#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/57/2215755.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_2215755
loop_
_publ_author_name
'Liu, Yu-Fen'
'Xia, Hai-Tao'
'Wang, Da-Qi'
'Yang, Shu-Ping'
_publ_section_title
;μ-Chlorido-bis({N-benzyl-N'-[2-(benzylamino)ethyl]ethane-1,2-diamine}chloridocopper(II))
 chloride
;
_journal_coeditor_code           BG2104
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2805
_journal_page_last               m2806
_journal_paper_doi               10.1107/S1600536807051434
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu2 Cl3 (C18 H25 N3)2] Cl'
_chemical_formula_moiety         'C36 H50 Cl3 Cu2 N6 +, Cl -'
_chemical_formula_sum            'C36 H50 Cl4 Cu2 N6'
_chemical_formula_weight         835.70
_chemical_name_systematic
;
μ-Chlorido-bis({N-benzyl-N'-[2-(benzylamino)ethyl]ethane-
1,2-diamine}chloridocopper(II))
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 113.926(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   25.584(3)
_cell_length_b                   7.4506(11)
_cell_length_c                   11.5739(15)
_cell_measurement_reflns_used    896
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.306
_cell_measurement_theta_min      2.87
_cell_volume                     2016.6(5)
_computing_cell_refinement       'SMART (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens 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  0.0556
_diffrn_reflns_av_sigmaI/netI    0.1450
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5224
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  0.8655
_exptl_absorpt_correction_T_min  0.7116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.400
_refine_ls_abs_structure_details 'Flack (1983), 1474 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0208P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                1758
_reflns_number_total             3398
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2104.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2215755
_cod_database_fobs_code          2215755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
Cu Cu1 -0.00397(4) 0.58358(18) 0.18416(10) 0.0507(3) Uani d . 1
Cl Cl1 -0.06597(8) 0.8020(3) 0.0790(2) 0.0635(7) Uani d . 1
Cl Cl2 0.0000 0.3784(4) 0.0000 0.0528(9) Uani d S 1
Cl Cl3 0.0000 0.7398(8) 0.5000 0.176(3) Uani d S 1
N N1 0.0678(2) 0.7293(9) 0.2071(6) 0.0408(18) Uani d . 1
H H1 0.0658 0.7572 0.1288 0.049 Uiso calc R 1
N N2 0.0526(3) 0.4103(10) 0.3005(6) 0.054(2) Uani d . 1
H H2 0.0581 0.3252 0.2501 0.065 Uiso calc R 1
N N3 -0.0622(3) 0.4348(10) 0.2208(7) 0.056(2) Uani d . 1
H H3 -0.0721 0.5016 0.2746 0.067 Uiso calc R 1
C C1 0.1169(3) 0.6147(12) 0.2676(8) 0.047(2) Uani d . 1
H H1A 0.1509 0.6873 0.3088 0.057 Uiso calc R 1
H H1B 0.1225 0.5401 0.2048 0.057 Uiso calc R 1
C C2 0.1072(3) 0.4948(11) 0.3664(8) 0.056(3) Uani d . 1
H H2A 0.1372 0.4053 0.3995 0.067 Uiso calc R 1
H H2B 0.1070 0.5667 0.4360 0.067 Uiso calc R 1
C C3 0.0265(4) 0.3159(13) 0.3769(8) 0.060(3) Uani d . 1
H H3A 0.0276 0.3921 0.4457 0.072 Uiso calc R 1
H H3B 0.0476 0.2069 0.4125 0.072 Uiso calc R 1
C C4 -0.0348(4) 0.2709(13) 0.2912(9) 0.062(3) Uani d . 1
H H4A -0.0357 0.1764 0.2327 0.074 Uiso calc R 1
H H4B -0.0551 0.2293 0.3411 0.074 Uiso calc R 1
C C5 0.0710(3) 0.8999(12) 0.2756(8) 0.057(3) Uani d . 1
H H5A 0.0680 0.8734 0.3547 0.068 Uiso calc R 1
H H5B 0.0386 0.9743 0.2256 0.068 Uiso calc R 1
C C6 0.1253(3) 1.0044(10) 0.3033(9) 0.048(2) Uani d . 1
C C7 0.1353(3) 1.0868(16) 0.2091(8) 0.060(2) Uani d . 1
H H7 0.1076 1.0810 0.1268 0.071 Uiso calc R 1
C C8 0.1848(4) 1.1774(12) 0.2322(11) 0.070(3) Uani d . 1
H H8 0.1906 1.2312 0.1658 0.084 Uiso calc R 1
C C9 0.2256(4) 1.1893(13) 0.3517(13) 0.080(4) Uani d . 1
H H9 0.2598 1.2489 0.3671 0.097 Uiso calc R 1
C C10 0.2165(4) 1.1132(16) 0.4498(10) 0.082(3) Uani d . 1
H H10 0.2443 1.1231 0.5319 0.098 Uiso calc R 1
C C11 0.1657(4) 1.0207(11) 0.4267(9) 0.066(3) Uani d . 1
H H11 0.1591 0.9707 0.4932 0.079 Uiso calc R 1
C C12 -0.1162(3) 0.3945(14) 0.1112(8) 0.071(3) Uani d . 1
H H12A -0.1071 0.3243 0.0511 0.086 Uiso calc R 1
H H12B -0.1327 0.5068 0.0703 0.086 Uiso calc R 1
C C13 -0.1609(3) 0.2938(14) 0.1405(9) 0.059(3) Uani d . 1
C C14 -0.1898(4) 0.3716(15) 0.2039(10) 0.088(3) Uani d . 1
H H14 -0.1802 0.4871 0.2360 0.105 Uiso calc R 1
C C15 -0.2333(5) 0.2800(17) 0.2209(11) 0.100(4) Uani d . 1
H H15 -0.2541 0.3371 0.2601 0.120 Uiso calc R 1
C C16 -0.2455(4) 0.1112(19) 0.1818(11) 0.094(4) Uani d . 1
H H16 -0.2737 0.0490 0.1965 0.113 Uiso calc R 1
C C17 -0.2171(4) 0.0308(14) 0.1209(11) 0.096(4) Uani d . 1
H H17 -0.2265 -0.0860 0.0914 0.116 Uiso calc R 1
C C18 -0.1744(4) 0.1184(18) 0.1018(10) 0.082(4) Uani d . 1
H H18 -0.1542 0.0591 0.0622 0.099 Uiso calc R 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'
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_site_symmetry_3
_geom_angle
N2 Cu1 N3 . 84.2(3)
N2 Cu1 N1 . 83.6(3)
N3 Cu1 N1 . 162.2(3)
N2 Cu1 Cl1 . 171.5(2)
N3 Cu1 Cl1 . 95.2(2)
N1 Cu1 Cl1 . 94.85(19)
N2 Cu1 Cl2 . 85.18(19)
N3 Cu1 Cl2 . 97.1(2)
N1 Cu1 Cl2 . 94.85(19)
Cl1 Cu1 Cl2 . 103.26(9)
N2 Cu1 Cl3 . 79.64(19)
N3 Cu1 Cl3 . 72.7(2)
N1 Cu1 Cl3 . 92.3(2)
Cl1 Cu1 Cl3 . 92.12(10)
Cl2 Cu1 Cl3 . 162.39(11)
Cu1 Cl2 Cu1 2 109.79(12)
C1 N1 C5 . 113.5(6)
C1 N1 Cu1 . 107.8(5)
C5 N1 Cu1 . 112.0(5)
C1 N1 H1 . 107.8
C5 N1 H1 . 107.8
Cu1 N1 H1 . 107.8
C2 N2 C3 . 117.9(7)
C2 N2 Cu1 . 110.9(6)
C3 N2 Cu1 . 109.3(5)
C2 N2 H2 . 106.0
C3 N2 H2 . 106.0
Cu1 N2 H2 . 106.0
C4 N3 C12 . 112.0(7)
C4 N3 Cu1 . 109.9(5)
C12 N3 Cu1 . 116.0(5)
C4 N3 H3 . 106.0
C12 N3 H3 . 106.0
Cu1 N3 H3 . 106.0
N1 C1 C2 . 109.4(6)
N1 C1 H1A . 109.8
C2 C1 H1A . 109.8
N1 C1 H1B . 109.8
C2 C1 H1B . 109.8
H1A C1 H1B . 108.2
N2 C2 C1 . 105.9(7)
N2 C2 H2A . 110.6
C1 C2 H2A . 110.6
N2 C2 H2B . 110.6
C1 C2 H2B . 110.6
H2A C2 H2B . 108.7
N2 C3 C4 . 108.2(7)
N2 C3 H3A . 110.1
C4 C3 H3A . 110.1
N2 C3 H3B . 110.1
C4 C3 H3B . 110.1
H3A C3 H3B . 108.4
N3 C4 C3 . 108.2(8)
N3 C4 H4A . 110.1
C3 C4 H4A . 110.1
N3 C4 H4B . 110.1
C3 C4 H4B . 110.1
H4A C4 H4B . 108.4
N1 C5 C6 . 113.8(7)
N1 C5 H5A . 108.8
C6 C5 H5A . 108.8
N1 C5 H5B . 108.8
C6 C5 H5B . 108.8
H5A C5 H5B . 107.7
C7 C6 C11 . 118.7(8)
C7 C6 C5 . 121.2(8)
C11 C6 C5 . 120.2(9)
C8 C7 C6 . 121.8(8)
C8 C7 H7 . 119.1
C6 C7 H7 . 119.1
C9 C8 C7 . 120.1(10)
C9 C8 H8 . 119.9
C7 C8 H8 . 119.9
C8 C9 C10 . 119.9(10)
C8 C9 H9 . 120.1
C10 C9 H9 . 120.1
C9 C10 C11 . 120.2(9)
C9 C10 H10 . 119.9
C11 C10 H10 . 119.9
C6 C11 C10 . 119.2(9)
C6 C11 H11 . 120.4
C10 C11 H11 . 120.4
N3 C12 C13 . 115.8(7)
N3 C12 H12A . 108.3
C13 C12 H12A . 108.3
N3 C12 H12B . 108.3
C13 C12 H12B . 108.3
H12A C12 H12B . 107.4
C14 C13 C18 . 117.3(9)
C14 C13 C12 . 122.2(10)
C18 C13 C12 . 120.5(9)
C13 C14 C15 . 120.6(10)
C13 C14 H14 . 119.7
C15 C14 H14 . 119.7
C16 C15 C14 . 120.6(11)
C16 C15 H15 . 119.7
C14 C15 H15 . 119.7
C15 C16 C17 . 119.9(11)
C15 C16 H16 . 120.1
C17 C16 H16 . 120.1
C16 C17 C18 . 120.8(12)
C16 C17 H17 . 119.6
C18 C17 H17 . 119.6
C17 C18 C13 . 120.8(10)
C17 C18 H18 . 119.6
C13 C18 H18 . 119.6
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
Cu1 N2 . 1.999(7) y
Cu1 N3 . 2.035(6) y
Cu1 N1 . 2.055(6) y
Cu1 Cl1 . 2.254(2) y
Cu1 Cl2 . 2.658(2) y
Cu1 Cl3 . 3.798(2) ?
Cl2 Cu1 2 2.658(2) ?
N1 C1 . 1.444(9) ?
N1 C5 . 1.482(9) ?
N1 H1 . 0.9100 ?
N2 C2 . 1.437(8) ?
N2 C3 . 1.483(9) ?
N2 H2 . 0.9100 ?
N3 C4 . 1.478(10) ?
N3 C12 . 1.478(8) ?
N3 H3 . 0.9100 ?
C1 C2 . 1.547(10) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.515(9) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.508(10) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.363(11) ?
C6 C11 . 1.388(10) ?
C7 C8 . 1.363(11) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.357(13) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.370(13) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.398(11) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.518(10) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.364(11) ?
C13 C18 . 1.379(15) ?
C14 C15 . 1.386(12) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.331(15) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.342(13) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.365(12) ?
C17 H17 . 0.9300 ?
C18 H18 . 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
C3 H3A Cl3 . 0.97 2.82 3.640(11) 142.6
C2 H2A Cg1 1_545 0.97 2.74 3.547(9) 141
C15 H15 Cg1 3_445 0.93 2.97 3.872(14) 163
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_4
_geom_torsion
N2 Cu1 Cl2 Cu1 2 -137.1(2)
N3 Cu1 Cl2 Cu1 2 139.3(2)
N1 Cu1 Cl2 Cu1 2 -53.97(18)
Cl1 Cu1 Cl2 Cu1 2 42.18(6)
Cl3 Cu1 Cl2 Cu1 2 -167.59(13)
N2 Cu1 N1 C1 . 12.1(5)
N3 Cu1 N1 C1 . 59.5(12)
Cl1 Cu1 N1 C1 . -176.2(5)
Cl2 Cu1 N1 C1 . -72.5(5)
Cl3 Cu1 N1 C1 . 91.4(5)
N2 Cu1 N1 C5 . -113.5(5)
N3 Cu1 N1 C5 . -66.1(11)
Cl1 Cu1 N1 C5 . 58.2(5)
Cl2 Cu1 N1 C5 . 161.9(5)
Cl3 Cu1 N1 C5 . -34.2(5)
N3 Cu1 N2 C2 . -149.5(6)
N1 Cu1 N2 C2 . 17.4(5)
Cl2 Cu1 N2 C2 . 112.9(5)
Cl3 Cu1 N2 C2 . -76.1(5)
N3 Cu1 N2 C3 . -17.9(5)
N1 Cu1 N2 C3 . 149.0(5)
Cl2 Cu1 N2 C3 . -115.6(5)
Cl3 Cu1 N2 C3 . 55.5(5)
N2 Cu1 N3 C4 . -9.3(6)
N1 Cu1 N3 C4 . -56.5(12)
Cl1 Cu1 N3 C4 . 179.2(5)
Cl2 Cu1 N3 C4 . 75.1(6)
Cl3 Cu1 N3 C4 . -90.2(5)
N2 Cu1 N3 C12 . -137.6(6)
N1 Cu1 N3 C12 . 175.1(8)
Cl1 Cu1 N3 C12 . 50.9(6)
Cl2 Cu1 N3 C12 . -53.2(6)
Cl3 Cu1 N3 C12 . 141.5(6)
C5 N1 C1 C2 . 87.2(8)
Cu1 N1 C1 C2 . -37.5(8)
C3 N2 C2 C1 . -167.9(7)
Cu1 N2 C2 C1 . -40.9(7)
N1 C1 C2 N2 . 52.2(8)
C2 N2 C3 C4 . 168.9(7)
Cu1 N2 C3 C4 . 41.1(8)
C12 N3 C4 C3 . 164.4(6)
Cu1 N3 C4 C3 . 33.8(8)
N2 C3 C4 N3 . -49.2(9)
C1 N1 C5 C6 . 53.1(10)
Cu1 N1 C5 C6 . 175.6(6)
N1 C5 C6 C7 . 70.4(11)
N1 C5 C6 C11 . -110.6(8)
C11 C6 C7 C8 . 2.9(14)
C5 C6 C7 C8 . -178.1(8)
C6 C7 C8 C9 . -0.7(15)
C7 C8 C9 C10 . -1.4(15)
C8 C9 C10 C11 . 1.1(16)
C7 C6 C11 C10 . -3.1(12)
C5 C6 C11 C10 . 177.9(8)
C9 C10 C11 C6 . 1.1(15)
C4 N3 C12 C13 . 56.4(10)
Cu1 N3 C12 C13 . -176.2(7)
N3 C12 C13 C14 . 70.1(12)
N3 C12 C13 C18 . -110.7(11)
C18 C13 C14 C15 . -4.0(16)
C12 C13 C14 C15 . 175.3(9)
C13 C14 C15 C16 . 3.7(18)
C14 C15 C16 C17 . -2.6(19)
C15 C16 C17 C18 . 1.9(19)
C16 C17 C18 C13 . -2.4(17)
C14 C13 C18 C17 . 3.4(16)
C12 C13 C18 C17 . -175.9(9)
