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_7210110
_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 Br N4 O2'
_chemical_formula_sum            'C12 H13 Br N4 O2'
_chemical_formula_weight         325.17
_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                90.00
_cell_angle_beta                 105.3049(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7435(3)
_cell_length_b                   9.9927(2)
_cell_length_c                   11.1150(3)
_cell_measurement_reflns_used    3306
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1365.21(6)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20395
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.8
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.015
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.54
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.028
_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^)+(0.0359P)^2^+0.6692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.066
_refine_ls_wR_factor_ref         0.071
_reflns_number_gt                2583
_reflns_number_total             3126
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c3ce40102b.txt
_cod_data_source_block           1093
_cod_original_cell_volume        1365.17(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7210110