A highly efficient tandem [3+2] “click” cycloaddition /6-exo-cyclization strategy for the construction of triazole fused pyrazines
Bandyopadhyay, Subhajit; Roy, Biswajit; Hatai, Joydev; Mondal, Debashis; RSC Adv.  (2014) –; doi:10.1039/C4RA12489H

data_7218596
_publ_section_title
;
 A highly efficient tandem [3+2] &#x201C;click&#x201D; cycloaddition
 /6-exo-cyclization strategy for the construction of triazole fused
 pyrazines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA12489H
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H17 N O'
_chemical_formula_sum            'C15 H17 N O'
_chemical_formula_weight         227.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-07
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.9173(15)
_cell_length_b                   6.7330(3)
_cell_length_c                   7.7378(5)
_cell_measurement_reflns_used    1342
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      24.9320
_cell_measurement_theta_min      3.1270
_cell_volume                     1246.06(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 7.9580
_diffrn_measured_fraction_theta_full 0.8669
_diffrn_measured_fraction_theta_max 0.7097
_diffrn_measurement_details
;
  1 omega   36.00  117.00   1.0000   42.0600
omega____ theta____ kappa____ phi______ frames
    -       27.3512  178.0000 -180.0000 81

  2 omega   64.00  101.00   1.0000   42.0600
omega____ theta____ kappa____ phi______ frames
    -       27.3512   57.0000 -180.0000 37

  3 omega   -5.00   44.00   1.0000   42.0600
omega____ theta____ kappa____ phi______ frames
    -       27.3512  -77.0000 -134.0000 49
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0284767000
_diffrn_orient_matrix_UB_12      0.0292788000
_diffrn_orient_matrix_UB_13      -0.0042844000
_diffrn_orient_matrix_UB_21      -0.0060578000
_diffrn_orient_matrix_UB_22      -0.0835934000
_diffrn_orient_matrix_UB_23      -0.0527288000
_diffrn_orient_matrix_UB_31      -0.0057443000
_diffrn_orient_matrix_UB_32      -0.0571328000
_diffrn_orient_matrix_UB_33      0.0747373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2554
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.70
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1575
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0906P)^2^+0.5005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                1469
_reflns_number_total             1575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra12489h2.cif
_cod_data_source_block           sb_br_85
_cod_database_code               7218596
_chemical_oxdiff_formula         'C14 H15 N O'
_reflns_odcompleteness_completeness 86.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32