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_7120338
_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_absolute_configuration unk
_chemical_formula_moiety         'C25 H20 O3'
_chemical_formula_sum            'C25 H20 O3'
_chemical_formula_weight         368.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2016-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2016-12-01 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1899(4)
_cell_length_b                   13.3377(5)
_cell_length_c                   14.4940(7)
_cell_measurement_reflns_used    3051
_cell_measurement_theta_max      22.7140
_cell_measurement_theta_min      2.5940
_cell_volume                     1969.88(14)
_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_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9174
_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    -69.00 116.00   0.50    5.00    --   29.89  54.00-120.00  370
  2  \w     -6.00 114.00   0.50    5.00    --   29.89  54.00 120.00  240
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15325
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         32.76
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94152
_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_density_diffrn    1.2422
_exptl_crystal_F_000             776.3947
_refine_diff_density_max         0.2753
_refine_diff_density_min         -0.2001
_refine_diff_density_rms         0.0526
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.6(9)
_refine_ls_d_res_high            0.6568
_refine_ls_d_res_low             7.2470
_refine_ls_goodness_of_fit_ref   1.0529
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     254
_refine_ls_number_reflns         6671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0529
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.0384
_refine_ls_shift/su_mean         0.0016
_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          0.1576
_refine_ls_wR_factor_ref         0.1979
_reflns_Friedel_coverage         0.852
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              19
_reflns_limit_k_min              -19
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                3790
_reflns_number_total             6671
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7cc02524f2.cif
_cod_data_source_block           BS06OMediph
_cod_depositor_comments
;

2018-02-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_original_formula_moiety     '0.5(C25 H20 O3)'
_cod_original_formula_sum        'C12.5 H10 O1.5'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     184.22
_cod_database_code               7120338
_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:
 C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R)
2.c Idealised Me refined as rotating group:
 C00S(H00a,H00b,H00f)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
;