Substrate-controlled [4+1] and [3+2] annulations of ninhydrin-derived Morita-Baylis-Hillman carbonates to access polysubstituted furans and cyclopentenes.
Wang, Kai-Kai; Li, Yan-Li; Li, Ya-Fei; Yao, Wei-Wei; Li, Lan-Xin; He, Xiao-Long; Chen, Rongxiang; Chemical communications (Cambridge, England) 60 (2024) 3717–3720; doi:10.1039/d3cc06276g

data_7132804
_publ_section_title
;
 Substrate-controlled [4+1] and [3+2] annulations of ninhydrin-derived
 Morita-Baylis-Hillman carbonates to access polysubstituted furans and
 cyclopentenes.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3717
_journal_page_last               3720
_journal_paper_doi               10.1039/d3cc06276g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C29 H19 N O5'
_chemical_formula_sum            'C29 H19 N O5'
_chemical_formula_weight         461.45
_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     dual
_audit_creation_date             2023-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-03 deposited with the CCDC.	2024-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                100.833(2)
_cell_angle_beta                 92.317(2)
_cell_angle_gamma                115.863(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9434(12)
_cell_length_b                   11.2111(13)
_cell_length_c                   11.3362(13)
_cell_measurement_reflns_used    2416
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.155
_cell_measurement_theta_min      2.742
_cell_volume                     1106.1(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6746
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.742
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0603 before and 0.0263 after correction.
The Ratio of minimum to maximum transmission is 0.8802.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0588P)^2^+0.2905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3401
_reflns_number_total             4834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06276g2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7132804--7132805.cif.'
_cod_database_code               7132804
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C4(H4), C19(H19), C25(H25), C17(H17), C29(H29), C18(H18),
 C3(H3), C1(H1), C28(H28), C27(H27), C2(H2), C26(H26)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              63169
_shelx_hkl_checksum              84835
_olex2_submission_special_instructions 'No special instructions were received'