#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:16:34 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179746 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/42/7004293.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_7004293
loop_
_publ_author_name
'Kopylovich, Maximilian N.'
'Luzyanin, Konstantin V.'
'Haukka, Matti'
'Pombeiro, Armando J. L.'
'Kukushkin, Vadim Yu.'
_publ_section_title
;
 Copper-mediated imine--nitrile coupling leading to unsymmetric
 1,3,5-triazapentadienato complexes containing the incorporated
 iminoisoindolin-1-one moiety
;
_journal_issue                   38
_journal_name_full               'Dalton Transactions'
_journal_page_first              5220
_journal_page_last               5224
_journal_paper_doi               10.1039/b805243c
_journal_year                    2008
_chemical_formula_moiety         'C22 H20 Cu N6 O2, H2 O'
_chemical_formula_sum            'C22 H22 Cu N6 O3'
_chemical_formula_weight         482.00
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 124.989(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.912(2)
_cell_length_b                   4.9750(2)
_cell_length_c                   17.4311(12)
_cell_measurement_reflns_used    6418
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1983.0(2)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Diamond v.3.1d (Brandenburg, 2006)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11792
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    1.142
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_correction_T_min  0.8278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0435
_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)+(0.0449P)²+6.7974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                1783
_reflns_number_total             2186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b805243c.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7004293
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.5000 0.01696(16) Uani 1 2 d S . .
O1 O -0.14551(8) -0.1157(4) 0.32574(14) 0.0270(5) Uani 1 1 d . . .
O2 O 0.0000 0.9522(6) 0.2500 0.0333(7) Uani 1 2 d S . .
H2O H 0.0041 0.8310 0.2994 0.050 Uiso 1 1 d R . .
N1 N -0.06524(9) -0.2482(5) 0.47444(16) 0.0193(5) Uani 1 1 d . . .
N2 N 0.01301(9) 0.5164(5) 0.38380(15) 0.0196(5) Uani 1 1 d . . .
N3 N -0.04949(10) 0.1768(5) 0.38070(16) 0.0221(5) Uani 1 1 d . . .
H3N H -0.0903 0.1106 0.3398 0.033 Uiso 1 1 d R . .
C1 C -0.12345(11) -0.2546(6) 0.39648(19) 0.0204(6) Uani 1 1 d . . .
C2 C -0.15597(12) -0.4631(6) 0.41083(19) 0.0205(6) Uani 1 1 d . . .
C3 C -0.21432(12) -0.5338(6) 0.3562(2) 0.0237(6) Uani 1 1 d . . .
H3 H -0.2415 -0.4475 0.2982 0.028 Uiso 1 1 calc R . .
C4 C -0.23135(13) -0.7375(6) 0.3903(2) 0.0282(7) Uani 1 1 d . . .
H4 H -0.2712 -0.7910 0.3553 0.034 Uiso 1 1 calc R . .
C5 C -0.19095(12) -0.8649(6) 0.4752(2) 0.0255(6) Uani 1 1 d . . .
H5 H -0.2039 -1.0047 0.4964 0.031 Uiso 1 1 calc R . .
C6 C -0.13224(12) -0.7920(6) 0.5295(2) 0.0228(6) Uani 1 1 d . . .
H6 H -0.1048 -0.8795 0.5870 0.027 Uiso 1 1 calc R . .
C7 C -0.11553(11) -0.5859(6) 0.49586(18) 0.0196(6) Uani 1 1 d . . .
C8 C -0.05899(11) -0.4473(5) 0.53467(19) 0.0187(6) Uani 1 1 d . . .
C9 C -0.08380(13) 0.4596(6) 0.2416(2) 0.0291(7) Uani 1 1 d . . .
H9A H -0.0924 0.6523 0.2425 0.035 Uiso 1 1 calc R . .
H9B H -0.0663 0.4430 0.2059 0.035 Uiso 1 1 calc R . .
C10 C -0.03865(13) 0.3703(6) 0.3417(2) 0.0265(6) Uani 1 1 d . . .
C11 C -0.14054(13) 0.3077(7) 0.1904(2) 0.0346(7) Uani 1 1 d . . .
H11A H -0.1592 0.3275 0.2236 0.052 Uiso 1 1 calc R . .
H11B H -0.1330 0.1170 0.1872 0.052 Uiso 1 1 calc R . .
H11C H -0.1665 0.3796 0.1268 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'
O O 0.0106 0.0060 '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
N3 Cu1 N3 179.997(1) 5_556 . ?
N3 Cu1 N1 87.53(10) 5_556 . ?
N3 Cu1 N1 92.47(10) . . yes
N3 Cu1 N1 92.47(10) 5_556 5_556 ?
N3 Cu1 N1 87.53(10) . 5_556 ?
N1 Cu1 N1 180.00(9) . 5_556 ?
C8 N1 C1 107.0(2) . . ?
C8 N1 Cu1 124.36(18) . . ?
C1 N1 Cu1 128.61(18) . . ?
C8 N2 C10 120.9(2) 5_556 . yes
C10 N3 Cu1 131.3(2) . . ?
C10 N3 H3N 112.5 . . ?
Cu1 N3 H3N 116.2 . . ?
O1 C1 N1 126.7(2) . . ?
O1 C1 C2 123.9(2) . . ?
N1 C1 C2 109.4(2) . . ?
C3 C2 C7 122.7(3) . . ?
C3 C2 C1 130.7(3) . . ?
C7 C2 C1 106.6(2) . . ?
C2 C3 C4 116.6(3) . . ?
C2 C3 H3 121.7 . . ?
C4 C3 H3 121.7 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 117.1(3) . . ?
C7 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 C8 132.7(3) . . ?
C2 C7 C8 106.5(2) . . ?
N2 C8 N1 129.5(2) 5_556 . ?
N2 C8 C7 120.0(2) 5_556 . ?
N1 C8 C7 110.5(2) . . ?
C11 C9 C10 115.7(3) . . ?
C11 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C11 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
N3 C10 N2 126.1(3) . . ?
N3 C10 C9 121.6(3) . . ?
N2 C10 C9 112.3(3) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
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 N3 1.927(2) 5_556 ?
Cu1 N3 1.927(2) . yes
Cu1 N1 2.027(2) . yes
Cu1 N1 2.027(2) 5_556 ?
O1 C1 1.227(3) . yes
O2 H2O 1.0025 . ?
N1 C8 1.380(3) . yes
N1 C1 1.398(3) . yes
N2 C8 1.301(3) 5_556 yes
N2 C10 1.390(4) . yes
N3 C10 1.310(4) . yes
N3 H3N 0.9910 . ?
C1 C2 1.491(4) . ?
C2 C3 1.380(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.483(4) . ?
C8 N2 1.301(3) 5_556 ?
C9 C11 1.502(4) . ?
C9 C10 1.519(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
_geom_hbond_publ_flag
O2 H2O N2 1.00 2.06 3.050(3) 167.5 . yes
N3 H3N O1 0.99 1.81 2.697(3) 147.4 . yes
