[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_7158806
_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 S'
_chemical_formula_sum            'C20 H12 O2 S'
_chemical_formula_weight         316.36
_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     iterative
_audit_creation_date             2017-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2021-10-02 deposited with the CCDC.	2022-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                99.420(7)
_cell_angle_beta                 93.883(6)
_cell_angle_gamma                108.503(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3023(5)
_cell_length_b                   9.0644(7)
_cell_length_c                   10.6356(10)
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5080
_cell_measurement_theta_min      4.0940
_cell_volume                     742.63(11)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_details
;
  1 omega  -25.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3317  -99.0000  120.0000 49

  2 omega  -25.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3317  -99.0000    0.0000 49

  3 omega  -49.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000   90.0000 84

  4 omega   -1.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   37.0000    0.0000 58

  5 omega  -48.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000 -150.0000 83

  6 omega  -49.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000  -30.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0036699000
_diffrn_orient_matrix_UB_12      0.0105659000
_diffrn_orient_matrix_UB_13      -0.0646220000
_diffrn_orient_matrix_UB_21      0.0330647000
_diffrn_orient_matrix_UB_22      0.0834596000
_diffrn_orient_matrix_UB_23      0.0215726000
_diffrn_orient_matrix_UB_31      0.0845401000
_diffrn_orient_matrix_UB_32      -0.0020234000
_diffrn_orient_matrix_UB_33      -0.0018859000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6559
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.264
_diffrn_reflns_theta_min         3.395
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95029
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0453P)^2^+0.0923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2603
_reflns_number_total             3428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01044e2.cif
_cod_data_source_block           20170331
_cod_database_code               7158806
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C19H12O4N2S1
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'