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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/64/4036426.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_4036426
loop_
_publ_author_name
'Li, Ming'
'Kong, Xiang-Jing'
'Wen, Li-Rong'
_publ_section_title
;
 Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser
 Sulfide Contraction Reaction.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11999
_journal_page_last               12005
_journal_paper_doi               10.1021/acs.joc.5b01924
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C23 H17 N O2'
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.188(4)
_cell_length_b                   21.229(8)
_cell_length_c                   7.164(3)
_cell_measurement_reflns_used    5083
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4787
_cell_measurement_theta_min      1.8202
_cell_volume                     1701.5(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0097
_diffrn_orient_matrix_UB_12      0.1246
_diffrn_orient_matrix_UB_13      -0.0621
_diffrn_orient_matrix_UB_21      -0.0743
_diffrn_orient_matrix_UB_22      -0.0174
_diffrn_orient_matrix_UB_23      -0.0465
_diffrn_orient_matrix_UB_31      -0.0260
_diffrn_orient_matrix_UB_32      0.0191
_diffrn_orient_matrix_UB_33      0.0343
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6740
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         0.959
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       rod
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0857
_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)+(0.0034P)²+1.9444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.851
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                2744
_reflns_number_total             3579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5b01924_si_001.cif
_cod_data_source_block           a
_cod_database_code               4036426
_shelxl_version_number           2013-4
_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.
;
_diffrn_number_total             2273
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
O1 O 0.2308(3) 0.19693(16) 0.2822(6) 0.0240(8) Uani 1 1 d .
O2 O 0.2209(3) 0.38050(17) 0.0869(6) 0.0304(10) Uani 1 1 d .
N1 N 0.0962(4) 0.2769(2) 0.2067(7) 0.0255(11) Uani 1 1 d .
C1 C 0.2097(5) 0.2558(2) 0.2201(8) 0.0212(12) Uani 1 1 d .
C2 C 0.3141(5) 0.2876(2) 0.1829(8) 0.0233(13) Uani 1 1 d .
C3 C 0.4076(5) 0.2430(2) 0.2210(8) 0.0230(12) Uani 1 1 d .
H3 H 0.4891 0.2499 0.2058 0.028 Uiso 1 1 calc R
C4 C 0.3564(4) 0.1890(3) 0.2829(9) 0.0233(12) Uani 1 1 d .
C5 C -0.0092(5) 0.2499(3) 0.2809(8) 0.0242(12) Uani 1 1 d .
C6 C -0.0226(5) 0.1850(3) 0.3052(8) 0.0257(13) Uani 1 1 d .
H6 H 0.0362 0.1571 0.2652 0.031 Uiso 1 1 calc R
C7 C -0.1262(5) 0.1630(3) 0.3909(9) 0.0310(14) Uani 1 1 d .
H7 H -0.1356 0.1200 0.4099 0.037 Uiso 1 1 calc R
C8 C -0.2155(6) 0.2035(3) 0.4485(8) 0.0375(16) Uani 1 1 d .
H8 H -0.2833 0.1880 0.5079 0.045 Uiso 1 1 calc R
C9 C -0.2032(5) 0.2672(3) 0.4169(8) 0.0314(14) Uani 1 1 d .
H9 H -0.2637 0.2947 0.4526 0.038 Uiso 1 1 calc R
C10 C -0.1008(5) 0.2907(3) 0.3320(8) 0.0261(13) Uani 1 1 d .
H10 H -0.0935 0.3336 0.3093 0.031 Uiso 1 1 calc R
C11 C 0.3166(5) 0.3531(3) 0.1267(8) 0.0242(13) Uani 1 1 d .
C12 C 0.4317(5) 0.3883(2) 0.1195(8) 0.0241(13) Uani 1 1 d .
C13 C 0.5226(5) 0.3784(2) 0.2482(8) 0.0284(14) Uani 1 1 d .
H13 H 0.5137 0.3481 0.3410 0.034 Uiso 1 1 calc R
C14 C 0.6275(5) 0.4138(3) 0.2383(9) 0.0320(15) Uani 1 1 d .
H14 H 0.6883 0.4074 0.3248 0.038 Uiso 1 1 calc R
C15 C 0.6408(6) 0.4585(3) 0.0999(10) 0.0374(17) Uani 1 1 d .
H15 H 0.7111 0.4817 0.0926 0.045 Uiso 1 1 calc R
C16 C 0.5507(6) 0.4688(3) -0.0276(9) 0.0381(16) Uani 1 1 d .
H16 H 0.5604 0.4991 -0.1202 0.046 Uiso 1 1 calc R
C17 C 0.4454(5) 0.4343(3) -0.0187(9) 0.0317(14) Uani 1 1 d .
H17 H 0.3844 0.4417 -0.1042 0.038 Uiso 1 1 calc R
C18 C 0.4012(5) 0.1297(2) 0.3546(8) 0.0243(13) Uani 1 1 d .
C19 C 0.5230(5) 0.1171(3) 0.3453(8) 0.0277(13) Uani 1 1 d .
H19 H 0.5734 0.1450 0.2836 0.033 Uiso 1 1 calc R
C20 C 0.5701(6) 0.0636(3) 0.4265(9) 0.0325(15) Uani 1 1 d .
H20 H 0.6519 0.0562 0.4204 0.039 Uiso 1 1 calc R
C21 C 0.4969(6) 0.0207(3) 0.5167(9) 0.0345(15) Uani 1 1 d .
H21 H 0.5289 -0.0152 0.5718 0.041 Uiso 1 1 calc R
C22 C 0.3747(6) 0.0325(3) 0.5236(9) 0.0342(15) Uani 1 1 d .
H22 H 0.3246 0.0038 0.5827 0.041 Uiso 1 1 calc R
C23 C 0.3261(5) 0.0862(3) 0.4439(8) 0.0304(14) Uani 1 1 d .
H23 H 0.2441 0.0934 0.4496 0.036 Uiso 1 1 calc R
H1 H 0.096(5) 0.320(3) 0.159(9) 0.040(18) Uiso 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
C1 O1 C4 106.6(4)
C1 N1 C5 128.5(5)
O1 C1 N1 119.7(5)
O1 C1 C2 111.8(4)
N1 C1 C2 128.4(5)
C1 C2 C3 104.9(4)
C1 C2 C11 122.8(5)
C3 C2 C11 132.3(5)
C4 C3 C2 108.2(5)
O1 C4 C18 116.7(4)
C3 C4 O1 108.5(4)
C3 C4 C18 134.8(5)
C6 C5 N1 122.5(5)
C10 C5 N1 117.5(5)
C10 C5 C6 120.1(5)
C7 C6 C5 118.4(5)
C8 C7 C6 121.7(6)
C9 C8 C7 119.3(6)
C8 C9 C10 120.4(6)
C9 C10 C5 120.1(5)
O2 C11 C2 119.5(5)
O2 C11 C12 120.0(5)
C2 C11 C12 120.5(5)
C13 C12 C11 122.3(5)
C13 C12 C17 119.6(5)
C17 C12 C11 118.0(5)
C12 C13 C14 120.0(5)
C15 C14 C13 119.9(6)
C16 C15 C14 120.4(6)
C15 C16 C17 120.4(6)
C16 C17 C12 119.6(6)
C19 C18 C4 119.3(5)
C19 C18 C23 118.9(5)
C23 C18 C4 121.7(5)
C20 C19 C18 120.8(6)
C19 C20 C21 120.8(6)
C20 C21 C22 118.7(6)
C23 C22 C21 121.2(6)
C22 C23 C18 119.6(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.347(6)
O1 C4 1.416(6)
O2 C11 1.251(6)
N1 C1 1.351(7)
N1 C5 1.414(7)
C1 C2 1.376(7)
C2 C3 1.437(7)
C2 C11 1.448(7)
C3 C4 1.356(7)
C4 C18 1.449(7)
C5 C6 1.398(7)
C5 C10 1.390(7)
C6 C7 1.392(7)
C7 C8 1.381(8)
C8 C9 1.379(8)
C9 C10 1.389(8)
C11 C12 1.489(7)
C12 C13 1.390(8)
C12 C17 1.399(8)
C13 C14 1.396(7)
C14 C15 1.379(9)
C15 C16 1.379(9)
C16 C17 1.388(8)
C18 C19 1.390(8)
C18 C23 1.403(7)
C19 C20 1.380(8)
C20 C21 1.384(8)
C21 C22 1.391(9)
C22 C23 1.387(8)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O2 0.97(6) 1.97(6) 2.742(6) 135(5)
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
O1 C1 C2 C3 1.8(6)
O1 C1 C2 C11 -175.6(5)
O1 C4 C18 C19 174.9(5)
O1 C4 C18 C23 -9.1(9)
O2 C11 C12 C13 142.6(6)
O2 C11 C12 C17 -35.1(8)
N1 C1 C2 C3 179.7(6)
N1 C1 C2 C11 2.3(9)
N1 C5 C6 C7 175.7(5)
N1 C5 C10 C9 -175.8(5)
C1 O1 C4 C3 -0.1(7)
C1 O1 C4 C18 176.8(5)
C1 N1 C5 C6 -30.4(9)
C1 N1 C5 C10 148.9(6)
C1 C2 C3 C4 -1.9(7)
C1 C2 C11 O2 -9.3(9)
C1 C2 C11 C12 169.6(5)
C2 C3 C4 O1 1.3(7)
C2 C3 C4 C18 -174.9(6)
C2 C11 C12 C13 -36.3(8)
C2 C11 C12 C17 146.0(5)
C3 C2 C11 O2 174.0(6)
C3 C2 C11 C12 -7.1(9)
C3 C4 C18 C19 -9.1(11)
C3 C4 C18 C23 166.9(6)
C4 O1 C1 N1 -179.2(5)
C4 O1 C1 C2 -1.1(6)
C4 C18 C19 C20 174.4(6)
C4 C18 C23 C22 -174.8(6)
C5 N1 C1 O1 12.6(9)
C5 N1 C1 C2 -165.2(6)
C5 C6 C7 C8 1.1(9)
C6 C5 C10 C9 3.6(9)
C6 C7 C8 C9 1.4(9)
C7 C8 C9 C10 -1.5(9)
C8 C9 C10 C5 -1.0(9)
C10 C5 C6 C7 -3.6(9)
C11 C2 C3 C4 175.3(6)
C11 C12 C13 C14 -178.2(5)
C11 C12 C17 C16 178.8(5)
C12 C13 C14 C15 -0.3(8)
C13 C12 C17 C16 1.1(8)
C13 C14 C15 C16 0.7(9)
C14 C15 C16 C17 -0.2(9)
C15 C16 C17 C12 -0.7(9)
C17 C12 C13 C14 -0.6(8)
C18 C19 C20 C21 1.0(9)
C19 C18 C23 C22 1.2(9)
C19 C20 C21 C22 0.2(10)
C20 C21 C22 C23 -0.7(10)
C21 C22 C23 C18 0.0(9)
C23 C18 C19 C20 -1.7(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132553624
