Bis[N-(isopropyl­idene)propane-1,3-diamine-κ²N](perchlorato-κO)copper(II) perchlorate

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—N_amine = 2.029 (3) Å, mean Cu—N_imine = 1.993 (3) Å and Cu—O = 2.474 (2) Å].

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

No syntax errors found



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

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Computing details

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

Crystal data

[Cu(C12H28N4)(ClO4)]ClO4	F(000) = 1020
Mr = 490.82	Dx = 1.633 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7934 reflections
a = 11.1939 (4) Å	θ = 2.3–32.6°
b = 14.8324 (5) Å	µ = 1.41 mm^−1
c = 12.4020 (4) Å	T = 106 K
β = 104.241 (2)°	Plate, blue
V = 1995.86 (12) Å^3	0.7 × 0.5 × 0.04 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	6737 independent reflections
Radiation source: sealed tube	5036 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 32.9°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −16→16
Tmin = 0.675, Tmax = 0.945	k = −21→21
23993 measured reflections	l = −14→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.52P] where P = (Fo^2 + 2Fc^2)/3
6737 reflections	(Δ/σ)max = 0.008
248 parameters	Δρmax = 1.04 e Å^−3
0 restraints	Δρmin = −0.74 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.26199 (2)	0.959441 (15)	0.717672 (19)	0.01365 (7)
N1	0.19813 (17)	0.88825 (11)	0.57599 (14)	0.0195 (3)
H1A	0.1994	0.8295	0.5945	0.023*
H1B	0.1187	0.9036	0.5484	0.023*
C1	0.2623 (2)	0.89748 (14)	0.48445 (17)	0.0236 (4)
H1C	0.2514	0.9585	0.4555	0.028*
H1D	0.2247	0.8567	0.4245	0.028*
C2	0.3987 (2)	0.87708 (14)	0.52233 (18)	0.0247 (5)
H2A	0.4348	0.8825	0.4591	0.030*
H2B	0.4091	0.8151	0.5479	0.030*
C3	0.4689 (2)	0.93860 (14)	0.61528 (19)	0.0226 (4)
H3A	0.5570	0.9296	0.6267	0.027*
H3B	0.4504	1.0012	0.5955	0.027*
N4	0.43053 (16)	0.91626 (11)	0.71833 (14)	0.0168 (3)
C5	0.4950 (2)	0.86347 (13)	0.79079 (18)	0.0208 (4)
C6	0.4472 (2)	0.83346 (17)	0.88707 (19)	0.0309 (5)
H6A	0.3676	0.8599	0.8818	0.046*
H6B	0.5030	0.8522	0.9552	0.046*
H6C	0.4400	0.7689	0.8862	0.046*
C7	0.6181 (2)	0.82532 (17)	0.7881 (2)	0.0335 (5)
H7A	0.6212	0.8156	0.7123	0.050*
H7B	0.6303	0.7690	0.8275	0.050*
H7C	0.6818	0.8669	0.8227	0.050*
N11	0.32907 (16)	1.04547 (11)	0.84582 (15)	0.0185 (3)
H11A	0.3393	1.0140	0.9095	0.022*
H11B	0.4044	1.0634	0.8409	0.022*
C11	0.2566 (2)	1.12752 (14)	0.85596 (18)	0.0226 (4)
H11C	0.2519	1.1657	0.7916	0.027*
H11D	0.2986	1.1611	0.9215	0.027*
C12	0.1278 (2)	1.10478 (14)	0.86457 (18)	0.0236 (4)
H12A	0.0861	1.1600	0.8760	0.028*
H12B	0.1330	1.0667	0.9291	0.028*
C13	0.0510 (2)	1.05675 (13)	0.76185 (17)	0.0203 (4)
H13A	−0.0343	1.0538	0.7658	0.024*
H13B	0.0546	1.0901	0.6954	0.024*
N14	0.09930 (16)	0.96511 (11)	0.75616 (14)	0.0174 (3)
C15	0.0463 (2)	0.89864 (15)	0.79150 (18)	0.0231 (4)
C16	0.0947 (3)	0.80514 (16)	0.7912 (2)	0.0337 (5)
H16A	0.0363	0.7691	0.7392	0.051*
H16B	0.1074	0.7797	0.8643	0.051*
H16C	0.1715	0.8064	0.7698	0.051*
C17	−0.0684 (3)	0.9076 (2)	0.8327 (3)	0.0415 (7)
H17A	−0.0563	0.9531	0.8894	0.062*
H17B	−0.0861	0.8510	0.8630	0.062*
H17C	−0.1361	0.9243	0.7721	0.062*
Cl1	0.17711 (5)	1.13738 (3)	0.51314 (4)	0.01803 (10)
O1	0.26535 (15)	1.09734 (10)	0.60624 (13)	0.0239 (3)
O2	0.12422 (18)	1.21589 (11)	0.54948 (16)	0.0371 (4)
O3	0.08124 (16)	1.07210 (12)	0.47173 (16)	0.0350 (4)
O4	0.2376 (2)	1.15984 (13)	0.42804 (16)	0.0428 (5)
Cl2	0.31994 (5)	0.61215 (3)	0.64111 (4)	0.02097 (11)
O5	0.3302 (2)	0.53490 (12)	0.57478 (16)	0.0465 (6)
O6	0.43967 (17)	0.65279 (14)	0.67678 (19)	0.0448 (5)
O7	0.2775 (2)	0.58431 (17)	0.73444 (16)	0.0492 (6)
O8	0.2382 (2)	0.67650 (14)	0.5758 (2)	0.0562 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01604 (12)	0.01581 (11)	0.01054 (11)	0.00063 (8)	0.00604 (8)	−0.00088 (8)
N1	0.0231 (9)	0.0220 (8)	0.0147 (8)	−0.0018 (7)	0.0069 (7)	−0.0026 (6)
C1	0.0400 (13)	0.0202 (9)	0.0138 (9)	−0.0016 (8)	0.0126 (9)	−0.0019 (7)
C2	0.0409 (13)	0.0192 (9)	0.0213 (10)	0.0003 (8)	0.0219 (10)	−0.0004 (8)
C3	0.0252 (11)	0.0229 (9)	0.0248 (11)	−0.0002 (8)	0.0160 (9)	0.0026 (8)
N4	0.0184 (8)	0.0179 (7)	0.0165 (8)	0.0004 (6)	0.0088 (6)	−0.0006 (6)
C5	0.0210 (10)	0.0214 (9)	0.0206 (10)	0.0022 (8)	0.0062 (8)	−0.0036 (7)
C6	0.0365 (13)	0.0393 (12)	0.0175 (10)	0.0141 (10)	0.0079 (10)	0.0080 (9)
C7	0.0236 (12)	0.0371 (12)	0.0397 (15)	0.0104 (10)	0.0075 (10)	−0.0017 (11)
N11	0.0186 (8)	0.0212 (8)	0.0158 (8)	−0.0006 (6)	0.0045 (6)	−0.0025 (6)
C11	0.0279 (11)	0.0185 (9)	0.0201 (10)	0.0011 (8)	0.0033 (9)	−0.0045 (7)
C12	0.0294 (12)	0.0260 (10)	0.0173 (10)	0.0066 (8)	0.0093 (9)	−0.0031 (8)
C13	0.0226 (10)	0.0224 (9)	0.0172 (9)	0.0044 (7)	0.0075 (8)	0.0031 (7)
N14	0.0187 (8)	0.0194 (7)	0.0159 (8)	−0.0004 (6)	0.0079 (6)	−0.0012 (6)
C15	0.0241 (11)	0.0279 (10)	0.0178 (10)	−0.0033 (8)	0.0060 (8)	0.0012 (8)
C16	0.0412 (15)	0.0256 (11)	0.0351 (14)	−0.0047 (10)	0.0107 (11)	0.0051 (10)
C17	0.0360 (15)	0.0472 (15)	0.0483 (17)	−0.0052 (12)	0.0240 (13)	0.0094 (13)
Cl1	0.0233 (2)	0.0177 (2)	0.0139 (2)	0.00104 (17)	0.00612 (18)	0.00234 (15)
O1	0.0259 (8)	0.0245 (7)	0.0186 (7)	0.0021 (6)	0.0003 (6)	0.0026 (6)
O2	0.0478 (11)	0.0270 (8)	0.0364 (10)	0.0153 (8)	0.0105 (9)	−0.0034 (7)
O3	0.0267 (9)	0.0322 (9)	0.0402 (11)	−0.0059 (7)	−0.0031 (8)	−0.0028 (8)
O4	0.0575 (13)	0.0488 (11)	0.0318 (10)	0.0014 (9)	0.0296 (10)	0.0149 (8)
Cl2	0.0246 (2)	0.0230 (2)	0.0169 (2)	−0.00084 (18)	0.00805 (19)	−0.00162 (17)
O5	0.0877 (17)	0.0300 (9)	0.0284 (10)	−0.0051 (9)	0.0266 (11)	−0.0100 (7)
O6	0.0249 (9)	0.0470 (11)	0.0631 (14)	−0.0088 (8)	0.0121 (9)	−0.0081 (10)
O7	0.0591 (14)	0.0700 (14)	0.0280 (10)	−0.0192 (11)	0.0286 (10)	−0.0039 (10)
O8	0.0479 (13)	0.0421 (11)	0.0681 (16)	0.0106 (10)	−0.0060 (12)	0.0142 (11)

Geometric parameters (Å, º)

Cu1—N4	1.991 (2)	N11—H11B	0.9000
Cu1—N14	1.995 (2)	C11—C12	1.511 (3)
Cu1—N1	2.024 (2)	C11—H11C	0.9700
Cu1—N11	2.033 (2)	C11—H11D	0.9700
Cu1—O1	2.474 (2)	C12—C13	1.526 (3)
N1—C1	1.492 (3)	C12—H12A	0.9700
N1—H1A	0.9000	C12—H12B	0.9700
N1—H1B	0.9000	C13—N14	1.471 (2)
C1—C2	1.514 (3)	C13—H13A	0.9700
C1—H1C	0.9700	C13—H13B	0.9700
C1—H1D	0.9700	N14—C15	1.282 (3)
C2—C3	1.527 (3)	C15—C16	1.489 (3)
C2—H2A	0.9700	C15—C17	1.500 (3)
C2—H2B	0.9700	C16—H16A	0.9600
C3—N4	1.483 (3)	C16—H16B	0.9600
C3—H3A	0.9700	C16—H16C	0.9600
C3—H3B	0.9700	C17—H17A	0.9600
N4—C5	1.274 (3)	C17—H17B	0.9600
C5—C6	1.492 (3)	C17—H17C	0.9600
C5—C7	1.497 (3)	Cl1—O4	1.4265 (17)
C6—H6A	0.9600	Cl1—O2	1.4286 (16)
C6—H6B	0.9600	Cl1—O3	1.4428 (18)
C6—H6C	0.9600	Cl1—O1	1.4493 (16)
C7—H7A	0.9600	Cl2—O7	1.4167 (18)
C7—H7B	0.9600	Cl2—O8	1.428 (2)
C7—H7C	0.9600	Cl2—O5	1.4315 (17)
N11—C11	1.485 (3)	Cl2—O6	1.4365 (19)
N11—H11A	0.9000
N4—Cu1—N14	158.87 (7)	Cu1—N11—H11A	107.7
N4—Cu1—N1	88.15 (7)	C11—N11—H11B	107.7
N14—Cu1—N1	94.68 (7)	Cu1—N11—H11B	107.7
N4—Cu1—N11	91.79 (7)	H11A—N11—H11B	107.1
N14—Cu1—N11	88.27 (7)	N11—C11—C12	111.95 (17)
N1—Cu1—N11	171.96 (7)	N11—C11—H11C	109.2
N4—Cu1—O1	97.11 (6)	C12—C11—H11C	109.2
N14—Cu1—O1	103.83 (6)	N11—C11—H11D	109.2
N1—Cu1—O1	89.83 (6)	C12—C11—H11D	109.2
N11—Cu1—O1	82.20 (6)	H11C—C11—H11D	107.9
C1—N1—Cu1	118.66 (13)	C11—C12—C13	113.34 (17)
C1—N1—H1A	107.6	C11—C12—H12A	108.9
Cu1—N1—H1A	107.6	C13—C12—H12A	108.9
C1—N1—H1B	107.6	C11—C12—H12B	108.9
Cu1—N1—H1B	107.6	C13—C12—H12B	108.9
H1A—N1—H1B	107.1	H12A—C12—H12B	107.7
N1—C1—C2	112.54 (17)	N14—C13—C12	109.48 (17)
N1—C1—H1C	109.1	N14—C13—H13A	109.8
C2—C1—H1C	109.1	C12—C13—H13A	109.8
N1—C1—H1D	109.1	N14—C13—H13B	109.8
C2—C1—H1D	109.1	C12—C13—H13B	109.8
H1C—C1—H1D	107.8	H13A—C13—H13B	108.2
C1—C2—C3	114.02 (17)	C15—N14—C13	119.22 (18)
C1—C2—H2A	108.7	C15—N14—Cu1	125.15 (15)
C3—C2—H2A	108.7	C13—N14—Cu1	114.72 (12)
C1—C2—H2B	108.7	N14—C15—C16	121.1 (2)
C3—C2—H2B	108.7	N14—C15—C17	123.7 (2)
H2A—C2—H2B	107.6	C16—C15—C17	115.2 (2)
N4—C3—C2	108.22 (16)	C15—C16—H16A	109.5
N4—C3—H3A	110.1	C15—C16—H16B	109.5
C2—C3—H3A	110.1	H16A—C16—H16B	109.5
N4—C3—H3B	110.1	C15—C16—H16C	109.5
C2—C3—H3B	110.1	H16A—C16—H16C	109.5
H3A—C3—H3B	108.4	H16B—C16—H16C	109.5
C5—N4—C3	120.75 (18)	C15—C17—H17A	109.5
C5—N4—Cu1	124.95 (14)	C15—C17—H17B	109.5
C3—N4—Cu1	113.57 (13)	H17A—C17—H17B	109.5
N4—C5—C6	119.67 (19)	C15—C17—H17C	109.5
N4—C5—C7	125.5 (2)	H17A—C17—H17C	109.5
C6—C5—C7	114.8 (2)	H17B—C17—H17C	109.5
C5—C6—H6A	109.5	O4—Cl1—O2	110.61 (12)
C5—C6—H6B	109.5	O4—Cl1—O3	109.89 (12)
H6A—C6—H6B	109.5	O2—Cl1—O3	109.24 (12)
C5—C6—H6C	109.5	O4—Cl1—O1	109.31 (11)
H6A—C6—H6C	109.5	O2—Cl1—O1	109.68 (10)
H6B—C6—H6C	109.5	O3—Cl1—O1	108.07 (10)
C5—C7—H7A	109.5	Cl1—O1—Cu1	133.06 (9)
C5—C7—H7B	109.5	O7—Cl2—O8	111.18 (15)
H7A—C7—H7B	109.5	O7—Cl2—O5	109.07 (13)
C5—C7—H7C	109.5	O8—Cl2—O5	109.86 (14)
H7A—C7—H7C	109.5	O7—Cl2—O6	110.24 (13)
H7B—C7—H7C	109.5	O8—Cl2—O6	108.26 (13)
C11—N11—Cu1	118.45 (13)	O5—Cl2—O6	108.18 (14)
C11—N11—H11A	107.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O8	0.90	2.33	3.173 (3)	155
N1—H1B···O3^i	0.90	2.22	3.093 (3)	163
N11—H11A···O5^ii	0.90	2.20	3.077 (2)	165
N11—H11B···O6^iii	0.90	2.25	3.110 (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.