#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/46/2014621.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_2014621
loop_
_publ_author_name
'Xu, Ying'
'Li, Hong-Xi'
'Zhang, Wen-Hua'
'Zhang, Yong'
'Lang, Jian-Ping'
_publ_section_title
Di-μ-iodo-bis{[1,1'-methylenebis(3,5-dimethyl-1H-pyrazole-κN²)]copper(I)}
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m4
_journal_page_last               m6
_journal_paper_doi               10.1107/S0108270104028379
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Cu2 I2 (C11 H16 N4)2]'
_chemical_formula_moiety         'C22 H32 Cu2 I2 N8'
_chemical_formula_sum            'C22 H32 Cu2 I2 N8'
_chemical_formula_weight         789.44
_chemical_name_systematic
;
Di-μ-iodo-bis{[1,1'-methylenebis(3,5-dimethyl-4H-pyrazole)]copper(I)}
;
_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                 112.249(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.924(5)
_cell_length_b                   11.702(3)
_cell_length_c                   14.339(4)
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2783.6(13)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury CCD area-detector'
_diffrn_measurement_method       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  0.041
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15314
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.772
_exptl_absorpt_correction_T_max  0.8952
_exptl_absorpt_correction_T_min  0.3974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.05
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.11
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.11
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0416
_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)+(0.026P)²+13.432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                2742
_reflns_number_total             3187
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1589.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2014621
_cod_database_fobs_code          2014621
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
I1 0.19514(2) 0.36842(3) 0.36810(2) 0.03630(10) Uani . . 1.000 I
Cu1 0.32371(3) 0.28540(5) 0.50282(4) 0.0327(2) Uani . . 1.000 Cu
N1 0.4086(2) 0.4025(3) 0.5930(3) 0.0296(11) Uani . . 1.000 N
N2 0.4874(2) 0.3684(3) 0.6207(3) 0.0297(11) Uani . . 1.000 N
N3 0.4869(2) 0.2020(3) 0.5232(3) 0.0301(11) Uani . . 1.000 N
N4 0.4098(2) 0.2118(3) 0.4544(3) 0.0305(11) Uani . . 1.000 N
C1 0.3369(3) 0.5845(4) 0.5754(4) 0.0469(17) Uani . . 1.000 C
C2 0.4122(3) 0.5167(4) 0.5969(3) 0.0334(14) Uani . . 1.000 C
C3 0.4917(3) 0.5548(4) 0.6251(4) 0.0403(17) Uani . . 1.000 C
C4 0.5383(3) 0.4588(4) 0.6400(3) 0.0336(14) Uani . . 1.000 C
C5 0.6272(3) 0.4446(5) 0.6732(4) 0.0492(19) Uani . . 1.000 C
C6 0.5047(2) 0.2477(4) 0.6232(3) 0.0309(12) Uani . . 1.000 C
C7 0.6225(3) 0.1219(5) 0.5443(5) 0.0514(19) Uani . . 1.000 C
C8 0.5355(3) 0.1465(4) 0.4849(4) 0.0382(16) Uani . . 1.000 C
C9 0.4880(3) 0.1213(4) 0.3876(4) 0.0445(17) Uani . . 1.000 C
C10 0.4108(3) 0.1627(4) 0.3709(4) 0.0369(16) Uani . . 1.000 C
C11 0.3364(3) 0.1598(5) 0.2778(4) 0.0501(17) Uani . . 1.000 C
H1A 0.29840 0.53960 0.59390 0.0560 Uiso calc R 1.000 H
H1B 0.34970 0.65530 0.61490 0.0560 Uiso calc R 1.000 H
H1C 0.31310 0.60320 0.50350 0.0560 Uiso calc R 1.000 H
H3 0.50970 0.63180 0.63250 0.0480 Uiso calc R 1.000 H
H5A 0.63890 0.37380 0.64500 0.0590 Uiso calc R 1.000 H
H5B 0.64960 0.50970 0.64960 0.0590 Uiso calc R 1.000 H
H5C 0.65140 0.44110 0.74700 0.0590 Uiso calc R 1.000 H
H6A 0.56230 0.23470 0.66490 0.0370 Uiso calc R 1.000 H
H6B 0.47220 0.20650 0.65500 0.0370 Uiso calc R 1.000 H
H7A 0.63130 0.11380 0.61570 0.0620 Uiso calc R 1.000 H
H7B 0.63780 0.05080 0.52000 0.0620 Uiso calc R 1.000 H
H7C 0.65550 0.18490 0.53610 0.0620 Uiso calc R 1.000 H
H9 0.50430 0.08290 0.34010 0.0530 Uiso calc R 1.000 H
H11A 0.30330 0.22700 0.27600 0.0610 Uiso calc R 1.000 H
H11B 0.35110 0.16000 0.21860 0.0610 Uiso calc R 1.000 H
H11C 0.30580 0.09030 0.27760 0.0610 Uiso calc R 1.000 H
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
Cu1 I1 Cu1 . 7_556 62.69(2) yes
I1 Cu1 N1 . . 116.88(10) yes
I1 Cu1 N4 . . 117.89(11) yes
I1 Cu1 I1 . 7_556 117.31(2) yes
N1 Cu1 N4 . . 91.12(15) yes
I1 Cu1 N1 7_556 . 105.32(11) yes
I1 Cu1 N4 7_556 . 104.60(10) yes
Cu1 N1 N2 . . 114.6(3) yes
Cu1 N1 C2 . . 133.8(3) yes
N2 N1 C2 . . 104.5(4) yes
N1 N2 C4 . . 111.8(4) yes
N1 N2 C6 . . 118.6(3) yes
C4 N2 C6 . . 129.6(4) yes
N4 N3 C6 . . 117.9(4) yes
N4 N3 C8 . . 112.1(4) yes
C6 N3 C8 . . 130.0(4) yes
Cu1 N4 N3 . . 117.7(3) yes
Cu1 N4 C10 . . 137.2(4) yes
N3 N4 C10 . . 105.0(4) yes
N1 C2 C1 . . 119.8(5) yes
N1 C2 C3 . . 111.0(4) yes
C1 C2 C3 . . 129.2(4) no
C2 C3 C4 . . 106.2(4) no
N2 C4 C3 . . 106.6(5) yes
N2 C4 C5 . . 122.3(4) yes
C3 C4 C5 . . 131.1(5) no
N2 C6 N3 . . 111.8(3) yes
N3 C8 C7 . . 123.5(5) yes
N3 C8 C9 . . 105.6(5) yes
C7 C8 C9 . . 130.8(5) no
C8 C9 C10 . . 107.1(5) no
N4 C10 C9 . . 110.1(5) yes
N4 C10 C11 . . 120.2(5) yes
C9 C10 C11 . . 129.7(5) no
C2 C1 H1A . . 109.00 no
C2 C1 H1B . . 110.00 no
C2 C1 H1C . . 110.00 no
H1A C1 H1B . . 109.00 no
H1A C1 H1C . . 109.00 no
H1B C1 H1C . . 109.00 no
C2 C3 H3 . . 127.00 no
C4 C3 H3 . . 127.00 no
C4 C5 H5A . . 109.00 no
C4 C5 H5B . . 109.00 no
C4 C5 H5C . . 109.00 no
H5A C5 H5B . . 110.00 no
H5A C5 H5C . . 110.00 no
H5B C5 H5C . . 109.00 no
N2 C6 H6A . . 109.00 no
N2 C6 H6B . . 109.00 no
N3 C6 H6A . . 109.00 no
N3 C6 H6B . . 109.00 no
H6A C6 H6B . . 108.00 no
C8 C7 H7A . . 110.00 no
C8 C7 H7B . . 109.00 no
C8 C7 H7C . . 109.00 no
H7A C7 H7B . . 109.00 no
H7A C7 H7C . . 109.00 no
H7B C7 H7C . . 109.00 no
C8 C9 H9 . . 126.00 no
C10 C9 H9 . . 126.00 no
C10 C11 H11A . . 109.00 no
C10 C11 H11B . . 109.00 no
C10 C11 H11C . . 109.00 no
H11A C11 H11B . . 110.00 no
H11A C11 H11C . . 109.00 no
H11B C11 H11C . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 Cu1 . . 2.5719(10) yes
I1 Cu1 . 7_556 2.6933(10) yes
Cu1 N1 . . 2.092(4) yes
Cu1 N4 . . 2.102(4) yes
N1 N2 . . 1.374(6) yes
N1 C2 . . 1.338(6) yes
N2 C4 . . 1.355(6) yes
N2 C6 . . 1.444(6) yes
N3 N4 . . 1.365(6) yes
N3 C6 . . 1.448(6) yes
N3 C8 . . 1.358(7) yes
N4 C10 . . 1.334(7) yes
C1 C2 . . 1.494(8) no
C2 C3 . . 1.399(8) no
C3 C4 . . 1.368(7) no
C4 C5 . . 1.490(8) no
C7 C8 . . 1.495(8) no
C8 C9 . . 1.363(8) no
C9 C10 . . 1.399(8) no
C10 C11 . . 1.488(8) no
C1 H1A . . 0.9800 no
C1 H1B . . 0.9800 no
C1 H1C . . 0.9800 no
C3 H3 . . 0.9500 no
C5 H5A . . 0.9800 no
C5 H5B . . 0.9800 no
C5 H5C . . 0.9800 no
C6 H6A . . 0.9900 no
C6 H6B . . 0.9900 no
C7 H7A . . 0.9800 no
C7 H7B . . 0.9800 no
C7 H7C . . 0.9800 no
C9 H9 . . 0.9500 no
C11 H11A . . 0.9800 no
C11 H11B . . 0.9800 no
C11 H11C . . 0.9800 no
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
_geom_hbond_publ_flag
C6 H6B I1 7_556 0.99 3.02 3.877(4) 145 yes
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu1 I1 Cu1 N1 7_556 . . -126.51(13) no
Cu1 I1 Cu1 N4 7_556 . . 126.46(12) no
Cu1 I1 Cu1 I1 7_556 . 7_556 0.02(8) no
Cu1 I1 Cu1 I1 . 7_556 7_556 -0.02(10) no
Cu1 I1 Cu1 N1 . 7_556 7_556 -131.98(11) no
Cu1 I1 Cu1 N4 . 7_556 7_556 132.73(11) no
I1 Cu1 N1 N2 . . . -145.6(3) no
I1 Cu1 N1 C2 . . . -0.5(5) no
N4 Cu1 N1 N2 . . . -23.3(3) no
N4 Cu1 N1 C2 . . . 121.8(5) no
I1 Cu1 N1 N2 7_556 . . 82.1(3) no
I1 Cu1 N1 C2 7_556 . . -132.8(4) no
I1 Cu1 N4 N3 . . . 159.1(2) no
I1 Cu1 N4 C10 . . . -25.4(5) no
N1 Cu1 N4 N3 . . . 37.6(3) no
N1 Cu1 N4 C10 . . . -146.9(5) no
I1 Cu1 N4 N3 7_556 . . -68.5(3) no
I1 Cu1 N4 C10 7_556 . . 107.0(5) no
Cu1 N1 N2 C4 . . . 154.0(3) no
Cu1 N1 N2 C6 . . . -24.6(5) no
C2 N1 N2 C4 . . . -0.8(5) no
C2 N1 N2 C6 . . . -179.4(4) no
Cu1 N1 C2 C1 . . . 35.1(7) no
Cu1 N1 C2 C3 . . . -146.6(4) no
N2 N1 C2 C1 . . . -177.4(4) no
N2 N1 C2 C3 . . . 0.9(5) no
N1 N2 C4 C3 . . . 0.3(5) no
N1 N2 C4 C5 . . . 178.9(4) no
C6 N2 C4 C3 . . . 178.7(4) no
C6 N2 C4 C5 . . . -2.7(7) no
N1 N2 C6 N3 . . . 77.7(5) no
C4 N2 C6 N3 . . . -100.7(5) no
C6 N3 N4 Cu1 . . . -2.8(5) no
C6 N3 N4 C10 . . . -179.6(4) no
C8 N3 N4 Cu1 . . . 175.9(3) no
C8 N3 N4 C10 . . . -0.9(5) no
N4 N3 C6 N2 . . . -58.9(5) no
C8 N3 C6 N2 . . . 122.6(5) no
N4 N3 C8 C7 . . . -178.8(4) no
N4 N3 C8 C9 . . . 0.9(5) no
C6 N3 C8 C7 . . . -0.3(8) no
C6 N3 C8 C9 . . . 179.4(4) no
Cu1 N4 C10 C9 . . . -175.3(3) no
Cu1 N4 C10 C11 . . . 5.6(7) no
N3 N4 C10 C9 . . . 0.6(5) no
N3 N4 C10 C11 . . . -178.6(4) no
C1 C2 C3 C4 . . . 177.3(4) no
N1 C2 C3 C4 . . . -0.7(5) no
C2 C3 C4 C5 . . . -178.2(5) no
C2 C3 C4 N2 . . . 0.2(5) no
N3 C8 C9 C10 . . . -0.5(5) no
C7 C8 C9 C10 . . . 179.2(5) no
C8 C9 C10 N4 . . . -0.1(6) no
C8 C9 C10 C11 . . . 179.0(5) no
