#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:16:34 +0100 (vie 25 de mar de 2016) $
#$Revision: 179746 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/42/7004294.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_7004294
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         'C24 H24 Cu N6 O2'
_chemical_formula_sum            'C24 H24 Cu N6 O2'
_chemical_formula_weight         492.03
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.191(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7199(7)
_cell_length_b                   5.2390(3)
_cell_length_c                   18.9373(10)
_cell_measurement_reflns_used    17298
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1060.70(11)
_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.3.1e (Brandenburg, 2007)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0791
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14215
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    1.066
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_correction_T_min  0.7893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0397
_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)+(0.0488P)²+0.5932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                1840
_reflns_number_total             2434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b805243c.txt
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7004294
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 0.5000 0.0000 1.0000 0.01933(15) Uani 1 2 d S . .
O1 O 0.77428(16) -0.3357(3) 0.97949(9) 0.0261(4) Uani 1 1 d . . .
N1 N 0.56123(18) -0.2946(4) 0.94316(10) 0.0200(4) Uani 1 1 d . . .
N2 N 0.63284(19) 0.3942(4) 1.12705(10) 0.0220(5) Uani 1 1 d . . .
N3 N 0.6619(2) 0.0514(4) 1.04876(11) 0.0240(5) Uani 1 1 d . . .
H3N H 0.7262 -0.0586 1.0351 0.033(8) Uiso 1 1 d R . .
C1 C 0.6813(2) -0.4035(5) 0.94312(12) 0.0219(5) Uani 1 1 d . . .
C2 C 0.6780(2) -0.6168(5) 0.89063(12) 0.0215(5) Uani 1 1 d . . .
C3 C 0.7711(2) -0.7808(5) 0.87151(12) 0.0245(5) Uani 1 1 d . . .
H3 H 0.8543 -0.7695 0.8923 0.029 Uiso 1 1 calc R . .
C4 C 0.7363(2) -0.9639(5) 0.82010(13) 0.0256(6) Uani 1 1 d . . .
H4 H 0.7973 -1.0798 0.8052 0.031 Uiso 1 1 calc R . .
C5 C 0.6135(2) -0.9793(5) 0.79031(13) 0.0242(5) Uani 1 1 d . . .
H5 H 0.5924 -1.1061 0.7556 0.029 Uiso 1 1 calc R . .
C6 C 0.5213(2) -0.8132(5) 0.81033(12) 0.0229(5) Uani 1 1 d . . .
H6 H 0.4377 -0.8239 0.7902 0.027 Uiso 1 1 calc R . .
C7 C 0.5571(2) -0.6307(5) 0.86107(12) 0.0205(5) Uani 1 1 d . . .
C8 C 0.4850(2) -0.4249(5) 0.89410(12) 0.0206(5) Uani 1 1 d . . .
C9 C 0.8364(2) 0.1890(5) 1.13094(13) 0.0230(5) Uani 1 1 d . . .
H9 H 0.8519 0.3391 1.1630 0.028 Uiso 1 1 calc R . .
C10 C 0.7027(2) 0.2066(5) 1.09843(12) 0.0217(5) Uani 1 1 d . . .
C11 C 0.8521(3) -0.0520(6) 1.17561(16) 0.0400(8) Uani 1 1 d . . .
H11A H 0.7943 -0.0471 1.2134 0.060 Uiso 1 1 calc R . .
H11B H 0.9383 -0.0623 1.1966 0.060 Uiso 1 1 calc R . .
H11C H 0.8338 -0.2018 1.1456 0.060 Uiso 1 1 calc R . .
C12 C 0.9322(3) 0.1968(7) 1.07519(15) 0.0421(8) Uani 1 1 d . . .
H12A H 0.9274 0.0382 1.0477 0.063 Uiso 1 1 calc R . .
H12B H 1.0164 0.2149 1.0986 0.063 Uiso 1 1 calc R . .
H12C H 0.9144 0.3422 1.0435 0.063 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 179.998(1) 3_657 . ?
N3 Cu1 N1 92.62(8) 3_657 3_657 ?
N3 Cu1 N1 87.38(8) . 3_657 ?
N3 Cu1 N1 87.38(8) 3_657 . ?
N3 Cu1 N1 92.62(8) . . yes
N1 Cu1 N1 179.999(1) 3_657 . ?
C8 N1 C1 107.3(2) . . ?
C8 N1 Cu1 122.71(16) . . ?
C1 N1 Cu1 130.02(16) . . ?
C8 N2 C10 120.7(2) 3_657 . yes
C10 N3 Cu1 132.91(18) . . ?
C10 N3 H3N 111.5 . . ?
Cu1 N3 H3N 115.6 . . ?
O1 C1 N1 126.2(2) . . ?
O1 C1 C2 124.8(2) . . ?
N1 C1 C2 109.1(2) . . ?
C7 C2 C3 122.4(2) . . ?
C7 C2 C1 106.6(2) . . ?
C3 C2 C1 131.0(2) . . ?
C2 C3 C4 116.6(2) . . ?
C2 C3 H3 121.7 . . ?
C4 C3 H3 121.7 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 117.0(2) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C2 C7 C6 121.5(2) . . ?
C2 C7 C8 107.0(2) . . ?
C6 C7 C8 131.5(2) . . ?
N2 C8 N1 131.3(2) 3_657 . ?
N2 C8 C7 118.6(2) 3_657 . ?
N1 C8 C7 110.0(2) . . ?
C10 C9 C11 109.7(2) . . ?
C10 C9 C12 112.4(2) . . ?
C11 C9 C12 110.7(2) . . ?
C10 C9 H9 108.0 . . ?
C11 C9 H9 108.0 . . ?
C12 C9 H9 108.0 . . ?
N3 C10 N2 124.9(2) . . ?
N3 C10 C9 120.9(2) . . ?
N2 C10 C9 114.1(2) . . ?
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 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 1.924(2) 3_657 ?
Cu1 N3 1.924(2) . yes
Cu1 N1 2.019(2) 3_657 ?
Cu1 N1 2.019(2) . yes
O1 C1 1.222(3) . yes
N1 C8 1.373(3) . ?
N1 C1 1.408(3) . ?
N2 C8 1.307(3) 3_657 yes
N2 C10 1.371(3) . ?
N3 C10 1.295(3) . ?
N3 H3N 0.9481 . ?
C1 C2 1.494(4) . ?
C2 C7 1.376(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.398(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.490(3) . ?
C8 N2 1.307(3) 3_657 ?
C9 C10 1.521(3) . ?
C9 C11 1.522(4) . ?
C9 C12 1.526(4) . ?
C9 H9 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
N3 H3N O1 0.95 1.89 2.741(3) 148.5 . yes
