One-pot (2 + 4) cycloaddition of propargyl alcohols with <i>o</i>-hydroxyphenyl substituted secondary phosphine oxides.
Zhang, Sen; Zhang, Guo-Ke; Tian, Yi-Ming; Bai, Wen-Xin; Liu, Tian-Ya; Zhang, Yu-Chen; Organic & biomolecular chemistry 23 (2025) 9178–9184; doi:10.1039/d5ob01347j

data_7160754
_publ_section_title
;
 One-pot (2 + 4) cycloaddition of propargyl alcohols with
 <i>o</i>-hydroxyphenyl substituted secondary phosphine oxides.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9178
_journal_page_last               9184
_journal_paper_doi               10.1039/d5ob01347j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C33 H25 O2 P'
_chemical_formula_sum            'C33 H25 O2 P'
_chemical_formula_weight         484.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-08-08 deposited with the CCDC.	2025-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3252(2)
_cell_length_b                   14.4115(3)
_cell_length_c                   17.2540(3)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.944
_cell_measurement_theta_min      3.507
_cell_volume                     2514.86(8)
_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      170.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29733
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.940
_diffrn_reflns_theta_min         3.506
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.7864.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.9136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4103
_reflns_number_total             4771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01347j2.cif
_cod_data_source_block           240703sf_zgk
_cod_depositor_comments          'Adding full bibliography for 7160754.cif.'
_cod_database_code               7160754
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.880
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;
_shelx_res_checksum              63394
_olex2_submission_special_instructions 'No special instructions were received'