Additive-controlled chemodivergent multi-component domino reaction between salicylaldehydes and Morita-Baylis-Hillman (MBH) carbonates.
Dan Xu, ?; Li, Xiaoxuan; Cai, Yifei; Chen, Yushuang; Xin, Yu; Chen, Jing; Yao, Hui; Huang, Nianyu; Wang, Nengzhong; Chemical communications (Cambridge, England) 61 (2025) 15433–15436; doi:10.1039/d5cc04624f

data_7134920
_publ_section_title
;
 Additive-controlled chemodivergent multi-component domino reaction
 between salicylaldehydes and Morita-Baylis-Hillman (MBH) carbonates.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15433
_journal_page_last               15436
_journal_paper_doi               10.1039/d5cc04624f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-09-12
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-06-11 deposited with the CCDC.	2025-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                93.973(11)
_cell_angle_beta                 90.876(11)
_cell_angle_gamma                92.978(9)
_cell_formula_units_Z            4
_cell_length_a                   7.0689(8)
_cell_length_b                   11.6245(12)
_cell_length_c                   15.613(3)
_cell_measurement_reflns_used    2041
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8520
_cell_measurement_theta_min      2.7860
_cell_volume                     1277.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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      2.00  59.00   1.00    1.50    --   40.73 -38.00  60.00   57
  2  \w     40.00  90.00   1.00    1.50    --   40.73-125.00 -30.00   50
  3  \w     33.00 109.00   1.00    2.00    --  108.83 -30.00  90.00   76
  4  \w    112.00 164.00   1.00    2.00    --  108.83  30.00  30.00   52
  5  \w    146.00 173.00   1.00    2.00    --  108.83 125.00   0.00   27
  6  \w     94.00 133.00   1.00    2.00    --  108.83 125.00   0.00   39
  7  \w     95.00 157.00   1.00    2.00    --  108.83 125.00 120.00   62
  8  \w     96.00 178.00   1.00    2.00    --  108.83  30.00 -90.00   82
  9  \w     61.00 116.00   1.00    2.00    --  108.83-112.00 -16.00   55
 10  \w     59.00 105.00   1.00    2.00    --  108.83 -94.00  60.00   46
 11  \w     36.00 135.00   1.00    2.00    --  108.83 -45.00 -30.00   99
 12  \w     59.00 121.00   1.00    2.00    --  108.83 -30.00-150.00   62
 13  \w     43.00 115.00   1.00    2.00    --  108.83 -61.00-180.00   72
 14  \w     26.00 107.00   1.00    2.00    --  108.83 -94.00 150.00   81
 15  \w    -95.00 -12.00   1.00    2.00    --  -40.73 125.00 150.00   83
 16  \w   -115.00 -18.00   1.00    2.00    --  -40.73 -38.00   0.00   97
 17  \w   -115.00  -7.00   1.00    2.00    --  -40.73 -19.00-120.00  108
 18  \w     72.00  97.00   1.00    2.00    --   40.98-125.00-150.00   25
 19  \w    114.00 140.00   1.00    4.00    --  107.58 125.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0482722000
_diffrn_orient_matrix_UB_12      -0.0678044000
_diffrn_orient_matrix_UB_13      -0.0844350000
_diffrn_orient_matrix_UB_21      -0.0157001000
_diffrn_orient_matrix_UB_22      0.1102260000
_diffrn_orient_matrix_UB_23      -0.0484688000
_diffrn_orient_matrix_UB_31      0.2122859000
_diffrn_orient_matrix_UB_32      0.0308385000
_diffrn_orient_matrix_UB_33      0.0175437000
_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  0.0823
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6071
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6071
_refine_ls_number_restraints     159
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0942
_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^)+(0.1944P)^2^+0.6025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2932
_refine_ls_wR_factor_ref         0.3147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3852
_reflns_number_total             6071
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9216\% 
around [-0.00 -0.01 1.00] (reciprocal) or [0.03 0.09 1.00] (direct)
;
_cod_data_source_file            d5cc04624f2.cif
_cod_data_source_block           lsh-85
_cod_depositor_comments
'Adding full bibliography for 7134919--7134920.cif.'
_cod_database_code               7134920
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.500(3)
 0.500(3)
2. 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
3. Rigid body (RIGU) restrains
 O1, O2, O3, O4, C1, C2, H2, C3, H3, C4, H4, C5, H5, C6, C7, C8, C9, C10, H10,
 C11, C12, H12A, H12B, C13, H13A, H13B, C14, C15, H15A, H15B, C16, H16A, H16B,
 H16C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.006
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C25(H25A,H25B), C26(H26A,
 H26B), C31(H31A,H31B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C18(H18), C19(H19), C20(H20),
 C21(H21), C29(H29)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              50013
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.983
_oxdiff_exptl_absorpt_empirical_full_min 0.628
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2