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The title compound, [Cu(C10H28N4)(ClO4)]ClO4, is formed by the reaction of bis­(propane-1,3-diamine)copper(II) perchlorate with acetone. It has copper(II) ions coordinated by two bidentate ligands, N-(isopropyl­idene)propane-1,3-diamine, with N-isopropyl­idine imine and primary amine donor groups, the former resulting from the combination of the amine with acetone. The N4 group is tetra­hedrally twisted [r.m.s. displacement of N atoms from the N4 plane = 0.252 (1) Å], with the Cu displaced from the plane by 0.113 (1) Å, towards an O atom of an axially coordinated perchlorate ion [mean Cu—Namine = 2.029 (3) Å, mean Cu—Nimine = 1.993 (3) Å and Cu—O = 2.474 (2) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605046X/sj2178sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680605046X/sj2178Isup2.hkl
Contains datablock I

CCDC reference: 630485

Key indicators

  • Single-crystal X-ray study
  • T = 106 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.109
  • Data-to-parameter ratio = 27.2

checkCIF/PLATON results

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Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR) is > 1.50 Tmin and Tmax reported: 0.675 0.945 Tmin and Tmax expected: 0.440 0.945 RR = 1.535 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_B Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.56
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 9.99 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cl1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3.2 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Bis[N-(isopropylidene)propane-1,3-diamine-κ2N](perchlorato-κO)copper(II) perchlorate top
Crystal data top
[Cu(C12H28N4)(ClO4)]ClO4F(000) = 1020
Mr = 490.82Dx = 1.633 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7934 reflections
a = 11.1939 (4) Åθ = 2.3–32.6°
b = 14.8324 (5) ŵ = 1.41 mm1
c = 12.4020 (4) ÅT = 106 K
β = 104.241 (2)°Plate, blue
V = 1995.86 (12) Å30.7 × 0.5 × 0.04 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6737 independent reflections
Radiation source: sealed tube5036 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 32.9°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1616
Tmin = 0.675, Tmax = 0.945k = 2121
23993 measured reflectionsl = 1418
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0591P)2 + 0.52P]
where P = (Fo2 + 2Fc2)/3
6737 reflections(Δ/σ)max = 0.008
248 parametersΔρmax = 1.04 e Å3
0 restraintsΔρmin = 0.74 e Å3
Special details top

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
Cu10.26199 (2)0.959441 (15)0.717672 (19)0.01365 (7)
N10.19813 (17)0.88825 (11)0.57599 (14)0.0195 (3)
H1A0.19940.82950.59450.023*
H1B0.11870.90360.54840.023*
C10.2623 (2)0.89748 (14)0.48445 (17)0.0236 (4)
H1C0.25140.95850.45550.028*
H1D0.22470.85670.42450.028*
C20.3987 (2)0.87708 (14)0.52233 (18)0.0247 (5)
H2A0.43480.88250.45910.030*
H2B0.40910.81510.54790.030*
C30.4689 (2)0.93860 (14)0.61528 (19)0.0226 (4)
H3A0.55700.92960.62670.027*
H3B0.45041.00120.59550.027*
N40.43053 (16)0.91626 (11)0.71833 (14)0.0168 (3)
C50.4950 (2)0.86347 (13)0.79079 (18)0.0208 (4)
C60.4472 (2)0.83346 (17)0.88707 (19)0.0309 (5)
H6A0.36760.85990.88180.046*
H6B0.50300.85220.95520.046*
H6C0.44000.76890.88620.046*
C70.6181 (2)0.82532 (17)0.7881 (2)0.0335 (5)
H7A0.62120.81560.71230.050*
H7B0.63030.76900.82750.050*
H7C0.68180.86690.82270.050*
N110.32907 (16)1.04547 (11)0.84582 (15)0.0185 (3)
H11A0.33931.01400.90950.022*
H11B0.40441.06340.84090.022*
C110.2566 (2)1.12752 (14)0.85596 (18)0.0226 (4)
H11C0.25191.16570.79160.027*
H11D0.29861.16110.92150.027*
C120.1278 (2)1.10478 (14)0.86457 (18)0.0236 (4)
H12A0.08611.16000.87600.028*
H12B0.13301.06670.92910.028*
C130.0510 (2)1.05675 (13)0.76185 (17)0.0203 (4)
H13A0.03431.05380.76580.024*
H13B0.05461.09010.69540.024*
N140.09930 (16)0.96511 (11)0.75616 (14)0.0174 (3)
C150.0463 (2)0.89864 (15)0.79150 (18)0.0231 (4)
C160.0947 (3)0.80514 (16)0.7912 (2)0.0337 (5)
H16A0.03630.76910.73920.051*
H16B0.10740.77970.86430.051*
H16C0.17150.80640.76980.051*
C170.0684 (3)0.9076 (2)0.8327 (3)0.0415 (7)
H17A0.05630.95310.88940.062*
H17B0.08610.85100.86300.062*
H17C0.13610.92430.77210.062*
Cl10.17711 (5)1.13738 (3)0.51314 (4)0.01803 (10)
O10.26535 (15)1.09734 (10)0.60624 (13)0.0239 (3)
O20.12422 (18)1.21589 (11)0.54948 (16)0.0371 (4)
O30.08124 (16)1.07210 (12)0.47173 (16)0.0350 (4)
O40.2376 (2)1.15984 (13)0.42804 (16)0.0428 (5)
Cl20.31994 (5)0.61215 (3)0.64111 (4)0.02097 (11)
O50.3302 (2)0.53490 (12)0.57478 (16)0.0465 (6)
O60.43967 (17)0.65279 (14)0.67678 (19)0.0448 (5)
O70.2775 (2)0.58431 (17)0.73444 (16)0.0492 (6)
O80.2382 (2)0.67650 (14)0.5758 (2)0.0562 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01604 (12)0.01581 (11)0.01054 (11)0.00063 (8)0.00604 (8)0.00088 (8)
N10.0231 (9)0.0220 (8)0.0147 (8)0.0018 (7)0.0069 (7)0.0026 (6)
C10.0400 (13)0.0202 (9)0.0138 (9)0.0016 (8)0.0126 (9)0.0019 (7)
C20.0409 (13)0.0192 (9)0.0213 (10)0.0003 (8)0.0219 (10)0.0004 (8)
C30.0252 (11)0.0229 (9)0.0248 (11)0.0002 (8)0.0160 (9)0.0026 (8)
N40.0184 (8)0.0179 (7)0.0165 (8)0.0004 (6)0.0088 (6)0.0006 (6)
C50.0210 (10)0.0214 (9)0.0206 (10)0.0022 (8)0.0062 (8)0.0036 (7)
C60.0365 (13)0.0393 (12)0.0175 (10)0.0141 (10)0.0079 (10)0.0080 (9)
C70.0236 (12)0.0371 (12)0.0397 (15)0.0104 (10)0.0075 (10)0.0017 (11)
N110.0186 (8)0.0212 (8)0.0158 (8)0.0006 (6)0.0045 (6)0.0025 (6)
C110.0279 (11)0.0185 (9)0.0201 (10)0.0011 (8)0.0033 (9)0.0045 (7)
C120.0294 (12)0.0260 (10)0.0173 (10)0.0066 (8)0.0093 (9)0.0031 (8)
C130.0226 (10)0.0224 (9)0.0172 (9)0.0044 (7)0.0075 (8)0.0031 (7)
N140.0187 (8)0.0194 (7)0.0159 (8)0.0004 (6)0.0079 (6)0.0012 (6)
C150.0241 (11)0.0279 (10)0.0178 (10)0.0033 (8)0.0060 (8)0.0012 (8)
C160.0412 (15)0.0256 (11)0.0351 (14)0.0047 (10)0.0107 (11)0.0051 (10)
C170.0360 (15)0.0472 (15)0.0483 (17)0.0052 (12)0.0240 (13)0.0094 (13)
Cl10.0233 (2)0.0177 (2)0.0139 (2)0.00104 (17)0.00612 (18)0.00234 (15)
O10.0259 (8)0.0245 (7)0.0186 (7)0.0021 (6)0.0003 (6)0.0026 (6)
O20.0478 (11)0.0270 (8)0.0364 (10)0.0153 (8)0.0105 (9)0.0034 (7)
O30.0267 (9)0.0322 (9)0.0402 (11)0.0059 (7)0.0031 (8)0.0028 (8)
O40.0575 (13)0.0488 (11)0.0318 (10)0.0014 (9)0.0296 (10)0.0149 (8)
Cl20.0246 (2)0.0230 (2)0.0169 (2)0.00084 (18)0.00805 (19)0.00162 (17)
O50.0877 (17)0.0300 (9)0.0284 (10)0.0051 (9)0.0266 (11)0.0100 (7)
O60.0249 (9)0.0470 (11)0.0631 (14)0.0088 (8)0.0121 (9)0.0081 (10)
O70.0591 (14)0.0700 (14)0.0280 (10)0.0192 (11)0.0286 (10)0.0039 (10)
O80.0479 (13)0.0421 (11)0.0681 (16)0.0106 (10)0.0060 (12)0.0142 (11)
Geometric parameters (Å, º) top
Cu1—N41.991 (2)N11—H11B0.9000
Cu1—N141.995 (2)C11—C121.511 (3)
Cu1—N12.024 (2)C11—H11C0.9700
Cu1—N112.033 (2)C11—H11D0.9700
Cu1—O12.474 (2)C12—C131.526 (3)
N1—C11.492 (3)C12—H12A0.9700
N1—H1A0.9000C12—H12B0.9700
N1—H1B0.9000C13—N141.471 (2)
C1—C21.514 (3)C13—H13A0.9700
C1—H1C0.9700C13—H13B0.9700
C1—H1D0.9700N14—C151.282 (3)
C2—C31.527 (3)C15—C161.489 (3)
C2—H2A0.9700C15—C171.500 (3)
C2—H2B0.9700C16—H16A0.9600
C3—N41.483 (3)C16—H16B0.9600
C3—H3A0.9700C16—H16C0.9600
C3—H3B0.9700C17—H17A0.9600
N4—C51.274 (3)C17—H17B0.9600
C5—C61.492 (3)C17—H17C0.9600
C5—C71.497 (3)Cl1—O41.4265 (17)
C6—H6A0.9600Cl1—O21.4286 (16)
C6—H6B0.9600Cl1—O31.4428 (18)
C6—H6C0.9600Cl1—O11.4493 (16)
C7—H7A0.9600Cl2—O71.4167 (18)
C7—H7B0.9600Cl2—O81.428 (2)
C7—H7C0.9600Cl2—O51.4315 (17)
N11—C111.485 (3)Cl2—O61.4365 (19)
N11—H11A0.9000
N4—Cu1—N14158.87 (7)Cu1—N11—H11A107.7
N4—Cu1—N188.15 (7)C11—N11—H11B107.7
N14—Cu1—N194.68 (7)Cu1—N11—H11B107.7
N4—Cu1—N1191.79 (7)H11A—N11—H11B107.1
N14—Cu1—N1188.27 (7)N11—C11—C12111.95 (17)
N1—Cu1—N11171.96 (7)N11—C11—H11C109.2
N4—Cu1—O197.11 (6)C12—C11—H11C109.2
N14—Cu1—O1103.83 (6)N11—C11—H11D109.2
N1—Cu1—O189.83 (6)C12—C11—H11D109.2
N11—Cu1—O182.20 (6)H11C—C11—H11D107.9
C1—N1—Cu1118.66 (13)C11—C12—C13113.34 (17)
C1—N1—H1A107.6C11—C12—H12A108.9
Cu1—N1—H1A107.6C13—C12—H12A108.9
C1—N1—H1B107.6C11—C12—H12B108.9
Cu1—N1—H1B107.6C13—C12—H12B108.9
H1A—N1—H1B107.1H12A—C12—H12B107.7
N1—C1—C2112.54 (17)N14—C13—C12109.48 (17)
N1—C1—H1C109.1N14—C13—H13A109.8
C2—C1—H1C109.1C12—C13—H13A109.8
N1—C1—H1D109.1N14—C13—H13B109.8
C2—C1—H1D109.1C12—C13—H13B109.8
H1C—C1—H1D107.8H13A—C13—H13B108.2
C1—C2—C3114.02 (17)C15—N14—C13119.22 (18)
C1—C2—H2A108.7C15—N14—Cu1125.15 (15)
C3—C2—H2A108.7C13—N14—Cu1114.72 (12)
C1—C2—H2B108.7N14—C15—C16121.1 (2)
C3—C2—H2B108.7N14—C15—C17123.7 (2)
H2A—C2—H2B107.6C16—C15—C17115.2 (2)
N4—C3—C2108.22 (16)C15—C16—H16A109.5
N4—C3—H3A110.1C15—C16—H16B109.5
C2—C3—H3A110.1H16A—C16—H16B109.5
N4—C3—H3B110.1C15—C16—H16C109.5
C2—C3—H3B110.1H16A—C16—H16C109.5
H3A—C3—H3B108.4H16B—C16—H16C109.5
C5—N4—C3120.75 (18)C15—C17—H17A109.5
C5—N4—Cu1124.95 (14)C15—C17—H17B109.5
C3—N4—Cu1113.57 (13)H17A—C17—H17B109.5
N4—C5—C6119.67 (19)C15—C17—H17C109.5
N4—C5—C7125.5 (2)H17A—C17—H17C109.5
C6—C5—C7114.8 (2)H17B—C17—H17C109.5
C5—C6—H6A109.5O4—Cl1—O2110.61 (12)
C5—C6—H6B109.5O4—Cl1—O3109.89 (12)
H6A—C6—H6B109.5O2—Cl1—O3109.24 (12)
C5—C6—H6C109.5O4—Cl1—O1109.31 (11)
H6A—C6—H6C109.5O2—Cl1—O1109.68 (10)
H6B—C6—H6C109.5O3—Cl1—O1108.07 (10)
C5—C7—H7A109.5Cl1—O1—Cu1133.06 (9)
C5—C7—H7B109.5O7—Cl2—O8111.18 (15)
H7A—C7—H7B109.5O7—Cl2—O5109.07 (13)
C5—C7—H7C109.5O8—Cl2—O5109.86 (14)
H7A—C7—H7C109.5O7—Cl2—O6110.24 (13)
H7B—C7—H7C109.5O8—Cl2—O6108.26 (13)
C11—N11—Cu1118.45 (13)O5—Cl2—O6108.18 (14)
C11—N11—H11A107.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O80.902.333.173 (3)155
N1—H1B···O3i0.902.223.093 (3)163
N11—H11A···O5ii0.902.203.077 (2)165
N11—H11B···O6iii0.902.253.110 (3)161
Symmetry codes: (i) x, y+2, z+1; (ii) x, y+3/2, z+1/2; (iii) x+1, y+1/2, z+3/2.
 

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