Configuration-guided reactions: the case of highly decorated spiro[cyclopropane-1,2′(3′H)-pyrrolo[1,2-b]isoxazole] derivatives en route to polyhydroxyindolizidines
Cordero, F. M.; Vurchio, C.; Faggi, C.; Brandi, A.; Organic Chemistry Frontiers 3 (2016) 1651–; doi:10.1039/C6QO00410E

data_1553507
_publ_section_title
;
 Configuration-guided reactions: the case of highly decorated
 spiro[cyclopropane-1,2&#x2032;(3&#x2032;H)-pyrrolo[1,2-b]isoxazole]
 derivatives en route to polyhydroxyindolizidines
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1651
_journal_paper_doi               10.1039/C6QO00410E
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H31 N O4'
_chemical_formula_sum            'C17 H31 N O4'
_chemical_formula_weight         313.43
_chemical_name_systematic
((3'S,3a'R,4'R,5'R)-4',5'-di-tert-butoxytetrahydro-3'H-spiro[cyclopropane-1,2'-pyrrolo[1,2-b]isoxazol]-3'-yl)methanol
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date
;
'Tue Oct 14 18:41:24 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_audit_update_record
;
2016-07-28 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.6430(10)
_cell_length_b                   16.1440(10)
_cell_length_c                   6.6010(10)
_cell_measurement_reflns_used    2322
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.5550
_cell_measurement_theta_min      4.9960
_cell_volume                     1880.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
  1 omega   76.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000    0.0000 34

  2 omega  -16.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  -57.0000  -60.0000 81

  3 omega  -92.00  -45.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000   30.0000 47

  4 omega  -64.00  -27.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000   60.0000 37

  5 omega   32.00   57.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -180.0000 25

  6 omega   24.00   49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -150.0000 25

  7 omega   35.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000   90.0000 33

  8 omega   17.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -94.0000 -150.0000 89

  9 omega -122.00  -47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -19.0000 -120.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5913
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.844
_diffrn_reflns_theta_min         5.013
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.97530
_exptl_absorpt_correction_T_min  0.96019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0428P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.532
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.701
_reflns_number_gt                2442
_reflns_number_total             3079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00410e2.cif
_cod_data_source_block           exp_1273
_cod_database_code               1553507
_shelxl_version_number           2014/6
_shelx_res_checksum              10932
_shelx_hkl_checksum              36074