Catalytic Chemo- and Regioselective Coupling of 1,3-Dicarbonyls with N-Heterocyclic Nucleophiles.
Kenny, Miles; Kitson, Daniel J.; Franckevičius, Vilius; The Journal of organic chemistry 81 (2016) 5162–5172; doi:10.1021/acs.joc.6b00731

data_4036861
_publ_section_title
;
 Catalytic Chemo- and Regioselective Coupling of 1,3-Dicarbonyls with
 N-Heterocyclic Nucleophiles.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5162
_journal_page_last               5172
_journal_paper_doi               10.1021/acs.joc.6b00731
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C17 H21 N O4'
_chemical_formula_sum            'C17 H21 N O4'
_chemical_formula_weight         303.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                85.356(2)
_cell_angle_beta                 85.858(2)
_cell_angle_gamma                80.981(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7520(2)
_cell_length_b                   8.3609(2)
_cell_length_c                   13.8172(3)
_cell_measurement_reflns_used    8947
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      73.7100
_cell_measurement_theta_min      5.3250
_cell_volume                     766.44(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2303
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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    -59.00  33.00   1.00    5.00    --  -38.50  38.00 -60.00   92
  2  \w    -69.00  33.00   1.00    5.00    --  -38.50  77.00  30.00  102
  3  \w     12.00 113.00   1.00    5.00    --   42.14  77.00 150.00  101
  4  \w     84.00 178.00   1.00   20.00    --  104.55  30.00  30.00   94
  5  \w     94.00 175.00   1.00   20.00    --  104.55 125.00  90.00   81
  6  \w     35.00 121.00   1.00   20.00    --  104.55-125.00   0.00   86
  7  \w     84.00 178.00   1.00   20.00    --  104.55  30.00-180.00   94
  8  \w     33.00 135.00   1.00   20.00    --  104.55 -77.00 150.00  102
  9  \w     35.00 121.00   1.00   20.00    --  104.55-125.00 150.00   86
 10  \w     36.00 131.00   1.00   20.00    --  104.55 -61.00 -60.00   95
 11  \w     78.00 173.00   1.00   20.00    --  104.55  61.00-150.00   95
 12  \w     78.00 173.00   1.00   20.00    --  104.55  61.00 -90.00   95
 13  \w     12.00 113.00   1.00    5.00    --   42.14  77.00-120.00  101
 14  \w     17.00 111.00   1.00    5.00    --   42.14  57.00  60.00   94
 15  \w     17.00 111.00   1.00    5.00    --   42.14  57.00 -30.00   94
 16  \w     78.00 173.00   1.00   20.00    --  104.55  61.00 120.00   95
 17  \w     78.00 173.00   1.00   20.00    --  104.55  61.00 -30.00   95
 18  \w     74.00 176.00   1.00   20.00    --  104.55  77.00  30.00  102
 19  \w     78.00 173.00   1.00   20.00    --  104.55  61.00-180.00   95
 20  \w     78.00 173.00   1.00   20.00    --  104.55  61.00 -60.00   95
 21  \w     82.00 174.00   1.00   20.00    --  104.55  45.00  90.00   92
 22  \w      1.00  81.00   1.00    5.00    --   42.14 -99.00-180.00   80
 23  \w     12.00 113.00   1.00    5.00    --   42.14  77.00 -60.00  101
 24  \w     12.00 113.00   1.00    5.00    --   42.14  77.00  60.00  101
 25  \w     74.00 111.00   1.00   20.00    --  104.55  77.00   0.00   37
;
_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      -0.0499276000
_diffrn_orient_matrix_UB_12      0.0504087000
_diffrn_orient_matrix_UB_13      -0.1062509000
_diffrn_orient_matrix_UB_21      -0.1880707000
_diffrn_orient_matrix_UB_22      0.1143046000
_diffrn_orient_matrix_UB_23      0.0356088000
_diffrn_orient_matrix_UB_31      0.1253123000
_diffrn_orient_matrix_UB_32      0.1391919000
_diffrn_orient_matrix_UB_33      -0.0014084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11458
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.897
_diffrn_reflns_theta_min         5.370
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0434P)^2^+0.3024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2936
_reflns_number_total             3051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00731_si_003.cif
_cod_data_source_block           vf100
_cod_original_cell_volume        766.44(4)
_cod_database_code               4036861
_chemical_oxdiff_formula         'C34 H38 N2 O8 '
_chemical_oxdiff_usercomment     MK253
_reflns_odcompleteness_completeness 97.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.73
_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 Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              27235
_shelx_hkl_checksum              5357
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method
'mounted on a polyimide loop using Paratone-N oil'
_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.601