Metal-Free Alkene Carbooxygenation Following Tandem Intramolecular Alkoxylation/Claisen Rearrangement: Stereocontrolled Access to Bridged [4.2.1] Lactones
Li, Long; Zhu, Xin-Qi; Zhang, Ying-Qi; Bu, Hao-Zhen; Yuan, Peng; Chen, Jinyu; Su, Jingyi; Deng, Xianming; Ye, Long-Wu; Chemical Science  (2019) –; doi:10.1039/C9SC00079H

data_1550527
_publ_section_title
;
 Metal-Free Alkene Carbooxygenation Following Tandem Intramolecular
 Alkoxylation/Claisen Rearrangement: Stereocontrolled Access to Bridged
 [4.2.1] Lactones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00079H
_journal_year                    2019
_chemical_formula_moiety         'C21 H19 N O4 S'
_chemical_formula_sum            'C21 H19 N O4 S'
_chemical_formula_weight         381.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-03-20 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.1959(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.07481(16)
_cell_length_b                   15.0220(2)
_cell_length_c                   12.7620(2)
_cell_measurement_reflns_used    6687
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.8990
_cell_measurement_theta_min      4.5640
_cell_volume                     1717.38(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   11.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5672   57.0000  -30.0000 43

  2 omega   33.00   86.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000 -150.0000 53

  3 omega   46.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000 -180.0000 42

  4 omega   60.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -94.0000 -150.0000 47

  5 omega   54.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000  -60.0000 35

  6 omega   49.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -94.0000  -60.0000 59

  7 omega   50.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -94.0000   30.0000 42

  8 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000    0.0000 58

  9 omega   79.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   30.0000  -30.0000 99

 10 omega  127.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   61.0000  -90.0000 49

 11 omega   85.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   45.0000 -120.0000 93

 12 omega   44.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5672 -125.0000 -180.0000 52

 13 omega   26.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5672 -125.0000  -90.0000 58

 14 omega   38.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000  -90.0000 60

 15 omega   36.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -61.0000   90.0000 80

 16 omega   73.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067 -125.0000  150.0000 47

 17 omega   32.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000  150.0000 34

 18 omega  -48.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672   37.0000  -30.0000 84

 19 omega  -48.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672   37.0000  150.0000 83

 20 omega -116.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -77.0000    0.0000 106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1617285000
_diffrn_orient_matrix_UB_12      0.0255658000
_diffrn_orient_matrix_UB_13      0.0465582000
_diffrn_orient_matrix_UB_21      -0.0490342000
_diffrn_orient_matrix_UB_22      0.0972997000
_diffrn_orient_matrix_UB_23      0.0110434000
_diffrn_orient_matrix_UB_31      -0.0323423000
_diffrn_orient_matrix_UB_32      -0.0200520000
_diffrn_orient_matrix_UB_33      0.1124212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10760
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.581
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetatete'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.9419P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2966
_reflns_number_total             3057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00079h2.cif
_cod_data_source_block           ll_170506
_cod_database_code               1550527
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C12(H12), C6(H6), C5(H5), C11(H11), C2(H2), C9(H9)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'