Lewis Acid Catalyzed Conversion of 5-Hydroxymethylfurfural to 1,2,4-Benzenetriol, an Overlooked Biobased Compound.
Kumalaputri, Angela J.; Randolph, Caelan; Otten, Edwin; Heeres, Hero J.; Deuss, Peter J.; ACS sustainable chemistry & engineering 6 (2018) 3419–3425; doi:10.1021/acssuschemeng.7b03648

data_4517025
_publ_section_title
;
 Lewis Acid Catalyzed Conversion of 5-Hydroxymethylfurfural to
 1,2,4-Benzenetriol, an Overlooked Biobased Compound.
;
_journal_issue                   3
_journal_name_full               'ACS sustainable chemistry &amp; engineering'
_journal_page_first              3419
_journal_page_last               3425
_journal_paper_doi               10.1021/acssuschemeng.7b03648
_journal_volume                  6
_journal_year                    2018
_chemical_formula_sum            'C12 H14 O8'
_chemical_formula_weight         286.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.163(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8541(4)
_cell_length_b                   6.0625(5)
_cell_length_c                   24.554(2)
_cell_measurement_reflns_used    5785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      3.33
_cell_volume                     572.20(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9007
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.328
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1168
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+2.9567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1076
_reflns_number_total             1168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc7b03648_si_001.cif
_cod_data_source_block           mo_molan465_0m_a
_cod_original_cell_volume        572.21(9)
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               4517025
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              90867
_shelx_hkl_checksum              61326