Meyer-Schuster rearrangement/allylic alkenylation of propynolaldehydes with olefins to synthesize skipped 1,4-dienes.
Shen, Cheng-Ping; Zhu, Hai-Tao; Li, Guo-Hua; Chang, Xin; Xi, Jia-Jun; Zhou, Ni-Ni; Zhou, An-Xi; Organic & biomolecular chemistry 23 (2025) 3870–3874; doi:10.1039/d5ob00173k

data_7160410
_publ_section_title
;
 Meyer-Schuster rearrangement/allylic alkenylation of propynolaldehydes
 with olefins to synthesize skipped 1,4-dienes.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3870
_journal_page_last               3874
_journal_paper_doi               10.1039/d5ob00173k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C36 H26 O'
_chemical_formula_sum            'C36 H26 O'
_chemical_formula_weight         474.57
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-01-25 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.362(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2849(7)
_cell_length_b                   21.4705(17)
_cell_length_c                   12.8615(9)
_cell_measurement_reflns_used    8206
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.39
_cell_volume                     2561.8(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            55086
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.392
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.4094.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0612
_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^)+(0.0800P)^2^+1.2248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4233
_reflns_number_total             5242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00173k2.cif
_cod_data_source_block           mo_1123_2_0m
_cod_depositor_comments
'Adding full bibliography for 7160406--7160410.cif.'
_cod_database_code               7160410
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C32(H32), C26(H26), C5(H5), C19(H19), C13(H13), C9(H9), C22(H22),
 C28(H28), C27(H27), C34(H34), C33(H33), C36(H36), C30(H30), C29(H29), C12(H12),
  C20(H20), C10(H10), C35(H35), C1(H1), C21(H21), C4(H4), C2(H2), C11(H11),
 C3(H3)
;
_shelx_res_checksum              16741
_olex2_submission_special_instructions 'No special instructions were received'