Site-Selective Conversion of Azido Groups at Carbonyl α-Positions into Oxime Groups Leading Triazide to Triple Click Conjugation Scaffold
Yokoi, Taiki; Ueda, Tomomi; Tanimoto, Hiroki; Morimoto, Tsumoru; Kakiuchi, Kiyomi; Chemical Communications  (2018) –; doi:10.1039/C8CC09415B

data_7122741
_publ_section_title
;
 Site-Selective Conversion of Azido Groups at Carbonyl \a-Positions into
 Oxime Groups Leading Triazide to Triple Click Conjugation Scaffold
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09415B
_journal_year                    2018
_chemical_formula_moiety         'C16 H20 N8 O3'
_chemical_formula_sum            'C16 H20 N8 O3'
_chemical_formula_weight         372.39
_chemical_melting_point          358.5(5)
_chemical_name_common            'trialkyl diazido oxime'
_chemical_name_systematic
2-Azido-N-(6-azidohexyl)-N-(3-(2-(hydroxyimino)acetyl)phenyl)acetamide
_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
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-11-15 deposited with the CCDC.
2018-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.938(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   13.5247(4)
_cell_length_b                   7.64772(17)
_cell_length_c                   17.7480(5)
_cell_measurement_reflns_used    18562
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.04
_cell_volume                     1818.14(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         2.317
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.7498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2850
_reflns_number_total             3334
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8cc09415b2.cif
_cod_data_source_block           TY_11_038
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '358-359' was changed to '358.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7122741
_shelx_res_checksum              47766
_shelx_hkl_checksum              92361