N-Heterocyclic Carbene-Catalyzed Formal [3+2] Annulation of Alkynyl Aldehydes with Nitrosobenzenes: A Highly Regioselective Umpolung Strategy
Han, Runfeng; Qi, Jing; Gu, Jixiang; Ma, Donghui; Xie, Xingang; She, Xuegong; ACS Catalysis 3 (2013) 2705–; doi:10.1021/cs400602v

data_4508603
_publ_section_title
;
 N-Heterocyclic Carbene-Catalyzed Formal [3+2] Annulation of Alkynyl
 Aldehydes with Nitrosobenzenes: A Highly Regioselective Umpolung Strategy
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              2705
_journal_paper_doi               10.1021/cs400602v
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C15 H10 Cl N O2'
_chemical_formula_sum            'C15 H10 Cl N O2'
_chemical_formula_weight         271.69
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.947(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9967(2)
_cell_length_b                   25.9143(12)
_cell_length_c                   12.3646(6)
_cell_measurement_reflns_used    1478
_cell_measurement_temperature    292.23(10)
_cell_measurement_theta_max      28.4074
_cell_measurement_theta_min      3.1381
_cell_volume                     1273.73(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      292.23(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9736
_diffrn_measurement_details
;
  1 omega  -93.00  -58.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.1930  178.0000  120.0000 35

  2 omega  -38.00   85.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -19.0000  -90.0000 123

  3 omega    7.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   13.0000  144.3093 62
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1330701000
_diffrn_orient_matrix_UB_12      0.0181650000
_diffrn_orient_matrix_UB_13      -0.0079128000
_diffrn_orient_matrix_UB_21      0.0604148000
_diffrn_orient_matrix_UB_22      0.0082043000
_diffrn_orient_matrix_UB_23      -0.0491465000
_diffrn_orient_matrix_UB_31      -0.1023850000
_diffrn_orient_matrix_UB_32      -0.0187609000
_diffrn_orient_matrix_UB_33      -0.0291184000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5129
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         3.14
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             560
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0373P)^2^+0.2109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                1922
_reflns_number_total             2877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs400602v_si_001.cif
_cod_data_source_block           exp_470
_cod_original_cell_volume        1273.72(11)
_cod_database_code               4508603
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C8(H8), C12(H12), C5(H5), C11(H11), C2(H2), C1(H1),
 C4(H4), C3(H3)
;