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_4036015
_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         'C9 H7 N O3'
_chemical_formula_sum            'C9 H7 N O3'
_chemical_formula_weight         177.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-03-26
_audit_creation_method
;
Olex2 1.2
(compiled Mar 28 2017 19:26:29 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9595(6)
_cell_length_b                   10.7062(9)
_cell_length_c                   11.3837(10)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    100
_cell_measurement_theta_max      36.246
_cell_measurement_theta_min      2.611
_cell_volume                     848.20(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         36.270
_diffrn_reflns_theta_min         2.612
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.7158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0622 before and 0.0361 after correction.
The Ratio of minimum to maximum transmission is 0.9581.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1688 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0515P)^2^+0.0605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3985
_reflns_number_total             4104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02490_si_003.cif
_cod_data_source_block           4
_cod_database_code               4036015
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C4A(H4A), C8A(H8A)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C4(H4), C3(H3)
;
_shelx_res_checksum              28009
_shelx_hkl_checksum              59012
_olex2_submission_special_instructions 'No special instructions were received'