trans-Bis­[2,3-di­amino-(R,S)-propion­ato-N,N']­di­aqua­copper(II) dihydrate

The title copper complex, [Cu(DL-DAP)₂(H₂O)₂]·2H₂O or [Cu(C₃H₇N₂O₂)₂(H₂O)₂]·2H₂O, prepared from the non-protein amino acid DL-2,3-di­amino­propionic acid (DL-HDAP), has a center of symmetry and a distorted octahedral coordination, with four N atoms in equatorial positions and two water mol­ecules in apical sites. The water mol­ecule of crystallization is hydrogen bonded to the deprotonated carboxyl­ate group of the ligand.

Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1992); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: DIRDIF96 (Beurskens et al., 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

[Cu(C3H7N2O2)2(H2O)2]·2H2O	Z = 1
Mr = 341.82	F(000) = 179
Triclinic, P1	Dx = 1.746 Mg m^−3
a = 6.507 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.448 (2) Å	Cell parameters from 25 reflections
c = 7.735 (2) Å	θ = 11.0–13.7°
α = 109.25 (4)°	µ = 1.72 mm^−1
β = 95.11 (4)°	T = 180 K
γ = 109.52 (5)°	Prism, violet
V = 325.10 (13) Å^3	0.2 × 0.2 × 0.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.019
non–profiled ω/2θ scans	θmax = 26.9°, θmin = 2.9°
Absorption correction: ψ scan (North et al., 1968)	h = −8→7
Tmin = 0.712, Tmax = 0.842	k = 0→9
1527 measured reflections	l = −9→9
1417 independent reflections	2 standard reflections every 60 min
1265 reflections with I > 2σ(I)	intensity decay: 26%

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.068P)^2 + 0.2597P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.106	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 1.15 e Å^−3
1417 reflections	Δρmin = −1.18 e Å^−3
133 parameters

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
Cu1	0	0	0	0.01351 (19)
N1	0.2830 (4)	0.1141 (5)	−0.0823 (4)	0.0165 (5)
N2	−0.1296 (4)	0.1150 (5)	−0.1651 (4)	0.0162 (5)
O1	0.6085 (4)	0.3693 (4)	−0.1976 (3)	0.0225 (5)
O2	0.3838 (4)	0.2611 (4)	−0.4779 (3)	0.0229 (5)
O3	0.1020 (4)	0.3411 (4)	0.2924 (3)	0.0216 (5)
O4	0.6475 (4)	0.2698 (4)	0.2599 (4)	0.0261 (6)
C1	0.0559 (5)	0.2483 (6)	−0.2210 (5)	0.0236 (7)
C2	0.2234 (5)	0.1474 (5)	−0.2540 (5)	0.0223 (7)
C3	0.4239 (5)	0.2736 (5)	−0.3114 (4)	0.0167 (6)
H1	−0.205 (8)	0.029 (7)	−0.258 (6)	0.027 (12)*
H2	−0.199 (6)	0.187 (6)	−0.110 (5)	0.017 (9)*
H3	−0.005 (6)	0.260 (6)	−0.336 (5)	0.014 (9)*
H4	0.142 (10)	0.397 (10)	−0.094 (8)	0.066 (17)*
H5	0.140 (8)	−0.002 (8)	−0.369 (7)	0.038 (12)*
H6	0.326 (10)	0.023 (9)	−0.125 (8)	0.052 (16)*
H7	0.368 (8)	0.214 (8)	0.003 (7)	0.032 (12)*
H8	0.185 (8)	0.429 (7)	0.270 (8)	0.057 (17)*
H9	0.177 (7)	0.334 (7)	0.373 (5)	0.029 (12)*
H10	0.599 (7)	0.285 (7)	0.351 (5)	0.028 (11)*
H11	0.776 (5)	0.321 (7)	0.288 (7)	0.041 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0092 (3)	0.0185 (3)	0.0175 (3)	0.0052 (2)	0.00514 (19)	0.0121 (2)
N1	0.0118 (12)	0.0210 (14)	0.0180 (13)	0.0042 (11)	0.0028 (10)	0.0113 (12)
N2	0.0119 (12)	0.0195 (13)	0.0192 (13)	0.0055 (11)	0.0044 (11)	0.0102 (12)
O1	0.0161 (11)	0.0278 (13)	0.0259 (12)	0.0042 (9)	0.0035 (9)	0.0176 (10)
O2	0.0212 (11)	0.0285 (12)	0.0223 (11)	0.0076 (10)	0.0068 (9)	0.0152 (10)
O3	0.0154 (11)	0.0226 (12)	0.0263 (13)	0.0034 (9)	0.0024 (10)	0.0132 (10)
O4	0.0183 (12)	0.0328 (14)	0.0216 (12)	0.0087 (11)	0.0030 (10)	0.0052 (11)
C1	0.0168 (15)	0.0333 (19)	0.0319 (18)	0.0104 (14)	0.0099 (13)	0.0242 (16)
C2	0.0192 (16)	0.0300 (18)	0.0245 (16)	0.0099 (14)	0.0061 (13)	0.0179 (15)
C3	0.0139 (14)	0.0196 (15)	0.0235 (15)	0.0075 (12)	0.0076 (12)	0.0146 (13)

Geometric parameters (Å, º)

Cu1—N1	2.009 (3)	O1—C3	1.246 (4)
Cu1—N1^i	2.009 (3)	O2—C3	1.257 (4)
Cu1—N2^i	2.022 (3)	O3—H8	0.78 (3)
Cu1—N2	2.022 (3)	O3—H9	0.78 (3)
Cu1—O3^i	2.613 (3)	O4—H10	0.78 (3)
Cu1—O3	2.613 (3)	O4—H11	0.77 (3)
N1—C2	1.472 (4)	C1—C2	1.513 (5)
N1—H6	0.80 (6)	C1—H3	0.98 (4)
N1—H7	0.79 (5)	C1—H4	1.13 (6)
N2—C1	1.485 (4)	C2—C3	1.530 (4)
N2—H1	0.77 (5)	C2—H5	1.09 (5)
N2—H2	0.84 (4)
N1—Cu1—N1^i	180.0	Cu1—N2—H2	113 (3)
N1—Cu1—N2^i	95.64 (11)	H1—N2—H2	111 (4)
N1^i—Cu1—N2^i	84.36 (11)	H8—O3—H9	103 (5)
N1—Cu1—N2	84.36 (11)	H10—O4—H11	109 (5)
N1^i—Cu1—N2	95.64 (11)	N2—C1—C2	107.3 (3)
N1—Cu1—O3	92.66 (12)	N2—C1—H3	109 (2)
N2^i—Cu1—N2	180.0	C2—C1—H3	111 (2)
N2—Cu1—O3	90.75 (11)	N2—C1—H4	106 (3)
O3^i—Cu1—O3	180.0	C2—C1—H4	106 (3)
C2—N1—Cu1	108.12 (19)	H3—C1—H4	116 (4)
C2—N1—H6	100 (4)	N1—C2—C1	106.9 (3)
Cu1—N1—H6	108 (4)	N1—C2—C3	114.0 (3)
C2—N1—H7	115 (3)	C1—C2—C3	111.7 (3)
Cu1—N1—H7	109 (3)	N1—C2—H5	108 (2)
H6—N1—H7	117 (5)	C1—C2—H5	108 (3)
C1—N2—Cu1	108.73 (19)	C3—C2—H5	108 (2)
C1—N2—H1	105 (3)	O1—C3—O2	126.3 (3)
Cu1—N2—H1	111 (3)	O1—C3—C2	119.4 (3)
C1—N2—H2	108 (3)	O2—C3—C2	114.3 (3)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O2^ii	0.77 (5)	2.27 (5)	3.033 (5)	168 (4)
N2—H2···O1^iii	0.84 (4)	2.34 (4)	2.991 (4)	134 (3)
N1—H6···O4^iv	0.80 (6)	2.16 (6)	2.941 (4)	166 (6)
N1—H7···O4	0.79 (5)	2.40 (5)	2.999 (4)	134 (4)
O3—H8···O1^v	0.78 (3)	1.93 (3)	2.704 (3)	175 (6)
O3—H9···O2^vi	0.78 (3)	2.02 (3)	2.779 (4)	165 (5)
O4—H10···O2^vi	0.78 (3)	2.02 (3)	2.774 (4)	162 (4)
O4—H11···O3^vii	0.77 (3)	2.08 (3)	2.797 (3)	157 (5)

Symmetry codes: (ii) −x, −y, −z−1; (iii) x−1, y, z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z; (vi) x, y, z+1; (vii) x+1, y, z.