Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition.
Shu, Tao; Li, Sun; Chen, Xiang-Yu; Liu, Qiang; von Essen, Carolina; Rissanen, Kari; Enders, Dieter; Chemical communications (Cambridge, England) 54 (2018) 7661–7664; doi:10.1039/c8cc04145h

data_7121840
_publ_section_title
;
 Asymmetric synthesis of functionalized tetrahydrofluorenones via an
 NHC-catalyzed homoenolate Michael addition.
;
_journal_issue                   55
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7661
_journal_page_last               7664
_journal_paper_doi               10.1039/c8cc04145h
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H18 O4'
_chemical_formula_sum            'C17 H18 O4'
_chemical_formula_weight         286.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-05-22 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.677(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.69761(17)
_cell_length_b                   12.2794(2)
_cell_length_c                   8.18769(18)
_cell_measurement_reflns_used    5333
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4010
_cell_measurement_theta_min      5.7630
_cell_volume                     724.07(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     29.00  54.00   1.00    1.00    --   41.90  37.00  30.00   25
  2  \w    121.00 177.00   1.00    2.00    --  112.00  77.00   0.00   56
  3  \w    143.00 178.00   1.00    2.00    --  112.00  77.00 -30.00   35
  4  \w    139.00 165.00   1.00    2.00    --  112.00  45.00 -60.00   26
  5  \w    130.00 177.00   1.00    2.00    --  112.00  77.00  30.00   47
  6  \w    130.00 176.00   1.00    2.00    --  112.00  77.00  60.00   46
  7  \w    125.00 176.00   1.00    2.00    --  112.00  75.00 -51.79   51
  8  \w    144.00 175.00   1.00    2.00    --  112.00 111.00-120.00   31
  9  \w     89.00 122.00   1.00    2.00    --  112.00  30.00  30.00   33
 10  \w     87.00 123.00   1.00    2.00    --  112.00  45.00 -30.00   36
 11  \w     84.00 109.00   1.00    2.00    --  112.00  61.00 -30.00   25
 12  \w     87.00 114.00   1.00    2.00    --  112.00  45.00   0.00   27
 13  \w     86.00 113.00   1.00    2.00    --  112.00  61.00   0.00   27
 14  \w     87.00 119.00   1.00    2.00    --  112.00  45.00  30.00   32
 15  \w     91.00 118.00   1.00    2.00    --  112.00  61.00  60.00   27
 16  \w     84.00 109.00   1.00    2.00    --  112.00  61.00  30.00   25
 17  \w     88.00 121.00   1.00    2.00    --  112.00  45.00  60.00   33
 18  \w    110.00 167.00   1.00    2.00    --  112.00  30.00 120.00   57
 19  \w    110.00 161.00   1.00    2.00    --  112.00 111.00 150.00   51
 20  \w     82.00 109.00   1.00    2.00    --  112.00  77.00   0.00   27
 21  \w     82.00 108.00   1.00    2.00    --  112.00  75.00 -51.79   26
 22  \w     84.00 110.00   1.00    2.00    --  112.00  61.00 -60.00   26
 23  \w     86.00 112.00   1.00    2.00    --  112.00  45.00 -60.00   26
 24  \w     79.00 105.00   1.00    2.00    --  112.00  77.00 -30.00   26
 25  \w     81.00 108.00   1.00    2.00    --  112.00  77.00 -60.00   27
 26  \w     79.00 106.00   1.00    2.00    --  112.00  77.00  30.00   27
 27  \w     81.00 119.00   1.00    2.00    --  112.00  77.00  60.00   38
 28  \w     83.00 108.00   1.00    2.00    --  112.00  64.00  53.34   25
 29  \w     61.00  86.00   1.00    2.00    --  112.00  15.00  60.00   25
 30  \w    108.00 145.00   1.00    2.00    --  112.00 -77.00 150.00   37
 31  \w     39.00  72.00   1.00    2.00    --  112.00 -77.00 150.00   33
 32  \w     39.00  99.00   1.00    2.00    --  112.00-111.00  30.00   60
 33  \w     61.00  87.00   1.00    2.00    --  112.00 -77.00-150.00   26
 34  \w     95.00 140.00   1.00    2.00    --  112.00 -77.00-150.00   45
 35  \w     23.00  78.00   1.00    1.00    --   41.90-125.00-180.00   55
 36  \w    -59.00 -33.00   1.00    1.00    --  -41.90 -57.00  30.00   26
 37  \w    -61.00 -34.00   1.00    1.00    --  -41.90 -37.00  30.00   27
 38  \w    -69.00  26.00   1.00    1.00    --  -41.90  57.00  90.00   95
 39  \w    -91.00  -9.00   1.00    1.00    --  -41.90 -77.00-150.00   82
 40  \w   -118.00  -9.00   1.00    1.00    --  -41.90 -77.00 -30.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0075905000
_diffrn_orient_matrix_UB_12      -0.0440766000
_diffrn_orient_matrix_UB_13      0.1735352000
_diffrn_orient_matrix_UB_21      -0.2133386000
_diffrn_orient_matrix_UB_22      -0.0061733000
_diffrn_orient_matrix_UB_23      -0.0814474000
_diffrn_orient_matrix_UB_31      0.0139635000
_diffrn_orient_matrix_UB_32      -0.1173074000
_diffrn_orient_matrix_UB_33      -0.0608229000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6876
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.992
_diffrn_reflns_theta_min         5.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1239 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0790P)^2^+0.0392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                2807
_reflns_number_total             2861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04145h2.cif
_cod_data_source_block           2a
_cod_depositor_comments          'Adding full bibliography for 7121840.cif.'
_cod_database_code               7121840
_chemical_oxdiff_formula         C15H10O4
_reflns_odcompleteness_completeness 99.62
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00E), C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00C(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00E(H00F), C00F(H00G), C00G(H00H), C00J(H00J)
2.d Idealised Me refined as rotating group:
 C00K(H00K,H00L,H00M), C00L(H00N,H00O,H00P)
;
_shelx_res_checksum              1186
_shelx_shelxl_version_number     2014/7
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.633
_oxdiff_exptl_absorpt_empirical_full_min 0.637