Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium Salts: The Synthesis of Spirocyclopropanyl para-Dienones.
Zhang, Xiang-Zhi; Du, Ji-Yuan; Deng, Yu-Hua; Chu, Wen-Dao; Yan, Xu; Yu, Ke-Yin; Fan, Chun-An; The Journal of organic chemistry 81 (2016) 2598–2606; doi:10.1021/acs.joc.5b02725

data_4036558
_publ_section_title
;
 Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium
 Salts: The Synthesis of Spirocyclopropanyl para-Dienones.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2598
_journal_page_last               2606
_journal_paper_doi               10.1021/acs.joc.5b02725
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H18 O3'
_chemical_formula_sum            'C21 H18 O3'
_chemical_formula_weight         318.35
_space_group_crystal_system      triclinic
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Olex2 1.2
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_cell_length_a                   9.0267(9)
_cell_length_b                   11.7280(13)
_cell_length_c                   17.0697(19)
_cell_measurement_reflns_used    5005
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4820
_cell_measurement_theta_min      3.9980
_cell_volume                     1691.3(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
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_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_13      0.0703587000
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_diffrn_orient_matrix_UB_31      0.1511249000
_diffrn_orient_matrix_UB_32      0.0764695000
_diffrn_orient_matrix_UB_33      -0.0348191000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0415
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_diffrn_reflns_theta_max         70.041
_diffrn_reflns_theta_min         4.021
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.665
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.250
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_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0089(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_number_reflns         6267
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_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
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 w=1/[\s^2^(Fo^2^)+(0.0989P)^2^+0.3498P]
 where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
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_olex2_refinement_description
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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 Ternary CH refined with riding coordinates:
 C32(H32), C11(H11), C40(H40), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C22(H22), C3(H3), C27(H27), C6(H6), C9(H9), C38(H38), C17(H17),
 C28(H28), C8(H8), C24(H24), C30(H30), C7(H7), C14(H14), C16(H16), C13(H13),
 C35(H35), C36(H36), C15(H15), C34(H34), C29(H29), C37(H37)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              85554
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