Base-Mediated Diastereoselective [4+3] Annulation of in situ Generated ortho-Quinone Methides with C,N-Cyclic Azomethine Imines
Xu, Jianfeng; Yuan, Shiru; Peng, Jingyi; Miao, Maozhong; Chen, Zhengkai; Ren, Hongjun; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01783A

data_7155851
_publ_section_title
;
 Base-Mediated Diastereoselective [4+3] Annulation of in situ Generated
 ortho-Quinone Methides with C,N-Cyclic Azomethine Imines
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01783A
_journal_year                    2017
_chemical_formula_moiety         'C29 H23 Cl N2 O2'
_chemical_formula_sum            'C29 H23 Cl N2 O2'
_chemical_formula_weight         466.94
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-31 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                92.638(7)
_cell_angle_beta                 99.870(8)
_cell_angle_gamma                105.055(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8691(9)
_cell_length_b                   11.1836(9)
_cell_length_c                   12.6245(12)
_cell_measurement_reflns_used    1927
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2352
_cell_measurement_theta_min      3.2842
_cell_volume                     1185.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -69.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000   30.0000 90

  2 omega  -16.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   52.0000  -55.0000 102

  3 omega  -64.00   20.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000  150.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0012466000
_diffrn_orient_matrix_UB_12      -0.0568412000
_diffrn_orient_matrix_UB_13      0.0223719000
_diffrn_orient_matrix_UB_21      -0.0787425000
_diffrn_orient_matrix_UB_22      -0.0274758000
_diffrn_orient_matrix_UB_23      -0.0283783000
_diffrn_orient_matrix_UB_31      0.0302303000
_diffrn_orient_matrix_UB_32      -0.0191591000
_diffrn_orient_matrix_UB_33      -0.0444537000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7390
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.291
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0846P)^2^+0.1198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2935
_reflns_number_total             4314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01783a2.cif
_cod_data_source_block           170426_ysr_4_44
_cod_database_code               7155851
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 cl1'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.923
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29)
;
_shelx_res_checksum              10551
_olex2_submission_special_instructions 'No special instructions were received'