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_7244664
_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         'C29 H24 O5'
_chemical_formula_sum            'C29 H24 O5'
_chemical_formula_weight         452.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-26
_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                83.076(2)
_cell_angle_beta                 88.393(2)
_cell_angle_gamma                84.055(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1359(3)
_cell_length_b                   10.8744(3)
_cell_length_c                   12.1839(2)
_cell_measurement_reflns_used    7421
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      73.6010
_cell_measurement_theta_min      3.6460
_cell_volume                     1195.00(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9650
_diffrn_measured_fraction_theta_max 0.9650
_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    -51.00  22.00   0.50    0.50    --    0.00 -57.00  30.00  146
  2  \w    -22.00   4.00   0.50    0.50    --    0.00 -57.00 -60.00   52
  3  \w    -18.00  89.00   0.50    0.50    --    0.00  19.00  30.00  214
  4  \w    -89.00 -59.00   0.50    0.50    --    0.00 -57.00  30.00   60
  5  \w     -6.00  21.00   0.50    0.50    --    0.00  77.00  60.00   54
  6  \w    -49.00 -24.00   0.50    0.50    --    0.00 -57.00 -60.00   50
  7  \w     76.00 102.00   0.50    0.50    --   95.20 -82.00 -90.00   52
  8  \w      6.00  33.00   0.50    0.50    --   95.20 -82.00 -90.00   54
  9  \w      6.00 118.00   0.50    0.50    --   95.20 -61.00 -30.00  224
 10  \w     78.00 104.00   0.50    0.50    --   95.20 -82.00  90.00   52
 11  \w     20.00 127.00   0.50    0.50    --   95.20 -82.00 -30.00  214
 12  \w     21.00 111.00   0.50    0.50    --   95.20 -61.00  60.00  180
 13  \w     76.00 102.00   0.50    0.50    --   95.20 -30.00   0.00   52
 14  \w    117.00 173.00   0.50    0.50    --   95.20  15.00   0.00  112
 15  \w     81.00 120.00   0.50    0.50    --   95.20 -82.00  60.00   78
 16  \w      7.00  56.00   0.50    0.50    --   95.20 -30.00   0.00   98
 17  \w     31.00  56.00   0.50    0.50    --   95.20 -82.00  60.00   50
 18  \w     95.00 120.00   0.50    0.50    --   95.20  30.00  30.00   50
 19  \w    136.00 179.00   0.50    0.50    --   95.20  30.00  30.00   86
 20  \w     90.00 180.00   0.50    0.50    --   95.20  45.00 -60.00  180
 21  \w     33.00 127.00   0.50    0.50    --   95.20 -82.00-180.00  188
 22  \w     15.00 118.00   0.50    0.50    --   95.20 -61.00-180.00  206
 23  \w     85.00 183.00   0.50    0.50    --   95.20  45.00 -90.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0227978000
_diffrn_orient_matrix_UB_12      0.1382000000
_diffrn_orient_matrix_UB_13      -0.0320778000
_diffrn_orient_matrix_UB_21      0.0252461000
_diffrn_orient_matrix_UB_22      0.0138229000
_diffrn_orient_matrix_UB_23      0.1222101000
_diffrn_orient_matrix_UB_31      0.1661136000
_diffrn_orient_matrix_UB_32      -0.0358516000
_diffrn_orient_matrix_UB_33      -0.0162208000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12060
_diffrn_reflns_theta_full        74.2440
_diffrn_reflns_theta_max         74.24
_diffrn_reflns_theta_min         3.65
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2575
_exptl_crystal_description       block
_exptl_crystal_F_000             477.5839
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.2105
_refine_diff_density_min         -0.2912
_refine_diff_density_rms         0.0590
_refine_ls_d_res_high            0.8010
_refine_ls_d_res_low             12.0935
_refine_ls_goodness_of_fit_ref   1.0271
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0271
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0876P)^2^+0.2006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4096
_reflns_number_total             4710
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2gc00061j2.cif
_cod_data_source_block           F4
_cod_depositor_comments
'Adding full bibliography for 7244664--7244667.cif.'
_cod_database_code               7244664
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C00M(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X),
 C00Y(H00Y)
2.c Idealised Me refined as rotating group:
 C00W(H00c,H00d,H00g)
;
_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 5.649
_oxdiff_exptl_absorpt_empirical_full_min 0.399