Synthesis and crystal structure of (2<i>S</i>,4a<i>R</i>,8a<i>R</i>)-6-oxo-2,4a,6,8a-tetrahydropyrano[3,2-<i>b</i>]pyran-2-carboxamide
Greene, John; Kopplin, Noa; Roireau, Jack; Bezpalko, Mark; Kassel, Scott; Giuliano, Michael W.; Giuliano, Robert; Acta Crystallographica Section E 76 (2020) 761–764; doi:10.1107/S2056989020001292

data_2243379
_publ_section_title
;
 Synthesis and crystal structure of
 (2<i>S</i>,4a<i>R</i>,8a<i>R</i>)-6-oxo-2,4a,6,8a-tetrahydropyrano[3,2-<i>b</i>]pyran-2-carboxamide
;
_journal_coeditor_code           ZL4038
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              761
_journal_page_last               764
_journal_paper_doi               10.1107/S2056989020001292
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_iupac          'C9 H9 N O4'
_chemical_formula_moiety         'C9 H9 N O4'
_chemical_formula_sum            'C9 H9 N O4'
_chemical_formula_weight         195.17
_chemical_name_systematic
(2<i>S</i>,4a<i>R</i>,8a<i>R</i>)-6-Oxo-2,4a,6,8a-tetrahydropyrano[3,2-<i>b</i>]pyran-2-carboxamide
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.92790(10)
_cell_length_b                   10.6350(3)
_cell_length_c                   15.8788(4)
_cell_measurement_reflns_used    8408
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.17
_cell_measurement_theta_min      2.30
_cell_volume                     832.18(4)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al</i>., 2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al</i>., 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al</i>., 1994)
;
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0314
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14252
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.198
_diffrn_reflns_theta_min         2.305
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al</i>., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.201
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 928 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0446P)^2^+0.2050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                2366
_reflns_number_total             2461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl4038sup1.cif
_cod_data_source_block           I
_cod_database_code               2243379
_cod_database_fobs_code          2243379
_shelx_hkl_checksum              97939
_shelx_res_checksum              91127