#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:39:48 +0100 (vie 25 de mar de 2016) $
#$Revision: 180090 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/36/7053639.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_7053639
loop_
_publ_author_name
'Barys, Maciej'
'Ciunik, Zbigniew'
'Drabent, Krzysztof'
'Kwiecień, Anna'
_publ_section_title
;
 Stable hemiaminals containing a triazole ring
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2605
_journal_paper_doi               10.1039/c0nj00346h
_journal_volume                  34
_journal_year                    2010
_chemical_formula_moiety         'C9 H8 N6 O5'
_chemical_formula_sum            'C9 H8 N6 O5'
_chemical_formula_weight         280.21
_chemical_name_common
(2,4-dinitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol
_chemical_name_systematic
;
(2,4-dinitrophenyl)(4H-1,2,4-triazole-4-ylamino)methanol
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.202(4)
_cell_length_b                   14.267(4)
_cell_length_c                   11.223(3)
_cell_measurement_reflns_used    3151
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      3.63
_cell_volume                     2274.0(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KM4-CCD
_diffrn_measurement_method       /w
_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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26651
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0556P)²+0.1991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                2488
_reflns_number_total             3151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0nj00346h.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pccn
_cod_database_code               7053639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
O1 O 1.14379(9) 0.72510(9) 0.55948(10) 0.0328(3) Uani 1 1 d
O2 O 1.00662(8) 0.66815(9) 0.59966(10) 0.0298(3) Uani 1 1 d
O3 O 1.39538(9) 0.52877(10) 0.92636(11) 0.0377(3) Uani 1 1 d
O4 O 1.39874(8) 0.54872(9) 0.73485(11) 0.0320(3) Uani 1 1 d
O14 O 0.92580(8) 0.63629(7) 0.94944(9) 0.0228(2) Uani 1 1 d
H41 H 0.8621(17) 0.6255(17) 0.9296(18) 0.053(7) Uiso 1 1 d
N1 N 0.75648(9) 0.87426(9) 0.86945(12) 0.0245(3) Uani 1 1 d
N2 N 0.76778(9) 0.87451(9) 0.74570(12) 0.0265(3) Uani 1 1 d
N3 N 0.89400(9) 0.81447(9) 0.82821(11) 0.0202(3) Uani 1 1 d
N4 N 0.98169(9) 0.76813(9) 0.83418(12) 0.0204(3) Uani 1 1 d
H40 H 1.0076(13) 0.7865(14) 0.8974(19) 0.031(5) Uiso 1 1 d
N5 N 1.08929(9) 0.68280(9) 0.62458(11) 0.0226(3) Uani 1 1 d
N6 N 1.35840(9) 0.54943(9) 0.83097(12) 0.0252(3) Uani 1 1 d
C1 C 1.06884(10) 0.62705(10) 0.83507(13) 0.0183(3) Uani 1 1 d
C2 C 1.12691(10) 0.64300(10) 0.73626(13) 0.0188(3) Uani 1 1 d
C3 C 1.22155(11) 0.62028(10) 0.73388(13) 0.0203(3) Uani 1 1 d
H3 H 1.2579(12) 0.6335(12) 0.6679(15) 0.018(4) Uiso 1 1 d
C4 C 1.25833(10) 0.57728(10) 0.83346(13) 0.0202(3) Uani 1 1 d
C5 C 1.20428(11) 0.55685(11) 0.93209(14) 0.0214(3) Uani 1 1 d
H5 H 1.2288(12) 0.5252(12) 0.9984(15) 0.023(4) Uiso 1 1 d
C6 C 1.10988(11) 0.58279(10) 0.93246(13) 0.0206(3) Uani 1 1 d
H6 H 1.0680(12) 0.5699(12) 0.9983(15) 0.022(4) Uiso 1 1 d
C14 C 0.96914(10) 0.66522(10) 0.84350(13) 0.0191(3) Uani 1 1 d
H14 H 0.9321(12) 0.6487(11) 0.7788(16) 0.019(4) Uiso 1 1 d
C1T C 0.83244(11) 0.83728(11) 0.91523(14) 0.0241(3) Uani 1 1 d
H1T H 0.8441(14) 0.8277(13) 0.9982(18) 0.036(5) Uiso 1 1 d
C2T C 0.85099(12) 0.83934(11) 0.72495(15) 0.0253(3) Uani 1 1 d
H2T H 0.8747(14) 0.8315(14) 0.6506(17) 0.033(5) Uiso 1 1 d
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C14 O14 H41 105.6(13)
C1T N1 N2 107.27(13)
C2T N2 N1 106.28(13)
C1T N3 C2T 105.26(13)
C1T N3 N4 130.51(13)
C2T N3 N4 124.06(13)
N3 N4 C14 111.17(11)
N3 N4 H40 106.3(13)
C14 N4 H40 107.5(13)
O1 N5 O2 123.66(13)
O1 N5 C2 117.90(12)
O2 N5 C2 118.36(12)
O4 N6 O3 124.56(14)
O4 N6 C4 118.07(13)
O3 N6 C4 117.37(13)
C6 C1 C2 116.70(13)
C6 C1 C14 120.29(13)
C2 C1 C14 122.66(13)
C3 C2 C1 123.34(14)
C3 C2 N5 115.18(13)
C1 C2 N5 121.44(13)
C4 C3 C2 117.20(14)
C4 C3 H3 122.0(10)
C2 C3 H3 120.8(10)
C3 C4 C5 122.31(14)
C3 C4 N6 118.01(13)
C5 C4 N6 119.64(13)
C4 C5 C6 118.88(14)
C4 C5 H5 122.2(10)
C6 C5 H5 118.9(10)
C1 C6 C5 121.51(14)
C1 C6 H6 115.5(10)
C5 C6 H6 123.0(10)
O14 C14 N4 113.86(12)
O14 C14 C1 110.89(12)
N4 C14 C1 103.79(11)
O14 C14 H14 109.9(10)
N4 C14 H14 105.3(10)
C1 C14 H14 112.9(10)
N1 C1T N3 110.33(14)
N1 C1T H1T 125.7(12)
N3 C1T H1T 123.9(12)
N2 C2T N3 110.84(14)
N2 C2T H2T 123.3(13)
N3 C2T H2T 125.9(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.2235(17)
O2 N5 1.2250(17)
O3 N6 1.2283(18)
O4 N6 1.2215(17)
O14 C14 1.4010(18)
O14 H41 0.94(2)
N1 C1T 1.306(2)
N1 N2 1.3980(19)
N2 C2T 1.305(2)
N3 C1T 1.351(2)
N3 C2T 1.357(2)
N3 N4 1.4117(17)
N4 C14 1.4826(19)
N4 H40 0.84(2)
N5 C2 1.4761(19)
N6 C4 1.476(2)
C1 C6 1.390(2)
C1 C2 1.401(2)
C1 C14 1.520(2)
C2 C3 1.383(2)
C3 C4 1.378(2)
C3 H3 0.922(17)
C4 C5 1.378(2)
C5 C6 1.391(2)
C5 H5 0.938(17)
C6 H6 0.966(17)
C14 H14 0.927(17)
C1T H1T 0.95(2)
C2T H2T 0.907(19)
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
C1T N1 N2 C2T -1.31(17)
C1T N3 N4 C14 79.85(19)
C2T N3 N4 C14 -94.67(17)
C6 C1 C2 C3 -2.5(2)
C14 C1 C2 C3 170.65(14)
C6 C1 C2 N5 175.26(13)
C14 C1 C2 N5 -11.6(2)
O1 N5 C2 C3 -27.43(19)
O2 N5 C2 C3 149.35(14)
O1 N5 C2 C1 154.64(14)
O2 N5 C2 C1 -28.6(2)
C1 C2 C3 C4 2.0(2)
N5 C2 C3 C4 -175.89(13)
C2 C3 C4 C5 0.2(2)
C2 C3 C4 N6 177.86(13)
O4 N6 C4 C3 -14.0(2)
O3 N6 C4 C3 165.78(14)
O4 N6 C4 C5 163.70(14)
O3 N6 C4 C5 -16.5(2)
C3 C4 C5 C6 -1.8(2)
N6 C4 C5 C6 -179.38(13)
C2 C1 C6 C5 0.8(2)
C14 C1 C6 C5 -172.50(14)
C4 C5 C6 C1 1.2(2)
N3 N4 C14 O14 -65.37(16)
N3 N4 C14 C1 173.96(12)
C6 C1 C14 O14 -9.13(19)
C2 C1 C14 O14 177.95(13)
C6 C1 C14 N4 113.52(15)
C2 C1 C14 N4 -59.40(17)
N2 N1 C1T N3 0.99(17)
C2T N3 C1T N1 -0.30(18)
N4 N3 C1T N1 -175.60(14)
N1 N2 C2T N3 1.15(18)
C1T N3 C2T N2 -0.57(18)
N4 N3 C2T N2 175.12(13)
