#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228243.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_2228243
loop_
_publ_author_name
'Xin, Jian-Hua'
'Tong, Xiao-Lan'
_publ_section_title
;
 5,5'-(Butane-1,4-diyl)bis(1H-tetrazole) dihydrate
;
_journal_coeditor_code           BT5418
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3328
_journal_paper_doi               10.1107/S1600536810048993
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H10 N8, 2H2 O'
_chemical_formula_moiety         'C6 H10 N8, 2(H2 O)'
_chemical_formula_sum            'C6 H14 N8 O2'
_chemical_formula_weight         230.25
_chemical_name_systematic
;
5,5'-(Butane-1,4-diyl)bis(1H-tetrazole) dihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.716(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.994(3)
_cell_length_b                   11.590(5)
_cell_length_c                   14.097(6)
_cell_measurement_reflns_used    1178
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.94
_cell_volume                     1122.8(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2756
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0517
_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)+(0.0759P)²+0.9248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                722
_reflns_number_total             992
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5418.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2228243
_cod_database_fobs_code          2228243
loop_
_symmetry_equiv_pos_as_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'
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_disorder_assembly
_atom_site_disorder_group
O O1W 0.2175(3) 0.10913(15) 0.88483(13) 0.0697(7) Uani d . 1 . .
H H1WA 0.2503 0.0847 0.9424 0.105 Uiso d R 1 . .
H H1WB 0.2153 0.1823 0.8886 0.105 Uiso d R 1 . .
N N1 0.2521(3) -0.00531(16) 0.72515(14) 0.0487(6) Uani d . 1 . .
H H1 0.2430 0.0355 0.7751 0.058 Uiso calc R 1 . .
N N2 0.2517(4) -0.11987(17) 0.72219(16) 0.0607(7) Uani d . 1 . .
N N3 0.2679(4) -0.14652(18) 0.63566(16) 0.0624(7) Uani d . 1 . .
N N4 0.2787(4) -0.05060(17) 0.58246(14) 0.0536(7) Uani d . 1 . .
C C1 0.2683(4) 0.0365(2) 0.63995(16) 0.0422(6) Uani d . 1 . .
C C3 0.2750(4) 0.1611(2) 0.61690(17) 0.0505(7) Uani d . 1 . .
H H3A 0.3991 0.1922 0.6488 0.061 Uiso calc R 1 . .
H H3B 0.1737 0.2006 0.6428 0.061 Uiso calc R 1 . .
C C4 0.2488(4) 0.1863(2) 0.50977(17) 0.0463(7) Uani d . 1 . .
H H4A 0.3525 0.1493 0.4838 0.056 Uiso calc R 1 . .
H H4B 0.1261 0.1541 0.4771 0.056 Uiso calc R 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
O1W 0.131(2) 0.0449(11) 0.0368(11) 0.0010(11) 0.0256(11) -0.0017(8)
N1 0.0817(16) 0.0361(12) 0.0306(11) -0.0005(10) 0.0162(10) 0.0006(9)
N2 0.101(2) 0.0406(13) 0.0419(13) -0.0030(12) 0.0169(12) 0.0072(10)
N3 0.108(2) 0.0365(12) 0.0451(14) -0.0027(12) 0.0196(13) 0.0011(10)
N4 0.0960(18) 0.0327(11) 0.0344(11) -0.0022(11) 0.0181(11) 0.0010(9)
C1 0.0603(16) 0.0364(12) 0.0306(12) -0.0024(11) 0.0103(10) 0.0003(10)
C3 0.082(2) 0.0344(13) 0.0373(14) -0.0022(12) 0.0157(12) -0.0011(11)
C4 0.0661(16) 0.0366(13) 0.0373(13) -0.0007(12) 0.0120(11) 0.0020(10)
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'
O O 0.0106 0.0060 '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'
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
H1WA O1W H1WB . . 106.1 ?
C1 N1 N2 . . 109.8(2) ?
C1 N1 H1 . . 125.1 ?
N2 N1 H1 . . 125.1 ?
N3 N2 N1 . . 105.69(19) ?
N2 N3 N4 . . 110.7(2) ?
C1 N4 N3 . . 106.1(2) ?
N4 C1 N1 . . 107.7(2) ?
N4 C1 C3 . . 127.6(2) ?
N1 C1 C3 . . 124.7(2) ?
C1 C3 C4 . . 113.8(2) ?
C1 C3 H3A . . 108.8 ?
C4 C3 H3A . . 108.8 ?
C1 C3 H3B . . 108.8 ?
C4 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
C4 C4 C3 7_556 . 111.7(3) ?
C4 C4 H4A 7_556 . 109.3 ?
C3 C4 H4A . . 109.3 ?
C4 C4 H4B 7_556 . 109.3 ?
C3 C4 H4B . . 109.3 ?
H4A C4 H4B . . 108.0 ?
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
O1W H1WA . 0.8500 ?
O1W H1WB . 0.8500 ?
N1 C1 . 1.320(3) ?
N1 N2 . 1.328(3) ?
N1 H1 . 0.8600 ?
N2 N3 . 1.284(3) ?
N3 N4 . 1.351(3) ?
N4 C1 . 1.305(3) ?
C1 C3 . 1.482(3) ?
C3 C4 . 1.516(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C4 7_556 1.503(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
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
O1W H1WB N3 4_556 0.85 2.02 2.851(3) 165.2
O1W H1WA N4 6_556 0.85 1.99 2.822(3) 167.0
N1 H1 O1W . 0.86 1.80 2.662(3) 174.8
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(3) ?
N1 N2 N3 N4 . . . . 0.0(3) ?
N2 N3 N4 C1 . . . . 0.0(3) ?
N3 N4 C1 N1 . . . . 0.1(3) ?
N3 N4 C1 C3 . . . . 179.5(2) ?
N2 N1 C1 N4 . . . . -0.1(3) ?
N2 N1 C1 C3 . . . . -179.6(2) ?
N4 C1 C3 C4 . . . . 13.6(4) ?
N1 C1 C3 C4 . . . . -167.1(3) ?
C1 C3 C4 C4 . . . 7_556 178.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139080052
