#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/59/2015939.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015939
loop_
_publ_author_name
'Genivaldo Júlio Perpétuo'
'Jan Janczak'
_publ_section_title
;
 2,4-Diamino-6-methyl-1,3,5-triazin-1-ium trifluoroacetate
;
_journal_coeditor_code           FA3075
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o271
_journal_page_last               o273
_journal_paper_doi               10.1107/S0108270107010165
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C4 H8 N5 +, C2 F3 O2 -'
_chemical_formula_moiety         'C4 H8 N5 +, C2 F3 O2 -'
_chemical_formula_sum            'C6 H8 F3 N5 O2'
_chemical_formula_weight         239.17
_chemical_name_systematic
;
2,4-Diamino-6-methyl-1,3,5-triazin-1-ium trifluoroacetate
;
_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                 111.75(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.384(2)
_cell_length_b                   8.1870(10)
_cell_length_c                   13.013(3)
_cell_measurement_reflns_used    1182
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      3.01
_cell_volume                     1027.5(4)
_computing_cell_refinement
;
KM-4 CCD Software
;
_computing_data_collection
;
KM-4 CCD Software (Kuma, 2004)
;
_computing_data_reduction
;
KM-4 CCD Software
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Kuma KM-4 with CCD area-detector'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12223
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'face-indexed (SHELXTL; Sheldrick, 1990)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      1.54
_exptl_crystal_density_method    flotation
_exptl_crystal_description       paralellepiped
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.245
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0849P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1654
_reflns_number_gt                1548
_reflns_number_total             2563
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3075.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015939
_cod_database_fobs_code          2015939
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.17496(14) 0.06954(17) 0.00560(11) 0.0380(4) Uani d . 1
C C1 0.21154(16) 0.0574(2) 0.11798(14) 0.0364(4) Uani d . 1
N N2 0.33379(14) 0.09825(18) 0.19374(11) 0.0403(4) Uani d . 1
C C2 0.42717(17) 0.1559(2) 0.15526(13) 0.0397(4) Uani d . 1
N N3 0.39947(15) 0.16226(19) 0.04479(11) 0.0405(4) Uani d . 1
H H3 0.4623 0.1927 0.0210 0.049 Uiso calc R 1
C C3 0.27180(17) 0.1199(2) -0.02753(14) 0.0376(4) Uani d . 1
N N4 0.11718(16) -0.0009(2) 0.15326(12) 0.0493(5) Uani d . 1
H H41 0.1357 -0.0113 0.2231 0.059 Uiso calc R 1
H H42 0.0370 -0.0286 0.1065 0.059 Uiso calc R 1
N N5 0.54769(16) 0.2076(2) 0.22449(13) 0.0592(5) Uani d . 1
H H51 0.5663 0.2042 0.2946 0.071 Uiso calc R 1
H H52 0.6081 0.2448 0.1998 0.071 Uiso calc R 1
C C4 0.2464(2) 0.1301(3) -0.14743(15) 0.0577(6) Uani d . 1
H H4A 0.2674 0.0269 -0.1725 0.087 Uiso calc R 1
H H4B 0.3044 0.2133 -0.1595 0.087 Uiso calc R 1
H H4C 0.1508 0.1567 -0.1878 0.087 Uiso calc R 1
O O1 0.60611(13) 0.26716(18) -0.03446(10) 0.0545(4) Uani d . 1
O O2 0.74213(16) 0.3215(2) 0.13932(12) 0.0811(6) Uani d . 1
C C5 0.70961(18) 0.3255(2) 0.03901(15) 0.0553(5) Uani d . 1
C C6 0.8174(2) 0.4101(3) 0.00143(18) 0.0715(6) Uani d D 1
F F1 0.9273(7) 0.4553(19) 0.0797(4) 0.091(4) Uani d PD 0.50
F F2 0.7645(11) 0.5373(6) -0.0553(9) 0.089(4) Uani d PD 0.50
F F3 0.8416(7) 0.3252(6) -0.0749(6) 0.0872(12) Uani d PD 0.50
F F21 0.9279(7) 0.3213(5) 0.0217(11) 0.095(2) Uani d PD 0.50
F F22 0.8648(7) 0.5386(6) 0.0601(7) 0.092(2) Uani d PD 0.50
F F23 0.7725(7) 0.4749(17) -0.0943(4) 0.093(4) Uani d PD 0.50
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C1 115.75(14) y
N4 C1 N2 117.54(15) ?
N4 C1 N1 116.80(15) ?
N2 C1 N1 125.66(15) y
C1 N2 C2 116.02(14) y
N5 C2 N2 119.93(15) ?
N5 C2 N3 119.31(15) ?
N2 C2 N3 120.76(15) y
C3 N3 C2 119.59(16) y
C3 N3 H3 120.0 ?
C2 N3 H3 120.0 ?
N1 C3 N3 121.78(15) y
N1 C3 C4 120.55(16) ?
N3 C3 C4 117.65(16) ?
C1 N4 H41 120.0 ?
C1 N4 H42 120.0 ?
H41 N4 H42 120.0 ?
C2 N5 H51 120.0 ?
C2 N5 H52 120.0 ?
H51 N5 H52 120.0 ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
O2 C5 O1 129.17(18) y
O2 C5 C6 113.89(17) ?
O1 C5 C6 116.89(16) ?
F1 C6 F2 107.0(6) ?
F23 C6 F22 99.2(5) ?
F23 C6 F21 114.0(5) ?
F22 C6 F21 102.8(4) ?
F1 C6 F3 113.4(5) ?
F2 C6 F3 99.0(4) ?
F1 C6 C5 114.7(3) ?
F2 C6 C5 110.0(4) ?
F23 C6 C5 116.9(3) ?
F22 C6 C5 110.0(3) ?
F21 C6 C5 112.0(3) ?
F3 C6 C5 111.6(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 1.299(2) y
N1 C1 1.372(2) y
C1 N4 1.316(2) y
C1 N2 1.330(2) y
N2 C2 1.332(2) y
C2 N5 1.312(2) y
C2 N3 1.359(2) y
N3 C3 1.356(2) y
N3 H3 0.8600 ?
C3 C4 1.485(2) y
N4 H41 0.8600 ?
N4 H42 0.8600 ?
N5 H51 0.8600 ?
N5 H52 0.8600 ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
O1 C5 1.239(2) y
O2 C5 1.222(2) y
C5 C6 1.542(3) y
C6 F1 1.273(5) ?
C6 F2 1.277(6) ?
C6 F23 1.273(6) ?
C6 F22 1.286(5) ?
C6 F21 1.300(5) ?
C6 F3 1.311(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3 O1 . 0.86 1.98 2.836(2) 179.0
N5 H52 O2 . 0.86 1.94 2.799(2) 177.6
N4 H41 O2 2_645 0.86 2.24 2.935(2) 138.2
N4 H42 N1 3 0.86 2.17 3.024(2) 172.7
N5 H51 O1 4_566 0.86 2.12 2.974(2) 171.6
N5 H51 F23 4_566 0.86 2.55 3.027(7) 115.6
