[4+2] Cycloaddition Reactions of β-Naphtha-1-thioquinones Generated from 2-Naphthols and DAST
Geng, Yang; Gao, Xianying; Liang, apeng; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01044E

data_7158807
_publ_section_title
;
 [4+2] Cycloaddition Reactions of \b-Naphtha-1-thioquinones Generated from
 2-Naphthols and DAST
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01044E
_journal_year                    2022
_chemical_formula_moiety         'C20 H12 O2 S2'
_chemical_formula_sum            'C20 H12 O2 S2'
_chemical_formula_weight         348.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-26
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-10-02 deposited with the CCDC.	2022-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.726(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1135(4)
_cell_length_b                   6.4959(3)
_cell_length_c                   26.5272(12)
_cell_measurement_reflns_used    2028
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2930
_cell_measurement_theta_min      5.0550
_cell_volume                     1568.64(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega -104.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000   30.0000 76

  2 omega  -24.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 61

  3 omega   18.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 46

  4 omega   18.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 41

  5 omega  -19.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   60.0000 30

  6 omega   35.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -116.0000  107.0000 43

  7 omega   58.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 52

  8 omega   71.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  150.0000 29

  9 omega   69.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 30

 10 omega   51.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 33

 11 omega   44.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 47

 12 omega  100.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 28

 13 omega   89.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 62

 14 omega   52.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 55

 15 omega   40.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 67

 16 omega   39.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 45

 17 omega   60.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 26

 18 omega   44.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 65

 19 omega  132.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 37

 20 omega   53.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 37

 21 omega  131.00  163.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0242708000
_diffrn_orient_matrix_UB_12      0.1135995000
_diffrn_orient_matrix_UB_13      0.0507154000
_diffrn_orient_matrix_UB_21      -0.0318265000
_diffrn_orient_matrix_UB_22      0.2066907000
_diffrn_orient_matrix_UB_23      -0.0267231000
_diffrn_orient_matrix_UB_31      -0.1644906000
_diffrn_orient_matrix_UB_32      -0.0233615000
_diffrn_orient_matrix_UB_33      0.0098093000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5782
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         5.062
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0520
_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/[\s^2^(Fo^2^)+(0.0611P)^2^+1.0766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2327
_reflns_number_total             2786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01044e2.cif
_cod_data_source_block           201709177
_cod_original_cell_volume        1568.65(13)
_cod_database_code               7158807
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H41N2O2S2
_shelx_estimated_absorpt_t_max   0.685
_shelx_estimated_absorpt_t_min   0.601
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(S1A)
Uanis(S2) = Uanis(S2A)
Uanis(O2) = Uanis(O2A)
Uanis(O1) = Uanis(O1A)
3. Others
 Sof(O1A)=Sof(O2A)=Sof(S1A)=Sof(S2A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(S1)=Sof(S2)=FVAR(1)
;
_olex2_submission_special_instructions 'No special instructions were received'