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_1550531
_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         'C14 H12 F N O2'
_chemical_formula_sum            'C14 H12 F N O2'
_chemical_formula_weight         245.25
_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             2017-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2018-03-20 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.137(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.45155(15)
_cell_length_b                   18.5193(4)
_cell_length_c                   11.2116(3)
_cell_measurement_reflns_used    2670
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      74.7530
_cell_measurement_theta_min      4.6680
_cell_volume                     1106.61(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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   32.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000    0.0000 30

  2 omega   38.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000   60.0000 26

  3 omega   38.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000  120.0000 51

  4 omega   36.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547 -125.0000    0.0000 35

  5 omega   25.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547 -125.0000 -120.0000 25

  6 omega   52.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000 -120.0000 38

  7 omega   82.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   30.0000 -180.0000 96

  8 omega   84.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067   45.0000 -120.0000 91

  9 omega   42.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -45.0000  -60.0000 46

 10 omega   36.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      109.8067  -30.0000  -60.0000 26

 11 omega  -97.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547    0.0000   60.0000 139

 12 omega -129.00 -103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547    0.0000   60.0000 26
;
_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      0.0074239000
_diffrn_orient_matrix_UB_12      0.0570944000
_diffrn_orient_matrix_UB_13      0.1006035000
_diffrn_orient_matrix_UB_21      0.2869762000
_diffrn_orient_matrix_UB_22      0.0059020000
_diffrn_orient_matrix_UB_23      0.0152135000
_diffrn_orient_matrix_UB_31      -0.0354339000
_diffrn_orient_matrix_UB_32      0.0601415000
_diffrn_orient_matrix_UB_33      -0.0969477000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3637
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         4.688
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79554
_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    1.472
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0598P)^2^+0.4767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1868
_reflns_number_total             1954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00079h2.cif
_cod_data_source_block           ll-20171112
_cod_database_code               1550531
_reflns_odcompleteness_completeness 99.52
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C0AA(H0AA), C5(H5), C6(H6)
;
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'