π-Facial selectivity in the Diels-Alder reaction of glucosamine-based chiral furans and maleimides.
van der Loo, Cornelis H. M.; Schim van der Loeff, Rutger; Martín, Avelino; Gomez-Sal, Pilar; Borst, Mark L. G.; Pouwer, Kees; Minnaard, Adriaan J.; Organic & biomolecular chemistry 21 (2023) 1888–1894; doi:10.1039/d2ob02221d

data_7159055
_publ_section_title
;
 &#x3c0;-Facial selectivity in the Diels-Alder reaction of
 glucosamine-based chiral furans and maleimides.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1888
_journal_page_last               1894
_journal_paper_doi               10.1039/d2ob02221d
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C31 H28 N2 O8'
_chemical_formula_sum            'C31 H28 N2 O8'
_chemical_formula_weight         556.55
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-09-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-30 deposited with the CCDC.	2022-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.886(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4038(19)
_cell_length_b                   6.0006(9)
_cell_length_c                   18.430(3)
_cell_measurement_reflns_used    2053
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      20.907
_cell_measurement_theta_min      2.459
_cell_volume                     1319.4(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'Apex3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type
;
Bruker AXS D8 Venture diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1446
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35365
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         3.403
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'INCOATEC I\ms 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1366 before and 0.0687 after correction.
The Ratio of minimum to maximum transmission is 0.8534.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1154 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         4636
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0239P)^2^+0.3013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3286
_reflns_number_total             4636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02221d2.cif
_cod_data_source_block           pgsk_0m_a
_cod_depositor_comments          'Adding full bibliography for 7159055.cif.'
_cod_original_cell_volume        1319.3(3)
_cod_database_code               7159055
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C31(H31), C32(H32),
 C33(H33), C34(H34), C35(H35), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43)
;
_shelx_res_checksum              54219
_olex2_submission_special_instructions 'No special instructions were received'