Calcium-catalyzed dehydrative allylation of P-ylides and sequential Wittig reaction for streamlined access to versatile 1,4-dienes
Li, Xiaohong; Zhang, Dong; Wang, Yan; Xiao, Shiji; Wu, Ying; Xie, Peizhong; Loh, Teck-Peng; New Journal of Chemistry 47 (2023) 18779–18784; doi:10.1039/D3NJ03640E

data_7062732
_publ_section_title
;
 Calcium-catalyzed dehydrative allylation of P-ylides and sequential
 Wittig reaction for streamlined access to versatile 1,4-dienes
;
_journal_issue                   40
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18779
_journal_page_last               18784
_journal_paper_doi               10.1039/D3NJ03640E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         '2(C14 H17 O4)'
_chemical_formula_sum            'C28 H34 O8'
_chemical_formula_weight         498.55
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-11 deposited with the CCDC.	2023-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                79.753(2)
_cell_angle_beta                 81.874(2)
_cell_angle_gamma                81.718(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4044(3)
_cell_length_b                   14.2246(7)
_cell_length_c                   17.7580(8)
_cell_measurement_reflns_used    9773
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.164
_cell_measurement_theta_min      3.181
_cell_volume                     1319.95(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39888
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.297
_diffrn_reflns_theta_min         2.546
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1382 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.7735.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0575P)^2^+0.2869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4423
_reflns_number_total             4815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03640e2.cif
_cod_data_source_block           cu_230319lu_ngd_0m
_cod_depositor_comments          'Adding full bibliography for 7062732.cif.'
_cod_database_code               7062732
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.908
_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:
 C16(H16A,H16B), C19(H19A,H19B), C27(H27A,H27B), C2(H2A,H2B), C9(H9A,H9B),
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C24(H24), C25(H25), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C28(H28A,H28B,H28C), C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              85491
_olex2_submission_special_instructions 'No special instructions were received'