#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:19:48 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289578 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/29/7062965.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_7062965
loop_
_publ_author_name
'Hajibabaei, Farshid'
'Salehzadeh, Sadegh'
'Derakhshandeh, Katayoun'
'Gable, Robert William'
_publ_section_title
;
 A new Cu(ii) complex derived from the reaction between
 tris(2-aminoethyl)amine and Cu(i)-activated acetonitrile with potent
 anticancer activity against some cell lines and high affinity for the
 essential proteins of SARS-CoV-2
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2251
_journal_page_last               2260
_journal_paper_doi               10.1039/D3NJ04142E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C13 H26 Cu N7 O2, H2 O, Cl'
_chemical_formula_sum            'C13 H28 Cl Cu N7 O3'
_chemical_formula_weight         429.41
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-30 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                107.679(6)
_cell_angle_beta                 103.872(5)
_cell_angle_gamma                106.779(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3648(4)
_cell_length_b                   11.0439(6)
_cell_length_c                   11.5384(8)
_cell_measurement_reflns_used    4070
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      29.6620
_cell_measurement_theta_min      3.4280
_cell_volume                     907.55(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  78.00   1.00   15.45    --   11.96  77.00 120.00   91
  2  ω    -76.00   9.00   1.00   15.45    --  -12.59 -57.00-150.00   85
  3  ω    -41.00  61.00   1.00   15.45    --  -12.59  57.00   0.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0144417000
_diffrn_orient_matrix_UB_12      -0.0167108000
_diffrn_orient_matrix_UB_13      0.0552923000
_diffrn_orient_matrix_UB_21      0.0804021000
_diffrn_orient_matrix_UB_22      -0.0058900000
_diffrn_orient_matrix_UB_23      -0.0053529000
_diffrn_orient_matrix_UB_31      0.0482793000
_diffrn_orient_matrix_UB_32      0.0710572000
_diffrn_orient_matrix_UB_33      0.0411402000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7277
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.837
_diffrn_reflns_theta_min         2.715
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.379
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       plate
_exptl_crystal_F_000             450
_exptl_crystal_recrystallization_method
'grown by slow evaporation from methanol/acetonitrile'
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0317
_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)+(0.0311P)²+0.8618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4030
_reflns_number_total             4481
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04142e2.cif
_cod_data_source_block           rwg2022apr_p166gau
_cod_depositor_comments          'Adding full bibliography for 7062965.cif.'
_cod_original_cell_volume        907.55(10)
_cod_database_code               7062965
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H28 Cl Cu N7 O3'
_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_max   0.949
_shelx_estimated_absorpt_t_min   0.655
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3C,H3D)
2.b Rotating group:
 N7(H7A,H7B)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6C,H6D)
2.d Aromatic/amide H refined with riding coordinates:
 N5(H5)
2.e X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
2.f Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.152
_oxdiff_exptl_absorpt_empirical_full_min 0.900
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 0.63512(3) 0.19522(2) 0.70842(2) 0.01357(8) Uani 1 1 d . . . . .
O1 O 0.69225(19) 0.13183(15) 0.55207(14) 0.0183(3) Uani 1 1 d . . . . .
O2 O 0.8657(2) 0.07728(16) 0.44443(15) 0.0219(3) Uani 1 1 d . . . . .
O3 O 0.7973(2) 0.2224(2) 0.2851(2) 0.0346(4) Uani 1 1 d G . . . .
H3C H 0.782555 0.180309 0.336758 0.052 Uiso 1 1 d G U . . .
H3D H 0.701965 0.240058 0.265186 0.052 Uiso 1 1 d G U . . .
N1 N 0.5612(2) 0.23291(16) 0.86583(16) 0.0139(3) Uani 1 1 d . . . . .
N2 N 0.7558(2) 0.09244(17) 0.78114(17) 0.0165(3) Uani 1 1 d . . . . .
N3 N 0.4429(2) 0.25446(17) 0.63556(16) 0.0159(3) Uani 1 1 d . . . . .
N4 N 0.8316(2) 0.41725(17) 0.81900(17) 0.0162(3) Uani 1 1 d . . . . .
N5 N 0.8876(2) 0.03713(18) 0.62658(17) 0.0182(3) Uani 1 1 d . . . . .
H5 H 0.964471 0.001573 0.608037 0.022 Uiso 1 1 calc R U . . .
N6 N 0.5010(3) 0.2650(2) 0.45405(19) 0.0257(4) Uani 1 1 d . . . . .
H6A H 0.575008 0.223297 0.464960 0.031 Uiso 1 1 calc R U . . .
H6B H 0.482472 0.289875 0.388031 0.031 Uiso 1 1 calc R U . . .
N7 N 0.9228(2) 0.62818(18) 0.79679(18) 0.0197(4) Uani 1 1 d . . . . .
H7A H 0.955247 0.655566 0.738349 0.024 Uiso 1 1 d R U . . .
H7B H 0.818064 0.632915 0.793815 0.024 Uiso 1 1 d R U . . .
C1 C 0.5714(3) 0.1215(2) 0.9114(2) 0.0186(4) Uani 1 1 d . . . . .
H1A H 0.464277 0.035500 0.855548 0.022 Uiso 1 1 calc R U . . .
H1B H 0.573361 0.148884 1.001935 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7381(3) 0.0959(2) 0.9059(2) 0.0191(4) Uani 1 1 d . . . . .
H2A H 0.844400 0.170500 0.979423 0.023 Uiso 1 1 calc R U . . .
H2B H 0.728705 0.007008 0.912462 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3738(3) 0.2214(2) 0.8189(2) 0.0182(4) Uani 1 1 d . . . . .
H3A H 0.343497 0.266182 0.894152 0.022 Uiso 1 1 calc R U . . .
H3B H 0.292049 0.122732 0.776103 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3465(3) 0.2887(2) 0.7233(2) 0.0189(4) Uani 1 1 d . . . . .
H4A H 0.217450 0.254715 0.672302 0.023 Uiso 1 1 calc R U . . .
H4B H 0.392412 0.390088 0.770920 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6866(3) 0.3712(2) 0.96849(19) 0.0169(4) Uani 1 1 d . . . . .
H5A H 0.789367 0.361351 1.022804 0.020 Uiso 1 1 calc R U . . .
H5B H 0.624624 0.406578 1.025584 0.020 Uiso 1 1 calc R U . . .
C6 C 0.7562(3) 0.4757(2) 0.9133(2) 0.0163(4) Uani 1 1 d . . . . .
H6C H 0.657283 0.497493 0.870144 0.020 Uiso 1 1 calc R U . . .
H6D H 0.849142 0.562163 0.984444 0.020 Uiso 1 1 calc R U . . .
C7 C 0.8598(3) 0.0386(2) 0.7398(2) 0.0176(4) Uani 1 1 d . . . . .
C8 C 0.9616(3) -0.0244(2) 0.8111(2) 0.0232(4) Uani 1 1 d . . . . .
H8A H 1.047115 0.046755 0.895964 0.035 Uiso 1 1 calc R U . . .
H8B H 1.026349 -0.063465 0.759978 0.035 Uiso 1 1 calc R U . . .
H8C H 0.878151 -0.097603 0.823927 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8102(3) 0.0846(2) 0.5363(2) 0.0180(4) Uani 1 1 d . . . . .
C10 C 0.9102(3) 0.4968(2) 0.7701(2) 0.0172(4) Uani 1 1 d . . . . .
C11 C 1.0049(3) 0.4474(2) 0.6828(2) 0.0231(4) Uani 1 1 d . . . . .
H11A H 1.008011 0.359272 0.682644 0.035 Uiso 1 1 calc R U . . .
H11B H 1.127495 0.515759 0.714552 0.035 Uiso 1 1 calc R U . . .
H11C H 0.941377 0.434616 0.593978 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4171(3) 0.2905(2) 0.5372(2) 0.0182(4) Uani 1 1 d . . . . .
C13 C 0.2948(3) 0.3632(2) 0.5115(2) 0.0241(4) Uani 1 1 d . . . . .
H13A H 0.172443 0.304201 0.495933 0.036 Uiso 1 1 calc R U . . .
H13B H 0.297926 0.382991 0.434654 0.036 Uiso 1 1 calc R U . . .
H13C H 0.334234 0.449959 0.587212 0.036 Uiso 1 1 calc R U . . .
Cl1 Cl 0.43569(7) 0.28864(5) 0.17807(5) 0.02253(12) 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'
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'
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0191
0 0 1 0.0191
1 -1 0 0.0968
-2 3 1 0.0938
-2 -1 3 0.0922
0 1 0 0.0983
1 1 0 0.1306
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
O1 Cu1 N1 172.05(6) . . ?
O1 Cu1 N2 89.69(6) . . ?
O1 Cu1 N3 98.00(6) . . ?
O1 Cu1 N4 103.89(6) . . ?
N1 Cu1 N4 83.44(6) . . ?
N2 Cu1 N1 85.54(7) . . ?
N2 Cu1 N3 161.17(7) . . ?
N2 Cu1 N4 103.75(7) . . ?
N3 Cu1 N1 84.75(7) . . ?
N3 Cu1 N4 91.11(7) . . ?
C9 O1 Cu1 129.08(14) . . ?
H3C O3 H3D 104.5 . . ?
C1 N1 Cu1 105.64(12) . . ?
C3 N1 Cu1 106.24(12) . . ?
C3 N1 C1 110.86(15) . . ?
C3 N1 C5 113.25(16) . . ?
C5 N1 Cu1 109.66(11) . . ?
C5 N1 C1 110.80(15) . . ?
C2 N2 Cu1 112.87(12) . . ?
C7 N2 Cu1 127.50(14) . . ?
C7 N2 C2 119.15(17) . . ?
C4 N3 Cu1 112.91(12) . . ?
C12 N3 Cu1 128.70(14) . . ?
C12 N3 C4 116.96(17) . . ?
C6 N4 Cu1 103.61(11) . . ?
C10 N4 Cu1 126.43(14) . . ?
C10 N4 C6 117.11(17) . . ?
C7 N5 H5 115.5 . . ?
C7 N5 C9 129.07(17) . . ?
C9 N5 H5 115.5 . . ?
H6A N6 H6B 120.0 . . ?
C12 N6 H6A 120.0 . . ?
C12 N6 H6B 120.0 . . ?
H7A N7 H7B 108.8 . . ?
C10 N7 H7A 109.6 . . ?
C10 N7 H7B 110.2 . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.26(16) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N2 C2 C1 108.22(17) . . ?
N2 C2 H2A 110.1 . . ?
N2 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
N1 C3 C4 111.49(16) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N3 C4 C3 108.73(16) . . ?
N3 C4 H4A 109.9 . . ?
N3 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
N1 C5 C6 113.06(16) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
N4 C6 C5 108.85(16) . . ?
N4 C6 H6C 109.9 . . ?
N4 C6 H6D 109.9 . . ?
C5 C6 H6C 109.9 . . ?
C5 C6 H6D 109.9 . . ?
H6C C6 H6D 108.3 . . ?
N2 C7 N5 121.92(18) . . ?
N2 C7 C8 123.23(19) . . ?
N5 C7 C8 114.83(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N5 119.84(18) . . ?
O2 C9 O1 124.09(19) . . ?
O2 C9 N5 116.07(18) . . ?
N4 C10 N7 124.85(19) . . ?
N4 C10 C11 119.52(18) . . ?
N7 C10 C11 115.53(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 N6 120.85(19) . . ?
N3 C12 C13 122.91(19) . . ?
N6 C12 C13 116.24(19) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 O1 1.9525(14) . ?
Cu1 N1 2.0205(16) . ?
Cu1 N2 1.9609(17) . ?
Cu1 N3 2.0033(17) . ?
Cu1 N4 2.2605(17) . ?
O1 C9 1.267(2) . ?
O2 C9 1.246(2) . ?
O3 H3C 0.8701 . ?
O3 H3D 0.8697 . ?
N1 C1 1.493(2) . ?
N1 C3 1.485(2) . ?
N1 C5 1.489(3) . ?
N2 C2 1.472(3) . ?
N2 C7 1.290(3) . ?
N3 C4 1.467(3) . ?
N3 C12 1.303(3) . ?
N4 C6 1.461(3) . ?
N4 C10 1.292(3) . ?
N5 H5 0.8800 . ?
N5 C7 1.377(3) . ?
N5 C9 1.408(3) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C12 1.328(3) . ?
N7 H7A 0.8856 . ?
N7 H7B 0.8855 . ?
N7 C10 1.354(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.515(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.521(3) . ?
C6 H6C 0.9900 . ?
C6 H6D 0.9900 . ?
C7 C8 1.496(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 C11 1.497(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.501(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
O3 H3C O2 0.87 2.06 2.844(2) 150.4 . yes
N6 H6A O1 0.88 1.93 2.740(2) 153.1 . yes
N6 H6B Cl1 0.88 2.35 3.2030(19) 161.9 . yes
N7 H7A O3 0.89 2.25 2.979(2) 139.7 2_766 yes
N7 H7B Cl1 0.89 2.57 3.4299(18) 165.4 2_666 yes
C3 H3B O2 0.99 2.53 3.362(3) 141.8 2_656 yes
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 O1 C9 O2 -162.26(15) . . . . ?
Cu1 O1 C9 N5 17.3(3) . . . . ?
Cu1 N1 C1 C2 42.01(19) . . . . ?
Cu1 N1 C3 C4 -41.71(19) . . . . ?
Cu1 N1 C5 C6 33.92(19) . . . . ?
Cu1 N2 C2 C1 24.6(2) . . . . ?
Cu1 N2 C7 N5 -5.9(3) . . . . ?
Cu1 N2 C7 C8 172.93(15) . . . . ?
Cu1 N3 C4 C3 -20.2(2) . . . . ?
Cu1 N3 C12 N6 13.9(3) . . . . ?
Cu1 N3 C12 C13 -165.52(15) . . . . ?
Cu1 N4 C6 C5 41.31(17) . . . . ?
Cu1 N4 C10 N7 132.88(18) . . . . ?
Cu1 N4 C10 C11 -50.8(3) . . . . ?
O1 Cu1 N2 C2 -174.91(14) . . . . ?
O1 Cu1 N2 C7 13.17(18) . . . . ?
O1 Cu1 N3 C4 170.64(13) . . . . ?
O1 Cu1 N3 C12 -23.65(19) . . . . ?
O1 Cu1 N4 C6 163.67(11) . . . . ?
O1 Cu1 N4 C10 24.08(18) . . . . ?
N1 Cu1 N2 C2 -1.26(14) . . . . ?
N1 Cu1 N2 C7 -173.19(18) . . . . ?
N1 Cu1 N3 C4 -1.85(13) . . . . ?
N1 Cu1 N3 C12 163.86(19) . . . . ?
N1 Cu1 N4 C6 -19.44(12) . . . . ?
N1 Cu1 N4 C10 -159.03(17) . . . . ?
N1 C1 C2 N2 -44.3(2) . . . . ?
N1 C3 C4 N3 41.3(2) . . . . ?
N1 C5 C6 N4 -53.0(2) . . . . ?
N2 Cu1 O1 C9 -19.44(17) . . . . ?
N2 Cu1 N1 C1 -22.39(13) . . . . ?
N2 Cu1 N1 C3 -140.21(13) . . . . ?
N2 Cu1 N1 C5 97.05(13) . . . . ?
N2 Cu1 N3 C4 57.4(3) . . . . ?
N2 Cu1 N3 C12 -136.9(2) . . . . ?
N2 Cu1 N4 C6 -103.19(12) . . . . ?
N2 Cu1 N4 C10 117.21(17) . . . . ?
N3 Cu1 O1 C9 177.81(17) . . . . ?
N3 Cu1 N1 C1 141.46(13) . . . . ?
N3 Cu1 N1 C3 23.63(12) . . . . ?
N3 Cu1 N1 C5 -99.10(13) . . . . ?
N3 Cu1 N2 C2 -60.4(3) . . . . ?
N3 Cu1 N2 C7 127.7(2) . . . . ?
N3 Cu1 N4 C6 65.15(12) . . . . ?
N3 Cu1 N4 C10 -74.45(17) . . . . ?
N4 Cu1 O1 C9 84.66(17) . . . . ?
N4 Cu1 N1 C1 -126.81(13) . . . . ?
N4 Cu1 N1 C3 115.37(12) . . . . ?
N4 Cu1 N1 C5 -7.37(12) . . . . ?
N4 Cu1 N2 C2 80.86(14) . . . . ?
N4 Cu1 N2 C7 -91.06(18) . . . . ?
N4 Cu1 N3 C4 -85.16(14) . . . . ?
N4 Cu1 N3 C12 80.55(18) . . . . ?
C1 N1 C3 C4 -156.01(17) . . . . ?
C1 N1 C5 C6 150.15(16) . . . . ?
C2 N2 C7 N5 -177.36(18) . . . . ?
C2 N2 C7 C8 1.5(3) . . . . ?
C3 N1 C1 C2 156.69(17) . . . . ?
C3 N1 C5 C6 -84.6(2) . . . . ?
C4 N3 C12 N6 179.13(19) . . . . ?
C4 N3 C12 C13 -0.3(3) . . . . ?
C5 N1 C1 C2 -76.7(2) . . . . ?
C5 N1 C3 C4 78.7(2) . . . . ?
C6 N4 C10 N7 -2.1(3) . . . . ?
C6 N4 C10 C11 174.28(18) . . . . ?
C7 N2 C2 C1 -162.71(18) . . . . ?
C7 N5 C9 O1 -3.1(3) . . . . ?
C7 N5 C9 O2 176.55(19) . . . . ?
C9 N5 C7 N2 -2.7(3) . . . . ?
C9 N5 C7 C8 178.41(19) . . . . ?
C10 N4 C6 C5 -174.56(17) . . . . ?
C12 N3 C4 C3 172.24(18) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 0.0000 -1.0000 -0.0553 0.0054 -0.0411
-0.0000 -0.0000 1.0000 0.0553 -0.0054 0.0411
1.0000 -1.0000 -0.0000 0.0312 0.0863 -0.0228
-2.0000 3.0000 1.0000 -0.0237 -0.1838 0.1578
-2.0000 -1.0000 3.0000 0.1537 -0.1710 -0.0442
-0.0000 1.0000 0.0000 -0.0167 -0.0059 0.0711
1.0000 1.0000 0.0000 -0.0023 0.0745 0.1193
