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#$Date: 2024-09-06 02:15:39 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294431 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/33/7133384.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_7133384
loop_
_publ_author_name
'Li, Xuejian'
'Liu, Qinglong'
'Song, Wangze'
_publ_section_title
;
 Chemical fixation of CO₂/CS₂ to access iodoallenyl
 oxazolidinones and allenyl thiazolidine-thiones.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8756
_journal_page_last               8759
_journal_paper_doi               10.1039/d4cc02894e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C16 H17 N O2 S2'
_chemical_formula_sum            'C16 H17 N O2 S2'
_chemical_formula_weight         319.42
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-17 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.291(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.822(3)
_cell_length_b                   9.4151(14)
_cell_length_c                   9.3683(14)
_cell_measurement_reflns_used    5464
_cell_measurement_temperature    273.00
_cell_measurement_theta_max      25.494
_cell_measurement_theta_min      2.170
_cell_volume                     1655.5(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.00
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11489
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.650
_diffrn_reflns_theta_min         2.170
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1013 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.9364.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0678P)²+0.7465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2473
_reflns_number_total             3101
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02894e2.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 7133384.cif.'
_cod_database_code               7133384
_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_max   0.984
_shelx_estimated_absorpt_t_min   0.938
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O00C \\sim C00I \\sim O00J \\sim C1 \\sim C2 \\sim O00D \\sim C00J \\sim C2A
\\sim C1A \\sim O00K: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
3. Rigid body (RIGU) restrains
 O00C, C2, C1, C00I, O00J, C00G
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O00D, O00K, C1A, C00J, C2A, C00G
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(O00D)=Sof(C00J)=Sof(H00M)=Sof(H00N)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(H2AC)=Sof(C1A)=Sof(O00K)=1-FVAR(1)
 Sof(O00C)=Sof(C00I)=Sof(H00K)=Sof(H00L)=Sof(O00J)=Sof(C1)=Sof(C2)=Sof(H2A)=
 Sof(H2B)=Sof(H2C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C007(H007)
5.b Secondary CH2 refined with riding coordinates:
 C006(H00B,H00A), C009(H00C,H00D), C00I(H00K,H00L), C00J(H00M,H00N)
5.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00E), C00D(H00F), C00E(H00G), C00F(H00H), C00H(H00J)
5.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S001 S 0.93587(3) 0.68770(6) 0.54522(6) 0.0443(2) Uani 1 1 d . . . . .
S002 S 0.95687(4) 0.51576(8) 0.80990(7) 0.0539(2) Uani 1 1 d . . . . .
N003 N 0.89020(10) 0.43331(19) 0.5592(2) 0.0404(4) Uani 1 1 d . . . . .
C004 C 0.92438(11) 0.5309(2) 0.6400(2) 0.0370(5) Uani 1 1 d . . . . .
C005 C 0.81157(13) 0.2287(2) 0.6046(3) 0.0451(6) Uani 1 1 d . . . . .
C006 C 0.87356(14) 0.4679(2) 0.4090(2) 0.0450(6) Uani 1 1 d . . . . .
H00B H 0.825713 0.436274 0.378921 0.054 Uiso 1 1 calc R U . . .
H00A H 0.906600 0.419868 0.350632 0.054 Uiso 1 1 calc R U . . .
C007 C 0.87916(13) 0.6277(2) 0.3893(2) 0.0438(6) Uani 1 1 d . . . . .
H007 H 0.903760 0.646598 0.302709 0.053 Uiso 1 1 calc R U . . .
C008 C 0.81080(16) 0.7088(3) 0.3806(3) 0.0609(7) Uani 1 1 d . . . . .
H008 H 0.812629 0.802600 0.350052 0.073 Uiso 1 1 calc R U . . .
C009 C 0.88654(14) 0.2836(3) 0.6008(3) 0.0541(7) Uani 1 1 d . . . . .
H00C H 0.911124 0.271731 0.694807 0.065 Uiso 1 1 calc R U . . .
H00D H 0.911322 0.226820 0.533819 0.065 Uiso 1 1 calc R U . . .
C00A C 0.74974(17) 0.6618(3) 0.4112(3) 0.0636(8) Uani 1 1 d . . . . .
C00B C 0.79491(18) 0.0969(3) 0.5488(3) 0.0670(8) Uani 1 1 d . . . . .
H00E H 0.829147 0.045111 0.504563 0.080 Uiso 1 1 calc R U . . .
O00C O 0.6060(8) 0.7314(18) 0.596(2) 0.101(2) Uani 0.491(12) 1 d . U P A 1
C00D C 0.76148(18) 0.3022(3) 0.6710(4) 0.0760(9) Uani 1 1 d . . . . .
H00F H 0.772644 0.390740 0.710562 0.091 Uiso 1 1 calc R U . . .
C00E C 0.6941(2) 0.2466(5) 0.6804(6) 0.1092(15) Uani 1 1 d . . . . .
H00G H 0.660096 0.297502 0.726166 0.131 Uiso 1 1 calc R U . . .
C00F C 0.6777(2) 0.1166(5) 0.6221(6) 0.1052(15) Uani 1 1 d . . . . .
H00H H 0.632039 0.079742 0.626307 0.126 Uiso 1 1 calc R U . . .
C00G C 0.6873(2) 0.6175(4) 0.4420(5) 0.0872(10) Uani 1 1 d . . . . .
C00H C 0.7280(2) 0.0413(4) 0.5579(4) 0.0924(12) Uani 1 1 d . . . . .
H00J H 0.717091 -0.048135 0.520186 0.111 Uiso 1 1 calc R U . . .
C00I C 0.6674(10) 0.6428(19) 0.596(2) 0.097(3) Uani 0.491(12) 1 d . U P A 1
H00K H 0.657850 0.552458 0.640144 0.116 Uiso 0.491(12) 1 calc R U P A 1
H00L H 0.706989 0.687419 0.650578 0.116 Uiso 0.491(12) 1 calc R U P A 1
O00J O 0.4878(7) 0.8249(16) 0.609(2) 0.199(4) Uani 0.491(12) 1 d . U P A 1
C1 C 0.5437(9) 0.6884(18) 0.608(2) 0.120(2) Uani 0.491(12) 1 d . U P A 1
C2 C 0.5346(6) 0.5502(13) 0.616(2) 0.134(4) Uani 0.491(12) 1 d . U P A 1
H2A H 0.548048 0.506354 0.529688 0.202 Uiso 0.491(12) 1 calc R U P A 1
H2B H 0.485419 0.530015 0.628402 0.202 Uiso 0.491(12) 1 calc R U P A 1
H2C H 0.563662 0.513355 0.696273 0.202 Uiso 0.491(12) 1 calc R U P A 1
O00D O 0.5951(8) 0.7043(16) 0.568(2) 0.112(2) Uani 0.509(12) 1 d . U P A 2
C00J C 0.6569(10) 0.6075(19) 0.576(2) 0.104(3) Uani 0.509(12) 1 d . U P A 2
H00M H 0.691341 0.635459 0.652903 0.125 Uiso 0.509(12) 1 calc R U P A 2
H00N H 0.641863 0.510836 0.592815 0.125 Uiso 0.509(12) 1 calc R U P A 2
C2A C 0.5536(6) 0.5872(13) 0.7366(17) 0.125(4) Uani 0.509(12) 1 d . U P A 2
H2AA H 0.548463 0.491870 0.700996 0.188 Uiso 0.509(12) 1 calc R U P A 2
H2AB H 0.518981 0.604504 0.804730 0.188 Uiso 0.509(12) 1 calc R U P A 2
H2AC H 0.600624 0.599602 0.782040 0.188 Uiso 0.509(12) 1 calc R U P A 2
C1A C 0.5455(9) 0.661(2) 0.648(2) 0.124(2) Uani 0.509(12) 1 d . U P A 2
O00K O 0.4826(6) 0.7479(15) 0.6291(18) 0.184(4) Uani 0.509(12) 1 d . U P A 2
H00I H 0.644(2) 0.565(5) 0.404(5) 0.135(16) 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'
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
C004 S001 C007 93.32(11) . . ?
C004 N003 C006 117.18(18) . . ?
C004 N003 C009 123.1(2) . . ?
C006 N003 C009 117.47(19) . . ?
S002 C004 S001 120.51(13) . . ?
N003 C004 S001 111.69(17) . . ?
N003 C004 S002 127.78(17) . . ?
C00B C005 C009 119.2(2) . . ?
C00D C005 C009 121.4(2) . . ?
C00D C005 C00B 119.2(3) . . ?
N003 C006 H00B 109.9 . . ?
N003 C006 H00A 109.9 . . ?
N003 C006 C007 109.06(18) . . ?
H00B C006 H00A 108.3 . . ?
C007 C006 H00B 109.9 . . ?
C007 C006 H00A 109.9 . . ?
S001 C007 H007 108.7 . . ?
C006 C007 S001 104.47(15) . . ?
C006 C007 H007 108.7 . . ?
C008 C007 S001 109.53(17) . . ?
C008 C007 C006 116.4(2) . . ?
C008 C007 H007 108.7 . . ?
C007 C008 H008 116.8 . . ?
C00A C008 C007 126.4(3) . . ?
C00A C008 H008 116.8 . . ?
N003 C009 C005 113.5(2) . . ?
N003 C009 H00C 108.9 . . ?
N003 C009 H00D 108.9 . . ?
C005 C009 H00C 108.9 . . ?
C005 C009 H00D 108.9 . . ?
H00C C009 H00D 107.7 . . ?
C008 C00A C00G 178.5(3) . . ?
C005 C00B H00E 119.8 . . ?
C00H C00B C005 120.4(3) . . ?
C00H C00B H00E 119.8 . . ?
C1 O00C C00I 125.2(13) . . ?
C005 C00D H00F 119.7 . . ?
C005 C00D C00E 120.6(3) . . ?
C00E C00D H00F 119.7 . . ?
C00D C00E H00G 120.1 . . ?
C00F C00E C00D 119.7(4) . . ?
C00F C00E H00G 120.1 . . ?
C00E C00F H00H 120.0 . . ?
C00H C00F C00E 120.0(3) . . ?
C00H C00F H00H 120.0 . . ?
C00A C00G C00I 116.6(8) . . ?
C00A C00G C00J 130.4(9) . . ?
C00A C00G H00I 144(3) . . ?
C00I C00G H00I 99(3) . . ?
C00J C00G H00I 85(3) . . ?
C00B C00H H00J 120.0 . . ?
C00F C00H C00B 120.1(3) . . ?
C00F C00H H00J 120.0 . . ?
O00C C00I C00G 110.6(13) . . ?
O00C C00I H00K 109.5 . . ?
O00C C00I H00L 109.5 . . ?
C00G C00I H00K 109.5 . . ?
C00G C00I H00L 109.5 . . ?
H00K C00I H00L 108.1 . . ?
O00C C1 O00J 110.4(12) . . ?
O00C C1 C2 116.8(14) . . ?
C2 C1 O00J 132.8(13) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1A O00D C00J 112.1(14) . . ?
C00G C00J O00D 106.6(13) . . ?
C00G C00J H00M 110.4 . . ?
C00G C00J H00N 110.4 . . ?
O00D C00J H00M 110.4 . . ?
O00D C00J H00N 110.4 . . ?
H00M C00J H00N 108.6 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C1A C2A H2AA 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
C1A C2A H2AC 109.5 . . ?
O00D C1A O00K 111.7(14) . . ?
C2A C1A O00D 124.9(18) . . ?
C2A C1A O00K 122.0(14) . . ?
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
S001 C004 1.744(2) . ?
S001 C007 1.832(2) . ?
S002 C004 1.668(2) . ?
N003 C004 1.326(3) . ?
N003 C006 1.456(3) . ?
N003 C009 1.466(3) . ?
C005 C009 1.506(4) . ?
C005 C00B 1.374(4) . ?
C005 C00D 1.357(4) . ?
C006 H00B 0.9700 . ?
C006 H00A 0.9700 . ?
C006 C007 1.521(3) . ?
C007 H007 0.9800 . ?
C007 C008 1.493(4) . ?
C008 H008 0.9300 . ?
C008 C00A 1.284(4) . ?
C009 H00C 0.9700 . ?
C009 H00D 0.9700 . ?
C00A C00G 1.300(5) . ?
C00B H00E 0.9300 . ?
C00B C00H 1.372(5) . ?
O00C C00I 1.426(19) . ?
O00C C1 1.25(2) . ?
C00D H00F 0.9300 . ?
C00D C00E 1.380(5) . ?
C00E H00G 0.9300 . ?
C00E C00F 1.366(6) . ?
C00F H00H 0.9300 . ?
C00F C00H 1.359(6) . ?
C00G C00I 1.53(2) . ?
C00G C00J 1.42(2) . ?
C00G H00I 1.00(5) . ?
C00H H00J 0.9300 . ?
C00I H00K 0.9700 . ?
C00I H00L 0.9700 . ?
O00J C1 1.661(18) . ?
C1 C2 1.32(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
O00D C00J 1.476(18) . ?
O00D C1A 1.30(2) . ?
C00J H00M 0.9700 . ?
C00J H00N 0.9700 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C2A C1A 1.083(15) . ?
C1A O00K 1.438(17) . ?
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
S001 C007 C008 C00A -105.9(3) . . . . ?
N003 C006 C007 S001 21.1(2) . . . . ?
N003 C006 C007 C008 -99.8(2) . . . . ?
C004 S001 C007 C006 -16.69(17) . . . . ?
C004 S001 C007 C008 108.70(18) . . . . ?
C004 N003 C006 C007 -17.7(3) . . . . ?
C004 N003 C009 C005 123.3(2) . . . . ?
C005 C00B C00H C00F 0.2(6) . . . . ?
C005 C00D C00E C00F -0.1(6) . . . . ?
C006 N003 C004 S001 4.4(3) . . . . ?
C006 N003 C004 S002 -173.79(16) . . . . ?
C006 N003 C009 C005 -74.4(3) . . . . ?
C006 C007 C008 C00A 12.3(4) . . . . ?
C007 S001 C004 S002 -173.65(14) . . . . ?
C007 S001 C004 N003 8.04(18) . . . . ?
C009 N003 C004 S001 166.68(18) . . . . ?
C009 N003 C004 S002 -11.5(3) . . . . ?
C009 N003 C006 C007 179.0(2) . . . . ?
C009 C005 C00B C00H 176.4(3) . . . . ?
C009 C005 C00D C00E -176.4(3) . . . . ?
C00A C00G C00I O00C 118.8(9) . . . . ?
C00A C00G C00J O00D 116.8(10) . . . . ?
C00B C005 C009 N003 137.2(3) . . . . ?
C00B C005 C00D C00E -1.1(5) . . . . ?
C00D C005 C009 N003 -47.6(4) . . . . ?
C00D C005 C00B C00H 1.1(5) . . . . ?
C00D C00E C00F C00H 1.4(7) . . . . ?
C00E C00F C00H C00B -1.4(6) . . . . ?
C00I O00C C1 O00J 178.3(14) . . . . ?
C00I O00C C1 C2 -2(3) . . . . ?
C1 O00C C00I C00G 99(2) . . . . ?
C00J O00D C1A C2A 20(3) . . . . ?
C00J O00D C1A O00K -174.0(15) . . . . ?
C1A O00D C00J C00G 151(2) . . . . ?
