 0.6991(3) 0.5545(4) 0.0568(11) Uani 1 1 d . . . . .
H10 H 0.662942 0.709426 0.610931 0.068 Uiso 1 1 calc R U . . .
C3 C 0.6164(3) 0.4028(3) 0.6481(4) 0.0511(10) Uani 1 1 d . . . . .
C15 C 0.7269(4) 0.3899(3) 0.4648(3) 0.0541(11) Uani 1 1 d . . . . .
H15 H 0.708341 0.413933 0.378412 0.065 Uiso 1 1 calc R U . . .
C13 C 0.8525(4) 0.6720(3) 0.3893(4) 0.0599(11) Uani 1 1 d . . . . .
H13 H 0.900171 0.662625 0.333319 0.072 Uiso 1 1 calc R U . . .
C1 C 0.6812(3) 0.5331(3) 0.5782(3) 0.0479(10) Uani 1 1 d . . . . .
C14 C 0.8067(4) 0.5977(3) 0.4411(4) 0.0552(11) Uani 1 1 d . . . . .
H14 H 0.825722 0.538662 0.421063 0.066 Uiso 1 1 calc R U . . .
C6 C 0.4842(4) 0.3802(4) 0.8296(5) 0.0784(15) Uani 1 1 d . . . . .
H6 H 0.440079 0.371256 0.889510 0.094 Uiso 1 1 calc R U . . .
C21 C 0.9252(4) -0.0165(3) 0.6295(4) 0.0632(12) Uani 1 1 d . . . . .
H21 H 0.944934 -0.078165 0.631345 0.076 Uiso 1 1 calc R U . . .
C12 C 0.8272(4) 0.7591(3) 0.4209(5) 0.0660(12) Uani 1 1 d . . . . .
H12 H 0.857791 0.809026 0.386568 0.079 Uiso 1 1 calc R U . . .
C22 C 0.8418(4) 0.0210(3) 0.5173(4) 0.0678(14) Uani 1 1 d . . . . .
H22 H 0.802963 -0.016384 0.445410 0.081 Uiso 1 1 calc R U . . .
C20 C 0.9780(4) 0.0391(3) 0.7378(4) 0.0650(13) Uani 1 1 d . . . . .
H20 H 1.032940 0.014296 0.813335 0.078 Uiso 1 1 calc R U . . .
C5 C 0.5166(4) 0.4682(4) 0.8044(5) 0.0710(13) Uani 1 1 d . . . . .
H5 H 0.495374 0.519001 0.845939 0.085 Uiso 1 1 calc R U . . .
C7 C 0.5170(4) 0.3056(4) 0.7665(5) 0.0768(15) Uani 1 1 d . . . . .
H7 H 0.494757 0.247284 0.785776 0.092 Uiso 1 1 calc R U . . .
C11 C 0.7558(4) 0.7726(3) 0.5041(5) 0.0680(13) Uani 1 1 d . . . . .
H11 H 0.738818 0.831739 0.525994 0.082 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'
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
C4 O1 C1 105.8(3) . . ?
O2 C17 C18 120.9(3) . . ?
O2 C17 C16 121.6(3) . . ?
C18 C17 C16 117.4(3) . . ?
C23 C18 C19 117.8(3) . . ?
C23 C18 C17 122.2(3) . . ?
C19 C18 C17 119.9(3) . . ?
C10 C9 C14 117.3(4) . . ?
C10 C9 C1 120.5(4) . . ?
C14 C9 C1 122.1(3) . . ?
C1 C2 C15 128.1(4) . . ?
C1 C2 C3 105.6(4) . . ?
C15 C2 C3 126.2(3) . . ?
C22 C23 C18 121.0(3) . . ?
C15 C16 C17 124.9(4) . . ?
C20 C19 C18 120.6(3) . . ?
O1 C4 C3 110.8(4) . . ?
O1 C4 C5 125.4(4) . . ?
C3 C4 C5 123.9(4) . . ?
C7 C8 C3 119.0(5) . . ?
C11 C10 C9 121.8(4) . . ?
C4 C3 C8 117.9(4) . . ?
C4 C3 C2 106.4(4) . . ?
C8 C3 C2 135.7(4) . . ?
C16 C15 C2 128.3(3) . . ?
C12 C13 C14 119.9(4) . . ?
C2 C1 O1 111.5(4) . . ?
C2 C1 C9 133.7(4) . . ?
O1 C1 C9 114.8(3) . . ?
C13 C14 C9 121.0(4) . . ?
C7 C6 C5 120.7(5) . . ?
C20 C21 C22 119.1(4) . . ?
C13 C12 C11 119.8(4) . . ?
C23 C22 C21 120.3(4) . . ?
C19 C20 C21 121.1(3) . . ?
C6 C5 C4 116.5(5) . . ?
C8 C7 C6 122.0(5) . . ?
C10 C11 C12 120.3(4) . . ?
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 C4 1.373(4) . ?
O1 C1 1.411(5) . ?
O2 C17 1.216(4) . ?
C17 C18 1.490(5) . ?
C17 C16 1.494(5) . ?
C18 C23 1.403(5) . ?
C18 C19 1.404(5) . ?
C9 C10 1.380(5) . ?
C9 C14 1.408(6) . ?
C9 C1 1.468(5) . ?
C2 C1 1.359(5) . ?
C2 C15 1.463(6) . ?
C2 C3 1.466(6) . ?
C23 C22 1.362(5) . ?
C16 C15 1.334(5) . ?
C19 C20 1.363(6) . ?
C4 C3 1.386(6) . ?
C4 C5 1.404(7) . ?
C8 C7 1.379(7) . ?
C8 C3 1.403(5) . ?
C10 C11 1.373(6) . ?
C13 C12 1.370(6) . ?
C13 C14 1.390(6) . ?
C6 C7 1.386(7) . ?
C6 C5 1.388(7) . ?
C21 C20 1.378(5) . ?
C21 C22 1.394(5) . ?
C12 C11 1.386(7) . ?
