Phosphine-catalyzed (3+3) annulation of cinnamaldehyde-derived Morita-Baylis-Hillman carbonates with dinucleophiles.
Ren, Yue; Shi, Wangyu; Tang, Yi; Guo, Hongchao; Chemical communications (Cambridge, England) 60 (2024) 6897–6900; doi:10.1039/d4cc01989j

data_7133177
_publ_section_title
;
 Phosphine-catalyzed (3+3) annulation of cinnamaldehyde-derived
 Morita-Baylis-Hillman carbonates with dinucleophiles.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6897
_journal_page_last               6900
_journal_paper_doi               10.1039/d4cc01989j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C29 H28 O4'
_chemical_formula_sum            'C29 H28 N0 O4'
_chemical_formula_weight         440.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-12-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-07-18 deposited with the CCDC.	2024-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.935(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9766(15)
_cell_length_b                   15.8235(11)
_cell_length_c                   15.6346(12)
_cell_measurement_reflns_used    7464
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      3.03
_cell_volume                     4930.4(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.11
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0462
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31095
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.887
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0767 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.9126.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5661
_refine_ls_number_restraints     264
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0734P)^2^+2.3527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3986
_reflns_number_total             5661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01989j2.cif
_cod_data_source_block           20201223_3_41_8_0m_a
_cod_depositor_comments          'Adding full bibliography for 7133177.cif.'
_cod_database_code               7133177
_shelx_shelxl_version_number     2014/7
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C6(H6), C10(H10), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29)
3.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              62957
_shelx_hkl_checksum              81417
_olex2_submission_special_instructions 'No special instructions were received'