Cu(ii)-catalyzed domino reaction of 2H-azirines with diazotetramic and diazotetronic acids. Synthesis of 2-substituted 2H-1,2,3-triazoles.
Rostovskii, Nikolai V.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Korneev, Sergei M.; Yufit, Dmitry S.; Organic & biomolecular chemistry 11 (2013) 5535–5545; doi:10.1039/c3ob40708j

data_7153013
_publ_section_title
;
 Cu(ii)-catalyzed domino reaction of 2H-azirines with diazotetramic and
 diazotetronic acids. Synthesis of 2-substituted 2H-1,2,3-triazoles.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5535
_journal_page_last               5545
_journal_paper_doi               10.1039/c3ob40708j
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C22 H21 N5 O2, C4 H8 O2'
_chemical_formula_sum            'C26 H29 N5 O4'
_chemical_formula_weight         475.54
_chemical_melting_point          470(3)
_chemical_name_systematic
;
(3aRS,6aRS)-6a-Hydroxy-2-(4-methylphenyl)-3a-[4-(4-methylphenyl)-
2H-1,2,3-triazol-2-yl]-3,5,6,6a-tetrahydropyrrolo[3,4-b]pyrrole-4(3H)-one
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-12-23
_audit_creation_method
;
Olex2 1.1-beta
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                94.869(4)
_cell_angle_beta                 113.495(4)
_cell_angle_gamma                104.707(4)
_cell_formula_units_Z            2
_cell_length_a                   10.9436(5)
_cell_length_b                   11.0673(6)
_cell_length_c                   11.6719(5)
_cell_measurement_reflns_used    5233
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.7898
_cell_measurement_theta_min      3.0213
_cell_volume                     1226.08(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1 omega -103.00 -77.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 -179.0000 90.0000 26

2 omega -92.00 -8.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 -38.0000 30.0000 84

3 omega -71.00 -34.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 -179.0000 -120.0000 37

4 omega -43.00 45.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 38.0000 -150.0000 88

5 omega -40.00 -6.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 -57.0000 60.0000 34

6 omega -63.00 -32.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 179.0000 -180.0000 31

7 omega -104.00 -78.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 179.0000 -180.0000 26

8 omega 5.00 69.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 27.9882 -100.0000 30.0000 64

9 omega 56.00 82.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 27.9882 179.0000 0.0000 26

10 omega 70.00 96.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 27.9882 77.0000 120.0000 26

11 omega -1.00 25.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 27.9882 77.0000 120.0000 26

12 omega 44.00 70.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 27.9882 -100.0000 -120.0000 26

13 omega -96.00 -71.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 -57.0000 150.0000 25

14 omega -96.00 -6.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -27.3632 -57.0000 -120.0000 90
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      0.0025908000
_diffrn_orient_matrix_UB_12      0.0610126000
_diffrn_orient_matrix_UB_13      0.0269996000
_diffrn_orient_matrix_UB_21      0.0691064000
_diffrn_orient_matrix_UB_22      0.0095575000
_diffrn_orient_matrix_UB_23      0.0470521000
_diffrn_orient_matrix_UB_31      0.0276031000
_diffrn_orient_matrix_UB_32      0.0279050000
_diffrn_orient_matrix_UB_33      -0.0406211000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_xray_symbol    Mo
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15824
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_type              'sealed tube'
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         6486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0600P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                5298
_reflns_number_total             6486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40708j.txt
_cod_data_source_block           3a_dax41
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '194-200 C' was changed to '470(3)' -
it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1226.08(10)
_cod_database_code               7153013
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.93