#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:05:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180411 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/80/7208072.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7208072
loop_
_publ_author_name
'Railliet, Antoine P.'
'Safin, Damir A.'
'Robeyns, Koen'
'Garcia, Yann'
_publ_section_title
;
 Reaction of aminobenzoate esters with N,N′-dimethylformamide azine
 dihydrochloride: crucial influence of intramolecular hydrogen bonding for
 the formation of 1,2,4-triazoles
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              4812
_journal_paper_doi               10.1039/c2ce25095k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C6 H14 N4, C9 H11 N O2'
_chemical_formula_sum            'C15 H25 N5 O2'
_chemical_formula_weight         307.40
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.702(14)
_cell_angle_beta                 100.424(10)
_cell_angle_gamma                115.058(14)
_cell_formula_units_Z            2
_cell_length_a                   8.0454(5)
_cell_length_b                   8.9859(19)
_cell_length_c                   13.0298(17)
_cell_measurement_reflns_used    4210
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.2044
_cell_measurement_theta_min      2.5215
_cell_volume                     831.1(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '80 images, ΔΦ 3.0°'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_sigmaI/netI    0.0984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7192
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0472
_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/[σ²(Fo²)+(0.0705P)²+0.3388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                2532
_reflns_number_total             2819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25095k.txt
_cod_data_source_block           aror015
_cod_database_code               7208072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O19 O 0.44769(17) 0.64499(14) 0.32247(9) 0.0300(3) Uani 1 1 d .
O20 O 0.41244(15) 0.65744(13) 0.48938(8) 0.0229(3) Uani 1 1 d .
C13 C -0.0296(2) 0.1608(2) 0.26281(12) 0.0224(4) Uani 1 1 d .
H13 H -0.0759 0.0892 0.1977 0.027 Uiso 1 1 calc R
C12 C 0.1274(2) 0.31702(19) 0.27285(11) 0.0196(3) Uani 1 1 d .
C16 C 0.0993(2) 0.3660(2) 0.45348(11) 0.0217(3) Uani 1 1 d .
H16 H 0.1423 0.4362 0.5189 0.026 Uiso 1 1 calc R
N11 N 0.2082(2) 0.35824(18) 0.18916(10) 0.0269(3) Uani 1 1 d .
H11A H 0.1630 0.2885 0.1303 0.032 Uiso 1 1 calc R
H11B H 0.3059 0.4548 0.1937 0.032 Uiso 1 1 calc R
C17 C 0.1940(2) 0.42059(19) 0.37168(11) 0.0194(3) Uani 1 1 d .
C14 C -0.1164(2) 0.1102(2) 0.34492(12) 0.0237(4) Uani 1 1 d .
H14 H -0.2199 0.0037 0.3363 0.028 Uiso 1 1 calc R
C15 C -0.0538(2) 0.2139(2) 0.44127(12) 0.0245(4) Uani 1 1 d .
H15 H -0.1161 0.1797 0.4973 0.029 Uiso 1 1 calc R
C18 C 0.3608(2) 0.58177(19) 0.38879(11) 0.0204(3) Uani 1 1 d .
C22 C 0.5945(2) 0.8852(2) 0.62510(12) 0.0253(4) Uani 1 1 d .
H22A H 0.4778 0.8889 0.6339 0.038 Uiso 1 1 calc R
H22B H 0.6984 0.9972 0.6430 0.038 Uiso 1 1 calc R
H22C H 0.6218 0.8121 0.6718 0.038 Uiso 1 1 calc R
C21 C 0.5724(2) 0.81985(19) 0.51231(12) 0.0229(4) Uani 1 1 d .
H21A H 0.5500 0.8951 0.4645 0.027 Uiso 1 1 calc R
H21B H 0.6875 0.8112 0.5029 0.027 Uiso 1 1 calc R
N5 N 0.02381(18) 0.93207(15) 0.00209(9) 0.0183(3) Uani 1 1 d .
N1 N 0.2726(2) 0.87293(17) 0.06996(12) 0.0292(4) Uani 1 1 d .
C4 C 0.1944(2) 0.97865(18) 0.05396(11) 0.0197(3) Uani 1 1 d .
H4 H 0.2681 1.0923 0.0821 0.024 Uiso 1 1 calc R
C3 C 0.4628(2) 0.9271(2) 0.12897(13) 0.0291(4) Uani 1 1 d .
H3A H 0.5198 1.0469 0.1519 0.044 Uiso 1 1 calc R
H3B H 0.5361 0.9022 0.0843 0.044 Uiso 1 1 calc R
H3C H 0.4617 0.8690 0.1908 0.044 Uiso 1 1 calc R
C2 C 0.1671(3) 0.6984(2) 0.02754(15) 0.0321(4) Uani 1 1 d .
H2A H 0.0457 0.6534 0.0482 0.048 Uiso 1 1 calc R
H2B H 0.2385 0.6382 0.0552 0.048 Uiso 1 1 calc R
H2C H 0.1457 0.6859 -0.0495 0.048 Uiso 1 1 calc R
N10 N 0.46810(18) 0.52329(16) 0.95132(9) 0.0211(3) Uani 1 1 d .
N6 N 0.20872(19) 0.42510(16) 0.81047(10) 0.0235(3) Uani 1 1 d .
C9 C 0.3092(2) 0.40814(19) 0.90147(11) 0.0205(3) Uani 1 1 d .
H9 H 0.2591 0.3063 0.9293 0.025 Uiso 1 1 calc R
C7 C 0.0561(3) 0.2804(2) 0.74548(13) 0.0317(4) Uani 1 1 d .
H7A H 0.1025 0.2401 0.6911 0.048 Uiso 1 1 calc R
H7B H -0.0433 0.3096 0.7120 0.048 Uiso 1 1 calc R
H7C H 0.0053 0.1934 0.7893 0.048 Uiso 1 1 calc R
C8 C 0.2926(2) 0.5689(2) 0.75812(12) 0.0258(4) Uani 1 1 d .
H8A H 0.3813 0.6640 0.8107 0.039 Uiso 1 1 calc R
H8B H 0.1936 0.5946 0.7196 0.039 Uiso 1 1 calc R
H8C H 0.3596 0.5454 0.7086 0.039 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C18 O20 C21 116.10(12) .
C14 C13 C12 121.57(14) .
C14 C13 H13 119.2 .
C12 C13 H13 119.2 .
N11 C12 C13 118.54(14) .
N11 C12 C17 123.70(15) .
C13 C12 C17 117.74(14) .
C15 C16 C17 121.86(14) .
C15 C16 H16 119.1 .
C17 C16 H16 119.1 .
C12 N11 H11A 120.0 .
C12 N11 H11B 120.0 .
H11A N11 H11B 120.0 .
C16 C17 C12 119.14(14) .
C16 C17 C18 120.28(13) .
C12 C17 C18 120.57(14) .
C13 C14 C15 120.68(15) .
C13 C14 H14 119.7 .
C15 C14 H14 119.7 .
C16 C15 C14 118.99(14) .
C16 C15 H15 120.5 .
C14 C15 H15 120.5 .
O19 C18 O20 121.62(14) .
O19 C18 C17 125.88(14) .
O20 C18 C17 112.50(12) .
C21 C22 H22A 109.5 .
C21 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C21 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
O20 C21 C22 106.85(12) .
O20 C21 H21A 110.4 .
C22 C21 H21A 110.4 .
O20 C21 H21B 110.4 .
C22 C21 H21B 110.4 .
H21A C21 H21B 108.6 .
C4 N5 N5 111.36(15) 2_575
C4 N1 C3 122.02(14) .
C4 N1 C2 120.80(14) .
C3 N1 C2 117.18(13) .
N5 C4 N1 122.86(14) .
N5 C4 H4 118.6 .
N1 C4 H4 118.6 .
N1 C3 H3A 109.5 .
N1 C3 H3B 109.5 .
H3A C3 H3B 109.5 .
N1 C3 H3C 109.5 .
H3A C3 H3C 109.5 .
H3B C3 H3C 109.5 .
N1 C2 H2A 109.5 .
N1 C2 H2B 109.5 .
H2A C2 H2B 109.5 .
N1 C2 H2C 109.5 .
H2A C2 H2C 109.5 .
H2B C2 H2C 109.5 .
C9 N10 N10 110.64(15) 2_667
C9 N6 C7 119.85(13) .
C9 N6 C8 119.78(13) .
C7 N6 C8 116.27(12) .
N10 C9 N6 123.02(14) .
N10 C9 H9 118.5 .
N6 C9 H9 118.5 .
N6 C7 H7A 109.5 .
N6 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
N6 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
N6 C8 H8A 109.5 .
N6 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
N6 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O19 C18 1.2194(19) .
O20 C18 1.3536(18) .
O20 C21 1.4507(19) .
C13 C14 1.373(2) .
C13 C12 1.416(2) .
C13 H13 0.9500 .
C12 N11 1.357(2) .
C12 C17 1.424(2) .
C16 C15 1.376(2) .
C16 C17 1.409(2) .
C16 H16 0.9500 .
N11 H11A 0.8800 .
N11 H11B 0.8800 .
C17 C18 1.471(2) .
C14 C15 1.401(2) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C22 C21 1.507(2) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
N5 C4 1.291(2) .
N5 N5 1.426(2) 2_575
N1 C4 1.349(2) .
N1 C3 1.441(2) .
N1 C2 1.451(2) .
C4 H4 0.9500 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
N10 C9 1.282(2) .
N10 N10 1.430(2) 2_667
N6 C9 1.3627(19) .
N6 C7 1.443(2) .
N6 C8 1.450(2) .
C9 H9 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C14 C13 C12 N11 179.01(14) .
C14 C13 C12 C17 0.5(2) .
C15 C16 C17 C12 1.3(2) .
C15 C16 C17 C18 -178.06(14) .
N11 C12 C17 C16 179.85(14) .
C13 C12 C17 C16 -1.7(2) .
N11 C12 C17 C18 -0.8(2) .
C13 C12 C17 C18 177.68(13) .
C12 C13 C14 C15 1.2(2) .
C17 C16 C15 C14 0.3(2) .
C13 C14 C15 C16 -1.6(2) .
C21 O20 C18 O19 2.1(2) .
C21 O20 C18 C17 -178.10(12) .
C16 C17 C18 O19 -176.03(15) .
C12 C17 C18 O19 4.6(2) .
C16 C17 C18 O20 4.16(19) .
C12 C17 C18 O20 -175.20(12) .
C18 O20 C21 C22 175.65(12) .
N5 N5 C4 N1 179.37(15) 2_575
C3 N1 C4 N5 -179.40(15) .
C2 N1 C4 N5 0.8(2) .
N10 N10 C9 N6 174.51(15) 2_667
C7 N6 C9 N10 165.13(15) .
C8 N6 C9 N10 8.7(2) .
