N-heterocyclic carbene-promoted annulation reaction of allenals with chalcones: synthesis of polysubstituted pyranyl aldehydes.
Ma, Dengke; Qiu, Youai; Dai, Jianxin; Fu, Chunling; Ma, Shengming; Organic letters 16 (2014) 4742–4745; doi:10.1021/ol5021509

data_1517552
_publ_section_title
;
 N-heterocyclic carbene-promoted annulation reaction of allenals with
 chalcones: synthesis of polysubstituted pyranyl aldehydes.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4742
_journal_page_last               4745
_journal_paper_doi               10.1021/ol5021509
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C30 H28 N4 O5'
_chemical_formula_sum            'C30 H28 N4 O5'
_chemical_formula_weight         524.56
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.691(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1313(15)
_cell_length_b                   19.0446(14)
_cell_length_c                   12.9434(16)
_cell_measurement_reflns_used    2156
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4783
_cell_measurement_theta_min      3.1302
_cell_volume                     3007.7(6)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11691
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_platon_squeeze_details
;
;
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2243
_reflns_number_gt                3123
_reflns_number_total             5488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5021509_si_004.cif
_cod_data_source_block           131129_mdk_3_058
_cod_depositor_comments
'Adding full bibliography for 1517550--1517552.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1517552