Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones.
Kim, Jungwon; Hong, Soon Hyeok; Chemical science 8 (2017) 2401–2406; doi:10.1039/c6sc05266e

data_1544826
_publ_section_title
;
 Organocatalytic activation of isocyanides: N-heterocyclic
 carbene-catalyzed enaminone synthesis from ketones.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              2401
_journal_page_last               2406
_journal_paper_doi               10.1039/c6sc05266e
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C17 H17 N O'
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.31
_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
_audit_creation_date             2016-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-08 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0107(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.39890(8)
_cell_length_b                   11.27072(15)
_cell_length_c                   19.0731(3)
_cell_measurement_reflns_used    8240
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      76.2470
_cell_measurement_theta_min      4.5340
_cell_volume                     1374.71(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -96.00  -2.00   1.00    1.17    --  -41.24 125.00 150.00   94
  2  \w    -66.00  33.00   1.00    1.17    --  -41.24  38.00-150.00   99
  3  \w    -82.00  39.00   1.00    1.17    --  -41.24  19.00 150.00  121
  4  \w     17.00 116.00   1.00    1.17    --   41.24  38.00-180.00   99
  5  \w     17.00 116.00   1.00    1.17    --   41.24  38.00 -30.00   99
  6  \w      1.00  82.00   1.00    1.17    --   41.24 -99.00 -60.00   81
  7  \w    100.00 178.00   1.00    3.59    --  112.00 111.00 -30.00   78
  8  \w     29.00 109.00   1.00    3.59    --  112.00 -94.00 -90.00   80
  9  \w     57.00 151.00   1.00    3.59    --  112.00 178.00-180.00   94
 10  \w     29.00 109.00   1.00    3.59    --  112.00 -94.00 120.00   80
 11  \w     36.00 116.00   1.00    3.59    --  112.00-111.00 -30.00   80
 12  \w    100.00 178.00   1.00    3.59    --  112.00 111.00   0.00   78
 13  \w     36.00 140.00   1.00    3.59    --  112.00 -30.00   0.00  104
 14  \w     84.00 178.00   1.00    3.59    --  112.00  30.00 -90.00   94
 15  \w     36.00 140.00   1.00    3.59    --  112.00 -30.00 120.00  104
 16  \w     86.00 178.00   1.00    3.59    --  112.00  45.00 -60.00   92
 17  \w     29.00 109.00   1.00    3.59    --  112.00 -94.00-120.00   80
 18  \w     77.00 104.00   1.00    3.59    --  112.00 -94.00  30.00   27
 19  \w     43.00  70.00   1.00    3.59    --  112.00 -94.00  30.00   27
 20  \w     89.00 161.00   1.00    3.59    --  112.00  45.00 -30.00   72
 21  \w    141.00 168.00   1.00    3.59    --  112.00 111.00 -90.00   27
 22  \w     82.00 115.00   1.00    3.59    --  112.00-111.00   0.00   33
 23  \w     71.00 104.00   1.00    3.59    --  112.00 -94.00  60.00   33
 24  \w     44.00 136.00   1.00    3.59    --  112.00 -61.00 -60.00   92
 25  \w     67.00 117.00   1.00    3.59    --  112.00 -61.00  90.00   50
 26  \w     30.00 125.00   1.00    3.59    --  112.00 -15.00-150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0620325000
_diffrn_orient_matrix_UB_12      -0.1261012000
_diffrn_orient_matrix_UB_13      0.0240189000
_diffrn_orient_matrix_UB_21      0.0201080000
_diffrn_orient_matrix_UB_22      0.0434530000
_diffrn_orient_matrix_UB_23      0.0765340000
_diffrn_orient_matrix_UB_31      -0.2318118000
_diffrn_orient_matrix_UB_32      -0.0299494000
_diffrn_orient_matrix_UB_33      0.0100900000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16312
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.484
_diffrn_reflns_theta_min         4.558
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.4720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2626
_reflns_number_total             2863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05266e2.cif
_cod_data_source_block           exp_358
_cod_depositor_comments
;Adding full bibliography for 1544826.cif.

 Adding full bibliography for 1544826.cif.
;
_cod_database_code               1544826
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         C17H17N1O1
_chemical_oxdiff_usercomment     JWKim_No.7_p.92B-p/DMA
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
;
_olex2_date_sample_data_collection 2016-06-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.714