Expedient and Rapid Synthesis of 1,2,3-Triazolo[5,1-c]morpholines through Palladium-Copper Catalysis
Chinmay Chowdhury; Sanjukta Mukherjee; Bimolendu Das; Basudeb Achari; Journal of Organic Chemistry 74 (2009) 3612–3615; doi:10.1021/jo900428j

data_4024516
_publ_section_title
;
Expedient and Rapid Synthesis of 1,2,3-Triazolo[5,1-c]morpholines through
Palladium-Copper Catalysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3612
_journal_page_last               3615
_journal_paper_doi               10.1021/jo900428j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         C18H16N4O3
_chemical_formula_sum            'C18 H16 N4 O3'
_chemical_formula_weight         336.35
_chemical_melting_point          154.5(5)
_chemical_name_common            triazolomorpholine
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3308(3)
_cell_length_b                   7.2577(2)
_cell_length_c                   39.1469(9)
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_volume                     3219.27(14)
_computing_cell_refinement       'Apex 2, Bruker Kappa'
_computing_data_collection       'Apex 2, Bruker Kappa'
_computing_data_reduction        'Apex 2, Bruker Kappa'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa Apex 2'
_diffrn_measurement_method       'Difference Vectors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            21241
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.04
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-shaped
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1662
_reflns_number_gt                2945
_reflns_number_total             3662
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900428j_si_002.cif
_cod_data_source_block           cc_snj1_106
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '154-155' was changed to '154.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

2020-11-05
Z value fixed to be consistent with given formula 
                 miguel
;
_cod_original_sg_symbol_H-M      Pbca
_cod_original_formula_units_Z    7
_cod_database_code               4024516