#------------------------------------------------------------------------------
#$Date: 2023-09-23 00:56:09 +0300 (Sat, 23 Sep 2023) $
#$Revision: 286470 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132149.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_7132149
loop_
_publ_author_name
'Bag, Debojyoti'
'Sawant, Sanghapal D.'
_publ_section_title
;
 Ag(I)-Catalyzed Dearomatizing Spirocyclization/Nucleophile Addition
 Cascade Reactions of Indole-tethered Ynones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03543C
_journal_year                    2023
_chemical_formula_sum            'C27 H22 N2 O'
_chemical_formula_weight         390.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-09-20 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.978(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.641(3)
_cell_length_b                   7.1425(6)
_cell_length_c                   15.2538(12)
_cell_measurement_reflns_used    9654
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.257
_cell_measurement_theta_min      2.744
_cell_volume                     4039.0(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12385
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.258
_diffrn_reflns_theta_min         2.712
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8507.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       Rectangle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0531
_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)+(0.0589P)²+0.9772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2941
_reflns_number_total             4339
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03543c2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7132149
_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.
;
loop_
_space_group_symop_operation_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_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 0.33253(4) 0.76658(19) 0.44998(8) 0.0603(4) Uani 1 1 d . . . . .
N2 N 0.36187(5) 0.8946(2) 0.85454(10) 0.0491(4) Uani 1 1 d . . . . .
H2 H 0.3529(6) 1.000(3) 0.8776(15) 0.074 Uiso 1 1 d . U . . .
N1 N 0.31039(4) 0.3817(2) 0.75605(10) 0.0455(4) Uani 1 1 d . . . . .
H1 H 0.3117(5) 0.342(3) 0.8148(15) 0.068 Uiso 1 1 d . U . . .
C14 C 0.31262(4) 0.2807(2) 0.61459(11) 0.0361(4) Uani 1 1 d . . . . .
C11 C 0.33953(4) 0.4411(2) 0.63298(10) 0.0347(4) Uani 1 1 d . . . . .
C10 C 0.32300(5) 0.6226(2) 0.58881(11) 0.0403(4) Uani 1 1 d . . . . .
H10A H 0.296721 0.607843 0.568366 0.048 Uiso 1 1 calc R U . . .
H10B H 0.327122 0.728783 0.631098 0.048 Uiso 1 1 calc R U . . .
C12 C 0.34604(4) 0.4411(2) 0.73757(11) 0.0367(4) Uani 1 1 d . . . . .
H12 H 0.363653 0.339040 0.758546 0.044 Uiso 1 1 calc R U . . .
C7 C 0.37304(4) 0.4151(2) 0.59098(11) 0.0366(4) Uani 1 1 d . . . . .
C15 C 0.30205(5) 0.1755(3) 0.53880(12) 0.0439(4) Uani 1 1 d . . . . .
H15 H 0.313111 0.193555 0.487992 0.053 Uiso 1 1 calc R U . . .
C13 C 0.29623(5) 0.2557(2) 0.68888(11) 0.0398(4) Uani 1 1 d . . . . .
C19 C 0.35932(5) 0.6152(2) 0.78603(11) 0.0399(4) Uani 1 1 d . . . . .
C22 C 0.39641(5) 0.6570(2) 0.82152(11) 0.0393(4) Uani 1 1 d . . . . .
C21 C 0.39692(5) 0.8334(3) 0.86359(11) 0.0412(4) Uani 1 1 d . . . . .
C6 C 0.40157(5) 0.2768(2) 0.61953(11) 0.0394(4) Uani 1 1 d . . . . .
C20 C 0.33965(5) 0.7621(3) 0.80867(12) 0.0477(5) Uani 1 1 d . . . . .
H20 H 0.314122 0.771413 0.794655 0.057 Uiso 1 1 calc R U . . .
C9 C 0.34195(5) 0.6550(2) 0.51128(11) 0.0433(4) Uani 1 1 d . . . . .
C16 C 0.27505(5) 0.0427(3) 0.53769(14) 0.0521(5) Uani 1 1 d . . . . .
H16 H 0.267738 -0.031875 0.486161 0.062 Uiso 1 1 calc R U . . .
C18 C 0.26886(5) 0.1248(3) 0.68782(14) 0.0519(5) Uani 1 1 d . . . . .
H18 H 0.257368 0.108193 0.738033 0.062 Uiso 1 1 calc R U . . .
C1 C 0.39450(5) 0.0986(3) 0.64904(12) 0.0482(5) Uani 1 1 d . . . . .
H1A H 0.370428 0.063837 0.652565 0.058 Uiso 1 1 calc R U . . .
C8 C 0.37298(5) 0.5317(2) 0.52204(12) 0.0448(4) Uani 1 1 d . . . . .
H8 H 0.390895 0.533312 0.485171 0.054 Uiso 1 1 calc R U . . .
C23 C 0.42912(5) 0.5648(3) 0.82126(13) 0.0486(5) Uani 1 1 d . . . . .
H23 H 0.429663 0.446019 0.793512 0.058 Uiso 1 1 calc R U . . .
C26 C 0.42870(6) 0.9222(3) 0.90329(12) 0.0488(5) Uani 1 1 d . . . . .
C17 C 0.25882(5) 0.0191(3) 0.61136(15) 0.0556(5) Uani 1 1 d . . . . .
H17 H 0.240296 -0.071880 0.609640 0.067 Uiso 1 1 calc R U . . .
C5 C 0.43729(5) 0.3231(3) 0.61637(14) 0.0559(5) Uani 1 1 d . . . . .
H5 H 0.442827 0.443820 0.596289 0.067 Uiso 1 1 calc R U . . .
C25 C 0.45998(6) 0.8255(3) 0.90187(14) 0.0595(6) Uani 1 1 d . . . . .
H25 H 0.482210 0.879861 0.929029 0.071 Uiso 1 1 calc R U . . .
C2 C 0.42215(6) -0.0281(3) 0.67324(13) 0.0624(6) Uani 1 1 d . . . . .
H2A H 0.416899 -0.150184 0.692126 0.075 Uiso 1 1 calc R U . . .
C27 C 0.42784(6) 1.1147(3) 0.94217(15) 0.0649(6) Uani 1 1 d . . . . .
H27A H 0.452557 1.157094 0.963942 0.097 Uiso 1 1 calc R U . . .
H27B H 0.414374 1.111546 0.991668 0.097 Uiso 1 1 calc R U . . .
H27C H 0.416043 1.201117 0.896301 0.097 Uiso 1 1 calc R U . . .
C24 C 0.46044(6) 0.6490(3) 0.86181(14) 0.0598(6) Uani 1 1 d . . . . .
H24 H 0.482804 0.586741 0.862766 0.072 Uiso 1 1 calc R U . . .
C3 C 0.45706(6) 0.0208(4) 0.67023(14) 0.0698(7) Uani 1 1 d . . . . .
H3 H 0.475985 -0.066588 0.687698 0.084 Uiso 1 1 calc R U . . .
C4 C 0.46469(6) 0.1962(4) 0.64197(16) 0.0717(7) Uani 1 1 d . . . . .
H4 H 0.488934 0.230276 0.640034 0.086 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'
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
C20 N2 C21 108.78(15) . . ?
C13 N1 C12 106.73(13) . . ?
C15 C14 C13 120.57(16) . . ?
C15 C14 C11 130.60(15) . . ?
C13 C14 C11 108.71(14) . . ?
C7 C11 C14 113.83(13) . . ?
C7 C11 C10 102.70(13) . . ?
C14 C11 C10 110.31(13) . . ?
C7 C11 C12 115.63(13) . . ?
C14 C11 C12 99.71(12) . . ?
C10 C11 C12 115.08(13) . . ?
C9 C10 C11 105.24(13) . . ?
N1 C12 C19 112.48(14) . . ?
N1 C12 C11 101.91(13) . . ?
C19 C12 C11 118.94(14) . . ?
C8 C7 C6 123.52(16) . . ?
C8 C7 C11 111.43(15) . . ?
C6 C7 C11 125.03(14) . . ?
C14 C15 C16 119.14(17) . . ?
C18 C13 C14 120.60(17) . . ?
C18 C13 N1 129.02(16) . . ?
C14 C13 N1 110.33(15) . . ?
C20 C19 C22 106.24(16) . . ?
C20 C19 C12 128.21(17) . . ?
C22 C19 C12 125.51(15) . . ?
C23 C22 C21 118.63(16) . . ?
C23 C22 C19 134.40(17) . . ?
C21 C22 C19 106.97(16) . . ?
N2 C21 C26 129.41(18) . . ?
N2 C21 C22 107.50(16) . . ?
C26 C21 C22 123.07(18) . . ?
C1 C6 C5 117.91(17) . . ?
C1 C6 C7 122.72(16) . . ?
C5 C6 C7 119.37(16) . . ?
C19 C20 N2 110.51(17) . . ?
O1 C9 C8 126.77(17) . . ?
O1 C9 C10 125.70(17) . . ?
C8 C9 C10 107.53(15) . . ?
C17 C16 C15 120.03(19) . . ?
C17 C18 C13 118.03(18) . . ?
C2 C1 C6 120.58(19) . . ?
C7 C8 C9 110.97(16) . . ?
C24 C23 C22 118.76(18) . . ?
C25 C26 C21 116.00(18) . . ?
C25 C26 C27 123.14(19) . . ?
C21 C26 C27 120.8(2) . . ?
C16 C17 C18 121.62(18) . . ?
C4 C5 C6 120.9(2) . . ?
C26 C25 C24 122.43(19) . . ?
C3 C2 C1 120.5(2) . . ?
C23 C24 C25 121.1(2) . . ?
C2 C3 C4 119.9(2) . . ?
C3 C4 C5 120.2(2) . . ?
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 C9 1.233(2) . ?
N2 C20 1.372(2) . ?
N2 C21 1.374(2) . ?
N1 C13 1.398(2) . ?
N1 C12 1.480(2) . ?
C14 C15 1.378(2) . ?
C14 C13 1.392(2) . ?
C14 C11 1.523(2) . ?
C11 C7 1.522(2) . ?
C11 C10 1.542(2) . ?
C11 C12 1.571(2) . ?
C10 C9 1.501(2) . ?
C12 C19 1.488(2) . ?
C7 C8 1.341(2) . ?
C7 C6 1.468(2) . ?
C15 C16 1.388(3) . ?
C13 C18 1.389(2) . ?
C19 C20 1.362(2) . ?
C19 C22 1.438(2) . ?
C22 C23 1.397(2) . ?
C22 C21 1.413(2) . ?
C21 C26 1.396(3) . ?
C6 C1 1.391(2) . ?
C6 C5 1.394(2) . ?
C9 C8 1.449(3) . ?
C16 C17 1.379(3) . ?
C18 C17 1.386(3) . ?
C1 C2 1.381(3) . ?
C23 C24 1.372(3) . ?
C26 C25 1.369(3) . ?
C26 C27 1.499(3) . ?
C5 C4 1.378(3) . ?
C25 C24 1.402(3) . ?
C2 C3 1.368(3) . ?
C3 C4 1.371(3) . ?
