5-Amino-1-(2-chloronicotinoyl)-3-trifluoromethyl-1<i>H</i>-1,2,4-triazole: hydrogen-bonded sheets of alternating <i>R</i>~2~^2^(8) and <i>R</i>~6~^6^(36) rings
Wardell, James L.; Low, John N.; Glidewell, Christopher; Acta Crystallographica Section E 62 (2006) o5383–o5385; doi:10.1107/S1600536806044990

data_2211503
_publ_section_title
;
 5-Amino-1-(2-chloronicotinoyl)-3-trifluoromethyl-1<i>H</i>-1,2,4-triazole:
 hydrogen-bonded sheets of alternating <i>R</i>~2~^2^(8) and
 <i>R</i>~6~^6^(36) rings
;
_journal_coeditor_code           LH2228
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5383
_journal_page_last               o5385
_journal_paper_doi               10.1107/S1600536806044990
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H5 Cl F3 N5 O'
_chemical_formula_moiety         'C9 H5 Cl F3 N5 O'
_chemical_formula_sum            'C9 H5 Cl F3 N5 O'
_chemical_formula_weight         291.63
_chemical_name_systematic
;
5-Amino-1-(2-chloronicotinoyl)-3-trifluoromethyl-1H-1,2,4-triazole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.147(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.64770(10)
_cell_length_b                   19.7414(10)
_cell_length_c                   12.3721(5)
_cell_measurement_reflns_used    2588
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      3.89
_cell_volume                     1134.94(8)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14659
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         3.89
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0386P)^2^+0.619P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                1923
_reflns_number_total             2588
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            lh2228.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2211503
_cod_database_fobs_code          2211503