Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived <i>N</i>-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid.
Zou, Ning; Wu, Yu-Zheng; Shang, Zi-Wei; Cao, Yu-Wei; Liao, Li-Min; Wei, Cui; Mo, Dong-Liang; Zhou, Wen-Jun; Organic & biomolecular chemistry 22 (2024) 9047–9052; doi:10.1039/d4ob01365d

data_7160181
_publ_section_title
;
 Asymmetric [3 + 3] cycloaddition of cinnamaldehyde-derived <i>N</i>-aryl
 nitrones with 2-indolemethanols enabled by chiral phosphoric acid.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9047
_journal_page_last               9052
_journal_paper_doi               10.1039/d4ob01365d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C36 H28 N2 O'
_chemical_formula_sum            'C36 H28 N2 O'
_chemical_formula_weight         504.60
_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   geom
_audit_creation_date             2024-07-19
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-07-20 deposited with the CCDC.	2024-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                69.772(4)
_cell_angle_beta                 69.194(5)
_cell_angle_gamma                76.134(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2072(6)
_cell_length_b                   10.9695(5)
_cell_length_c                   13.5745(6)
_cell_measurement_reflns_used    11114
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7850
_cell_measurement_theta_min      3.6150
_cell_volume                     1321.28(13)
_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, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17613
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.379
_diffrn_reflns_theta_min         3.636
_exptl_absorpt_coefficient_mu    0.591
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0464P)^2^+0.2175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4723
_reflns_number_total             5321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01365d2.cif
_cod_data_source_block           20211206-mdl-wyz-1
_cod_depositor_comments          'Adding full bibliography for 7160181.cif.'
_cod_database_code               7160181
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C2(H2)
1.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C27(H27), C32(H32), C31(H31), C33(H33), C15(H15), C18(H18), C11(H11),
 C16(H16), C19(H19), C25(H25), C14(H14), C24(H24), C17(H17), C30(H30), C13(H13),
  C39(H39), C29(H29), C21(H21), C23(H23), C28(H28), C12(H12), C22(H22),
 C35(H35), C37(H37), C38(H38), C36(H36)
;
_shelx_res_checksum              80550
_olex2_submission_special_instructions 'No special instructions were received'