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_1517551
_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         'C27 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.759(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   28.281(2)
_cell_length_b                   6.5273(6)
_cell_length_c                   38.133(4)
_cell_measurement_reflns_used    2302
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3149
_cell_measurement_theta_min      3.6483
_cell_volume                     6703.9(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0379213000
_diffrn_orient_matrix_UB_12      0.0192289000
_diffrn_orient_matrix_UB_13      -0.0214917000
_diffrn_orient_matrix_UB_21      -0.0015076000
_diffrn_orient_matrix_UB_22      -0.2337781000
_diffrn_orient_matrix_UB_23      -0.0057222000
_diffrn_orient_matrix_UB_31      -0.0428148000
_diffrn_orient_matrix_UB_32      0.0254986000
_diffrn_orient_matrix_UB_33      -0.0361251000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_unetI/netI     0.1309
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            24600
_diffrn_reflns_theta_full        67.43
_diffrn_reflns_theta_max         67.43
_diffrn_reflns_theta_min         4.44
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     874
_refine_ls_number_reflns         11779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1724
_refine_ls_R_factor_gt           0.0723
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.2235
_reflns_number_gt                4667
_reflns_number_total             11779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5021509_si_002.cif
_cod_data_source_block           140417_mdk_4_073_1
_cod_depositor_comments
'Adding full bibliography for 1517550--1517552.cif.'
_cod_original_cell_volume        6703.9(10)
_cod_database_code               1517551
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C48) = Uanis(C48A)
3. Others
 Sof(H47C)=Sof(H47D)=Sof(C48A)=Sof(H48D)=Sof(H48E)=Sof(H48F)=1-FVAR(1)
 Sof(H47A)=Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C9(H9), C19(H19), C36(H36), C46(H46), C63(H63), C73(H73)
4.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C47(H47A,H47B), C47(H47C,H47D), C74(H74A,H74B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C39(H39), C40(H40),
 C41(H41), C42(H42), C43(H43), C44(H44), C50(H50), C51(H51), C52(H52), C53(H53),
  C54(H54), C56(H56), C57(H57), C59(H59), C60(H60), C62(H62), C67(H67),
 C68(H68), C69(H69), C70(H70), C71(H71), C72(H72), C77(H77), C78(H78), C79(H79),
  C80(H80), C81(H81)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C48(H48A,H48B,H48C), C75(H75A,H75B,H75C), C48A(H48D,H48E,
 H48F)
;