#------------------------------------------------------------------------------
#$Date: 2023-04-13 15:19:33 +0300 (Thu, 13 Apr 2023) $
#$Revision: 282621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159069.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_7159069
loop_
_publ_author_name
'Raji Reddy, Chada'
'Nair, Karna'
'Patil, Amol D.'
'Donthiri, Ramachandra Reddy'
'Grée, René'
_publ_section_title
;
 Domino alkyne insertion/aldol reaction/aromatization of 2-alkynyl
 indole-3-carbaldehyde with 1,3-diketones: entry to 2-indolyl phenols
;
_journal_issue                   5
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1046
_journal_page_last               1055
_journal_paper_doi               10.1039/D2OB02025D
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-02 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.773(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5837(11)
_cell_length_b                   14.4099(13)
_cell_length_c                   12.4674(13)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.9445
_cell_measurement_theta_min      2.16
_cell_volume                     1901.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.429
_diffrn_reflns_theta_min         2.160
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0666
_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)+(0.0560P)²+0.9995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3575
_reflns_number_total             5015
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02025d2.cif
_cod_data_source_block           KA918_0m
_cod_depositor_comments          'Adding full bibliography for 7159069.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159069
#BEGIN Tags that were not found in dictionaries:
_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   0.981
_shelx_estimated_absorpt_t_max   0.986
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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
C1 C 0.40909(16) 0.56606(11) 0.28263(14) 0.0344(4) Uani 1 1 d . . . . .
C2 C 0.51182(17) 0.55503(13) 0.21564(15) 0.0405(4) Uani 1 1 d . . . . .
H2 H 0.509170 0.509655 0.162613 0.049 Uiso 1 1 calc R U . . .
C3 C 0.61776(17) 0.61026(13) 0.22644(15) 0.0429(4) Uani 1 1 d . . . . .
C4 C 0.62133(17) 0.67617(13) 0.30764(16) 0.0433(4) Uani 1 1 d . . . . .
H4 H 0.692404 0.713664 0.315305 0.052 Uiso 1 1 calc R U . . .
C5 C 0.52129(16) 0.68771(11) 0.37802(14) 0.0360(4) Uani 1 1 d . . . . .
C6 C 0.41156(15) 0.63319(11) 0.36422(13) 0.0311(3) Uani 1 1 d . . . . .
C7 C 0.29524(15) 0.64890(11) 0.42646(12) 0.0302(3) Uani 1 1 d . . . . .
C8 C 0.21482(16) 0.72557(11) 0.42400(13) 0.0318(3) Uani 1 1 d . . . . .
C9 C 0.10956(16) 0.70423(12) 0.49234(13) 0.0358(4) Uani 1 1 d . . . . .
C10 C 0.13320(17) 0.61572(12) 0.53441(14) 0.0377(4) Uani 1 1 d . . . . .
C11 C -0.00179(19) 0.75028(15) 0.51995(17) 0.0504(5) Uani 1 1 d . . . . .
H11 H -0.020289 0.808856 0.492630 0.060 Uiso 1 1 calc R U . . .
C12 C -0.0838(2) 0.70611(18) 0.5892(2) 0.0634(6) Uani 1 1 d . . . . .
H12 H -0.158122 0.735826 0.608431 0.076 Uiso 1 1 calc R U . . .
C13 C -0.0577(2) 0.61901(17) 0.63035(19) 0.0641(7) Uani 1 1 d . . . . .
H13 H -0.114913 0.591529 0.676570 0.077 Uiso 1 1 calc R U . . .
C14 C 0.0510(2) 0.57197(15) 0.60454(17) 0.0539(5) Uani 1 1 d . . . . .
H14 H 0.068695 0.513563 0.632692 0.065 Uiso 1 1 calc R U . . .
C15 C 0.53614(17) 0.75184(13) 0.47077(17) 0.0438(4) Uani 1 1 d . . . . .
C16 C 0.5818(2) 0.84139(16) 0.4574(2) 0.0698(7) Uani 1 1 d . . . . .
H16 H 0.598442 0.863618 0.389034 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6027(3) 0.8978(2) 0.5464(3) 0.0927(10) Uani 1 1 d . . . . .
H17 H 0.632809 0.957840 0.536773 0.111 Uiso 1 1 calc R U . . .
C18 C 0.5797(3) 0.8664(2) 0.6479(3) 0.0873(10) Uani 1 1 d . . . . .
H18 H 0.594864 0.904655 0.706793 0.105 Uiso 1 1 calc R U . . .
C19 C 0.5345(2) 0.7788(2) 0.6623(2) 0.0694(7) Uani 1 1 d . . . . .
H19 H 0.518051 0.757296 0.731046 0.083 Uiso 1 1 calc R U . . .
C20 C 0.51298(19) 0.72167(15) 0.57457(17) 0.0508(5) Uani 1 1 d . . . . .
H20 H 0.482420 0.661927 0.585329 0.061 Uiso 1 1 calc R U . . .
C21 C 0.3046(2) 0.49583(13) 0.52245(18) 0.0506(5) Uani 1 1 d . . . . .
H21A H 0.243060 0.447117 0.516219 0.076 Uiso 1 1 calc R U . . .
H21B H 0.335353 0.499101 0.595145 0.076 Uiso 1 1 calc R U . . .
H21C H 0.373678 0.483187 0.475524 0.076 Uiso 1 1 calc R U . . .
C22 C 0.23735(18) 0.80723(12) 0.36412(14) 0.0386(4) Uani 1 1 d . . . . .
H22 H 0.308556 0.808756 0.321251 0.046 Uiso 1 1 calc R U . . .
C23 C 0.7288(2) 0.59617(19) 0.1536(2) 0.0650(6) Uani 1 1 d . . . . .
H23A H 0.699846 0.570069 0.086768 0.097 Uiso 1 1 calc R U . . .
H23B H 0.788286 0.554694 0.187077 0.097 Uiso 1 1 calc R U . . .
H23C H 0.768813 0.654786 0.140440 0.097 Uiso 1 1 calc R U . . .
H2O H 0.316(3) 0.465(2) 0.221(2) 0.085(9) Uiso 1 1 d . . . . .
N1 N 0.24659(14) 0.58380(9) 0.49287(11) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.16905(15) 0.87634(9) 0.36496(12) 0.0569(4) Uani 1 1 d . . . . .
O2 O 0.30331(12) 0.51353(9) 0.27269(11) 0.0448(3) 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'
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
O2 C1 C2 122.23(16) . . ?
O2 C1 C6 117.28(15) . . ?
C2 C1 C6 120.50(16) . . ?
C3 C2 C1 121.12(17) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.66(17) . . ?
C2 C3 C23 120.13(19) . . ?
C4 C3 C23 121.17(18) . . ?
C3 C4 C5 121.81(17) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 119.20(16) . . ?
C4 C5 C15 119.36(16) . . ?
C6 C5 C15 121.28(16) . . ?
C1 C6 C5 118.64(15) . . ?
C1 C6 C7 118.52(14) . . ?
C5 C6 C7 122.65(15) . . ?
N1 C7 C8 108.93(14) . . ?
N1 C7 C6 122.59(14) . . ?
C8 C7 C6 128.37(14) . . ?
C7 C8 C22 124.26(15) . . ?
C7 C8 C9 107.08(14) . . ?
C22 C8 C9 128.66(15) . . ?
C11 C9 C10 119.12(17) . . ?
C11 C9 C8 134.64(17) . . ?
C10 C9 C8 106.23(15) . . ?
N1 C10 C14 129.29(18) . . ?
N1 C10 C9 108.20(14) . . ?
C14 C10 C9 122.51(18) . . ?
C12 C11 C9 118.1(2) . . ?
C12 C11 H11 120.9 . . ?
C9 C11 H11 120.9 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C10 117.1(2) . . ?
C13 C14 H14 121.5 . . ?
C10 C14 H14 121.5 . . ?
C16 C15 C20 117.9(2) . . ?
C16 C15 C5 121.2(2) . . ?
C20 C15 C5 120.76(17) . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 121.3(2) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 C8 124.40(17) . . ?
O1 C22 H22 117.8 . . ?
C8 C22 H22 117.8 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 N1 C10 109.56(14) . . ?
C7 N1 C21 126.51(15) . . ?
C10 N1 C21 123.85(15) . . ?
C1 O2 H2O 109.9(17) . . ?
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 O2 1.356(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.404(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 C23 1.509(3) . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(2) . ?
C5 C15 1.487(3) . ?
C6 C7 1.481(2) . ?
C7 N1 1.357(2) . ?
C7 C8 1.395(2) . ?
C8 C22 1.415(2) . ?
C8 C9 1.445(2) . ?
C9 C11 1.400(3) . ?
C9 C10 1.400(2) . ?
C10 N1 1.392(2) . ?
C10 C14 1.393(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.389(3) . ?
C15 C20 1.390(3) . ?
C16 C17 1.390(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N1 1.454(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O1 1.231(2) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O2 H2O 0.96(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 179.09(17) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 C23 179.27(18) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C23 C3 C4 C5 -177.67(18) . . . . ?
C3 C4 C5 C6 -2.2(3) . . . . ?
C3 C4 C5 C15 173.18(17) . . . . ?
O2 C1 C6 C5 178.74(15) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
O2 C1 C6 C7 -6.1(2) . . . . ?
C2 C1 C6 C7 173.92(15) . . . . ?
C4 C5 C6 C1 2.8(2) . . . . ?
C15 C5 C6 C1 -172.54(16) . . . . ?
C4 C5 C6 C7 -172.21(15) . . . . ?
C15 C5 C6 C7 12.5(2) . . . . ?
C1 C6 C7 N1 66.5(2) . . . . ?
C5 C6 C7 N1 -118.48(18) . . . . ?
C1 C6 C7 C8 -109.34(19) . . . . ?
C5 C6 C7 C8 65.6(2) . . . . ?
N1 C7 C8 C22 178.95(16) . . . . ?
C6 C7 C8 C22 -4.7(3) . . . . ?
N1 C7 C8 C9 -1.01(18) . . . . ?
C6 C7 C8 C9 175.31(16) . . . . ?
C7 C8 C9 C11 -177.6(2) . . . . ?
C22 C8 C9 C11 2.4(3) . . . . ?
C7 C8 C9 C10 1.05(19) . . . . ?
C22 C8 C9 C10 -178.91(17) . . . . ?
C11 C9 C10 N1 178.19(16) . . . . ?
C8 C9 C10 N1 -0.71(19) . . . . ?
C11 C9 C10 C14 -1.1(3) . . . . ?
C8 C9 C10 C14 179.96(17) . . . . ?
C10 C9 C11 C12 0.6(3) . . . . ?
C8 C9 C11 C12 179.1(2) . . . . ?
C9 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C10 -0.5(4) . . . . ?
N1 C10 C14 C13 -178.13(19) . . . . ?
C9 C10 C14 C13 1.0(3) . . . . ?
C4 C5 C15 C16 49.2(3) . . . . ?
C6 C5 C15 C16 -135.5(2) . . . . ?
C4 C5 C15 C20 -126.2(2) . . . . ?
C6 C5 C15 C20 49.1(2) . . . . ?
C20 C15 C16 C17 -0.1(4) . . . . ?
C5 C15 C16 C17 -175.7(2) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C16 C15 C20 C19 0.0(3) . . . . ?
C5 C15 C20 C19 175.66(19) . . . . ?
C7 C8 C22 O1 -177.12(18) . . . . ?
C9 C8 C22 O1 2.8(3) . . . . ?
C8 C7 N1 C10 0.58(19) . . . . ?
C6 C7 N1 C10 -176.00(15) . . . . ?
C8 C7 N1 C21 -176.31(17) . . . . ?
C6 C7 N1 C21 7.1(3) . . . . ?
C14 C10 N1 C7 179.37(19) . . . . ?
C9 C10 N1 C7 0.11(19) . . . . ?
C14 C10 N1 C21 -3.6(3) . . . . ?
C9 C10 N1 C21 177.09(17) . . . . ?
