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_4027611
_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_moiety         'C15 H20 O7'
_chemical_formula_sum            'C15 H20 O7'
_chemical_formula_weight         312.31
_chemical_name_systematic        ?
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.085(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.2917(10)
_cell_length_b                   18.442(2)
_cell_length_c                   19.455(2)
_cell_measurement_reflns_used    7724
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.11305
_cell_measurement_theta_min      2.2086
_cell_volume                     3325.3(6)
_computing_cell_refinement       'APEX2 (Bruker, 2011); SAINT (Bruker, 2009)'
_computing_data_collection       'GIS (Bruker)'
_computing_data_reduction
;
SAINT (Bruker, 2009); XPREP (Sheldrick,
 2008).
;
_computing_molecular_graphics    'APEX2 (Bruker, 2011)'
_computing_publication_material  'APEX2 (Bruker, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_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_source         'XOS X-beam microfocus source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18652
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0827P)^2^+2.4652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                2354
_reflns_number_total             2951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3017617_si_002_1.cif
_cod_data_source_block           Allyl_Ester_20
_cod_original_cell_volume        3325.4(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4027611