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_4029915
_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_formula_moiety         'C16 H16 O4'
_chemical_formula_sum            'C16 H16 O4'
_chemical_formula_weight         272.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-11
_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                 91.9617(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.73155(6)
_cell_length_b                   24.5151(2)
_cell_length_c                   13.61877(10)
_cell_measurement_reflns_used    10305
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      75.3210
_cell_measurement_theta_min      4.8410
_cell_volume                     2579.79(3)
_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-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9805
_diffrn_measurement_details
;
  1 omega   70.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000 -180.0000 62

  2 omega  -49.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000  -90.0000 39

  3 omega   10.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000  -90.0000 25

  4 omega -112.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000  -90.0000 99

  5 omega  -48.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000   60.0000 82

  6 omega  -96.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  125.0000   90.0000 94

  7 omega   66.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000   90.0000 74

  8 omega   39.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  150.0000 76

  9 omega   33.00  114.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000    0.0000 81

 10 omega   34.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 41

 11 omega   82.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  -90.0000 96

 12 omega   81.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -180.0000 96

 13 omega   33.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 57

 14 omega   36.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  -30.0000 88
;
_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      0.1379696000
_diffrn_orient_matrix_UB_12      0.0269255000
_diffrn_orient_matrix_UB_13      0.0684239000
_diffrn_orient_matrix_UB_21      0.0636763000
_diffrn_orient_matrix_UB_22      0.0339628000
_diffrn_orient_matrix_UB_23      -0.0868438000
_diffrn_orient_matrix_UB_31      -0.1290244000
_diffrn_orient_matrix_UB_32      0.0455173000
_diffrn_orient_matrix_UB_33      0.0242654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13779
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         4.86
_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    0.826
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56906
_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            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.9341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                4232
_reflns_number_total             4542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501604e_si_005.cif
_cod_data_source_block           song8cult
_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        2579.78(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4029915
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13