Silver-Promoted Regioselective [4+2] Annulation Reaction of Indoles with Alkenes to Construct Dihydropyrimidoindolone Scaffolds
Zhang, Lin-Bao; Zhu, Ming-Hui; Du, Wu-Bo; Ni, Shao-Fei; Wen, Li-Rong; Li, Ming; Chemical Communications  (2019) –; doi:10.1039/C9CC07098B

data_7124436
_publ_section_title
;
 Silver-Promoted Regioselective [4+2] Annulation Reaction of Indoles with
 Alkenes to Construct Dihydropyrimidoindolone Scaffolds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07098B
_journal_year                    2019
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-05-03 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.139(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.350(3)
_cell_length_b                   13.447(4)
_cell_length_c                   10.912(3)
_cell_measurement_reflns_used    5065
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4767
_cell_measurement_theta_min      1.5144
_cell_volume                     1582.7(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10516
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         1.888
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.408
_exptl_crystal_size_min          0.264
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0325P)^2^+0.6398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3414
_reflns_number_total             3590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07098b2.cif
_cod_data_source_block           a
_cod_original_cell_volume        1582.6(8)
_cod_database_code               7124436
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.959
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              28411
_olex2_submission_special_instructions 'No special instructions were received'