# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014
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#
# Cambridge Crystallographic Data Centre
# CCDC
#
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#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
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# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
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data_1
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C20 H20 Cl Cu N5 O6'
_chemical_formula_weight 525.40
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'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P2(1)/n '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 12.467(9)
_cell_length_b 11.156(8)
_cell_length_c 16.139(12)
_cell_angle_alpha 90.00
_cell_angle_beta 96.304(9)
_cell_angle_gamma 90.00
_cell_volume 2231(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description block
_exptl_crystal_colour blue-green
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.24
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.564
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1076
_exptl_absorpt_coefficient_mu 1.146
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.716
_exptl_absorpt_correction_T_max 0.760
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX II area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 15418
_diffrn_reflns_av_R_equivalents 0.0545
_diffrn_reflns_av_sigmaI/netI 0.0513
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.54
_diffrn_reflns_theta_max 25.50
_reflns_number_total 4120
_reflns_number_gt 3297
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART APEX II'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT '
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0930P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4120
_refine_ls_number_parameters 303
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0571
_refine_ls_R_factor_gt 0.0457
_refine_ls_wR_factor_ref 0.1376
_refine_ls_wR_factor_gt 0.1286
_refine_ls_goodness_of_fit_ref 1.037
_refine_ls_restrained_S_all 1.037
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
Cu Cu 0.59075(3) 0.60765(3) 0.11441(2) 0.02750(16) Uani 1 1 d . . .
Cl Cl 0.37204(7) 0.76243(7) 0.31295(5) 0.0383(2) Uani 1 1 d . . .
O1 O 0.63238(16) 0.69142(17) 0.01641(12) 0.0292(5) Uani 1 1 d . . .
O2 O 0.60300(18) 0.8366(2) 0.10379(12) 0.0356(5) Uani 1 1 d . . .
N5 N 0.4393(2) 0.5797(2) 0.07329(15) 0.0298(6) Uani 1 1 d . . .
N1 N 0.5432(2) 0.5282(3) 0.21984(17) 0.0382(6) Uani 1 1 d . . .
N3 N 0.7344(2) 0.5918(2) 0.17672(15) 0.0316(6) Uani 1 1 d . . .
C18 C 0.6694(3) 0.8873(3) -0.02620(18) 0.0309(7) Uani 1 1 d . . .
H18 H 0.6989 0.8556 -0.0719 0.037 Uiso 1 1 calc R . .
N4 N 0.2809(2) 0.5060(2) 0.09660(16) 0.0367(6) Uani 1 1 d . . .
H4 H 0.2332 0.4676 0.1208 0.044 Uiso 1 1 calc R . .
C2 C 0.7363(3) 0.5214(3) 0.24412(18) 0.0345(7) Uani 1 1 d . . .
C17 C 0.6328(2) 0.8026(3) 0.03589(17) 0.0264(6) Uani 1 1 d . . .
C16 C 0.3637(3) 0.6173(3) 0.0088(2) 0.0306(7) Uani 1 1 d . . .
C10 C 0.3852(3) 0.5133(3) 0.12363(19) 0.0339(7) Uani 1 1 d . . .
C12 C 0.1686(3) 0.5962(3) -0.0309(2) 0.0426(9) Uani 1 1 d . . .
H12 H 0.1016 0.5652 -0.0217 0.051 Uiso 1 1 calc R . .
O6 O 0.4595(2) 0.7689(2) 0.26252(16) 0.0496(6) Uani 1 1 d . . .
C8 C 0.8409(3) 0.6242(3) 0.17038(19) 0.0312(7) Uani 1 1 d . . .
N2 N 0.8358(2) 0.5051(2) 0.28137(15) 0.0395(7) Uani 1 1 d . . .
H2 H 0.8533 0.4624 0.3252 0.047 Uiso 1 1 calc R . .
C15 C 0.3737(3) 0.6903(3) -0.05943(19) 0.0332(7) Uani 1 1 d . . .
H15 H 0.4400 0.7222 -0.0692 0.040 Uiso 1 1 calc R . .
C19 C 0.6625(3) 1.0048(3) -0.02041(19) 0.0354(7) Uani 1 1 d . . .
H19 H 0.6320 1.0354 0.0253 0.043 Uiso 1 1 calc R . .
C4 C 1.0175(3) 0.5847(3) 0.2476(2) 0.0461(9) Uani 1 1 d . . .
H4A H 1.0599 0.5491 0.2919 0.055 Uiso 1 1 calc R . .
C3 C 0.9068(3) 0.5693(3) 0.23687(19) 0.0362(7) Uani 1 1 d . . .
C7 C 0.8873(3) 0.6927(3) 0.1118(2) 0.0344(7) Uani 1 1 d . . .
H7 H 0.8456 0.7273 0.0668 0.041 Uiso 1 1 calc R . .
C6 C 0.9994(3) 0.7074(3) 0.1234(2) 0.0428(8) Uani 1 1 d . . .
H6 H 1.0325 0.7536 0.0855 0.051 Uiso 1 1 calc R . .
C9 C 0.4430(3) 0.4568(3) 0.1994(2) 0.0375(8) Uani 1 1 d . . .
H9A H 0.3988 0.4589 0.2452 0.045 Uiso 1 1 calc R . .
H9B H 0.4605 0.3740 0.1884 0.045 Uiso 1 1 calc R . .
C13 C 0.1801(3) 0.6682(3) -0.0971(2) 0.0458(9) Uani 1 1 d . . .
H13 H 0.1195 0.6880 -0.1333 0.055 Uiso 1 1 calc R . .
C11 C 0.2614(3) 0.5703(3) 0.0229(2) 0.0347(7) Uani 1 1 d . . .
O3 O 0.4038(2) 0.8048(4) 0.39465(17) 0.0791(11) Uani 1 1 d . . .
C14 C 0.2816(3) 0.7138(3) -0.1122(2) 0.0400(8) Uani 1 1 d . . .
H14 H 0.2866 0.7610 -0.1592 0.048 Uiso 1 1 calc R . .
O5 O 0.3344(4) 0.6416(3) 0.3140(3) 0.1058(15) Uani 1 1 d . . .
C20 C 0.6991(3) 1.0930(3) -0.0806(2) 0.0469(9) Uani 1 1 d . . .
H20A H 0.7337 1.0514 -0.1224 0.070 Uiso 1 1 calc R . .
H20B H 0.7493 1.1479 -0.0515 0.070 Uiso 1 1 calc R . .
H20C H 0.6380 1.1365 -0.1065 0.070 Uiso 1 1 calc R . .
C5 C 1.0628(3) 0.6546(3) 0.1903(2) 0.0468(9) Uani 1 1 d . . .
H5 H 1.1370 0.6669 0.1963 0.056 Uiso 1 1 calc R . .
C1 C 0.6342(3) 0.4685(3) 0.2693(2) 0.0422(8) Uani 1 1 d . . .
H1A H 0.6322 0.3829 0.2586 0.051 Uiso 1 1 calc R . .
H1B H 0.6301 0.4813 0.3283 0.051 Uiso 1 1 calc R . .
O4 O 0.2850(2) 0.8360(3) 0.27722(18) 0.0727(9) Uani 1 1 d . . .
H1 H 0.528(3) 0.597(4) 0.254(2) 0.054(12) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu 0.0316(3) 0.0268(2) 0.0254(2) 0.00329(14) 0.00932(16) -0.00028(14)
Cl 0.0391(5) 0.0398(5) 0.0384(4) -0.0031(3) 0.0150(3) 0.0050(3)
O1 0.0362(12) 0.0256(11) 0.0273(10) 0.0014(8) 0.0093(9) -0.0017(9)
O2 0.0497(14) 0.0327(12) 0.0268(11) -0.0017(9) 0.0143(10) -0.0047(10)
N5 0.0326(14) 0.0292(13) 0.0298(13) -0.0013(10) 0.0134(11) -0.0014(11)
N1 0.0494(17) 0.0333(15) 0.0345(14) 0.0040(12) 0.0162(12) 0.0016(13)
N3 0.0366(15) 0.0352(14) 0.0237(12) 0.0043(10) 0.0068(11) 0.0039(11)
C18 0.0367(17) 0.0327(17) 0.0248(15) 0.0029(12) 0.0102(13) 0.0002(13)
N4 0.0355(15) 0.0329(14) 0.0464(16) -0.0037(12) 0.0261(12) -0.0086(12)
C2 0.049(2) 0.0293(16) 0.0258(15) 0.0024(12) 0.0083(14) 0.0057(14)
C17 0.0239(15) 0.0304(16) 0.0256(14) 0.0012(12) 0.0061(11) -0.0012(12)
C16 0.0297(17) 0.0282(16) 0.0356(16) -0.0058(12) 0.0117(13) -0.0004(12)
C10 0.0432(19) 0.0260(15) 0.0366(17) -0.0044(13) 0.0222(14) -0.0048(14)
C12 0.0282(18) 0.0401(19) 0.061(2) -0.0136(16) 0.0117(16) -0.0035(14)
O6 0.0476(15) 0.0584(16) 0.0473(15) -0.0047(12) 0.0252(12) 0.0037(12)
C8 0.0374(18) 0.0279(16) 0.0286(15) -0.0041(12) 0.0041(13) 0.0050(13)
N2 0.0549(18) 0.0394(15) 0.0236(13) 0.0062(11) 0.0023(12) 0.0104(13)
C15 0.0319(17) 0.0335(17) 0.0354(16) -0.0010(13) 0.0087(13) -0.0019(13)
C19 0.0463(19) 0.0330(17) 0.0281(15) 0.0004(13) 0.0086(14) -0.0019(14)
C4 0.046(2) 0.048(2) 0.0410(19) -0.0108(16) -0.0096(17) 0.0152(17)
C3 0.044(2) 0.0340(17) 0.0295(15) -0.0044(13) 0.0014(14) 0.0073(15)
C7 0.0336(17) 0.0338(17) 0.0364(17) 0.0026(13) 0.0068(13) 0.0032(14)
C6 0.0390(19) 0.0394(19) 0.052(2) -0.0054(16) 0.0132(16) 0.0027(15)
C9 0.049(2) 0.0284(17) 0.0387(17) 0.0039(13) 0.0206(15) -0.0023(15)
C13 0.040(2) 0.041(2) 0.055(2) -0.0100(17) -0.0013(17) 0.0039(16)
C11 0.0305(17) 0.0267(15) 0.0494(19) -0.0090(14) 0.0149(14) -0.0045(13)
O3 0.063(2) 0.135(3) 0.0405(16) -0.0239(17) 0.0087(14) 0.0132(19)
C14 0.044(2) 0.0376(18) 0.0391(18) -0.0005(14) 0.0069(15) 0.0024(15)
O5 0.151(4) 0.0444(17) 0.140(4) -0.009(2) 0.100(3) -0.014(2)
C20 0.070(3) 0.0333(18) 0.0402(19) 0.0035(15) 0.0174(18) -0.0058(17)
C5 0.0338(19) 0.046(2) 0.061(2) -0.0154(18) 0.0042(17) 0.0045(16)
C1 0.057(2) 0.0409(19) 0.0311(16) 0.0102(14) 0.0153(15) 0.0073(17)
O4 0.0588(18) 0.103(2) 0.0579(18) -0.0014(17) 0.0119(15) 0.0354(18)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu O1 1.956(2) . ?
Cu N5 1.957(3) . ?
Cu N3 1.963(3) . ?
Cu N1 2.063(3) . ?
Cu O2 2.566(3) . ?
Cl O3 1.416(3) . ?
Cl O5 1.428(3) 1 ?
Cl O5 1.428(3) . ?
Cl O4 1.431(3) . ?
Cl O6 1.433(3) 1 ?
Cl O6 1.433(3) . ?
O1 C17 1.279(4) . ?
O2 C17 1.254(4) . ?
N5 C10 1.335(4) . ?
N5 C16 1.390(4) . ?
N1 C1 1.473(4) . ?
N1 C9 1.487(4) . ?
N3 C2 1.340(4) . ?
N3 C8 1.390(4) . ?
C18 C19 1.318(4) . ?
C18 C17 1.485(4) . ?
N4 C10 1.327(4) . ?
N4 C11 1.387(4) . ?
C2 N2 1.330(4) . ?
C2 C1 1.499(5) . ?
C16 C15 1.386(4) . ?
C16 C11 1.420(5) . ?
C10 C9 1.490(5) . ?
C12 C13 1.357(6) . ?
C12 C11 1.399(5) . ?
O6 O6 0.000(5) 1 ?
C8 C7 1.391(5) . ?
C8 C3 1.417(4) . ?
N2 C3 1.398(5) . ?
C15 C14 1.377(4) . ?
C19 C20 1.489(5) . ?
C4 C5 1.377(6) . ?
C4 C3 1.382(5) . ?
C7 C6 1.398(5) . ?
C6 C5 1.397(5) . ?
C13 C14 1.410(5) . ?
O5 O5 0.000(11) 1 ?
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 Cu N5 97.69(10) . . ?
O1 Cu N3 98.57(10) . . ?
N5 Cu N3 162.09(11) . . ?
O1 Cu N1 176.79(10) . . ?
N5 Cu N1 81.78(11) . . ?
N3 Cu N1 82.39(12) . . ?
O1 Cu O2 56.44(8) . . ?
N5 Cu O2 101.44(9) . . ?
N3 Cu O2 93.79(9) . . ?
N1 Cu O2 120.51(9) . . ?
O3 Cl O5 111.3(3) . 1 ?
O3 Cl O5 111.3(3) . . ?
O5 Cl O5 0.0(4) 1 . ?
O3 Cl O4 107.8(2) . . ?
O5 Cl O4 108.1(3) 1 . ?
O5 Cl O4 108.1(3) . . ?
O3 Cl O6 111.10(18) . 1 ?
O5 Cl O6 109.03(19) 1 1 ?
O5 Cl O6 109.03(19) . 1 ?
O4 Cl O6 109.46(18) . 1 ?
O3 Cl O6 111.10(18) . . ?
O5 Cl O6 109.03(19) 1 . ?
O5 Cl O6 109.03(19) . . ?
O4 Cl O6 109.46(18) . . ?
O6 Cl O6 0.00(15) 1 . ?
C17 O1 Cu 105.00(18) . . ?
C17 O2 Cu 77.42(17) . . ?
C10 N5 C16 106.1(3) . . ?
C10 N5 Cu 114.5(2) . . ?
C16 N5 Cu 139.1(2) . . ?
C1 N1 C9 117.2(3) . . ?
C1 N1 Cu 111.5(2) . . ?
C9 N1 Cu 110.95(19) . . ?
C2 N3 C8 106.3(3) . . ?
C2 N3 Cu 113.7(2) . . ?
C8 N3 Cu 139.8(2) . . ?
C19 C18 C17 123.9(3) . . ?
C10 N4 C11 108.8(3) . . ?
N2 C2 N3 112.3(3) . . ?
N2 C2 C1 126.9(3) . . ?
N3 C2 C1 120.7(3) . . ?
O2 C17 O1 121.0(3) . . ?
O2 C17 C18 122.6(3) . . ?
O1 C17 C18 116.4(3) . . ?
C15 C16 N5 131.3(3) . . ?
C15 C16 C11 120.3(3) . . ?
N5 C16 C11 108.3(3) . . ?
N4 C10 N5 112.1(3) . . ?
N4 C10 C9 127.7(3) . . ?
N5 C10 C9 120.2(3) . . ?
C13 C12 C11 117.3(3) . . ?
O6 O6 Cl 0(10) 1 . ?
N3 C8 C7 131.7(3) . . ?
N3 C8 C3 108.2(3) . . ?
C7 C8 C3 120.1(3) . . ?
C2 N2 C3 108.0(3) . . ?
C14 C15 C16 117.5(3) . . ?
C18 C19 C20 125.7(3) . . ?
C5 C4 C3 117.6(3) . . ?
C4 C3 N2 132.8(3) . . ?
C4 C3 C8 122.0(3) . . ?
N2 C3 C8 105.2(3) . . ?
C8 C7 C6 117.3(3) . . ?
C5 C6 C7 121.7(3) . . ?
N1 C9 C10 105.9(2) . . ?
C12 C13 C14 121.7(3) . . ?
N4 C11 C12 133.9(3) . . ?
N4 C11 C16 104.7(3) . . ?
C12 C11 C16 121.4(3) . . ?
C15 C14 C13 121.8(3) . . ?
O5 O5 Cl 0(10) 1 . ?
C4 C5 C6 121.3(3) . . ?
N1 C1 C2 107.6(3) . . ?
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
N5 Cu O1 C17 100.92(18) . . . . ?
N3 Cu O1 C17 -86.61(18) . . . . ?
N1 Cu O1 C17 20.7(18) . . . . ?
O2 Cu O1 C17 2.25(16) . . . . ?
O1 Cu O2 C17 -2.27(16) . . . . ?
N5 Cu O2 C17 -93.97(18) . . . . ?
N3 Cu O2 C17 95.50(18) . . . . ?
N1 Cu O2 C17 178.90(17) . . . . ?
O1 Cu N5 C10 174.9(2) . . . . ?
N3 Cu N5 C10 19.8(5) . . . . ?
N1 Cu N5 C10 -8.3(2) . . . . ?
O2 Cu N5 C10 -127.9(2) . . . . ?
O1 Cu N5 C16 -13.0(3) . . . . ?
N3 Cu N5 C16 -168.0(3) . . . . ?
N1 Cu N5 C16 163.8(3) . . . . ?
O2 Cu N5 C16 44.2(3) . . . . ?
O1 Cu N1 C1 -126.1(17) . . . . ?
N5 Cu N1 C1 153.2(2) . . . . ?
N3 Cu N1 C1 -18.4(2) . . . . ?
O2 Cu N1 C1 -108.3(2) . . . . ?
O1 Cu N1 C9 101.3(18) . . . . ?
N5 Cu N1 C9 20.6(2) . . . . ?
N3 Cu N1 C9 -151.0(2) . . . . ?
O2 Cu N1 C9 119.1(2) . . . . ?
O1 Cu N3 C2 -171.0(2) . . . . ?
N5 Cu N3 C2 -16.0(5) . . . . ?
N1 Cu N3 C2 12.0(2) . . . . ?
O2 Cu N3 C2 132.3(2) . . . . ?
O1 Cu N3 C8 2.6(3) . . . . ?
N5 Cu N3 C8 157.6(3) . . . . ?
N1 Cu N3 C8 -174.4(3) . . . . ?
O2 Cu N3 C8 -54.1(3) . . . . ?
C8 N3 C2 N2 -0.5(4) . . . . ?
Cu N3 C2 N2 175.2(2) . . . . ?
C8 N3 C2 C1 -179.2(3) . . . . ?
Cu N3 C2 C1 -3.5(4) . . . . ?
Cu O2 C17 O1 3.4(2) . . . . ?
Cu O2 C17 C18 -177.1(3) . . . . ?
Cu O1 C17 O2 -4.5(3) . . . . ?
Cu O1 C17 C18 176.0(2) . . . . ?
C19 C18 C17 O2 -8.0(5) . . . . ?
C19 C18 C17 O1 171.5(3) . . . . ?
C10 N5 C16 C15 178.1(3) . . . . ?
Cu N5 C16 C15 5.6(5) . . . . ?
C10 N5 C16 C11 0.0(3) . . . . ?
Cu N5 C16 C11 -172.5(2) . . . . ?
C11 N4 C10 N5 0.4(4) . . . . ?
C11 N4 C10 C9 -178.9(3) . . . . ?
C16 N5 C10 N4 -0.2(3) . . . . ?
Cu N5 C10 N4 174.4(2) . . . . ?
C16 N5 C10 C9 179.1(3) . . . . ?
Cu N5 C10 C9 -6.3(4) . . . . ?
O3 Cl O6 O6 0.0(2) . . . 1 ?
O5 Cl O6 O6 0.00(15) 1 . . 1 ?
O5 Cl O6 O6 0.00(15) . . . 1 ?
O4 Cl O6 O6 0.00(17) . . . 1 ?
C2 N3 C8 C7 177.9(3) . . . . ?
Cu N3 C8 C7 4.0(6) . . . . ?
C2 N3 C8 C3 0.3(3) . . . . ?
Cu N3 C8 C3 -173.6(2) . . . . ?
N3 C2 N2 C3 0.5(4) . . . . ?
C1 C2 N2 C3 179.1(3) . . . . ?
N5 C16 C15 C14 -178.4(3) . . . . ?
C11 C16 C15 C14 -0.5(5) . . . . ?
C17 C18 C19 C20 179.3(3) . . . . ?
C5 C4 C3 N2 179.3(3) . . . . ?
C5 C4 C3 C8 -0.8(5) . . . . ?
C2 N2 C3 C4 179.6(4) . . . . ?
C2 N2 C3 C8 -0.2(3) . . . . ?
N3 C8 C3 C4 -179.9(3) . . . . ?
C7 C8 C3 C4 2.2(5) . . . . ?
N3 C8 C3 N2 -0.1(3) . . . . ?
C7 C8 C3 N2 -178.0(3) . . . . ?
N3 C8 C7 C6 -179.4(3) . . . . ?
C3 C8 C7 C6 -2.1(4) . . . . ?
C8 C7 C6 C5 0.8(5) . . . . ?
C1 N1 C9 C10 -156.7(3) . . . . ?
Cu N1 C9 C10 -27.0(3) . . . . ?
N4 C10 C9 N1 -158.2(3) . . . . ?
N5 C10 C9 N1 22.6(4) . . . . ?
C11 C12 C13 C14 1.1(5) . . . . ?
C10 N4 C11 C12 -177.9(3) . . . . ?
C10 N4 C11 C16 -0.3(3) . . . . ?
C13 C12 C11 N4 177.2(3) . . . . ?
C13 C12 C11 C16 -0.1(5) . . . . ?
C15 C16 C11 N4 -178.1(3) . . . . ?
N5 C16 C11 N4 0.2(3) . . . . ?
C15 C16 C11 C12 -0.2(5) . . . . ?
N5 C16 C11 C12 178.2(3) . . . . ?
C16 C15 C14 C13 1.5(5) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
O3 Cl O5 O5 0.00(14) . . . 1 ?
O4 Cl O5 O5 0.00(10) . . . 1 ?
O6 Cl O5 O5 0.0(2) 1 . . 1 ?
O6 Cl O5 O5 0.0(2) . . . 1 ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C7 C6 C5 C4 0.5(5) . . . . ?
C9 N1 C1 C2 149.4(3) . . . . ?
Cu N1 C1 C2 20.0(3) . . . . ?
N2 C2 C1 N1 169.9(3) . . . . ?
N3 C2 C1 N1 -11.5(4) . . . . ?
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
C9 H9A O5 0.97 2.50 3.171(5) 126.6 1
N1 H1 O6 0.98(4) 2.11(4) 2.989(4) 149(3) 1
N4 H4 O3 0.86 2.49 3.229(5) 145.0 2_545
N4 H4 O4 0.86 2.24 2.964(4) 142.4 2_545
N2 H2 O2 0.86 1.86 2.690(4) 163.1 2_645
C13 H13 O6 0.93 2.51 3.438(5) 176.3 4_575
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 25.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.768
_refine_diff_density_min -0.671
_refine_diff_density_rms 0.093
_database_code_depnum_ccdc_archive 'CCDC 783372'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_1
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C20 H20 Cl Cu N5 O6'
_chemical_formula_weight 525.40
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'
O O 0.0106 0.0060 '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'
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'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P21/c '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.772(2)
_cell_length_b 14.952(4)
_cell_length_c 13.660(3)
_cell_angle_alpha 90.00
_cell_angle_beta 116.415(10)
_cell_angle_gamma 90.00
_cell_volume 2153.3(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description block
_exptl_crystal_colour blue-green
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.28
_exptl_crystal_size_min 0.24
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.621
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1076
_exptl_absorpt_coefficient_mu 1.188
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.691
_exptl_absorpt_correction_T_max 0.752
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX II area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17753
_diffrn_reflns_av_R_equivalents 0.0393
_diffrn_reflns_av_sigmaI/netI 0.0361
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 1.93
_diffrn_reflns_theta_max 27.56
_reflns_number_total 4958
_reflns_number_gt 4058
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART APEX II'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+1.8516P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4958
_refine_ls_number_parameters 303
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0512
_refine_ls_R_factor_gt 0.0377
_refine_ls_wR_factor_ref 0.1016
_refine_ls_wR_factor_gt 0.0949
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_restrained_S_all 1.040
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
C1 C -0.1572(2) 0.71590(18) 0.0593(2) 0.0326(6) Uani 1 1 d . . .
H1A H -0.2140 0.7479 0.0809 0.039 Uiso 1 1 calc R . .
H1B H -0.1800 0.7296 -0.0166 0.039 Uiso 1 1 calc R . .
C2 C -0.0229(2) 0.74172(18) 0.13021(18) 0.0282(5) Uani 1 1 d . . .
C3 C 0.1519(2) 0.81871(18) 0.22150(19) 0.0298(5) Uani 1 1 d . . .
C4 C 0.2437(3) 0.88413(19) 0.2675(2) 0.0372(6) Uani 1 1 d . . .
H4 H 0.2232 0.9446 0.2599 0.045 Uiso 1 1 calc R . .
C5 C 0.3672(3) 0.8549(2) 0.3251(2) 0.0427(7) Uani 1 1 d . . .
H5 H 0.4318 0.8967 0.3574 0.051 Uiso 1 1 calc R . .
C6 C 0.3976(2) 0.7634(2) 0.3359(2) 0.0385(6) Uani 1 1 d . . .
H6 H 0.4818 0.7462 0.3758 0.046 Uiso 1 1 calc R . .
C7 C 0.3059(2) 0.69841(18) 0.28912(19) 0.0300(5) Uani 1 1 d . . .
H7 H 0.3267 0.6380 0.2960 0.036 Uiso 1 1 calc R . .
C8 C 0.1803(2) 0.72709(17) 0.23089(18) 0.0272(5) Uani 1 1 d . . .
C9 C -0.2585(2) 0.56943(19) -0.0230(2) 0.0367(6) Uani 1 1 d . . .
H9A H -0.3435 0.5763 -0.0295 0.044 Uiso 1 1 calc R . .
H9B H -0.2575 0.5913 -0.0895 0.044 Uiso 1 1 calc R . .
C10 C -0.2186(2) 0.47366(19) -0.00425(18) 0.0304(5) Uani 1 1 d . . .
C11 C -0.2159(2) 0.32657(19) -0.00529(19) 0.0316(5) Uani 1 1 d . . .
C12 C -0.2435(3) 0.2359(2) -0.0212(2) 0.0379(6) Uani 1 1 d . . .
H12 H -0.3249 0.2154 -0.0659 0.045 Uiso 1 1 calc R . .
C13 C -0.1440(3) 0.1780(2) 0.0327(2) 0.0392(6) Uani 1 1 d . . .
H13 H -0.1588 0.1167 0.0243 0.047 Uiso 1 1 calc R . .
C14 C -0.0206(3) 0.2088(2) 0.0999(2) 0.0365(6) Uani 1 1 d . . .
H14 H 0.0442 0.1675 0.1343 0.044 Uiso 1 1 calc R . .
C15 C 0.0063(2) 0.29895(18) 0.11611(19) 0.0299(5) Uani 1 1 d . . .
H15 H 0.0877 0.3192 0.1613 0.036 Uiso 1 1 calc R . .
C16 C -0.0937(2) 0.35861(18) 0.06185(18) 0.0286(5) Uani 1 1 d . . .
C17 C 0.1806(2) 0.47620(17) 0.30311(19) 0.0284(5) Uani 1 1 d . . .
C18 C 0.3061(3) 0.44039(17) 0.3868(2) 0.0376(6) Uani 1 1 d . . .
C19 C 0.3214(3) 0.4286(2) 0.4882(2) 0.0540(9) Uani 1 1 d . . .
H19A H 0.3987 0.4085 0.5421 0.065 Uiso 1 1 calc R . .
H19B H 0.2549 0.4406 0.5054 0.065 Uiso 1 1 calc R . .
C20 C 0.4068(3) 0.4232(2) 0.3507(3) 0.0495(8) Uani 1 1 d . . .
H20A H 0.4843 0.4072 0.4128 0.074 Uiso 1 1 calc R . .
H20B H 0.4200 0.4762 0.3175 0.074 Uiso 1 1 calc R . .
H20C H 0.3806 0.3752 0.2987 0.074 Uiso 1 1 calc R . .
Cl Cl 0.36590(5) 0.15208(4) 0.28107(4) 0.02903(14) Uani 1 1 d . . .
Cu Cu 0.00761(2) 0.55684(2) 0.13555(2) 0.02625(10) Uani 1 1 d . . .
N1 N -0.1650(2) 0.61947(16) 0.07403(19) 0.0373(5) Uani 1 1 d . . .
N2 N 0.02203(19) 0.82509(15) 0.15763(16) 0.0308(5) Uani 1 1 d . . .
H2D H -0.0217 0.8736 0.1390 0.037 Uiso 1 1 calc R . .
N3 N 0.06798(18) 0.68030(14) 0.17160(15) 0.0264(4) Uani 1 1 d . . .
N4 N -0.29087(19) 0.40205(16) -0.04569(16) 0.0328(5) Uani 1 1 d . . .
H4D H -0.3705 0.4024 -0.0900 0.039 Uiso 1 1 calc R . .
N5 N -0.09811(18) 0.45252(15) 0.06100(15) 0.0290(5) Uani 1 1 d . . .
O1 O 0.08797(17) 0.48448(13) 0.32408(14) 0.0344(4) Uani 1 1 d . . .
O2 O 0.17379(15) 0.49864(12) 0.21008(13) 0.0293(4) Uani 1 1 d . . .
O3 O 0.4161(2) 0.19021(15) 0.38849(15) 0.0461(5) Uani 1 1 d . . .
O6 O 0.45856(17) 0.09243(15) 0.27436(16) 0.0450(5) Uani 1 1 d . . .
O5 O 0.25270(18) 0.10215(14) 0.26019(17) 0.0441(5) Uani 1 1 d . . .
O4 O 0.3346(2) 0.22087(15) 0.20048(16) 0.0484(5) Uani 1 1 d . . .
H1 H -0.193(4) 0.609(3) 0.141(3) 0.085(13) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0227(12) 0.0389(15) 0.0326(12) 0.0063(11) 0.0091(10) 0.0093(11)
C2 0.0244(11) 0.0380(14) 0.0237(10) 0.0048(10) 0.0120(9) 0.0079(10)
C3 0.0293(12) 0.0342(14) 0.0265(11) 0.0000(10) 0.0129(10) 0.0049(11)
C4 0.0403(15) 0.0316(14) 0.0413(14) -0.0046(11) 0.0196(12) -0.0019(12)
C5 0.0365(15) 0.0386(16) 0.0504(16) -0.0110(13) 0.0169(13) -0.0072(12)
C6 0.0242(12) 0.0449(17) 0.0409(14) -0.0039(12) 0.0094(11) -0.0015(12)
C7 0.0222(11) 0.0335(14) 0.0296(11) 0.0005(10) 0.0074(9) 0.0031(10)
C8 0.0261(12) 0.0321(13) 0.0235(10) 0.0005(9) 0.0111(9) 0.0012(10)
C9 0.0202(12) 0.0506(17) 0.0286(12) -0.0004(11) 0.0011(10) 0.0066(11)
C10 0.0187(11) 0.0442(15) 0.0226(10) -0.0001(10) 0.0041(9) 0.0000(10)
C11 0.0251(12) 0.0436(15) 0.0231(11) -0.0032(10) 0.0079(9) -0.0027(11)
C12 0.0342(14) 0.0485(17) 0.0283(12) -0.0034(11) 0.0116(11) -0.0096(13)
C13 0.0466(16) 0.0407(16) 0.0324(13) -0.0020(11) 0.0196(12) -0.0089(13)
C14 0.0387(14) 0.0433(16) 0.0277(12) 0.0029(11) 0.0151(11) 0.0055(12)
C15 0.0259(12) 0.0356(14) 0.0258(11) -0.0024(10) 0.0094(10) 0.0005(10)
C16 0.0235(11) 0.0393(15) 0.0226(10) -0.0008(10) 0.0098(9) -0.0012(10)
C17 0.0243(12) 0.0228(12) 0.0274(11) 0.0023(9) 0.0018(9) -0.0049(10)
C18 0.0285(13) 0.0258(13) 0.0366(13) 0.0049(10) -0.0054(11) -0.0056(11)
C19 0.0512(19) 0.0425(18) 0.0383(15) 0.0105(13) -0.0072(13) -0.0068(14)
C20 0.0273(14) 0.0369(16) 0.0612(19) 0.0087(14) -0.0011(13) 0.0039(12)
Cl 0.0192(3) 0.0351(3) 0.0272(3) 0.0014(2) 0.0053(2) 0.0001(2)
Cu 0.01583(15) 0.03176(18) 0.02587(15) 0.00330(12) 0.00451(11) 0.00278(12)
N1 0.0242(10) 0.0429(14) 0.0362(11) -0.0006(10) 0.0058(9) 0.0025(10)
N2 0.0286(11) 0.0337(12) 0.0296(10) 0.0035(9) 0.0126(9) 0.0086(9)
N3 0.0215(10) 0.0301(11) 0.0255(9) 0.0020(8) 0.0086(8) 0.0038(8)
N4 0.0175(9) 0.0465(14) 0.0269(10) -0.0025(9) 0.0031(8) -0.0027(9)
N5 0.0183(9) 0.0415(13) 0.0226(9) -0.0005(8) 0.0048(8) 0.0023(9)
O1 0.0311(9) 0.0358(10) 0.0329(9) 0.0027(8) 0.0112(8) -0.0061(8)
O2 0.0185(8) 0.0338(10) 0.0283(8) 0.0061(7) 0.0037(7) 0.0023(7)
O3 0.0450(12) 0.0509(13) 0.0317(10) -0.0083(9) 0.0075(9) -0.0039(10)
O6 0.0255(9) 0.0566(13) 0.0434(11) -0.0038(10) 0.0067(8) 0.0114(9)
O5 0.0309(10) 0.0468(13) 0.0544(12) -0.0069(10) 0.0187(9) -0.0106(9)
O4 0.0464(12) 0.0500(13) 0.0410(11) 0.0173(9) 0.0125(9) 0.0058(10)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 N1 1.464(4) . ?
C1 C2 1.491(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N3 1.330(3) . ?
C2 N2 1.341(3) . ?
C3 C4 1.384(4) . ?
C3 N2 1.386(3) . ?
C3 C8 1.402(4) . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(3) . ?
C7 H7 0.9300 . ?
C8 N3 1.393(3) . ?
C9 C10 1.493(4) . ?
C9 N1 1.493(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N4 1.327(3) . ?
C10 N5 1.335(3) . ?
C11 N4 1.387(3) . ?
C11 C12 1.388(4) . ?
C11 C16 1.401(3) . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.406(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.398(3) . ?
C15 H15 0.9300 . ?
C16 N5 1.405(3) . ?
C17 O1 1.250(3) . ?
C17 O2 1.282(3) . ?
C17 C18 1.508(3) . ?
C18 C19 1.327(4) . ?
C18 C20 1.494(5) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
Cl O4 1.430(2) . ?
Cl O3 1.4339(19) . ?
Cl O5 1.441(2) 1 ?
Cl O5 1.441(2) . ?
Cl O6 1.443(2) . ?
Cu N3 1.961(2) . ?
Cu O2 1.9617(16) . ?
Cu N5 1.973(2) . ?
Cu N1 2.048(2) . ?
Cu O1 2.5554(18) . ?
N1 H1 1.11(4) . ?
N2 H2D 0.8600 . ?
N4 H4D 0.8600 . ?
O5 O5 0.000(6) 1 ?
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
N1 C1 C2 106.2(2) . . ?
N1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
N1 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
N3 C2 N2 112.4(2) . . ?
N3 C2 C1 121.1(2) . . ?
N2 C2 C1 126.5(2) . . ?
C4 C3 N2 131.1(3) . . ?
C4 C3 C8 122.9(2) . . ?
N2 C3 C8 106.0(2) . . ?
C5 C4 C3 116.5(3) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 117.3(2) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
N3 C8 C7 131.8(2) . . ?
N3 C8 C3 108.1(2) . . ?
C7 C8 C3 120.0(2) . . ?
C10 C9 N1 106.1(2) . . ?
C10 C9 H9A 110.5 . . ?
N1 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
N1 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
N4 C10 N5 112.5(2) . . ?
N4 C10 C9 127.4(2) . . ?
N5 C10 C9 120.1(2) . . ?
N4 C11 C12 132.0(2) . . ?
N4 C11 C16 105.6(2) . . ?
C12 C11 C16 122.5(2) . . ?
C13 C12 C11 116.5(2) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 H12 121.8 . . ?
C12 C13 C14 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 117.3(2) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 N5 131.4(2) . . ?
C11 C16 N5 108.2(2) . . ?
O1 C17 O2 121.7(2) . . ?
O1 C17 C18 121.5(2) . . ?
O2 C17 C18 116.9(2) . . ?
C19 C18 C20 124.2(3) . . ?
C19 C18 C17 118.1(3) . . ?
C20 C18 C17 117.7(2) . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 Cl O3 110.46(13) . . ?
O4 Cl O5 108.77(13) . 1 ?
O3 Cl O5 109.41(13) . 1 ?
O4 Cl O5 108.77(13) . . ?
O3 Cl O5 109.41(13) . . ?
O5 Cl O5 0.0(2) 1 . ?
O4 Cl O6 109.79(13) . . ?
O3 Cl O6 109.38(12) . . ?
O5 Cl O6 109.01(13) 1 . ?
O5 Cl O6 109.01(13) . . ?
N3 Cu O2 96.95(8) . . ?
N3 Cu N5 161.64(8) . . ?
O2 Cu N5 99.88(8) . . ?
N3 Cu N1 81.67(9) . . ?
O2 Cu N1 173.84(8) . . ?
N5 Cu N1 82.34(9) . . ?
N3 Cu O1 102.43(7) . . ?
O2 Cu O1 56.81(6) . . ?
N5 Cu O1 92.93(7) . . ?
N1 Cu O1 117.52(8) . . ?
C1 N1 C9 116.0(2) . . ?
C1 N1 Cu 113.25(16) . . ?
C9 N1 Cu 109.88(17) . . ?
C1 N1 H1 108(2) . . ?
C9 N1 H1 107(2) . . ?
Cu N1 H1 102(2) . . ?
C2 N2 C3 107.4(2) . . ?
C2 N2 H2D 126.3 . . ?
C3 N2 H2D 126.3 . . ?
C2 N3 C8 106.0(2) . . ?
C2 N3 Cu 114.22(17) . . ?
C8 N3 Cu 139.74(17) . . ?
C10 N4 C11 108.2(2) . . ?
C10 N4 H4D 125.9 . . ?
C11 N4 H4D 125.9 . . ?
C10 N5 C16 105.4(2) . . ?
C10 N5 Cu 113.36(18) . . ?
C16 N5 Cu 140.68(16) . . ?
C17 O1 Cu 77.33(13) . . ?
C17 O2 Cu 103.79(15) . . ?
O5 O5 Cl 0(3) 1 . ?
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
N1 C1 C2 N3 14.9(3) . . . . ?
N1 C1 C2 N2 -167.0(2) . . . . ?
N2 C3 C4 C5 -178.2(3) . . . . ?
C8 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 N3 177.3(2) . . . . ?
C6 C7 C8 C3 0.3(3) . . . . ?
C4 C3 C8 N3 -177.4(2) . . . . ?
N2 C3 C8 N3 0.8(2) . . . . ?
C4 C3 C8 C7 0.3(4) . . . . ?
N2 C3 C8 C7 178.5(2) . . . . ?
N1 C9 C10 N4 155.4(2) . . . . ?
N1 C9 C10 N5 -24.4(3) . . . . ?
N4 C11 C12 C13 180.0(2) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C14 C15 C16 N5 179.9(2) . . . . ?
N4 C11 C16 C15 180.0(2) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
N4 C11 C16 N5 0.4(3) . . . . ?
C12 C11 C16 N5 -179.6(2) . . . . ?
O1 C17 C18 C19 -8.6(4) . . . . ?
O2 C17 C18 C19 170.6(2) . . . . ?
O1 C17 C18 C20 173.3(2) . . . . ?
O2 C17 C18 C20 -7.5(3) . . . . ?
C2 C1 N1 C9 -148.2(2) . . . . ?
C2 C1 N1 Cu -19.8(2) . . . . ?
C10 C9 N1 C1 160.1(2) . . . . ?
C10 C9 N1 Cu 30.1(2) . . . . ?
N3 Cu N1 C1 16.12(17) . . . . ?
O2 Cu N1 C1 93.6(8) . . . . ?
N5 Cu N1 C1 -154.82(19) . . . . ?
O1 Cu N1 C1 115.85(17) . . . . ?
N3 Cu N1 C9 147.59(19) . . . . ?
O2 Cu N1 C9 -134.9(7) . . . . ?
N5 Cu N1 C9 -23.36(18) . . . . ?
O1 Cu N1 C9 -112.68(18) . . . . ?
N3 C2 N2 C3 0.1(3) . . . . ?
C1 C2 N2 C3 -178.1(2) . . . . ?
C4 C3 N2 C2 177.4(3) . . . . ?
C8 C3 N2 C2 -0.6(2) . . . . ?
N2 C2 N3 C8 0.4(3) . . . . ?
C1 C2 N3 C8 178.8(2) . . . . ?
N2 C2 N3 Cu 179.35(15) . . . . ?
C1 C2 N3 Cu -2.3(3) . . . . ?
C7 C8 N3 C2 -178.0(2) . . . . ?
C3 C8 N3 C2 -0.7(2) . . . . ?
C7 C8 N3 Cu 3.4(4) . . . . ?
C3 C8 N3 Cu -179.29(18) . . . . ?
O2 Cu N3 C2 178.43(16) . . . . ?
N5 Cu N3 C2 22.0(3) . . . . ?
N1 Cu N3 C2 -7.63(16) . . . . ?
O1 Cu N3 C2 -124.11(16) . . . . ?
O2 Cu N3 C8 -3.1(2) . . . . ?
N5 Cu N3 C8 -159.5(2) . . . . ?
N1 Cu N3 C8 170.9(3) . . . . ?
O1 Cu N3 C8 54.4(2) . . . . ?
N5 C10 N4 C11 0.9(3) . . . . ?
C9 C10 N4 C11 -178.9(2) . . . . ?
C12 C11 N4 C10 179.3(3) . . . . ?
C16 C11 N4 C10 -0.8(3) . . . . ?
N4 C10 N5 C16 -0.6(3) . . . . ?
C9 C10 N5 C16 179.2(2) . . . . ?
N4 C10 N5 Cu -174.10(16) . . . . ?
C9 C10 N5 Cu 5.7(3) . . . . ?
C15 C16 N5 C10 -179.4(2) . . . . ?
C11 C16 N5 C10 0.1(3) . . . . ?
C15 C16 N5 Cu -8.9(4) . . . . ?
C11 C16 N5 Cu 170.66(19) . . . . ?
N3 Cu N5 C10 -19.4(4) . . . . ?
O2 Cu N5 C10 -175.55(16) . . . . ?
N1 Cu N5 C10 10.25(17) . . . . ?
O1 Cu N5 C10 127.64(17) . . . . ?
N3 Cu N5 C16 170.5(2) . . . . ?
O2 Cu N5 C16 14.4(3) . . . . ?
N1 Cu N5 C16 -159.8(3) . . . . ?
O1 Cu N5 C16 -42.5(3) . . . . ?
O2 C17 O1 Cu -5.5(2) . . . . ?
C18 C17 O1 Cu 173.7(2) . . . . ?
N3 Cu O1 C17 -86.54(15) . . . . ?
O2 Cu O1 C17 3.68(14) . . . . ?
N5 Cu O1 C17 103.58(15) . . . . ?
N1 Cu O1 C17 -173.53(15) . . . . ?
O1 C17 O2 Cu 7.3(3) . . . . ?
C18 C17 O2 Cu -171.97(18) . . . . ?
N3 Cu O2 C17 96.73(16) . . . . ?
N5 Cu O2 C17 -90.63(16) . . . . ?
N1 Cu O2 C17 20.1(9) . . . . ?
O1 Cu O2 C17 -3.61(14) . . . . ?
O4 Cl O5 O5 0.00(4) . . . 1 ?
O3 Cl O5 O5 0.00(6) . . . 1 ?
O6 Cl O5 O5 0.00(2) . . . 1 ?
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
N4 H4D O6 0.86 2.04 2.881(3) 164.5 4_465
C1 H1B O4 0.97 2.47 3.355(3) 151.5 3_565
C14 H14 O5 0.93 2.49 3.379(4) 161.0 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 27.56
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 1.120
_refine_diff_density_min -0.545
_refine_diff_density_rms 0.070
_database_code_depnum_ccdc_archive 'CCDC 783371'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_1
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C20 H24 Cu N6 O7'
_chemical_formula_weight 523.99
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 17.298(2)
_cell_length_b 8.5102(10)
_cell_length_c 15.4923(18)
_cell_angle_alpha 90.00
_cell_angle_beta 97.711(2)
_cell_angle_gamma 90.00
_cell_volume 2259.9(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description block
_exptl_crystal_colour ?
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.38
_exptl_crystal_size_min 0.30
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.540
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1084
_exptl_absorpt_coefficient_mu 1.021
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.671
_exptl_absorpt_correction_T_max 0.736
_exptl_absorpt_process_details SADABS
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX II area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 15655
_diffrn_reflns_av_R_equivalents 0.0309
_diffrn_reflns_av_sigmaI/netI 0.0282
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 2.38
_diffrn_reflns_theta_max 25.00
_reflns_number_total 3975
_reflns_number_gt 3287
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART APEX II'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
In the refinement, several constrains were applied:
DFIX for C18 C19, C17 C18, H1W1 H1W2, O1W H1W1 H1W2 atoms is used to restrict bond length.
Restraints on the anisotropic temperature factors (DELU and SIMU instructions in SHELXL97)
were used to obtain more meaningful anisotropic displacement ellipsoids,
SIMU for C17 C18 C19 O3 and DELU for C17 C18 C19 O3 atoms.
All H atoms attached to C atoms except for methanol groups
were fixed geometrically and treated as riding with C-H = 0.93 or 0.97\%A with U~iso~(H)=1.2U~eq~(C).
All H atoms attached to N atoms were fixed geometrically and treated
as riding with N-H =0.86\%A with U~iso~(H)=1.2U~eq~(N).
H atoms of water molecule were located in difference Fourier maps and
included in the subsequent refinement using restraints
(O-H=0.84 and 0.86\%A and H-H=1.063\%A) with U~iso~(H)=1.5U~eq~(O).
In the last stage of refinement, they were treated as riding on the O atom.
H atoms attached to O atoms and C atoms at methanol groups were
also calculated geometrically and included into the refinement
with O-H=0.82\%A, U~iso~(H)=1.3U~eq~(O) and C-H=0.96\%A, U~iso~(H)=1.5 U~eq~(C).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1026P)^2^+2.3259P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3975
_refine_ls_number_parameters 312
_refine_ls_number_restraints 28
_refine_ls_R_factor_all 0.0633
_refine_ls_R_factor_gt 0.0506
_refine_ls_wR_factor_ref 0.1621
_refine_ls_wR_factor_gt 0.1525
_refine_ls_goodness_of_fit_ref 1.120
_refine_ls_restrained_S_all 1.199
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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
C19 C 0.1250(5) -0.2320(9) 1.0601(5) 0.091(2) Uani 1 1 d DU . .
H19A H 0.1584 -0.2950 1.0329 0.109 Uiso 1 1 calc R . .
H19B H 0.0945 -0.2763 1.0989 0.109 Uiso 1 1 calc R . .
Cu Cu 0.26810(3) 0.03166(5) 0.86161(3) 0.0226(2) Uani 1 1 d . . .
O4 O 0.39220(19) 0.6051(4) -0.0275(2) 0.0437(8) Uani 1 1 d . . .
O5 O 0.4256(3) 0.5416(4) 0.1063(3) 0.0637(12) Uani 1 1 d . . .
O6 O 0.3062(3) 0.5167(5) 0.0494(3) 0.0652(12) Uani 1 1 d . . .
O2 O 0.20369(16) -0.0799(3) 0.93579(17) 0.0289(6) Uani 1 1 d . . .
O1W O 0.2291(2) 0.3684(5) 0.8921(2) 0.0572(10) Uani 1 1 d D . .
H1W1 H 0.2111 0.4370 0.9234 0.086 Uiso 1 1 d RD . .
H1W2 H 0.2149 0.3137 0.9342 0.086 Uiso 1 1 d RD . .
O3 O 0.1612(2) 0.1446(4) 0.98799(19) 0.0441(8) Uani 1 1 d U . .
N1 N 0.3389(2) 0.1508(4) 0.7834(2) 0.0325(8) Uani 1 1 d . . .
H1 H 0.3358 0.0516 0.7931 0.039 Uiso 1 1 calc R . .
N3 N 0.1889(2) 0.0625(4) 0.7597(2) 0.0249(7) Uani 1 1 d . . .
N2 N 0.1543(2) 0.1830(4) 0.6330(2) 0.0307(8) Uani 1 1 d . . .
H2D H 0.1581 0.2401 0.5880 0.037 Uiso 1 1 calc R . .
N5 N 0.35803(19) 0.0756(4) 0.9508(2) 0.0229(7) Uani 1 1 d . . .
N6 N 0.3743(2) 0.5537(4) 0.0434(3) 0.0393(10) Uani 1 1 d . . .
N4 N 0.46192(19) 0.2219(4) 0.9926(2) 0.0270(7) Uani 1 1 d . . .
H7 H 0.4981 0.2905 0.9904 0.032 Uiso 1 1 calc R . .
C1 C 0.2908(2) 0.2291(5) 0.7099(2) 0.0286(9) Uani 1 1 d . . .
H1A H 0.3143 0.2159 0.6570 0.034 Uiso 1 1 calc R . .
H1B H 0.2870 0.3406 0.7216 0.034 Uiso 1 1 calc R . .
C2 C 0.2113(2) 0.1557(5) 0.6995(2) 0.0262(8) Uani 1 1 d . . .
C3 C 0.0888(3) 0.1024(5) 0.6504(3) 0.0311(9) Uani 1 1 d . . .
C4 C 0.0145(3) 0.0920(6) 0.6052(3) 0.0385(10) Uani 1 1 d . . .
H4A H 0.0007 0.1443 0.5527 0.046 Uiso 1 1 calc R . .
C5 C -0.0382(3) 0.0002(6) 0.6417(3) 0.0427(11) Uani 1 1 d . . .
H5A H -0.0886 -0.0104 0.6127 0.051 Uiso 1 1 calc R . .
C6 C -0.0180(3) -0.0775(6) 0.7210(3) 0.0419(11) Uani 1 1 d . . .
H6A H -0.0555 -0.1375 0.7438 0.050 Uiso 1 1 calc R . .
C7 C 0.0568(3) -0.0673(5) 0.7669(3) 0.0344(10) Uani 1 1 d . . .
H7A H 0.0703 -0.1203 0.8192 0.041 Uiso 1 1 calc R . .
C8 C 0.1105(3) 0.0256(5) 0.7309(3) 0.0280(9) Uani 1 1 d . . .
C9 C 0.3928(2) 0.2557(5) 0.8394(3) 0.0280(9) Uani 1 1 d . . .
H9A H 0.3703 0.3598 0.8415 0.034 Uiso 1 1 calc R . .
H9B H 0.4420 0.2645 0.8164 0.034 Uiso 1 1 calc R . .
C11 C 0.4514(2) 0.1282(5) 1.0637(3) 0.0274(9) Uani 1 1 d . . .
C12 C 0.4939(3) 0.1140(5) 1.1468(3) 0.0332(10) Uani 1 1 d . . .
H12A H 0.5371 0.1767 1.1647 0.040 Uiso 1 1 calc R . .
C13 C 0.4682(3) 0.0021(5) 1.2005(3) 0.0322(10) Uani 1 1 d . . .
H13A H 0.4950 -0.0115 1.2562 0.039 Uiso 1 1 calc R . .
C14 C 0.4023(3) -0.0926(5) 1.1735(3) 0.0328(10) Uani 1 1 d . . .
H14A H 0.3870 -0.1673 1.2116 0.039 Uiso 1 1 calc R . .
C15 C 0.3601(2) -0.0766(5) 1.0916(2) 0.0260(8) Uani 1 1 d . . .
H15A H 0.3166 -0.1386 1.0740 0.031 Uiso 1 1 calc R . .
C16 C 0.3854(2) 0.0355(4) 1.0368(3) 0.0235(8) Uani 1 1 d . . .
C10 C 0.4053(2) 0.1854(4) 0.9284(2) 0.0249(8) Uani 1 1 d . . .
C17 C 0.1650(3) -0.0032(6) 0.9858(3) 0.0371(9) Uani 1 1 d DU . .
C18 C 0.1210(3) -0.0884(8) 1.0447(3) 0.0572(13) Uani 1 1 d DU . .
H18 H 0.0867 -0.0302 1.0734 0.069 Uiso 1 1 calc R . .
O1 O 0.30858(18) -0.2213(3) 0.8273(2) 0.0320(7) Uani 1 1 d . . .
C20 C 0.2428(3) -0.3041(6) 0.7800(4) 0.0534(14) Uani 1 1 d . . .
H20A H 0.1993 -0.2997 0.8125 0.080 Uiso 1 1 calc R . .
H20B H 0.2568 -0.4118 0.7721 0.080 Uiso 1 1 calc R . .
H20C H 0.2287 -0.2556 0.7242 0.080 Uiso 1 1 calc R . .
H1C H 0.328(3) -0.264(6) 0.873(3) 0.042(15) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C19 0.101(5) 0.104(4) 0.067(4) 0.014(4) 0.004(4) -0.033(4)
Cu 0.0238(3) 0.0228(3) 0.0210(3) 0.00260(17) 0.0022(2) -0.00381(18)
O4 0.0418(19) 0.0364(18) 0.053(2) 0.0055(15) 0.0047(15) -0.0032(15)
O5 0.076(3) 0.039(2) 0.064(3) -0.0079(17) -0.037(2) 0.0091(19)
O6 0.055(3) 0.072(3) 0.069(3) 0.011(2) 0.009(2) -0.028(2)
O2 0.0301(16) 0.0315(15) 0.0254(14) 0.0016(12) 0.0041(12) -0.0070(13)
O1W 0.041(2) 0.070(3) 0.059(2) 0.010(2) 0.0050(17) 0.0047(19)
O3 0.053(2) 0.0503(18) 0.0307(16) -0.0126(14) 0.0112(14) 0.0025(16)
N1 0.036(2) 0.0274(18) 0.0344(19) 0.0048(15) 0.0060(16) -0.0040(15)
N3 0.0294(18) 0.0229(16) 0.0221(16) 0.0023(13) 0.0020(13) -0.0040(14)
N2 0.038(2) 0.0344(19) 0.0199(16) 0.0050(14) 0.0036(14) -0.0005(16)
N5 0.0230(17) 0.0208(15) 0.0249(16) 0.0000(13) 0.0031(13) -0.0005(14)
N6 0.042(2) 0.0233(18) 0.049(2) -0.0004(16) -0.0089(19) -0.0036(16)
N4 0.0243(18) 0.0209(16) 0.0355(18) -0.0043(13) 0.0030(14) -0.0050(14)
C1 0.032(2) 0.029(2) 0.0254(19) 0.0036(16) 0.0067(17) -0.0019(18)
C2 0.032(2) 0.028(2) 0.0185(17) -0.0002(15) 0.0034(15) 0.0004(17)
C3 0.034(2) 0.031(2) 0.027(2) -0.0013(17) -0.0001(17) 0.0025(18)
C4 0.042(3) 0.040(3) 0.031(2) -0.003(2) -0.0043(19) 0.002(2)
C5 0.036(3) 0.049(3) 0.040(3) -0.005(2) -0.007(2) -0.006(2)
C6 0.036(3) 0.048(3) 0.041(3) -0.003(2) 0.003(2) -0.011(2)
C7 0.035(2) 0.036(2) 0.031(2) -0.0009(18) 0.0016(18) -0.007(2)
C8 0.029(2) 0.031(2) 0.023(2) -0.0021(16) -0.0005(16) -0.0005(17)
C9 0.025(2) 0.025(2) 0.035(2) 0.0039(16) 0.0071(17) -0.0012(16)
C11 0.027(2) 0.023(2) 0.032(2) -0.0082(16) 0.0031(17) 0.0034(16)
C12 0.029(2) 0.034(2) 0.034(2) -0.0161(18) -0.0019(17) 0.0046(18)
C13 0.032(2) 0.039(2) 0.024(2) -0.0093(18) -0.0001(17) 0.0109(19)
C14 0.036(2) 0.037(2) 0.026(2) -0.0004(18) 0.0072(18) 0.0117(19)
C15 0.026(2) 0.0251(19) 0.027(2) -0.0028(16) 0.0048(16) 0.0037(16)
C16 0.021(2) 0.025(2) 0.0242(19) -0.0040(15) 0.0022(15) 0.0062(15)
C10 0.024(2) 0.0203(18) 0.031(2) -0.0007(15) 0.0056(16) 0.0043(15)
C17 0.028(2) 0.064(2) 0.0184(18) -0.0016(18) -0.0010(16) -0.008(2)
C18 0.045(3) 0.096(3) 0.031(2) 0.010(2) 0.008(2) -0.022(3)
O1 0.0348(17) 0.0260(15) 0.0355(17) 0.0003(13) 0.0055(13) -0.0006(13)
C20 0.056(3) 0.039(3) 0.065(3) -0.014(2) 0.006(3) -0.001(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C19 C18 1.245(7) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
Cu O2 1.951(3) . ?
Cu N3 1.964(3) . ?
Cu N5 1.973(3) . ?
Cu N1 2.095(3) . ?
Cu O1 2.347(3) . ?
O4 N6 1.259(5) . ?
O5 N6 1.230(5) . ?
O6 N6 1.235(6) . ?
O2 C17 1.271(6) . ?
O1W H1W1 0.8454 . ?
O1W H1W2 0.8636 . ?
O3 C17 1.260(6) . ?
N1 C1 1.475(5) . ?
N1 C9 1.484(5) . ?
N1 H1 0.8600 . ?
N3 C2 1.320(5) . ?
N3 C8 1.405(5) . ?
N2 C2 1.346(5) . ?
N2 C3 1.382(6) . ?
N2 H2D 0.8600 . ?
N5 C10 1.319(5) . ?
N5 C16 1.394(5) . ?
N4 C10 1.336(5) . ?
N4 C11 1.392(5) . ?
N4 H7 0.8600 . ?
C1 C2 1.500(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C4 1.381(6) . ?
C3 C8 1.415(6) . ?
C4 C5 1.378(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.399(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.393(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.392(6) . ?
C7 H7A 0.9300 . ?
C9 C10 1.491(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.399(6) . ?
C11 C16 1.404(6) . ?
C12 C13 1.377(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.413(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.382(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.387(6) . ?
C15 H15A 0.9300 . ?
C17 C18 1.457(6) . ?
C18 H18 0.9300 . ?
O1 C20 1.451(6) . ?
O1 H1C 0.82(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
O2 Cu N3 98.44(13) . . ?
O2 Cu N5 97.96(12) . . ?
N3 Cu N5 159.56(14) . . ?
O2 Cu N1 179.07(13) . . ?
N3 Cu N1 82.48(14) . . ?
N5 Cu N1 81.17(13) . . ?
O2 Cu O1 84.15(11) . . ?
N3 Cu O1 97.92(13) . . ?
N5 Cu O1 95.82(12) . . ?
N1 Cu O1 95.62(12) . . ?
C17 O2 Cu 119.9(3) . . ?
H1W1 O1W H1W2 76.9 . . ?
C1 N1 C9 115.1(3) . . ?
C1 N1 Cu 110.6(2) . . ?
C9 N1 Cu 108.9(2) . . ?
C1 N1 H1 122.5 . . ?
C9 N1 H1 122.5 . . ?
Cu N1 H1 51.0 . . ?
C2 N3 C8 105.8(3) . . ?
C2 N3 Cu 114.1(3) . . ?
C8 N3 Cu 139.9(3) . . ?
C2 N2 C3 107.5(3) . . ?
C2 N2 H2D 126.2 . . ?
C3 N2 H2D 126.2 . . ?
C10 N5 C16 106.4(3) . . ?
C10 N5 Cu 114.1(3) . . ?
C16 N5 Cu 139.2(3) . . ?
O5 N6 O6 120.8(5) . . ?
O5 N6 O4 119.0(4) . . ?
O6 N6 O4 120.1(4) . . ?
C10 N4 C11 107.2(3) . . ?
C10 N4 H7 126.4 . . ?
C11 N4 H7 126.4 . . ?
N1 C1 C2 108.0(3) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N3 C2 N2 113.0(4) . . ?
N3 C2 C1 121.7(3) . . ?
N2 C2 C1 125.2(3) . . ?
C4 C3 N2 131.7(4) . . ?
C4 C3 C8 122.5(4) . . ?
N2 C3 C8 105.8(4) . . ?
C5 C4 C3 116.7(4) . . ?
C5 C4 H4A 121.6 . . ?
C3 C4 H4A 121.6 . . ?
C4 C5 C6 121.9(5) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C7 C6 C5 121.6(4) . . ?
C7 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
C8 C7 C6 117.1(4) . . ?
C8 C7 H7A 121.4 . . ?
C6 C7 H7A 121.4 . . ?
C7 C8 N3 131.9(4) . . ?
C7 C8 C3 120.2(4) . . ?
N3 C8 C3 107.9(4) . . ?
N1 C9 C10 107.5(3) . . ?
N1 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
N1 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N4 C11 C12 132.0(4) . . ?
N4 C11 C16 105.9(3) . . ?
C12 C11 C16 122.1(4) . . ?
C13 C12 C11 116.3(4) . . ?
C13 C12 H12A 121.8 . . ?
C11 C12 H12A 121.8 . . ?
C12 C13 C14 121.9(4) . . ?
C12 C13 H13A 119.1 . . ?
C14 C13 H13A 119.1 . . ?
C15 C14 C13 121.4(4) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C14 C15 C16 117.3(4) . . ?
C14 C15 H15A 121.3 . . ?
C16 C15 H15A 121.3 . . ?
C15 C16 N5 131.2(4) . . ?
C15 C16 C11 120.9(4) . . ?
N5 C16 C11 107.8(3) . . ?
N5 C10 N4 112.8(3) . . ?
N5 C10 C9 120.6(3) . . ?
N4 C10 C9 126.6(4) . . ?
O3 C17 O2 124.2(4) . . ?
O3 C17 C18 116.5(5) . . ?
O2 C17 C18 119.2(5) . . ?
C19 C18 C17 126.0(7) . . ?
C19 C18 H18 117.0 . . ?
C17 C18 H18 117.0 . . ?
C20 O1 Cu 108.8(3) . . ?
C20 O1 H1C 115(4) . . ?
Cu O1 H1C 108(4) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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
N3 Cu O2 C17 -88.7(3) . . . . ?
N5 Cu O2 C17 79.0(3) . . . . ?
O1 Cu O2 C17 174.1(3) . . . . ?
N3 Cu N1 C1 15.4(3) . . . . ?
N5 Cu N1 C1 -152.3(3) . . . . ?
O1 Cu N1 C1 112.7(3) . . . . ?
N3 Cu N1 C9 142.8(3) . . . . ?
N5 Cu N1 C9 -24.9(3) . . . . ?
O1 Cu N1 C9 -119.9(3) . . . . ?
O2 Cu N3 C2 171.3(3) . . . . ?
N5 Cu N3 C2 28.3(5) . . . . ?
N1 Cu N3 C2 -8.8(3) . . . . ?
O1 Cu N3 C2 -103.5(3) . . . . ?
O2 Cu N3 C8 -2.2(4) . . . . ?
N5 Cu N3 C8 -145.2(4) . . . . ?
N1 Cu N3 C8 177.7(4) . . . . ?
O1 Cu N3 C8 83.0(4) . . . . ?
O2 Cu N5 C10 -163.5(3) . . . . ?
N3 Cu N5 C10 -20.4(5) . . . . ?
N1 Cu N5 C10 16.8(3) . . . . ?
O1 Cu N5 C10 111.6(3) . . . . ?
O2 Cu N5 C16 9.0(4) . . . . ?
N3 Cu N5 C16 152.1(4) . . . . ?
N1 Cu N5 C16 -170.7(4) . . . . ?
O1 Cu N5 C16 -75.9(4) . . . . ?
C9 N1 C1 C2 -141.9(3) . . . . ?
Cu N1 C1 C2 -18.0(4) . . . . ?
C8 N3 C2 N2 -0.3(4) . . . . ?
Cu N3 C2 N2 -176.0(3) . . . . ?
C8 N3 C2 C1 176.0(4) . . . . ?
Cu N3 C2 C1 0.3(5) . . . . ?
C3 N2 C2 N3 0.4(5) . . . . ?
C3 N2 C2 C1 -175.8(4) . . . . ?
N1 C1 C2 N3 12.5(5) . . . . ?
N1 C1 C2 N2 -171.6(4) . . . . ?
C2 N2 C3 C4 178.7(5) . . . . ?
C2 N2 C3 C8 -0.2(4) . . . . ?
N2 C3 C4 C5 -179.7(5) . . . . ?
C8 C3 C4 C5 -0.9(7) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
C4 C5 C6 C7 -0.7(8) . . . . ?
C5 C6 C7 C8 0.9(7) . . . . ?
C6 C7 C8 N3 179.1(4) . . . . ?
C6 C7 C8 C3 -1.1(6) . . . . ?
C2 N3 C8 C7 179.9(5) . . . . ?
Cu N3 C8 C7 -6.2(8) . . . . ?
C2 N3 C8 C3 0.2(4) . . . . ?
Cu N3 C8 C3 174.0(3) . . . . ?
C4 C3 C8 C7 1.2(6) . . . . ?
N2 C3 C8 C7 -179.7(4) . . . . ?
C4 C3 C8 N3 -179.0(4) . . . . ?
N2 C3 C8 N3 0.0(4) . . . . ?
C1 N1 C9 C10 152.1(3) . . . . ?
Cu N1 C9 C10 27.3(4) . . . . ?
C10 N4 C11 C12 178.3(4) . . . . ?
C10 N4 C11 C16 0.0(4) . . . . ?
N4 C11 C12 C13 -177.1(4) . . . . ?
C16 C11 C12 C13 1.0(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C16 0.4(6) . . . . ?
C14 C15 C16 N5 177.2(4) . . . . ?
C14 C15 C16 C11 0.2(6) . . . . ?
C10 N5 C16 C15 -177.2(4) . . . . ?
Cu N5 C16 C15 10.0(7) . . . . ?
C10 N5 C16 C11 0.1(4) . . . . ?
Cu N5 C16 C11 -172.8(3) . . . . ?
N4 C11 C16 C15 177.5(3) . . . . ?
C12 C11 C16 C15 -1.0(6) . . . . ?
N4 C11 C16 N5 -0.1(4) . . . . ?
C12 C11 C16 N5 -178.6(3) . . . . ?
C16 N5 C10 N4 -0.1(4) . . . . ?
Cu N5 C10 N4 174.8(2) . . . . ?
C16 N5 C10 C9 180.0(3) . . . . ?
Cu N5 C10 C9 -5.1(4) . . . . ?
C11 N4 C10 N5 0.1(4) . . . . ?
C11 N4 C10 C9 180.0(4) . . . . ?
N1 C9 C10 N5 -16.0(5) . . . . ?
N1 C9 C10 N4 164.1(4) . . . . ?
Cu O2 C17 O3 4.3(6) . . . . ?
Cu O2 C17 C18 -176.3(3) . . . . ?
O3 C17 C18 C19 -170.4(6) . . . . ?
O2 C17 C18 C19 10.2(9) . . . . ?
O2 Cu O1 C20 66.4(3) . . . . ?
N3 Cu O1 C20 -31.3(3) . . . . ?
N5 Cu O1 C20 163.8(3) . . . . ?
N1 Cu O1 C20 -114.5(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 2.230
_refine_diff_density_min -0.868
_refine_diff_density_rms 0.103
_database_code_depnum_ccdc_archive 'CCDC 800074'