Pd(II)-Catalyzed tandem selective dehydrogenative [4+2] annulation of 2-methyl-1,3-cycloalkanediones with olefins.
Zhang, Xu; Wang, Di; Chang, Mengfan; Xu, Xuefeng; Li, Wenguang; Wang, Wanya; Chemical communications (Cambridge, England) 60 (2024) 594–597; doi:10.1039/d3cc05191a

data_7132446
_publ_section_title
;
 Pd(II)-Catalyzed tandem selective dehydrogenative [4+2] annulation of
 2-methyl-1,3-cycloalkanediones with olefins.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              594
_journal_page_last               597
_journal_paper_doi               10.1039/d3cc05191a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C22 H16 O2'
_chemical_formula_sum            'C22 H16 O2'
_chemical_formula_weight         312.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-11-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-29 deposited with the CCDC.	2023-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.830(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.586(5)
_cell_length_b                   21.146(6)
_cell_length_c                   9.659(3)
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.61
_cell_volume                     3183.1(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_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  0.0799
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18502
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.307
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5379
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1063 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.7214.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.2007
_refine_ls_R_factor_gt           0.1203
_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^)+(0.1415P)^2^+10.6552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3299
_refine_ls_wR_factor_ref         0.3739
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3534
_reflns_number_total             7082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05191a2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 7132445--7132446.cif.'
_cod_database_code               7132446
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00O(H00C,H00D), C00G(H00E,H00F), C00I(H00G,H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C00T(H00T), C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C012(H012), C014(H014), C015(H015), C017(H017), C018(H018),
 C00H(H00H), C00P(H00P), C00Q(H00Q), C00V(H00V), C00X(H00X), C011(H011),
 C013(H013), C016(H016), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C)
;
_olex2_submission_special_instructions 'No special instructions were received'