The [4 + 2] cyclization/retro-Mannich reaction cascade of para-quinone methide derivatives with Pd-containing 1,4-dipoles.
Jiang, Xiao-Li; Wu, Shu-Fang; Wang, Jin-Rong; Lu, Han; Mei, Guang-Jian; Shi, Feng; Organic & biomolecular chemistry 16 (2018) 8395–8402; doi:10.1039/c8ob01274a

data_7156409
_publ_section_title
;
 The [4 + 2] cyclization/retro-Mannich reaction cascade of para-quinone
 methide derivatives with Pd-containing 1,4-dipoles.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8395
_journal_page_last               8402
_journal_paper_doi               10.1039/c8ob01274a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C30 H35 N O2'
_chemical_formula_sum            'C30 H35 N O2'
_chemical_formula_weight         441.59
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-17 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                88.979(15)
_cell_angle_beta                 78.134(14)
_cell_angle_gamma                86.738(14)
_cell_formula_units_Z            2
_cell_length_a                   10.229(13)
_cell_length_b                   10.292(13)
_cell_length_c                   12.452(16)
_cell_measurement_reflns_used    3090
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.36
_cell_volume                     1281(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8334
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.356
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4937
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1181P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3333
_reflns_number_total             4937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01274a2.cif
_cod_data_source_block           sf_20171026_0m
_cod_depositor_comments          'Adding full bibliography for 7156409.cif.'
_cod_database_code               7156409
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.979
_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, All O(H) groups
2. Restrained distances
 H2-H24C
 2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
  C15(H15), C18(H18), C22(H22)
3.c X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              85643
_olex2_submission_special_instructions 'No special instructions were received'