[(–)-α-Isosparteine]­dinitratocopper(II)

In the title compound, [Cu(NO₃)₂(C₁₅H₂₆N₂)], the Cu atom is coordinated by the two N atoms of the bidentate (−)-α-isosparteine (Sp) ligand and by two O atoms from two nitrate anions, forming a distorted tetrahedron; the two nitrate ligands are coordinated to the Cu atom in a monodentate mode. The dihedral angle between the N_Sp/Cu/N_Sp and O_nitrate/Cu/O_nitrate planes is 27.7 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.055
• wR factor = 0.129
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        O18
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        O20
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        O24
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         Cu
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N19
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N23
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         14

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               2451
           Count of symmetry unique reflns         1998
           Completeness (_total/calc)            122.67%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       453
           Fraction of Friedel pairs measured     0.227
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

[Cu(NO3)2(C15H26N2)]	F(000) = 884
Mr = 421.94	Dx = 1.59 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 40 reflections
a = 8.4920 (15) Å	θ = 6.0–12.8°
b = 12.241 (2) Å	µ = 1.28 mm^−1
c = 16.961 (3) Å	T = 293 K
V = 1763.1 (5) Å^3	Block, blue
Z = 4	0.38 × 0.34 × 0.28 mm

Data collection

Bruker P4 diffractometer	Rint = 0.040
2θ/ω scans	θmax = 26°, θmin = 2.1°
Absorption correction: psi scan (North et al., 1968)	h = −1→10
Tmin = 0.620, Tmax = 0.697	k = −15→1
2632 measured reflections	l = −20→1
2451 independent reflections	3 standard reflections every 97 reflections
1263 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.045P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.055	(Δ/σ)max < 0.001
wR(F^2) = 0.129	Δρmax = 0.49 e Å^−3
S = 0.97	Δρmin = −0.53 e Å^−3
2451 reflections	Absolute structure: Flack (1983), 453 Friedel pairs
233 parameters	Absolute structure parameter: −0.03 (4)
1 restraint

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu	0.08213 (14)	0.07445 (9)	0.34154 (7)	0.0387 (3)
N1	0.1426 (8)	−0.0692 (7)	0.3959 (4)	0.0347 (17)
C2	0.0206 (12)	−0.1567 (7)	0.3838 (5)	0.045 (3)
H2A	0.0026	−0.1662	0.3278	0.055*
H2B	0.0602	−0.2252	0.4046	0.055*
C3	−0.1326 (12)	−0.1300 (9)	0.4233 (6)	0.057 (3)
H3A	−0.2055	−0.1901	0.4158	0.069*
H3B	−0.1778	−0.0656	0.3988	0.069*
C4	−0.1116 (12)	−0.1092 (9)	0.5114 (6)	0.064 (3)
H4A	−0.0794	−0.1759	0.5376	0.076*
H4B	−0.2104	−0.0852	0.5342	0.076*
C5	0.0138 (12)	−0.0212 (8)	0.5225 (5)	0.051 (3)
H5A	0.0315	−0.0097	0.5784	0.061*
H5B	−0.0232	0.047	0.5	0.061*
C6	0.1685 (11)	−0.0541 (8)	0.4831 (5)	0.040 (3)
H6	0.1973	−0.1257	0.5044	0.048*
C7	0.3091 (13)	0.0229 (8)	0.4989 (5)	0.048 (3)
H7	0.3203	0.0298	0.5562	0.058*
C8	0.4334 (12)	−0.0370 (7)	0.3780 (5)	0.048 (3)
H8	0.5262	−0.0724	0.355	0.058*
N9	0.2860 (9)	0.1409 (6)	0.3774 (4)	0.041 (2)
C10	0.3059 (13)	0.2576 (7)	0.3516 (7)	0.055 (3)
H10A	0.4039	0.2859	0.3728	0.066*
H10B	0.2205	0.3011	0.3731	0.066*
C11	0.3073 (14)	0.2691 (8)	0.2626 (6)	0.063 (3)
H11A	0.2074	0.2448	0.2412	0.076*
H11B	0.3218	0.3452	0.2484	0.076*
C12	0.4394 (15)	0.2014 (8)	0.2284 (6)	0.066 (3)
H12A	0.4319	0.2025	0.1713	0.08*
H12B	0.5394	0.234	0.243	0.08*
C13	0.4361 (13)	0.0847 (7)	0.2563 (5)	0.054 (3)
H13A	0.5307	0.0474	0.2389	0.064*
H13B	0.3461	0.0475	0.2336	0.064*
C14	0.4259 (11)	0.0800 (7)	0.3460 (5)	0.049 (2)
H14	0.5194	0.1177	0.3661	0.058*
C15	0.2923 (10)	−0.1060 (7)	0.3586 (5)	0.043 (3)
H15A	0.2783	−0.1064	0.3018	0.052*
H15B	0.3133	−0.1805	0.3749	0.052*
C16	0.2878 (14)	0.1364 (7)	0.4661 (5)	0.049 (3)
H16A	0.1896	0.1661	0.4858	0.058*
H16B	0.3725	0.1824	0.4853	0.058*
C17	0.4570 (11)	−0.0322 (9)	0.4681 (5)	0.056 (3)
H17A	0.4679	−0.1051	0.49	0.067*
H17B	0.55	0.01	0.4814	0.067*
O18	−0.0226 (10)	0.2200 (6)	0.3219 (5)	0.071 (3)
N19	−0.1448 (12)	0.2251 (8)	0.3592 (5)	0.054 (3)
O20	−0.1767 (9)	0.1549 (7)	0.4089 (5)	0.074 (2)
O21	−0.2419 (10)	0.3004 (6)	0.3452 (5)	0.089 (3)
O22	−0.0798 (10)	0.0075 (5)	0.2734 (4)	0.0628 (19)
N23	−0.0562 (14)	0.0304 (7)	0.2016 (6)	0.065 (3)
O24	0.0719 (11)	0.0725 (6)	0.1862 (4)	0.077 (2)
O25	−0.1552 (11)	0.0098 (8)	0.1523 (5)	0.107 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0435 (6)	0.0346 (5)	0.0380 (5)	0.0034 (7)	0.0003 (7)	0.0020 (7)
N1	0.041 (4)	0.036 (4)	0.027 (3)	0.005 (5)	−0.009 (3)	−0.003 (4)
C2	0.062 (7)	0.036 (5)	0.038 (5)	−0.008 (6)	−0.006 (6)	−0.013 (5)
C3	0.061 (8)	0.046 (6)	0.065 (7)	−0.002 (6)	0.003 (6)	0.016 (6)
C4	0.051 (7)	0.084 (8)	0.056 (7)	0.007 (7)	0.004 (6)	0.020 (6)
C5	0.071 (7)	0.048 (6)	0.032 (5)	0.011 (7)	0.005 (5)	0.005 (5)
C6	0.052 (6)	0.041 (6)	0.028 (5)	−0.001 (6)	−0.007 (5)	0.001 (5)
C7	0.074 (8)	0.040 (6)	0.030 (5)	−0.003 (6)	−0.007 (6)	0.004 (5)
C8	0.030 (5)	0.054 (6)	0.062 (6)	0.007 (6)	0.004 (6)	0.004 (5)
N9	0.051 (5)	0.034 (4)	0.038 (4)	0.001 (5)	0.000 (4)	0.003 (4)
C10	0.060 (7)	0.033 (5)	0.073 (8)	−0.014 (6)	0.015 (8)	0.000 (6)
C11	0.086 (9)	0.052 (7)	0.052 (7)	−0.014 (7)	0.000 (7)	0.019 (6)
C12	0.070 (8)	0.073 (7)	0.056 (7)	−0.017 (8)	0.018 (8)	0.019 (6)
C13	0.054 (6)	0.061 (6)	0.046 (5)	0.011 (8)	0.020 (6)	0.009 (6)
C14	0.034 (5)	0.053 (5)	0.059 (5)	−0.007 (8)	0.004 (7)	0.012 (7)
C15	0.054 (7)	0.041 (6)	0.036 (6)	0.013 (5)	0.003 (5)	−0.004 (5)
C16	0.067 (8)	0.043 (6)	0.036 (6)	−0.006 (7)	−0.002 (6)	−0.004 (5)
C17	0.050 (7)	0.069 (7)	0.048 (6)	0.016 (6)	−0.016 (5)	−0.002 (6)
O18	0.057 (5)	0.053 (5)	0.103 (7)	0.003 (5)	0.010 (5)	0.009 (5)
N19	0.081 (8)	0.037 (5)	0.043 (6)	−0.013 (6)	0.001 (6)	0.002 (5)
O20	0.05	0.092 (6)	0.081 (6)	0.010 (5)	0.003 (5)	−0.004 (5)
O21	0.095 (6)	0.069 (5)	0.103 (6)	0.037 (6)	−0.021 (7)	−0.005 (6)
O22	0.088 (5)	0.055 (4)	0.045 (4)	−0.014 (5)	−0.016 (5)	0.017 (4)
N23	0.082 (8)	0.049 (5)	0.065 (7)	−0.021 (6)	−0.015 (7)	0.012 (5)
O24	0.092 (5)	0.065	0.073 (5)	−0.009 (7)	0.027 (5)	−0.021 (5)
O25	0.123 (8)	0.131 (8)	0.067 (6)	−0.030 (7)	−0.038 (6)	0.019 (6)

Geometric parameters (Å, º)

Cu—O22	1.974 (7)	C8—H8	0.98
Cu—N9	2.007 (8)	N9—C14	1.501 (11)
Cu—O18	2.019 (8)	N9—C10	1.504 (10)
Cu—N1	2.051 (8)	N9—C16	1.506 (10)
Cu—O24	2.636 (7)	C10—C11	1.516 (15)
Cu—O20	2.665 (7)	C10—H10A	0.97
N1—C15	1.490 (10)	C10—H10B	0.97
N1—C2	1.504 (10)	C11—C12	1.511 (14)
N1—C6	1.507 (9)	C11—H11A	0.97
C2—C3	1.499 (12)	C11—H11B	0.97
C2—H2A	0.97	C12—C13	1.505 (12)
C2—H2B	0.97	C12—H12A	0.97
C3—C4	1.525 (13)	C12—H12B	0.97
C3—H3A	0.97	C13—C14	1.524 (11)
C3—H3B	0.97	C13—H13A	0.97
C4—C5	1.526 (12)	C13—H13B	0.97
C4—H4A	0.97	C14—H14	0.98
C4—H4B	0.97	C15—H15A	0.97
C5—C6	1.528 (11)	C15—H15B	0.97
C5—H5A	0.97	C16—H16A	0.97
C5—H5B	0.97	C16—H16B	0.97
C6—C7	1.545 (12)	C17—H17A	0.97
C6—H6	0.98	C17—H17B	0.97
C7—C16	1.507 (12)	O18—N19	1.216 (7)
C7—C17	1.519 (12)	N19—O20	1.234 (10)
C7—H7	0.98	N19—O21	1.259 (11)
C8—C15	1.502 (12)	O22—N23	1.266 (10)
C8—C14	1.533 (12)	N23—O25	1.212 (11)
C8—C17	1.544 (11)	N23—O24	1.231 (11)
O22—Cu—N9	161.2 (3)	C14—N9—C16	109.1 (8)
O22—Cu—O18	87.9 (3)	C10—N9—C16	108.9 (7)
N9—Cu—O18	94.2 (3)	C14—N9—Cu	112.0 (5)
O22—Cu—N1	94.7 (3)	C10—N9—Cu	113.2 (6)
N9—Cu—N1	89.7 (3)	C16—N9—Cu	107.3 (6)
O18—Cu—N1	160.2 (3)	N9—C10—C11	112.2 (8)
O22—Cu—O24	52.3 (3)	N9—C10—H10A	109.2
N9—Cu—O24	109.6 (3)	C11—C10—H10A	109.2
O18—Cu—O24	80.1 (3)	N9—C10—H10B	109.2
N1—Cu—O24	116.7 (3)	C11—C10—H10B	109.2
O22—Cu—O20	80.2 (3)	H10A—C10—H10B	107.9
N9—Cu—O20	115.6 (3)	C12—C11—C10	109.7 (9)
O18—Cu—O20	51.8 (3)	C12—C11—H11A	109.7
N1—Cu—O20	109.3 (3)	C10—C11—H11A	109.7
O24—Cu—O20	113.8 (3)	C12—C11—H11B	109.7
C15—N1—C2	108.3 (7)	C10—C11—H11B	109.7
C15—N1—C6	109.3 (6)	H11A—C11—H11B	108.2
C2—N1—C6	108.8 (7)	C13—C12—C11	112.7 (9)
C15—N1—Cu	106.3 (5)	C13—C12—H12A	109
C2—N1—Cu	112.1 (5)	C11—C12—H12A	109
C6—N1—Cu	111.9 (6)	C13—C12—H12B	109
C3—C2—N1	112.4 (7)	C11—C12—H12B	109
C3—C2—H2A	109.1	H12A—C12—H12B	107.8
N1—C2—H2A	109.1	C12—C13—C14	110.5 (8)
C3—C2—H2B	109.1	C12—C13—H13A	109.5
N1—C2—H2B	109.1	C14—C13—H13A	109.5
H2A—C2—H2B	107.9	C12—C13—H13B	109.5
C2—C3—C4	111.9 (8)	C14—C13—H13B	109.5
C2—C3—H3A	109.2	H13A—C13—H13B	108.1
C4—C3—H3A	109.2	N9—C14—C13	112.4 (8)
C2—C3—H3B	109.2	N9—C14—C8	111.8 (8)
C4—C3—H3B	109.2	C13—C14—C8	112.7 (8)
H3A—C3—H3B	107.9	N9—C14—H14	106.5
C3—C4—C5	108.7 (8)	C13—C14—H14	106.5
C3—C4—H4A	109.9	C8—C14—H14	106.5
C5—C4—H4A	109.9	N1—C15—C8	114.7 (7)
C3—C4—H4B	109.9	N1—C15—H15A	108.6
C5—C4—H4B	109.9	C8—C15—H15A	108.6
H4A—C4—H4B	108.3	N1—C15—H15B	108.6
C4—C5—C6	111.1 (8)	C8—C15—H15B	108.6
C4—C5—H5A	109.4	H15A—C15—H15B	107.6
C6—C5—H5A	109.4	N9—C16—C7	113.9 (8)
C4—C5—H5B	109.4	N9—C16—H16A	108.8
C6—C5—H5B	109.4	C7—C16—H16A	108.8
H5A—C5—H5B	108	N9—C16—H16B	108.8
N1—C6—C5	109.7 (7)	C7—C16—H16B	108.8
N1—C6—C7	111.0 (7)	H16A—C16—H16B	107.7
C5—C6—C7	115.3 (8)	C7—C17—C8	104.5 (8)
N1—C6—H6	106.8	C7—C17—H17A	110.9
C5—C6—H6	106.8	C8—C17—H17A	110.9
C7—C6—H6	106.8	C7—C17—H17B	110.9
C16—C7—C17	112.5 (9)	C8—C17—H17B	110.9
C16—C7—C6	113.9 (9)	H17A—C17—H17B	108.9
C17—C7—C6	107.9 (7)	N19—O18—Cu	109.6 (8)
C16—C7—H7	107.4	O18—N19—O20	120.4 (11)
C17—C7—H7	107.4	O18—N19—O21	119.9 (10)
C6—C7—H7	107.4	O20—N19—O21	119.6 (10)
C15—C8—C14	114.5 (8)	N19—O20—Cu	77.5 (6)
C15—C8—C17	110.0 (8)	N23—O22—Cu	111.1 (7)
C14—C8—C17	108.7 (8)	O25—N23—O24	123.6 (11)
C15—C8—H8	107.8	O25—N23—O22	120.5 (11)
C14—C8—H8	107.8	O24—N23—O22	115.9 (10)
C17—C8—H8	107.8	N23—O24—Cu	79.7 (6)
C14—N9—C10	106.3 (7)