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_1553511
_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         'C26 H42 N2 O6'
_chemical_formula_sum            'C26 H42 N2 O6'
_chemical_formula_weight         478.61
_chemical_name_systematic
;
(3R,4S,4aR,8aS,11R,12S,12aR,16aS)-4,12-di-tert-butoxydodecahydro-3,5:11,13-
dimethanodipyrano[4,3-b:4',3'-h][1,7]diazacyclododecine-8,16(3H,11H)-dione
;
_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
;
'Tue May 10 12:33:38 2016'
;
_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                 100.170(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2520(10)
_cell_length_b                   25.5700(10)
_cell_length_c                   14.4650(10)
_cell_measurement_reflns_used    5427
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.5950
_cell_measurement_theta_min      4.6420
_cell_volume                     2640.2(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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 0.994
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
  1 omega -125.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.1574  -99.0000  -60.0000 35

  2 omega  -22.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.1574  -37.0000  120.0000 87

  3 omega   67.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.1574   37.0000 -120.0000 46

  4 omega  -69.00  -35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  -30.0000 34

  5 omega  -53.00  -26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   77.0000 -150.0000 27

  6 omega  -88.00  -59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   77.0000 -150.0000 29

  7 omega  -64.00  -29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000   90.0000 35

  8 omega   37.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000   30.0000 34

  9 omega   40.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -94.0000   30.0000 69

 10 omega   67.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   15.0000  -30.0000 100

 11 omega   28.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -30.0000  150.0000 27

 12 omega   55.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000 -125.0000  -60.0000 58

 13 omega   38.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -30.0000  120.0000 29

;
_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  0.0421
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11770
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.537
_diffrn_reflns_theta_min         4.648
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.25(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         7615
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0694P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.492
_reflns_Friedel_fraction_full    0.532
_reflns_Friedel_fraction_max     0.492
_reflns_number_gt                6330
_reflns_number_total             7615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00410e2.cif
_cod_data_source_block           94
_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     '2(C26 H42 N2 O6)'
_cod_original_formula_sum        'C52 H84 N4 O12'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     957.23
_cod_database_code               1553511
_shelxl_version_number           2014/6
_shelx_res_checksum              5644
_shelx_hkl_checksum              58637