Enantioselective transformations of 5-hydroxymethylfurfural <i>via</i> catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides.
Cristóbal, Christian; Corral, César; Carretero, Juan C.; Ribagorda, Maria; Adrio, Javier; Chemical communications (Cambridge, England) 59 (2023) 4336–4339; doi:10.1039/d3cc00499f

data_7131445
_publ_section_title
;
 Enantioselective transformations of 5-hydroxymethylfurfural <i>via</i>
 catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides.
;
_journal_issue                   29
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4336
_journal_page_last               4339
_journal_paper_doi               10.1039/d3cc00499f
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H20 N2 O6'
_chemical_formula_weight         384.38
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2dm7pz
_audit_update_record
;
2022-11-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5537(2)
_cell_length_b                   14.9106(4)
_cell_length_c                   18.4935(4)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      74.5204
_cell_measurement_theta_min      3.8081
_cell_volume                     1807.18(8)
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Cu-IMS3.0'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21276
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.81
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec Cu-IMS3.0'
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.144
_refine_ls_abs_structure_details
;

Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0388P)^2^+0.4017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                3184
_reflns_number_total             3302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00499f2.cif
_cod_data_source_block           03457_Cu
_cod_depositor_comments          'Adding full bibliography for 7131445.cif.'
_cod_database_code               7131445
_shelx_res_checksum              9078
_shelx_hkl_checksum              92168