Copper-Catalyzed Tandem Reactions of 2-Amine-[1,3,5]triazines with Nitriles.
Zhang, Li-Yu; Zhang, Chen; Wang, Tao; Shi, Yu-Long; Ban, Meng-Tao; Cui, Dong-Mei; The Journal of organic chemistry 84 (2019) 536–543; doi:10.1021/acs.joc.8b02150

data_4036013
_publ_section_title
;
 Copper-Catalyzed Tandem Reactions of 2-Amine-[1,3,5]triazines with
 Nitriles.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              536
_journal_page_last               543
_journal_paper_doi               10.1021/acs.joc.8b02150
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H16 N6'
_chemical_formula_sum            'C14 H16 N6'
_chemical_formula_weight         268.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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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_cell_angle_alpha                90
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_cell_length_a                   11.6358(11)
_cell_length_b                   15.0363(15)
_cell_length_c                   7.9048(7)
_cell_measurement_reflns_used    1474
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3013
_cell_measurement_theta_min      3.1939
_cell_volume                     1362.5(2)
_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      293.15
_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  -56.00    3.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -38.0000  -30.0000 59

  2 omega  -88.00  -27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -38.0000  120.0000 61

  3 omega  -22.00   34.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   77.0000  -60.0000 56
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0612522000
_diffrn_orient_matrix_UB_12      0.0042267000
_diffrn_orient_matrix_UB_13      -0.0052131000
_diffrn_orient_matrix_UB_21      0.0020638000
_diffrn_orient_matrix_UB_22      0.0427523000
_diffrn_orient_matrix_UB_23      -0.0371750000
_diffrn_orient_matrix_UB_31      -0.0087074000
_diffrn_orient_matrix_UB_32      -0.0194395000
_diffrn_orient_matrix_UB_33      -0.0829723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5211
_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         25.341
_diffrn_reflns_theta_min         3.200
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87713
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0561P)^2^+0.1707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1811
_reflns_number_total             2486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02150_si_001.cif
_cod_data_source_block           171201_wt171128
_cod_database_code               4036013
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.960
_reflns_odcompleteness_completeness 99.59
_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:
 C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              26392
_shelx_hkl_checksum              12667
_olex2_submission_special_instructions 'No special instructions were received'