Synthesis of γ-Pyrones from Formal [4 + 2] Cyclization of Ketene Dithioacetals with Acyl Chlorides.
Wang, Mingshan; Shi, Lou; Li, Yifei; Liu, Qun; Pan, Ling; The Journal of organic chemistry 84 (2019) 9603–9610; doi:10.1021/acs.joc.9b01254

data_4034406
_publ_section_title
;
 Synthesis of \g-Pyrones from Formal [4 + 2] Cyclization of Ketene
 Dithioacetals with Acyl Chlorides.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9603
_journal_page_last               9610
_journal_paper_doi               10.1021/acs.joc.9b01254
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H18 O4 S'
_chemical_formula_sum            'C18 H18 O4 S'
_chemical_formula_weight         330.38
_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
_audit_creation_date             2019-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                92.768(2)
_cell_angle_beta                 99.629(3)
_cell_angle_gamma                113.402(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2849(11)
_cell_length_b                   8.8114(13)
_cell_length_c                   13.947(2)
_cell_measurement_reflns_used    1567
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.155
_cell_measurement_theta_min      2.539
_cell_volume                     803.5(2)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  BrukerAXS
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4543
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.778
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.669532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0300 before and 0.0146 after correction.
The Ratio of minimum to maximum transmission is 0.6695.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.669532
_exptl_transmission_factor_min   0.0604
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0702P)^2^+0.3123P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2520
_reflns_number_total             3172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01254_si_002.cif
_cod_data_source_block           a
_cod_database_code               4034406
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.978
_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.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c)
;
_olex2_submission_special_instructions 'No special instructions were received'