Base free regioselective synthesis of α-triazolylazine derivatives
Harisha, Mysore Bhyrappa; Nagaraj, Muthupandi; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai; RSC Adv.  (2016) –; doi:10.1039/C6RA10452E

data_7225509
_publ_section_title
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 Base free regioselective synthesis of \a-triazolylazine derivatives
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_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA10452E
_journal_year                    2016
_chemical_formula_moiety         'C13 H9 Cl N4'
_chemical_formula_sum            'C13 H9 Cl N4'
_chemical_formula_weight         256.69
_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
_audit_creation_date             2015-11-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
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_audit_update_record
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2016-04-22 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.543(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1789(3)
_cell_length_b                   9.8168(4)
_cell_length_c                   22.5328(10)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      61.253
_cell_measurement_theta_min      3.930
_cell_volume                     1143.38(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 0.809
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.809
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17151
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         61.256
_diffrn_reflns_theta_min         3.931
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.836
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.3470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1552 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.4614.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+1.0115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1636
_reflns_number_total             1671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra10452e2.cif
_cod_data_source_block           hdp5
_cod_database_code               7225509
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.629
_shelx_estimated_absorpt_t_min   0.295
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C9(H9), C10(H10), C4(H4), C2(H2), C3(H3), C12(H12), C11(H11)
;
_shelx_res_checksum              69705
_olex2_submission_special_instructions 'No special instructions were received'