#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/97/2219768.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_2219768
loop_
_publ_author_name
'Xiao, Jie'
'Wang, Wen Xiang'
'Zhao, Hong'
_publ_section_title
;
 5-Methyl-1-(3-nitrobenzyl)-1H-1,2,3-triazole-4-carboxylic acid
 monohydrate
;
_journal_coeditor_code           BH2192
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2085
_journal_paper_doi               10.1107/S1600536808030584
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H10 N4 O4, H2 O'
_chemical_formula_moiety         'C11 H10 N4 O4, H2 O'
_chemical_formula_sum            'C11 H12 N4 O5'
_chemical_formula_weight         280.25
_chemical_name_systematic
;
5-Methyl-1-(3-nitrobenzyl)-1H-1,2,3-triazole-4-carboxylic acid
monohydrate
;
_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                84.88(3)
_cell_angle_beta                 77.70(2)
_cell_angle_gamma                89.38(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1649(14)
_cell_length_b                   8.2064(16)
_cell_length_c                   11.281(2)
_cell_measurement_reflns_used    5670
_cell_measurement_temperature    293.1500
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.10
_cell_volume                     645.5(2)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω
_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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0524
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6749
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0639
_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)+(0.0847P)²+0.0594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1811
_reflns_number_gt                1824
_reflns_number_total             2959
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2192.cif
_cod_data_source_block           I
_cod_database_code               2219768
_cod_database_fobs_code          2219768
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.7354(3) -0.2576(3) 0.1023(2) 0.0489(6) Uani d U 1
C C2 0.8477(3) -0.1276(3) 0.13603(19) 0.0445(5) Uani d . 1
C C3 0.7947(3) 0.0281(3) 0.16613(19) 0.0453(5) Uani d . 1
C C4 0.6141(4) 0.1200(3) 0.1754(3) 0.0662(7) Uani d . 1
H H4A 0.5476 0.1149 0.2591 0.099 Uiso calc R 1
H H4B 0.5357 0.0725 0.1281 0.099 Uiso calc R 1
H H4C 0.6419 0.2321 0.1451 0.099 Uiso calc R 1
C C5 0.9906(4) 0.2546(3) 0.2222(2) 0.0552(6) Uani d . 1
H H5A 0.9527 0.3352 0.1637 0.066 Uiso calc R 1
H H5B 1.1266 0.2683 0.2166 0.066 Uiso calc R 1
C C6 0.8858(3) 0.2880(3) 0.3486(2) 0.0481(6) Uani d . 1
C C7 0.8471(3) 0.4501(3) 0.3709(2) 0.0490(6) Uani d . 1
H H7 0.8787 0.5334 0.3083 0.059 Uiso calc R 1
C C8 0.7616(3) 0.4858(3) 0.4866(2) 0.0525(6) Uani d . 1
C C9 0.7117(4) 0.3678(4) 0.5813(2) 0.0673(7) Uani d . 1
H H9 0.6549 0.3952 0.6589 0.081 Uiso calc R 1
C C10 0.7481(5) 0.2061(4) 0.5582(2) 0.0755(8) Uani d . 1
H H10 0.7139 0.1233 0.6209 0.091 Uiso calc R 1
C C11 0.8352(4) 0.1670(3) 0.4426(2) 0.0634(7) Uani d . 1
H H11 0.8597 0.0582 0.4282 0.076 Uiso calc R 1
N N1 1.0337(3) -0.1508(2) 0.14233(18) 0.0543(5) Uani d . 1
N N2 1.0999(3) -0.0190(2) 0.17513(19) 0.0584(6) Uani d . 1
N N3 0.9557(3) 0.0908(2) 0.18882(17) 0.0487(5) Uani d . 1
N N4 0.7247(3) 0.6596(3) 0.5081(3) 0.0710(7) Uani d . 1
O O1 0.8110(3) -0.3876(2) 0.07308(19) 0.0758(6) Uani d U 1
O O2 0.5593(3) -0.2220(3) 0.1079(2) 0.0867(7) Uani d U 1
H H2 0.506(8) -0.295(6) 0.091(5) 0.18(2) Uiso d . 1
O O3 0.7575(4) 0.7611(3) 0.4204(3) 0.1067(9) Uani d . 1
O O4 0.6635(3) 0.6915(3) 0.6118(2) 0.1040(8) Uani d . 1
O O1W 0.2862(2) 0.5822(2) 0.09151(18) 0.0707(6) Uani d . 1
H H1A 0.2667 0.5412 0.0287 0.106 Uiso d R 1
H H1B 0.1813 0.6510 0.1111 0.106 Uiso d R 1
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
O1 C1 O2 125.6(2)
O1 C1 C2 120.3(2)
O2 C1 C2 114.1(2)
N1 C2 C3 109.06(19)
N1 C2 C1 121.1(2)
C3 C2 C1 129.8(2)
N3 C3 C2 103.26(19)
N3 C3 C4 123.4(2)
C2 C3 C4 133.4(2)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N3 C5 C6 114.05(19)
N3 C5 H5A 108.7
C6 C5 H5A 108.7
N3 C5 H5B 108.7
C6 C5 H5B 108.7
H5A C5 H5B 107.6
C11 C6 C7 119.2(2)
C11 C6 C5 123.2(2)
C7 C6 C5 117.5(2)
C8 C7 C6 119.1(2)
C8 C7 H7 120.4
C6 C7 H7 120.4
C9 C8 C7 122.6(2)
C9 C8 N4 119.4(2)
C7 C8 N4 118.0(2)
C8 C9 C10 118.1(2)
C8 C9 H9 121.0
C10 C9 H9 121.0
C11 C10 C9 120.4(2)
C11 C10 H10 119.8
C9 C10 H10 119.8
C6 C11 C10 120.6(2)
C6 C11 H11 119.7
C10 C11 H11 119.7
N2 N1 C2 109.17(19)
N1 N2 N3 106.90(18)
C3 N3 N2 111.60(18)
C3 N3 C5 129.1(2)
N2 N3 C5 119.26(18)
O4 N4 O3 124.3(3)
O4 N4 C8 117.7(3)
O3 N4 C8 118.0(2)
C1 O2 H2 110(4)
H1B O1W H1A 102.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.230(3)
C1 O2 1.282(3)
C1 C2 1.467(3)
C2 N1 1.360(3)
C2 C3 1.380(3)
C3 N3 1.350(3)
C3 C4 1.479(3)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 N3 1.466(3)
C5 C6 1.510(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C11 1.377(3)
C6 C7 1.391(3)
C7 C8 1.374(3)
C7 H7 0.9300
C8 C9 1.366(4)
C8 N4 1.479(3)
C9 C10 1.386(4)
C9 H9 0.9300
C10 C11 1.385(4)
C10 H10 0.9300
C11 H11 0.9300
N1 N2 1.300(3)
N2 N3 1.356(3)
N4 O4 1.210(3)
N4 O3 1.219(3)
O2 H2 0.77(5)
O1W H1B 0.9349
O1W H1A 0.8483
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4A O4 2_666 0.96 2.52 3.267(3) 135 yes
O1W H1A O1 2_655 0.85 1.94 2.755(3) 160.5 yes
O1W H1B N1 1_465 0.93 1.95 2.846(3) 160.3 yes
C11 H11 O3 1_545 0.93 2.57 3.423(4) 153 yes
O2 H2 O1W 1_545 0.77(5) 1.88(5) 2.592(3) 153(6) yes
