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_1550529
_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_absolute_configuration ad
_chemical_formula_moiety         'C28 H24 N2 O7 S'
_chemical_formula_sum            'C28 H24 N2 O7 S'
_chemical_formula_weight         532.55
_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
_audit_creation_date             2018-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-27 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.933(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.68936(19)
_cell_length_b                   16.6569(4)
_cell_length_c                   15.2343(3)
_cell_measurement_reflns_used    4231
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5160
_cell_measurement_theta_min      3.9690
_cell_volume                     2449.63(9)
_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 0.983
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   35.00   88.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000    0.0000 53

  2 omega   63.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000  -90.0000 26

  3 omega   39.00   93.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000 -180.0000 54

  4 omega   34.00  107.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -94.0000 -150.0000 73

  5 omega   33.00   86.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000  -90.0000 53

  6 omega  130.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   45.0000 -180.0000 45

  7 omega   92.00  118.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   45.0000 -180.0000 26

  8 omega   24.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547 -125.0000  -60.0000 57

  9 omega   32.00   90.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000   60.0000 58

 10 omega  116.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  125.0000   60.0000 62

 11 omega   75.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547  167.0000   83.0000 28

 12 omega    3.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547   37.0000 -180.0000 29

 13 omega -119.00   -8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547  -19.0000    0.0000 111

 14 omega -119.00  -92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547 -167.0000   62.0000 27
;
_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      0.0144513000
_diffrn_orient_matrix_UB_12      0.0262810000
_diffrn_orient_matrix_UB_13      -0.0957956000
_diffrn_orient_matrix_UB_21      -0.0310676000
_diffrn_orient_matrix_UB_22      0.0873528000
_diffrn_orient_matrix_UB_23      0.0248675000
_diffrn_orient_matrix_UB_31      0.1558207000
_diffrn_orient_matrix_UB_32      0.0150286000
_diffrn_orient_matrix_UB_33      0.0228516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9116
_diffrn_reflns_point_group_measured_fraction_full 0.698
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.940
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53165
_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_density_diffrn    1.444
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 1413 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         6188
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1151P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1593
_reflns_Friedel_coverage         0.368
_reflns_Friedel_fraction_full    0.391
_reflns_Friedel_fraction_max     0.396
_reflns_number_gt                5742
_reflns_number_total             6188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00079h2.cif
_cod_data_source_block           ll-20180827
_cod_database_code               1550529
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.58
_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:
 C9(H9), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C36(H36A,H36B),
 C38(H38A,H38B), C40(H40A,H40B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C17(H17), C18(H18), C19(H19), C20(H20),
 C23(H23), C24(H24), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33), C34(H34),
  C46(H46), C47(H47), C48(H48), C49(H49), C51(H51), C52(H52), C55(H55), C56(H56)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C54(H54A,H54B,H54C)
;
_olex2_submission_special_instructions 'No special instructions were received'