#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/97/2009712.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_2009712
loop_
_publ_author_name
'Abdul-Ghani, M.'
'Pritchard, R.G.'
'Tipping, A.E.'
_publ_section_title
;(2Z,4E,6E)-8-Ethyl-1,1,1-trifluoro-5-trifluoromethyl-3,4,8-triazadeca-2,4,6-triene-2-amine:
 formation of hydrogen-bonded pairs via an amine--diazine interaction
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              719
_journal_page_last               721
_journal_paper_doi               10.1107/S0108270193012296
_journal_volume                  50
_journal_year                    1994
_chemical_formula_analytical     'C10 H14 F6 N4'
_chemical_formula_moiety         'C10 H14 F6 N4'
_chemical_formula_structural     'C10 H14 F6 N4'
_chemical_formula_sum            'C10 H14 F6 N4'
_chemical_formula_weight         304.24
_chemical_melting_point          352.0(10)
_chemical_name_systematic
;2-Amino-8-ethyl-1,1,1-trifluoro-5-trifluoromethyl-3,4,8-triazadeca-(Z)-2,(E)-
4,(E)-6-triene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 101.46(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8.00
_cell_length_a                   23.223(7)
_cell_length_b                   13.044(3)
_cell_length_c                   9.724(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      35.11
_cell_measurement_theta_min      20.70
_cell_volume                     2886.9(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'TEXSAN: PROCESS (MSC, 1985)'
_computing_molecular_graphics    'TEXSAN: PLUTO (Motherwell & Clegg, 1978)'
_computing_publication_material
'TEXSAN: FINISH (MSC, 1985). Literature Survey: CSSR (1984)'
_computing_structure_refinement  'TEXSAN: LS (MSC, 1985)'
_computing_structure_solution    'TEXSAN: MITHRIL (Gilmore, 1984)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       AFC6S
_diffrn_measurement_method       'ω/2-θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2741
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.0
_diffrn_standards_decay_%        4.80
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.1354
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         -0.19784
_refine_diff_density_min         0.34092
_refine_ls_extinction_coef       3.2(1)E-7
_refine_ls_extinction_method     Zachariasen_type_2_Gaussian_isotropic
_refine_ls_goodness_of_fit_obs   2.456
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1198
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0554
_refine_ls_shift/esd_max         0.0046
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0684
_reflns_number_observed          1198
_reflns_number_total             2671
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            hu1066.cif
_cod_data_source_block           UMIST50
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '351-353 K' was changed to
'352.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value ' 351-353 K ' was changed to
'352.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2886(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        ' C10 H14 F6 N4 '
_cod_database_code               2009712
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
' -x,-y,-z'
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
F(1) 1.0007(2) 0.3988(3) 0.5933(4) 0.0845
F(2) 1.0344(2) 0.3295(3) 0.4287(4) 0.0930
F(3) 1.0550(2) 0.2668(3) 0.6337(4) 0.0841
F(4) 0.8278(3) -0.0659(5) 0.6880(5) 0.0726
F(5) 0.8195(3) -0.0216(6) 0.4768(6) 0.1256
F(6) 0.8818(3) -0.1342(4) 0.5618(9) 0.1229
F(7) 0.802(2) 0.020(3) 0.569(6) 0.14(2)
F(8) 0.8530(10) -0.082(2) 0.486(3) 0.049(9)
F(9) 0.853(2) -0.097(3) 0.680(5) 0.10(2)
N(1) 0.9292(2) 0.0389(4) 0.7667(5) 0.0545
N(3) 0.9156(2) 0.0886(3) 0.5287(4) 0.0435
N(4) 0.9638(2) 0.1545(3) 0.5699(4) 0.0423
N(8) 0.8579(3) 0.4085(4) 0.2527(6) 0.0865
C(1) 0.8579(3) -0.0446(5) 0.5888(6) 0.0609
C(2) 0.9048(2) 0.0344(3) 0.6307(5) 0.0392
C(5) 0.9578(2) 0.2417(4) 0.5052(5) 0.0426
C(6) 0.9072(3) 0.2787(4) 0.4116(6) 0.0531
C(7) 0.9038(3) 0.3700(5) 0.3443(6) 0.0646
C(9) 0.8625(3) 0.5072(5) 0.1797(8) 0.0991
C(10) 0.8278(4) 0.5877(6) 0.2220(10) 0.1269
C(11) 1.0118(3) 0.3074(4) 0.5413(6) 0.0592
C(12) 0.8047(5) 0.3465(7) 0.2030(10) 0.1317
C(13) 0.7679(5) 0.3441(10) 0.3010(10) 0.1869
H(1A) 0.919(2) 0.007(3) 0.818(5) 0.03(2)
H(1B) 0.965(3) 0.093(5) 0.802(6) 0.11(2)
H(6) 0.872(2) 0.237(3) 0.406(4) 0.040(10)
H(7) 0.936(3) 0.421(5) 0.375(7) 0.13(2)
H(12A) 0.7836 0.3752 0.1175 0.1581
H(12B) 0.8161 0.2784 0.1858 0.1581
H(13A) 0.7560 0.4119 0.3180 0.2243
H(13B) 0.7343 0.3036 0.2661 0.2243
H(13C) 0.7887 0.3153 0.3866 0.2243
H(9A) 0.9025 0.5281 0.1988 0.1190
H(9B) 0.8498 0.4966 0.0817 0.1190
H(10A) 0.8398 0.5990 0.3203 0.1523
H(10B) 0.8331 0.6488 0.1731 0.1523
H(10C) 0.7875 0.5687 0.2015 0.1523
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables'
H 0.000 0.000 'International Tables'
F 0.014 0.010 'International Tables'
N 0.004 0.003 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -6 0
-5 -5 -1
8 -4 -1
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
F(7) F(4) F(9) 120(4) ?
F(7) F(4) C(1) 61(2) ?
F(9) F(4) C(1) 60(4) ?
F(7) F(5) F(8) 127(3) ?
F(7) F(5) C(1) 75(2) ?
F(8) F(5) C(1) 54.0(10) ?
F(8) F(6) F(9) 91(2) ?
F(8) F(6) C(1) 52.0(10) ?
F(9) F(6) C(1) 47(2) ?
F(4) F(7) F(5) 96(3) ?
F(4) F(7) C(1) 50.0(10) ?
F(5) F(7) C(1) 56(2) ?
F(5) F(8) F(6) 144(3) ?
F(5) F(8) C(1) 72(2) ?
F(6) F(8) C(1) 74(2) ?
F(4) F(9) F(6) 137(5) ?
F(4) F(9) C(1) 87(4) ?
F(6) F(9) C(1) 58(2) ?
N(4) N(3) C(2) 112.6(4) yes
N(3) N(4) C(5) 113.4(4) yes
C(7) N(8) C(9) 121.2(6) yes
C(7) N(8) C(12) 121.1(6) yes
C(9) N(8) C(12) 116.9(5) yes
F(4) C(1) F(5) 106.5(6) yes
F(4) C(1) F(6) 104.9(6) yes
F(4) C(1) F(7) 70(2) ?
F(4) C(1) F(8) 126.0(10) ?
F(4) C(1) F(9) 33(2) ?
F(4) C(1) C(2) 114.0(5) ?
F(5) C(1) F(6) 106.1(7) ?
F(5) C(1) F(7) 49(2) ?
F(5) C(1) F(8) 54(2) ?
F(5) C(1) F(9) 129(2) ?
F(5) C(1) C(2) 114.3(5) ?
F(6) C(1) F(7) 146(2) ?
F(6) C(1) F(8) 53(2) ?
F(6) C(1) F(9) 75(2) ?
F(6) C(1) C(2) 110.3(5) ?
F(7) C(1) F(8) 102(2) ?
F(7) C(1) F(9) 102(3) ?
F(7) C(1) C(2) 102(2) ?
F(8) C(1) F(9) 115(3) ?
F(8) C(1) C(2) 120.0(10) ?
F(9) C(1) C(2) 112(2) ?
N(1) C(2) N(3) 129.3(5) ?
N(1) C(2) C(1) 116.3(5) ?
N(3) C(2) C(1) 114.4(5) yes
N(4) C(5) C(6) 127.2(5) yes
N(4) C(5) C(11) 112.6(5) ?
C(6) C(5) C(11) 120.1(5) ?
C(5) C(6) C(7) 124.8(6) yes
N(8) C(7) C(6) 127.7(7) yes
N(8) C(9) C(10) 113.5(7) ?
F(1) C(11) F(2) 104.7(5) ?
F(1) C(11) F(3) 106.2(5) ?
F(1) C(11) C(5) 112.4(5) ?
F(2) C(11) F(3) 106.0(5) ?
F(2) C(11) C(5) 112.2(5) ?
F(3) C(11) C(5) 114.6(4) ?
N(8) C(12) C(13) 112.0(10) ?
C(2) N(1) H(1A) 122(4) ?
C(2) N(1) H(1B) 119(3) ?
H(1A) N(1) H(1B) 119(5) ?
C(5) C(6) H(6) 115(3) ?
C(7) C(6) H(6) 120(3) ?
N(8) C(7) H(7) 113(4) ?
C(6) C(7) H(7) 118(4) ?
N(8) C(9) H(9A) 108.45 ?
N(8) C(9) H(9B) 108.45 ?
C(10) C(9) H(9A) 108.46 ?
C(10) C(9) H(9B) 108.45 ?
H(9A) C(9) H(9B) 109.47 ?
C(9) C(10) H(10A) 109.48 ?
C(9) C(10) H(10B) 109.49 ?
H(10A) C(10) H(10B) 109.46 ?
H(10A) C(10) H(10C) 109.44 ?
H(10B) C(10) H(10C) 109.47 ?
N(8) C(12) H(12A) 108.92 ?
N(8) C(12) H(12B) 108.92 ?
C(13) C(12) H(12A) 108.98 ?
C(13) C(12) H(12B) 108.98 ?
H(12A) C(12) H(12B) 109.45 ?
C(12) C(13) H(13A) 109.43 ?
C(12) C(13) H(13B) 109.39 ?
C(12) C(13) H(13C) 109.43 ?
H(13A) C(13) H(13B) 109.51 ?
H(13A) C(13) H(13C) 109.55 ?
H(13B) C(13) H(13C) 109.52 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F(1) C(11) . . 1.340(6) ?
F(2) C(11) . . 1.336(6) ?
F(3) C(11) . . 1.317(6) ?
F(4) F(7) . . 1.63(5) ?
F(4) F(9) . . 0.73(4) ?
F(4) C(1) . . 1.329(8) ?
F(5) F(7) . . 1.18(5) ?
F(5) F(8) . . 1.10(3) ?
F(5) C(1) . . 1.298(7) ?
F(6) F(8) . . 1.12(3) ?
F(6) F(9) . . 1.52(5) ?
F(6) C(1) . . 1.342(8) ?
F(7) C(1) . . 1.52(4) ?
F(8) C(1) . . 1.10(3) ?
F(9) C(1) . . 1.15(5) ?
N(1) C(2) . . 1.332(6) yes
N(3) N(4) . . 1.405(5) yes
N(3) C(2) . . 1.283(5) yes
N(4) C(5) . . 1.294(6) yes
N(8) C(7) . . 1.344(7) yes
N(8) C(9) . . 1.484(8) yes
N(8) C(12) . . 1.480(10) yes
C(1) C(2) . . 1.495(7) yes
C(5) C(6) . . 1.422(7) yes
C(5) C(11) . . 1.501(7) yes
C(6) C(7) . . 1.353(7) yes
C(9) C(10) . . 1.430(10) yes
C(12) C(13) . . 1.410(10) yes
N(1) H(1A) . . 0.73(4) ?
N(1) H(1B) . . 1.10(7) ?
C(6) H(6) . . 0.96(4) ?
C(7) H(7) . . 1.01(7) ?
C(9) H(9A) . . 0.950 ?
C(9) H(9B) . . 0.950 ?
C(10) H(10A) . . 0.950 ?
C(10) H(10B) . . 0.950 ?
C(10) H(10C) . . 0.950 ?
C(12) H(12A) . . 0.950 ?
C(12) H(12B) . . 0.950 ?
C(13) H(13A) . . 0.950 ?
C(13) H(13B) . . 0.950 ?
C(13) H(13C) . . 0.950 ?
