Pd-Catalyzed Three-Component Decarboxylative Coupling Reactions Among Alkylidene Pyrazolones, Allyl Carbonates and Active Methylene Compounds
Zhao, Hong-Wu; Zhang, Heng; Cai, Lu-Yu; Wang, Kuo; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00791F

data_7158725
_publ_section_title
;
 Pd-Catalyzed Three-Component Decarboxylative Coupling Reactions Among
 Alkylidene Pyrazolones, Allyl Carbonates and Active Methylene Compounds
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00791F
_journal_year                    2022
_chemical_formula_moiety         'C27 H30 N2 O5'
_chemical_formula_sum            'C27 H30 N2 O5'
_chemical_formula_weight         462.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-16 deposited with the CCDC.	2022-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.428(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.1744(9)
_cell_length_b                   7.6768(3)
_cell_length_c                   29.6328(13)
_cell_measurement_reflns_used    9222
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.5080
_cell_measurement_theta_min      2.1830
_cell_volume                     4989.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_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   -120.00  60.00   1.00    6.00    --  -30.00  45.00   0.00  180
  2  \w   -120.00  60.00   1.00    6.00    --  -30.00  45.00  90.00  180
  3  \w   -120.00  60.00   1.00    6.00    --  -30.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0318855000
_diffrn_orient_matrix_UB_12      -0.0151959000
_diffrn_orient_matrix_UB_13      0.0029612000
_diffrn_orient_matrix_UB_21      -0.0006610000
_diffrn_orient_matrix_UB_22      0.0011825000
_diffrn_orient_matrix_UB_23      -0.0240000000
_diffrn_orient_matrix_UB_31      0.0052948000
_diffrn_orient_matrix_UB_32      0.0911585000
_diffrn_orient_matrix_UB_33      0.0008117000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            25550
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.477
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0586
_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^)+(0.0635P)^2^+3.5663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4320
_reflns_number_total             6133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00791f2.cif
_cod_data_source_block           r20211109b
_cod_database_code               7158725
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C14(H14), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C23(H23A,H23B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              80201
_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 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.845