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_7225510
_publ_section_title
;
 Base free regioselective synthesis of \a-triazolylazine derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA10452E
_journal_year                    2016
_chemical_formula_moiety         'C13 H8 Cl F N4'
_chemical_formula_sum            'C13 H8 Cl F N4'
_chemical_formula_weight         274.68
_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
_audit_creation_date             2015-11-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2016-04-22 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.89(4)
_cell_length_b                   5.933(9)
_cell_length_c                   14.48(2)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.729
_cell_measurement_theta_min      2.838
_cell_volume                     2396(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41117
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.681
_diffrn_reflns_theta_min         2.027
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1364 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.5485.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5583
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0243P)^2^+1.0097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5292
_reflns_number_total             5583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra10452e2.cif
_cod_data_source_block           hdp9
_cod_database_code               7225510
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.838
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.50(7) 0.50(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C3B(H3B), C5B(H5B), C7B(H7B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B),
 C13B(H13B)
;
_shelx_res_checksum              17093
_olex2_submission_special_instructions 'No special instructions were received'