#------------------------------------------------------------------------------
#$Date: 2019-11-24 06:41:04 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236988 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/99/4349962.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_4349962
loop_
_publ_author_name
'Zhang, Xiaofeng'
'Zhang, Zilong'
'Xiang, Shiqun'
'Zhu, Yingzu'
'Chen, Changneng'
'Huang, Deguang'
_publ_section_title
;
 Base induced C--CN bond cleavage at room temperature: a convenient method
 for the activation of acetonitrile
;
_journal_issue                   5
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              1135
_journal_paper_doi               10.1039/C8QI01258J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C24 H21 Cu N4 O2, C8 H20 N, C H2 Cl2'
_chemical_formula_sum            'C33 H43 Cl2 Cu N5 O2'
_chemical_formula_weight         676.16
_chemical_name_common            '[Cu(NNN-Me-pincer)-CN](Et4N).CH2Cl2'
_space_group_IT_number           44
_space_group_name_Hall           'I 2 -2'
_space_group_name_H-M_alt        'I m m 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2'
_symmetry_space_group_name_H-M   'I m m 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-12-08 deposited with the CCDC.	2019-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1357(4)
_cell_length_b                   16.0102(6)
_cell_length_c                   11.0362(5)
_cell_measurement_reflns_used    2046
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0450
_cell_measurement_theta_min      5.5260
_cell_volume                     1614.20(12)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_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      100(2)
_diffrn_detector_area_resol_mean 5.2797
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2768
_diffrn_reflns_theta_full        75.93
_diffrn_reflns_theta_max         75.93
_diffrn_reflns_theta_min         4.87
_exptl_absorpt_coefficient_mu    2.778
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_correction_T_min  0.4896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            purple-red
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             710
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1380
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0907P)²+0.2098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                1356
_reflns_number_total             1380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qi01258j2.cif
_cod_data_source_block           Complex2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4349962
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'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 0.5000 0.44100(4) 0.0164(2) Uani 1 4 d S . .
O1 O 0.5000 0.71942(17) 0.2507(3) 0.0221(6) Uani 1 2 d S . .
N1 N 0.5000 0.6233(2) 0.4091(3) 0.0189(7) Uani 1 2 d S . .
N2 N 0.5000 0.5000 0.2654(5) 0.0182(10) Uani 1 4 d S . .
N4 N 0.5000 0.5000 0.7196(7) 0.0386(14) Uani 1 4 d S . .
N5 N 0.0000 0.5000 0.8427(5) 0.0227(10) Uani 1 4 d S . .
C1 C 0.5000 0.6473(2) 0.2939(4) 0.0177(7) Uani 1 2 d S . .
C2 C 0.5000 0.5732(2) 0.2083(4) 0.0180(8) Uani 1 2 d S . .
C3 C 0.5000 0.5763(2) 0.0828(4) 0.0204(8) Uani 1 2 d S . .
H3A H 0.5000 0.6282 0.0409 0.025 Uiso 1 2 calc SR . .
C4 C 0.5000 0.5000 0.0194(6) 0.0214(10) Uani 1 4 d S . .
H4A H 0.5000 0.5000 -0.0666 0.026 Uiso 1 4 calc SR . .
C5 C 0.5000 0.6857(2) 0.5014(4) 0.0193(8) Uani 1 2 d S . .
C6 C 0.6322(3) 0.71377(19) 0.5487(3) 0.0251(6) Uani 1 1 d . . .
C7 C 0.6318(3) 0.7713(2) 0.6436(3) 0.0302(7) Uani 1 1 d . . .
H7A H 0.7216 0.7914 0.6757 0.036 Uiso 1 1 calc R . .
C8 C 0.5000 0.7991(3) 0.6908(5) 0.0280(9) Uani 1 2 d S . .
H8A H 0.5000 0.8376 0.7563 0.034 Uiso 1 2 calc SR . .
C9 C 0.7753(3) 0.6805(2) 0.5015(4) 0.0374(8) Uani 1 1 d . . .
H9A H 0.8564 0.7072 0.5448 0.056 Uiso 1 1 calc R . .
H9B H 0.7834 0.6927 0.4147 0.056 Uiso 1 1 calc R . .
H9C H 0.7794 0.6200 0.5142 0.056 Uiso 1 1 calc R . .
C10 C 0.5000 0.5000 0.6241(6) 0.0204(12) Uani 1 4 d S . .
C11 C 0.0964(7) 0.5535(3) 0.7606(6) 0.0274(13) Uani 0.50 1 d P A -1
H11A H 0.0344 0.5878 0.7065 0.033 Uiso 0.50 1 calc PR A -1
H11B H 0.1588 0.5171 0.7097 0.033 Uiso 0.50 1 calc PR A -1
C12 C 0.1974(4) 0.6130(2) 0.8424(6) 0.0482(11) Uani 0.50 1 d P A -1
H12A H 0.2597 0.6473 0.7899 0.072 Uiso 0.50 1 calc PR A -1
H12B H 0.2590 0.5787 0.8955 0.072 Uiso 0.50 1 calc PR A -1
H12C H 0.1352 0.6494 0.8919 0.072 Uiso 0.50 1 calc PR A -1
C11' C 0.0916(7) 0.5554(3) 0.9271(7) 0.0275(13) Uani 0.50 1 d P A -2
H11C H 0.1512 0.5204 0.9821 0.033 Uiso 0.50 1 calc PR A -2
H11D H 0.0267 0.5912 0.9768 0.033 Uiso 0.50 1 calc PR A -2
C12' C 0.1974(4) 0.6130(2) 0.8424(6) 0.0482(11) Uani 0.50 1 d P A -2
H12D H 0.2570 0.6494 0.8940 0.072 Uiso 0.50 1 calc PR A -2
H12E H 0.1372 0.6473 0.7883 0.072 Uiso 0.50 1 calc PR A -2
H12F H 0.2616 0.5770 0.7942 0.072 Uiso 0.50 1 calc PR A -2
C13 C 1.0000 0.5000 0.3713(8) 0.0374(16) Uani 1 4 d S . .
H13A H 1.0000 0.4515 0.4224 0.045 Uiso 0.50 2 d SPR . .
H13B H 1.0000 0.5485 0.4224 0.045 Uiso 0.50 2 d SPR . .
Cl1 Cl 0.83996(12) 0.5000 0.28324(14) 0.0392(3) Uani 1 2 d S . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
N2 Cu1 N1 79.89(10) . 2_665
N2 Cu1 N1 79.89(10) . .
N1 Cu1 N1 159.8(2) 2_665 .
N2 Cu1 C10 180.000(2) . .
N1 Cu1 C10 100.11(10) 2_665 .
N1 Cu1 C10 100.11(10) . .
C1 N1 C5 118.7(3) . .
C1 N1 Cu1 117.0(3) . .
C5 N1 Cu1 124.4(3) . .
C2 N2 C2 123.5(5) 2_665 .
C2 N2 Cu1 118.2(3) 2_665 .
C2 N2 Cu1 118.2(3) . .
C11 N5 C11 107.2(6) 2_565 .
C11 N5 C11 68.2(5) 2_565 3
C11 N5 C11 70.5(5) . 3
C11 N5 C11 70.5(5) 2_565 4_565
C11 N5 C11 68.2(5) . 4_565
C11 N5 C11 107.2(6) 3 4_565
C11 N5 C11' 177.8(4) 2_565 .
C11 N5 C11' 73.8(4) . .
C11 N5 C11' 110.5(3) 3 .
C11 N5 C11' 111.7(3) 4_565 .
C11 N5 C11' 110.5(3) 2_565 4_565
C11 N5 C11' 111.7(3) . 4_565
C11 N5 C11' 177.8(4) 3 4_565
C11 N5 C11' 73.8(4) 4_565 4_565
C11' N5 C11' 70.7(5) . 4_565
C11 N5 C11' 111.7(3) 2_565 3
C11 N5 C11' 110.5(3) . 3
C11 N5 C11' 73.8(4) 3 3
C11 N5 C11' 177.8(4) 4_565 3
C11' N5 C11' 66.1(5) . 3
C11' N5 C11' 105.2(7) 4_565 3
C11 N5 C11' 73.8(4) 2_565 2_565
C11 N5 C11' 177.8(4) . 2_565
C11 N5 C11' 111.7(3) 3 2_565
C11 N5 C11' 110.5(3) 4_565 2_565
C11' N5 C11' 105.2(7) . 2_565
C11' N5 C11' 66.1(5) 4_565 2_565
C11' N5 C11' 70.7(5) 3 2_565
O1 C1 N1 129.3(4) . .
O1 C1 C2 119.1(4) . .
N1 C1 C2 111.7(3) . .
N2 C2 C3 120.3(4) . .
N2 C2 C1 113.2(4) . .
C3 C2 C1 126.5(4) . .
C2 C3 C4 117.7(4) . .
C2 C3 H3A 121.1 . .
C4 C3 H3A 121.1 . .
C3 C4 C3 120.4(6) . 2_665
C3 C4 H4A 119.8 . .
C3 C4 H4A 119.8 2_665 .
C6 C5 C6 120.6(4) . 3_655
C6 C5 N1 119.63(18) . .
C6 C5 N1 119.63(18) 3_655 .
C5 C6 C7 119.5(3) . .
C5 C6 C9 120.7(3) . .
C7 C6 C9 119.7(3) . .
C8 C7 C6 119.8(3) . .
C8 C7 H7A 120.1 . .
C6 C7 H7A 120.1 . .
C7 C8 C7 120.7(4) 3_655 .
C7 C8 H8A 119.7 3_655 .
C7 C8 H8A 119.7 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N4 C10 Cu1 180.000(2) . .
N5 C11 C12 109.3(5) . .
N5 C11 H11A 109.8 . .
C12 C11 H11A 109.8 . .
N5 C11 H11B 109.8 . .
C12 C11 H11B 109.8 . .
H11A C11 H11B 108.3 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N5 C11' H11C 110.2 . .
N5 C11' H11D 110.2 . .
H11C C11' H11D 108.5 . .
Cl1 C13 Cl1 112.8(5) . 2_765
Cl1 C13 H13A 109.0 . .
Cl1 C13 H13A 109.0 2_765 .
Cl1 C13 H13B 109.0 . .
Cl1 C13 H13B 109.0 2_765 .
H13A C13 H13B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.938(5) .
Cu1 N1 2.004(3) 2_665
Cu1 N1 2.004(3) .
Cu1 C10 2.021(7) .
O1 C1 1.249(5) .
N1 C1 1.329(5) .
N1 C5 1.427(5) .
N2 C2 1.331(5) 2_665
N2 C2 1.331(5) .
N4 C10 1.054(10) .
N5 C11 1.526(7) 2_565
N5 C11 1.526(7) .
N5 C11 1.526(7) 3
N5 C11 1.526(7) 4_565
N5 C11' 1.535(7) .
N5 C11' 1.535(7) 4_565
N5 C11' 1.535(7) 3
N5 C11' 1.535(7) 2_565
C1 C2 1.516(5) .
C2 C3 1.386(6) .
C3 C4 1.407(5) .
C3 H3A 0.9500 .
C4 C3 1.407(5) 2_665
C4 H4A 0.9500 .
C5 C6 1.391(4) .
C5 C6 1.391(4) 3_655
C6 C7 1.394(4) .
C6 C9 1.505(4) .
C7 C8 1.385(4) .
C7 H7A 0.9500 .
C8 C7 1.385(4) 3_655
C8 H8A 0.9500 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C11 C12 1.605(8) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C11' H11C 0.9900 .
C11' H11D 0.9900 .
C13 Cl1 1.755(5) .
C13 Cl1 1.755(5) 2_765
C13 H13A 0.9602 .
C13 H13B 0.9602 .
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_4
N2 Cu1 N1 C1 0.000(1) . .
N1 Cu1 N1 C1 0.000(2) 2_665 .
C10 Cu1 N1 C1 180.000(1) . .
N2 Cu1 N1 C5 180.000(1) . .
N1 Cu1 N1 C5 180.000(2) 2_665 .
C10 Cu1 N1 C5 0.000(1) . .
N1 Cu1 N2 C2 0.0 2_665 2_665
N1 Cu1 N2 C2 180.0 . 2_665
C10 Cu1 N2 C2 -90(100) . 2_665
N1 Cu1 N2 C2 180.0 2_665 .
N1 Cu1 N2 C2 0.0 . .
C10 Cu1 N2 C2 90(100) . .
C5 N1 C1 O1 0.000(2) . .
Cu1 N1 C1 O1 180.000(1) . .
C5 N1 C1 C2 180.000(1) . .
Cu1 N1 C1 C2 0.000(1) . .
C2 N2 C2 C3 0.000(1) 2_665 .
Cu1 N2 C2 C3 180.000(1) . .
C2 N2 C2 C1 180.000(1) 2_665 .
Cu1 N2 C2 C1 0.000(1) . .
O1 C1 C2 N2 180.000(1) . .
N1 C1 C2 N2 0.000(1) . .
O1 C1 C2 C3 0.000(2) . .
N1 C1 C2 C3 180.000(1) . .
N2 C2 C3 C4 0.000(1) . .
C1 C2 C3 C4 180.000(1) . .
C2 C3 C4 C3 0.000(1) . 2_665
C1 N1 C5 C6 -92.2(3) . .
Cu1 N1 C5 C6 87.8(3) . .
C1 N1 C5 C6 92.2(3) . 3_655
Cu1 N1 C5 C6 -87.8(3) . 3_655
C6 C5 C6 C7 -0.8(6) 3_655 .
N1 C5 C6 C7 -176.4(3) . .
C6 C5 C6 C9 177.1(3) 3_655 .
N1 C5 C6 C9 1.6(5) . .
C5 C6 C7 C8 0.9(6) . .
C9 C6 C7 C8 -177.1(4) . .
C6 C7 C8 C7 -1.0(8) . 3_655
N2 Cu1 C10 N4 0(100) . .
N1 Cu1 C10 N4 167(100) 2_665 .
N1 Cu1 C10 N4 -13(100) . .
C11 N5 C11 C12 178.4(5) 2_565 .
C11 N5 C11 C12 119.9(3) 3 .
C11 N5 C11 C12 -121.5(3) 4_565 .
C11' N5 C11 C12 0.5(3) . .
C11' N5 C11 C12 -60.3(5) 4_565 .
C11' N5 C11 C12 56.5(6) 3 .
C11' N5 C11 C12 -65(13) 2_565 .
