#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:01:37 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179737 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/33/7003322.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_7003322
loop_
_publ_author_name
'Petrovic, Dejan'
'Hill, Lyndal M. R.'
'Jones, Peter G.'
'Tolman, William B.'
'Tamm, Matthias'
_publ_section_title
;
 Synthesis and reactivity of copper(i) complexes with an
 ethylene-bridged bis(imidazolin-2-imine) ligand
;
_journal_issue                   7
_journal_name_full               'Dalton Transactions'
_journal_page_first              887
_journal_page_last               894
_journal_paper_doi               10.1039/b715590e
_journal_year                    2008
_chemical_formula_sum            'C24 H44 Cl Cu N6'
_chemical_formula_weight         515.64
_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                 107.664(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7423(12)
_cell_length_b                   9.2407(6)
_cell_length_c                   18.3128(14)
_cell_measurement_reflns_used    6881
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      2.33
_cell_volume                     2699.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω- & φ-scan'
_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  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            56246
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.8730
_exptl_absorpt_correction_T_min  0.7697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    'rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         8246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0319
_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)+(0.0394P)²+1.1240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0875
_reflns_number_gt                6538
_reflns_number_total             8246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715590e.txt
_cod_data_source_block           dpet17a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7003322
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
Cu1 Cu 0.949046(10) 0.177318(19) 0.159309(9) 0.02131(5) Uani 1 1 d . . .
Cl1 Cl 1.02631(2) 0.04640(4) 0.25149(2) 0.02708(8) Uani 1 1 d . . .
N1 N 0.98405(7) 0.30271(13) 0.08131(7) 0.0211(2) Uani 1 1 d . . .
N2 N 0.83535(7) 0.26443(14) 0.11338(6) 0.0201(2) Uani 1 1 d . . .
N3 N 1.10262(7) 0.46080(14) 0.14239(6) 0.0209(2) Uani 1 1 d . . .
N4 N 1.12387(7) 0.27036(14) 0.07864(6) 0.0208(2) Uani 1 1 d . . .
N5 N 0.68418(7) 0.27586(14) 0.08853(6) 0.0200(2) Uani 1 1 d . . .
N6 N 0.76525(7) 0.26070(14) 0.20868(6) 0.0199(2) Uani 1 1 d . . .
C1 C 0.91830(8) 0.41217(17) 0.05489(8) 0.0249(3) Uani 1 1 d . . .
H1A H 0.9213 0.4568 0.0067 0.030 Uiso 1 1 calc R . .
H1B H 0.9253 0.4892 0.0939 0.030 Uiso 1 1 calc R . .
C2 C 0.83443(8) 0.33668(16) 0.04180(8) 0.0221(3) Uani 1 1 d . . .
H2A H 0.7883 0.4082 0.0270 0.027 Uiso 1 1 calc R . .
H2B H 0.8256 0.2648 0.0000 0.027 Uiso 1 1 calc R . .
C3 C 1.06339(8) 0.34402(15) 0.09975(7) 0.0186(2) Uani 1 1 d . . .
C4 C 1.18818(8) 0.45900(17) 0.14686(8) 0.0236(3) Uani 1 1 d . . .
C5 C 1.20101(8) 0.34194(17) 0.10830(8) 0.0230(3) Uani 1 1 d . . .
C6 C 1.24708(10) 0.5793(2) 0.18135(10) 0.0349(4) Uani 1 1 d . . .
H6A H 1.3033 0.5553 0.1791 0.052 Uiso 1 1 calc R . .
H6B H 1.2489 0.5927 0.2349 0.052 Uiso 1 1 calc R . .
H6C H 1.2278 0.6687 0.1527 0.052 Uiso 1 1 calc R . .
C7 C 1.28035(9) 0.2967(2) 0.09305(10) 0.0332(4) Uani 1 1 d . . .
H7A H 1.2761 0.3172 0.0395 0.050 Uiso 1 1 calc R . .
H7B H 1.2892 0.1928 0.1028 0.050 Uiso 1 1 calc R . .
H7C H 1.3277 0.3506 0.1268 0.050 Uiso 1 1 calc R . .
C8 C 1.06902(10) 0.52254(18) 0.20139(8) 0.0268(3) Uani 1 1 d . . .
H8 H 1.0094 0.4897 0.1885 0.032 Uiso 1 1 calc R . .
C9 C 1.11473(12) 0.4584(2) 0.27979(9) 0.0387(4) Uani 1 1 d . . .
H9A H 1.1121 0.3525 0.2768 0.058 Uiso 1 1 calc R . .
H9B H 1.0880 0.4919 0.3175 0.058 Uiso 1 1 calc R . .
H9C H 1.1735 0.4895 0.2955 0.058 Uiso 1 1 calc R . .
C10 C 1.06697(14) 0.6862(2) 0.20002(13) 0.0466(5) Uani 1 1 d . . .
H10A H 1.1244 0.7237 0.2183 0.070 Uiso 1 1 calc R . .
H10B H 1.0351 0.7212 0.2334 0.070 Uiso 1 1 calc R . .
H10C H 1.0401 0.7197 0.1475 0.070 Uiso 1 1 calc R . .
C11 C 1.10316(9) 0.13695(18) 0.03314(8) 0.0267(3) Uani 1 1 d . . .
H11 H 1.0406 0.1324 0.0133 0.032 Uiso 1 1 calc R . .
C12 C 1.13427(13) 0.1378(2) -0.03698(10) 0.0421(4) Uani 1 1 d . . .
H12A H 1.1213 0.2314 -0.0631 0.063 Uiso 1 1 calc R . .
H12B H 1.1065 0.0604 -0.0721 0.063 Uiso 1 1 calc R . .
H12C H 1.1950 0.1222 -0.0208 0.063 Uiso 1 1 calc R . .
C13 C 1.13113(12) 0.00413(19) 0.08338(11) 0.0370(4) Uani 1 1 d . . .
H13A H 1.1925 0.0003 0.1015 0.056 Uiso 1 1 calc R . .
H13B H 1.1094 -0.0831 0.0536 0.056 Uiso 1 1 calc R . .
H13C H 1.1095 0.0096 0.1274 0.056 Uiso 1 1 calc R . .
C14 C 0.76675(8) 0.26457(15) 0.13397(7) 0.0178(2) Uani 1 1 d . . .
C15 C 0.63250(8) 0.28842(16) 0.13681(8) 0.0216(3) Uani 1 1 d . . .
C16 C 0.68224(9) 0.28275(16) 0.20970(8) 0.0223(3) Uani 1 1 d . . .
C17 C 0.54040(9) 0.3164(2) 0.10783(10) 0.0334(4) Uani 1 1 d . . .
H17A H 0.5193 0.3375 0.1511 0.050 Uiso 1 1 calc R . .
H17B H 0.5118 0.2307 0.0805 0.050 Uiso 1 1 calc R . .
H17C H 0.5296 0.3993 0.0728 0.050 Uiso 1 1 calc R . .
C18 C 0.65875(10) 0.3046(2) 0.28140(9) 0.0323(3) Uani 1 1 d . . .
H18A H 0.6006 0.3381 0.2682 0.049 Uiso 1 1 calc R . .
H18B H 0.6958 0.3772 0.3136 0.049 Uiso 1 1 calc R . .
H18C H 0.6645 0.2130 0.3094 0.049 Uiso 1 1 calc R . .
C19 C 0.65670(8) 0.21601(17) 0.00973(7) 0.0225(3) Uani 1 1 d . . .
H19 H 0.7085 0.2026 -0.0060 0.027 Uiso 1 1 calc R . .
C20 C 0.61779(12) 0.0668(2) 0.00815(10) 0.0384(4) Uani 1 1 d . . .
H20A H 0.6571 0.0035 0.0450 0.058 Uiso 1 1 calc R . .
H20B H 0.6054 0.0257 -0.0434 0.058 Uiso 1 1 calc R . .
H20C H 0.5658 0.0751 0.0219 0.058 Uiso 1 1 calc R . .
C21 C 0.60071(11) 0.3200(2) -0.04764(10) 0.0407(4) Uani 1 1 d . . .
H21A H 0.5453 0.3236 -0.0399 0.061 Uiso 1 1 calc R . .
H21B H 0.5949 0.2867 -0.0998 0.061 Uiso 1 1 calc R . .
H21C H 0.6258 0.4168 -0.0402 0.061 Uiso 1 1 calc R . .
C22 C 0.84287(9) 0.26339(17) 0.27357(8) 0.0243(3) Uani 1 1 d . . .
H22 H 0.8869 0.2161 0.2551 0.029 Uiso 1 1 calc R . .
C23 C 0.87183(12) 0.4178(2) 0.29396(10) 0.0389(4) Uani 1 1 d . . .
H23A H 0.8805 0.4654 0.2491 0.058 Uiso 1 1 calc R . .
H23B H 0.9246 0.4173 0.3360 0.058 Uiso 1 1 calc R . .
H23C H 0.8291 0.4705 0.3099 0.058 Uiso 1 1 calc R . .
C24 C 0.83778(11) 0.1758(2) 0.34255(9) 0.0345(4) Uani 1 1 d . . .
H24A H 0.8070 0.2312 0.3710 0.052 Uiso 1 1 calc R . .
H24B H 0.8945 0.1555 0.3761 0.052 Uiso 1 1 calc R . .
H24C H 0.8085 0.0845 0.3250 0.052 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'
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
N2 Cu1 N1 85.22(5) . . ?
N2 Cu1 Cl1 145.24(3) . . ?
N1 Cu1 Cl1 128.98(3) . . ?
C3 N1 C1 118.72(12) . . ?
C3 N1 Cu1 117.42(9) . . ?
C1 N1 Cu1 105.92(8) . . ?
C14 N2 C2 118.90(11) . . ?
C14 N2 Cu1 133.06(9) . . ?
C2 N2 Cu1 108.01(8) . . ?
C3 N3 C4 108.97(11) . . ?
C3 N3 C8 119.75(11) . . ?
C4 N3 C8 124.63(12) . . ?
C3 N4 C5 109.18(12) . . ?
C3 N4 C11 120.64(11) . . ?
C5 N4 C11 130.17(12) . . ?
C14 N5 C15 108.57(11) . . ?
C14 N5 C19 121.03(11) . . ?
C15 N5 C19 124.76(11) . . ?
C14 N6 C16 108.95(11) . . ?
C14 N6 C22 121.63(11) . . ?
C16 N6 C22 128.27(11) . . ?
N1 C1 C2 107.50(12) . . ?
N2 C2 C1 108.01(11) . . ?
N1 C3 N4 123.74(13) . . ?
N1 C3 N3 129.79(12) . . ?
N4 C3 N3 106.47(11) . . ?
C5 C4 N3 107.49(12) . . ?
C5 C4 C6 129.12(13) . . ?
N3 C4 C6 123.02(14) . . ?
C4 C5 N4 107.88(12) . . ?
C4 C5 C7 127.93(14) . . ?
N4 C5 C7 124.05(14) . . ?
N3 C8 C10 112.70(14) . . ?
N3 C8 C9 110.15(13) . . ?
C10 C8 C9 113.97(15) . . ?
N4 C11 C13 110.97(12) . . ?
N4 C11 C12 113.02(14) . . ?
C13 C11 C12 113.12(14) . . ?
N2 C14 N6 124.53(12) . . ?
N2 C14 N5 128.92(12) . . ?
N6 C14 N5 106.47(11) . . ?
C16 C15 N5 107.77(11) . . ?
C16 C15 C17 128.47(13) . . ?
N5 C15 C17 123.54(13) . . ?
C15 C16 N6 107.98(12) . . ?
C15 C16 C18 128.25(13) . . ?
N6 C16 C18 123.66(12) . . ?
N5 C19 C21 112.42(13) . . ?
N5 C19 C20 111.18(12) . . ?
C21 C19 C20 112.91(14) . . ?
N6 C22 C23 110.65(13) . . ?
N6 C22 C24 113.75(13) . . ?
C23 C22 C24 112.93(13) . . ?
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
Cu1 N2 2.0019(11) . ?
Cu1 N1 2.0577(12) . ?
Cu1 Cl1 2.1590(4) . ?
N1 C3 1.3237(17) . ?
N1 C1 1.4648(18) . ?
N2 C14 1.3130(16) . ?
N2 C2 1.4670(17) . ?
N3 C3 1.3764(18) . ?
N3 C4 1.4099(17) . ?
N3 C8 1.4760(18) . ?
N4 C3 1.3694(17) . ?
N4 C5 1.4054(18) . ?
N4 C11 1.4693(19) . ?
N5 C14 1.3843(16) . ?
N5 C15 1.4172(17) . ?
N5 C19 1.4822(17) . ?
N6 C14 1.3764(16) . ?
N6 C16 1.4105(17) . ?
N6 C22 1.4711(17) . ?
C1 C2 1.5203(19) . ?
C4 C5 1.344(2) . ?
C4 C6 1.493(2) . ?
C5 C7 1.497(2) . ?
C8 C10 1.513(3) . ?
C8 C9 1.527(2) . ?
C11 C13 1.520(2) . ?
C11 C12 1.525(2) . ?
C15 C16 1.3429(19) . ?
C15 C17 1.4932(19) . ?
C16 C18 1.4943(19) . ?
C19 C21 1.519(2) . ?
C19 C20 1.521(2) . ?
C22 C23 1.517(2) . ?
C22 C24 1.524(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
N2 Cu1 N1 C3 152.18(11) . . . . ?
Cl1 Cu1 N1 C3 -20.99(13) . . . . ?
N2 Cu1 N1 C1 16.87(9) . . . . ?
Cl1 Cu1 N1 C1 -156.30(7) . . . . ?
N1 Cu1 N2 C14 -168.66(14) . . . . ?
Cl1 Cu1 N2 C14 2.00(18) . . . . ?
N1 Cu1 N2 C2 13.15(9) . . . . ?
Cl1 Cu1 N2 C2 -176.19(7) . . . . ?
C3 N1 C1 C2 -177.19(12) . . . . ?
Cu1 N1 C1 C2 -42.58(12) . . . . ?
C14 N2 C2 C1 141.47(13) . . . . ?
Cu1 N2 C2 C1 -40.04(13) . . . . ?
N1 C1 C2 N2 56.13(15) . . . . ?
C1 N1 C3 N4 -136.50(14) . . . . ?
Cu1 N1 C3 N4 93.96(14) . . . . ?
C1 N1 C3 N3 44.6(2) . . . . ?
Cu1 N1 C3 N3 -84.98(16) . . . . ?
C5 N4 C3 N1 -179.21(12) . . . . ?
C11 N4 C3 N1 -0.2(2) . . . . ?
C5 N4 C3 N3 -0.06(14) . . . . ?
C11 N4 C3 N3 178.94(12) . . . . ?
C4 N3 C3 N1 179.54(13) . . . . ?
C8 N3 C3 N1 26.8(2) . . . . ?
C4 N3 C3 N4 0.46(14) . . . . ?
C8 N3 C3 N4 -152.24(12) . . . . ?
C3 N3 C4 C5 -0.71(15) . . . . ?
C8 N3 C4 C5 150.35(14) . . . . ?
C3 N3 C4 C6 172.85(13) . . . . ?
C8 N3 C4 C6 -36.1(2) . . . . ?
N3 C4 C5 N4 0.66(16) . . . . ?
C6 C4 C5 N4 -172.38(15) . . . . ?
N3 C4 C5 C7 176.55(14) . . . . ?
C6 C4 C5 C7 3.5(3) . . . . ?
C3 N4 C5 C4 -0.38(16) . . . . ?
C11 N4 C5 C4 -179.25(14) . . . . ?
C3 N4 C5 C7 -176.47(13) . . . . ?
C11 N4 C5 C7 4.7(2) . . . . ?
C3 N3 C8 C10 -136.23(15) . . . . ?
C4 N3 C8 C10 75.58(19) . . . . ?
C3 N3 C8 C9 95.26(16) . . . . ?
C4 N3 C8 C9 -52.94(19) . . . . ?
C3 N4 C11 C13 -101.96(15) . . . . ?
C5 N4 C11 C13 76.80(18) . . . . ?
C3 N4 C11 C12 129.75(14) . . . . ?
C5 N4 C11 C12 -51.5(2) . . . . ?
C2 N2 C14 N6 -150.48(13) . . . . ?
Cu1 N2 C14 N6 31.5(2) . . . . ?
C2 N2 C14 N5 25.8(2) . . . . ?
Cu1 N2 C14 N5 -152.19(12) . . . . ?
C16 N6 C14 N2 171.79(14) . . . . ?
C22 N6 C14 N2 3.1(2) . . . . ?
C16 N6 C14 N5 -5.24(16) . . . . ?
C22 N6 C14 N5 -173.88(13) . . . . ?
C15 N5 C14 N2 -173.06(14) . . . . ?
C19 N5 C14 N2 32.3(2) . . . . ?
C15 N5 C14 N6 3.78(16) . . . . ?
C19 N5 C14 N6 -150.90(12) . . . . ?
C14 N5 C15 C16 -0.87(17) . . . . ?
C19 N5 C15 C16 152.64(14) . . . . ?
C14 N5 C15 C17 174.14(14) . . . . ?
C19 N5 C15 C17 -32.4(2) . . . . ?
N5 C15 C16 N6 -2.35(17) . . . . ?
C17 C15 C16 N6 -177.04(15) . . . . ?
N5 C15 C16 C18 173.92(15) . . . . ?
C17 C15 C16 C18 -0.8(3) . . . . ?
C14 N6 C16 C15 4.81(17) . . . . ?
C22 N6 C16 C15 172.47(14) . . . . ?
C14 N6 C16 C18 -171.68(15) . . . . ?
C22 N6 C16 C18 -4.0(2) . . . . ?
C14 N5 C19 C21 -135.08(14) . . . . ?
C15 N5 C19 C21 74.49(18) . . . . ?
C14 N5 C19 C20 97.23(16) . . . . ?
C15 N5 C19 C20 -53.20(19) . . . . ?
C14 N6 C22 C23 85.27(16) . . . . ?
C16 N6 C22 C23 -81.00(18) . . . . ?
C14 N6 C22 C24 -146.36(14) . . . . ?
C16 N6 C22 C24 47.4(2) . . . . ?
