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A fluoro­phore-labelled copper(II) complex, aqua­bis­(di­methyl­formamide-κO)(perchlorato-κO)[2-(quinolin-2-yl)-1,3-oxazolo[4,5-f][1,10]phenanthroline]copper(II) perchlorate monohydrate, [Cu(ClO4)(C22H12N4O)(C3H7NO)2(H2O)]ClO4·H2O, has been synthesized and characterized. A cyclic hydrogen-bonded water–perchlorate anionic cluster, i.e. [(ClO4)2(H2O)2]2−, has been identified within the structure. Each cyclic anionic cluster unit is inter­connected by hydrogen bonding to the cation. The cations join into an infinite hydrogen-bonded chain running in the [010] direction. Furthermore, inter­action of the complex with calf-thymus DNA (CT-DNA) and cellular localization within the cells was explored. Spectroscopic studies indicate that the compound has a good affinity for DNA and stains the nucleus of the cells.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617011639/sk3665sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011639/sk3665Isup2.hkl
Contains datablock I

CCDC reference: 1562837

Computing details top

Data collection: SAINT (Bruker, 2010); cell refinement: SMART (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Aquabis(dimethylformamide-κO)(perchlorato-κO)[2-(quinolin-2-yl)-1,3-oxazolo[4,5-f][1,10]phenanthroline]copper(II) perchlorate monohydrate top
Crystal data top
[Cu(ClO4)(C22H12N4O)(C3H7NO)2(H2O)]ClO4·H2OF(000) = 3256
Mr = 793.02Dx = 1.612 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
a = 48.675 (3) ÅCell parameters from 4790 reflections
b = 8.3750 (5) Åθ = 1.9–64.5°
c = 16.3155 (9) ŵ = 3.12 mm1
β = 100.716 (2)°T = 173 K
V = 6535.1 (6) Å3Rectangle, green
Z = 80.28 × 0.22 × 0.17 mm
Data collection top
Bruker X8 Proteum
diffractometer
4790 reflections with I > 2σ(I)
φ and ω scansRint = 0.071
Absorption correction: multi-scan
(SADABS; Bruker, 2010)
θmax = 64.5°, θmin = 5.4°
Tmin = 0.482, Tmax = 0.505h = 5654
29422 measured reflectionsk = 99
5417 independent reflectionsl = 1519
Refinement top
Refinement on F2157 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0731P)2 + 16.1488P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
5417 reflectionsΔρmax = 0.77 e Å3
504 parametersΔρmin = 0.48 e Å3
Special details top

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.63808 (2)0.76800 (5)0.33515 (3)0.01822 (15)
O20.67770 (4)0.8210 (3)0.37130 (13)0.0231 (5)
O10.64467 (4)0.6953 (3)0.22641 (13)0.0232 (5)
O30.54145 (4)1.1271 (2)0.48962 (12)0.0212 (4)
O40.65005 (5)0.5336 (3)0.39334 (14)0.0283 (5)
H4A0.6686800.5141380.3995430.042*
H4B0.6413110.4524830.3622160.042*
N20.59662 (5)0.7598 (3)0.29512 (15)0.0172 (5)
N10.62665 (5)0.8758 (3)0.43273 (14)0.0187 (5)
N40.51555 (5)1.0462 (3)0.36830 (15)0.0176 (5)
N70.71619 (5)0.9632 (3)0.36123 (16)0.0231 (6)
N50.49830 (5)1.2951 (3)0.53244 (15)0.0189 (5)
O50.70583 (5)0.4386 (3)0.44686 (19)0.0468 (7)
H5A0.7189000.4383230.4186260.070*
H5B0.7068900.3473750.4700570.070*
N60.66992 (5)0.5341 (3)0.15751 (17)0.0284 (6)
C50.58248 (5)0.8501 (3)0.34240 (17)0.0164 (6)
C60.59897 (6)0.9109 (3)0.41920 (18)0.0171 (6)
C40.55404 (5)0.8880 (3)0.31771 (17)0.0171 (6)
C10.58274 (6)0.7023 (3)0.22309 (18)0.0195 (6)
H10.5921330.6367160.1914530.023*
C260.68925 (6)0.9459 (4)0.35209 (19)0.0236 (7)
H260.6779141.0307850.3301070.028*
C30.54021 (6)0.8312 (3)0.23980 (18)0.0196 (6)
H30.5215890.8571810.2199600.024*
C110.55818 (6)1.0365 (3)0.44858 (18)0.0183 (6)
C230.66611 (6)0.6122 (4)0.22322 (19)0.0234 (7)
H230.6799920.6067360.2707490.028*
C220.47685 (6)1.3819 (3)0.55422 (19)0.0209 (6)
C70.58712 (6)1.0027 (3)0.47580 (18)0.0186 (6)
C130.51640 (6)1.1273 (3)0.43692 (19)0.0208 (6)
C120.54243 (6)0.9866 (3)0.37484 (18)0.0184 (6)
C20.55461 (6)0.7368 (4)0.19342 (19)0.0212 (6)
H20.5456390.6959990.1424040.025*
C80.60458 (6)1.0527 (4)0.54982 (19)0.0246 (7)
H80.5973891.1111960.5894690.030*
C150.46711 (6)1.2196 (4)0.4050 (2)0.0227 (6)
H150.4646761.1640730.3548470.027*
C100.64288 (6)0.9274 (4)0.50227 (19)0.0228 (6)
H100.6619220.9050870.5110600.027*
C170.44993 (6)1.3887 (4)0.5025 (2)0.0242 (7)
C140.49310 (6)1.2182 (3)0.46072 (18)0.0181 (6)
C90.63232 (6)1.0138 (4)0.5625 (2)0.0263 (7)
H90.6441511.0450970.6113410.032*
C160.44565 (6)1.3050 (4)0.4270 (2)0.0269 (7)
H160.4282641.3074460.3918280.032*
C210.48177 (7)1.4658 (4)0.6303 (2)0.0278 (7)
H210.4993201.4610980.6644760.033*
C180.42873 (7)1.4798 (4)0.5304 (2)0.0339 (8)
H180.4109161.4849710.4978070.041*
C200.46102 (8)1.5540 (4)0.6545 (2)0.0364 (9)
H200.4647071.6105820.7043940.044*
C190.43436 (8)1.5600 (4)0.6050 (3)0.0396 (9)
H190.4203301.6187730.6226610.048*
C270.72853 (8)1.1103 (4)0.3384 (2)0.0389 (8)
H27A0.7139951.1855410.3178830.058*
H27B0.7392001.0888330.2956810.058*
H27C0.7405861.1539870.3864350.058*
C240.64950 (9)0.5388 (6)0.0826 (3)0.0556 (12)
H24A0.6323320.5813080.0943680.083*
H24B0.6463430.4327030.0605850.083*
H24C0.6560750.6054750.0424650.083*
C280.73515 (7)0.8364 (5)0.3937 (3)0.0517 (11)
H28A0.7252170.7559030.4183780.078*
H28B0.7499540.8785600.4352680.078*
H28C0.7429040.7901480.3492250.078*
C250.69518 (9)0.4426 (5)0.1565 (3)0.0512 (11)
H25A0.7074120.4514780.2097480.077*
H25B0.7044330.4832560.1138080.077*
H25C0.6904000.3324880.1454030.077*
Cl30.61575 (2)1.19401 (9)0.26661 (5)0.0271 (2)
O320.62515 (6)1.2378 (3)0.35322 (16)0.0436 (6)
O310.62935 (5)1.0488 (3)0.25143 (15)0.0358 (6)
O330.62201 (5)1.3185 (3)0.21300 (17)0.0414 (6)
O340.58625 (5)1.1691 (4)0.2537 (2)0.0533 (8)
Cl20.72028 (14)0.0671 (7)0.6164 (4)0.0330 (12)0.6667
O60.72004 (11)0.1404 (8)0.5356 (3)0.0508 (14)0.6667
O70.74955 (14)0.0373 (12)0.6530 (4)0.0347 (14)0.6667
O80.70409 (11)0.0720 (6)0.6185 (4)0.0594 (13)0.6667
O90.71221 (14)0.1840 (7)0.6718 (4)0.0653 (18)0.6667
Cl10.7185 (2)0.0605 (13)0.6059 (8)0.0297 (19)0.3333
O100.7077 (3)0.1569 (17)0.5390 (9)0.075 (3)0.3333
O110.7465 (3)0.040 (3)0.6321 (12)0.061 (4)0.3333
O130.71045 (14)0.0957 (9)0.5766 (6)0.0345 (16)0.3333
O120.7028 (2)0.1098 (15)0.6623 (7)0.062 (3)0.3333
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0134 (2)0.0240 (3)0.0190 (3)0.00191 (15)0.00771 (17)0.00228 (17)
O20.0155 (10)0.0281 (11)0.0273 (11)0.0012 (8)0.0081 (8)0.0001 (9)
O10.0179 (10)0.0317 (11)0.0217 (11)0.0055 (8)0.0081 (8)0.0015 (9)
O30.0188 (10)0.0232 (11)0.0244 (11)0.0035 (8)0.0116 (8)0.0004 (9)
O40.0319 (12)0.0250 (11)0.0287 (12)0.0029 (9)0.0075 (9)0.0020 (9)
N20.0173 (12)0.0187 (12)0.0178 (13)0.0007 (9)0.0092 (10)0.0011 (10)
N10.0174 (12)0.0224 (12)0.0177 (13)0.0008 (9)0.0070 (10)0.0009 (10)
N40.0168 (12)0.0162 (12)0.0230 (13)0.0009 (9)0.0125 (10)0.0019 (10)
N70.0224 (13)0.0245 (13)0.0244 (14)0.0028 (10)0.0091 (10)0.0018 (11)
N50.0196 (12)0.0185 (12)0.0212 (13)0.0001 (9)0.0111 (10)0.0032 (10)
O50.0396 (15)0.0463 (16)0.0588 (18)0.0157 (12)0.0204 (13)0.0135 (13)
N60.0282 (14)0.0332 (15)0.0278 (15)0.0035 (11)0.0152 (12)0.0062 (12)
C50.0171 (13)0.0164 (14)0.0177 (14)0.0015 (11)0.0086 (11)0.0019 (11)
C60.0164 (13)0.0182 (14)0.0188 (15)0.0014 (11)0.0086 (11)0.0016 (12)
C40.0168 (13)0.0167 (14)0.0206 (15)0.0028 (11)0.0110 (11)0.0036 (11)
C10.0210 (14)0.0215 (15)0.0185 (15)0.0017 (11)0.0103 (12)0.0013 (12)
C260.0235 (16)0.0230 (16)0.0244 (17)0.0019 (12)0.0046 (12)0.0025 (13)
C30.0154 (13)0.0228 (15)0.0227 (16)0.0017 (11)0.0086 (11)0.0047 (12)
C110.0195 (14)0.0162 (14)0.0231 (16)0.0006 (11)0.0141 (12)0.0006 (12)
C230.0217 (15)0.0276 (16)0.0233 (16)0.0001 (12)0.0105 (12)0.0010 (13)
C220.0253 (15)0.0151 (14)0.0263 (16)0.0023 (11)0.0154 (13)0.0051 (12)
C70.0198 (14)0.0198 (14)0.0191 (15)0.0005 (11)0.0108 (12)0.0007 (12)
C130.0173 (14)0.0172 (14)0.0310 (17)0.0005 (11)0.0129 (12)0.0066 (13)
C120.0180 (14)0.0164 (14)0.0232 (16)0.0009 (11)0.0105 (12)0.0038 (12)
C20.0213 (15)0.0261 (16)0.0173 (15)0.0061 (12)0.0064 (12)0.0021 (12)
C80.0260 (16)0.0299 (16)0.0204 (16)0.0006 (13)0.0105 (13)0.0041 (13)
C150.0220 (15)0.0240 (16)0.0236 (16)0.0015 (12)0.0080 (12)0.0008 (12)
C100.0171 (14)0.0299 (16)0.0219 (16)0.0008 (12)0.0052 (12)0.0010 (13)
C170.0223 (15)0.0200 (15)0.0345 (18)0.0022 (12)0.0162 (13)0.0059 (13)
C140.0191 (14)0.0148 (14)0.0234 (16)0.0008 (11)0.0119 (12)0.0030 (12)
C90.0245 (15)0.0362 (18)0.0184 (16)0.0022 (13)0.0043 (12)0.0046 (13)
C160.0164 (14)0.0281 (17)0.0368 (19)0.0009 (12)0.0063 (13)0.0050 (14)
C210.0393 (18)0.0216 (16)0.0265 (18)0.0007 (13)0.0165 (14)0.0055 (13)
C180.0248 (16)0.0272 (17)0.055 (2)0.0093 (13)0.0221 (16)0.0100 (16)
C200.061 (2)0.0200 (16)0.037 (2)0.0024 (15)0.0318 (18)0.0028 (14)
C190.049 (2)0.0232 (17)0.059 (3)0.0109 (15)0.042 (2)0.0075 (17)
C270.0381 (19)0.0350 (19)0.044 (2)0.0129 (15)0.0093 (16)0.0012 (16)
C240.056 (3)0.076 (3)0.036 (2)0.014 (2)0.0115 (19)0.019 (2)
C280.0207 (17)0.039 (2)0.096 (3)0.0010 (15)0.0124 (19)0.018 (2)
C250.057 (2)0.054 (3)0.049 (2)0.027 (2)0.029 (2)0.005 (2)
Cl30.0253 (4)0.0231 (4)0.0345 (4)0.0010 (3)0.0093 (3)0.0036 (3)
O320.0667 (18)0.0310 (13)0.0356 (15)0.0074 (12)0.0161 (13)0.0069 (11)
O310.0470 (14)0.0308 (13)0.0329 (13)0.0096 (10)0.0157 (11)0.0021 (10)
O330.0415 (14)0.0339 (13)0.0506 (16)0.0068 (11)0.0132 (12)0.0131 (12)
O340.0236 (13)0.0569 (17)0.078 (2)0.0019 (12)0.0051 (12)0.0301 (16)
Cl20.035 (2)0.0304 (14)0.0318 (15)0.0038 (10)0.0015 (10)0.0079 (10)
O60.058 (3)0.061 (3)0.031 (2)0.020 (3)0.003 (2)0.013 (2)
O70.030 (3)0.042 (3)0.030 (3)0.001 (2)0.0012 (19)0.010 (2)
O80.0562 (19)0.0482 (18)0.068 (2)0.0204 (14)0.0038 (16)0.0132 (16)
O90.087 (5)0.054 (3)0.069 (4)0.010 (3)0.049 (3)0.000 (3)
Cl10.023 (3)0.027 (2)0.041 (4)0.0043 (18)0.012 (3)0.003 (2)
O100.108 (9)0.052 (5)0.063 (5)0.023 (6)0.013 (5)0.026 (5)
O110.021 (3)0.048 (7)0.111 (12)0.004 (3)0.006 (4)0.003 (8)
O130.019 (3)0.030 (2)0.052 (5)0.000 (2)0.000 (3)0.001 (3)
O120.054 (6)0.084 (7)0.052 (4)0.032 (5)0.018 (5)0.005 (5)
Geometric parameters (Å, º) top
Cu1—O21.960 (2)C13—C141.477 (4)
Cu1—O11.958 (2)C2—H20.9300
Cu1—O42.211 (2)C8—H80.9300
Cu1—N22.003 (2)C8—C91.367 (4)
Cu1—N11.997 (2)C15—H150.9300
Cu1—O312.713 (2)C15—C141.414 (4)
O2—C261.255 (4)C15—C161.367 (4)
O1—C231.264 (4)C10—H100.9300
O3—C111.375 (3)C10—C91.393 (4)
O3—C131.355 (4)C17—C161.399 (5)
O4—H4A0.9082C17—C181.425 (4)
O4—H4B0.9052C9—H90.9300
N2—C51.356 (4)C16—H160.9300
N2—C11.332 (4)C21—H210.9300
N1—C61.357 (4)C21—C201.368 (5)
N1—C101.328 (4)C18—H180.9300
N4—C131.303 (4)C18—C191.372 (6)
N4—C121.386 (3)C20—H200.9300
N7—C261.300 (4)C20—C191.396 (6)
N7—C271.449 (4)C19—H190.9300
N7—C281.442 (4)C27—H27A0.9600
N5—C221.372 (4)C27—H27B0.9600
N5—C141.319 (4)C27—H27C0.9600
O5—H5A0.8521C24—H24A0.9600
O5—H5B0.8497C24—H24B0.9600
N6—C231.298 (4)C24—H24C0.9600
N6—C241.425 (5)C28—H28A0.9600
N6—C251.451 (4)C28—H28B0.9600
C5—C61.449 (4)C28—H28C0.9600
C5—C41.404 (4)C25—H25A0.9600
C6—C71.405 (4)C25—H25B0.9600
C4—C31.406 (4)C25—H25C0.9600
C4—C121.437 (4)Cl3—O321.449 (3)
C1—H10.9300Cl3—O311.428 (2)
C1—C21.395 (4)Cl3—O331.430 (2)
C26—H260.9300Cl3—O341.427 (3)
C3—H30.9300Cl2—O61.452 (6)
C3—C21.373 (4)Cl2—O71.460 (6)
C11—C71.424 (4)Cl2—O81.410 (7)
C11—C121.366 (4)Cl2—O91.435 (7)
C23—H230.9300Cl1—O101.380 (13)
C22—C171.421 (4)Cl1—O111.358 (12)
C22—C211.407 (5)Cl1—O131.423 (11)
C7—C81.405 (4)Cl1—O121.365 (12)
O2—Cu1—O484.60 (9)C9—C8—C7118.8 (3)
O2—Cu1—N2168.83 (9)C9—C8—H8120.6
O2—Cu1—N193.56 (9)C14—C15—H15120.9
O2—Cu1—O3190.49 (8)C16—C15—H15120.9
O1—Cu1—O291.45 (8)C16—C15—C14118.2 (3)
O1—Cu1—O492.21 (8)N1—C10—H10118.9
O1—Cu1—N291.07 (9)N1—C10—C9122.2 (3)
O1—Cu1—N1168.47 (9)C9—C10—H10118.9
O1—Cu1—O3181.37 (8)C22—C17—C18118.3 (3)
O4—Cu1—O31171.83 (8)C16—C17—C22118.2 (3)
N2—Cu1—O4106.18 (9)C16—C17—C18123.5 (3)
N2—Cu1—O3179.14 (8)N5—C14—C13117.1 (3)
N1—Cu1—O498.60 (9)N5—C14—C15124.6 (3)
N1—Cu1—N282.09 (9)C15—C14—C13118.3 (3)
N1—Cu1—O3188.20 (8)C8—C9—C10120.1 (3)
C26—O2—Cu1125.1 (2)C8—C9—H9120.0
C23—O1—Cu1118.96 (19)C10—C9—H9120.0
C13—O3—C11103.7 (2)C15—C16—C17119.8 (3)
Cu1—O4—H4A112.6C15—C16—H16120.1
Cu1—O4—H4B111.5C17—C16—H16120.1
H4A—O4—H4B106.5C22—C21—H21119.6
C5—N2—Cu1112.50 (19)C20—C21—C22120.7 (3)
C1—N2—Cu1127.96 (19)C20—C21—H21119.6
C1—N2—C5118.4 (2)C17—C18—H18119.7
C6—N1—Cu1112.56 (18)C19—C18—C17120.5 (3)
C10—N1—Cu1128.20 (19)C19—C18—H18119.7
C10—N1—C6118.9 (2)C21—C20—H20119.7
C13—N4—C12104.1 (2)C21—C20—C19120.6 (3)
C26—N7—C27121.5 (3)C19—C20—H20119.7
C26—N7—C28121.5 (3)C18—C19—C20120.4 (3)
C28—N7—C27116.9 (3)C18—C19—H19119.8
C14—N5—C22117.3 (3)C20—C19—H19119.8
H5A—O5—H5B104.4N7—C27—H27A109.5
C23—N6—C24120.7 (3)N7—C27—H27B109.5
C23—N6—C25121.8 (3)N7—C27—H27C109.5
C24—N6—C25117.5 (3)H27A—C27—H27B109.5
N2—C5—C6115.5 (2)H27A—C27—H27C109.5
N2—C5—C4122.7 (3)H27B—C27—H27C109.5
C4—C5—C6121.8 (2)N6—C24—H24A109.5
N1—C6—C5116.0 (2)N6—C24—H24B109.5
N1—C6—C7121.9 (3)N6—C24—H24C109.5
C7—C6—C5122.1 (2)H24A—C24—H24B109.5
C5—C4—C3117.6 (2)H24A—C24—H24C109.5
C5—C4—C12115.4 (3)H24B—C24—H24C109.5
C3—C4—C12126.9 (3)N7—C28—H28A109.5
N2—C1—H1118.8N7—C28—H28B109.5
N2—C1—C2122.4 (3)N7—C28—H28C109.5
C2—C1—H1118.8H28A—C28—H28B109.5
O2—C26—N7123.6 (3)H28A—C28—H28C109.5
O2—C26—H26118.2H28B—C28—H28C109.5
N7—C26—H26118.2N6—C25—H25A109.5
C4—C3—H3120.5N6—C25—H25B109.5
C2—C3—C4119.1 (3)N6—C25—H25C109.5
C2—C3—H3120.5H25A—C25—H25B109.5
O3—C11—C7126.8 (3)H25A—C25—H25C109.5
C12—C11—O3108.1 (2)H25B—C25—H25C109.5
C12—C11—C7125.1 (2)O31—Cl3—O32108.18 (15)
O1—C23—N6123.9 (3)O31—Cl3—O33110.89 (15)
O1—C23—H23118.1O33—Cl3—O32110.35 (15)
N6—C23—H23118.1O34—Cl3—O32107.92 (18)
N5—C22—C17122.0 (3)O34—Cl3—O31109.61 (17)
N5—C22—C21118.7 (3)O34—Cl3—O33109.82 (16)
C21—C22—C17119.3 (3)Cl3—O31—Cu1133.25 (13)
C6—C7—C11114.0 (3)O6—Cl2—O7106.6 (5)
C6—C7—C8118.1 (3)O8—Cl2—O6117.4 (5)
C8—C7—C11127.9 (3)O8—Cl2—O7110.9 (5)
O3—C13—C14118.6 (3)O8—Cl2—O9109.2 (5)
N4—C13—O3115.2 (2)O9—Cl2—O6109.0 (5)
N4—C13—C14126.2 (3)O9—Cl2—O7102.7 (6)
N4—C12—C4129.5 (3)O10—Cl1—O13103.4 (10)
C11—C12—N4109.0 (2)O11—Cl1—O10122.3 (12)
C11—C12—C4121.5 (3)O11—Cl1—O13101.0 (11)
C1—C2—H2120.1O11—Cl1—O12118.5 (13)
C3—C2—C1119.8 (3)O12—Cl1—O10100.2 (10)
C3—C2—H2120.1O12—Cl1—O13110.5 (9)
C7—C8—H8120.6
Cu1—O2—C26—N7164.5 (2)C3—C4—C12—C11179.0 (3)
Cu1—O1—C23—N6166.9 (2)C11—O3—C13—N40.5 (3)
Cu1—N2—C5—C610.3 (3)C11—O3—C13—C14178.7 (2)
Cu1—N2—C5—C4167.4 (2)C11—C7—C8—C9176.7 (3)
Cu1—N2—C1—C2164.2 (2)C22—N5—C14—C13179.0 (2)
Cu1—N1—C6—C56.4 (3)C22—N5—C14—C150.3 (4)
Cu1—N1—C6—C7172.7 (2)C22—C17—C16—C150.2 (4)
Cu1—N1—C10—C9174.1 (2)C22—C17—C18—C190.6 (4)
O3—C11—C7—C6177.9 (3)C22—C21—C20—C191.3 (5)
O3—C11—C7—C80.7 (5)C7—C11—C12—N4178.0 (3)
O3—C11—C12—N40.3 (3)C7—C11—C12—C42.0 (4)
O3—C11—C12—C4179.6 (2)C7—C8—C9—C100.6 (5)
O3—C13—C14—N50.4 (4)C13—O3—C11—C7177.8 (3)
O3—C13—C14—C15179.2 (2)C13—O3—C11—C120.5 (3)
N2—C5—C6—N12.6 (4)C13—N4—C12—C4179.9 (3)
N2—C5—C6—C7178.3 (2)C13—N4—C12—C110.0 (3)
N2—C5—C4—C31.2 (4)C12—N4—C13—O30.3 (3)
N2—C5—C4—C12179.2 (2)C12—N4—C13—C14178.8 (3)
N2—C1—C2—C31.1 (4)C12—C4—C3—C2179.6 (3)
N1—C6—C7—C11175.9 (2)C12—C11—C7—C60.1 (4)
N1—C6—C7—C82.7 (4)C12—C11—C7—C8178.7 (3)
N1—C10—C9—C82.2 (5)C10—N1—C6—C5179.6 (3)
N4—C13—C14—N5178.7 (3)C10—N1—C6—C71.3 (4)
N4—C13—C14—C150.0 (4)C17—C22—C21—C200.4 (4)
N5—C22—C17—C160.7 (4)C17—C18—C19—C200.3 (5)
N5—C22—C17—C18179.1 (3)C14—N5—C22—C170.5 (4)
N5—C22—C21—C20179.9 (3)C14—N5—C22—C21179.8 (2)
C5—N2—C1—C22.6 (4)C14—C15—C16—C170.5 (4)
C5—C6—C7—C113.1 (4)C16—C15—C14—N50.8 (4)
C5—C6—C7—C8178.2 (3)C16—C15—C14—C13179.5 (3)
C5—C4—C3—C22.7 (4)C16—C17—C18—C19179.6 (3)
C5—C4—C12—N4178.9 (3)C21—C22—C17—C16179.6 (3)
C5—C4—C12—C111.2 (4)C21—C22—C17—C180.6 (4)
C6—N1—C10—C91.2 (4)C21—C20—C19—C181.3 (5)
C6—C5—C4—C3176.3 (2)C18—C17—C16—C15179.7 (3)
C6—C5—C4—C121.8 (4)C27—N7—C26—O2179.8 (3)
C6—C7—C8—C91.7 (4)C24—N6—C23—O10.4 (5)
C4—C5—C6—N1175.0 (2)C28—N7—C26—O20.9 (5)
C4—C5—C6—C74.1 (4)C25—N6—C23—O1178.9 (3)
C4—C3—C2—C11.6 (4)O32—Cl3—O31—Cu146.4 (2)
C1—N2—C5—C6179.0 (2)O33—Cl3—O31—Cu1167.57 (17)
C1—N2—C5—C41.4 (4)O34—Cl3—O31—Cu171.0 (2)
C3—C4—C12—N41.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O50.911.942.808 (3)160
O4—H4B···O32i0.911.962.782 (3)151
O5—H5A···O11ii0.852.022.862 (18)170
O5—H5B···O100.851.952.790 (13)171
O5—H5A···O7ii0.852.112.954 (7)174
O5—H5B···O60.852.072.905 (7)165
Symmetry codes: (i) x, y1, z; (ii) x+3/2, y+1/2, z+1.
 

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