#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:36:35 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296682 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160138.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_7160138
loop_
_publ_author_name
'Barranco, Stefano'
'Pagnanini, Alessio'
'Cuccu, Federico'
'Caboni, Pierluigi'
'Guillot, Régis'
'Aitken, David J.'
'Frongia, Angelo'
_publ_section_title
;
 Substrate-dependent regiodivergence in [3 + 2] annulation reactions of
 2-(phenacylethylidene)cyclobutanones with thioureas.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8048
_journal_page_last               8053
_journal_paper_doi               10.1039/d4ob01103a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H20 N2 O2 S'
_chemical_formula_sum            'C20 H20 N2 O2 S'
_chemical_formula_weight         352.44
_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
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-06-10 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                99.849(8)
_cell_angle_beta                 101.129(8)
_cell_angle_gamma                117.442(8)
_cell_formula_units_Z            4
_cell_length_a                   11.754(3)
_cell_length_b                   11.915(3)
_cell_length_c                   15.389(4)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.44
_cell_volume                     1791.1(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker VENTURE PHOTONIII c7'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1082
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            137955
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.039
_diffrn_reflns_theta_min         2.014
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_correction_T_min  0.8814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX4'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         11402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0495
_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)+(0.0644P)²+0.2251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7095
_reflns_number_total             11402
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01103a2.cif
_cod_data_source_block           6e
_cod_depositor_comments
'Adding full bibliography for 7160135--7160138.cif.'
_cod_original_cell_volume        1791.1(7)
_cod_database_code               7160138
_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   0.987
_shelx_estimated_absorpt_t_max   0.992
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 -0.09047(4) 0.03371(5) 0.27813(3) 0.04030(12) Uani 1 1 d . . . . .
S2 S 0.71504(4) 0.45745(5) 0.71345(3) 0.04029(12) Uani 1 1 d . . . . .
O1 O 0.00506(15) -0.07738(14) 0.13880(9) 0.0525(3) Uani 1 1 d . . . . .
O2 O 0.26733(12) 0.28483(12) 0.43565(9) 0.0419(3) Uani 1 1 d . . . . .
H200 H 0.325762 0.292747 0.481310 0.063 Uiso 1 1 calc R U . . .
O3 O 1.00596(15) 0.62628(14) 0.83482(10) 0.0599(4) Uani 1 1 d . . . . .
O4 O 0.76462(13) 0.20672(12) 0.56823(8) 0.0422(3) Uani 1 1 d . . . . .
H400 H 0.786777 0.188901 0.521298 0.063 Uiso 1 1 calc R U . . .
N1 N 0.04841(13) 0.19130(14) 0.44558(9) 0.0359(3) Uani 1 1 d . . . . .
N2 N -0.17523(13) 0.13883(14) 0.40364(9) 0.0332(3) Uani 1 1 d . . . . .
N3 N 0.62085(14) 0.29113(17) 0.54934(11) 0.0516(4) Uani 1 1 d . . . . .
N4 N 0.46230(13) 0.33093(15) 0.59370(10) 0.0396(3) Uani 1 1 d . . . . .
C1 C 0.18231(17) 0.05844(18) 0.08728(11) 0.0374(4) Uani 1 1 d . . . . .
C2 C 0.28706(19) 0.1843(2) 0.09686(13) 0.0457(4) Uani 1 1 d . . . . .
H2 H 0.310574 0.257166 0.147584 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3571(2) 0.2039(2) 0.03283(14) 0.0531(5) Uani 1 1 d . . . . .
H3 H 0.427655 0.290088 0.038979 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3236(2) 0.0968(2) -0.04040(14) 0.0561(5) Uani 1 1 d . . . . .
H4 H 0.372184 0.109683 -0.083999 0.067 Uiso 1 1 calc R U . . .
C5 C 0.2206(2) -0.0279(2) -0.05025(13) 0.0508(5) Uani 1 1 d . . . . .
H5 H 0.198685 -0.100525 -0.100523 0.061 Uiso 1 1 calc R U . . .
C6 C 0.14895(19) -0.0483(2) 0.01202(12) 0.0438(4) Uani 1 1 d . . . . .
H6 H 0.076978 -0.134518 0.004197 0.053 Uiso 1 1 calc R U . . .
C7 C 0.10590(18) 0.03110(18) 0.15491(12) 0.0384(4) Uani 1 1 d . . . . .
C8 C 0.15547(18) 0.13705(18) 0.24588(12) 0.0402(4) Uani 1 1 d . . . . .
H8A H 0.253984 0.176958 0.273289 0.048 Uiso 1 1 calc R U . . .
H8B H 0.138366 0.207919 0.234219 0.048 Uiso 1 1 calc R U . . .
C9 C 0.08539(15) 0.07996(16) 0.31329(10) 0.0318(3) Uani 1 1 d . . . . .
C10 C -0.07689(15) 0.13018(15) 0.38431(10) 0.0289(3) Uani 1 1 d . . . . .
C11 C 0.14785(15) 0.16646(16) 0.41708(10) 0.0300(3) Uani 1 1 d . . . . .
C12 C 0.1117(2) -0.0263(2) 0.34345(13) 0.0505(5) Uani 1 1 d . . . . .
H12A H 0.028917 -0.114064 0.326781 0.061 Uiso 1 1 calc R U . . .
H12B H 0.182629 -0.034610 0.322382 0.061 Uiso 1 1 calc R U . . .
C13 C 0.16077(18) 0.05457(19) 0.44675(12) 0.0417(4) Uani 1 1 d . . . . .
H13A H 0.098872 0.011839 0.481661 0.050 Uiso 1 1 calc R U . . .
H13B H 0.254454 0.081153 0.479994 0.050 Uiso 1 1 calc R U . . .
C14 C -0.29905(15) 0.08061(16) 0.33073(11) 0.0327(3) Uani 1 1 d . . . . .
C15 C -0.41392(18) -0.02668(18) 0.33461(14) 0.0465(4) Uani 1 1 d . . . . .
H15 H -0.407878 -0.066242 0.382612 0.056 Uiso 1 1 calc R U . . .
C16 C -0.5370(2) -0.0761(2) 0.26888(17) 0.0625(6) Uani 1 1 d . . . . .
H16 H -0.615089 -0.149591 0.272007 0.075 Uiso 1 1 calc R U . . .
C17 C -0.5475(2) -0.0199(2) 0.19888(15) 0.0620(6) Uani 1 1 d . . . . .
H17 H -0.632536 -0.054157 0.154023 0.074 Uiso 1 1 calc R U . . .
C18 C -0.4347(2) 0.0858(2) 0.19439(13) 0.0540(5) Uani 1 1 d . . . . .
H18 H -0.441640 0.124503 0.146016 0.065 Uiso 1 1 calc R U . . .
C19 C -0.31010(18) 0.13686(18) 0.25990(12) 0.0414(4) Uani 1 1 d . . . . .
H19 H -0.232423 0.210298 0.256260 0.050 Uiso 1 1 calc R U . . .
C20 C 0.08360(18) 0.2688(2) 0.54030(12) 0.0479(5) Uani 1 1 d . . . . .
H20A H 0.137346 0.245639 0.582502 0.072 Uiso 1 1 calc R U . . .
H20B H 0.001075 0.249777 0.556216 0.072 Uiso 1 1 calc R U . . .
H20C H 0.136161 0.363301 0.546185 0.072 Uiso 1 1 calc R U . . .
C21 C 1.09901(16) 0.51347(18) 0.90584(12) 0.0390(4) Uani 1 1 d . . . . .
C22 C 1.08949(18) 0.39365(19) 0.90842(13) 0.0441(4) Uani 1 1 d . . . . .
H22 H 1.021136 0.314345 0.861509 0.053 Uiso 1 1 calc R U . . .
C23 C 1.1791(2) 0.3887(2) 0.97902(13) 0.0505(5) Uani 1 1 d . . . . .
H23 H 1.170922 0.306072 0.980745 0.061 Uiso 1 1 calc R U . . .
C24 C 1.2794(2) 0.5032(2) 1.04631(13) 0.0559(5) Uani 1 1 d . . . . .
H24 H 1.341871 0.499819 1.093728 0.067 Uiso 1 1 calc R U . . .
C25 C 1.2897(2) 0.6231(2) 1.04513(14) 0.0601(6) Uani 1 1 d . . . . .
H25 H 1.358803 0.702026 1.092056 0.072 Uiso 1 1 calc R U . . .
C26 C 1.1996(2) 0.6287(2) 0.97571(13) 0.0517(5) Uani 1 1 d . . . . .
H26 H 1.206413 0.711237 0.975668 0.062 Uiso 1 1 calc R U . . .
C27 C 1.00820(16) 0.52449(18) 0.82958(12) 0.0405(4) Uani 1 1 d . . . . .
C28 C 0.92146(17) 0.40615(18) 0.74357(13) 0.0438(4) Uani 1 1 d . . . . .
H28A H 0.980433 0.382928 0.716452 0.053 Uiso 1 1 calc R U . . .
H28B H 0.861130 0.329449 0.761584 0.053 Uiso 1 1 calc R U . . .
C29 C 0.83673(15) 0.43092(16) 0.67066(11) 0.0330(3) Uani 1 1 d . . . . .
C30 C 0.58261(15) 0.35062(16) 0.61065(11) 0.0324(3) Uani 1 1 d . . . . .
C31 C 0.75943(14) 0.32189(16) 0.57460(11) 0.0306(3) Uani 1 1 d . . . . .
C32 C 0.9129(2) 0.5297(2) 0.62028(15) 0.0557(5) Uani 1 1 d . . . . .
H32A H 0.888475 0.598774 0.619401 0.067 Uiso 1 1 calc R U . . .
H32B H 1.011976 0.570022 0.643247 0.067 Uiso 1 1 calc R U . . .
C33 C 0.8460(2) 0.4193(2) 0.52891(14) 0.0495(5) Uani 1 1 d . . . . .
H33A H 0.909058 0.396762 0.507238 0.059 Uiso 1 1 calc R U . . .
H33B H 0.793041 0.434668 0.478996 0.059 Uiso 1 1 calc R U . . .
C34 C 0.43215(15) 0.39767(18) 0.66311(12) 0.0386(4) Uani 1 1 d . . . . .
C35 C 0.4431(2) 0.5174(2) 0.66260(16) 0.0577(5) Uani 1 1 d . . . . .
H35 H 0.479701 0.560261 0.619781 0.069 Uiso 1 1 calc R U . . .
C36 C 0.4003(2) 0.5755(3) 0.7251(2) 0.0778(8) Uani 1 1 d . . . . .
H36 H 0.407874 0.658341 0.724749 0.093 Uiso 1 1 calc R U . . .
C37 C 0.3474(2) 0.5142(3) 0.78695(19) 0.0860(10) Uani 1 1 d . . . . .
H37 H 0.318086 0.554109 0.829341 0.103 Uiso 1 1 calc R U . . .
C38 C 0.3372(3) 0.3958(3) 0.78739(18) 0.0819(8) Uani 1 1 d . . . . .
H38 H 0.300447 0.353209 0.830292 0.098 Uiso 1 1 calc R U . . .
C39 C 0.3796(2) 0.3368(3) 0.72618(15) 0.0597(6) Uani 1 1 d . . . . .
H39 H 0.372651 0.254501 0.727440 0.072 Uiso 1 1 calc R U . . .
C40 C 0.52870(19) 0.2013(2) 0.45814(14) 0.0643(7) Uani 1 1 d . . . . .
H40A H 0.579922 0.204561 0.414412 0.097 Uiso 1 1 calc R U . . .
H40B H 0.463592 0.227977 0.436471 0.097 Uiso 1 1 calc R U . . .
H40C H 0.480566 0.110775 0.462140 0.097 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 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 '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
C10 S1 C9 93.90(7) . . ?
C30 S2 C29 92.88(7) . . ?
C10 N1 C20 123.08(13) . . ?
C10 N1 C11 117.71(13) . . ?
C20 N1 C11 118.92(12) . . ?
C10 N2 C14 118.04(13) . . ?
C30 N3 C31 118.45(14) . . ?
C30 N3 C40 122.14(14) . . ?
C31 N3 C40 119.38(14) . . ?
C30 N4 C34 118.40(14) . . ?
C2 C1 C6 119.15(17) . . ?
C2 C1 C7 122.66(16) . . ?
C6 C1 C7 118.16(17) . . ?
C3 C2 C1 120.34(18) . . ?
C2 C3 C4 119.6(2) . . ?
C5 C4 C3 120.47(19) . . ?
C6 C5 C4 120.54(19) . . ?
C5 C6 C1 119.92(19) . . ?
O1 C7 C1 120.60(16) . . ?
O1 C7 C8 119.76(16) . . ?
C1 C7 C8 119.62(16) . . ?
C9 C8 C7 111.05(15) . . ?
C8 C9 C12 115.10(14) . . ?
C8 C9 C11 117.37(14) . . ?
C12 C9 C11 88.87(12) . . ?
C8 C9 S1 111.96(11) . . ?
C12 C9 S1 114.64(13) . . ?
C11 C9 S1 106.87(10) . . ?
N2 C10 N1 123.22(14) . . ?
N2 C10 S1 124.63(11) . . ?
N1 C10 S1 112.10(11) . . ?
O2 C11 N1 110.45(13) . . ?
O2 C11 C13 116.35(13) . . ?
N1 C11 C13 114.87(13) . . ?
O2 C11 C9 114.18(13) . . ?
N1 C11 C9 109.07(11) . . ?
C13 C11 C9 90.42(12) . . ?
C13 C12 C9 90.41(13) . . ?
C11 C13 C12 89.85(12) . . ?
C15 C14 C19 118.97(15) . . ?
C15 C14 N2 119.75(15) . . ?
C19 C14 N2 121.01(15) . . ?
C16 C15 C14 120.19(19) . . ?
C17 C16 C15 120.7(2) . . ?
C18 C17 C16 119.53(17) . . ?
C17 C18 C19 120.62(19) . . ?
C18 C19 C14 120.03(18) . . ?
C22 C21 C26 118.80(17) . . ?
C22 C21 C27 122.52(15) . . ?
C26 C21 C27 118.65(17) . . ?
C21 C22 C23 120.55(18) . . ?
C24 C23 C22 120.1(2) . . ?
C23 C24 C25 120.08(18) . . ?
C24 C25 C26 120.19(19) . . ?
C25 C26 C21 120.27(19) . . ?
O3 C27 C21 121.32(16) . . ?
O3 C27 C28 120.51(16) . . ?
C21 C27 C28 118.14(15) . . ?
C29 C28 C27 113.02(15) . . ?
C28 C29 C32 116.74(15) . . ?
C28 C29 C31 116.44(13) . . ?
C32 C29 C31 88.16(13) . . ?
C28 C29 S2 110.54(12) . . ?
C32 C29 S2 115.12(13) . . ?
C31 C29 S2 108.01(10) . . ?
N4 C30 N3 122.81(15) . . ?
N4 C30 S2 124.68(12) . . ?
N3 C30 S2 112.50(11) . . ?
O4 C31 N3 110.42(14) . . ?
O4 C31 C33 117.09(14) . . ?
N3 C31 C33 113.36(14) . . ?
O4 C31 C29 116.45(12) . . ?
N3 C31 C29 107.79(12) . . ?
C33 C31 C29 90.16(13) . . ?
C33 C32 C29 91.02(14) . . ?
C32 C33 C31 90.24(14) . . ?
C35 C34 C39 119.53(18) . . ?
C35 C34 N4 120.16(18) . . ?
C39 C34 N4 120.03(18) . . ?
C34 C35 C36 119.7(2) . . ?
C37 C36 C35 120.4(2) . . ?
C38 C37 C36 119.6(2) . . ?
C37 C38 C39 120.7(3) . . ?
C38 C39 C34 119.9(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
S1 C10 1.7619(16) . ?
S1 C9 1.8125(16) . ?
S2 C30 1.7551(16) . ?
S2 C29 1.8134(16) . ?
O1 C7 1.226(2) . ?
O2 C11 1.3873(19) . ?
O3 C27 1.214(2) . ?
O4 C31 1.3892(19) . ?
N1 C10 1.3523(18) . ?
N1 C20 1.450(2) . ?
N1 C11 1.4555(19) . ?
N2 C10 1.2912(18) . ?
N2 C14 1.4252(18) . ?
N3 C30 1.3502(19) . ?
N3 C31 1.4475(19) . ?
N3 C40 1.456(2) . ?
N4 C30 1.2859(19) . ?
N4 C34 1.419(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.405(2) . ?
C1 C7 1.484(2) . ?
C2 C3 1.385(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.374(3) . ?
C7 C8 1.515(2) . ?
C8 C9 1.507(2) . ?
C9 C12 1.556(2) . ?
C9 C11 1.562(2) . ?
C11 C13 1.542(2) . ?
C12 C13 1.548(3) . ?
C14 C15 1.388(2) . ?
C14 C19 1.389(2) . ?
C15 C16 1.381(3) . ?
C16 C17 1.377(3) . ?
C17 C18 1.370(3) . ?
C18 C19 1.389(2) . ?
C21 C22 1.388(3) . ?
C21 C26 1.395(2) . ?
C21 C27 1.494(2) . ?
C22 C23 1.389(3) . ?
C23 C24 1.373(3) . ?
C24 C25 1.381(3) . ?
C25 C26 1.385(3) . ?
C27 C28 1.515(2) . ?
C28 C29 1.513(2) . ?
C29 C32 1.548(3) . ?
C29 C31 1.561(2) . ?
C31 C33 1.531(2) . ?
C32 C33 1.521(3) . ?
C34 C35 1.373(3) . ?
C34 C39 1.381(3) . ?
C35 C36 1.392(3) . ?
C36 C37 1.370(4) . ?
C37 C38 1.361(4) . ?
C38 C39 1.381(3) . ?
