#------------------------------------------------------------------------------
#$Date: 2025-12-05 01:45:59 +0100 (Fri 05 de Dec de 2025) $
#$Revision: 304042 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/99/7719980.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_7719980
loop_
_publ_author_name
'Kumawat, Manoj Kumar'
'Mathur, Shobhit'
'Rathnam, Sharan Shanmuga Vuppaladadium'
'Jangra, Jitender'
'Roy, Anindya'
'Maji, Somnath'
_publ_section_title
;
 Comprehensive Design, Synthesis of Methyl Substituted Benzimidazole-based
 Mononuclear Copper(II) Complexes and Evaluation of DNA Cleavage and
 ROS-induced Apoptosis
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D5DT02281A
_journal_year                    2026
_chemical_formula_moiety         'C32 H31 Cu N7, 2(Cl O4)'
_chemical_formula_sum            'C32 H31 Cl2 Cu N7 O8'
_chemical_formula_weight         776.096
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-08-25 deposited with the CCDC.	2025-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.252(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2663(7)
_cell_length_b                   20.2627(18)
_cell_length_c                   10.2878(10)
_cell_measurement_reflns_used    9269
_cell_measurement_temperature    172.00
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.22
_cell_volume                     1720.4(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      172.00
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15979
_diffrn_reflns_point_group_measured_fraction_full 0.9431
_diffrn_reflns_point_group_measured_fraction_max 0.9210
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         2.01
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.6567.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             799.834
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.5350
_refine_diff_density_min         -0.3936
_refine_diff_density_rms         0.0713
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.027(9)
_refine_ls_d_res_high            0.7788
_refine_ls_d_res_low             10.1314
_refine_ls_goodness_of_fit_ref   1.0251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    61
_refine_ls_number_parameters     466
_refine_ls_number_reflns         7030
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.0237
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0904P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.841
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              25
_reflns_limit_k_min              -25
_reflns_limit_l_max              13
_reflns_limit_l_min              -13
_reflns_number_gt                6046
_reflns_number_total             7030
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5dt02281a2.cif
_cod_data_source_block           mo_SNM_MKK_MePHENCu_0m
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7719980
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.970(15)
 0.030(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 Cu1-N8 \\sim Cu1-N1
 with sigma of 0.02
 C1-N8 \\sim C1-N1
 with sigma of 0.02
 C9-N8 \\sim C9-N1
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
N8: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
N1: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
Uanis(N8) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Sof(H1bc)=Sof(H1bd)=Sof(H9bc)=Sof(H9bd)=Sof(N1)=Sof(H1)=1-FVAR(1)
 Sof(H1aa)=Sof(H1ab)=Sof(H9aa)=Sof(H9ab)=Sof(N8)=Sof(H8)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 N8(H8), N1(H1)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1aa,H1ab), C1(H1bc,H1bd), C9(H9aa,H9ab), C9(H9bc,H9bd)
6.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C7(H7), C27(H27), C4(H4), C13(H13), C20(H20), C12(H12), C19(H19),
 C23(H23), C14(H14), C6(H6), C15(H15), C5(H5), C22(H22)
6.d Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C30(H30a,H30b,H30c), C18(H18a,H18b,H18c), C32(H32a,H32b,
 H32c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
Cu1 Cu 0.41137(5) 0.43841(3) 0.38663(4) 0.04375(13) Uani 1.000000 D . . .
Cl1 Cl 0.93875(15) 0.28126(7) 0.58387(13) 0.0743(3) Uani 1.000000 . . . .
Cl2 Cl 0.23866(18) 0.22023(8) 0.09800(17) 0.0886(4) Uani 1.000000 . . . .
N2 N 0.3220(4) 0.45278(15) 0.5585(3) 0.0499(8) Uani 1.000000 . . . .
N5 N 0.5299(4) 0.53128(15) 0.3731(3) 0.0494(7) Uani 1.000000 . . . .
N6 N 0.2639(5) 0.41126(19) 0.7486(3) 0.0559(8) Uani 1.000000 . . . .
N4 N 0.2337(4) 0.49298(16) 0.2769(3) 0.0503(7) Uani 1.000000 . . . .
N7 N 0.6570(4) 0.31053(17) 0.1741(4) 0.0558(8) Uani 1.000000 . . . .
N3 N 0.5174(4) 0.39631(15) 0.2399(3) 0.0476(7) Uani 1.000000 . . . .
C3 C 0.6643(5) 0.3576(2) 0.0786(4) 0.0531(9) Uani 1.000000 . . . .
C8 C 0.5758(4) 0.4123(2) 0.1215(4) 0.0501(9) Uani 1.000000 . . . .
C16 C 0.2405(5) 0.5011(2) 0.6221(4) 0.0507(8) Uani 1.000000 . . . .
C26 C 0.4403(5) 0.57465(17) 0.2972(4) 0.0504(9) Uani 1.000000 . . . .
C10 C 0.3349(5) 0.4013(2) 0.6362(4) 0.0523(9) Uani 1.000000 . . . .
C25 C 0.2817(5) 0.55546(19) 0.2512(4) 0.0516(9) Uani 1.000000 . . . .
C24 C 0.1791(6) 0.5998(2) 0.1823(4) 0.0595(10) Uani 1.000000 . . . .
C28 C -0.0246(7) 0.5170(4) 0.1720(6) 0.0879(17) Uani 1.000000 . . . .
H28 H -0.1320(7) 0.5032(4) 0.1482(6) 0.106(2) Uiso 1.000000 R . . .
C11 C 0.1996(6) 0.4752(2) 0.7438(4) 0.0560(10) Uani 1.000000 . . . .
C7 C 0.5585(6) 0.4686(2) 0.0457(4) 0.0615(11) Uani 1.000000 . . . .
H7 H 0.4989(6) 0.5057(2) 0.0729(4) 0.0738(13) Uiso 1.000000 R . . .
C27 C 0.0218(7) 0.5777(3) 0.1447(5) 0.0775(15) Uani 1.000000 . . . .
H27 H -0.0519(7) 0.6066(3) 0.0991(5) 0.0930(18) Uiso 1.000000 R . . .
C4 C 0.7390(6) 0.3583(3) -0.0399(5) 0.0725(13) Uani 1.000000 . . . .
H4 H 0.7997(6) 0.3217(3) -0.0679(5) 0.0870(16) Uiso 1.000000 R . . .
C2 C 0.5686(5) 0.33531(18) 0.2678(4) 0.0475(8) Uani 1.000000 . . . .
C29 C 0.0853(6) 0.4726(3) 0.2367(5) 0.0669(12) Uani 1.000000 . . . .
C31 C 0.2570(8) 0.3659(3) 0.8576(5) 0.0786(15) Uani 1.000000 . . . .
H31a H 0.316(5) 0.3255(10) 0.839(2) 0.118(2) Uiso 1.000000 GR . . .
H31b H 0.306(5) 0.3866(9) 0.9363(11) 0.118(2) Uiso 1.000000 GR . . .
H31c H 0.1437(9) 0.3550(18) 0.871(3) 0.118(2) Uiso 1.000000 GR . . .
C13 C 0.0644(8) 0.5730(3) 0.7952(6) 0.0861(16) Uani 1.000000 . . . .
H13 H 0.0021(8) 0.5982(3) 0.8519(6) 0.103(2) Uiso 1.000000 R . . .
C20 C 0.6547(8) 0.6529(2) 0.3112(6) 0.0824(15) Uani 1.000000 . . . .
H20 H 0.7022(8) 0.6937(2) 0.2885(6) 0.0988(18) Uiso 1.000000 R . . .
C12 C 0.1143(7) 0.5113(3) 0.8322(5) 0.0776(14) Uani 1.000000 . . . .
H12 H 0.0916(7) 0.4937(3) 0.9149(5) 0.0931(17) Uiso 1.000000 R . . .
C1 C 0.5221(6) 0.3012(2) 0.3889(4) 0.0567(10) Uani 1.000000 D . . .
H1aa H 0.4771(6) 0.2570(2) 0.3672(4) 0.0680(11) Uiso 0.593(12) R . P 1
H1ab H 0.6186(6) 0.2955(2) 0.4493(4) 0.0680(11) Uiso 0.593(12) R . P 1
H1bc H 0.4174(6) 0.2779(2) 0.3742(4) 0.0680(11) Uiso 0.407(12) R . P 2
H1bd H 0.6060(6) 0.2689(2) 0.4189(4) 0.0680(11) Uiso 0.407(12) R . P 2
C19 C 0.7401(7) 0.6104(3) 0.3892(6) 0.0831(15) Uani 1.000000 . . . .
H19 H 0.8456(7) 0.6223(3) 0.4225(6) 0.0997(18) Uiso 1.000000 R . . .
C23 C 0.2362(8) 0.6636(3) 0.1508(6) 0.0804(16) Uani 1.000000 . . . .
H23 H 0.1670(8) 0.6940(3) 0.1045(6) 0.0964(19) Uiso 1.000000 R . . .
C9 C 0.4150(7) 0.3393(2) 0.5952(5) 0.0653(11) Uani 1.000000 D . . .
H9aa H 0.5298(7) 0.3382(2) 0.6281(5) 0.0783(14) Uiso 0.593(12) R . P 1
H9ab H 0.3589(7) 0.3001(2) 0.6284(5) 0.0783(14) Uiso 0.593(12) R . P 1
H9bc H 0.4866(7) 0.3218(2) 0.6675(5) 0.0783(14) Uiso 0.407(12) R . P 2
H9bd H 0.3323(7) 0.3054(2) 0.5710(5) 0.0783(14) Uiso 0.407(12) R . P 2
O3 O 0.8450(8) 0.2263(3) 0.5391(7) 0.137(2) Uani 1.000000 . . . .
C17 C 0.6755(6) 0.5487(2) 0.4221(5) 0.0681(12) Uani 1.000000 . . . .
C14 C 0.1031(7) 0.6001(2) 0.6745(5) 0.0703(12) Uani 1.000000 . . . .
H14 H 0.0674(7) 0.6435(2) 0.6522(5) 0.0844(15) Uiso 1.000000 R . . .
C21 C 0.4978(7) 0.6378(2) 0.2635(5) 0.0662(12) Uani 1.000000 . . . .
C6 C 0.6331(7) 0.4681(3) -0.0730(5) 0.0768(14) Uani 1.000000 . . . .
H6 H 0.6238(7) 0.5058(3) -0.1278(5) 0.0921(17) Uiso 1.000000 R . . .
C30 C 0.0405(9) 0.4022(4) 0.2630(8) 0.106(2) Uani 1.000000 . . . .
H30a H 0.1389(11) 0.3767(8) 0.285(6) 0.160(4) Uiso 1.000000 GR . . .
H30b H -0.031(6) 0.4006(5) 0.336(4) 0.160(4) Uiso 1.000000 GR . . .
H30c H -0.016(7) 0.3833(10) 0.185(2) 0.160(4) Uiso 1.000000 GR . . .
C15 C 0.1912(5) 0.5652(2) 0.5886(4) 0.0571(10) Uani 1.000000 . . . .
H15 H 0.2182(5) 0.5842(2) 0.5082(4) 0.0685(11) Uiso 1.000000 R . . .
C5 C 0.7209(7) 0.4136(3) -0.1128(5) 0.0788(15) Uani 1.000000 . . . .
H5 H 0.7697(7) 0.4155(3) -0.1941(5) 0.0946(18) Uiso 1.000000 R . . .
C18 C 0.7649(8) 0.4991(4) 0.5064(7) 0.097(2) Uani 1.000000 . . . .
H18a H 0.6878(11) 0.4748(19) 0.557(4) 0.145(3) Uiso 1.000000 GR . . .
H18b H 0.822(5) 0.4681(17) 0.4516(8) 0.145(3) Uiso 1.000000 GR . . .
H18c H 0.844(5) 0.5217(4) 0.565(4) 0.145(3) Uiso 1.000000 GR . . .
C22 C 0.3908(9) 0.6805(2) 0.1875(6) 0.0806(16) Uani 1.000000 . . . .
H22 H 0.4300(9) 0.7223(2) 0.1620(6) 0.0967(19) Uiso 1.000000 R . . .
C32 C 0.7263(7) 0.2432(3) 0.1733(6) 0.0806(15) Uani 1.000000 . . . .
H32a H 0.674(4) 0.2178(8) 0.101(3) 0.121(2) Uiso 1.000000 GR . . .
H32b H 0.8431(12) 0.2459(3) 0.162(5) 0.121(2) Uiso 1.000000 GR . . .
H32c H 0.708(5) 0.2212(9) 0.2560(19) 0.121(2) Uiso 1.000000 GR . . .
O7 O 0.0898(7) 0.2237(5) 0.0372(8) 0.177(3) Uani 1.000000 . . . .
O1 O 0.8471(12) 0.3285(5) 0.6129(15) 0.292(9) Uani 1.000000 . . . .
O8 O 0.3423(12) 0.2631(5) 0.0687(12) 0.278(8) Uani 1.000000 . . . .
O2 O 1.0320(11) 0.2609(4) 0.6913(10) 0.199(4) Uani 1.000000 . . . .
O4 O 1.0751(12) 0.2875(6) 0.5107(15) 0.274(7) Uani 1.000000 . . . .
O5 O 0.252(2) 0.2052(7) 0.2227(9) 0.322(10) Uani 1.000000 . . . .
O6 O 0.2836(17) 0.1548(5) 0.0708(19) 0.283(7) Uani 1.000000 . . . .
N8 N 0.4024(7) 0.3407(3) 0.4497(5) 0.0476(18) Uani 0.593(12) D U P 1
H8 H 0.3010(7) 0.3240(3) 0.4230(5) 0.057(2) Uiso 0.593(12) R . P 1
N1 N 0.5089(10) 0.3546(4) 0.4843(7) 0.048(3) Uani 0.407(12) D U P 2
H1 H 0.6133(10) 0.3653(4) 0.5159(7) 0.058(3) Uiso 0.407(12) R . P 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Cl 0.14908 0.15974 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Cu 0.32831 1.27084 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19100 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
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
N5 Cu1 N2 97.17(12) . . ?
N4 Cu1 N2 96.73(13) . . ?
N4 Cu1 N5 79.12(13) . . ?
N3 Cu1 N2 161.66(12) . . ?
N3 Cu1 N5 96.08(12) . . ?
N3 Cu1 N4 98.18(13) . . ?
N8 Cu1 N2 80.77(17) . . ?
N8 Cu1 N5 152.07(18) . . ?
N8 Cu1 N4 128.81(18) . . ?
N8 Cu1 N3 81.57(17) . . ?
N1 Cu1 N2 81.1(2) . . ?
N1 Cu1 N5 125.3(2) . . ?
N1 Cu1 N4 155.6(2) . . ?
N1 Cu1 N3 80.9(2) . . ?
N1 Cu1 N8 26.8(2) . . ?
O1 Cl1 O3 110.3(5) . . ?
O2 Cl1 O3 107.2(5) . . ?
O2 Cl1 O1 110.6(8) . . ?
O4 Cl1 O3 109.8(7) . . ?
O4 Cl1 O1 124.8(9) . . ?
O4 Cl1 O2 91.6(8) . . ?
O8 Cl2 O7 117.6(6) . . ?
O5 Cl2 O7 119.1(8) . . ?
O5 Cl2 O8 111.7(7) . . ?
O6 Cl2 O7 101.6(7) . . ?
O6 Cl2 O8 114.1(9) . . ?
O6 Cl2 O5 88.2(10) . . ?
C16 N2 Cu1 138.5(3) . . ?
C10 N2 Cu1 114.0(3) . . ?
C10 N2 C16 107.4(3) . . ?
C26 N5 Cu1 111.7(3) . . ?
C17 N5 Cu1 128.5(3) . . ?
C17 N5 C26 119.8(4) . . ?
C11 N6 C10 107.0(3) . . ?
C31 N6 C10 127.5(4) . . ?
C31 N6 C11 125.5(4) . . ?
C25 N4 Cu1 113.0(3) . . ?
C29 N4 Cu1 126.9(3) . . ?
C29 N4 C25 120.1(4) . . ?
C2 N7 C3 107.6(3) . . ?
C32 N7 C3 127.2(4) . . ?
C32 N7 C2 125.2(4) . . ?
C8 N3 Cu1 140.1(3) . . ?
C2 N3 Cu1 112.6(3) . . ?
C2 N3 C8 106.6(3) . . ?
C8 C3 N7 106.1(3) . . ?
C4 C3 N7 132.1(4) . . ?
C4 C3 C8 121.8(4) . . ?
C3 C8 N3 107.8(4) . . ?
C7 C8 N3 131.5(4) . . ?
C7 C8 C3 120.6(4) . . ?
C11 C16 N2 107.8(4) . . ?
C15 C16 N2 133.4(4) . . ?
C15 C16 C11 118.7(4) . . ?
C25 C26 N5 118.3(3) . . ?
C21 C26 N5 122.9(4) . . ?
C21 C26 C25 118.8(4) . . ?
N6 C10 N2 112.4(4) . . ?
C9 C10 N2 121.2(3) . . ?
C9 C10 N6 126.4(4) . . ?
C26 C25 N4 117.7(3) . . ?
C24 C25 N4 121.5(4) . . ?
C24 C25 C26 120.9(4) . . ?
C27 C24 C25 117.2(4) . . ?
C23 C24 C25 120.0(5) . . ?
C23 C24 C27 122.8(5) . . ?
C27 C28 H28 119.9(4) . . ?
C29 C28 H28 119.9(4) . . ?
C29 C28 C27 120.3(6) . . ?
C16 C11 N6 105.3(4) . . ?
C12 C11 N6 132.0(4) . . ?
C12 C11 C16 122.7(5) . . ?
H7 C7 C8 121.7(2) . . ?
C6 C7 C8 116.7(5) . . ?
C6 C7 H7 121.7(3) . . ?
C28 C27 C24 120.8(5) . . ?
H27 C27 C24 119.6(3) . . ?
H27 C27 C28 119.6(4) . . ?
H4 C4 C3 121.6(3) . . ?
C5 C4 C3 116.8(5) . . ?
C5 C4 H4 121.6(3) . . ?
N3 C2 N7 111.9(4) . . ?
C1 C2 N7 127.1(3) . . ?
C1 C2 N3 121.0(3) . . ?
C28 C29 N4 120.0(5) . . ?
C30 C29 N4 118.0(5) . . ?
C30 C29 C28 122.0(6) . . ?
H31a C31 N6 109.5 . . ?
H31b C31 N6 109.5 . . ?
H31b C31 H31a 109.5 . . ?
H31c C31 N6 109.5 . . ?
H31c C31 H31a 109.5 . . ?
H31c C31 H31b 109.5 . . ?
C12 C13 H13 119.2(3) . . ?
C14 C13 H13 119.2(3) . . ?
C14 C13 C12 121.6(5) . . ?
C19 C20 H20 119.5(3) . . ?
C21 C20 H20 119.5(3) . . ?
C21 C20 C19 120.9(5) . . ?
C13 C12 C11 117.1(5) . . ?
H12 C12 C11 121.4(3) . . ?
H12 C12 C13 121.4(3) . . ?
H1aa C1 C2 110.0(2) . . ?
H1ab C1 C2 110.0(2) . . ?
H1ab C1 H1aa 108.3 . . ?
H1bc C1 C2 110.9(2) . . ?
H1bc C1 H1aa 38.8 . . ?
H1bc C1 H1ab 135.0 . . ?
H1bd C1 C2 110.9(2) . . ?
H1bd C1 H1aa 73.8 . . ?
H1bd C1 H1ab 37.0 . . ?
H1bd C1 H1bc 108.9 . . ?
N8 C1 C2 108.7(4) . . ?
N8 C1 H1aa 110.0(3) . . ?
N8 C1 H1ab 110.0(3) . . ?
N8 C1 H1bc 73.5(3) . . ?
N8 C1 H1bd 135.8(3) . . ?
N1 C1 C2 104.4(4) . . ?
N1 C1 H1aa 140.9(4) . . ?
N1 C1 H1ab 75.8(4) . . ?
N1 C1 H1bc 110.9(4) . . ?
N1 C1 H1bd 110.9(4) . . ?
N1 C1 N8 39.0(4) . . ?
H19 C19 C20 119.4(3) . . ?
C17 C19 C20 121.1(5) . . ?
C17 C19 H19 119.4(3) . . ?
H23 C23 C24 120.5(3) . . ?
C22 C23 C24 119.1(5) . . ?
C22 C23 H23 120.5(3) . . ?
H9aa C9 C10 110.7(3) . . ?
H9ab C9 C10 110.7(2) . . ?
H9ab C9 H9aa 108.8 . . ?
H9bc C9 C10 110.1(2) . . ?
H9bc C9 H9aa 38.2 . . ?
H9bc C9 H9ab 74.1 . . ?
H9bd C9 C10 110.1(3) . . ?
H9bd C9 H9aa 134.9 . . ?
H9bd C9 H9ab 37.0 . . ?
H9bd C9 H9bc 108.4 . . ?
N8 C9 C10 105.1(4) . . ?
N8 C9 H9aa 110.7(3) . . ?
N8 C9 H9ab 110.7(3) . . ?
N8 C9 H9bc 139.9(3) . . ?
N8 C9 H9bd 75.7(3) . . ?
N1 C9 C10 107.9(4) . . ?
N1 C9 H9aa 74.2(4) . . ?
N1 C9 H9ab 136.6(4) . . ?
N1 C9 H9bc 110.1(4) . . ?
N1 C9 H9bd 110.1(4) . . ?
N1 C9 N8 38.6(4) . . ?
C19 C17 N5 119.6(5) . . ?
C18 C17 N5 116.6(5) . . ?
C18 C17 C19 123.7(5) . . ?
H14 C14 C13 119.3(3) . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.3(3) . . ?
C20 C21 C26 115.6(5) . . ?
C22 C21 C26 118.2(5) . . ?
C22 C21 C20 126.2(5) . . ?
H6 C6 C7 119.2(3) . . ?
C5 C6 C7 121.7(5) . . ?
C5 C6 H6 119.2(3) . . ?
H30a C30 C29 109.5 . . ?
H30b C30 C29 109.5 . . ?
H30b C30 H30a 109.5 . . ?
H30c C30 C29 109.5 . . ?
H30c C30 H30a 109.5 . . ?
H30c C30 H30b 109.5 . . ?
C14 C15 C16 118.5(4) . . ?
H15 C15 C16 120.7(2) . . ?
H15 C15 C14 120.7(3) . . ?
C6 C5 C4 122.4(4) . . ?
H5 C5 C4 118.8(3) . . ?
H5 C5 C6 118.8(3) . . ?
H18a C18 C17 109.5 . . ?
H18b C18 C17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C21 C22 C23 122.8(5) . . ?
H22 C22 C23 118.6(3) . . ?
H22 C22 C21 118.6(3) . . ?
H32a C32 N7 109.5 . . ?
H32b C32 N7 109.5 . . ?
H32b C32 H32a 109.5 . . ?
H32c C32 N7 109.5 . . ?
H32c C32 H32a 109.5 . . ?
H32c C32 H32b 109.5 . . ?
C1 N8 Cu1 110.7(3) . . ?
C9 N8 Cu1 109.1(3) . . ?
C9 N8 C1 114.4(4) . . ?
H8 N8 Cu1 107.43(16) . . ?
H8 N8 C1 107.4(3) . . ?
H8 N8 C9 107.4(3) . . ?
C1 N1 Cu1 108.4(5) . . ?
C9 N1 Cu1 109.9(5) . . ?
C9 N1 C1 115.5(6) . . ?
H1 N1 Cu1 107.6(2) . . ?
H1 N1 C1 107.6(4) . . ?
H1 N1 C9 107.6(4) . . ?
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 N2 1.976(3) . ?
Cu1 N5 2.130(3) . ?
Cu1 N4 2.113(3) . ?
Cu1 N3 1.981(3) . ?
Cu1 N8 2.087(5) . ?
Cu1 N1 2.109(8) . ?
Cl1 O3 1.419(6) . ?
Cl1 O1 1.267(7) . ?
Cl1 O2 1.374(8) . ?
Cl1 O4 1.397(8) . ?
Cl2 O7 1.350(6) . ?
Cl2 O8 1.268(7) . ?
Cl2 O5 1.317(9) . ?
Cl2 O6 1.409(11) . ?
N2 C16 1.374(5) . ?
N2 C10 1.315(5) . ?
N5 C26 1.366(5) . ?
N5 C17 1.326(6) . ?
N6 C10 1.341(5) . ?
N6 C11 1.401(6) . ?
N6 C31 1.454(6) . ?
N4 C25 1.357(5) . ?
N4 C29 1.338(6) . ?
N7 C3 1.373(6) . ?
N7 C2 1.339(5) . ?
N7 C32 1.480(6) . ?
N3 C8 1.374(5) . ?
N3 C2 1.332(5) . ?
C3 C8 1.412(6) . ?
C3 C4 1.398(6) . ?
C8 C7 1.385(6) . ?
C16 C11 1.415(6) . ?
C16 C15 1.400(6) . ?
C26 C25 1.422(6) . ?
C26 C21 1.415(5) . ?
C10 C9 1.493(6) . ?
C25 C24 1.401(6) . ?
C24 C27 1.409(8) . ?
C24 C23 1.419(8) . ?
C28 H28 0.9500 . ?
C28 C27 1.322(9) . ?
C28 C29 1.418(9) . ?
C11 C12 1.390(7) . ?
C7 H7 0.9500 . ?
C7 C6 1.399(7) . ?
C27 H27 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.352(8) . ?
C2 C1 1.495(6) . ?
C29 C30 1.502(9) . ?
C31 H31a 0.9800 . ?
C31 H31b 0.9800 . ?
C31 H31c 0.9800 . ?
C13 H13 0.9500 . ?
C13 C12 1.363(9) . ?
C13 C14 1.411(8) . ?
C20 H20 0.9500 . ?
C20 C19 1.349(9) . ?
C20 C21 1.395(8) . ?
C12 H12 0.9500 . ?
C1 H1aa 0.9900 . ?
C1 H1ab 0.9900 . ?
C1 H1bc 0.9900 . ?
C1 H1bd 0.9900 . ?
C1 N8 1.443(7) . ?
C1 N1 1.469(9) . ?
C19 H19 0.9500 . ?
C19 C17 1.408(7) . ?
C23 H23 0.9500 . ?
C23 C22 1.356(9) . ?
C9 H9aa 0.9900 . ?
C9 H9ab 0.9900 . ?
C9 H9bc 0.9900 . ?
C9 H9bd 0.9900 . ?
C9 N8 1.494(7) . ?
C9 N1 1.450(9) . ?
C17 C18 1.496(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.373(6) . ?
C21 C22 1.436(8) . ?
C6 H6 0.9500 . ?
C6 C5 1.394(8) . ?
C30 H30a 0.9800 . ?
C30 H30b 0.9800 . ?
C30 H30c 0.9800 . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C22 H22 0.9500 . ?
C32 H32a 0.9800 . ?
C32 H32b 0.9800 . ?
C32 H32c 0.9800 . ?
N8 H8 0.9300 . ?
N1 H1 0.9300 . ?
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
_geom_torsion_publ_flag
Cu1 N2 C16 C11 174.5(4) . . . . ?
Cu1 N2 C16 C15 -3.5(5) . . . . ?
Cu1 N2 C10 N6 -176.0(3) . . . . ?
Cu1 N2 C10 C9 1.5(4) . . . . ?
Cu1 N5 C26 C25 6.2(3) . . . . ?
Cu1 N5 C26 C21 -174.4(3) . . . . ?
Cu1 N5 C17 C19 172.5(4) . . . . ?
Cu1 N5 C17 C18 -5.1(4) . . . . ?
Cu1 N4 C25 C26 1.4(3) . . . . ?
Cu1 N4 C25 C24 -178.4(2) . . . . ?
Cu1 N4 C29 C28 175.2(4) . . . . ?
Cu1 N4 C29 C30 -4.5(5) . . . . ?
Cu1 N3 C8 C3 169.3(4) . . . . ?
Cu1 N3 C8 C7 -11.9(5) . . . . ?
Cu1 N3 C2 N7 -172.4(3) . . . . ?
Cu1 N3 C2 C1 9.7(3) . . . . ?
Cu1 N8 C1 C2 -21.0(4) . . . . ?
Cu1 N8 C1 N1 68.9(7) . . . . ?
Cu1 N8 C9 C10 32.1(3) . . . . ?
Cu1 N8 C9 N1 -67.8(7) . . . . ?
Cu1 N1 C1 C2 36.5(4) . . . . ?
Cu1 N1 C1 N8 -65.5(7) . . . . ?
Cu1 N1 C9 C10 -24.9(5) . . . . ?
Cu1 N1 C9 N8 67.0(7) . . . . ?
N2 C16 C11 N6 1.4(4) . . . . ?
N2 C16 C11 C12 -179.2(4) . . . . ?
N2 C16 C15 C14 176.9(5) . . . . ?
N2 C10 N6 C11 -0.4(4) . . . . ?
N2 C10 N6 C31 -178.8(4) . . . . ?
N2 C10 C9 N8 -23.5(5) . . . . ?
N2 C10 C9 N1 16.7(5) . . . . ?
N5 C26 C25 N4 -5.2(4) . . . . ?
N5 C26 C25 C24 174.6(3) . . . . ?
N5 C26 C21 C20 1.1(4) . . . . ?
N5 C26 C21 C22 -177.5(4) . . . . ?
N5 C17 C19 C20 1.7(6) . . . . ?
N6 C10 C9 N8 153.7(5) . . . . ?
N6 C10 C9 N1 -166.1(6) . . . . ?
N6 C11 C16 C15 179.8(3) . . . . ?
N6 C11 C12 C13 -178.2(7) . . . . ?
N4 C25 C26 C21 175.3(3) . . . . ?
N4 C25 C24 C27 2.2(4) . . . . ?
N4 C25 C24 C23 -176.5(4) . . . . ?
N4 C29 C28 C27 3.7(6) . . . . ?
N7 C3 C8 N3 -0.5(3) . . . . ?
N7 C3 C8 C7 -179.4(3) . . . . ?
N7 C3 C4 C5 179.5(6) . . . . ?
N7 C2 N3 C8 -0.1(4) . . . . ?
N7 C2 C1 N8 -169.2(5) . . . . ?
N7 C2 C1 N1 150.2(5) . . . . ?
N3 C8 C3 C4 179.8(3) . . . . ?
N3 C8 C7 C6 -179.0(5) . . . . ?
N3 C2 C1 N8 8.3(4) . . . . ?
N3 C2 C1 N1 -32.2(5) . . . . ?
C3 C8 C7 C6 -0.3(5) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C8 C7 C6 C5 -0.1(6) . . . . ?
C16 C11 C12 C13 2.5(6) . . . . ?
C16 C15 C14 C13 1.0(6) . . . . ?
C26 C25 C24 C27 -177.6(4) . . . . ?
C26 C25 C24 C23 3.8(5) . . . . ?
C26 C21 C20 C19 -3.0(5) . . . . ?
C26 C21 C22 C23 2.2(5) . . . . ?
C10 C9 N8 C1 156.8(4) . . . . ?
C10 C9 N1 C1 -148.0(5) . . . . ?
C25 C24 C27 C28 -1.1(5) . . . . ?
C25 C24 C23 C22 0.4(5) . . . . ?
C24 C27 C28 C29 -1.8(5) . . . . ?
C24 C23 C22 C21 -3.4(6) . . . . ?
C11 C12 C13 C14 -2.5(7) . . . . ?
C7 C6 C5 C4 0.1(7) . . . . ?
C2 C1 N8 C9 -144.8(4) . . . . ?
C2 C1 N1 C9 160.3(4) . . . . ?
C20 C19 C17 C18 179.0(6) . . . . ?
C20 C21 C22 C23 -176.1(6) . . . . ?
C1 N8 C9 N1 56.9(8) . . . . ?
C1 N1 C9 N8 -56.0(7) . . . . ?
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
Cu1 N8 1 1
Cu1 N1 1 1
C1 N8 1 2
C1 N1 1 2
C9 N8 1 3
C9 N1 1 3
loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 2.0982 0.0112 0.0112
2 0.0200 1.4560 0.0134 0.0134
3 0.0200 1.4718 0.0221 0.0221
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
N8 0.0010
N1 0.0010
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.970(15)
2 0.030(15)
