#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:23:05 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286191 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159483.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_7159483
loop_
_publ_author_name
'Reddy, Chada Raji'
'Ajaykumar, Uprety'
'Patil, Amol D.'
'Ramesh, Remya'
_publ_section_title
;
 ipso-Cyclization of unactivated biaryl ynones leading to
 thio-functionalized spirocyclic enones.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6379
_journal_page_last               6388
_journal_paper_doi               10.1039/d3ob00974b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C26 H15 N O2 S'
_chemical_formula_sum            'C26 H15 N O2 S'
_chemical_formula_weight         405.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-06-20 deposited with the CCDC.	2023-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                93.071(2)
_cell_angle_beta                 104.114(2)
_cell_angle_gamma                110.0625(17)
_cell_formula_units_Z            2
_cell_length_a                   9.0366(6)
_cell_length_b                   9.9845(6)
_cell_length_c                   12.3996(8)
_cell_measurement_reflns_used    8021
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.60
_cell_volume                     1007.52(11)
_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 0.990
_diffrn_measured_fraction_theta_max 0.992
_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  0.0589
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18080
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.605
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0526
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3435
_reflns_number_total             4584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00974b2.cif
_cod_data_source_block           KB327_0m
_cod_depositor_comments          'Adding full bibliography for 7159483.cif.'
_cod_database_code               7159483
_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   0.968
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.18194(5) 0.45461(5) 0.01574(4) 0.05072(19) Uani 1 1 d . . . . .
O1 O 0.8598(3) 1.12858(16) 0.44151(16) 0.1006(6) Uani 1 1 d . . . . .
O2 O 0.41628(18) 0.30773(13) 0.06207(12) 0.0638(4) Uani 1 1 d . . . . .
N2 N 0.0237(3) 0.2441(2) 0.13515(19) 0.0854(6) Uani 1 1 d . . . . .
C1 C 0.1781(3) 0.9403(2) 0.13839(19) 0.0670(6) Uani 1 1 d . . . . .
H1 H 0.122794 1.004056 0.132051 0.080 Uiso 1 1 calc R U . . .
C2 C 0.1365(2) 0.8280(2) 0.19842(17) 0.0627(5) Uani 1 1 d . . . . .
H3 H 0.051315 0.814448 0.231360 0.075 Uiso 1 1 calc R U . . .
C3 C 0.2205(2) 0.7360(2) 0.20974(16) 0.0521(4) Uani 1 1 d . . . . .
H4 H 0.192369 0.660939 0.251211 0.063 Uiso 1 1 calc R U . . .
C4 C 0.34644(19) 0.75301(17) 0.16044(13) 0.0386(4) Uani 1 1 d . . . . .
C5 C 0.60913(19) 0.71339(16) 0.26065(13) 0.0356(3) Uani 1 1 d . . . . .
C6 C 0.5855(2) 0.75627(18) 0.37418(13) 0.0408(4) Uani 1 1 d . . . . .
C7 C 0.6695(2) 0.8944(2) 0.43403(15) 0.0527(5) Uani 1 1 d . . . . .
C8 C 0.6481(4) 0.9259(3) 0.53892(19) 0.0808(7) Uani 1 1 d . . . . .
H7 H 0.705678 1.017804 0.579909 0.097 Uiso 1 1 calc R U . . .
C9 C 0.5437(4) 0.8235(3) 0.5822(2) 0.0848(8) Uani 1 1 d . . . . .
H2 H 0.529858 0.846411 0.651838 0.102 Uiso 1 1 calc R U . . .
C10 C 0.7828(3) 1.0081(2) 0.38814(18) 0.0620(5) Uani 1 1 d . . . . .
C11 C 0.7973(2) 0.9702(2) 0.27770(17) 0.0543(5) Uani 1 1 d . . . . .
H5 H 0.864482 1.040945 0.246611 0.065 Uiso 1 1 calc R U . . .
C12 C 0.71903(19) 0.83915(17) 0.21934(14) 0.0413(4) Uani 1 1 d . . . . .
H6 H 0.732432 0.823343 0.148338 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4590(3) 0.6865(3) 0.52289(17) 0.0685(6) Uani 1 1 d . . . . .
H9 H 0.387098 0.617324 0.552096 0.082 Uiso 1 1 calc R U . . .
C14 C 0.4810(2) 0.6519(2) 0.41981(15) 0.0503(4) Uani 1 1 d . . . . .
H8 H 0.425872 0.558647 0.380810 0.060 Uiso 1 1 calc R U . . .
C15 C 0.69555(19) 0.60522(17) 0.27596(13) 0.0384(4) Uani 1 1 d . . . . .
C16 C 0.6313(2) 0.46996(17) 0.21041(13) 0.0387(4) Uani 1 1 d . . . . .
C17 C 0.4716(2) 0.42239(16) 0.12518(13) 0.0412(4) Uani 1 1 d . . . . .
C18 C 0.37965(18) 0.52032(16) 0.11736(12) 0.0369(4) Uani 1 1 d . . . . .
C19 C 0.0875(2) 0.3277(2) 0.08621(17) 0.0538(5) Uani 1 1 d . . . . .
C20 C 0.7194(2) 0.3770(2) 0.22575(16) 0.0521(5) Uani 1 1 d . . . . .
H13 H 0.676436 0.286540 0.182079 0.062 Uiso 1 1 calc R U . . .
C21 C 0.8689(3) 0.4202(2) 0.30535(17) 0.0595(5) Uani 1 1 d . . . . .
H12 H 0.926990 0.358739 0.315502 0.071 Uiso 1 1 calc R U . . .
C22 C 0.9330(2) 0.5544(2) 0.37017(17) 0.0567(5) Uani 1 1 d . . . . .
H10 H 1.034452 0.583319 0.423613 0.068 Uiso 1 1 calc R U . . .
C23 C 0.8474(2) 0.6459(2) 0.35616(15) 0.0490(4) Uani 1 1 d . . . . .
H11 H 0.891453 0.735827 0.400718 0.059 Uiso 1 1 calc R U . . .
C24 C 0.3839(2) 0.8638(2) 0.09786(17) 0.0560(5) Uani 1 1 d . . . . .
H14 H 0.465516 0.875472 0.061836 0.067 Uiso 1 1 calc R U . . .
C25 C 0.2999(3) 0.9580(2) 0.0885(2) 0.0707(6) Uani 1 1 d . . . . .
H15 H 0.327568 1.033762 0.047581 0.085 Uiso 1 1 calc R U . . .
C26 C 0.43939(19) 0.65425(16) 0.17493(12) 0.0343(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'
S S 0.1246 0.1234 '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
C19 S1 C18 96.65(8) . . ?
C25 C1 C2 119.84(18) . . ?
C25 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.01(18) . . ?
C3 C2 H3 120.0 . . ?
C1 C2 H3 120.0 . . ?
C2 C3 C4 121.07(18) . . ?
C2 C3 H4 119.5 . . ?
C4 C3 H4 119.5 . . ?
C24 C4 C3 118.28(15) . . ?
C24 C4 C26 120.95(14) . . ?
C3 C4 C26 120.78(15) . . ?
C12 C5 C15 105.98(12) . . ?
C12 C5 C26 108.56(12) . . ?
C15 C5 C26 114.02(12) . . ?
C12 C5 C6 112.82(13) . . ?
C15 C5 C6 108.29(12) . . ?
C26 C5 C6 107.30(12) . . ?
C7 C6 C14 119.38(16) . . ?
C7 C6 C5 121.72(15) . . ?
C14 C6 C5 118.86(14) . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 C10 120.76(16) . . ?
C8 C7 C10 119.96(18) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H7 119.5 . . ?
C7 C8 H7 119.5 . . ?
C8 C9 C13 120.1(2) . . ?
C8 C9 H2 119.9 . . ?
C13 C9 H2 119.9 . . ?
O1 C10 C11 121.4(2) . . ?
O1 C10 C7 121.0(2) . . ?
C11 C10 C7 117.55(15) . . ?
C12 C11 C10 122.70(18) . . ?
C12 C11 H5 118.7 . . ?
C10 C11 H5 118.7 . . ?
C11 C12 C5 124.21(16) . . ?
C11 C12 H6 117.9 . . ?
C5 C12 H6 117.9 . . ?
C9 C13 C14 120.0(2) . . ?
C9 C13 H9 120.0 . . ?
C14 C13 H9 120.0 . . ?
C13 C14 C6 120.28(18) . . ?
C13 C14 H8 119.9 . . ?
C6 C14 H8 119.9 . . ?
C16 C15 C23 118.78(14) . . ?
C16 C15 C5 122.55(13) . . ?
C23 C15 C5 118.63(14) . . ?
C15 C16 C20 119.94(15) . . ?
C15 C16 C17 120.69(13) . . ?
C20 C16 C17 119.37(15) . . ?
O2 C17 C16 122.15(14) . . ?
O2 C17 C18 120.70(15) . . ?
C16 C17 C18 117.14(13) . . ?
C26 C18 C17 124.24(14) . . ?
C26 C18 S1 120.09(11) . . ?
C17 C18 S1 115.52(11) . . ?
N2 C19 S1 178.68(19) . . ?
C21 C20 C16 119.96(17) . . ?
C21 C20 H13 120.0 . . ?
C16 C20 H13 120.0 . . ?
C20 C21 C22 120.15(15) . . ?
C20 C21 H12 119.9 . . ?
C22 C21 H12 119.9 . . ?
C23 C22 C21 120.34(17) . . ?
C23 C22 H10 119.8 . . ?
C21 C22 H10 119.8 . . ?
C22 C23 C15 120.83(17) . . ?
C22 C23 H11 119.6 . . ?
C15 C23 H11 119.6 . . ?
C4 C24 C25 120.22(18) . . ?
C4 C24 H14 119.9 . . ?
C25 C24 H14 119.9 . . ?
C1 C25 C24 120.5(2) . . ?
C1 C25 H15 119.7 . . ?
C24 C25 H15 119.7 . . ?
C18 C26 C4 122.79(14) . . ?
C18 C26 C5 120.94(13) . . ?
C4 C26 C5 116.27(12) . . ?
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
S1 C19 1.685(2) . ?
S1 C18 1.7943(15) . ?
O1 C10 1.219(2) . ?
O2 C17 1.2221(18) . ?
N2 C19 1.137(3) . ?
C1 C25 1.356(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(3) . ?
C2 H3 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H4 0.9300 . ?
C4 C24 1.380(2) . ?
C4 C26 1.491(2) . ?
C5 C12 1.512(2) . ?
C5 C15 1.530(2) . ?
C5 C26 1.532(2) . ?
C5 C6 1.535(2) . ?
C6 C7 1.388(2) . ?
C6 C14 1.395(2) . ?
C7 C8 1.396(3) . ?
C7 C10 1.489(3) . ?
C8 C9 1.366(4) . ?
C8 H7 0.9300 . ?
C9 C13 1.377(3) . ?
C9 H2 0.9300 . ?
C10 C11 1.450(3) . ?
C11 C12 1.323(2) . ?
C11 H5 0.9300 . ?
C12 H6 0.9300 . ?
C13 C14 1.384(3) . ?
C13 H9 0.9300 . ?
C14 H8 0.9300 . ?
C15 C16 1.391(2) . ?
C15 C23 1.395(2) . ?
C16 C20 1.408(2) . ?
C16 C17 1.469(2) . ?
C17 C18 1.478(2) . ?
C18 C26 1.343(2) . ?
C20 C21 1.375(3) . ?
C20 H13 0.9300 . ?
C21 C22 1.379(3) . ?
C21 H12 0.9300 . ?
C22 C23 1.377(2) . ?
C22 H10 0.9300 . ?
C23 H11 0.9300 . ?
C24 C25 1.390(3) . ?
C24 H14 0.9300 . ?
C25 H15 0.9300 . ?
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
C25 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C24 -1.0(3) . . . . ?
C2 C3 C4 C26 178.82(16) . . . . ?
C12 C5 C6 C7 -5.0(2) . . . . ?
C15 C5 C6 C7 111.97(17) . . . . ?
C26 C5 C6 C7 -124.53(16) . . . . ?
C12 C5 C6 C14 177.22(13) . . . . ?
C15 C5 C6 C14 -65.80(18) . . . . ?
C26 C5 C6 C14 57.70(17) . . . . ?
C14 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 -177.51(18) . . . . ?
C14 C6 C7 C10 179.59(16) . . . . ?
C5 C6 C7 C10 1.8(3) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C10 C7 C8 C9 179.5(2) . . . . ?
C7 C8 C9 C13 0.7(4) . . . . ?
C6 C7 C10 O1 -178.23(19) . . . . ?
C8 C7 C10 O1 1.1(3) . . . . ?
C6 C7 C10 C11 2.0(3) . . . . ?
C8 C7 C10 C11 -178.6(2) . . . . ?
O1 C10 C11 C12 177.9(2) . . . . ?
C7 C10 C11 C12 -2.3(3) . . . . ?
C10 C11 C12 C5 -1.4(3) . . . . ?
C15 C5 C12 C11 -113.45(18) . . . . ?
C26 C5 C12 C11 123.68(17) . . . . ?
C6 C5 C12 C11 4.9(2) . . . . ?
C8 C9 C13 C14 0.7(4) . . . . ?
C9 C13 C14 C6 -1.7(3) . . . . ?
C7 C6 C14 C13 1.2(3) . . . . ?
C5 C6 C14 C13 178.99(16) . . . . ?
C12 C5 C15 C16 -113.96(16) . . . . ?
C26 C5 C15 C16 5.4(2) . . . . ?
C6 C5 C15 C16 124.74(16) . . . . ?
C12 C5 C15 C23 63.77(18) . . . . ?
C26 C5 C15 C23 -176.89(13) . . . . ?
C6 C5 C15 C23 -57.53(19) . . . . ?
C23 C15 C16 C20 0.0(2) . . . . ?
C5 C15 C16 C20 177.73(15) . . . . ?
C23 C15 C16 C17 179.82(15) . . . . ?
C5 C15 C16 C17 -2.5(2) . . . . ?
C15 C16 C17 O2 175.78(16) . . . . ?
C20 C16 C17 O2 -4.4(2) . . . . ?
C15 C16 C17 C18 -3.5(2) . . . . ?
C20 C16 C17 C18 176.32(14) . . . . ?
O2 C17 C18 C26 -172.51(16) . . . . ?
C16 C17 C18 C26 6.8(2) . . . . ?
O2 C17 C18 S1 3.0(2) . . . . ?
C16 C17 C18 S1 -177.73(11) . . . . ?
C19 S1 C18 C26 -112.84(14) . . . . ?
C19 S1 C18 C17 71.47(13) . . . . ?
C15 C16 C20 C21 -0.1(3) . . . . ?
C17 C16 C20 C21 -179.93(15) . . . . ?
C16 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C15 -0.5(3) . . . . ?
C16 C15 C23 C22 0.3(3) . . . . ?
C5 C15 C23 C22 -177.53(16) . . . . ?
C3 C4 C24 C25 2.1(3) . . . . ?
C26 C4 C24 C25 -177.73(18) . . . . ?
C2 C1 C25 C24 -0.3(3) . . . . ?
C4 C24 C25 C1 -1.5(3) . . . . ?
C17 C18 C26 C4 176.67(14) . . . . ?
S1 C18 C26 C4 1.4(2) . . . . ?
C17 C18 C26 C5 -3.7(2) . . . . ?
S1 C18 C26 C5 -178.97(10) . . . . ?
C24 C4 C26 C18 -102.5(2) . . . . ?
C3 C4 C26 C18 77.7(2) . . . . ?
C24 C4 C26 C5 77.87(19) . . . . ?
C3 C4 C26 C5 -101.99(18) . . . . ?
C12 C5 C26 C18 115.56(15) . . . . ?
C15 C5 C26 C18 -2.3(2) . . . . ?
C6 C5 C26 C18 -122.23(15) . . . . ?
C12 C5 C26 C4 -64.77(16) . . . . ?
C15 C5 C26 C4 177.36(12) . . . . ?
C6 C5 C26 C4 57.44(16) . . . . ?
