Total Synthesis of the Resorcyclic Acid Lactone Spiroketal Citreoviranol.
Quach, Rachelle; Furkert, Daniel P.; Brimble, Margaret A.; The Journal of organic chemistry 81 (2016) 8343–8350; doi:10.1021/acs.joc.6b01503

data_4037105
_publ_section_title
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 Total Synthesis of the Resorcyclic Acid Lactone Spiroketal Citreoviranol.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8343
_journal_page_last               8350
_journal_paper_doi               10.1021/acs.joc.6b01503
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         C15H18O6
_chemical_formula_sum            'C15 H18 O6'
_chemical_formula_weight         294.11
_chemical_melting_point          72.0(10)
_chemical_name_common            citreoviranol
_chemical_name_systematic
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(2'S,4'R6'S)-spiro[6,8-dimethoxyisochroman-1-one-3,6'-2'-methyloxan-4'-ol]
;
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.992(4)
_cell_angle_beta                 92.691(4)
_cell_angle_gamma                93.826(4)
_cell_formula_units_Z            4
_cell_length_a                   7.1669(4)
_cell_length_b                   7.6027(4)
_cell_length_c                   13.8637(8)
_cell_measurement_reflns_used    '8471 / 3173 [R(int) = 0.0627]'
_cell_measurement_temperature    372(2)
_cell_measurement_theta_max      21.04
_cell_measurement_theta_min      2.70
_cell_volume                     749.80(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      372(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8471
_diffrn_reflns_theta_full        21.04
_diffrn_reflns_theta_max         21.04
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9616
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'colourless needle'
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(15)
_refine_ls_extinction_coef       0.000(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                2715
_reflns_number_total             3173
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo6b01503_si_002.cif
_cod_data_source_block           citreoviranol
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_chemical_melting_point' value '71-73' was changed to
'72.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P1
_cod_original_formula_sum        C15H18O6
_cod_database_code               4037105