Efficient synthesis of fully renewable, furfural-derived building blocks <i>via</i> formal Diels-Alder cycloaddition of atypical addends.
Cioc, Răzvan C; Harsevoort, Eva; Lutz, Martin; Bruijnincx, Pieter C. A.; Green chemistry : an international journal and green chemistry resource : GC 25 (2023) 9689–9694; doi:10.1039/d3gc02357e

data_7247295
_publ_section_title
;
 Efficient synthesis of fully renewable, furfural-derived building blocks
 <i>via</i> formal Diels-Alder cycloaddition of atypical addends.
;
_journal_issue                   23
_journal_name_full
'Green chemistry : an international journal and green chemistry resource : GC'
_journal_page_first              9689
_journal_page_last               9694
_journal_paper_doi               10.1039/d3gc02357e
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C11 H13 Br O3'
_chemical_formula_sum            'C11 H13 Br O3'
_chemical_formula_weight         273.12
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-06 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                107.710(4)
_cell_angle_beta                 98.149(4)
_cell_angle_gamma                105.204(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8474(4)
_cell_length_b                   9.4994(5)
_cell_length_c                   11.3086(6)
_cell_measurement_reflns_used    8217
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      1.94
_cell_volume                     560.43(6)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex3
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9421
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.948
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.652
_exptl_absorpt_correction_T_max  0.7186
_exptl_absorpt_correction_T_min  0.3673
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.1683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0622
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2363
_reflns_number_total             2576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02357e2.cif
_cod_data_source_block           l1229a
_cod_depositor_comments
'Adding full bibliography for 7247295--7247296.cif.'
_cod_original_cell_volume        560.42(6)
_cod_database_code               7247295
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              35327
_shelx_hkl_checksum              87273