#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/35/2213508.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_2213508
loop_
_publ_author_name
'Adam D. Beitelman'
'Nathan A. Sieracki'
'Matthias Zeller'
'Gregory M. Ferrence'
_publ_section_title
;
 3,4,5-Trimethyl-1,2,4-triazole trihydrate
;
_journal_coeditor_code           PR2005
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2739
_journal_page_last               o2741
_journal_paper_doi               10.1107/S1600536807020235
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H9 N3, 3H2 O'
_chemical_formula_moiety         'C5 H9 N3, 3(H2 O)'
_chemical_formula_sum            'C5 H15 N3 O3'
_chemical_formula_weight         165.2
_chemical_name_systematic
;
3,4,5-Trimethyl-1,2,4-triazole trihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.1830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0587(4)
_cell_length_b                   6.5923(2)
_cell_length_c                   13.4209(5)
_cell_measurement_reflns_used    7270
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.68
_cell_measurement_theta_min      2.556
_cell_volume                     889.75(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae
et al.,  2006)
;
_computing_publication_material
'WinGX (Farrugia, 1999) and publCIF (Westrip, 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17695
_diffrn_reflns_theta_full        30.68
_diffrn_reflns_theta_max         30.68
_diffrn_reflns_theta_min         2.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.385
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         5341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1015P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                3958
_reflns_number_total             5341
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pr2005.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2213508
_cod_database_fobs_code          2213508
loop_
_symmetry_equiv_pos_as_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'
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
N N1 0.63048(7) 0.15687(10) 0.23095(5) 0.01905(16) Uani d . 1
N N2 0.73510(7) 0.15563(10) 0.16438(5) 0.02019(16) Uani d . 1
C C3 0.84600(8) 0.15397(11) 0.21729(6) 0.01866(17) Uani d . 1
N N4 0.81871(6) 0.15437(10) 0.31612(5) 0.01783(16) Uani d . 1
C C5 0.68335(8) 0.15592(11) 0.32118(6) 0.01763(17) Uani d . 1
C C6 0.98224(9) 0.15140(13) 0.17707(7) 0.0261(2) Uani d . 1
H H6A 0.9771 0.1462 0.1041 0.031 Uiso calc R 1
H H6B 1.03 0.0318 0.2023 0.031 Uiso calc R 1
H H6C 1.0297 0.2745 0.1982 0.031 Uiso calc R 1
C C7 0.91311(9) 0.15041(14) 0.39952(7) 0.0280(2) Uani d . 1
H H7A 0.8925 0.0363 0.4434 0.034 Uiso calc R 1
H H7B 0.9072 0.2777 0.4369 0.034 Uiso calc R 1
H H7C 1.0034 0.1346 0.3745 0.034 Uiso calc R 1
C C8 0.61061(9) 0.15678(13) 0.41608(6) 0.02398(19) Uani d . 1
H H8A 0.5147 0.1509 0.4018 0.029 Uiso calc R 1
H H8B 0.6316 0.2813 0.4531 0.029 Uiso calc R 1
H H8C 0.6374 0.0388 0.4561 0.029 Uiso calc R 1
O O1 0.76661(7) 0.44373(11) 0.85164(5) 0.02738(16) Uani d . 1
O O2 0.63598(6) 0.81171(9) 0.83098(5) 0.02416(16) Uani d . 1
O O3 0.72608(8) 0.09621(11) 0.95808(5) 0.03501(19) Uani d . 1
H H1A 0.7994(13) 0.406(2) 0.7918(11) 0.052(4) Uiso d . 1
H H1B 0.7267(13) 0.546(2) 0.8390(10) 0.048(4) Uiso d . 1
H H2A 0.5460(13) 0.8271(17) 0.8170(9) 0.041(3) Uiso d . 1
H H2B 0.6582(11) 0.9033(18) 0.8786(9) 0.033(3) Uiso d . 1
H H3A 0.7407(13) 0.221(2) 0.9294(9) 0.053(4) Uiso d . 1
H H3B 0.7076(17) 0.118(2) 1.0237(14) 0.081(5) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0195(3) 0.0203(3) 0.0174(3) -0.0005(2) -0.0002(2) 0.0010(2)
N2 0.0230(4) 0.0212(3) 0.0164(3) -0.0001(2) 0.0008(3) 0.0009(2)
C3 0.0216(4) 0.0160(3) 0.0184(4) -0.0012(3) 0.0016(3) 0.0005(3)
N4 0.0178(3) 0.0187(3) 0.0170(3) -0.0004(2) -0.0012(2) -0.0005(2)
C5 0.0184(4) 0.0166(3) 0.0179(4) -0.0003(3) -0.0001(3) -0.0001(3)
C6 0.0227(4) 0.0279(4) 0.0278(4) -0.0007(3) 0.0058(3) -0.0002(3)
C7 0.0231(4) 0.0393(5) 0.0213(4) 0.0022(3) -0.0063(3) -0.0028(3)
C8 0.0242(4) 0.0292(4) 0.0187(4) -0.0007(3) 0.0030(3) 0.0009(3)
O1 0.0315(3) 0.0277(3) 0.0230(3) 0.0034(3) 0.0016(2) 0.0033(2)
O2 0.0228(3) 0.0258(3) 0.0238(3) 0.0013(2) -0.0032(2) -0.0035(2)
O3 0.0596(5) 0.0273(4) 0.0179(3) -0.0080(3) -0.0035(3) -0.0004(3)
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 0 '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 0.006 '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
C5 N1 N2 107.12(7)
C3 N2 N1 107.35(7)
N2 C3 N4 109.99(7)
N2 C3 C6 125.85(7)
N4 C3 C6 124.16(8)
C3 N4 C5 105.68(7)
C3 N4 C7 127.54(7)
C5 N4 C7 126.77(7)
N1 C5 N4 109.86(7)
N1 C5 C8 126.52(7)
N4 C5 C8 123.62(7)
C3 C6 H6A 109.5
C3 C6 H6B 109.5
H6A C6 H6B 109.5
C3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N4 C7 H7A 109.5
N4 C7 H7B 109.5
H7A C7 H7B 109.5
N4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
H1A O1 H1B 103.3(12)
H2A O2 H2B 107.2(10)
H3A O3 H3B 107.3(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.3125(11)
N1 N2 1.3945(9)
N2 C3 1.3098(11)
C3 N4 1.3601(10)
C3 C6 1.4833(11)
N4 C5 1.3646(10)
N4 C7 1.4530(11)
C5 C8 1.4819(11)
C6 H6A 0.98
C6 H6B 0.98
C6 H6C 0.98
C7 H7A 0.98
C7 H7B 0.98
C7 H7C 0.98
C8 H8A 0.98
C8 H8B 0.98
C8 H8C 0.98
O1 H1A 0.908(14)
O1 H1B 0.800(15)
O2 H2A 0.926(14)
O2 H2B 0.904(13)
O3 H3A 0.923(15)
O3 H3B 0.915(18)
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
O2 H2B O3 1_565 0.904(13) 1.786(13) 2.6804(9) 169.6(10)
O3 H3A O1 . 0.923(15) 1.822(14) 2.7349(10) 169.7(12)
O2 H2A N1 3_666 0.926(14) 1.878(14) 2.7974(10) 171.2(11)
O1 H1A O2 2_646 0.908(14) 1.890(15) 2.7971(9) 176.4(13)
O3 H3B N2 1_556 0.915(18) 1.92(2) 2.7959(10) 159.9(16)
O1 H1B O2 . 0.800(15) 1.978(15) 2.7700(9) 170.3(14)
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
C5 N1 N2 C3 0.00(8)
N1 N2 C3 N4 -0.09(8)
N1 N2 C3 C6 179.74(7)
N2 C3 N4 C5 0.13(8)
C6 C3 N4 C5 -179.70(7)
N2 C3 N4 C7 179.17(7)
C6 C3 N4 C7 -0.66(12)
N2 N1 C5 N4 0.08(8)
N2 N1 C5 C8 179.96(7)
C3 N4 C5 N1 -0.13(8)
C7 N4 C5 N1 -179.17(7)
C3 N4 C5 C8 179.98(7)
C7 N4 C5 C8 0.94(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124624
