Syntheses of Papyracillic Acids: Application of the Tandem Chain Extension-Acylation Reaction
Jennifer R. Mazzone; Charles K. Zercher; Journal of Organic Chemistry 77 (2012) 9171–9178; doi:10.1021/jo3017617

data_4027613
_publ_contact_author_address
;Department of Chemistry
23 Academic Way
University of New Hampshire
Durham, NH 03824
;
_publ_contact_author_email       chuck.zercher@unh.edu
_publ_contact_author_name        'Charles K. Zercher'
_publ_section_title
;
 Syntheses of Papyracillic Acids: Application of the Tandem Chain
 Extension-Acylation Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9171
_journal_page_last               9178
_journal_paper_doi               10.1021/jo3017617
_journal_volume                  77
_journal_year                    2012
_chemical_formula_iupac          'C13 H18 O7'
_chemical_formula_moiety         'C13 H18 O7'
_chemical_formula_sum            'C13 H18 O7'
_chemical_formula_weight         286.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.191(5)
_cell_angle_beta                 116.979(5)
_cell_angle_gamma                111.629(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2928(13)
_cell_length_b                   9.4950(15)
_cell_length_c                   10.1967(17)
_cell_measurement_reflns_used    2210
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      22.7433
_cell_measurement_theta_min      2.3135
_cell_volume                     722.1(2)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'GIS (Bruker, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'APEX2 (Bruker AXS, 2009)'
_computing_publication_material  'APEX2 (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART X2S Benchtop Diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7167
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.74
_diffrn_source                   'XOS X-beam microfocus source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.0224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                1836
_reflns_number_total             2518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3017617_si_002_3.cif
_cod_data_source_block           Ketal_16a
_cod_original_cell_volume        722.06(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4027613