Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene.
Abbasov, Mikail E.; Hudson, Brandi M.; Kong, Weixu; Tantillo, Dean J.; Romo, Daniel; Organic & biomolecular chemistry 15 (2017) 3179–3183; doi:10.1039/c6ob02738e

data_7155534
_publ_section_title
;
 Enantioselective Diels-Alder-lactamization organocascades employing a
 furan-based diene.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3179
_journal_page_last               3183
_journal_paper_doi               10.1039/c6ob02738e
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N O7 S'
_chemical_formula_sum            'C18 H19 N O7 S'
_chemical_formula_weight         393.40
_chemical_name_systematic
'Ethyl (1aS,2S,3R,3aR,6aS,6bS)-4-oxo-5-tosyloctahydro-2,6a-epoxyoxireno[2,3-e]isoindole-3-carboxylate'
_chemical_properties_physical    Heat-sensitive
_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             2015-04-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_audit_update_record
;
2016-05-02 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.069(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8722(5)
_cell_length_b                   6.6204(2)
_cell_length_c                   20.7083(8)
_cell_measurement_reflns_used    9563
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      60.944
_cell_measurement_theta_min      3.980
_cell_volume                     1763.59(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 0.830
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.830
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31880
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         61.119
_diffrn_reflns_theta_min         2.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.019
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1118 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.7625.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       0.0099(8)
_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   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         5106
_refine_ls_number_restraints     166
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0726P)^2^+0.4631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.825
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4758
_reflns_number_total             5106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02738e2.cif
_cod_data_source_block           epon
_cod_depositor_comments          'Adding full bibliography for 7155534.cif.'
_cod_database_code               7155534
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.409
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.98(3) 0.02(3)
2. 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
3. Restrained distances
 C11-C10 = C11A-C10A
 1.54 with sigma of 0.02
 O5-C9 \\sim O5A-C9
 with sigma of 0.005
 O5-C10 \\sim O5A-C10A
 with sigma of 0.005
 O5N-C9M \\sim O5M-C9M
 with sigma of 0.005
 O5M-C10M \\sim O5N-C10N
 with sigma of 0.005
 C11M-C10M \\sim C11N-C10N
 with sigma of 0.005
 O5-C11 \\sim O5A-C11A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C10A \\sim C11A \\sim O5 \\sim C10 \\sim C11 \\sim O5A \\sim O5M \\sim C10M
\\sim C11M \\sim O5N \\sim C10N \\sim C11N \\sim C9 \\sim C9M: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O5) = Uanis(O5A)
Uanis(C11) = Uanis(C11A)
Uanis(O5M) = Uanis(O5N)
Uanis(C10M) = Uanis(C10N)
Uanis(C11M) = Uanis(C11N)
Uanis(O5A) = Uanis(O5)
Uanis(C10A) = Uanis(C10)
5. Same fragment restrains
{O5M, C10M, C11M} sigma for 1-2: 0.005, 1-3: 0.04
as
{O5N, C10N, C11N}
6. Others
 Sof(O5)=Sof(C10)=Sof(H10C)=Sof(H10D)=Sof(C11)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-
 FVAR(1)
 Sof(O5A)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(C11A)=Sof(H11A)=Sof(H11B)=
 Sof(H11C)=FVAR(1)
 Sof(O5N)=Sof(C10N)=Sof(H10G)=Sof(H10H)=Sof(C11N)=Sof(H11J)=Sof(H11K)=
 Sof(H11L)=1-FVAR(2)
 Sof(O5M)=Sof(C10M)=Sof(H10E)=Sof(H10F)=Sof(C11M)=Sof(H11G)=Sof(H11H)=
 Sof(H11I)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C2M(H2M), C5M(H5M), C6M(H6M),
 C7M(H7M), C8M(H8M)
7.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C10A(H10A,H10B), C10(H10C,H10D), C4M(H4MA,H4MB), C10M(H10E,H10F),
  C10N(H10G,H10H)
7.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17), C13M(H13M), C14M(H14M), C16M(H16M),
 C17M(H17M)
7.d Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C11(H11D,H11E,H11F), C18(H18A,H18B,H18C), C11M(H11G,
 H11H,H11I), C11N(H11J,H11K,H11L), C18M(H18D,H18E,H18F)
;
_shelx_res_checksum              60620
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method dichloromethane