Synthesis, crystal structure and absolute configuration of (3aS,4R,5S,7aR)-7-(but-3-en-1-yn-1-yl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-2H-1,3-benzodioxole-4,5-diol
Peixoto de Abreu Lima, Alejandro; Pandolfi, Enrique; Schapiro, Valeria; Suescun, Leopoldo; Acta Crystallographica Section E Crystallographic Communications 80 (2024) 1165–1169; doi:10.1107/S2056989024009733

data_2023287
_publ_section_title
;
 Synthesis, crystal structure and absolute configuration of
 (3aS,4R,5S,7aR)-7-(but-3-en-1-yn-1-yl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-2H-1,3-benzodioxole-4,5-diol
;
_journal_coeditor_code           EE2008
_journal_issue                   11
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              1165
_journal_page_last               1169
_journal_paper_doi               10.1107/S2056989024009733
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_iupac          'C13 H16 O4'
_chemical_formula_moiety         'C13 H16 O4'
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_chemical_name_common
(1<i>S</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-5-(But-3-en-1-ynyl)-1,2-dihydroxy-3,4-isopropylidenedioxocycle-5-hexene
_chemical_name_systematic
(3a<i>S</i>,4<i>R</i>,5<i>S</i>,7a<i>R</i>)-7-(But-3-en-1-yn-1-yl)-2,2-dimethyl-3a,4,5,7a-tetrahydro-2<i>H</i>-1,3-benzodioxole-4,5-diol
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 109.652(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4126(13)
_cell_length_b                   5.0996(4)
_cell_length_c                   14.9856(11)
_cell_measurement_reflns_used    7392
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      77.75
_cell_measurement_theta_min      5.225
_cell_volume                     1253.17(16)
_computing_cell_refinement
;
SAINT V8.38A (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT V8.38A (Bruker, 2018)
;
_computing_molecular_graphics
;
<i>ShelXle</i> (H\"ubschle et al., 2011)
;
_computing_publication_material
;
<i>ShelXle</i> (H\"ubschle et al., 2011)
;
_computing_structure_refinement
;
<i>SHELXL2019/2</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>olex2.solve</i> 1.5 (Bourhis <i>et al.</i>,  2015, Dolomanov <i>et
al.</i>,  2009)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       '\j and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10420
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         81.635
_diffrn_reflns_theta_min         5.249
_diffrn_source                   'Cu Incoatec microsource'
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6456
_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    1.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.206
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 752 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0804
_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^)+(0.1316P)^2^+0.6357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2344
_refine_ls_wR_factor_ref         0.2483
_reflns_number_gt                2138
_reflns_number_total             2628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ee2008.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023287.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2023287
_shelx_estimated_absorpt_t_min   0.760
_shelx_estimated_absorpt_t_max   0.914
_shelx_hkl_checksum              67074
_shelx_res_checksum              31197