Catalytic chemoselective [3+3] cycloadditions of azomethine ylides with quinone monoimides leading to the construction of a dihydrobenzoxazine scaffold
Cong-Shuai Wang; Ren-Yi Zhu; Yu-Chen Zhang; Feng Shi; Chem.Commun. 51 (2015) 11798–; doi:10.1039/C5cc03341A

data_7117466
_publ_section_title
;
 Catalytic chemoselective [3+3] cycloadditions of azomethine ylides with
 quinone monoimides leading to the construction of a dihydrobenzoxazine
 scaffold
;
_journal_name_full               Chem.Commun.
_journal_page_first              11798
_journal_paper_doi               10.1039/C5cc03341A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C27 H27 N3 O9 S'
_chemical_formula_sum            'C27 H27 N3 O9 S'
_chemical_formula_weight         569.57
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-04-16 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                86.352(4)
_cell_angle_beta                 87.532(4)
_cell_angle_gamma                77.772(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3006(6)
_cell_length_b                   9.3862(7)
_cell_length_c                   17.7170(15)
_cell_measurement_reflns_used    8381
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.30
_cell_volume                     1345.68(18)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
????
;
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.987
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20031
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.929
_diffrn_reflns_theta_min         2.224
_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    0.180
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.1631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1358 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.8792.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      .
_exptl_crystal_description       Prism
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.004(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1124P)^2^+0.7076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2277
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3607
_reflns_number_total             5190
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc03341a2.cif
_cod_data_source_block           sf141029_zry_0m
_cod_database_code               7117466
_shelxl_version_number           2014-3
_diffrn_number_total             2330
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C21(0.5) C22(0.5) H22(0.5) C23(0.5) H23(0.5) C24(0.5) C25(0.5)
 H25(0.5) C26(0.5) H26(0.5) C27(0.5) H27A(0.5) H27B(0.5) H27C(0.5) C21'(0.5)
 C22'(0.5) H22'(0.5) C23'(0.5) H23'(0.5) C24'(0.5) C25'(0.5) H25'(0.5)
 C26'(0.5) H26'(0.5) C27'(0.5) H27D(0.5) H27E(0.5) H27F(0.5)
3.a Riding coordinates:
 N2(H2), N3(H3)
3.b Ternary CH refined with riding coordinates:
 C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C22(H22),
 C23(H23), C25(H25), C26(H26), C22'(H22'), C23'(H23'), C25'(H25'), C26'(H26')
3.e Fitted hexagon refined as free rotating group:
 C21(C22,C23,C24,C25,C26), C21'(C22',C23',C24',C25',C26')
3.f Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C27'(H27D,H27E,
 H27F)
;
_shelx_res_checksum              14950
_olex2_submission_special_instructions 'No special instructions were received'