Synthesis of imidazo[1,2-a][1,3,5]triazines by NBS-mediated coupling of 2-amino-1,3,5-triazines with 1,3-dicarbonyl compounds
Pan, Zexi; Song, Chan; Zhou, Wei; Cui, Dong-Mei; Zhang, Chen; New Journal of Chemistry 44 (2020) 6182–6185; doi:10.1039/C9NJ05794C

data_7059443
_publ_section_title
;
 Synthesis of imidazo[1,2-a][1,3,5]triazines by NBS-mediated coupling of
 2-amino-1,3,5-triazines with 1,3-dicarbonyl compounds
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6182
_journal_page_last               6185
_journal_paper_doi               10.1039/C9NJ05794C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C16 H17 N5 O2'
_chemical_formula_sum            'C16 H17 N5 O2'
_chemical_formula_weight         311.34
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-01
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
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_audit_update_record
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2019-11-25 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                109.818(7)
_cell_angle_beta                 97.305(6)
_cell_angle_gamma                100.110(6)
_cell_formula_units_Z            2
_cell_length_a                   7.1753(5)
_cell_length_b                   10.1901(9)
_cell_length_c                   11.0558(9)
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.3363
_cell_measurement_theta_min      2.9382
_cell_volume                     733.32(11)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -79.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -30.0000 88

  2 omega  -38.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000  -90.0000 97

  3 omega  -74.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000  150.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0264107000
_diffrn_orient_matrix_UB_12      -0.0450985000
_diffrn_orient_matrix_UB_13      0.0348096000
_diffrn_orient_matrix_UB_21      -0.0332988000
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_diffrn_orient_matrix_UB_23      0.0441742000
_diffrn_orient_matrix_UB_31      -0.0932916000
_diffrn_orient_matrix_UB_32      -0.0265533000
_diffrn_orient_matrix_UB_33      -0.0410421000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.944
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85849
_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    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.285
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_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     211
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0597P)^2^+0.1632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2027
_reflns_number_total             2690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj05794c2.cif
_cod_data_source_block           171130_sc171128
_cod_depositor_comments
;Adding full bibliography for 7059443.cif.

 Adding full bibliography for 7059443.cif.
;
_cod_database_code               7059443
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 99.67
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              75454
_olex2_submission_special_instructions 'No special instructions were received'