Cascade Michael Addition/Cycloketalization of Cyclic 1,3-Dicarbonyl Compounds: Important Role of the Tethered Alcohol of α,β-Unsaturated Carbonyl Compounds on Reaction Rate and Regioselectivity.
Yao, Hongliang; Song, Liyan; Liu, Yuan; Tong, Rongbiao; The Journal of organic chemistry 79 (2014) 8774–8785; doi:10.1021/jo501604e

data_4029910
_publ_section_title
;
 Cascade Michael Addition/Cycloketalization of Cyclic 1,3-Dicarbonyl
 Compounds: Important Role of the Tethered Alcohol of \a,\b-Unsaturated
 Carbonyl Compounds on Reaction Rate and Regioselectivity.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8774
_journal_page_last               8785
_journal_paper_doi               10.1021/jo501604e
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H16 O5'
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-04
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.242(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4927(4)
_cell_length_b                   6.17535(17)
_cell_length_c                   16.8213(5)
_cell_measurement_reflns_used    3913
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      75.1780
_cell_measurement_theta_min      5.0540
_cell_volume                     1257.82(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.97(13)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9633
_diffrn_measured_fraction_theta_max 0.8997
_diffrn_measurement_details
;
  1 omega   38.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -180.0000 70

  2 omega -116.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -77.0000   60.0000 103

  3 omega  -71.00   30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   77.0000  -90.0000 101

  4 omega  -44.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000 -180.0000 78

  5 omega  -43.00   16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000  120.0000 59

  6 omega   34.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 55

  7 omega   45.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -180.0000 45

  8 omega   49.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -90.0000 55

  9 omega   33.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   60.0000 52

 10 omega   97.00  153.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -90.0000 56

 11 omega   36.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -32.0000  -68.0000 51

 12 omega   38.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -30.0000 52

 13 omega   32.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   90.0000 75

 14 omega   35.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 41

 15 omega   50.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -30.0000 58

 16 omega   78.00  153.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000  -30.0000 75
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0864568000
_diffrn_orient_matrix_UB_12      -0.1088519000
_diffrn_orient_matrix_UB_13      -0.0383790000
_diffrn_orient_matrix_UB_21      0.0524885000
_diffrn_orient_matrix_UB_22      0.2225901000
_diffrn_orient_matrix_UB_23      -0.0072845000
_diffrn_orient_matrix_UB_31      0.0771324000
_diffrn_orient_matrix_UB_32      -0.0297393000
_diffrn_orient_matrix_UB_33      0.0859953000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6656
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.46
_diffrn_reflns_theta_min         3.98
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.832
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.2472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                3939
_reflns_number_total             4262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501604e_si_009.cif
_cod_data_source_block           liang11a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029910--4029917.cif.
;
_cod_original_cell_volume        1257.83(7)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4029910
_reflns_odcompleteness_completeness 96.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13