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_4029914
_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         'C12 H16 O3'
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 99.830(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.9743(11)
_cell_length_b                   5.1150(3)
_cell_length_c                   10.7934(6)
_cell_measurement_reflns_used    960
_cell_measurement_temperature    99.95(13)
_cell_measurement_theta_max      73.8600
_cell_measurement_theta_min      8.9910
_cell_volume                     1032.16(10)
_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    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      99.95(13)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9868
_diffrn_measured_fraction_theta_max 0.9492
_diffrn_measurement_details
;
  1 omega   41.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8203  -30.0000 -120.0000 42

  2 omega -114.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3203  -57.0000  120.0000 103

  3 omega  -47.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3203   37.0000  -90.0000 83

  4 omega   49.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8203 -125.0000  120.0000 68

  5 omega   34.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8203  -30.0000  -30.0000 55

  6 omega   44.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8203  -94.0000 -180.0000 64

  7 omega   56.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8203  -30.0000 -180.0000 33

  8 omega   35.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8203  -30.0000  150.0000 45

  9 omega   43.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      111.8203  -77.0000  -90.0000 94
;
_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      -0.0130037000
_diffrn_orient_matrix_UB_12      0.2240802000
_diffrn_orient_matrix_UB_13      0.0887033000
_diffrn_orient_matrix_UB_21      0.0353601000
_diffrn_orient_matrix_UB_22      -0.1627620000
_diffrn_orient_matrix_UB_23      0.1139702000
_diffrn_orient_matrix_UB_31      0.0732765000
_diffrn_orient_matrix_UB_32      0.1184111000
_diffrn_orient_matrix_UB_33      -0.0113895000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1459
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.47
_diffrn_reflns_theta_min         4.73
_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    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66424
_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            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1047
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0868P)^2^+0.6483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                1028
_reflns_number_total             1047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501604e_si_006.cif
_cod_data_source_block           liang6cult
_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_sg_symbol_H-M      Cc
_cod_database_code               4029914
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13