Skeletal diversity via cationic rearrangements of substituted dihydropyrans.
Medeiros, Matthew R.; Narayan, Radha S.; McDougal, Nolan T.; Schaus, Scott E.; Porco, Jr, John A; Organic letters 12 (2010) 3222–3225; doi:10.1021/ol101144k

data_1503060
_publ_contact_author             'John A. Porco, Jr.'
_publ_section_title
;
 Skeletal diversity via cationic rearrangements of substituted
 dihydropyrans.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3222
_journal_page_last               3225
_journal_paper_doi               10.1021/ol101144k
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H20 N4 O7'
_chemical_formula_sum            'C16 H20 N4 O7'
_chemical_formula_weight         380.36
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-03-31 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.610(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.757(8)
_cell_length_b                   29.99(2)
_cell_length_c                   11.970(9)
_cell_measurement_reflns_used    9806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.4696
_cell_measurement_theta_min      4.0201
_cell_volume                     3463(4)
_computing_cell_refinement       'Apex2 (Bruker, 2006)'
_computing_data_collection       'Apex2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\w & \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26648
_diffrn_reflns_theta_full        64.84
_diffrn_reflns_theta_max         64.84
_diffrn_reflns_theta_min         3.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  0.9513
_exptl_absorpt_correction_T_min  0.8340
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Apex2 (Bruker, 2006)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     982
_refine_ls_number_reflns         10178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.5375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                10045
_reflns_number_total             10178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101144k_si_002.cif
_cod_data_source_block           compound_SI_09
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1503060