Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction
Hong, Longcheng; Ahles, Sebastian; Strauss, Marcel A.; Logemann, Christian; Wegner, Hermann A.; Organic Chemistry Frontiers 4 (2017) 871–; doi:10.1039/C7QO00172J

data_1553763
_publ_section_title
;
 Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid
 catalysed inverse electron-demand Diels--Alder (IEDDA) reaction
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              871
_journal_paper_doi               10.1039/C7QO00172J
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C14 H10 N2 O2, H2 O'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-02-27 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.777(2)
_cell_angle_beta                 92.263(2)
_cell_angle_gamma                114.9680(10)
_cell_formula_units_Z            2
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_cell_length_b                   7.8866(3)
_cell_length_c                   11.4159(5)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      45.35
_cell_measurement_theta_min      2.86
_cell_volume                     577.75(4)
_computing_cell_refinement       'APEX3 v2014.5-2'
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_computing_data_reduction        'APEX3 v2014.5-2'
_computing_molecular_graphics    'Diamond 4.3'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
'BRUKER D8 Venture, Bruker Photon 100 CMOS detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.999
_diffrn_reflns_theta_min         2.856
_diffrn_source                   'ImuS microfocus source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker, Madison, 2014'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0691P)^2^+0.0836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4143
_reflns_number_total             5048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00172j2.cif
_cod_data_source_block           mo_hol86_0m
_cod_database_code               1553763
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2013-4
_shelx_res_checksum              74570
_shelx_hkl_checksum              75624