Enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (IMBH) reaction of dienones, and elaboration of the IMBH adducts to fluorenones
Satpathi, Bishnupada; Wagulde , Siddhant V.; Ramasastry, S. S. V.; Chem. Commun.  (2017) –; doi:10.1039/C7CC02524F

data_7120337
_publ_section_title
;
 Enantioselective organocatalytic intramolecular Morita-Baylis-Hillman
 (IMBH) reaction of dienones, and elaboration of the IMBH adducts to
 fluorenones
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02524F
_journal_year                    2017
_chemical_formula_moiety         'C13 H12 O2'
_chemical_formula_sum            'C13 H12 O2'
_chemical_formula_weight         200.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-12-03 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                73.986(8)
_cell_angle_beta                 73.564(11)
_cell_angle_gamma                83.983(8)
_cell_formula_units_Z            2
_cell_length_a                   7.8751(9)
_cell_length_b                   8.2320(4)
_cell_length_c                   8.8523(12)
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.3080
_cell_measurement_theta_min      3.0470
_cell_volume                     528.84(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9731
_diffrn_measured_fraction_theta_max 0.9262
_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    -69.00 119.00   0.50    5.00    --   29.89  54.00 -90.00  376
  2  \w    -69.00 119.00   0.50    5.00    --   29.89  54.00 -90.00  376
  3  \w    -69.00 119.00   0.50    5.00    --   29.89  54.00  30.00  376
  4  \w    -69.00 119.00   0.50    5.00    --   29.89  54.00 150.00  376
  5  \w    -69.00  91.00   0.50    5.00    --   29.89  54.00-150.00  320
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0514496000
_diffrn_orient_matrix_UB_12      -0.0001568000
_diffrn_orient_matrix_UB_13      0.0800172000
_diffrn_orient_matrix_UB_21      -0.0761617000
_diffrn_orient_matrix_UB_22      0.0252835000
_diffrn_orient_matrix_UB_23      -0.0294057000
_diffrn_orient_matrix_UB_31      -0.0194445000
_diffrn_orient_matrix_UB_32      -0.0860418000
_diffrn_orient_matrix_UB_33      0.0144776000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11929
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         32.75
_diffrn_reflns_theta_min         2.48
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.2574
_exptl_crystal_description       block
_exptl_crystal_F_000             212.1121
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.7218
_refine_diff_density_min         -0.3509
_refine_diff_density_rms         0.1009
_refine_ls_d_res_high            0.6568
_refine_ls_d_res_low             8.2028
_refine_ls_goodness_of_fit_ref   1.4669
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.4669
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.0969
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2396
_refine_ls_wR_factor_ref         0.2917
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1897
_reflns_number_total             3626
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7cc02524f2.cif
_cod_data_source_block           bsme
_cod_database_code               7120337
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00B(H00B), C008(H008), C009(H009),
 C00A(H00A)
2.c Idealised Me refined as rotating group:
 C00F(H00f,H00g,H00h)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 1.594
_oxdiff_exptl_absorpt_empirical_full_min 0.587