#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/03/2230392.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_2230392
loop_
_publ_author_name
'Zhang, Yan-Hua'
'Tian, Da-Min'
_publ_section_title
;
 5-[4-(1H-Imidazol-1-yl)phenyl]-2H-tetrazole dihydrate
;
_journal_coeditor_code           JH2291
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1537
_journal_paper_doi               10.1107/S1600536811019647
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H8 N6, 2H2 O1'
_chemical_formula_moiety         'C10 H8 N6, 2(H2 O1)'
_chemical_formula_sum            'C10 H12 N6 O2'
_chemical_formula_weight         248.26
_chemical_name_systematic
;
5-[4-(1H-Imidazol-1-yl)phenyl]-2H-tetrazole dihydrate
;
_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                97.0110(10)
_cell_angle_beta                 90.8130(10)
_cell_angle_gamma                113.449(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4300(7)
_cell_length_b                   8.2285(9)
_cell_length_c                   10.2047(11)
_cell_measurement_reflns_used    1702
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      2.449
_cell_volume                     566.74(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2913
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.507
_refine_ls_extinction_coef       0.13(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0754
_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)+(0.1194P)²+0.5477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2431
_reflns_number_gt                1199
_reflns_number_total             1953
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2291.cif
_cod_data_source_block           I
_cod_database_code               2230392
_cod_database_fobs_code          2230392
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.2591(5) 0.1994(4) 0.1928(3) 0.0420(9) Uani d . 1 1 . .
N N2 0.2495(6) 0.0363(4) 0.1481(3) 0.0483(10) Uani d . 1 1 . .
H H2 0.2561 -0.0008 0.0665 0.058 Uiso calc R 1 1 . .
N N3 0.2288(6) -0.0589(5) 0.2440(3) 0.0499(10) Uani d . 1 1 . .
N N4 0.2239(6) 0.0414(4) 0.3577(3) 0.0457(10) Uani d . 1 1 . .
N N5 0.2568(4) 0.7806(4) 0.6934(3) 0.0329(8) Uani d . 1 1 . .
N N6 0.2612(5) 0.9372(4) 0.8813(3) 0.0447(10) Uani d . 1 1 . .
O O1 0.2945(8) 0.4108(6) -0.0073(4) 0.1116(18) Uani d . 1 1 . .
H H1A 0.2650 0.3229 0.0363 0.134 Uiso d R 1 1 . .
H H1C 0.4182 0.4705 -0.0013 0.134 Uiso d PR 0.50 1 A 1
H H1D 0.2401 0.4795 0.0231 0.134 Uiso d PR 0.50 1 B 2
O O2 0.1048(12) 0.6070(9) 0.0820(6) 0.183(3) Uani d . 1 1 . .
H H2A 0.2078 0.5941 0.0576 0.220 Uiso d PR 0.50 1 C 1
H H2C -0.0111 0.5894 0.0548 0.220 Uiso d PR 0.50 1 C 2
H H2D 0.1533 0.7067 0.1322 0.220 Uiso d R 1 1 . .
C C1 0.2426(5) 0.1985(5) 0.3235(3) 0.0320(9) Uani d . 1 1 . .
C C2 0.2436(5) 0.3498(5) 0.4159(3) 0.0304(9) Uani d . 1 1 . .
C C3 0.3121(6) 0.5229(5) 0.3835(3) 0.0377(10) Uani d . 1 1 . .
H H3 0.3556 0.5438 0.2997 0.045 Uiso calc R 1 1 . .
C C4 0.3163(6) 0.6638(5) 0.4737(4) 0.0367(10) Uani d . 1 1 . .
H H4A 0.3632 0.7788 0.4508 0.044 Uiso calc R 1 1 . .
C C5 0.2507(5) 0.6338(5) 0.5985(3) 0.0296(9) Uani d . 1 1 . .
C C6 0.1766(6) 0.4619(5) 0.6316(3) 0.0372(10) Uani d . 1 1 . .
H H6 0.1290 0.4413 0.7144 0.045 Uiso calc R 1 1 . .
C C7 0.1736(6) 0.3217(5) 0.5418(3) 0.0374(10) Uani d . 1 1 . .
H H7 0.1245 0.2067 0.5648 0.045 Uiso calc R 1 1 . .
C C8 0.2597(6) 0.7830(6) 0.8248(4) 0.0416(11) Uani d . 1 1 . .
H H8 0.2604 0.6911 0.8692 0.050 Uiso calc R 1 1 . .
C C9 0.2610(6) 1.0379(5) 0.7849(4) 0.0436(11) Uani d . 1 1 . .
H H9 0.2632 1.1526 0.7977 0.052 Uiso calc R 1 1 . .
C C10 0.2571(6) 0.9415(5) 0.6680(4) 0.0424(11) Uani d . 1 1 . .
H H10 0.2550 0.9768 0.5850 0.051 Uiso calc R 1 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . 104.1(3) ?
N3 N2 N1 . . 111.2(3) ?
N3 N2 H2 . . 124.4 ?
N1 N2 H2 . . 124.4 ?
N2 N3 N4 . . 108.3(3) ?
C1 N4 N3 . . 105.4(3) ?
C8 N5 C10 . . 107.3(3) ?
C8 N5 C5 . . 125.3(3) ?
C10 N5 C5 . . 127.4(3) ?
C8 N6 C9 . . 108.6(3) ?
H1A O1 H1C . . 110.2 ?
H1A O1 H1D . . 110.2 ?
H1C O1 H1D . . 108.5 ?
H2A O2 H2C . . 142.7 ?
H2A O2 H2D . . 101.7 ?
H2C O2 H2D . . 108.1 ?
N4 C1 N1 . . 111.1(3) ?
N4 C1 C2 . . 124.6(3) ?
N1 C1 C2 . . 124.3(3) ?
C3 C2 C7 . . 118.1(3) ?
C3 C2 C1 . . 122.3(3) ?
C7 C2 C1 . . 119.6(3) ?
C4 C3 C2 . . 121.0(3) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 119.9(3) ?
C3 C4 H4A . . 120.1 ?
C5 C4 H4A . . 120.1 ?
C6 C5 C4 . . 120.0(3) ?
C6 C5 N5 . . 119.9(3) ?
C4 C5 N5 . . 120.1(3) ?
C7 C6 C5 . . 120.0(3) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C2 . . 120.9(4) ?
C6 C7 H7 . . 119.6 ?
C2 C7 H7 . . 119.6 ?
N6 C8 N5 . . 109.1(3) ?
N6 C8 H8 . . 125.5 ?
N5 C8 H8 . . 125.5 ?
C10 C9 N6 . . 107.5(4) ?
C10 C9 H9 . . 126.2 ?
N6 C9 H9 . . 126.2 ?
C9 C10 N5 . . 107.5(3) ?
C9 C10 H10 . . 126.2 ?
N5 C10 H10 . . 126.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.337(5) ?
N1 C1 . 1.341(5) ?
N2 N3 . 1.300(5) ?
N2 H2 . 0.8600 ?
N3 N4 . 1.350(5) ?
N4 C1 . 1.335(5) ?
N5 C8 . 1.338(5) ?
N5 C10 . 1.379(5) ?
N5 C5 . 1.438(5) ?
N6 C8 . 1.324(5) ?
N6 C9 . 1.362(5) ?
O1 H1A . 0.8500 ?
O1 H1C . 0.8500 ?
O1 H1D . 0.8499 ?
O2 H2A . 0.8500 ?
O2 H2C . 0.8500 ?
O2 H2D . 0.8501 ?
C1 C2 . 1.465(5) ?
C2 C3 . 1.393(5) ?
C2 C7 . 1.403(5) ?
C3 C4 . 1.379(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.385(5) ?
C6 C7 . 1.375(5) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.343(5) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
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 H2D N2 1_565 0.85 2.50 3.235(7) 146
O2 H2D N3 1_565 0.85 1.98 2.823(7) 172
O2 H2C O1 2_565 0.85 2.15 2.994(9) 170
O2 H2A O1 . 0.85 1.92 2.629(9) 141
O1 H1D O2 2_565 0.85 2.55 2.994(9) 114
O1 H1D O2 . 0.85 1.78 2.629(9) 175
O1 H1C O1 2_665 0.85 1.96 2.806(11) 175
O1 H1A N1 . 0.85 1.99 2.790(5) 157
N2 H2 N6 1_544 0.86 1.90 2.758(5) 174
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 N3 . . . . -0.1(5) ?
N1 N2 N3 N4 . . . . 0.1(5) ?
N2 N3 N4 C1 . . . . 0.0(5) ?
N3 N4 C1 N1 . . . . -0.1(5) ?
N3 N4 C1 C2 . . . . 179.5(4) ?
N2 N1 C1 N4 . . . . 0.1(4) ?
N2 N1 C1 C2 . . . . -179.5(3) ?
N4 C1 C2 C3 . . . . 163.4(4) ?
N1 C1 C2 C3 . . . . -17.1(6) ?
N4 C1 C2 C7 . . . . -16.6(6) ?
N1 C1 C2 C7 . . . . 162.9(4) ?
C7 C2 C3 C4 . . . . 1.8(6) ?
C1 C2 C3 C4 . . . . -178.2(3) ?
C2 C3 C4 C5 . . . . -0.4(6) ?
C3 C4 C5 C6 . . . . -1.5(6) ?
C3 C4 C5 N5 . . . . 179.3(3) ?
C8 N5 C5 C6 . . . . 23.6(6) ?
C10 N5 C5 C6 . . . . -155.1(4) ?
C8 N5 C5 C4 . . . . -157.2(4) ?
C10 N5 C5 C4 . . . . 24.1(6) ?
C4 C5 C6 C7 . . . . 1.9(6) ?
N5 C5 C6 C7 . . . . -178.9(3) ?
C5 C6 C7 C2 . . . . -0.4(6) ?
C3 C2 C7 C6 . . . . -1.4(6) ?
C1 C2 C7 C6 . . . . 178.6(4) ?
C9 N6 C8 N5 . . . . -0.5(5) ?
C10 N5 C8 N6 . . . . 0.2(5) ?
C5 N5 C8 N6 . . . . -178.7(3) ?
C8 N6 C9 C10 . . . . 0.7(5) ?
N6 C9 C10 N5 . . . . -0.6(5) ?
C8 N5 C10 C9 . . . . 0.3(5) ?
C5 N5 C10 C9 . . . . 179.1(4) ?
