ZnCl2-promoted domino reaction of 2-hydroxybenzonitriles with ketones for synthesis of 1,3-benzoxazin-4-ones
Su, Ziqi; Chai, Hongxin; Xu, Juan; Li, Jiarong; RSC Advances 11 (2021) 29906–29911; doi:10.1039/D1RA04194K

data_7243494
_publ_section_title
;
 ZnCl2-promoted domino reaction of 2-hydroxybenzonitriles with ketones for
 synthesis of 1,3-benzoxazin-4-ones
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              29906
_journal_page_last               29911
_journal_paper_doi               10.1039/D1RA04194K
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C13 H15 N O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-03-06 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.975(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8238(3)
_cell_length_b                   14.8389(7)
_cell_length_c                   10.8490(3)
_cell_measurement_reflns_used    1831
_cell_measurement_temperature    104.9
_cell_measurement_theta_max      29.5705
_cell_measurement_theta_min      3.2997
_cell_volume                     1090.41(8)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      104.9
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   12.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000   30.0000 74

  2 omega   30.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000    0.0000 56

  3 omega  -33.00   21.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000 -120.0000 54

  4 omega   51.00   81.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000  -60.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0238038000
_diffrn_orient_matrix_UB_12      -0.0408271000
_diffrn_orient_matrix_UB_13      0.0287347000
_diffrn_orient_matrix_UB_21      0.1013499000
_diffrn_orient_matrix_UB_22      -0.0069218000
_diffrn_orient_matrix_UB_23      0.0212208000
_diffrn_orient_matrix_UB_31      -0.0113643000
_diffrn_orient_matrix_UB_32      0.0238649000
_diffrn_orient_matrix_UB_33      0.0553574000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4531
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.306
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99179
_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    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0381P)^2^+0.2959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1817
_reflns_number_total             2146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra04194k2.cif
_cod_data_source_block           exp_2848
_cod_database_code               7243494
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.74
_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, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'