Aryl-substituents moderate the nature of hydrogen bonds, N–H⋯N versus N–H⋯O, leading to supramolecular chains in the crystal structures of N-arylamino 1,2,3-triazole esters
Cunha, Anna C.; Ferreira, Vitor F.; Jordão, Alessandro K.; de Souza, Maria C. B. V.; Wardell, Solange M. S. V.; Wardell, James L.; Tan, Peiyu Amelia; Bettens, Ryan P. A.; Seth, Saikat Kumar; Tiekink, Edward R. T.; CrystEngComm 15 (2013) 4917–; doi:10.1039/c3ce40102b

data_7210108
_publ_section_title
;
 Aryl-substituents moderate the nature of hydrogen bonds, N--H&#x22EF;N
 versus N--H&#x22EF;O, leading to supramolecular chains in the crystal
 structures of N-arylamino 1,2,3-triazole esters
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4917
_journal_paper_doi               10.1039/c3ce40102b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C12 H13 F N4 O2 '
_chemical_formula_sum            'C12 H13 F N4 O2'
_chemical_formula_weight         264.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 95.722(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.057(3)
_cell_length_b                   17.510(4)
_cell_length_c                   14.102(4)
_cell_measurement_reflns_used    8525
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     2471.0(12)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'fine-slice \w scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6911
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.042
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21852
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.6
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.25
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6056
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.11
_refine_ls_R_factor_all          0.081
_refine_ls_R_factor_gt           0.064
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+1.3685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.174
_refine_ls_wR_factor_ref         0.187
_reflns_number_gt                4711
_reflns_number_total             6059
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c3ce40102b.txt
_cod_data_source_block           shelx2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C12 H13 F N4 O2 '
_cod_database_code               7210108