Organocatalyzed trifunctionalization of alkynyl 1,2-diones for the concise synthesis of acyloxy allylidene malonates and γ-alkylidenebutenolides
Chen, Li; Niu, Shengtong; Lan, Shouang; Liu, Wenjun; Yang, Shuang; Fang, Xinqiang; Green Chemistry 24 (2022) 3623–3628; doi:10.1039/D2GC00061J

data_7244667
_publ_section_title
;
 Organocatalyzed trifunctionalization of alkynyl 1,2-diones for the
 concise synthesis of acyloxy allylidene malonates and
 \g-alkylidenebutenolides
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3623
_journal_page_last               3628
_journal_paper_doi               10.1039/D2GC00061J
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C28 H24 O5'
_chemical_formula_sum            'C28 H24 O5'
_chemical_formula_weight         440.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-29 deposited with the CCDC.	2022-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.333(4)
_cell_length_b                   6.4811(13)
_cell_length_c                   35.365(7)
_cell_measurement_reflns_used    16572
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.6270
_cell_measurement_theta_min      2.1690
_cell_volume                     4660.4(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1130
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            42005
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        24.165
_diffrn_reflns_theta_max         24.165
_diffrn_reflns_theta_min         1.152
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65953
_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            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.8(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         6627
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1542
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.801
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                5472
_reflns_number_total             6627
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00061j2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7244664--7244667.cif.'
_cod_database_code               7244667
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.8(17)
 -0.8(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9), C26(H26), C37(H37), C54(H54)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C42(H42), C43(H43),
 C44(H44), C45(H45), C46(H46), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C55(H55A,H55B,H55C), C56(H56A,H56B,
 H56C)
;
_shelx_res_checksum              2212
_olex2_submission_special_instructions 'No special instructions were received'