Mechanistic Insights into N-N Bond Cleavage in Catalytic Guanylation Reactions between 1,2-Diarylhydrazines and Carbodiimides.
Xu, Ling; Wang, Yu-Chen; Ma, Wangyang; Zhang, Wen-Xiong; Xi, Zhenfeng; The Journal of organic chemistry 79 (2014) 12004–12009; doi:10.1021/jo501865b

data_4030085
_publ_section_title
;
 Mechanistic Insights into N-N Bond Cleavage in Catalytic Guanylation
 Reactions between 1,2-Diarylhydrazines and Carbodiimides.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12004
_journal_page_last               12009
_journal_paper_doi               10.1021/jo501865b
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C46 H66 Li2 N8 O2'
_chemical_formula_sum            'C46 H66 Li2 N8 O2'
_chemical_formula_weight         776.94
_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
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Olex2 1.2
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_cell_measurement_reflns_used    4669
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
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(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_orient_matrix_UB_12      0.0539173000
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_diffrn_orient_matrix_UB_31      -0.0331528000
_diffrn_orient_matrix_UB_32      0.0180539000
_diffrn_orient_matrix_UB_33      -0.0175565000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
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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         26.022
_diffrn_reflns_theta_min         2.862
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
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_exptl_crystal_density_diffrn    1.133
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_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.500
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         4491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0449
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+3.2419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_total             4491
_reflns_threshold_expression     'I > 2\s(I)'
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'Adding full bibliography for 4030083--4030085.cif.'
_cod_database_code               4030085
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C30 H20 N4 Li'
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_reflns_odcompleteness_completeness 99.83
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 N5(H5), C3(H3), C4(H4), C5(H5A), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;