#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:05:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180411 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/80/7208071.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_7208071
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'
_chemical_formula_sum            'C6 H14 N4'
_chemical_formula_weight         142.21
_chemical_name_systematic
;
?
;
_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'
_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                 125.04(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.674(2)
_cell_length_b                   10.9232(13)
_cell_length_c                   8.796(2)
_cell_measurement_reflns_used    2186
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.2593
_cell_measurement_theta_min      2.8224
_cell_volume                     839.7(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3580
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95964
_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    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.112(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     49
_refine_ls_number_reflns         768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0524
_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)+(0.0752P)²+0.4162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                713
_reflns_number_total             768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25095k.txt
_cod_data_source_block           safin4n
_cod_original_cell_volume        839.8(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7208071
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
N5 N 0.22719(12) 0.20483(10) 0.03781(14) 0.0230(4) Uani 1 1 d .
C4 C 0.32117(15) 0.20054(12) 0.21547(18) 0.0236(4) Uani 1 1 d .
H4 H 0.4036 0.2572 0.2761 0.028 Uiso 1 1 calc R
N1 N 0.30650(14) 0.11766(11) 0.31929(16) 0.0322(5) Uani 1 1 d .
C2 C 0.39985(17) 0.12757(14) 0.51931(18) 0.0329(5) Uani 1 1 d .
H2A H 0.4900 0.1779 0.5601 0.049 Uiso 1 1 calc R
H2B H 0.4327 0.0458 0.5742 0.049 Uiso 1 1 calc R
H2C H 0.3402 0.1658 0.5593 0.049 Uiso 1 1 calc R
C3 C 0.17529(18) 0.03797(14) 0.2307(2) 0.0359(5) Uani 1 1 d .
H3A H 0.0829 0.0864 0.1855 0.054 Uiso 1 1 calc R
H3B H 0.1879 -0.0229 0.3204 0.054 Uiso 1 1 calc R
H3C H 0.1658 -0.0038 0.1260 0.054 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N5 0.0255(7) 0.0246(7) 0.0184(6) 0.0018(4) 0.0123(5) 0.0008(4)
C4 0.0243(7) 0.0245(7) 0.0209(8) -0.0001(5) 0.0123(6) 0.0005(5)
N1 0.0351(8) 0.0374(8) 0.0168(7) 0.0040(5) 0.0106(6) -0.0057(5)
C2 0.0365(9) 0.0392(9) 0.0187(8) 0.0039(6) 0.0133(7) 0.0040(6)
C3 0.0416(9) 0.0372(9) 0.0275(8) 0.0027(6) 0.0191(7) -0.0089(7)
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'
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
C4 N5 N5 110.86(13) 7
N5 C4 N1 122.11(12) .
N5 C4 H4 118.9 .
N1 C4 H4 118.9 .
C4 N1 C3 119.43(12) .
C4 N1 C2 120.27(12) .
C3 N1 C2 118.73(12) .
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 .
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 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N5 C4 1.2848(18) .
N5 N5 1.423(2) 7
C4 N1 1.3574(18) .
C4 H4 0.9500 .
N1 C3 1.4400(19) .
N1 C2 1.4447(18) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 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
N5 N5 C4 N1 -176.86(13) 7
N5 C4 N1 C3 -5.0(2) .
N5 C4 N1 C2 -170.55(12) .
