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_1550528
_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         'C28 H25 N O4 S'
_chemical_formula_sum            'C28 H25 N O4 S'
_chemical_formula_weight         471.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-03-20 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.549(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3488(2)
_cell_length_b                   9.82302(14)
_cell_length_c                   19.2566(4)
_cell_measurement_reflns_used    6370
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5740
_cell_measurement_theta_min      4.8410
_cell_volume                     2214.53(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_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 0.936
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     29.00  79.00   1.00   10.00    --   94.84 -30.00   0.00   50
  2  \w     26.00  97.00   1.00   10.00    --   94.84 -45.00 -60.00   71
  3  \w     22.00  89.00   1.00   10.00    --   94.84 -30.00-180.00   67
  4  \w      9.00 177.00   1.00   10.00    --   94.84   0.00-150.00  168
  5  \w    -45.00  30.00   1.00    3.50    --  -40.75  37.00  90.00   75
  6  \w   -115.00 -15.00   1.00    3.50    --  -40.75 -37.00 150.00  100
  7  \w    -79.00 -16.00   1.00    3.50    --  -40.75 -57.00-120.00   63
  8  \w    -42.00  35.00   1.00    3.50    --  -40.75  37.00 -30.00   77
  9  \w     51.00  87.00   1.00    3.50    --   40.75-125.00 -30.00   36
 10  \w     65.00 109.00   1.00   10.00    --  109.81 -94.00  90.00   44
 11  \w     46.00  96.00   1.00   10.00    --  109.81 -45.00  90.00   50
 12  \w     92.00 118.00   1.00   10.00    --  109.81  30.00  30.00   26
 13  \w     60.00 118.00   1.00   10.00    --  109.81-125.00  90.00   58
 14  \w     51.00  94.00   1.00   10.00    --  109.81 -45.00  30.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1229993000
_diffrn_orient_matrix_UB_12      -0.0196684000
_diffrn_orient_matrix_UB_13      -0.0014492000
_diffrn_orient_matrix_UB_21      0.0009477000
_diffrn_orient_matrix_UB_22      0.1476614000
_diffrn_orient_matrix_UB_23      -0.0267768000
_diffrn_orient_matrix_UB_31      0.0466155000
_diffrn_orient_matrix_UB_32      0.0489909000
_diffrn_orient_matrix_UB_33      0.0800394000
_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     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11619
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         3.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41o (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0388P)^2^+2.7061P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3502
_reflns_number_total             3742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00079h2.cif
_cod_data_source_block           ll-20171007-a
_cod_original_cell_volume        2214.53(8)
_cod_database_code               1550528
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 94.66
_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:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C18(H18A,H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C14(H14), C10(H10), C3(H3), C28(H28), C7(H7), C6(H6),
 C24(H24), C26(H26), C27(H27), C25(H25)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              21622
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.722