Synthesis of geminal bis- and tristriazoles: exploration of unconventional azide chemistry.
Erhardt, Hellmuth; Mohr, Fabian; Kirsch, Stefan F.; Chemical communications (Cambridge, England) 52 (2016) 545–548; doi:10.1039/c5cc08163g

data_7118187
_publ_section_title
;
 Synthesis of geminal bis- and tristriazoles: exploration of
 unconventional azide chemistry.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              545
_journal_page_last               548
_journal_paper_doi               10.1039/c5cc08163g
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C31 H25 N9 O6'
_chemical_formula_sum            'C31 H25 N9 O6'
_chemical_formula_weight         619.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-19
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:32:32, GUI svn.r4372)
;
_audit_update_record
;
2015-09-29 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.677(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6712(4)
_cell_length_b                   12.4890(8)
_cell_length_c                   17.0137(11)
_cell_measurement_reflns_used    5926
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.0790
_cell_measurement_theta_min      2.4950
_cell_volume                     2986.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2705
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.8353
_diffrn_measurement_details
;
  1 omega  -48.00   12.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805  -57.0000  150.0000 60

  2 omega  -10.00   82.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805   77.0000  -60.0000 92

  3 omega   28.00   65.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805 -124.0000 -142.0000 37

  4 omega  -50.00   24.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805  -77.0000  -90.0000 74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0468092000
_diffrn_orient_matrix_UB_12      -0.0121332000
_diffrn_orient_matrix_UB_13      0.0011600000
_diffrn_orient_matrix_UB_21      0.0089439000
_diffrn_orient_matrix_UB_22      -0.0552926000
_diffrn_orient_matrix_UB_23      -0.0037715000
_diffrn_orient_matrix_UB_31      0.0165672000
_diffrn_orient_matrix_UB_32      -0.0044561000
_diffrn_orient_matrix_UB_33      0.0433489000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16696
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         29.53
_diffrn_reflns_theta_min         2.05
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.9768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1298
_reflns_number_gt                4764
_reflns_number_total             6959
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc08163g2.cif
_cod_data_source_block           oche523
_cod_database_code               7118187
_chemical_oxdiff_formula         C31H25N9O6
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H22 of C22, H12 of C12, H19 of C19, H8 of C8, H10 of C10, H9 of C9, H11 of
  C11, H1 of C1, H2 of C2, {H25A,H25B} of C25, {H5A,H5B} of C5, H7 of C7, H29
  of C29, H31 of C31, H30 of C30, {H15A,H15B} of C15, H28 of C28, H27 of C27,
  H17 of C17, H21 of C21, H20 of C20, H18 of C18
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C5(H5A,H5B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C22(H22), C11(H11), C2(H2), C7(H7), C29(H29), C31(H31), C30(H30),
 C28(H28), C27(H27), C17(H17), C21(H21), C20(H20), C18(H18), C19(H19), C8(H8),
 C10(H10), C9(H9)
;