Brønsted acid-catalyzed stereoselective [4+3] cycloadditions of ortho-hydroxybenzyl alcohols with N,N'-cyclic azomethine imines.
Mei, Guang-Jian; Zhu, Zi-Qi; Zhao, Jia-Jia; Bian, Chen-Yu; Chen, Jie; Chen, Ruo-Wei; Shi, Feng; Chemical communications (Cambridge, England) 53 (2017) 2768–2771; doi:10.1039/c6cc09775h

data_7119635
_publ_section_title
;
 Br\/onsted acid-catalyzed stereoselective [4+3] cycloadditions of
 ortho-hydroxybenzyl alcohols with N,N'-cyclic azomethine imines.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2768
_journal_page_last               2771
_journal_paper_doi               10.1039/c6cc09775h
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C31 H29 N3 O2'
_chemical_formula_sum            'C31 H29 N3 O2'
_chemical_formula_weight         475.57
_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     dual
_audit_creation_date             2016-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-12-08 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.692(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6097(5)
_cell_length_b                   9.4290(6)
_cell_length_c                   27.1720(12)
_cell_measurement_reflns_used    3129
_cell_measurement_temperature    296
_cell_measurement_theta_max      66.98
_cell_measurement_theta_min      4.970
_cell_volume                     2439.9(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
????
;
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
scan:
    Number of images: 340
               Slice: -110.0000 - 60.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 45.3038
              2theta: -20.1830
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0416
_diffrn_orient_matrix_UB_12      -0.0191
_diffrn_orient_matrix_UB_13      0.0361
_diffrn_orient_matrix_UB_21      0.0301
_diffrn_orient_matrix_UB_22      -0.0492
_diffrn_orient_matrix_UB_23      0.0086
_diffrn_orient_matrix_UB_31      0.0196
_diffrn_orient_matrix_UB_32      0.0176
_diffrn_orient_matrix_UB_33      0.0318
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17788
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.496
_diffrn_reflns_theta_min         4.969
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0933 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.7469.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4470
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0725P)^2^+0.6690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3517
_reflns_number_total             4470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09775h2.cif
_cod_data_source_block           cu_dm16608_0m
_cod_depositor_comments
'Adding full bibliography for 7119634--7119635.cif.'
_cod_database_code               7119635
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.882
_diffrn_number_total             2330
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(C31) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C17(H17), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C3(H3A,H3B), C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C12(H12), C15(H15), C10(H10), C13(H13), C30(H30), C19(H19),
 C14(H14), C26(H26), C22(H22), C9(H9), C20(H20), C21(H21), C29(H29), C8(H8),
 C6(H6), C27(H27), C7(H7)
3.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'