# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Trz
_database_code_depnum_ccdc_archive 'CCDC 1589636'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro' 'Universidad Nacional de La Plata, Argentina'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-(2-hydroxyphenyl)carbonyl-5-trifluoromethyl-2H-1,2,3-triazol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 F3 N3 O2'
_chemical_formula_weight         257.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.6999(3)
_cell_length_b                   20.5919(9)
_cell_length_c                   7.6340(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.377(5)
_cell_angle_gamma                90
_cell_volume                     1005.15(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1440
_cell_measurement_theta_min      3.7490
_cell_measurement_theta_max      28.6070
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_T_min  0.89566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.895
_oxdiff_exptl_absorpt_empirical_full_max 1.172
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            5024
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.966
_diffrn_reflns_theta_max         28.833
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2214
_reflns_number_gt                1740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.2080P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2214
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5126(2) 0.49822(7) 0.2455(2) 0.0307(4) Uani 1 1 d . . . . .
C2 C 0.6777(3) 0.54017(8) 0.2407(2) 0.0362(4) Uani 1 1 d . . . . .
C3 C 0.6345(3) 0.60330(9) 0.1752(3) 0.0458(5) Uani 1 1 d . . . . .
C4 C 0.4331(3) 0.62530(9) 0.1140(3) 0.0488(5) Uani 1 1 d . . . . .
C5 C 0.2690(3) 0.58483(10) 0.1139(3) 0.0512(5) Uani 1 1 d . . . . .
C6 C 0.3076(3) 0.52244(9) 0.1782(3) 0.0418(4) Uani 1 1 d . . . . .
C7 C 0.5605(2) 0.43229(8) 0.3164(2) 0.0298(3) Uani 1 1 d . . . . .
C8 C 0.4025(2) 0.38721(7) 0.3504(2) 0.0290(3) Uani 1 1 d . . . . .
C9 C 0.4307(2) 0.32198(8) 0.4080(2) 0.0295(3) Uani 1 1 d . . . . .
C10 C 0.6132(3) 0.27760(8) 0.4431(2) 0.0370(4) Uani 1 1 d . . . . .
N1 N 0.2544(2) 0.29958(7) 0.4308(2) 0.0384(3) Uani 1 1 d . . . . .
N2 N 0.1288(2) 0.35008(7) 0.3877(2) 0.0432(4) Uani 1 1 d . . . . .
N3 N 0.2059(2) 0.40339(7) 0.3395(2) 0.0389(4) Uani 1 1 d . . . . .
O1 O 0.88018(19) 0.52301(7) 0.2988(2) 0.0524(4) Uani 1 1 d . . . . .
O2 O 0.74025(16) 0.41053(6) 0.35585(18) 0.0420(3) Uani 1 1 d . . . . .
F1 F 0.77630(15) 0.29767(6) 0.58049(15) 0.0539(3) Uani 1 1 d . . . . .
F2 F 0.68332(16) 0.27149(5) 0.29746(16) 0.0535(3) Uani 1 1 d . . . . .
F3 F 0.56539(17) 0.21827(5) 0.48656(18) 0.0580(3) Uani 1 1 d . . . . .
H1O H 0.885(4) 0.4811(14) 0.332(4) 0.084(8) Uiso 1 1 d . . . . .
H2N H 0.003(4) 0.3498(11) 0.390(3) 0.063(6) Uiso 1 1 d . . . . .
H3 H 0.750(3) 0.6314(12) 0.176(3) 0.065(6) Uiso 1 1 d . . . . .
H4 H 0.403(3) 0.6684(11) 0.066(3) 0.055(6) Uiso 1 1 d . . . . .
H5 H 0.129(4) 0.5999(11) 0.069(3) 0.071(7) Uiso 1 1 d . . . . .
H6 H 0.191(3) 0.4947(10) 0.175(3) 0.047(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.406(2) . ?
C1 C2 1.412(2) . ?
C1 C7 1.461(2) . ?
C2 O1 1.343(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.367(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.372(3) . ?
C7 O2 1.2353(17) . ?
C7 C8 1.488(2) . ?
C8 N3 1.3371(18) . ?
C8 C9 1.408(2) . ?
C9 N1 1.3265(19) . ?
C9 C10 1.486(2) . ?
C10 F3 1.3300(19) . ?
C10 F1 1.334(2) . ?
C10 F2 1.336(2) . ?
N1 N2 1.317(2) . ?
N2 N3 1.3118(19) . ?

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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.41(15) . . ?
C6 C1 C7 123.18(14) . . ?
C2 C1 C7 119.40(14) . . ?
O1 C2 C3 116.44(16) . . ?
O1 C2 C1 123.53(15) . . ?
C3 C2 C1 120.03(16) . . ?
C4 C3 C2 120.67(18) . . ?
C3 C4 C5 120.37(18) . . ?
C6 C5 C4 120.01(18) . . ?
C5 C6 C1 121.48(18) . . ?
O2 C7 C1 121.16(14) . . ?
O2 C7 C8 115.08(14) . . ?
C1 C7 C8 123.75(13) . . ?
N3 C8 C9 107.13(13) . . ?
N3 C8 C7 124.93(14) . . ?
C9 C8 C7 127.86(13) . . ?
N1 C9 C8 109.34(13) . . ?
N1 C9 C10 118.65(14) . . ?
C8 C9 C10 132.00(13) . . ?
F3 C10 F1 106.86(14) . . ?
F3 C10 F2 106.97(14) . . ?
F1 C10 F2 105.93(13) . . ?
F3 C10 C9 111.30(13) . . ?
F1 C10 C9 112.82(14) . . ?
F2 C10 C9 112.55(14) . . ?
N2 N1 C9 102.73(13) . . ?
N3 N2 N1 117.06(13) . . ?
N2 N3 C8 103.73(13) . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -179.29(16) . . . . ?
C7 C1 C2 O1 -0.2(2) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
C7 C1 C2 C3 -179.34(15) . . . . ?
O1 C2 C3 C4 -179.65(17) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C7 C1 C6 C5 179.51(17) . . . . ?
C6 C1 C7 O2 172.10(16) . . . . ?
C2 C1 C7 O2 -7.0(2) . . . . ?
C6 C1 C7 C8 -9.2(2) . . . . ?
C2 C1 C7 C8 171.70(14) . . . . ?
O2 C7 C8 N3 171.19(15) . . . . ?
C1 C7 C8 N3 -7.6(2) . . . . ?
O2 C7 C8 C9 -5.2(2) . . . . ?
C1 C7 C8 C9 176.01(15) . . . . ?
N3 C8 C9 N1 0.13(18) . . . . ?
C7 C8 C9 N1 177.07(15) . . . . ?
N3 C8 C9 C10 179.55(16) . . . . ?
C7 C8 C9 C10 -3.5(3) . . . . ?
N1 C9 C10 F3 2.8(2) . . . . ?
C8 C9 C10 F3 -176.54(16) . . . . ?
N1 C9 C10 F1 -117.29(16) . . . . ?
C8 C9 C10 F1 63.3(2) . . . . ?
N1 C9 C10 F2 122.90(16) . . . . ?
C8 C9 C10 F2 -56.5(2) . . . . ?
C8 C9 N1 N2 0.01(18) . . . . ?
C10 C9 N1 N2 -179.50(14) . . . . ?
C9 N1 N2 N3 -0.2(2) . . . . ?
N1 N2 N3 C8 0.2(2) . . . . ?
C9 C8 N3 N2 -0.21(18) . . . . ?
C7 C8 N3 N2 -177.26(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N3 0.90(3) 2.67(3) 3.244(2) 123(2) 1_655
O1 H1O O2 0.90(3) 1.79(3) 2.5841(18) 147(2) .
N2 H2N O2 0.85(2) 2.11(2) 2.8294(18) 142(2) 1_455
N2 H2N F1 0.85(2) 2.62(2) 3.3139(19) 139.4(19) 1_455
N2 H2N F2 0.85(2) 2.60(2) 3.2822(18) 137.7(19) 1_455

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MeTrz
_database_code_depnum_ccdc_archive 'CCDC 1589638'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro' 'Universidad Nacional de La Plata, Argentina'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
4-(2-hydroxy-5-methylphenyl)carbonyl-5-trifluoromethyl-2H-1,2,3-triazol monohydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 F3 N3 O3'
_chemical_formula_weight         289.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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'

_cell_length_a                   7.4429(3)
_cell_length_b                   21.4011(9)
_cell_length_c                   15.5986(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.343(4)
_cell_angle_gamma                90
_cell_volume                     2464.26(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1916
_cell_measurement_theta_min      4.0270
_cell_measurement_theta_max      26.8920
_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.509
_exptl_crystal_size_mid          0.466
_exptl_crystal_size_min          0.366
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_T_min  0.89974
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.928
_oxdiff_exptl_absorpt_empirical_full_max 1.119
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            5772
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.054
_diffrn_reflns_theta_max         29.123
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2722
_reflns_number_gt                1998
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement. 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+1.8510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0065(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2722
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5472(3) 0.68900(9) 0.52319(12) 0.0416(4) Uani 1 1 d . . . . .
C2 C 0.5209(3) 0.75381(9) 0.52860(13) 0.0466(5) Uani 1 1 d . . . . .
C3 C 0.5815(3) 0.78495(10) 0.60430(15) 0.0565(6) Uani 1 1 d . . . . .
H3 H 0.5693 0.8281 0.6071 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6595(3) 0.75264(11) 0.67521(15) 0.0577(6) Uani 1 1 d . . . . .
H4 H 0.7001 0.7745 0.7255 0.069 Uiso 1 1 calc R U . . .
C5 C 0.6797(3) 0.68815(10) 0.67397(13) 0.0512(5) Uani 1 1 d . . . . .
C6 C 0.6251(3) 0.65753(9) 0.59761(12) 0.0453(5) Uani 1 1 d . . . . .
H6 H 0.6403 0.6145 0.5952 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4889(3) 0.65732(9) 0.44162(13) 0.0462(5) Uani 1 1 d . . . . .
C8 C 0.5349(3) 0.59110(9) 0.42588(12) 0.0427(5) Uani 1 1 d . . . . .
C9 C 0.4349(3) 0.54843(9) 0.37122(13) 0.0459(5) Uani 1 1 d . . . . .
C10 C 0.2525(3) 0.55311(12) 0.32079(18) 0.0629(6) Uani 1 1 d . . . . .
C11 C 0.7534(4) 0.65276(14) 0.75451(16) 0.0763(8) Uani 1 1 d . . . . .
H11A H 0.6594 0.6475 0.7907 0.114 Uiso 1 1 calc R U . . .
H11B H 0.8519 0.6758 0.7854 0.114 Uiso 1 1 calc R U . . .
H11C H 0.7957 0.6125 0.7387 0.114 Uiso 1 1 calc R U . . .
N1 N 0.5277(2) 0.49574(8) 0.36963(11) 0.0513(5) Uani 1 1 d . . . . .
N2 N 0.6780(3) 0.50737(8) 0.42063(11) 0.0505(5) Uani 1 1 d . . . . .
H2N H 0.7633 0.4802 0.4301 0.061 Uiso 1 1 calc R U . . .
N3 N 0.6907(3) 0.56337(7) 0.45657(11) 0.0494(5) Uani 1 1 d . . . . .
O1 O 0.4380(3) 0.78739(7) 0.46116(12) 0.0657(5) Uani 1 1 d . . . . .
O2 O 0.3995(3) 0.68428(7) 0.38061(11) 0.0704(5) Uani 1 1 d . . . . .
O1W O 0.9434(3) 0.42045(9) 0.44165(13) 0.0731(6) Uani 1 1 d . . . . .
F1 F 0.1341(2) 0.57831(10) 0.36538(14) 0.1079(7) Uani 1 1 d . . . . .
F2 F 0.2515(2) 0.58781(9) 0.25046(11) 0.0964(6) Uani 1 1 d . . . . .
F3 F 0.1912(2) 0.49853(9) 0.29267(16) 0.1217(9) Uani 1 1 d . . . . .
H1O H 0.409(4) 0.7609(15) 0.4191(18) 0.080(9) Uiso 1 1 d . . . . .
H1W H 1.047(5) 0.4271(16) 0.470(2) 0.103(12) Uiso 1 1 d . . . . .
H2W H 0.929(4) 0.3835(17) 0.440(2) 0.098(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.405(3) . ?
C1 C6 1.402(3) . ?
C1 C7 1.458(3) . ?
C2 O1 1.355(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.375(3) . ?
C5 C11 1.509(3) . ?
C7 O2 1.232(2) . ?
C7 C8 1.486(3) . ?
C8 N3 1.336(3) . ?
C8 C9 1.397(3) . ?
C9 N1 1.324(3) . ?
C9 C10 1.483(3) . ?
C10 F1 1.307(3) . ?
C10 F3 1.309(3) . ?
C10 F2 1.324(3) . ?
N1 N2 1.312(2) . ?
N2 N3 1.321(2) . ?

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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.08(18) . . ?
C2 C1 C7 118.90(17) . . ?
C6 C1 C7 123.00(17) . . ?
O1 C2 C3 118.32(19) . . ?
O1 C2 C1 122.00(19) . . ?
C3 C2 C1 119.68(19) . . ?
C4 C3 C2 120.4(2) . . ?
C3 C4 C5 121.7(2) . . ?
C6 C5 C4 117.74(19) . . ?
C6 C5 C11 121.2(2) . . ?
C4 C5 C11 121.0(2) . . ?
C5 C6 C1 122.25(19) . . ?
O2 C7 C1 121.82(18) . . ?
O2 C7 C8 115.59(18) . . ?
C1 C7 C8 122.59(17) . . ?
N3 C8 C9 107.37(17) . . ?
N3 C8 C7 124.91(18) . . ?
C9 C8 C7 127.46(18) . . ?
N1 C9 C8 109.25(18) . . ?
N1 C9 C10 119.45(18) . . ?
C8 C9 C10 131.27(18) . . ?
F1 C10 F3 108.4(2) . . ?
F1 C10 F2 106.1(2) . . ?
F3 C10 F2 104.9(2) . . ?
F1 C10 C9 112.3(2) . . ?
F3 C10 C9 112.0(2) . . ?
F2 C10 C9 112.7(2) . . ?
N2 N1 C9 103.51(16) . . ?
N1 N2 N3 115.99(16) . . ?
N2 N3 C8 103.86(16) . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -176.53(19) . . . . ?
C7 C1 C2 O1 2.1(3) . . . . ?
C6 C1 C2 C3 3.9(3) . . . . ?
C7 C1 C2 C3 -177.5(2) . . . . ?
O1 C2 C3 C4 177.4(2) . . . . ?
C1 C2 C3 C4 -3.0(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 2.6(3) . . . . ?
C3 C4 C5 C11 -175.5(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C11 C5 C6 C1 176.5(2) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C7 C1 C6 C5 179.8(2) . . . . ?
C2 C1 C7 O2 -8.3(3) . . . . ?
C6 C1 C7 O2 170.3(2) . . . . ?
C2 C1 C7 C8 170.84(19) . . . . ?
C6 C1 C7 C8 -10.6(3) . . . . ?
O2 C7 C8 N3 143.6(2) . . . . ?
C1 C7 C8 N3 -35.5(3) . . . . ?
O2 C7 C8 C9 -29.9(3) . . . . ?
C1 C7 C8 C9 151.0(2) . . . . ?
N3 C8 C9 N1 0.6(2) . . . . ?
C7 C8 C9 N1 175.1(2) . . . . ?
N3 C8 C9 C10 178.9(2) . . . . ?
C7 C8 C9 C10 -6.6(4) . . . . ?
N1 C9 C10 F1 134.4(2) . . . . ?
C8 C9 C10 F1 -43.8(4) . . . . ?
N1 C9 C10 F3 12.1(3) . . . . ?
C8 C9 C10 F3 -166.1(2) . . . . ?
N1 C9 C10 F2 -105.9(2) . . . . ?
C8 C9 C10 F2 75.9(3) . . . . ?
C8 C9 N1 N2 -0.8(2) . . . . ?
C10 C9 N1 N2 -179.4(2) . . . . ?
C9 N1 N2 N3 0.8(2) . . . . ?
N1 N2 N3 C8 -0.4(2) . . . . ?
C9 C8 N3 N2 -0.1(2) . . . . ?
C7 C8 N3 N2 -174.75(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 F1 0.93 2.58 3.399(3) 147.4 7_566
N2 H2N O1W 0.86 1.84 2.702(2) 175.7 .
O1 H1O O2 0.87(3) 1.74(3) 2.537(2) 150(3) .
O1W H1W N3 0.85(4) 2.15(4) 2.993(3) 176(3) 5_766
O1W H2W O1 0.80(4) 2.08(4) 2.865(2) 166(3) 3_545

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Petroleum ether : toluene in a 2 : 1 mixture '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1936976'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2019-06-27 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-(2-hydroxy-5-chlorophenyl)carbonyl-5-trifluoromethyl-2H-1,2,3-triazol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H5 Cl F3 N3 O2'
_chemical_formula_weight         291.62

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6403(9)
_cell_length_b                   8.1037(7)
_cell_length_c                   11.1004(13)
_cell_angle_alpha                106.450(9)
_cell_angle_beta                 101.623(11)
_cell_angle_gamma                93.168(9)
_cell_volume                     557.10(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1074
_cell_measurement_theta_min      3.9250
_cell_measurement_theta_max      26.6750
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.386
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_T_min  0.95290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.904
_oxdiff_exptl_absorpt_empirical_full_max 1.149
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4085
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.317
_diffrn_reflns_theta_max         28.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2373
_reflns_number_gt                1554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement. 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2373
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5822(4) 0.7811(3) 0.6307(2) 0.0353(6) Uani 1 1 d . . . . .
C2 C 0.7190(4) 0.8358(4) 0.5637(3) 0.0444(7) Uani 1 1 d . . . . .
C3 C 0.6500(5) 0.8190(4) 0.4328(3) 0.0548(8) Uani 1 1 d . . . . .
C4 C 0.4535(5) 0.7433(4) 0.3681(3) 0.0531(8) Uani 1 1 d . . . . .
C5 C 0.3222(4) 0.6816(3) 0.4321(3) 0.0448(7) Uani 1 1 d . . . . .
C6 C 0.3823(4) 0.7018(3) 0.5609(3) 0.0393(6) Uani 1 1 d . . . . .
C7 C 0.6505(4) 0.8065(3) 0.7682(2) 0.0341(6) Uani 1 1 d . . . . .
C8 C 0.5042(3) 0.7865(3) 0.8502(2) 0.0312(5) Uani 1 1 d . . . . .
C9 C 0.5487(3) 0.7535(3) 0.9691(2) 0.0316(5) Uani 1 1 d . . . . .
C10 C 0.7385(4) 0.7018(3) 1.0389(2) 0.0397(6) Uani 1 1 d . . . . .
N1 N 0.3803(3) 0.7652(3) 1.0182(2) 0.0404(5) Uani 1 1 d . . . . .
N2 N 0.2439(3) 0.8035(3) 0.9293(2) 0.0416(6) Uani 1 1 d . . . . .
N3 N 0.3067(3) 0.8173(3) 0.8261(2) 0.0392(5) Uani 1 1 d . . . . .
O1 O 0.9146(3) 0.9070(3) 0.6186(2) 0.0631(6) Uani 1 1 d . . . . .
O2 O 0.8343(2) 0.8516(2) 0.82585(17) 0.0446(5) Uani 1 1 d . . . . .
F1 F 0.8882(2) 0.8337(2) 1.09661(17) 0.0624(5) Uani 1 1 d . . . . .
F2 F 0.8200(2) 0.5840(2) 0.95894(16) 0.0556(5) Uani 1 1 d . . . . .
F3 F 0.6981(2) 0.6333(2) 1.12833(16) 0.0613(5) Uani 1 1 d . . . . .
Cl Cl 0.07778(12) 0.57812(12) 0.34712(8) 0.0697(3) Uani 1 1 d . . . . .
H1 H 0.936(5) 0.904(4) 0.693(3) 0.076(12) Uiso 1 1 d . . . . .
H2 H 0.106(4) 0.815(3) 0.937(3) 0.055(8) Uiso 1 1 d . . . . .
H3 H 0.740(5) 0.874(4) 0.395(3) 0.088(11) Uiso 1 1 d . . . . .
H4 H 0.417(5) 0.734(4) 0.281(3) 0.068(9) Uiso 1 1 d . . . . .
H6 H 0.292(4) 0.657(3) 0.606(3) 0.048(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.410(3) . ?
C1 C6 1.409(3) . ?
C1 C7 1.453(3) . ?
C2 O1 1.338(3) . ?
C2 C3 1.398(4) . ?
C3 C4 1.371(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.365(4) . ?
C5 Cl 1.735(3) . ?
C7 O2 1.239(3) . ?
C7 C8 1.491(3) . ?
C8 N3 1.337(3) . ?
C8 C9 1.396(3) . ?
C9 N1 1.336(3) . ?
C9 C10 1.488(3) . ?
C10 F1 1.334(3) . ?
C10 F3 1.330(3) . ?
C10 F2 1.328(3) . ?
N1 N2 1.317(3) . ?
N2 N3 1.325(3) . ?

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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.4(2) . . ?
C2 C1 C7 119.6(2) . . ?
C6 C1 C7 122.0(2) . . ?
O1 C2 C3 116.6(3) . . ?
O1 C2 C1 123.8(3) . . ?
C3 C2 C1 119.6(3) . . ?
C4 C3 C2 120.4(3) . . ?
C3 C4 C5 120.1(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 Cl 119.7(2) . . ?
C4 C5 Cl 119.5(2) . . ?
C5 C6 C1 120.5(2) . . ?
O2 C7 C1 122.0(2) . . ?
O2 C7 C8 115.5(2) . . ?
C1 C7 C8 122.5(2) . . ?
N3 C8 C9 108.1(2) . . ?
N3 C8 C7 123.6(2) . . ?
C9 C8 C7 127.9(2) . . ?
N1 C9 C8 109.3(2) . . ?
N1 C9 C10 119.5(2) . . ?
C8 C9 C10 131.1(2) . . ?
F1 C10 F3 107.7(2) . . ?
F1 C10 F2 105.8(2) . . ?
F3 C10 F2 107.2(2) . . ?
F1 C10 C9 113.0(2) . . ?
F3 C10 C9 111.51(19) . . ?
F2 C10 C9 111.3(2) . . ?
N2 N1 C9 102.6(2) . . ?
N1 N2 N3 117.0(2) . . ?
N2 N3 C8 103.1(2) . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -177.5(3) . . . . ?
C7 C1 C2 O1 2.0(4) . . . . ?
C6 C1 C2 C3 3.5(4) . . . . ?
C7 C1 C2 C3 -176.9(2) . . . . ?
O1 C2 C3 C4 178.3(3) . . . . ?
C1 C2 C3 C4 -2.7(4) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 2.9(4) . . . . ?
C3 C4 C5 Cl -177.3(2) . . . . ?
C4 C5 C6 C1 -2.0(4) . . . . ?
Cl C5 C6 C1 178.22(19) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C7 C1 C6 C5 179.3(2) . . . . ?
C2 C1 C7 O2 -10.7(4) . . . . ?
C6 C1 C7 O2 168.8(2) . . . . ?
C2 C1 C7 C8 167.0(2) . . . . ?
C6 C1 C7 C8 -13.4(4) . . . . ?
O2 C7 C8 N3 148.2(2) . . . . ?
C1 C7 C8 N3 -29.7(3) . . . . ?
O2 C7 C8 C9 -23.9(3) . . . . ?
C1 C7 C8 C9 158.2(2) . . . . ?
N3 C8 C9 N1 -0.4(3) . . . . ?
C7 C8 C9 N1 172.7(2) . . . . ?
N3 C8 C9 C10 175.9(2) . . . . ?
C7 C8 C9 C10 -11.0(4) . . . . ?
N1 C9 C10 F1 -106.5(3) . . . . ?
C8 C9 C10 F1 77.5(3) . . . . ?
N1 C9 C10 F3 15.1(3) . . . . ?
C8 C9 C10 F3 -161.0(2) . . . . ?
N1 C9 C10 F2 134.7(2) . . . . ?
C8 C9 C10 F2 -41.3(3) . . . . ?
C8 C9 N1 N2 0.1(3) . . . . ?
C10 C9 N1 N2 -176.7(2) . . . . ?
C9 N1 N2 N3 0.3(3) . . . . ?
N1 N2 N3 C8 -0.5(3) . . . . ?
C9 C8 N3 N2 0.6(2) . . . . ?
C7 C8 N3 N2 -172.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.81(3) 1.89(3) 2.614(3) 149(3) .
N2 H2 O2 0.94(3) 2.06(3) 2.825(3) 137(2) 1_455
N2 H2 F1 0.94(3) 2.48(3) 3.265(3) 141(2) 1_455
C6 H6 N3 0.97(3) 2.40(3) 2.980(3) 117.9(19) .

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ether:toluene (2:1)'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NitroTrz
_database_code_depnum_ccdc_archive 'CCDC 1589637'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro' 'Universidad Nacional de La Plata, Argentina'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-(2-hydroxy-5-nitrophenyl)carbonyl-5-trifluoromethyl-2H-1,2,3-triazol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H5 F3 N4 O4'
_chemical_formula_weight         302.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0192(2)
_cell_length_b                   17.4035(6)
_cell_length_c                   13.0726(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.057(4)
_cell_angle_gamma                90
_cell_volume                     1139.05(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1229
_cell_measurement_theta_min      4.4080
_cell_measurement_theta_max      24.7770
_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.146
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_T_min  0.93741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.864
_oxdiff_exptl_absorpt_empirical_full_max 1.107
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4851
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.337
_diffrn_reflns_theta_max         28.790
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2451
_reflns_number_gt                1630
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.3532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2451
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5368(4) 0.33217(14) 0.69008(17) 0.0400(6) Uani 1 1 d . . . . .
C2 C 0.7593(5) 0.32450(15) 0.76281(18) 0.0447(6) Uani 1 1 d . . . . .
C3 C 0.9127(6) 0.38843(17) 0.7931(2) 0.0542(7) Uani 1 1 d . . . . .
C4 C 0.8537(6) 0.45911(18) 0.7532(2) 0.0546(7) Uani 1 1 d . . . . .
C5 C 0.6356(5) 0.46665(14) 0.6828(2) 0.0485(6) Uani 1 1 d . . . . .
C6 C 0.4788(5) 0.40539(14) 0.6511(2) 0.0443(6) Uani 1 1 d . . . . .
C7 C 0.3844(5) 0.26316(14) 0.65872(19) 0.0443(6) Uani 1 1 d . . . . .
C8 C 0.1630(5) 0.26305(14) 0.57723(18) 0.0413(6) Uani 1 1 d . . . . .
C9 C 0.0330(5) 0.19907(14) 0.53199(19) 0.0434(6) Uani 1 1 d . . . . .
C10 C 0.0735(6) 0.11456(16) 0.5463(2) 0.0579(7) Uani 1 1 d . . . . .
N1 N 0.5689(6) 0.54251(14) 0.64173(19) 0.0611(7) Uani 1 1 d . . . . .
N2 N 0.0485(4) 0.32606(12) 0.53479(16) 0.0485(5) Uani 1 1 d . . . . .
N3 N -0.1361(5) 0.29805(15) 0.46903(18) 0.0528(6) Uani 1 1 d . . . . .
N4 N -0.1561(4) 0.22257(13) 0.46305(17) 0.0528(6) Uani 1 1 d . . . . .
O1 O 0.3552(5) 0.55123(13) 0.5931(2) 0.0887(8) Uani 1 1 d . . . . .
O2 O 0.7298(6) 0.59426(13) 0.6569(2) 0.0897(8) Uani 1 1 d . . . . .
O3 O 0.8347(4) 0.25720(12) 0.80478(15) 0.0587(5) Uani 1 1 d . . . . .
O4 O 0.4379(4) 0.20053(11) 0.69891(16) 0.0662(6) Uani 1 1 d . . . . .
F1 F 0.3227(3) 0.09287(10) 0.53824(15) 0.0751(6) Uani 1 1 d . . . . .
F2 F 0.0089(4) 0.09099(11) 0.63740(17) 0.0908(7) Uani 1 1 d . . . . .
F3 F -0.0761(4) 0.07585(11) 0.47620(19) 0.1027(8) Uani 1 1 d . . . . .
H3 H 1.069(6) 0.3810(17) 0.844(2) 0.063(8) Uiso 1 1 d . . . . .
H3N H -0.234(7) 0.326(2) 0.435(3) 0.089(12) Uiso 1 1 d . . . . .
H3O H 0.703(9) 0.220(3) 0.775(3) 0.114(14) Uiso 1 1 d . . . . .
H4 H 0.952(6) 0.500(2) 0.770(3) 0.076(10) Uiso 1 1 d . . . . .
H6 H 0.345(5) 0.4131(14) 0.6086(19) 0.037(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.396(3) . ?
C1 C2 1.421(3) . ?
C1 C7 1.467(3) . ?
C2 O3 1.337(3) . ?
C2 C3 1.395(4) . ?
C3 C4 1.360(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.371(4) . ?
C5 N1 1.455(3) . ?
C7 O4 1.231(3) . ?
C7 C8 1.484(3) . ?
C8 N2 1.340(3) . ?
C8 C9 1.400(3) . ?
C9 N4 1.326(3) . ?
C9 C10 1.495(4) . ?
C10 F1 1.317(3) . ?
C10 F2 1.322(3) . ?
C10 F3 1.326(3) . ?
N1 O1 1.217(3) . ?
N1 O2 1.216(3) . ?
N2 N3 1.312(3) . ?
N3 N4 1.319(3) . ?

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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.6(2) . . ?
C6 C1 C7 123.7(2) . . ?
C2 C1 C7 118.7(2) . . ?
O3 C2 C3 116.6(2) . . ?
O3 C2 C1 122.9(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 118.7(3) . . ?
C6 C5 C4 122.4(3) . . ?
C6 C5 N1 118.8(2) . . ?
C4 C5 N1 118.7(2) . . ?
C5 C6 C1 120.0(2) . . ?
O4 C7 C1 120.8(2) . . ?
O4 C7 C8 115.8(2) . . ?
C1 C7 C8 123.4(2) . . ?
N2 C8 C9 107.6(2) . . ?
N2 C8 C7 125.0(2) . . ?
C9 C8 C7 127.4(2) . . ?
N4 C9 C8 109.3(2) . . ?
N4 C9 C10 118.2(2) . . ?
C8 C9 C10 132.4(2) . . ?
F1 C10 F2 106.1(2) . . ?
F1 C10 F3 107.1(3) . . ?
F2 C10 F3 107.6(2) . . ?
F1 C10 C9 113.2(2) . . ?
F2 C10 C9 112.2(3) . . ?
F3 C10 C9 110.4(2) . . ?
O1 N1 O2 122.9(3) . . ?
O1 N1 C5 118.5(2) . . ?
O2 N1 C5 118.6(3) . . ?
N3 N2 C8 103.3(2) . . ?
N2 N3 N4 117.1(2) . . ?
N3 N4 C9 102.7(2) . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O3 -179.5(2) . . . . ?
C7 C1 C2 O3 -0.6(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 C1 C2 C3 178.7(2) . . . . ?
O3 C2 C3 C4 178.9(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 N1 178.7(3) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
N1 C5 C6 C1 -179.4(2) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C7 C1 C6 C5 -178.4(2) . . . . ?
C6 C1 C7 O4 -176.9(3) . . . . ?
C2 C1 C7 O4 4.2(4) . . . . ?
C6 C1 C7 C8 4.1(4) . . . . ?
C2 C1 C7 C8 -174.8(2) . . . . ?
O4 C7 C8 N2 169.7(2) . . . . ?
C1 C7 C8 N2 -11.2(4) . . . . ?
O4 C7 C8 C9 -9.1(4) . . . . ?
C1 C7 C8 C9 169.9(2) . . . . ?
N2 C8 C9 N4 0.3(3) . . . . ?
C7 C8 C9 N4 179.3(2) . . . . ?
N2 C8 C9 C10 178.9(3) . . . . ?
C7 C8 C9 C10 -2.1(5) . . . . ?
N4 C9 C10 F1 126.8(3) . . . . ?
C8 C9 C10 F1 -51.7(4) . . . . ?
N4 C9 C10 F2 -113.1(3) . . . . ?
C8 C9 C10 F2 68.4(4) . . . . ?
N4 C9 C10 F3 6.8(4) . . . . ?
C8 C9 C10 F3 -171.7(3) . . . . ?
C6 C5 N1 O1 10.9(4) . . . . ?
C4 C5 N1 O1 -168.4(3) . . . . ?
C6 C5 N1 O2 -168.6(3) . . . . ?
C4 C5 N1 O2 12.1(4) . . . . ?
C9 C8 N2 N3 -0.1(3) . . . . ?
C7 C8 N2 N3 -179.1(2) . . . . ?
C8 N2 N3 N4 -0.2(3) . . . . ?
N2 N3 N4 C9 0.3(3) . . . . ?
C8 C9 N4 N3 -0.4(3) . . . . ?
C10 C9 N4 N3 -179.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 N4 1.00(3) 2.70(3) 3.560(4) 145(2) 4_766
C3 H3 F3 1.00(3) 2.51(3) 3.439(3) 155(2) 4_766
N3 H3N O1 0.80(4) 2.25(4) 2.936(3) 145(4) 3_566
O3 H3O O2 0.99(5) 2.38(4) 2.902(3) 112(3) 2_646
O3 H3O O4 0.99(5) 1.64(4) 2.543(3) 150(4) .
C6 H6 N2 0.85(2) 2.29(2) 2.901(3) 129(2) .

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
