Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives.
Veits, Gesine K.; Wenz, Donald R.; Palmer, Leoni I.; St Amant, André H; Hein, Jason E.; Read de Alaniz, Javier; Organic & biomolecular chemistry 13 (2015) 8465–8469; doi:10.1039/c5ob00944h

data_7154583
_publ_section_title
;
 Cascade rearrangement of furylcarbinols with hydroxylamines: practical
 access to densely functionalized cyclopentane derivatives.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8465
_journal_page_last               8469
_journal_paper_doi               10.1039/c5ob00944h
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C25 H25 N O2'
_chemical_formula_weight         371.46
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-02-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.174(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6814(15)
_cell_length_b                   5.7264(6)
_cell_length_c                   27.718(3)
_cell_measurement_temperature    101(2)
_cell_volume                     1987.1(4)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.1315
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8868
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.740
_diffrn_reflns_theta_min         0.744
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6068
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.3226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_full    0.728
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                3916
_reflns_number_total             6068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00944h2.cif
_cod_data_source_block           d02062014_0m
_cod_depositor_comments          'Adding full bibliography for 7154583.cif.'
_cod_database_code               7154583
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-3
_shelx_res_checksum              1689