Intramolecular [3 + 2] nitrone cycloaddition reaction: highly regio and diastereoselective synthesis of bicyclo[3.2.1]octane scaffolds.
Bakthadoss, Manickam; Mushaf, Mohammad; Organic & biomolecular chemistry 18 (2020) 9653–9659; doi:10.1039/d0ob01960g

data_7157759
_publ_section_title
;
 Intramolecular [3 + 2] nitrone cycloaddition reaction: highly regio and
 diastereoselective synthesis of bicyclo[3.2.1]octane scaffolds.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9653
_journal_page_last               9659
_journal_paper_doi               10.1039/d0ob01960g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C16 H18 Cl N O6'
_chemical_formula_sum            'C16 H18 Cl N O6'
_chemical_formula_weight         355.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-15
_audit_creation_method
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Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
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_audit_update_record
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2020-07-15 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.377(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0420(5)
_cell_length_b                   8.8933(5)
_cell_length_c                   16.9598(12)
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    295
_cell_measurement_theta_max      29.1464
_cell_measurement_theta_min      3.6127
_cell_volume                     1658.12(17)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9935
_diffrn_measured_fraction_theta_max 0.8706
_diffrn_measurement_details
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  1 omega  -75.00  -46.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  127.0000 -119.0000 29

  2 omega  -87.00  -58.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  120.0000 29

  3 omega   -7.00   21.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000  150.0000 28

  4 omega  -16.00   14.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000    0.0000 30

  5 omega  -13.00   24.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000 -150.0000 37

  6 omega  -64.00  -35.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397 -178.0000  -90.0000 29

  7 omega  -80.00  -54.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  147.0000  -88.0000 26

  8 omega  -15.00   41.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000 -150.0000 56

  9 omega  -71.00    9.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -77.0000  150.0000 80

 10 omega   19.00   88.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1366   57.0000   90.0000 69
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_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0003323000
_diffrn_orient_matrix_UB_12      -0.0726909000
_diffrn_orient_matrix_UB_13      -0.0172538000
_diffrn_orient_matrix_UB_21      -0.0142660000
_diffrn_orient_matrix_UB_22      0.0321036000
_diffrn_orient_matrix_UB_23      -0.0379848000
_diffrn_orient_matrix_UB_31      0.0629449000
_diffrn_orient_matrix_UB_32      0.0069272000
_diffrn_orient_matrix_UB_33      -0.0047099000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11912
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         3.62
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4251
_exptl_crystal_description       block
_exptl_crystal_F_000             745.0328
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.3837
_refine_diff_density_min         -0.4095
_refine_diff_density_rms         0.0771
_refine_ls_d_res_high            0.7282
_refine_ls_d_res_low             5.6284
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0578
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0578
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0856P)^2^+0.5350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1771
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                2609
_reflns_number_total             3917
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0ob01960g2.cif
_cod_data_source_block           MB-MM-444-S
_cod_depositor_comments          'Adding full bibliography for 7157759.cif.'
_cod_original_cell_volume        1658.10(17)
_cod_original_sg_symbol_Hall     '-P 2ybc (z,y,-x)'
_cod_database_code               7157759
_chemical_oxdiff_formula         'C34 H26 N2 O11'
_chemical_oxdiff_usercomment     'COLOURLESS BLOCK, 295K, 0.48 0.3 0.13'
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C16(H16a,H16b,H16c), C15(H15a,H15b,H15c)
;
_olex2_submission_special_instructions 'No special instructions were received'