#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/89/4308916.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_4308916
loop_
_publ_author_name
'Sachindranath Pal'
'Anil Kumar Barik'
'Samik Gupta'
'Arijit Hazra'
'Susanta Kumar Kar'
'Shie-Ming Peng'
'Gene-Hsiang Lee'
'Ray J. Butcher'
'M. Salah El Fallah'
'Joan Ribas'
_publ_section_title
;
Copper(II) Mediated Anion Dependent Formation of Schiff Base Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3880
_journal_page_last               3889
_journal_paper_doi               10.1021/ic0501420
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C13 H18.5 Cl2 Cu N6 O1.25'
_chemical_formula_weight         413.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.121(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.525(2)
_cell_length_b                   19.728(6)
_cell_length_c                   11.971(4)
_cell_measurement_temperature    93(2)
_cell_volume                     1715.6(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13254
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    1.598
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             846
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²+1.0290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                3744
_reflns_number_total             4205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0501420si20050128_061251.cif
_cod_data_source_block           skgm
_cod_original_cell_volume        1715.5(9)
_cod_original_formula_sum        'C13 H18.50 Cl2 Cu N6 O1.25'
_cod_database_code               4308916
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.71418(3) 0.144891(11) 0.32273(2) 0.01413(7) Uani 1 1 d . . .
Cl1 Cl 0.81257(7) 0.19365(3) 0.16325(4) 0.02182(11) Uani 1 1 d . . .
Cl2 Cl 0.84308(8) -0.07404(3) 0.17633(6) 0.03278(14) Uani 1 1 d . . .
O O 0.5981(2) 0.22311(8) 0.56994(15) 0.0331(4) Uani 1 1 d . . .
H0A H 0.5081 0.2317 0.5969 0.050 Uiso 1 1 calc R . .
O1W O 0.4465(4) 0.1581(2) 0.7362(9) 0.086(4) Uani 0.25 1 d PD . .
H1W1 H 0.3477(4) 0.1727(12) 0.7495(18) 0.129 Uiso 0.25 1 d PD . .
H1W2 H 0.5283(14) 0.1864(14) 0.770(4) 0.129 Uiso 0.25 1 d PD . .
N1A N 0.5279(2) 0.07658(8) 0.23905(15) 0.0173(3) Uani 1 1 d . . .
N2A N 0.4779(2) 0.19474(8) 0.32258(15) 0.0181(3) Uani 1 1 d . . .
N3A N 0.5144(2) 0.01692(9) 0.18236(16) 0.0205(4) Uani 1 1 d . . .
H3A H 0.611(4) -0.0041(14) 0.182(2) 0.029(7) Uiso 1 1 d . . .
N1B N 0.9376(2) 0.08537(8) 0.38449(14) 0.0158(3) Uani 1 1 d . . .
N2B N 0.8612(2) 0.20459(8) 0.44806(15) 0.0179(3) Uani 1 1 d . . .
N3B N 1.0153(2) 0.02715(8) 0.36342(15) 0.0166(3) Uani 1 1 d . . .
H3B H 0.959(3) 0.0018(14) 0.313(2) 0.022(6) Uiso 1 1 d . . .
C1A C 0.2905(3) -0.06418(13) 0.0653(2) 0.0341(6) Uani 1 1 d . . .
H1AA H 0.3931 -0.0962 0.0888 0.085(13) Uiso 1 1 calc R . .
H1AB H 0.2670 -0.0548 -0.0177 0.053(9) Uiso 1 1 calc R . .
H1AC H 0.1801 -0.0839 0.0811 0.063(10) Uiso 1 1 calc R . .
C2A C 0.3383(3) 0.00025(11) 0.13157(18) 0.0227(4) Uani 1 1 d . . .
C3A C 0.2297(3) 0.05163(11) 0.15494(18) 0.0222(4) Uani 1 1 d . . .
H3AA H 0.0993 0.0549 0.1305 0.031(7) Uiso 1 1 calc R . .
C4A C 0.3524(3) 0.09798(10) 0.22226(17) 0.0171(4) Uani 1 1 d . . .
C5A C 0.3308(3) 0.16290(10) 0.27369(17) 0.0192(4) Uani 1 1 d . . .
H5AA H 0.2127 0.1809 0.2711 0.021(6) Uiso 1 1 calc R . .
C6A C 0.4650(3) 0.26182(10) 0.37264(19) 0.0229(4) Uani 1 1 d . . .
H6AA H 0.3410 0.2672 0.3855 0.020(6) Uiso 1 1 calc R . .
H6AB H 0.4799 0.2970 0.3169 0.019(6) Uiso 1 1 calc R . .
C7 C 0.6088(3) 0.27258(11) 0.48624(19) 0.0234(4) Uani 1 1 d . . .
H7A H 0.5853 0.3178 0.5173 0.013(5) Uiso 1 1 calc R . .
C1B C 1.2968(3) -0.04243(11) 0.42093(19) 0.0229(4) Uani 1 1 d . . .
H1BA H 1.2146 -0.0789 0.3828 0.038(8) Uiso 1 1 calc R . .
H1BB H 1.3670 -0.0576 0.4977 0.024(6) Uiso 1 1 calc R . .
H1BC H 1.3819 -0.0308 0.3743 0.032(7) Uiso 1 1 calc R . .
C2B C 1.1854(3) 0.01840(10) 0.43307(17) 0.0179(4) Uani 1 1 d . . .
C3B C 1.2220(3) 0.07438(10) 0.50487(18) 0.0201(4) Uani 1 1 d . . .
H3BA H 1.3308 0.0835 0.5641 0.024(6) Uiso 1 1 calc R . .
C4B C 1.0644(3) 0.11459(10) 0.47133(17) 0.0169(4) Uani 1 1 d . . .
C5B C 1.0144(3) 0.18063(10) 0.50670(18) 0.0188(4) Uani 1 1 d . . .
H5BA H 1.0913 0.2046 0.5699 0.023(6) Uiso 1 1 calc R . .
C6B C 0.8048(3) 0.27270(10) 0.4744(2) 0.0229(4) Uani 1 1 d . . .
H6BA H 0.8140 0.3043 0.4119 0.024(6) Uiso 1 1 calc R . .
H6BB H 0.8891 0.2890 0.5475 0.028(7) Uiso 1 1 calc R . .
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
N2B Cu N1A 160.93(7) . . ?
N2B Cu N1B 79.84(7) . . ?
N1A Cu N1B 101.39(7) . . ?
N2B Cu N2A 91.62(7) . . ?
N1A Cu N2A 80.09(7) . . ?
N1B Cu N2A 157.49(7) . . ?
N2B Cu Cl1 97.74(6) . . ?
N1A Cu Cl1 100.96(5) . . ?
N1B Cu Cl1 97.05(5) . . ?
N2A Cu Cl1 104.75(5) . . ?
C7 O H0A 109.5 . . ?
H1W1 O1W H1W2 104.49(17) . . ?
N3A N1A C4A 104.82(16) . . ?
N3A N1A Cu 141.76(13) . . ?
C4A N1A Cu 113.06(13) . . ?
C5A N2A C6A 119.33(17) . . ?
C5A N2A Cu 114.65(14) . . ?
C6A N2A Cu 126.02(13) . . ?
C2A N3A N1A 112.09(17) . . ?
C2A N3A H3A 128.9(18) . . ?
N1A N3A H3A 119.0(18) . . ?
N3B N1B C4B 104.86(15) . . ?
N3B N1B Cu 142.01(13) . . ?
C4B N1B Cu 112.81(12) . . ?
C5B N2B C6B 119.46(17) . . ?
C5B N2B Cu 116.03(14) . . ?
C6B N2B Cu 124.50(13) . . ?
N1B N3B C2B 112.60(17) . . ?
N1B N3B H3B 120.1(18) . . ?
C2B N3B H3B 127.4(18) . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N3A C2A C3A 107.17(18) . . ?
N3A C2A C1A 121.4(2) . . ?
C3A C2A C1A 131.5(2) . . ?
C2A C3A C4A 105.13(18) . . ?
C2A C3A H3AA 127.4 . . ?
C4A C3A H3AA 127.4 . . ?
N1A C4A C3A 110.79(18) . . ?
N1A C4A C5A 115.27(17) . . ?
C3A C4A C5A 133.92(18) . . ?
N2A C5A C4A 116.77(18) . . ?
N2A C5A H5AA 121.6 . . ?
C4A C5A H5AA 121.6 . . ?
N2A C6A C7 112.63(16) . . ?
N2A C6A H6AA 109.1 . . ?
C7 C6A H6AA 109.1 . . ?
N2A C6A H6AB 109.1 . . ?
C7 C6A H6AB 109.1 . . ?
H6AA C6A H6AB 107.8 . . ?
O C7 C6A 112.28(18) . . ?
O C7 C6B 107.64(17) . . ?
C6A C7 C6B 113.61(18) . . ?
O C7 H7A 107.7 . . ?
C6A C7 H7A 107.7 . . ?
C6B C7 H7A 107.7 . . ?
C2B C1B H1BA 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
C2B C1B H1BC 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
N3B C2B C3B 106.63(17) . . ?
N3B C2B C1B 120.73(18) . . ?
C3B C2B C1B 132.61(18) . . ?
C2B C3B C4B 104.98(17) . . ?
C2B C3B H3BA 127.5 . . ?
C4B C3B H3BA 127.5 . . ?
N1B C4B C3B 110.93(17) . . ?
N1B C4B C5B 115.20(16) . . ?
C3B C4B C5B 133.81(18) . . ?
N2B C5B C4B 116.04(18) . . ?
N2B C5B H5BA 122.0 . . ?
C4B C5B H5BA 122.0 . . ?
N2B C6B C7 111.16(17) . . ?
N2B C6B H6BA 109.4 . . ?
C7 C6B H6BA 109.4 . . ?
N2B C6B H6BB 109.4 . . ?
C7 C6B H6BB 109.4 . . ?
H6BA C6B H6BB 108.0 . . ?
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 N2B 1.9990(17) . ?
Cu N1A 2.0131(17) . ?
Cu N1B 2.0257(16) . ?
Cu N2A 2.0311(17) . ?
Cu Cl1 2.4199(7) . ?
O C7 1.416(3) . ?
O H0A 0.8400 . ?
O1W H1W1 0.8500(11) . ?
O1W H1W2 0.8500(11) . ?
N1A N3A 1.349(2) . ?
N1A C4A 1.350(2) . ?
N2A C5A 1.275(3) . ?
N2A C6A 1.466(3) . ?
N3A C2A 1.346(3) . ?
N3A H3A 0.84(3) . ?
N1B N3B 1.342(2) . ?
N1B C4B 1.344(3) . ?
N2B C5B 1.274(3) . ?
N2B C6B 1.468(3) . ?
N3B C2B 1.344(3) . ?
N3B H3B 0.82(3) . ?
C1A C2A 1.492(3) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A C3A 1.376(3) . ?
C3A C4A 1.396(3) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.448(3) . ?
C5A H5AA 0.9500 . ?
C6A C7 1.516(3) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7 C6B 1.518(3) . ?
C7 H7A 1.0000 . ?
C1B C2B 1.493(3) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C2B C3B 1.382(3) . ?
C3B C4B 1.396(3) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.449(3) . ?
C5B H5BA 0.9500 . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
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
O H0A Cl1 0.84 2.36 3.1325(18) 153.0 4_566
O H0A O1W 0.84 2.35 2.845(9) 118.5 .
N3A H3A Cl2 0.84(3) 2.24(3) 3.071(2) 172(3) .
N3B H3B Cl2 0.82(3) 2.22(3) 3.0274(19) 172(2) .
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
N2B Cu N1A N3A -120.8(3) . . . . ?
N1B Cu N1A N3A -28.9(2) . . . . ?
N2A Cu N1A N3A 173.9(2) . . . . ?
Cl1 Cu N1A N3A 70.7(2) . . . . ?
N2B Cu N1A C4A 67.6(3) . . . . ?
N1B Cu N1A C4A 159.41(14) . . . . ?
N2A Cu N1A C4A 2.27(14) . . . . ?
Cl1 Cu N1A C4A -101.00(13) . . . . ?
N2B Cu N2A C5A -162.71(15) . . . . ?
N1A Cu N2A C5A 0.01(15) . . . . ?
N1B Cu N2A C5A -95.8(2) . . . . ?
Cl1 Cu N2A C5A 98.85(15) . . . . ?
N2B Cu N2A C6A 17.22(17) . . . . ?
N1A Cu N2A C6A 179.94(17) . . . . ?
N1B Cu N2A C6A 84.1(2) . . . . ?
Cl1 Cu N2A C6A -81.22(16) . . . . ?
C4A N1A N3A C2A -0.3(2) . . . . ?
Cu N1A N3A C2A -172.31(17) . . . . ?
N2B Cu N1B N3B -173.1(2) . . . . ?
N1A Cu N1B N3B 26.2(2) . . . . ?
N2A Cu N1B N3B 117.8(2) . . . . ?
Cl1 Cu N1B N3B -76.5(2) . . . . ?
N2B Cu N1B C4B -0.95(13) . . . . ?
N1A Cu N1B C4B -161.57(13) . . . . ?
N2A Cu N1B C4B -70.0(2) . . . . ?
Cl1 Cu N1B C4B 95.69(13) . . . . ?
N1A Cu N2B C5B 94.6(2) . . . . ?
N1B Cu N2B C5B -0.88(15) . . . . ?
N2A Cu N2B C5B 158.17(16) . . . . ?
Cl1 Cu N2B C5B -96.71(15) . . . . ?
N1A Cu N2B C6B -86.1(3) . . . . ?
N1B Cu N2B C6B 178.42(17) . . . . ?
N2A Cu N2B C6B -22.54(17) . . . . ?
Cl1 Cu N2B C6B 82.59(16) . . . . ?
C4B N1B N3B C2B 0.0(2) . . . . ?
Cu N1B N3B C2B 172.50(16) . . . . ?
N1A N3A C2A C3A 0.5(2) . . . . ?
N1A N3A C2A C1A -179.2(2) . . . . ?
N3A C2A C3A C4A -0.5(2) . . . . ?
C1A C2A C3A C4A 179.2(2) . . . . ?
N3A N1A C4A C3A -0.1(2) . . . . ?
Cu N1A C4A C3A 174.59(14) . . . . ?
N3A N1A C4A C5A -178.71(17) . . . . ?
Cu N1A C4A C5A -4.0(2) . . . . ?
C2A C3A C4A N1A 0.4(2) . . . . ?
C2A C3A C4A C5A 178.7(2) . . . . ?
C6A N2A C5A C4A 177.86(17) . . . . ?
Cu N2A C5A C4A -2.2(2) . . . . ?
N1A C4A C5A N2A 4.2(3) . . . . ?
C3A C4A C5A N2A -174.0(2) . . . . ?
C5A N2A C6A C7 140.8(2) . . . . ?
Cu N2A C6A C7 -39.1(2) . . . . ?
N2A C6A C7 O -57.7(2) . . . . ?
N2A C6A C7 C6B 64.8(2) . . . . ?
N1B N3B C2B C3B 0.2(2) . . . . ?
N1B N3B C2B C1B -178.29(17) . . . . ?
N3B C2B C3B C4B -0.2(2) . . . . ?
C1B C2B C3B C4B 178.0(2) . . . . ?
N3B N1B C4B C3B -0.1(2) . . . . ?
Cu N1B C4B C3B -175.12(14) . . . . ?
N3B N1B C4B C5B 177.47(17) . . . . ?
Cu N1B C4B C5B 2.4(2) . . . . ?
C2B C3B C4B N1B 0.2(2) . . . . ?
C2B C3B C4B C5B -176.8(2) . . . . ?
C6B N2B C5B C4B -176.89(18) . . . . ?
Cu N2B C5B C4B 2.4(2) . . . . ?
N1B C4B C5B N2B -3.3(3) . . . . ?
C3B C4B C5B N2B 173.6(2) . . . . ?
C5B N2B C6B C7 -131.0(2) . . . . ?
Cu N2B C6B C7 49.8(2) . . . . ?
O C7 C6B N2B 54.6(2) . . . . ?
C6A C7 C6B N2B -70.4(2) . . . . ?
