Brønsted Acid-Promoted [3 + 3] Cycloaddition of Azomethine Ylides with Quinone Monoimine: A Practical Method towards Dihydrobenzoxazine Derivatives
Guo, Hongchao; Wu, Yang; Liu, Honglei; Zhang, Lei; Xiao, Yumei; Qiao, Guanyu; Sun, Zhanhu; RSC Adv.  (2015) –; doi:10.1039/C5RA12401H

data_7222400
_publ_section_title
;
 Br\/onsted Acid-Promoted [3 + 3] Cycloaddition of Azomethine Ylides with
 Quinone Monoimine: A Practical Method towards Dihydrobenzoxazine
 Derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA12401H
_journal_year                    2015
_chemical_formula_moiety         'C27 H28 N2 O7 S'
_chemical_formula_sum            'C27 H28 N2 O7 S'
_chemical_formula_weight         524.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-06-23 deposited with the CCDC.
2015-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.485(4)
_cell_length_b                   14.715(3)
_cell_length_c                   20.774(4)
_cell_measurement_reflns_used    7638
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4819
_cell_measurement_theta_min      2.2135
_cell_volume                     5437(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0379
_diffrn_orient_matrix_UB_12      -0.0406
_diffrn_orient_matrix_UB_13      0.0088
_diffrn_orient_matrix_UB_21      -0.0501
_diffrn_orient_matrix_UB_22      0.0441
_diffrn_orient_matrix_UB_23      -0.0127
_diffrn_orient_matrix_UB_31      -0.0076
_diffrn_orient_matrix_UB_32      -0.0214
_diffrn_orient_matrix_UB_33      -0.0446
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33938
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.038
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8808
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.243
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0691
_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^)+(0.0754P)^2^+8.1443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6095
_reflns_number_total             6213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra12401h2.cif
_cod_data_source_block           sa3731
_cod_database_code               7222400
_shelxl_version_number           2013-4
_diffrn_number_total             6455
_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.a Riding coordinates:
 N1(H1), N2(H2)
2.b Ternary CH refined with riding coordinates:
 C15(H15)
2.c Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C26(H26A,H26B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              88388
_shelx_hkl_checksum              14494