#------------------------------------------------------------------------------
#$Date: 2019-12-23 11:59:59 +0200 (Mon, 23 Dec 2019) $
#$Revision: 245501 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556706.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_1556706
loop_
_publ_author_name
'Gayfullina, R.'
'Jaaskelainen, S.'
'Koshevoy, I.O.'
'Hirva, P.'
_publ_section_title
;
 Activation of the Cyano Group at Imidazole via Copper Stimulated
 Alcoholysis
;
_journal_name_full               Inorganics
_journal_page_first              87
_journal_paper_doi               10.3390/inorganics7070087
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C10 H16 Cl2 Cu N4 O2'
_chemical_formula_sum            'C10 H16 Cl2 Cu N4 O2'
_chemical_formula_weight         358.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                108.336(3)
_cell_angle_beta                 95.921(3)
_cell_angle_gamma                98.615(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6535(5)
_cell_length_b                   10.3149(8)
_cell_length_c                   13.5498(10)
_cell_measurement_reflns_used    8460
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.01
_cell_measurement_theta_min      2.19
_cell_volume                     732.01(10)
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_molecular_graphics    'Diamond v.4.03 (Brandenburg, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO CCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28668
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         1.604
_exptl_absorpt_coefficient_mu    1.859
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       plate
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.025
_refine_diff_density_max         1.720
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0412P)²+0.7955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3092
_reflns_number_total             3882
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1.cif
_cod_data_source_block           1
_cod_database_code               1556706
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.707
_shelx_estimated_absorpt_t_max   0.955
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7538(5) 0.7650(3) 0.9453(2) 0.0231(5) Uani 1 1 d . . . . .
H8 H 0.856868 0.849358 0.989422 0.028 Uiso 1 1 calc R U . . .
C2 C 0.4556(6) 0.7580(3) 1.0684(2) 0.0317(6) Uani 1 1 d . . . . .
H5A H 0.310461 0.692811 1.068402 0.048 Uiso 1 1 calc R U . . .
H5B H 0.577073 0.770463 1.129375 0.048 Uiso 1 1 calc R U . . .
H5C H 0.412797 0.847975 1.072383 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4529(4) 0.5867(3) 0.8883(2) 0.0214(5) Uani 1 1 d . . . . .
C4 C 0.2327(5) 0.4961(3) 0.8846(2) 0.0263(5) Uani 1 1 d . . . . .
C5 C 0.5988(4) 0.5805(2) 0.8124(2) 0.0191(5) Uani 1 1 d . . . . .
C6 C 0.5895(4) 0.4890(2) 0.7057(2) 0.0198(5) Uani 1 1 d . . . . .
C7 C 0.3423(5) 0.2962(3) 0.5656(2) 0.0236(5) Uani 1 1 d . . . . .
H2 H 0.474746 0.247489 0.541407 0.028 Uiso 1 1 calc R U . . .
H3 H 0.310584 0.354324 0.521677 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1194(5) 0.1940(3) 0.5579(2) 0.0303(6) Uani 1 1 d . . . . .
H11A H 0.067331 0.133353 0.484506 0.046 Uiso 1 1 calc R U . . .
H11B H 0.153684 0.137562 0.601916 0.046 Uiso 1 1 calc R U . . .
H11C H -0.009628 0.243844 0.582288 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7874(5) 0.9834(3) 0.7311(2) 0.0269(6) Uani 1 1 d . . . . .
H9 H 0.956675 1.024706 0.730325 0.032 Uiso 1 1 calc R U . . .
H13 H 0.763048 1.006131 0.805505 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6178(6) 1.0465(3) 0.6756(3) 0.0347(7) Uani 1 1 d . . . . .
H7A H 0.649129 1.147573 0.710907 0.052 Uiso 1 1 calc R U . . .
H7B H 0.643526 1.025849 0.602229 0.052 Uiso 1 1 calc R U . . .
H7C H 0.449961 1.007279 0.677384 0.052 Uiso 1 1 calc R U . . .
N1 N 0.7863(4) 0.6935(2) 0.85033(17) 0.0215(4) Uani 1 1 d . . . . .
N2 N 0.7526(4) 0.5255(2) 0.65671(17) 0.0215(4) Uani 1 1 d . . . . .
H1N2 H 0.777451 0.471600 0.590857 0.026 Uiso 1 1 d R U . . .
N3 N 0.5543(4) 0.7029(2) 0.97193(16) 0.0217(4) Uani 1 1 d . . . . .
N4 N 0.0581(5) 0.4216(3) 0.8804(2) 0.0422(7) Uani 1 1 d . . . . .
O1 O 0.4078(3) 0.38191(18) 0.67621(14) 0.0243(4) Uani 1 1 d . . . . .
O2 O 0.7501(3) 0.83587(18) 0.68300(14) 0.0226(4) Uani 1 1 d . . . . .
H1O2 H 0.598924 0.802501 0.667443 0.027 Uiso 1 1 d R U . . .
Cl1 Cl 1.22188(10) 0.66262(7) 0.60907(5) 0.02513(14) Uani 1 1 d . . . . .
Cl2 Cl 1.26172(11) 0.88472(7) 0.85556(5) 0.02608(14) Uani 1 1 d . . . . .
Cu1 Cu 0.99093(5) 0.70618(3) 0.73841(2) 0.01771(9) Uani 1 1 d . . . . .
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
N1 C1 N3 111.0(2) . .
N1 C1 H8 124.5 . .
N3 C1 H8 124.5 . .
N3 C2 H5A 109.5 . .
N3 C2 H5B 109.5 . .
H5A C2 H5B 109.5 . .
N3 C2 H5C 109.5 . .
H5A C2 H5C 109.5 . .
H5B C2 H5C 109.5 . .
N3 C3 C5 106.6(2) . .
N3 C3 C4 124.0(2) . .
C5 C3 C4 129.3(2) . .
N4 C4 C3 178.7(3) . .
N1 C5 C3 108.3(2) . .
N1 C5 C6 116.8(2) . .
C3 C5 C6 134.8(2) . .
N2 C6 O1 131.3(2) . .
N2 C6 C5 115.7(2) . .
O1 C6 C5 113.0(2) . .
O1 C7 C8 106.2(2) . .
O1 C7 H2 110.5 . .
C8 C7 H2 110.5 . .
O1 C7 H3 110.5 . .
C8 C7 H3 110.5 . .
H2 C7 H3 108.7 . .
C7 C8 H11A 109.5 . .
C7 C8 H11B 109.5 . .
H11A C8 H11B 109.5 . .
C7 C8 H11C 109.5 . .
H11A C8 H11C 109.5 . .
H11B C8 H11C 109.5 . .
O2 C9 C10 112.0(2) . .
O2 C9 H9 109.2 . .
C10 C9 H9 109.2 . .
O2 C9 H13 109.2 . .
C10 C9 H13 109.2 . .
H9 C9 H13 107.9 . .
C9 C10 H7A 109.5 . .
C9 C10 H7B 109.5 . .
H7A C10 H7B 109.5 . .
C9 C10 H7C 109.5 . .
H7A C10 H7C 109.5 . .
H7B C10 H7C 109.5 . .
C1 N1 C5 106.7(2) . .
C1 N1 Cu1 141.28(18) . .
C5 N1 Cu1 111.42(16) . .
C6 N2 Cu1 115.65(18) . .
C6 N2 H1N2 124.4 . .
Cu1 N2 H1N2 119.7 . .
C1 N3 C3 107.3(2) . .
C1 N3 C2 125.8(2) . .
C3 N3 C2 126.7(2) . .
C6 O1 C7 119.8(2) . .
C9 O2 Cu1 122.02(15) . .
C9 O2 H1O2 109.4 . .
Cu1 O2 H1O2 116.9 . .
N1 Cu1 N2 80.28(9) . .
N1 Cu1 Cl2 91.50(6) . .
N2 Cu1 Cl2 167.75(6) . .
N1 Cu1 Cl1 165.22(6) . .
N2 Cu1 Cl1 89.84(6) . .
Cl2 Cu1 Cl1 96.36(3) . .
N1 Cu1 O2 90.99(7) . .
N2 Cu1 O2 92.11(7) . .
Cl2 Cu1 O2 97.13(5) . .
Cl1 Cu1 O2 100.40(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.314(3) .
C1 N3 1.351(3) .
C1 H8 0.9500 .
C2 N3 1.457(3) .
C2 H5A 0.9800 .
C2 H5B 0.9800 .
C2 H5C 0.9800 .
C3 N3 1.362(3) .
C3 C5 1.376(3) .
C3 C4 1.426(4) .
C4 N4 1.141(4) .
C5 N1 1.373(3) .
C5 C6 1.447(3) .
C6 N2 1.270(3) .
C6 O1 1.317(3) .
C7 O1 1.456(3) .
C7 C8 1.489(4) .
C7 H2 0.9900 .
C7 H3 0.9900 .
C8 H11A 0.9800 .
C8 H11B 0.9800 .
C8 H11C 0.9800 .
C9 O2 1.427(3) .
C9 C10 1.502(4) .
C9 H9 0.9900 .
C9 H13 0.9900 .
C10 H7A 0.9800 .
C10 H7B 0.9800 .
C10 H7C 0.9800 .
N1 Cu1 2.024(2) .
N2 Cu1 2.038(2) .
N2 H1N2 0.9288 .
O2 Cu1 2.2745(17) .
O2 H1O2 0.8500 .
Cl1 Cu1 2.2650(7) .
Cl2 Cu1 2.2516(7) .
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
N3 C3 C5 N1 -0.4(3) . . . .
C4 C3 C5 N1 177.6(3) . . . .
N3 C3 C5 C6 -177.0(3) . . . .
C4 C3 C5 C6 1.0(5) . . . .
N1 C5 C6 N2 -2.3(3) . . . .
C3 C5 C6 N2 174.2(3) . . . .
N1 C5 C6 O1 178.6(2) . . . .
C3 C5 C6 O1 -4.9(4) . . . .
N3 C1 N1 C5 0.8(3) . . . .
N3 C1 N1 Cu1 170.9(2) . . . .
C3 C5 N1 C1 -0.2(3) . . . .
C6 C5 N1 C1 177.1(2) . . . .
C3 C5 N1 Cu1 -173.59(16) . . . .
C6 C5 N1 Cu1 3.8(3) . . . .
O1 C6 N2 Cu1 178.5(2) . . . .
C5 C6 N2 Cu1 -0.5(3) . . . .
N1 C1 N3 C3 -1.0(3) . . . .
N1 C1 N3 C2 -175.8(2) . . . .
C5 C3 N3 C1 0.8(3) . . . .
C4 C3 N3 C1 -177.3(2) . . . .
C5 C3 N3 C2 175.5(2) . . . .
C4 C3 N3 C2 -2.6(4) . . . .
N2 C6 O1 C7 -11.6(4) . . . .
C5 C6 O1 C7 167.3(2) . . . .
C8 C7 O1 C6 -174.9(2) . . . .
C10 C9 O2 Cu1 175.65(17) . . . .
