Phosphine-catalyzed sequential [4+ ]/[2+3] annulation of o-amino arylaldimines with Morita–Baylis–Hillman (MBH) carbonates
Hu, Xianfei; Qu, Xiaoxiao; Li, Zhiyue; Wang, Lishuang; Yao, Hui; Li, Linxuan; Cao, ZhongYan; Huang, Nianyu; Wang, Nengzhong; Chemical Communications  (2026) –; doi:10.1039/D6CC00562D

data_7135684
_publ_section_title
;
 Phosphine-catalyzed sequential [4+1]/[2+3] annulation of <i>o</i>-amino
 arylaldimines with Morita-Baylis-Hillman (MBH) carbonates.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8013
_journal_page_last               8017
_journal_paper_doi               10.1039/d6cc00562d
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H26 N2 O6 S2'
_chemical_formula_sum            'C26 H26 N2 O6 S2'
_chemical_formula_weight         526.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-17
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-12-18 deposited with the CCDC.	2026-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2302(3)
_cell_length_b                   25.9843(8)
_cell_length_c                   10.4917(3)
_cell_measurement_reflns_used    8548
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.1720
_cell_measurement_theta_min      3.3410
_cell_volume                     2516.33(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -117.00  -8.00   1.00    1.37    --  -40.73 -77.00 -30.00  109
  2  \w      1.00  82.00   1.00    1.37    --   40.73 -99.00   0.00   81
  3  \w     16.00 115.00   1.00    1.37    --   40.73  38.00-120.00   99
  4  \w     79.00 178.00   1.00    5.46    --  106.95  30.00  60.00   99
  5  \w     54.00 178.00   1.00    5.46    --  106.95  15.00 150.00  124
  6  \w     34.00 121.00   1.00    5.46    --  106.95-125.00-120.00   87
  7  \w     94.00 178.00   1.00    5.46    --  106.95 125.00-180.00   84
  8  \w     35.00 136.00   1.00    5.46    --  106.95 -61.00  60.00  101
  9  \w   -117.00  -8.00   1.00    1.37    --  -40.73 -77.00  90.00  109
 10  \w     69.00 118.00   1.00    1.37    --   40.73 163.00 -55.00   49
 11  \w     54.00 178.00   1.00    5.46    --  106.95  15.00 -30.00  124
 12  \w     81.00 178.00   1.00    5.46    --  106.95  45.00-150.00   97
 13  \w     74.00 104.00   1.00    5.46    --  106.95  77.00   0.00   30
 14  \w     35.00 136.00   1.00    5.46    --  106.95 -61.00-120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0218665000
_diffrn_orient_matrix_UB_12      -0.0216481000
_diffrn_orient_matrix_UB_13      -0.1353839000
_diffrn_orient_matrix_UB_21      0.0187423000
_diffrn_orient_matrix_UB_22      0.0544294000
_diffrn_orient_matrix_UB_23      -0.0557280000
_diffrn_orient_matrix_UB_31      0.1643955000
_diffrn_orient_matrix_UB_32      -0.0091099000
_diffrn_orient_matrix_UB_33      -0.0115943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.619
_diffrn_reflns_theta_min         3.402
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.299
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1798 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.153(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0648
_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^)+(0.0826P)^2^+2.9199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                4637
_reflns_number_total             5018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00562d2.cif
_cod_data_source_block           145
_cod_depositor_comments          'Adding full bibliography for 7135684.cif.'
_cod_database_code               7135684
_shelx_shelxl_version_number     2018/3
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18),
 C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              12925
_shelx_hkl_checksum              90482
_olex2_date_sample_data_collection 2025-02-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.625