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_1553509
_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
;
(3aS,6R,7S,7aR)-7-(tert-butoxy)tetrahydro-3aH-spiro
[1,6-methanopyrano[4,3-c]isoxazole-3,1'-cyclopropane]
;
_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'
_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
;
'Wed Feb 12 17:01:31 2014'
;
_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                 90.547(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.178(1)
_cell_length_b                   21.780(1)
_cell_length_c                   11.615(1)
_cell_measurement_reflns_used    8140
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.2713
_cell_measurement_theta_min      4.3104
_cell_volume                     2574.7(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET)
(compiled Sep 13 2010,14:28:38)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET)
(compiled Sep 13 2010,14:28:38)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET)
(compiled Sep 13 2010,14:28:38)
;
_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      150(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_details
;
  1 omega  -24.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  -37.0000 -150.0000 90

  2 omega   74.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000  -60.0000 43

  3 omega  -51.00  -25.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000   90.0000 26

  4 omega  -75.00  -36.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000  150.0000 39

  5 omega   36.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -77.0000 -180.0000 84

  6 omega   80.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919   45.0000 -120.0000 85

  7 omega   77.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  125.0000  -90.0000 89

  8 omega   28.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000 -120.0000 47

  9 omega -118.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -77.0000  -30.0000 102

 10 omega -118.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -77.0000 -180.0000 102

 11 omega -167.00 -133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -15.0000   60.0000 34

 12 omega   28.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000  -60.0000 49

;
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14484
_diffrn_reflns_theta_full        68.689
_diffrn_reflns_theta_max         70.399
_diffrn_reflns_theta_min         4.314
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.9485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET)
(compiled Sep 13 2010,14:28:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 2250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         7357
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0618P)^2^+0.4474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.602
_reflns_Friedel_fraction_max     0.573
_reflns_number_gt                6479
_reflns_number_total             7357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00410e2.cif
_cod_data_source_block           1121
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_moiety     '4(C13 H21 N O3)'
_cod_original_formula_sum        'C52 H84 N4 O12'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     957.23
_cod_database_code               1553509
_shelxl_version_number           2014/6
_shelx_res_checksum              40152
_shelx_hkl_checksum              44756