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_7118186
_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         'C12 H14 N6 O6'
_chemical_formula_sum            'C12 H14 N6 O6'
_chemical_formula_weight         338.29
_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             2014-10-31
_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                 101.6053(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.22642(18)
_cell_length_b                   9.71725(18)
_cell_length_c                   18.0546(4)
_cell_measurement_reflns_used    5140
_cell_measurement_temperature    150
_cell_measurement_theta_max      32.4960
_cell_measurement_theta_min      2.2550
_cell_volume                     1585.60(6)
_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      150
_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 0.8942
_diffrn_measurement_details
;
  1 omega   -2.00   76.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000  120.0000 78

  2 omega    2.00   48.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000 -150.0000 46

  3 omega    8.00   91.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000 -120.0000 83

  4 omega    3.00   86.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000    0.0000 83

  5 omega   54.00   81.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000  -60.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0215862000
_diffrn_orient_matrix_UB_12      -0.0533919000
_diffrn_orient_matrix_UB_13      -0.0222791000
_diffrn_orient_matrix_UB_21      0.0540696000
_diffrn_orient_matrix_UB_22      -0.0220351000
_diffrn_orient_matrix_UB_23      0.0314503000
_diffrn_orient_matrix_UB_31      -0.0526615000
_diffrn_orient_matrix_UB_32      -0.0445825000
_diffrn_orient_matrix_UB_33      0.0111169000
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12718
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         32.93
_diffrn_reflns_theta_min         2.30
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98375
_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    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0535P)^2^+0.4688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                4247
_reflns_number_total             5307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc08163g2.cif
_cod_data_source_block           oche386
_cod_original_cell_volume        1585.60(5)
_cod_database_code               7118186
_chemical_oxdiff_formula         C12H14N6O6
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H9 of C9, {H3A,H3B} of C3, H5 of C5
 At 1.5 times of:
  {H4A,H4B,H4C} of C4, {H8A,H8B,H8C} of C8, {H12A,H12B,H12C} of C12
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C4(H4A,H4B,H4C)
;