Efficient route for the construction of polycyclic systems from bioderived HMF
Kucherov, Fedor; Galkin, Konstantin; Gordeev, Evgeniy; Ananikov, Valentine; Green Chem.  (2017) –; doi:10.1039/C7GC02211E

data_7229020
_publ_section_title
;
 Efficient route for the construction of polycyclic systems from
 bioderived HMF
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC02211E
_journal_year                    2017
_chemical_formula_moiety         'C13 H19 N O5'
_chemical_formula_sum            'C13 H19 N O5'
_chemical_formula_weight         269.29
_chemical_name_common
anti-N-methyl-4,7-bis(methoxymethyl)norcantharimide
_chemical_name_systematic
anti-4,7-bis(methoxymethyl)-2-methylhexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2017-06-22 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.16(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.389(2)
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_cell_length_c                   8.4911(17)
_cell_measurement_reflns_used    500
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      1.8
_cell_volume                     1312.7(5)
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_data_reduction        iMosflm
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_unetI/netI     0.1381
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10961
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        35.587
_diffrn_reflns_theta_max         38.407
_diffrn_reflns_theta_min         1.742
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.084(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0878
_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^)+(0.0548P)^2^+0.7069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1924
_reflns_number_total             2578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc02211e2.cif
_cod_data_source_block           Ted1962
_cod_database_code               7229020
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014/6
_shelx_res_checksum              45440