Iodine-mediated oxidative N-N coupling of secondary amines to hydrazines.
Ren, Linning; Wang, Manman; Fang, Benyao; Yu, Wenquan; Chang, Junbiao; Organic & biomolecular chemistry 17 (2019) 3446–3450; doi:10.1039/c9ob00279k

data_7156728
_publ_section_title
;
 Iodine-mediated oxidative N-N coupling of secondary amines to hydrazines.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3446
_journal_page_last               3450
_journal_paper_doi               10.1039/c9ob00279k
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C24 H22 N4'
_chemical_formula_sum            'C24 H22 N4'
_chemical_formula_weight         366.45
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-11
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
;
2019-01-30 deposited with the CCDC.    2019-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.506(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8651(4)
_cell_length_b                   18.4812(9)
_cell_length_c                   11.3374(6)
_cell_measurement_reflns_used    2017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5360
_cell_measurement_theta_min      4.7200
_cell_volume                     1971.29(17)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -22.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -180.0000 59

  2 omega  -83.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -164.0000 -129.0000 26

  3 omega    0.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 69

  4 omega  -23.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -180.0000 46

  5 omega   11.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 58

  6 omega   16.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 88

  7 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 26

  8 omega   43.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 49

  9 omega  115.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 26

 10 omega  134.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 34

 11 omega   38.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 51

 12 omega   39.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 66

 13 omega   62.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 27

 14 omega   93.00  164.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 71

 15 omega   88.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 83

 16 omega   46.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 58

 17 omega   42.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0247069000
_diffrn_orient_matrix_UB_12      0.0383703000
_diffrn_orient_matrix_UB_13      -0.1253840000
_diffrn_orient_matrix_UB_21      0.0418272000
_diffrn_orient_matrix_UB_22      0.0727579000
_diffrn_orient_matrix_UB_23      0.0673693000
_diffrn_orient_matrix_UB_31      0.1563687000
_diffrn_orient_matrix_UB_32      -0.0134579000
_diffrn_orient_matrix_UB_33      0.0070913000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7612
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.700
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.235
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0791P)^2^+0.1297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                2644
_reflns_number_total             3517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00279k2.cif
_cod_data_source_block           201810397
_cod_depositor_comments          'Adding full bibliography for 7156728.cif.'
_cod_original_cell_volume        1971.28(17)
_cod_database_code               7156728
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.868
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12),
 C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'