Synthesis and Biological Evaluation of 6-[(1 R)-1-Hydroxyethyl]-2,4a( R),6( S),8a( R)-tetrahydropyrano-[3,2- b]-pyran-2-one and Structural Analogues of the Putative Structure of Diplopyrone.
Lazzara, Nicholas C.; Rosano, Robert J.; Vagadia, Purav P.; Giovine, Matthew T.; Bezpalko, Mark W.; Piro, Nicholas A.; Kassel, Wm Scott; Boyko, Walter J.; Zubris, Deanna L.; Schrader, Kevin K.; Wedge, David E.; Duke, Stephen O.; Giuliano, Robert M.; The Journal of organic chemistry 84 (2019) 666–678; doi:10.1021/acs.joc.8b02490

data_4036016
_publ_section_title
;
 Synthesis and Biological Evaluation of 6-[(1 R)-1-Hydroxyethyl]-2,4a(
 R),6( S),8a( R)-tetrahydropyrano-[3,2- b]-pyran-2-one and Structural
 Analogues of the Putative Structure of Diplopyrone.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              666
_journal_page_last               678
_journal_paper_doi               10.1021/acs.joc.8b02490
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C12 H14 O5'
_chemical_formula_sum            'C12 H14 O5'
_chemical_formula_weight         238.23
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.125(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7672(2)
_cell_length_b                   11.7433(4)
_cell_length_c                   7.7423(3)
_cell_measurement_reflns_used    4391
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.90
_cell_measurement_theta_min      3.25
_cell_volume                     569.97(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8107
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.040
_diffrn_reflns_theta_min         2.840
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0514 before and 0.0387 after correction. 
The Ratio of minimum to maximum transmission is 0.8310. 
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       Prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.1267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.855
_reflns_number_gt                2906
_reflns_number_total             3106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02490_si_002.cif
_cod_data_source_block           3
_cod_database_code               4036016
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4A(H4A), C6(H6), C8A(H8A), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              93510
_shelx_hkl_checksum              67991
_olex2_submission_special_instructions 'No special instructions were received'