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#$Date: 2024-12-06 22:36:35 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296682 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160136.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_7160136
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         ' 	C19 H18 N2 O2 S, C H Cl3 '
_chemical_formula_sum            'C20 H19 Cl3 N2 O2 S'
_chemical_formula_weight         457.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 108.215(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0280(14)
_cell_length_b                   18.344(2)
_cell_length_c                   11.1908(13)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.24
_cell_volume                     2150.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0928
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            86872
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.060
_diffrn_reflns_theta_min         2.214
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_correction_T_min  0.8173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX4'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         6870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0562
_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)+(0.0657P)²+1.1406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1618
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4277
_reflns_number_total             6870
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01103a2.cif
_cod_data_source_block           5n
_cod_depositor_comments
'Adding full bibliography for 7160135--7160138.cif.'
_cod_original_cell_volume        2150.4(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160136
_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   0.939
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C21A C 0.9550(15) 0.2188(9) 0.9651(17) 0.057(3) Uani 0.675(3) 1 d . . P A 1
H21A H 0.998198 0.253656 1.033908 0.068 Uiso 0.675(3) 1 calc R U P A 1
Cl1A Cl 0.9142(2) 0.1470(2) 1.0348(3) 0.179(2) Uani 0.675(3) 1 d . . P A 1
Cl2A Cl 1.05573(12) 0.20525(8) 0.88364(13) 0.0743(5) Uani 0.675(3) 1 d . . P A 1
Cl3A Cl 0.80754(18) 0.26748(10) 0.86169(15) 0.0549(4) Uani 0.675(3) 1 d . . P A
1
C21B C 0.937(4) 0.233(2) 0.964(4) 0.052(5) Uani 0.325(3) 1 d . . P A 2
H21B H 1.013374 0.265682 0.985913 0.063 Uiso 0.325(3) 1 calc R U P A 2
Cl1B Cl 0.8985(3) 0.2024(3) 1.0946(3) 0.0883(11) Uani 0.325(3) 1 d . . P A 2
Cl2B Cl 0.9655(7) 0.1372(4) 0.9005(6) 0.222(5) Uani 0.325(3) 1 d . . P A 2
Cl3B Cl 0.8323(7) 0.2618(5) 0.8756(9) 0.188(4) Uani 0.325(3) 1 d . . P A 2
S1 S 0.20636(5) 0.18399(3) 0.68032(5) 0.03615(15) Uani 1 1 d . . . . .
O1 O 0.59759(15) 0.34519(8) 0.67331(13) 0.0387(3) Uani 1 1 d . . . . .
O2 O 0.35178(15) 0.17716(7) 0.31090(12) 0.0336(3) Uani 1 1 d . . . . .
H200 H 0.299705 0.211939 0.297727 0.050 Uiso 1 1 calc R U . . .
N1 N 0.30933(16) 0.14498(8) 0.49977(14) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.39885(17) 0.24099(9) 0.60990(15) 0.0316(4) Uani 1 1 d . . . . .
H2 H 0.410134 0.277513 0.663259 0.038 Uiso 1 1 calc R U . . .
C2 C 0.61750(19) 0.42237(10) 0.51097(18) 0.0296(4) Uani 1 1 d . . . . .
C3 C 0.6960(2) 0.47102(11) 0.5963(2) 0.0373(5) Uani 1 1 d . . . . .
H3 H 0.719520 0.461162 0.683918 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7399(2) 0.53357(12) 0.5543(2) 0.0457(6) Uani 1 1 d . . . . .
H4 H 0.793252 0.566510 0.613117 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7061(2) 0.54817(13) 0.4270(2) 0.0478(6) Uani 1 1 d . . . . .
H5 H 0.737421 0.590719 0.398142 0.057 Uiso 1 1 calc R U . . .
C6 C 0.6270(3) 0.50093(14) 0.3421(2) 0.0501(6) Uani 1 1 d . . . . .
H6 H 0.602878 0.511364 0.254627 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5826(2) 0.43834(12) 0.3835(2) 0.0404(5) Uani 1 1 d . . . . .
H7 H 0.527901 0.406107 0.324321 0.048 Uiso 1 1 calc R U . . .
C8 C 0.57557(18) 0.35488(10) 0.56087(18) 0.0285(4) Uani 1 1 d . . . . .
C9 C 0.5032(2) 0.29787(10) 0.46664(18) 0.0298(4) Uani 1 1 d . . . . .
H9A H 0.420901 0.318879 0.414672 0.036 Uiso 1 1 calc R U . . .
H9B H 0.553280 0.285466 0.409870 0.036 Uiso 1 1 calc R U . . .
C10 C 0.47726(19) 0.22880(10) 0.52876(17) 0.0272(4) Uani 1 1 d . . . . .
C11 C 0.40513(19) 0.16649(10) 0.43974(17) 0.0284(4) Uani 1 1 d . . . . .
C12 C 0.30753(18) 0.19048(10) 0.59446(17) 0.0269(4) Uani 1 1 d . . . . .
C13 C 0.5916(2) 0.17526(11) 0.5804(2) 0.0355(4) Uani 1 1 d . . . . .
H13A H 0.673483 0.194376 0.574529 0.043 Uiso 1 1 calc R U . . .
H13B H 0.601462 0.157215 0.666279 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5260(2) 0.11993(11) 0.4753(2) 0.0379(5) Uani 1 1 d . . . . .
H14A H 0.566583 0.116554 0.408159 0.046 Uiso 1 1 calc R U . . .
H14B H 0.514467 0.070949 0.507347 0.046 Uiso 1 1 calc R U . . .
C15 C 0.23154(19) 0.08131(11) 0.46324(19) 0.0318(4) Uani 1 1 d . . . . .
C16 C 0.2533(2) 0.02196(11) 0.5436(2) 0.0422(5) Uani 1 1 d . . . . .
H16 H 0.318920 0.023708 0.622379 0.051 Uiso 1 1 calc R U . . .
C17 C 0.1790(3) -0.03983(14) 0.5086(3) 0.0602(7) Uani 1 1 d . . . . .
H17 H 0.192841 -0.080371 0.564085 0.072 Uiso 1 1 calc R U . . .
C18 C 0.0857(3) -0.04299(17) 0.3948(3) 0.0730(9) Uani 1 1 d . . . . .
H18 H 0.035258 -0.085757 0.371239 0.088 Uiso 1 1 calc R U . . .
C19 C 0.0646(3) 0.0157(2) 0.3142(3) 0.0783(10) Uani 1 1 d . . . . .
H19 H 0.000291 0.013095 0.234663 0.094 Uiso 1 1 calc R U . . .
C20 C 0.1371(2) 0.07906(16) 0.3487(2) 0.0545(7) Uani 1 1 d . . . . .
H20 H 0.121598 0.120008 0.294026 0.065 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'
Cl Cl 0.1484 0.1585 '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
Cl2A C21A Cl1A 117.7(9) . . ?
Cl2A C21A Cl3A 109.2(10) . . ?
Cl1A C21A Cl3A 110.7(9) . . ?
Cl3B C21B Cl1B 111(2) . . ?
Cl3B C21B Cl2B 106(2) . . ?
Cl1B C21B Cl2B 97(2) . . ?
C12 N1 C15 124.93(16) . . ?
C12 N1 C11 112.33(15) . . ?
C15 N1 C11 122.70(15) . . ?
C12 N2 C10 112.52(15) . . ?
C7 C2 C3 118.86(18) . . ?
C7 C2 C8 122.81(18) . . ?
C3 C2 C8 118.33(18) . . ?
C4 C3 C2 120.5(2) . . ?
C5 C4 C3 120.1(2) . . ?
C6 C5 C4 119.9(2) . . ?
C5 C6 C7 120.3(2) . . ?
C6 C7 C2 120.4(2) . . ?
O1 C8 C2 121.57(17) . . ?
O1 C8 C9 120.50(17) . . ?
C2 C8 C9 117.93(16) . . ?
C10 C9 C8 112.96(15) . . ?
N2 C10 C9 113.10(15) . . ?
N2 C10 C13 115.81(16) . . ?
C9 C10 C13 116.75(17) . . ?
N2 C10 C11 103.14(15) . . ?
C9 C10 C11 116.82(15) . . ?
C13 C10 C11 88.11(14) . . ?
O2 C11 N1 112.30(16) . . ?
O2 C11 C14 113.65(16) . . ?
N1 C11 C14 115.04(16) . . ?
O2 C11 C10 121.66(15) . . ?
N1 C11 C10 101.56(14) . . ?
C14 C11 C10 90.80(15) . . ?
N2 C12 N1 109.46(16) . . ?
N2 C12 S1 125.39(14) . . ?
N1 C12 S1 125.14(15) . . ?
C14 C13 C10 89.99(15) . . ?
C11 C14 C13 89.66(15) . . ?
C20 C15 C16 120.6(2) . . ?
C20 C15 N1 120.13(19) . . ?
C16 C15 N1 119.30(19) . . ?
C17 C16 C15 119.6(2) . . ?
C18 C17 C16 120.4(3) . . ?
C17 C18 C19 120.1(3) . . ?
C18 C19 C20 120.3(3) . . ?
C15 C20 C19 119.0(3) . . ?
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
C21A Cl2A 1.661(15) . ?
C21A Cl1A 1.66(2) . ?
C21A Cl3A 1.899(15) . ?
C21B Cl3B 1.37(3) . ?
C21B Cl1B 1.73(4) . ?
C21B Cl2B 1.96(3) . ?
S1 C12 1.6890(19) . ?
O1 C8 1.218(2) . ?
O2 C11 1.390(2) . ?
N1 C12 1.354(2) . ?
N1 C15 1.431(2) . ?
N1 C11 1.472(2) . ?
N2 C12 1.339(2) . ?
N2 C10 1.454(2) . ?
C2 C7 1.388(3) . ?
C2 C3 1.393(3) . ?
C2 C8 1.490(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.377(4) . ?
C6 C7 1.384(3) . ?
C8 C9 1.522(3) . ?
C9 C10 1.515(3) . ?
C10 C13 1.560(3) . ?
C10 C11 1.561(3) . ?
C11 C14 1.527(3) . ?
C13 C14 1.550(3) . ?
C15 C20 1.376(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.365(5) . ?
C18 C19 1.378(5) . ?
C19 C20 1.395(4) . ?
