I2-Catalyzed Oxidative Coupling Reactions of Hydrazones and Amines and the Application in the Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazoles.
Chen, Zhengkai; Li, Hongli; Dong, Weipeng; Miao, Maozhong; Ren, Hongjun; Organic letters 18 (2016) 1334–1337; doi:10.1021/acs.orglett.6b00277

data_1542567
_publ_section_title
;
 I2-Catalyzed Oxidative Coupling Reactions of Hydrazones and Amines and
 the Application in the Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazoles.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1334
_journal_page_last               1337
_journal_paper_doi               10.1021/acs.orglett.6b00277
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C21 H17 N3 O'
_chemical_formula_sum            'C21 H17 N3 O'
_chemical_formula_weight         327.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-02
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_angle_alpha                90.00
_cell_angle_beta                 99.879(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.9422(11)
_cell_length_b                   9.9101(7)
_cell_length_c                   19.1301(11)
_cell_measurement_reflns_used    1876
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.3208
_cell_measurement_theta_min      3.0552
_cell_volume                     3351.1(4)
_computing_cell_refinement
;
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_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0131257000
_diffrn_orient_matrix_UB_12      -0.0317945000
_diffrn_orient_matrix_UB_13      0.0330215000
_diffrn_orient_matrix_UB_21      -0.0335636000
_diffrn_orient_matrix_UB_22      0.0196641000
_diffrn_orient_matrix_UB_23      0.0121918000
_diffrn_orient_matrix_UB_31      -0.0176451000
_diffrn_orient_matrix_UB_32      -0.0610479000
_diffrn_orient_matrix_UB_33      -0.0133008000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6684
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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)
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    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+1.0286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                2336
_reflns_number_total             3059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00277_si_003.cif
_cod_data_source_block           150702_dwp_3_153
_cod_depositor_comments          'Adding full bibliography for 1542567.cif.'
_cod_database_code               1542567
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;