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_1553510
_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         'C13 H21 N O3'
_chemical_formula_sum            'C13 H21 N O3'
_chemical_formula_weight         239.31
_chemical_name_systematic
;
(4aS,7R,8S,8aR)-8-(tert-butoxy)hexahydro-1,7-methanopyrano
[4,3-b]pyridin-4(7H)-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date
;
'Tue Sep 08 12:57:44 2015'
;
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-07-28 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0780(2)
_cell_length_b                   10.2040(3)
_cell_length_c                   19.9570(6)
_cell_measurement_reflns_used    2255
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2180
_cell_measurement_theta_min      6.1820
_cell_volume                     1237.73(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_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 0.983
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
  1 omega  -75.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824   19.0000 -180.0000 105

  2 omega   73.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000 -150.0000 45

  3 omega  -69.00  -17.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  120.0000 52

  4 omega   16.00  109.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -94.0000   90.0000 93

  5 omega   28.00   74.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000 -120.0000 46

  6 omega   39.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000  -30.0000 27

  7 omega   29.00   61.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000   90.0000 32

  8 omega   25.00   58.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -150.0000 33

;
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.378
_diffrn_reflns_theta_min         4.867
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.733
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0456P)^2^+0.0713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.441
_reflns_Friedel_fraction_full    0.651
_reflns_Friedel_fraction_max     0.614
_reflns_number_gt                1675
_reflns_number_total             1946
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00410e2.cif
_cod_data_source_block           24
_cod_database_code               1553510
_shelxl_version_number           2014/6
_shelx_res_checksum              48353
_shelx_hkl_checksum              28470