One Base for Two Shots: Metal-Free Substituent-Controlled Synthesis of Two Kinds of Oxadiazine Derivatives from Alkynylbenziodoxolones and Amidoximes.
Li, Ming; Li, Wei; Lin, Cheng-Dong; Wang, Jia-Hui; Wen, Li-Rong; The Journal of organic chemistry 84 (2019) 6904–6915; doi:10.1021/acs.joc.9b00659

data_4034638
_publ_section_title
;
 One Base for Two Shots: Metal-Free Substituent-Controlled Synthesis of
 Two Kinds of Oxadiazine Derivatives from Alkynylbenziodoxolones and
 Amidoximes.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6904
_journal_page_last               6915
_journal_paper_doi               10.1021/acs.joc.9b00659
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C30 H22 Cl2 N4 O2'
_chemical_formula_sum            'C30 H22 Cl2 N4 O2'
_chemical_formula_weight         541.41
_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'
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_atom_sites_solution_primary     dual
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_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_audit_update_record
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????
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_cell_length_c                   12.860(2)
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_cell_measurement_temperature    173(2)
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_cell_measurement_theta_min      1.5937
_cell_volume                     2583.9(7)
_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., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20237
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         1.930
_diffrn_source                   'Rotating Anode'
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_exptl_absorpt_correction_T_min  0.87263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
_exptl_crystal_F_000             1120
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_exptl_crystal_size_min          0.056
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_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0318P)^2^+1.5125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5481
_reflns_number_total             5901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00659_si_001.cif
_cod_data_source_block           mx6886a
_cod_database_code               4034638
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.941
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C29(H29), C30(H30)
;
_shelx_res_checksum              68237
_shelx_hkl_checksum              76872
_olex2_submission_special_instructions 'No special instructions were received'