The differing influence of halides upon supramolecular aggregation through C–X⋯π interactions in the crystal structures of (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H, F and Cl
Jordão, Alessandro K.; Ferreira, Vitor F.; Cunha, Anna C.; Wardell, James L.; Wardell, Solange M. S. V.; Tiekink, Edward R. T.; CrystEngComm 14 (2012) 6534–; doi:10.1039/c2ce25841b

data_7208764
_publ_section_title
;
 The differing influence of halides upon supramolecular aggregation
 through C--X&#x22EF;\p interactions in the crystal structures of
 (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X
 = H, F and Cl
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              6534
_journal_paper_doi               10.1039/c2ce25841b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C10 H11 F N4 O'
_chemical_formula_sum            'C10 H11 F N4 O'
_chemical_formula_weight         222.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 118.641(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4975(6)
_cell_length_b                   6.6420(2)
_cell_length_c                   13.5534(6)
_cell_measurement_reflns_used    2595
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1066.39(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and 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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker-Nonius Roper CCD camera on a \k-goniostat
;
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9414
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.858198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0214P)^2^+1.0457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2012
_reflns_number_total             2434
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2ce25841b.txt
_cod_data_source_block           f
_cod_original_cell_volume        1066.39(7)
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7208764