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The title compound, [Cu2Cl2(C15H17N3O2)2](ClO4)2·H2O, contains dichloro-bridged CuII complexes located on centres of inversion. The solvent water mol­ecule lies on a twofold rotation axis and forms hydrogen bonds to two perchlorate anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034908/hy2022sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034908/hy2022Isup2.hkl
Contains datablock I

CCDC reference: 624736

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.048
  • wR factor = 0.116
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. turquoise CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.42 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Di-µ-chloro-bis({methyl [N,N-bis(2-pyridylmethyl)amino]acetate- κ4N,N',N'',O}copper(II)) diperchlorate monohydrate top
Crystal data top
[Cu2Cl2(C15H17N3O2)2](ClO4)2·H2OF(000) = 1952
Mr = 957.53Dx = 1.718 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6163 reflections
a = 19.1398 (7) Åθ = 2.6–25.4°
b = 8.5993 (3) ŵ = 1.51 mm1
c = 24.1605 (8) ÅT = 180 K
β = 111.380 (1)°Block, turquoise
V = 3702.9 (2) Å30.25 × 0.08 × 0.08 mm
Z = 4
Data collection top
Bruker–Nonius X8-APEX-II CCD
diffractometer
4535 independent reflections
Radiation source: fine-focus sealed tube3461 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
thin–slice ω and φ scansθmax = 28.3°, θmin = 3.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1925
Tmin = 0.735, Tmax = 0.889k = 1111
36620 measured reflectionsl = 3226
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0354P)2 + 16.3749P]
where P = (Fo2 + 2Fc2)/3
4535 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 1.18 e Å3
12 restraintsΔρmin = 0.49 e Å3
Special details top

Experimental. largest difference peak associated with perchlorate anion.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.34697 (2)0.21148 (5)0.052165 (16)0.02776 (13)
Cl10.29214 (5)0.12462 (10)0.04197 (3)0.0308 (2)
O10.47109 (14)0.1136 (3)0.07548 (11)0.0420 (7)
O20.57392 (14)0.0931 (3)0.15818 (12)0.0433 (7)
N10.38417 (15)0.4146 (3)0.03426 (12)0.0292 (6)
N20.39628 (16)0.2857 (4)0.13926 (12)0.0309 (6)
N30.31469 (15)0.0355 (3)0.09138 (12)0.0290 (6)
C10.38850 (19)0.4600 (4)0.01758 (15)0.0316 (8)
H1A0.37150.39140.05060.038*
C20.4168 (2)0.6031 (5)0.02441 (18)0.0381 (9)
H2A0.41840.63330.06180.046*
C30.4429 (2)0.7015 (5)0.02385 (19)0.0438 (9)
H3A0.46280.80050.02010.053*
C40.4400 (2)0.6554 (5)0.07759 (18)0.0428 (9)
H4A0.45840.72120.11140.051*
C50.40974 (19)0.5116 (4)0.08128 (15)0.0327 (8)
C60.3991 (2)0.4574 (4)0.13694 (16)0.0387 (9)
H6A0.44110.49600.17210.046*
H6B0.35190.50120.13820.046*
C70.3450 (2)0.2282 (5)0.16864 (15)0.0376 (9)
H7A0.37140.22870.21230.045*
H7B0.30080.29740.15870.045*
C80.32043 (19)0.0675 (5)0.14789 (15)0.0334 (8)
C90.3003 (2)0.0413 (5)0.18131 (16)0.0431 (10)
H9A0.30520.01820.22100.052*
C100.2731 (2)0.1834 (5)0.15684 (18)0.0464 (10)
H10A0.25830.25840.17930.056*
C110.2675 (2)0.2164 (5)0.09936 (17)0.0406 (9)
H11A0.24900.31410.08170.049*
C120.2894 (2)0.1040 (4)0.06837 (16)0.0359 (8)
H12A0.28640.12660.02910.043*
C130.4717 (2)0.2143 (5)0.16873 (16)0.0393 (9)
H13A0.46830.13610.19770.047*
H13B0.50690.29630.19130.047*
C140.5041 (2)0.1374 (5)0.12790 (16)0.0359 (8)
C150.6128 (2)0.0103 (6)0.1241 (2)0.0530 (11)
H15A0.66420.01460.15050.079*
H15B0.61430.07670.09160.079*
H15C0.58590.08600.10780.079*
Cl20.63019 (5)0.56644 (12)0.20820 (4)0.0400 (2)
O2A0.5727 (2)0.6096 (8)0.22630 (19)0.140 (3)
O2B0.6611 (4)0.6883 (6)0.1886 (3)0.161 (3)
O2C0.6033 (2)0.4633 (7)0.1608 (2)0.131 (2)
O2D0.69066 (19)0.5047 (5)0.25644 (14)0.0698 (10)
O1W0.50000.8911 (6)0.25000.104 (2)
H1W0.529 (3)0.834 (2)0.240 (4)0.156*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0285 (2)0.0337 (2)0.01847 (19)0.00244 (18)0.00544 (15)0.00104 (17)
Cl10.0329 (4)0.0368 (5)0.0213 (4)0.0014 (4)0.0081 (3)0.0041 (3)
O10.0367 (14)0.0550 (18)0.0315 (14)0.0112 (13)0.0092 (11)0.0021 (12)
O20.0302 (14)0.0528 (17)0.0411 (14)0.0081 (13)0.0060 (11)0.0030 (13)
N10.0231 (14)0.0333 (16)0.0286 (14)0.0048 (12)0.0062 (11)0.0003 (12)
N20.0285 (14)0.0387 (17)0.0222 (13)0.0056 (13)0.0051 (11)0.0035 (13)
N30.0264 (14)0.0350 (17)0.0239 (13)0.0068 (12)0.0071 (11)0.0018 (12)
C10.0274 (17)0.037 (2)0.0287 (17)0.0063 (15)0.0083 (14)0.0003 (15)
C20.0318 (19)0.040 (2)0.043 (2)0.0037 (17)0.0138 (16)0.0088 (17)
C30.035 (2)0.035 (2)0.058 (3)0.0010 (17)0.0135 (18)0.0038 (19)
C40.035 (2)0.042 (2)0.045 (2)0.0006 (18)0.0076 (17)0.0094 (18)
C50.0245 (17)0.037 (2)0.0320 (18)0.0035 (15)0.0041 (14)0.0048 (15)
C60.044 (2)0.039 (2)0.0285 (18)0.0042 (17)0.0076 (16)0.0088 (16)
C70.0352 (19)0.057 (2)0.0205 (15)0.0055 (18)0.0098 (14)0.0040 (16)
C80.0246 (17)0.051 (2)0.0238 (16)0.0111 (16)0.0076 (13)0.0045 (16)
C90.033 (2)0.067 (3)0.0295 (18)0.0053 (19)0.0122 (16)0.0088 (19)
C100.036 (2)0.059 (3)0.043 (2)0.003 (2)0.0125 (18)0.019 (2)
C110.036 (2)0.039 (2)0.042 (2)0.0029 (17)0.0087 (17)0.0097 (18)
C120.0323 (19)0.040 (2)0.0331 (18)0.0062 (16)0.0091 (15)0.0032 (16)
C130.0302 (18)0.055 (2)0.0268 (17)0.0025 (18)0.0038 (14)0.0028 (17)
C140.0321 (19)0.039 (2)0.036 (2)0.0049 (16)0.0112 (16)0.0047 (17)
C150.042 (2)0.064 (3)0.057 (3)0.014 (2)0.023 (2)0.013 (2)
Cl20.0399 (5)0.0457 (5)0.0325 (4)0.0025 (4)0.0111 (4)0.0039 (4)
O2A0.057 (2)0.277 (8)0.077 (3)0.049 (4)0.014 (2)0.065 (4)
O2B0.188 (6)0.101 (4)0.199 (7)0.001 (4)0.076 (5)0.094 (4)
O2C0.077 (3)0.189 (6)0.113 (4)0.003 (3)0.017 (3)0.109 (4)
O2D0.068 (2)0.092 (3)0.0477 (18)0.025 (2)0.0186 (16)0.0203 (18)
O1W0.071 (4)0.053 (3)0.201 (8)0.0000.065 (5)0.000
Geometric parameters (Å, º) top
Cu1—N11.992 (3)C6—H6A0.990
Cu1—N22.068 (3)C6—H6B0.990
Cu1—N31.999 (3)C7—C81.487 (6)
Cu1—O12.386 (3)C7—H7A0.990
Cu1—Cl12.2564 (8)C7—H7B0.990
Cu1—Cl1i2.9424 (9)C8—C91.380 (5)
O1—C141.209 (4)C9—C101.374 (6)
O2—C141.325 (4)C9—H9A0.950
O2—C151.478 (5)C10—C111.383 (6)
N1—C11.343 (4)C10—H10A0.950
N1—C51.350 (4)C11—C121.378 (5)
N2—C61.479 (5)C11—H11A0.950
N2—C71.489 (5)C12—H12A0.950
N2—C131.490 (4)C13—C141.496 (5)
N3—C121.337 (5)C13—H13A0.990
N3—C81.357 (4)C13—H13B0.990
C1—C21.378 (5)C15—H15A0.980
C1—H1A0.950C15—H15B0.980
C2—C31.379 (6)C15—H15C0.980
C2—H2A0.950Cl2—O2B1.370 (4)
C3—C41.379 (6)Cl2—O2A1.375 (4)
C3—H3A0.950Cl2—O2C1.390 (4)
C4—C51.382 (6)Cl2—O2D1.413 (3)
C4—H4A0.950O1W—H1W0.84 (6)
C5—C61.506 (5)
N1—Cu1—N283.32 (12)C5—C6—H6A109.4
N1—Cu1—N3164.41 (11)N2—C6—H6B109.4
N2—Cu1—N381.76 (12)C5—C6—H6B109.4
N1—Cu1—Cl198.23 (8)H6A—C6—H6B108.0
N2—Cu1—Cl1178.45 (9)C8—C7—N2109.3 (3)
N3—Cu1—Cl196.70 (8)C8—C7—H7A109.8
N1—Cu1—O187.51 (11)N2—C7—H7A109.8
N2—Cu1—O179.80 (10)C8—C7—H7B109.8
N3—Cu1—O194.26 (10)N2—C7—H7B109.8
Cl1—Cu1—O1100.28 (7)H7A—C7—H7B108.3
N1—Cu1—Cl1i86.91 (8)N3—C8—C9120.9 (4)
N2—Cu1—Cl1i90.04 (8)N3—C8—C7115.3 (3)
N3—Cu1—Cl1i88.60 (8)C9—C8—C7123.7 (3)
Cl1—Cu1—Cl1i90.00 (3)C10—C9—C8119.6 (4)
O1—Cu1—Cl1i168.91 (7)C10—C9—H9A120.2
C14—O1—Cu1106.4 (2)C8—C9—H9A120.2
C14—O2—C15116.3 (3)C9—C10—C11119.6 (4)
C1—N1—C5118.6 (3)C9—C10—H10A120.2
C1—N1—Cu1127.3 (2)C11—C10—H10A120.2
C5—N1—Cu1114.1 (2)C12—C11—C10118.3 (4)
C6—N2—C7112.9 (3)C12—C11—H11A120.9
C6—N2—C13112.8 (3)C10—C11—H11A120.9
C7—N2—C13109.1 (3)N3—C12—C11122.6 (3)
C6—N2—Cu1106.2 (2)N3—C12—H12A118.7
C7—N2—Cu1104.3 (2)C11—C12—H12A118.7
C13—N2—Cu1111.2 (2)N2—C13—C14115.4 (3)
C12—N3—C8119.0 (3)N2—C13—H13A108.4
C12—N3—Cu1127.6 (2)C14—C13—H13A108.4
C8—N3—Cu1113.5 (2)N2—C13—H13B108.4
N1—C1—C2122.2 (3)C14—C13—H13B108.4
N1—C1—H1A118.9H13A—C13—H13B107.5
C2—C1—H1A118.9O1—C14—O2124.5 (4)
C1—C2—C3118.9 (4)O1—C14—C13125.6 (3)
C1—C2—H2A120.5O2—C14—C13109.9 (3)
C3—C2—H2A120.5O2—C15—H15A109.5
C4—C3—C2119.5 (4)O2—C15—H15B109.5
C4—C3—H3A120.2H15A—C15—H15B109.5
C2—C3—H3A120.2O2—C15—H15C109.5
C3—C4—C5118.7 (4)H15A—C15—H15C109.5
C3—C4—H4A120.6H15B—C15—H15C109.5
C5—C4—H4A120.6O2B—Cl2—O2A113.5 (4)
N1—C5—C4122.1 (3)O2B—Cl2—O2C106.2 (4)
N1—C5—C6115.8 (3)O2A—Cl2—O2C109.6 (3)
C4—C5—C6122.1 (3)O2B—Cl2—O2D104.2 (3)
N2—C6—C5111.2 (3)O2A—Cl2—O2D110.4 (2)
N2—C6—H6A109.4O2C—Cl2—O2D112.7 (3)
N1—Cu1—O1—C1490.0 (3)N1—C1—C2—C31.3 (5)
N3—Cu1—O1—C1474.5 (3)C1—C2—C3—C40.2 (6)
N2—Cu1—O1—C146.3 (3)C2—C3—C4—C50.9 (6)
Cl1—Cu1—O1—C14172.1 (3)C1—N1—C5—C40.0 (5)
Cl1i—Cu1—O1—C1430.2 (5)Cu1—N1—C5—C4177.8 (3)
N3—Cu1—N1—C1176.3 (4)C1—N1—C5—C6176.6 (3)
N2—Cu1—N1—C1166.7 (3)Cu1—N1—C5—C65.6 (4)
Cl1—Cu1—N1—C113.3 (3)C3—C4—C5—N11.0 (6)
O1—Cu1—N1—C186.7 (3)C3—C4—C5—C6175.4 (3)
Cl1i—Cu1—N1—C1102.9 (3)C7—N2—C6—C5146.3 (3)
N3—Cu1—N1—C56.1 (5)C13—N2—C6—C589.4 (3)
N2—Cu1—N1—C510.8 (2)Cu1—N2—C6—C532.6 (3)
Cl1—Cu1—N1—C5169.2 (2)N1—C5—C6—N226.7 (4)
O1—Cu1—N1—C590.8 (2)C4—C5—C6—N2156.7 (3)
Cl1i—Cu1—N1—C579.6 (2)C6—N2—C7—C8156.6 (3)
N1—Cu1—N2—C623.9 (2)C13—N2—C7—C877.2 (3)
N3—Cu1—N2—C6151.5 (2)Cu1—N2—C7—C841.7 (3)
O1—Cu1—N2—C6112.6 (2)C12—N3—C8—C90.3 (5)
Cl1i—Cu1—N2—C662.9 (2)Cu1—N3—C8—C9179.9 (3)
N1—Cu1—N2—C7143.4 (2)C12—N3—C8—C7176.8 (3)
N3—Cu1—N2—C732.1 (2)Cu1—N3—C8—C73.4 (4)
O1—Cu1—N2—C7127.9 (2)N2—C7—C8—N331.5 (4)
Cl1i—Cu1—N2—C756.5 (2)N2—C7—C8—C9152.1 (3)
N1—Cu1—N2—C1399.1 (3)N3—C8—C9—C100.9 (5)
N3—Cu1—N2—C1385.4 (3)C7—C8—C9—C10175.3 (3)
O1—Cu1—N2—C1310.4 (2)C8—C9—C10—C111.1 (6)
Cl1i—Cu1—N2—C13174.0 (2)C9—C10—C11—C120.2 (6)
N1—Cu1—N3—C12179.8 (4)C8—N3—C12—C111.2 (5)
N2—Cu1—N3—C12162.8 (3)Cu1—N3—C12—C11179.0 (3)
Cl1—Cu1—N3—C1217.1 (3)C10—C11—C12—N31.0 (6)
O1—Cu1—N3—C1283.8 (3)C6—N2—C13—C14105.3 (4)
Cl1i—Cu1—N3—C12106.9 (3)C7—N2—C13—C14128.4 (4)
N1—Cu1—N3—C80.0 (5)Cu1—N2—C13—C1413.9 (4)
N2—Cu1—N3—C817.0 (2)Cu1—O1—C14—O2176.9 (3)
Cl1—Cu1—N3—C8163.1 (2)Cu1—O1—C14—C130.3 (5)
O1—Cu1—N3—C896.0 (2)C15—O2—C14—O10.6 (6)
Cl1i—Cu1—N3—C873.3 (2)C15—O2—C14—C13178.1 (3)
C5—N1—C1—C21.2 (5)N2—C13—C14—O19.1 (6)
Cu1—N1—C1—C2178.6 (2)N2—C13—C14—O2173.5 (3)
Symmetry code: (i) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O2A0.84 (6)2.18 (2)2.951 (7)153 (2)
 

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