Synthesis of functionalized γ-lactones via a three-component cascade reaction catalyzed by consecutive N-heterocyclic carbene systems
Huang, Wei; Zhao, Qian; Han, Bo; Wang, Biao; Leng, Hai-Jun; Peng, Cheng; RSC Adv.  (2015) –; doi:10.1039/C5RA01254F

data_7219766
_publ_section_title
;
 Synthesis of functionalized \g-lactones via a three-component cascade
 reaction catalyzed by consecutive N-heterocyclic carbene systems
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA01254F
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H18 O3'
_chemical_formula_sum            'C23 H18 O3'
_chemical_formula_weight         342.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_block_doi                 10.5517/cc115sss
_audit_creation_date             2013-08-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
;
2013-09-03 deposited with the CCDC.
2015-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.811(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7969(3)
_cell_length_b                   14.0639(6)
_cell_length_c                   9.4194(4)
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5140
_cell_measurement_theta_min      8.2660
_cell_volume                     894.05(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2563
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.8339
_diffrn_measurement_details
;
  1 omega  -18.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 49

  2 omega  -79.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 46

  3 omega  -82.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  -60.0000 25

  4 omega   38.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 28

  5 omega  -67.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000   90.0000 25

  6 omega -112.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.4922  -94.0000   30.0000 32

  7 omega -111.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.4922  -94.0000 -120.0000 31

  8 omega -124.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.4922  -61.0000   90.0000 87

  9 omega -130.00  -93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -56.4922  -94.0000   90.0000 37

 10 omega   18.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.4922 -125.0000   90.0000 98

 11 omega   33.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.4922   61.0000  -60.0000 85

 12 omega   20.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.4922 -125.0000  -90.0000 46

 13 omega   24.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.4922  -45.0000   60.0000 58

 14 omega  -56.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   50.0000 -120.0000 27

 15 omega  -72.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   63.0000   30.0000 64

 16 omega   44.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -77.0000   90.0000 82

 17 omega  100.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  111.0000  120.0000 27

 18 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843 -111.0000 -150.0000 27

 19 omega   49.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -91.0000 -120.0000 100

 20 omega   50.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843   12.0000  -60.0000 128

 21 omega   85.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843   50.0000 -180.0000 59

 22 omega   36.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -25.0000  -30.0000 55

 23 omega   41.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -50.0000 -150.0000 58

 24 omega   46.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -50.0000   90.0000 54

 25 omega   41.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -50.0000  -90.0000 41

 26 omega   39.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -37.0000  150.0000 49

 27 omega   45.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843 -111.0000   60.0000 70

 28 omega   36.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -25.0000  -90.0000 58

 29 omega   39.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843  -37.0000   30.0000 53

 30 omega   41.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.9843 -111.0000   90.0000 33
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0670321000
_diffrn_orient_matrix_UB_12      -0.0548708000
_diffrn_orient_matrix_UB_13      0.1389477000
_diffrn_orient_matrix_UB_21      -0.0992250000
_diffrn_orient_matrix_UB_22      -0.0908147000
_diffrn_orient_matrix_UB_23      -0.0661350000
_diffrn_orient_matrix_UB_31      0.1942667000
_diffrn_orient_matrix_UB_32      -0.0273935000
_diffrn_orient_matrix_UB_33      -0.0587059000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5229
_diffrn_reflns_theta_full        67.24
_diffrn_reflns_theta_max         67.24
_diffrn_reflns_theta_min         4.73
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0245(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0470P)^2^+0.0661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                2601
_reflns_number_total             2737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra01254f2.cif
_cod_data_source_block           exp_3159
_cod_database_code               7219766
_chemical_oxdiff_formula         C10H11O2S
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.072) H2(0.091) H3(0.085) H4(0.069) H5(0.057) H9(0.049)
 H10A(0.061) H10B(0.061) H13(0.057) H14(0.069) H15(0.074) H16(0.075) H17(0.06)
 H19(0.069) H20(0.089) H21(0.093) H22(0.089) H23(0.07)
 Fixed X: H1(-0.0367) H2(-0.1025) H3(0.1388) H4(0.4494) H5(0.5218) H9(0.4048)
 H10A(0.814) H10B(0.7083) H13(0.3491) H14(0.4867) H15(0.8047) H16(0.9856)
 H17(0.8515) H19(0.1927) H20(0.1276) H21(0.3714) H22(0.6761) H23(0.74)
 Fixed Y: H1(0.473) H2(0.5613) H3(0.6579) H4(0.6647) H5(0.5731) H9(0.2927)
 H10A(0.3197) H10B(0.2259) H13(0.5421) H14(0.6683) H15(0.7187) H16(0.6424)
 H17(0.516) H19(0.2926) H20(0.3035) H21(0.357) H22(0.3999) H23(0.3912)
 Fixed Z: H1(0.2316) H2(0.0258) H3(-0.0502) H4(0.0777) H5(0.2802) H9(0.5169)
 H10A(0.6019) H10B(0.5399) H13(0.6633) H14(0.7981) H15(0.774) H16(0.6171)
 H17(0.4832) H19(0.6886) H20(0.9246) H21(1.0976) H22(1.0362) H23(0.8017)
;