Crystal structure and absolute configuration of (4<i>S</i>,5<i>R</i>,6<i>S</i>)-4,5,6-trihydroxy-3-methylcyclohex-2-enone (gabosine H)
Tibhe, Gaurao D.; Macías, Mario A.; Pandolfi, Enrique; Schapiro, Valeria; Suescun, Leopoldo; Acta Crystallographica Section E 73 (2017) 606–609; doi:10.1107/S2056989017004509

data_2242181
_publ_section_title
;
 Crystal structure and absolute configuration of
 (4<i>S</i>,5<i>R</i>,6<i>S</i>)-4,5,6-trihydroxy-3-methylcyclohex-2-enone
 (gabosine H)
;
_journal_coeditor_code           RZ5209
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              606
_journal_page_last               609
_journal_paper_doi               10.1107/S2056989017004509
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C7 H10 O4'
_chemical_formula_moiety         'C7 H10 O4'
_chemical_formula_sum            'C7 H10 O4'
_chemical_formula_weight         158.15
_chemical_name_systematic
;
(4<i>S</i>,5<i>R</i>,6<i>S</i>)-4,5,6-Trihydroxy-3-methylcyclohex-2-enone
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90.9770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4143(2)
_cell_length_b                   5.4176(2)
_cell_length_c                   11.9200(5)
_cell_measurement_reflns_used    9784
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      78.8035
_cell_measurement_theta_min      3.7085
_cell_volume                     349.59(2)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0464
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12187
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.125
_diffrn_reflns_theta_min         3.709
_exptl_absorpt_coefficient_mu    1.059
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.5882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.342
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.182
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 639 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.09(11)
_refine_ls_extinction_coef       0.161(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1492
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0546P)^2^+0.0518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                1472
_reflns_number_total             1492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rz5209sup1.cif
_cod_data_source_block           I
_cod_database_code               2242181
_cod_database_fobs_code          2242181
_shelx_estimated_absorpt_t_min   0.693
_shelx_estimated_absorpt_t_max   0.898
_shelx_hkl_checksum              86794
_shelx_res_checksum              32779
_shelxl_version_number           2.014