#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:45:29 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178962 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/91/4119102.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4119102
loop_
_publ_author_name
'Park, Kyung-Ho'
'Marshall, Will J.'
_publ_section_title
;
 Remarkably Volatile Copper(II) Complexes ofN,N‘-Unsymmetrically
 Substituted 1,3-Diketimines as Precursors for Cu Metal Deposition via CVD
 or ALD
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9330
_journal_page_last               9331
_journal_paper_doi               10.1021/ja051158s
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C18 H26 Cu N4'
_chemical_formula_weight         361.97
_chemical_name_systematic
;
 ?
;
_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                 111.566(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.364(3)
_cell_length_b                   9.8308(15)
_cell_length_c                   19.536(3)
_cell_measurement_temperature    293(2)
_cell_volume                     3458.6(9)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10585
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    1.268
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      hemisphere
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ireg.blok
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .45
_exptl_crystal_size_min          .45
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0402
_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)+(0.0549P)²+5.9439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                2703
_reflns_number_total             4074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja051158ssup10.cif
_cod_data_source_block           04149
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3458.5(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4119102
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
Cu11 Cu 0.5000 0.20733(5) 0.2500 0.02538(14) Uani 1 2 d S
N11 N 0.55166(12) 0.1405(2) 0.18812(12) 0.0280(5) Uani 1 1 d .
N12 N 0.41790(12) 0.2769(2) 0.16529(13) 0.0284(5) Uani 1 1 d .
C11 C 0.62328(17) 0.0689(3) 0.21653(17) 0.0385(7) Uani 1 1 d .
H11A H 0.6237 0.0022 0.2532 0.046 Uiso 1 1 calc R
H11B H 0.6637 0.1325 0.2385 0.046 Uiso 1 1 calc R
C12 C 0.63041(19) -0.0001(4) 0.14965(19) 0.0452(8) Uani 1 1 d .
H12A H 0.6818 -0.0049 0.1539 0.054 Uiso 1 1 calc R
H12B H 0.6096 -0.0911 0.1429 0.054 Uiso 1 1 calc R
C13 C 0.58604(18) 0.0924(3) 0.08773(18) 0.0401(7) Uani 1 1 d .
H13A H 0.5619 0.0417 0.0426 0.048 Uiso 1 1 calc R
H13B H 0.6172 0.1624 0.0790 0.048 Uiso 1 1 calc R
C14 C 0.52983(16) 0.1530(3) 0.11577(15) 0.0287(6) Uani 1 1 d .
C15 C 0.46480(17) 0.2163(3) 0.07074(16) 0.0339(7) Uani 1 1 d .
H15A H 0.4551 0.2195 0.0205 0.041 Uiso 1 1 calc R
C16 C 0.41330(15) 0.2753(3) 0.09600(15) 0.0290(6) Uani 1 1 d .
C17 C 0.34450(17) 0.3480(4) 0.04617(17) 0.0421(8) Uani 1 1 d .
H17A H 0.3571 0.4191 0.0184 0.051 Uiso 1 1 calc R
H17B H 0.3103 0.2850 0.0121 0.051 Uiso 1 1 calc R
C18 C 0.3122(2) 0.4059(5) 0.09741(19) 0.0691(13) Uani 1 1 d .
H18A H 0.3163 0.5043 0.0984 0.083 Uiso 1 1 calc R
H18B H 0.2602 0.3817 0.0821 0.083 Uiso 1 1 calc R
C19 C 0.35374(19) 0.3497(5) 0.1698(2) 0.0574(11) Uani 1 1 d .
H19A H 0.3226 0.2879 0.1845 0.069 Uiso 1 1 calc R
H19B H 0.3701 0.4221 0.2060 0.069 Uiso 1 1 calc R
Cu1 Cu 0.0000 0.21258(5) 0.2500 0.02759(14) Uani 1 2 d S
N1 N 0.08754(13) 0.2792(2) 0.33018(13) 0.0295(5) Uani 1 1 d .
N2 N 0.05964(13) 0.1455(2) 0.19553(12) 0.0293(5) Uani 1 1 d .
C1 C 0.08605(19) 0.3473(4) 0.39660(19) 0.0503(9) Uani 1 1 d .
H1A H 0.0796 0.2812 0.4307 0.060 Uiso 1 1 calc R
H1B H 0.0455 0.4121 0.3839 0.060 Uiso 1 1 calc R
C2 C 0.15888(19) 0.4184(4) 0.4303(2) 0.0521(9) Uani 1 1 d .
H2A H 0.1764 0.4148 0.4836 0.063 Uiso 1 1 calc R
H2B H 0.1550 0.5128 0.4149 0.063 Uiso 1 1 calc R
C3 C 0.20968(17) 0.3411(3) 0.40202(16) 0.0354(7) Uani 1 1 d .
H3A H 0.2382 0.2738 0.4375 0.042 Uiso 1 1 calc R
H3B H 0.2435 0.4018 0.3907 0.042 Uiso 1 1 calc R
C4 C 0.15670(15) 0.2740(3) 0.33317(15) 0.0275(6) Uani 1 1 d .
C5 C 0.17976(16) 0.2147(3) 0.28089(16) 0.0325(6) Uani 1 1 d .
H5A H 0.2302 0.2167 0.2892 0.039 Uiso 1 1 calc R
C6 C 0.13275(15) 0.1526(3) 0.21704(16) 0.0298(6) Uani 1 1 d .
C7 C 0.16056(18) 0.0849(3) 0.16239(18) 0.0424(8) Uani 1 1 d .
H7A H 0.1730 0.1516 0.1322 0.051 Uiso 1 1 calc R
H7B H 0.2037 0.0286 0.1872 0.051 Uiso 1 1 calc R
C8 C 0.09469(19) -0.0004(4) 0.1171(2) 0.0500(9) Uani 1 1 d .
H8A H 0.0904 -0.0044 0.0660 0.060 Uiso 1 1 calc R
H8B H 0.0986 -0.0922 0.1363 0.060 Uiso 1 1 calc R
C9 C 0.02991(18) 0.0733(4) 0.12455(19) 0.0458(8) Uani 1 1 d .
H9A H 0.0089 0.1372 0.0844 0.055 Uiso 1 1 calc R
H9B H -0.0084 0.0094 0.1242 0.055 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'
Cu Cu 0.3201 1.2651 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N11 Cu11 N11 140.54(14) . 2_655
N11 Cu11 N12 101.58(9) . 2_655
N11 Cu11 N12 92.07(9) 2_655 2_655
N11 Cu11 N12 92.07(9) . .
N11 Cu11 N12 101.58(9) 2_655 .
N12 Cu11 N12 138.92(14) 2_655 .
C14 N11 C11 109.5(2) . .
C14 N11 Cu11 126.67(19) . .
C11 N11 Cu11 123.81(18) . .
C16 N12 C19 109.1(2) . .
C16 N12 Cu11 126.26(19) . .
C19 N12 Cu11 124.4(2) . .
N11 C11 C12 105.1(3) . .
C13 C12 C11 102.4(2) . .
C12 C13 C14 102.8(2) . .
N11 C14 C15 125.2(2) . .
N11 C14 C13 111.2(3) . .
C15 C14 C13 123.6(3) . .
C14 C15 C16 124.2(3) . .
N12 C16 C15 125.5(3) . .
N12 C16 C17 111.4(2) . .
C15 C16 C17 123.1(3) . .
C18 C17 C16 103.8(2) . .
C19 C18 C17 107.0(3) . .
C18 C19 N12 107.7(3) . .
N1 Cu1 N1 140.73(14) . 2
N1 Cu1 N2 100.93(10) . 2
N1 Cu1 N2 92.16(9) 2 2
N1 Cu1 N2 92.16(9) . .
N1 Cu1 N2 100.93(10) 2 .
N2 Cu1 N2 140.46(14) 2 .
C4 N1 C1 109.1(2) . .
C4 N1 Cu1 126.19(19) . .
C1 N1 Cu1 124.65(19) . .
C6 N2 C9 109.1(2) . .
C6 N2 Cu1 126.02(19) . .
C9 N2 Cu1 124.85(19) . .
N1 C1 C2 106.3(3) . .
C1 C2 C3 104.0(3) . .
C2 C3 C4 103.1(2) . .
N1 C4 C5 125.5(3) . .
N1 C4 C3 111.6(2) . .
C5 C4 C3 122.9(3) . .
C4 C5 C6 124.5(3) . .
N2 C6 C5 125.5(2) . .
N2 C6 C7 111.6(2) . .
C5 C6 C7 122.8(2) . .
C8 C7 C6 102.4(2) . .
C9 C8 C7 103.3(3) . .
N2 C9 C8 105.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu11 N11 1.945(2) .
Cu11 N11 1.945(2) 2_655
Cu11 N12 1.949(2) 2_655
Cu11 N12 1.949(2) .
N11 C14 1.324(3) .
N11 C11 1.470(3) .
N12 C16 1.324(4) .
N12 C19 1.464(4) .
C11 C12 1.523(4) .
C12 C13 1.505(5) .
C13 C14 1.509(4) .
C14 C15 1.390(4) .
C15 C16 1.392(4) .
C16 C17 1.510(4) .
C17 C18 1.475(5) .
C18 C19 1.455(5) .
Cu1 N1 1.950(2) .
Cu1 N1 1.951(2) 2
Cu1 N2 1.951(2) 2
Cu1 N2 1.951(2) .
N1 C4 1.320(3) .
N1 C1 1.470(4) .
N2 C6 1.322(3) .
N2 C9 1.473(4) .
C1 C2 1.493(5) .
C2 C3 1.500(4) .
C3 C4 1.511(4) .
C4 C5 1.384(4) .
C5 C6 1.387(4) .
C6 C7 1.515(4) .
C7 C8 1.511(4) .
C8 C9 1.502(4) .
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
N11 Cu11 N11 C14 112.9(2) 2_655
N12 Cu11 N11 C14 -139.2(2) 2_655
N12 Cu11 N11 C14 1.8(2) .
N11 Cu11 N11 C11 -68.1(2) 2_655
N12 Cu11 N11 C11 39.7(2) 2_655
N12 Cu11 N11 C11 -179.2(2) .
N11 Cu11 N12 C16 -3.4(2) .
N11 Cu11 N12 C16 -146.2(2) 2_655
N12 Cu11 N12 C16 106.9(2) 2_655
N11 Cu11 N12 C19 -178.3(3) .
N11 Cu11 N12 C19 39.0(3) 2_655
N12 Cu11 N12 C19 -67.9(3) 2_655
C14 N11 C11 C12 -17.6(3) .
Cu11 N11 C11 C12 163.3(2) .
N11 C11 C12 C13 28.4(3) .
C11 C12 C13 C14 -28.1(3) .
C11 N11 C14 C15 -179.5(3) .
Cu11 N11 C14 C15 -0.4(4) .
C11 N11 C14 C13 -1.1(3) .
Cu11 N11 C14 C13 177.98(19) .
C12 C13 C14 N11 19.3(3) .
C12 C13 C14 C15 -162.2(3) .
N11 C14 C15 C16 -0.3(5) .
C13 C14 C15 C16 -178.5(3) .
C19 N12 C16 C15 179.3(3) .
Cu11 N12 C16 C15 3.9(4) .
C19 N12 C16 C17 0.0(4) .
Cu11 N12 C16 C17 -175.5(2) .
C14 C15 C16 N12 -1.6(5) .
C14 C15 C16 C17 177.7(3) .
N12 C16 C17 C18 5.6(4) .
C15 C16 C17 C18 -173.8(3) .
C16 C17 C18 C19 -8.8(5) .
C17 C18 C19 N12 9.2(5) .
C16 N12 C19 C18 -5.8(4) .
Cu11 N12 C19 C18 169.8(3) .
N1 Cu1 N1 C4 -108.2(2) 2
N2 Cu1 N1 C4 144.5(2) 2
N2 Cu1 N1 C4 2.0(2) .
N1 Cu1 N1 C1 70.1(3) 2
N2 Cu1 N1 C1 -37.2(3) 2
N2 Cu1 N1 C1 -179.7(3) .
N1 Cu1 N2 C6 0.8(2) .
N1 Cu1 N2 C6 143.5(2) 2
N2 Cu1 N2 C6 -109.3(2) 2
N1 Cu1 N2 C9 178.2(3) .
N1 Cu1 N2 C9 -39.0(3) 2
N2 Cu1 N2 C9 68.1(2) 2
C4 N1 C1 C2 16.0(4) .
Cu1 N1 C1 C2 -162.6(2) .
N1 C1 C2 C3 -23.9(4) .
C1 C2 C3 C4 22.4(4) .
C1 N1 C4 C5 178.7(3) .
Cu1 N1 C4 C5 -2.8(4) .
C1 N1 C4 C3 -1.1(3) .
Cu1 N1 C4 C3 177.40(19) .
C2 C3 C4 N1 -13.9(3) .
C2 C3 C4 C5 166.3(3) .
N1 C4 C5 C6 0.4(5) .
C3 C4 C5 C6 -179.8(3) .
C9 N2 C6 C5 179.2(3) .
Cu1 N2 C6 C5 -3.0(4) .
C9 N2 C6 C7 -0.2(3) .
Cu1 N2 C6 C7 177.6(2) .
C4 C5 C6 N2 2.7(5) .
C4 C5 C6 C7 -177.9(3) .
N2 C6 C7 C8 -16.7(4) .
C5 C6 C7 C8 163.9(3) .
C6 C7 C8 C9 25.7(4) .
C6 N2 C9 C8 17.4(4) .
Cu1 N2 C9 C8 -160.4(2) .
C7 C8 C9 N2 -26.8(4) .
