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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/10/01/1100152.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_1100152
loop_
_publ_author_name
'Mohammad Abul-Haj'
'Miguel Quiros'
'Juan M. Salas'
_publ_section_title
;
 Structure of the adduct of bis(2,2'biimidazole)copper(II) perchlorate
 with 4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-7-one
;
_journal_issue                   8
_journal_name_full               'Journal of Chemical Crystallography'
_journal_page_first              549
_journal_page_last               552
_journal_paper_doi               10.1023/B:JOCC.0000042024.70444.a0
_journal_volume                  34
_journal_year                    2004
_chemical_formula_sum            'C22 H20 Cl2 Cu N16 O10'
_chemical_formula_weight         802.98
_chemical_name_systematic
'bis(2,2'-biimidazole)copper(II) perchlorate bis(4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-7-one'
_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     heavy
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.690(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.666(2)
_cell_length_b                   11.7586(8)
_cell_length_c                   13.4808(9)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      20.1
_cell_measurement_theta_min      12.5
_cell_volume                     3028.8(5)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'STOE STADI4 4-circle-diffractometer'
_diffrn_measurement_method
; Scan width (omega) = 0.82 - 1.67, scan ratio 2theta:omega = 1.00
  I(Net) and sigma(I) from profile fitting (Clegg, 1981)
;
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_radiation_detector       'NaI(Tl) scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_polarisn_norm  90
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4407
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        7.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  0.7873
_exptl_absorpt_correction_T_min  0.5556
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
    Psi Scan Reflections used    Mu * R = 0.16
    H   K   L   2Theta   Chi   Imin/Imax
    0   0   2     6.2    70.5    0.668
    0   0   4    12.5    70.5    0.775
   -5   1   6    19.6    75.4    0.822
   -2   2   7    22.4    75.8    0.824
   -6   2   7    23.7    71.5    0.803
   -2   0   8    24.4    79.5    0.822
    0   0   8    25.1    70.5    0.831
   -2   0  10    30.8    77.7    0.832
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1628
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.934
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       0.0006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.0806
_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)+(0.0950P)²+20.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1905
_refine_ls_wR_factor_ref         0.2456
_reflns_number_gt                2586
_reflns_number_total             4407
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1100152
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.5000 0.59382(7) 0.2500 0.0420(3) Uani 1 2 d S . .
N1I N 0.4693(2) 0.7034(4) 0.1342(3) 0.0436(10) Uani 1 1 d . . .
C2I C 0.4703(3) 0.8171(5) 0.1108(4) 0.0570(15) Uani 1 1 d . . .
H2I H 0.4908 0.8744 0.1554 0.068 Uiso 1 1 d R . .
C3I C 0.4364(3) 0.8307(5) 0.0115(4) 0.0565(14) Uani 1 1 d . . .
H3I H 0.4288 0.8992 -0.0239 0.068 Uiso 1 1 d R . .
N4I N 0.4154(2) 0.7262(4) -0.0263(3) 0.0491(11) Uani 1 1 d . . .
H4I H 0.3934 0.7109 -0.0879 0.059 Uiso 1 1 d R . .
C5I C 0.4357(3) 0.6517(4) 0.0486(3) 0.0410(11) Uani 1 1 d . . .
C6I C 0.4302(3) 0.5303(4) 0.0526(3) 0.0398(10) Uani 1 1 d . . .
N7I N 0.4035(2) 0.4529(4) -0.0174(3) 0.0473(10) Uani 1 1 d . . .
H7I H 0.3830 0.4664 -0.0800 0.057 Uiso 1 1 d R . .
C8I C 0.4139(3) 0.3477(5) 0.0278(4) 0.0541(14) Uani 1 1 d . . .
H8I H 0.4003 0.2779 -0.0030 0.065 Uiso 1 1 d R . .
C9I C 0.4474(3) 0.3663(5) 0.1268(4) 0.0519(13) Uani 1 1 d . . .
H9I H 0.4609 0.3102 0.1761 0.062 Uiso 1 1 d R . .
N10I N 0.4586(2) 0.4808(4) 0.1424(3) 0.0436(10) Uani 1 1 d . . .
N1 N 0.3496(3) 0.6636(4) 0.2746(3) 0.0500(11) Uani 1 1 d . . .
C2 C 0.3352(3) 0.7598(5) 0.2229(4) 0.0522(13) Uani 1 1 d . . .
H2 H 0.3516 0.8296 0.2510 0.063 Uiso 1 1 d R . .
N3 N 0.2947(2) 0.7513(4) 0.1261(3) 0.0487(11) Uani 1 1 d . . .
C3A C 0.2822(3) 0.6411(4) 0.1182(4) 0.0425(11) Uani 1 1 d . . .
N4 N 0.2457(3) 0.5787(4) 0.0391(3) 0.0505(11) Uani 1 1 d . . .
H4 H 0.2262 0.6109 -0.0179 0.061 Uiso 1 1 d R . .
C5 C 0.2406(3) 0.4650(5) 0.0514(4) 0.0516(13) Uani 1 1 d . . .
H5 H 0.2137 0.4227 -0.0020 0.062 Uiso 1 1 d R . .
C6 C 0.2721(3) 0.4103(5) 0.1374(4) 0.0509(13) Uani 1 1 d . . .
H6 H 0.2671 0.3318 0.1406 0.061 Uiso 1 1 d R . .
C7 C 0.3124(3) 0.4686(4) 0.2244(4) 0.0445(11) Uani 1 1 d . . .
O7 O 0.3443(2) 0.4307(3) 0.3062(3) 0.0540(10) Uani 1 1 d . . .
N8 N 0.3141(2) 0.5860(3) 0.2051(3) 0.0406(9) Uani 1 1 d . . .
Cl Cl 0.36980(9) 0.08321(11) 0.22556(11) 0.0587(4) Uani 1 1 d D . .
O1P O 0.4155(3) 0.0096(5) 0.2966(4) 0.0690(17) Uiso 0.67 1 d PD A 1
O2P O 0.3056(3) 0.0194(6) 0.1810(5) 0.0760(18) Uiso 0.67 1 d PD A 1
O3P O 0.4021(4) 0.1129(6) 0.1435(5) 0.100(2) Uiso 0.67 1 d PD A 1
O4P O 0.3498(4) 0.1805(5) 0.2740(5) 0.0789(19) Uiso 0.67 1 d PD A 1
O1P' O 0.3857(6) 0.0016(8) 0.3076(7) 0.0690(17) Uiso 0.33 1 d PD A 2
O2P' O 0.2957(3) 0.0927(12) 0.1868(9) 0.0760(18) Uiso 0.33 1 d PD A 2
O3P' O 0.4034(6) 0.0532(10) 0.1457(7) 0.100(2) Uiso 0.33 1 d PD A 2
O4P' O 0.3950(7) 0.1942(6) 0.2661(9) 0.0789(19) Uiso 0.33 1 d PD A 2
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
N10I Cu N10I 96.4(2) . 2_655 ?
N10I Cu N1I 172.47(18) . 2_655 ?
N10I Cu N1I 82.30(17) . . ?
N1I Cu N1I 99.9(2) 2_655 . ?
C5I N1I C2I 106.0(4) . . ?
C5I N1I Cu 112.1(3) . . ?
C2I N1I Cu 141.9(4) . . ?
C3I C2I N1I 108.2(5) . . ?
C2I C3I N4I 107.3(5) . . ?
C5I N4I C3I 107.6(4) . . ?
N4I C5I N1I 110.9(5) . . ?
N4I C5I C6I 132.5(5) . . ?
N1I C5I C6I 116.6(4) . . ?
N7I C6I N10I 110.8(4) . . ?
N7I C6I C5I 132.6(4) . . ?
N10I C6I C5I 116.6(4) . . ?
C6I N7I C8I 108.1(4) . . ?
C9I C8I N7I 106.1(5) . . ?
C8I C9I N10I 109.4(5) . . ?
C6I N10I C9I 105.6(4) . . ?
C6I N10I Cu 112.3(3) . . ?
C9I N10I Cu 142.1(3) . . ?
C2 N1 N8 101.4(4) . . ?
N1 C2 N3 116.5(5) . . ?
C3A N3 C2 101.8(4) . . ?
N3 C3A N4 130.5(5) . . ?
N3 C3A N8 111.2(4) . . ?
N4 C3A N8 118.3(5) . . ?
C3A N4 C5 118.6(4) . . ?
C6 C5 N4 123.2(5) . . ?
C5 C6 C7 122.2(5) . . ?
O7 C7 N8 119.8(5) . . ?
O7 C7 C6 129.5(5) . . ?
N8 C7 C6 110.7(4) . . ?
C3A N8 N1 109.2(4) . . ?
C3A N8 C7 127.0(4) . . ?
N1 N8 C7 123.8(4) . . ?
O2P' Cl O3P' 110.8(4) . . ?
O4P Cl O1P 112.1(3) . . ?
O2P' Cl O1P' 110.4(4) . . ?
O3P' Cl O1P' 110.9(4) . . ?
O4P Cl O3P 112.2(3) . . ?
O1P Cl O3P 109.7(3) . . ?
O2P' Cl O4P' 107.1(8) . . ?
O3P' Cl O4P' 109.0(4) . . ?
O1P' Cl O4P' 108.4(4) . . ?
O4P Cl O2P 107.2(5) . . ?
O1P Cl O2P 107.8(3) . . ?
O3P Cl O2P 107.5(3) . . ?
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
Cu N10I 1.993(4) . ?
Cu N1I 2.004(4) . ?
N1I C5I 1.333(6) . ?
N1I C2I 1.374(7) . ?
C2I C3I 1.356(8) . ?
C3I N4I 1.357(7) . ?
N4I C5I 1.325(6) . ?
C5I C6I 1.433(7) . ?
C6I N7I 1.327(6) . ?
C6I N10I 1.340(6) . ?
N7I C8I 1.372(7) . ?
C8I C9I 1.359(7) . ?
C9I N10I 1.373(7) . ?
N1 C2 1.324(6) . ?
N1 N8 1.374(6) . ?
C2 N3 1.362(7) . ?
N3 C3A 1.319(7) . ?
C3A N4 1.352(6) . ?
C3A N8 1.355(6) . ?
N4 C5 1.354(7) . ?
C5 C6 1.342(7) . ?
C6 C7 1.426(7) . ?
C7 O7 1.217(6) . ?
C7 N8 1.406(6) . ?
Cl O4P 1.418(5) . ?
Cl O2P' 1.432(6) . ?
Cl O3P' 1.433(5) . ?
Cl O1P 1.438(4) . ?
Cl O1P' 1.442(5) . ?
Cl O3P 1.442(5) . ?
Cl O4P' 1.456(6) . ?
Cl O2P 1.469(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 N3 0.86 2.15 2.957(6) 155.3 7_565
N4I H4I O7 0.86 2.26 2.995(6) 143.9 6_565
N4I H4I O4P 0.86 2.25 2.911(8) 133.2 6_565
N4I H4I O4P' 0.86 2.27 2.887(11) 128.8 6_565
N7I H7I O7 0.86 1.96 2.752(6) 152.6 6_565
