#------------------------------------------------------------------------------
#$Date: 2012-02-28 12:14:52 +0000 (Tue, 28 Feb 2012) $
#$Revision: 35911 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/16/8101674.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_8101674
loop_
_publ_author_name
'M. Kr\'olikowska'
'J. Garbarczyk'
_publ_section_title
;
 Crystal structures of 1,4-di(1-imidazolyl)butane dihydrochloride,
 (C10H16N4)Cl2, and 1,4-di(1-imidazolyl)butane dihydrate, C10H14N4
 · 2H2O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              103
_journal_volume                  220
_journal_year                    2005
_chemical_formula_sum            'C10 H16 Cl2 N4'
_chemical_formula_weight         263.17
_chemical_name_systematic
;
1,4-di(1-imidazolylbutane) dihydrochloride
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.98(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.915(3)
_cell_length_b                   8.230(2)
_cell_length_c                   10.189(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.0
_cell_measurement_theta_min      5.0
_cell_volume                     1295.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.389
_diffrn_measured_fraction_theta_max 0.389
_diffrn_measurement_device_type  KM-4
_diffrn_measurement_method       theta-2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1239
_diffrn_reflns_theta_full        79.76
_diffrn_reflns_theta_max         79.76
_diffrn_reflns_theta_min         6.09
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    4.349
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0047(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.122
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+0.2147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                1004
_reflns_number_total             1177
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    1267-1308.cff
_[local]_cod_data_source_block   DIBHCl
_[local]_cod_cif_authors_sg_H-M  C2/c
_cod_database_code               8101674
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_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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.12018(3) 0.14025(6) -0.00815(5) 0.0563(3) Uani 1 8 f d . . .
N1 N 0.12535(9) 0.30620(19) -0.48438(16) 0.0462(4) Uani 1 8 f d . . .
C2 C 0.10109(12) 0.2265(2) -0.3872(2) 0.0488(4) Uani 1 8 f d . . .
H2 H 0.0553(17) 0.159(3) -0.396(3) 0.066(7) Uiso 1 8 f d . . .
N3 N 0.15514(10) 0.2622(2) -0.27102(17) 0.0524(4) Uani 1 8 f d . . .
H3 H 0.1516(18) 0.222(3) -0.201(3) 0.070(8) Uiso 1 8 f d . . .
C4 C 0.21557(12) 0.3683(2) -0.2935(2) 0.0581(5) Uani 1 8 f d . . .
H4 H 0.2577 0.4069 -0.2261 0.070 Uiso 1 8 f d R . .
C5 C 0.19736(12) 0.3969(3) -0.4272(2) 0.0571(5) Uani 1 8 f d . . .
H5 H 0.2248 0.4609 -0.4813 0.087 Uiso 1 8 f d R . .
C6 C 0.08238(14) 0.2953(3) -0.6292(2) 0.0569(5) Uani 1 8 f d . . .
H6A H 0.0528 0.1931 -0.6473 0.080 Uiso 1 8 f d R . .
H6B H 0.1254 0.2999 -0.6809 0.080 Uiso 1 8 f d R . .
C7 C 0.01833(11) 0.43161(19) -0.67333(18) 0.0452(4) Uani 1 8 f d . . .
H7A H 0.0506 0.5360 -0.6432 0.062 Uiso 1 8 f d R . .
H7B H -0.0269 0.4197 -0.6226 0.058 Uiso 1 8 f d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0466(3) 0.0622(4) 0.0571(4) 0.01236(19) 0.0067(2) 0.00166(17)
N1 0.0410(8) 0.0490(8) 0.0443(8) 0.0010(6) 0.0017(6) 0.0055(6)
C2 0.0445(9) 0.0447(8) 0.0555(11) 0.0007(8) 0.0085(8) 0.0028(7)
N3 0.0541(9) 0.0542(9) 0.0471(10) 0.0044(7) 0.0086(7) 0.0108(7)
C4 0.0423(9) 0.0715(12) 0.0529(12) -0.0080(9) -0.0036(8) 0.0016(8)
C5 0.0455(10) 0.0649(11) 0.0591(12) 0.0001(9) 0.0094(8) -0.0074(8)
C6 0.0577(11) 0.0610(11) 0.0442(11) -0.0066(8) -0.0030(8) 0.0167(9)
C7 0.0442(9) 0.0451(9) 0.0426(11) -0.0030(7) 0.0033(7) 0.0007(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 108.46(16) . . ?
C2 N1 C6 124.91(17) . . ?
C5 N1 C6 126.62(18) . . ?
N3 C2 N1 108.50(17) . . ?
N3 C2 H2 124.0(16) . . ?
N1 C2 H2 127.5(16) . . ?
C2 N3 C4 109.06(17) . . ?
C2 N3 H3 122(2) . . ?
C4 N3 H3 128(2) . . ?
C5 C4 N3 107.19(18) . . ?
C5 C4 H4 130.9 . . ?
N3 C4 H4 121.9 . . ?
C4 C5 N1 106.79(18) . . ?
C4 C5 H5A 132.4 . . ?
N1 C5 H5A 120.8 . . ?
N1 C6 C7 111.76(15) . . ?
N1 C6 H6A 109.5 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C7 111.59(14) . 2_553 ?
C6 C7 H7A 106.5 . . ?
C7 C7 H7A 110.5 2_553 . ?
C6 C7 H7B 107.2 . . ?
C7 C7 H7B 112.9 2_553 . ?
H7A C7 H7B 107.9 . . ?
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
N1 C2 1.320(3) . ?
N1 C5 1.374(2) . ?
N1 C6 1.471(2) . ?
C2 N3 1.318(3) . ?
C2 H2A 0.90(3) . ?
N3 C4 1.359(3) . ?
N3 H3A 0.80(3) . ?
C4 C5 1.342(3) . ?
C4 H4A 0.8943 . ?
C5 H5A 0.9427 . ?
C6 C7 1.509(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C7 C7 1.530(3) 2_553 ?
C7 H7A 1.0102 . ?
C7 H7B 0.9869 . ?
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
C5 N1 C2 N3 -0.4(2) . . . . ?
C6 N1 C2 N3 178.55(16) . . . . ?
N1 C2 N3 C4 0.3(2) . . . . ?
C2 N3 C4 C5 -0.1(2) . . . . ?
N3 C4 C5 N1 -0.1(2) . . . . ?
C2 N1 C5 C4 0.3(2) . . . . ?
C6 N1 C5 C4 -178.61(17) . . . . ?
C2 N1 C6 C7 96.2(2) . . . . ?
C5 N1 C6 C7 -85.1(2) . . . . ?
N1 C6 C7 C7 173.32(16) . . . 2_553 ?