#------------------------------------------------------------------------------
#$Date: 2016-11-08 21:06:35 +0100 (mar 08 de nov de 2016) $
#$Revision: 188232 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/05/7040583.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_7040583
loop_
_publ_author_name
'Kongkaew, Manisa'
'Sitthisuwannakul, Kannika'
'Nakarajouyphon, Vasut'
'Pornsuwan, Soraya'
'Kongsaeree, Palangpon'
'Sangtrirutnugul, Preeyanuch'
_publ_section_title
;
 Benzimidazole-triazole ligands with pendent triazole functionality:
 unexpected formation and effects on copper-catalyzed aerobic alcohol
 oxidation.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16810
_journal_page_last               16819
_journal_paper_doi               10.1039/c6dt02770a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C20 H30 Cl2 Cu N8 Si2, C2 H3 N'
_chemical_formula_sum            'C22 H33 Cl2 Cu N9 Si2'
_chemical_formula_weight         614.19
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-08-01
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.05.11 svn.r3296 for OlexSys, GUI svn.r3563)
;
_audit_update_record
;
2016-08-12 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                100.7014(10)
_cell_angle_beta                 103.0788(11)
_cell_angle_gamma                105.8527(9)
_cell_formula_units_Z            2
_cell_length_a                   8.9699(2)
_cell_length_b                   13.5062(4)
_cell_length_c                   14.1297(4)
_cell_measurement_reflns_used    8280
_cell_measurement_temperature    293
_cell_measurement_theta_max      3.55
_cell_measurement_theta_min      27.45
_cell_volume                     1547.01(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  KappaCCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5489
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        22.505
_diffrn_reflns_theta_max         22.505
_diffrn_reflns_theta_min         2.469
_exptl_absorpt_coefficient_mu    0.983
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             638
_exptl_crystal_recrystallization_method 'slow evaporation from CH3CN solution'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.749
_refine_diff_density_min         -1.119
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.021(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0768
_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)+(0.1751P)²+1.3761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2229
_refine_ls_wR_factor_ref         0.2308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3293
_reflns_number_total             3713
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt02770a2.cif
_cod_data_source_block           shelxl1
_cod_depositor_comments
'Adding full bibliography for 7040582--7040583.cif.'
_cod_original_cell_volume        1547.02(7)
_cod_database_code               7040583
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13A-C12A \\sim C13A-C11A \\sim C12A-C11A
 with sigma of 0.04
 Si1A-C10 \\sim Si1A-C13A \\sim Si1A-C12A \\sim Si1A-C11A
 with sigma of 0.02
 C13-C12 \\sim C13-C11 \\sim C12-C11
 with sigma of 0.04
 Si1-C10 \\sim Si1-C13 \\sim Si1-C12 \\sim Si1-C11
 with sigma of 0.02
 C20-C18 \\sim C20-C19 \\sim C18-C19
 with sigma of 0.04
 Si2-C17 \\sim Si2-C20 \\sim Si2-C18 \\sim Si2-C19
 with sigma of 0.02
 C20A-C18A \\sim C20A-C19A \\sim C18A-C19A
 with sigma of 0.04
 Si2A-C17 \\sim Si2A-C20A \\sim Si2A-C18A \\sim Si2A-C19A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Si1) = Uanis(Si1A)
Uanis(Si2) = Uanis(Si2A)
4. Rigid body (RIGU) restrains
 Si2, C20, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Si1, C13, C12, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Si2A, C20A, C18A, C19A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Si1A, C13A, C12A, C11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H17C)=Sof(H17D)=Sof(Si2A)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=
 Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=1-FVAR(1)
 Sof(Si2)=Sof(H17A)=Sof(H17B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
 Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5) H10D(0.5) Si1(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) H13C(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C11(0.5)
 H11A(0.5) H11C(0.5) H11B(0.5) Si1A(0.5) C13A(0.5) H13D(0.5) H13E(0.5)
 H13F(0.5) C12A(0.5) H12D(0.5) H12E(0.5) H12F(0.5) C11A(0.5) H11D(0.5)
 H11E(0.5) H11F(0.5)
6.a Riding coordinates:
 C11(H11A,H11C,H11B), C20A(H20D,H20E,H20F)
6.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B), C17(H17C,H17D), C10(H10A,H10B), C10(H10C,H10D)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C16(H16), C9(H9), C6(H6), C5(H5), C4(H4)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C13A(H13D,H13E,H13F),
 C12A(H12D,H12E,H12F), C11A(H11D,H11E,H11F), C18A(H18D,H18E,H18F), C19A(H19D,
 H19E,H19F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
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
Cu1 Cu 0.33739(7) 0.79527(5) 1.00778(5) 0.0391(4) Uani 1 1 d . . . . .
Cl2 Cl 0.4113(2) 0.78746(14) 1.17033(13) 0.0585(6) Uani 1 1 d . . . . .
Cl1 Cl 0.06547(18) 0.67722(14) 0.92703(16) 0.0679(6) Uani 1 1 d . . . . .
Si2 Si 0.5471(19) 1.5293(12) 1.3003(9) 0.0890(16) Uani 0.62(4) 1 d D U P A 1
N2 N 0.2373(5) 1.0744(3) 0.9970(4) 0.0377(11) Uani 1 1 d . . . . .
N7 N 0.5938(6) 1.3935(4) 1.0839(4) 0.0455(13) Uani 1 1 d . . . . .
N6 N 0.5251(6) 1.2945(4) 1.0284(4) 0.0403(12) Uani 1 1 d . . . . .
N1 N 0.2712(5) 0.9291(4) 1.0382(3) 0.0385(12) Uani 1 1 d . . . . .
N3 N 0.3673(6) 0.8573(4) 0.8869(4) 0.0425(12) Uani 1 1 d . . . . .
N8 N 0.4743(6) 1.4277(4) 1.0985(4) 0.0444(12) Uani 1 1 d . . . . .
C15 C 0.3620(6) 1.2665(5) 1.0092(4) 0.0398(14) Uani 1 1 d . . . . .
N5 N 0.3857(6) 0.8929(5) 0.7502(4) 0.0487(13) Uani 1 1 d . . . . .
C2 C 0.2175(6) 0.9806(4) 1.1107(4) 0.0383(14) Uani 1 1 d . . . . .
N4 N 0.4055(6) 0.8253(4) 0.8063(4) 0.0495(13) Uani 1 1 d . . . . .
C3 C 0.1930(6) 1.0724(5) 1.0845(5) 0.0431(15) Uani 1 1 d . . . . .
C8 C 0.3245(6) 0.9462(4) 0.8841(4) 0.0385(14) Uani 1 1 d . . . . .
C7 C 0.1810(7) 0.9540(5) 1.1942(5) 0.0457(15) Uani 1 1 d . . . . .
H7 H 0.1949 0.8933 1.2115 0.055 Uiso 1 1 calc R . . . .
C16 C 0.3296(7) 1.3522(5) 1.0529(5) 0.0471(15) Uani 1 1 d . . . . .
H16 H 0.2283 1.3579 1.0517 0.056 Uiso 1 1 calc R . . . .
C9 C 0.3340(7) 0.9679(5) 0.7953(5) 0.0475(15) Uani 1 1 d . . . . .
H9 H 0.3099 1.0229 0.7710 0.057 Uiso 1 1 calc R . . . .
C6 C 0.1231(8) 1.0209(6) 1.2513(5) 0.0574(18) Uani 1 1 d . . . . .
H6 H 0.0973 1.0046 1.3080 0.069 Uiso 1 1 calc R . . . .
C1 C 0.2782(6) 0.9865(5) 0.9708(4) 0.0397(14) Uani 1 1 d . . . . .
C14 C 0.2428(7) 1.1589(5) 0.9443(5) 0.0466(15) Uani 1 1 d . . . . .
H14A H 0.1355 1.1648 0.9242 0.056 Uiso 1 1 calc R . . . .
H14B H 0.2734 1.1392 0.8837 0.056 Uiso 1 1 calc R . . . .
C5 C 0.1023(8) 1.1131(6) 1.2254(6) 0.0595(18) Uani 1 1 d . . . . .
H5 H 0.0649 1.1569 1.2662 0.071 Uiso 1 1 calc R . . . .
C4 C 0.1357(7) 1.1398(5) 1.1420(5) 0.0528(17) Uani 1 1 d . . . . .
H4 H 0.1207 1.2003 1.1246 0.063 Uiso 1 1 calc R . . . .
C17 C 0.5120(9) 1.5340(6) 1.1650(5) 0.0637(19) Uani 1 1 d D . . . .
H17A H 0.4228 1.5608 1.1457 0.076 Uiso 0.62(4) 1 calc R . P A 1
H17B H 0.6082 1.5825 1.1577 0.076 Uiso 0.62(4) 1 calc R . P A 1
H17C H 0.4274 1.5628 1.1403 0.076 Uiso 0.38(4) 1 calc R . P A 2
H17D H 0.6127 1.5802 1.1605 0.076 Uiso 0.38(4) 1 calc R . P A 2
C10 C 0.4209(8) 0.8808(8) 0.6537(5) 0.074(2) Uani 1 1 d D . . . .
H10A H 0.4796 0.8303 0.6501 0.089 Uiso 0.5 1 calc R . P B 1
H10B H 0.4947 0.9490 0.6549 0.089 Uiso 0.5 1 calc R . P B 1
H10C H 0.4787 0.8299 0.6481 0.089 Uiso 0.5 1 calc R . P C 2
H10D H 0.4920 0.9488 0.6524 0.089 Uiso 0.5 1 calc R . P C 2
C21 C 0.9927(19) 1.4088(9) 1.8498(11) 0.137(5) Uani 1 1 d . . . . .
H21A H 0.8978 1.4140 1.8062 0.205 Uiso 1 1 calc GR . . . .
H21B H 1.0799 1.4750 1.8674 0.205 Uiso 1 1 calc GR . . . .
H21C H 0.9701 1.3937 1.9099 0.205 Uiso 1 1 calc GR . . . .
N9 N 1.0797(14) 1.2611(9) 1.7608(10) 0.125(3) Uani 1 1 d . . . . .
C20 C 0.365(3) 1.431(3) 1.3128(16) 0.139(9) Uani 0.62(4) 1 d D U P A 1
H20A H 0.2691 1.4344 1.2691 0.209 Uiso 0.62(4) 1 calc GR . P A 1
H20B H 0.3623 1.4477 1.3813 0.209 Uiso 0.62(4) 1 calc GR . P A 1
H20C H 0.3715 1.3605 1.2946 0.209 Uiso 0.62(4) 1 calc GR . P A 1
C18 C 0.731(3) 1.4889(19) 1.3324(15) 0.103(6) Uani 0.62(4) 1 d D U P A 1
H18A H 0.7013 1.4128 1.3088 0.154 Uiso 0.62(4) 1 calc GR . P A 1
H18B H 0.7791 1.5106 1.4041 0.154 Uiso 0.62(4) 1 calc GR . P A 1
H18C H 0.8078 1.5225 1.3008 0.154 Uiso 0.62(4) 1 calc GR . P A 1
C19 C 0.586(4) 1.6644(19) 1.381(3) 0.125(10) Uani 0.62(4) 1 d D U P A 1
H19A H 0.6685 1.7158 1.3661 0.188 Uiso 0.62(4) 1 calc GR . P A 1
H19B H 0.6218 1.6649 1.4509 0.188 Uiso 0.62(4) 1 calc GR . P A 1
H19C H 0.4882 1.6822 1.3689 0.188 Uiso 0.62(4) 1 calc GR . P A 1
C22 C 1.0378(14) 1.3249(11) 1.7993(11) 0.106(4) Uani 1 1 d . . . . .
Si1 Si 0.2557(18) 0.8379(15) 0.5367(11) 0.1006(17) Uani 0.5 1 d D U P D 1
C13 C 0.093(3) 0.892(2) 0.527(2) 0.114(7) Uani 0.5 1 d D U P D 1
H13A H 0.0060 0.8465 0.5433 0.171 Uiso 0.5 1 calc GR . P D 1
H13B H 0.0561 0.8973 0.4592 0.171 Uiso 0.5 1 calc GR . P D 1
H13C H 0.1313 0.9619 0.5727 0.171 Uiso 0.5 1 calc GR . P D 1
C12 C 0.347(4) 0.867(2) 0.4388(18) 0.111(7) Uani 0.5 1 d D U P D 1
H12A H 0.4148 0.9405 0.4591 0.167 Uiso 0.5 1 calc GR . P D 1
H12B H 0.2629 0.8546 0.3776 0.167 Uiso 0.5 1 calc GR . P D 1
H12C H 0.4104 0.8219 0.4276 0.167 Uiso 0.5 1 calc GR . P D 1
C11 C 0.163(4) 0.696(2) 0.513(2) 0.168(10) Uani 0.5 1 d D U P D 1
H11A H 0.1928 0.6598 0.4592 0.251 Uiso 0.5 1 d R . P D 1
H11C H 0.1989 0.6746 0.5729 0.251 Uiso 0.5 1 d R . P D 1
H11B H 0.0471 0.6787 0.4948 0.251 Uiso 0.5 1 d R . P D 1
Si1A Si 0.2330(18) 0.8341(15) 0.5402(11) 0.1006(17) Uani 0.5 1 d D U P D 2
C13A C 0.097(3) 0.719(2) 0.571(2) 0.138(7) Uani 0.5 1 d D U P D 2
H13D H 0.0699 0.6552 0.5188 0.208 Uiso 0.5 1 calc GR . P D 2
H13E H -0.0009 0.7338 0.5757 0.208 Uiso 0.5 1 calc GR . P D 2
H13F H 0.1512 0.7108 0.6341 0.208 Uiso 0.5 1 calc GR . P D 2
C12A C 0.165(3) 0.954(2) 0.5492(19) 0.130(8) Uani 0.5 1 d D U P D 2
H12D H 0.1359 0.9688 0.6105 0.195 Uiso 0.5 1 calc GR . P D 2
H12E H 0.0722 0.9404 0.4927 0.195 Uiso 0.5 1 calc GR . P D 2
H12F H 0.2510 1.0146 0.5491 0.195 Uiso 0.5 1 calc GR . P D 2
C11A C 0.307(5) 0.797(3) 0.429(2) 0.162(13) Uani 0.5 1 d D U P D 2
H11D H 0.4211 0.8338 0.4461 0.243 Uiso 0.5 1 calc GR . P D 2
H11E H 0.2511 0.8179 0.3734 0.243 Uiso 0.5 1 calc GR . P D 2
H11F H 0.2856 0.7217 0.4106 0.243 Uiso 0.5 1 calc GR . P D 2
Si2A Si 0.532(3) 1.539(2) 1.3006(14) 0.0890(16) Uani 0.38(4) 1 d D U P A 2
C20A C 0.327(4) 1.498(4) 1.320(4) 0.138(12) Uani 0.38(4) 1 d D U P A 2
H20D H 0.2836 1.5555 1.3193 0.207 Uiso 0.38(4) 1 d R . P A 2
H20E H 0.2572 1.4366 1.2666 0.207 Uiso 0.38(4) 1 d R . P A 2
H20F H 0.3363 1.4810 1.3834 0.207 Uiso 0.38(4) 1 d R . P A 2
C18A C 0.645(6) 1.453(3) 1.344(4) 0.135(13) Uani 0.38(4) 1 d D U P A 2
H18D H 0.5704 1.3850 1.3405 0.203 Uiso 0.38(4) 1 calc GR . P A 2
H18E H 0.7114 1.4860 1.4127 0.203 Uiso 0.38(4) 1 calc GR . P A 2
H18F H 0.7132 1.4422 1.3023 0.203 Uiso 0.38(4) 1 calc GR . P A 2
C19A C 0.641(5) 1.681(2) 1.370(4) 0.084(8) Uani 0.38(4) 1 d D U P A 2
H19D H 0.7335 1.7083 1.3475 0.126 Uiso 0.38(4) 1 calc GR . P A 2
H19E H 0.6762 1.6872 1.4410 0.126 Uiso 0.38(4) 1 calc GR . P A 2
H19F H 0.5697 1.7223 1.3581 0.126 Uiso 0.38(4) 1 calc GR . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0820 0.0700 '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
Cl2 Cu1 Cl1 108.81(7) . .
N6 Cu1 Cl2 90.37(14) 2_677 .
N6 Cu1 Cl1 103.50(16) 2_677 .
N6 Cu1 N1 158.09(19) 2_677 .
N6 Cu1 N3 87.32(18) 2_677 .
N1 Cu1 Cl2 95.66(14) . .
N1 Cu1 Cl1 94.47(14) . .
N1 Cu1 N3 78.15(18) . .
N3 Cu1 Cl2 154.33(16) . .
N3 Cu1 Cl1 96.57(15) . .
C20 Si2 C17 109.3(10) . .
C18 Si2 C17 105.7(9) . .
C18 Si2 C20 111.9(11) . .
C19 Si2 C17 109.5(15) . .
C19 Si2 C20 110.6(11) . .
C19 Si2 C18 109.7(12) . .
C3 N2 C14 125.9(5) . .
C1 N2 C3 107.5(4) . .
C1 N2 C14 126.5(5) . .
N6 N7 N8 106.0(4) . .
N7 N6 Cu1 120.5(3) . 2_677
N7 N6 C15 109.7(4) . .
C15 N6 Cu1 129.6(4) . 2_677
C2 N1 Cu1 138.4(4) . .
C1 N1 Cu1 115.3(4) . .
C1 N1 C2 106.3(4) . .
N4 N3 Cu1 134.1(4) . .
N4 N3 C8 110.1(5) . .
C8 N3 Cu1 115.4(4) . .
N7 N8 C16 111.6(5) . .
N7 N8 C17 119.4(5) . .
C16 N8 C17 128.8(5) . .
N6 C15 C14 124.4(5) . .
C16 C15 N6 107.3(5) . .
C16 C15 C14 128.2(5) . .
N4 N5 C9 111.3(5) . .
N4 N5 C10 120.8(6) . .
C9 N5 C10 127.9(6) . .
N1 C2 C3 108.4(5) . .
C7 C2 N1 131.1(5) . .
C7 C2 C3 120.4(5) . .
N3 N4 N5 106.3(5) . .
N2 C3 C2 105.7(5) . .
N2 C3 C4 132.2(6) . .
C4 C3 C2 122.1(6) . .
N3 C8 C1 113.8(5) . .
C9 C8 N3 107.3(5) . .
C9 C8 C1 138.9(5) . .
C2 C7 H7 121.2 . .
C2 C7 C6 117.6(6) . .
C6 C7 H7 121.2 . .
N8 C16 C15 105.4(5) . .
N8 C16 H16 127.3 . .
C15 C16 H16 127.3 . .
N5 C9 C8 105.0(5) . .
N5 C9 H9 127.5 . .
C8 C9 H9 127.5 . .
C7 C6 H6 119.3 . .
C7 C6 C5 121.4(6) . .
C5 C6 H6 119.3 . .
N2 C1 C8 130.8(5) . .
N1 C1 N2 112.0(5) . .
N1 C1 C8 117.1(5) . .
N2 C14 C15 112.4(5) . .
N2 C14 H14A 109.1 . .
N2 C14 H14B 109.1 . .
C15 C14 H14A 109.1 . .
C15 C14 H14B 109.1 . .
H14A C14 H14B 107.8 . .
C6 C5 H5 119.1 . .
C4 C5 C6 121.8(6) . .
C4 C5 H5 119.1 . .
C3 C4 H4 121.6 . .
C5 C4 C3 116.8(6) . .
C5 C4 H4 121.6 . .
Si2 C17 H17A 109.5 . .
Si2 C17 H17B 109.5 . .
N8 C17 Si2 110.8(6) . .
N8 C17 H17A 109.5 . .
N8 C17 H17B 109.5 . .
N8 C17 H17C 108.4 . .
N8 C17 H17D 108.4 . .
N8 C17 Si2A 115.4(9) . .
H17A C17 H17B 108.1 . .
H17C C17 H17D 107.5 . .
Si2A C17 H17C 108.4 . .
Si2A C17 H17D 108.4 . .
N5 C10 H10A 107.3 . .
N5 C10 H10B 107.3 . .
N5 C10 H10C 108.8 . .
N5 C10 H10D 108.8 . .
N5 C10 Si1 119.9(7) . .
N5 C10 Si1A 113.8(7) . .
H10A C10 H10B 106.9 . .
H10C C10 H10D 107.7 . .
Si1 C10 H10A 107.3 . .
Si1 C10 H10B 107.3 . .
Si1A C10 H10C 108.8 . .
Si1A C10 H10D 108.8 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C22 C21 H21A 109.5 . .
C22 C21 H21B 109.5 . .
C22 C21 H21C 109.5 . .
Si2 C20 H20A 109.5 . .
Si2 C20 H20B 109.5 . .
Si2 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
Si2 C18 H18A 109.5 . .
Si2 C18 H18B 109.5 . .
Si2 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
Si2 C19 H19A 109.5 . .
Si2 C19 H19B 109.5 . .
Si2 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
N9 C22 C21 177.3(15) . .
C13 Si1 C10 120.3(13) . .
C13 Si1 C12 106.9(13) . .
C13 Si1 C11 105.8(13) . .
C12 Si1 C10 106.8(13) . .
C11 Si1 C10 106.7(14) . .
C11 Si1 C12 110.3(13) . .
Si1 C13 H13A 109.5 . .
Si1 C13 H13B 109.5 . .
Si1 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
Si1 C12 H12A 109.5 . .
Si1 C12 H12B 109.5 . .
Si1 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
Si1 C11 H11A 109.5 . .
Si1 C11 H11C 109.5 . .
Si1 C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11C C11 H11B 109.5 . .
C13A Si1A C10 101.7(12) . .
C12A Si1A C10 102.4(12) . .
C12A Si1A C13A 113.7(12) . .
C11A Si1A C10 104.8(16) . .
C11A Si1A C13A 115.6(13) . .
C11A Si1A C12A 115.9(13) . .
Si1A C13A H13D 109.5 . .
Si1A C13A H13E 109.5 . .
Si1A C13A H13F 109.5 . .
H13D C13A H13E 109.5 . .
H13D C13A H13F 109.5 . .
H13E C13A H13F 109.5 . .
Si1A C12A H12D 109.5 . .
Si1A C12A H12E 109.5 . .
Si1A C12A H12F 109.5 . .
H12D C12A H12E 109.5 . .
H12D C12A H12F 109.5 . .
H12E C12A H12F 109.5 . .
Si1A C11A H11D 109.5 . .
Si1A C11A H11E 109.5 . .
Si1A C11A H11F 109.5 . .
H11D C11A H11E 109.5 . .
H11D C11A H11F 109.5 . .
H11E C11A H11F 109.5 . .
C20A Si2A C17 110(2) . .
C18A Si2A C17 111.5(19) . .
C18A Si2A C20A 109.8(16) . .
C18A Si2A C19A 111.1(17) . .
C19A Si2A C17 105(2) . .
C19A Si2A C20A 109.0(15) . .
Si2A C20A H20D 109.6 . .
Si2A C20A H20E 109.3 . .
Si2A C20A H20F 109.5 . .
H20D C20A H20E 109.5 . .
H20D C20A H20F 109.5 . .
H20E C20A H20F 109.5 . .
Si2A C18A H18D 109.5 . .
Si2A C18A H18E 109.5 . .
Si2A C18A H18F 109.5 . .
H18D C18A H18E 109.5 . .
H18D C18A H18F 109.5 . .
H18E C18A H18F 109.5 . .
Si2A C19A H19D 109.5 . .
Si2A C19A H19E 109.5 . .
Si2A C19A H19F 109.5 . .
H19D C19A H19E 109.5 . .
H19D C19A H19F 109.5 . .
H19E C19A H19F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl2 2.2726(17) .
Cu1 Cl1 2.3944(18) .
Cu1 N6 2.030(4) 2_677
Cu1 N1 2.053(4) .
Cu1 N3 2.075(5) .
Si2 C17 1.882(13) .
Si2 C20 1.867(15) .
Si2 C18 1.864(15) .
Si2 C19 1.859(15) .
N2 C3 1.385(8) .
N2 C1 1.348(7) .
N2 C14 1.469(7) .
N7 N6 1.314(7) .
N7 N8 1.319(7) .
N6 Cu1 2.030(4) 2_677
N6 C15 1.355(7) .
N1 C2 1.381(7) .
N1 C1 1.337(7) .
N3 N4 1.295(7) .
N3 C8 1.361(7) .
N8 C16 1.339(8) .
N8 C17 1.466(8) .
C15 C16 1.344(8) .
C15 C14 1.519(9) .
N5 N4 1.338(7) .
N5 C9 1.341(8) .
N5 C10 1.458(8) .
C2 C3 1.416(8) .
C2 C7 1.376(8) .
C3 C4 1.387(9) .
C8 C9 1.356(8) .
C8 C1 1.442(8) .
C7 H7 0.9300 .
C7 C6 1.383(9) .
C16 H16 0.9300 .
C9 H9 0.9300 .
C6 H6 0.9300 .
C6 C5 1.409(10) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C5 H5 0.9300 .
C5 C4 1.367(10) .
C4 H4 0.9300 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 H17C 0.9700 .
C17 H17D 0.9700 .
C17 Si2A 1.869(19) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 H10C 0.9700 .
C10 H10D 0.9700 .
C10 Si1 1.825(15) .
C10 Si1A 1.906(15) .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C21 C22 1.428(18) .
N9 C22 1.130(15) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
Si1 C13 1.790(16) .
Si1 C12 1.810(16) .
Si1 C11 1.798(18) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C11 H11A 0.9601 .
C11 H11C 0.9600 .
C11 H11B 0.9600 .
Si1A C13A 1.881(18) .
Si1A C12A 1.877(18) .
Si1A C11A 1.873(18) .
C13A H13D 0.9600 .
C13A H13E 0.9600 .
C13A H13F 0.9600 .
C12A H12D 0.9600 .
C12A H12E 0.9600 .
C12A H12F 0.9600 .
C11A H11D 0.9600 .
C11A H11E 0.9600 .
C11A H11F 0.9600 .
Si2A C20A 1.86(2) .
Si2A C18A 1.85(2) .
Si2A C19A 1.86(2) .
C20A H20D 0.9601 .
C20A H20E 0.9600 .
C20A H20F 0.9599 .
C18A H18D 0.9600 .
C18A H18E 0.9600 .
C18A H18F 0.9600 .
C19A H19D 0.9600 .
C19A H19E 0.9600 .
C19A H19F 0.9600 .
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
Cu1 N6 C15 C16 176.8(4) 2_677 .
Cu1 N6 C15 C14 -6.6(8) 2_677 .
Cu1 N1 C2 C3 -179.8(4) . .
Cu1 N1 C2 C7 -3.0(10) . .
Cu1 N1 C1 N2 -178.3(4) . .
Cu1 N1 C1 C8 2.3(6) . .
Cu1 N3 N4 N5 172.3(4) . .
Cu1 N3 C8 C9 -173.1(4) . .
Cu1 N3 C8 C1 4.8(6) . .
N2 C3 C4 C5 179.6(6) . .
N7 N6 C15 C16 1.3(6) . .
N7 N6 C15 C14 177.9(5) . .
N7 N8 C16 C15 1.0(7) . .
N7 N8 C17 Si2 -85.0(8) . .
N7 N8 C17 Si2A -90.1(11) . .
N6 N7 N8 C16 -0.2(6) . .
N6 N7 N8 C17 175.3(5) . .
N6 C15 C16 N8 -1.3(6) . .
N6 C15 C14 N2 76.7(7) . .
N1 C2 C3 N2 -1.4(6) . .
N1 C2 C3 C4 178.6(5) . .
N1 C2 C7 C6 -177.5(6) . .
N3 C8 C9 N5 -1.5(6) . .
N3 C8 C1 N2 176.1(5) . .
N3 C8 C1 N1 -4.8(7) . .
N8 N7 N6 Cu1 -176.6(3) . 2_677
N8 N7 N6 C15 -0.7(6) . .
N8 C17 Si2A C20A -80.1(18) . .
N8 C17 Si2A C18A 42(2) . .
N8 C17 Si2A C19A 162.5(15) . .
N5 C10 Si1 C13 42.9(17) . .
N5 C10 Si1 C12 164.7(11) . .
N5 C10 Si1 C11 -77.5(14) . .
C2 N1 C1 N2 2.1(6) . .
C2 N1 C1 C8 -177.3(5) . .
C2 C3 C4 C5 -0.5(9) . .
C2 C7 C6 C5 -0.2(10) . .
N4 N3 C8 C9 1.4(7) . .
N4 N3 C8 C1 179.3(5) . .
N4 N5 C9 C8 1.1(7) . .
N4 N5 C10 Si1 110.1(10) . .
N4 N5 C10 Si1A 109.5(9) . .
C3 N2 C1 N1 -3.0(6) . .
C3 N2 C1 C8 176.2(6) . .
C3 N2 C14 C15 61.1(7) . .
C3 C2 C7 C6 -1.1(9) . .
C8 N3 N4 N5 -0.7(6) . .
C7 C2 C3 N2 -178.6(5) . .
C7 C2 C3 C4 1.5(9) . .
C7 C6 C5 C4 1.1(11) . .
C16 N8 C17 Si2 89.6(9) . .
C16 N8 C17 Si2A 84.5(12) . .
C16 C15 C14 N2 -107.4(6) . .
C9 N5 N4 N3 -0.3(6) . .
C9 N5 C10 Si1 -70.7(12) . .
C9 N5 C10 Si1A -71.3(11) . .
C9 C8 C1 N2 -7.0(12) . .
C9 C8 C1 N1 172.2(7) . .
C6 C5 C4 C3 -0.8(10) . .
C1 N2 C3 C2 2.6(6) . .
C1 N2 C3 C4 -177.4(6) . .
C1 N2 C14 C15 -117.0(6) . .
C1 N1 C2 C3 -0.3(6) . .
C1 N1 C2 C7 176.5(6) . .
C1 C8 C9 N5 -178.6(7) . .
C14 N2 C3 C2 -175.8(5) . .
C14 N2 C3 C4 4.1(10) . .
C14 N2 C1 N1 175.4(5) . .
C14 N2 C1 C8 -5.4(9) . .
C14 C15 C16 N8 -177.8(5) . .
C17 N8 C16 C15 -174.0(6) . .
C10 N5 N4 N3 179.0(6) . .
C10 N5 C9 C8 -178.2(6) . .
C20 Si2 C17 N8 -56.5(13) . .
C18 Si2 C17 N8 64.1(12) . .
C19 Si2 C17 N8 -177.7(12) . .
