Aqua-(1,10-phenanthroline-κN,N')(dl-threoninato-κN,O)copper(II) chloride dihydrate.

The asymmetric unit of the title compound, [Cu(C(4)H(8)NO(3))(C(12)H(8)N(2))(H(2)O)]Cl·2H(2)O, contains a complex cation, a chloride anion and two water mol-ecules. The Cu(II) ion has a distorted square-pyramidal coordination geometry formed by one bidentate phenanthroline ligand, one O,N-bidentate dl-threoninate ligand and one apical water mol-ecule. In the crystal structure, inter-molecular O-H⋯O, N-H⋯O, N-H⋯Cl and O-H⋯Cl hydrogen bonds link the components into layers. A single weak inter-molecular C-H⋯O inter-action connects these layers into a three-dimensional network.

Related literature

For background to the inter­actions of transition-metal complexes with DNA, see: Vaidyanathan & Nair (2003 ▶); Rao et al. (2007 ▶, 2008 ▶); Kumar & Arunachalam (2007 ▶); Patel et al. (2006 ▶); Wang et al. (2007 ▶); Zhang et al. (2004 ▶). For a related structure, see: Lu et al. (2004 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Cu(C4H8NO3)(C12H8N2)(H2O)]Cl·2H2O

M = 451.36

Triclinic,

a = 7.1972 (1) Å

b = 11.9785 (2) Å

c = 12.2915 (2) Å

α = 65.664 (1)°

β = 78.079 (1)°

γ = 81.345 (1)°

V = 942.15 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.34 mm−1

T = 296 K

0.34 × 0.20 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.656, T max = 0.911

29845 measured reflections

8056 independent reflections

5995 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.04

8056 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015278/lh5025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015278/lh5025Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C4H8NO3)(C12H8N2)(H2O)]Cl·2H2O	Z = 2
Mr = 451.36	F(000) = 466
Triclinic, P1	Dx = 1.591 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1972 (1) Å	Cell parameters from 9968 reflections
b = 11.9785 (2) Å	θ = 2.9–32.7°
c = 12.2915 (2) Å	µ = 1.34 mm−1
α = 65.664 (1)°	T = 296 K
β = 78.079 (1)°	Block, blue
γ = 81.345 (1)°	0.34 × 0.20 × 0.07 mm
V = 942.15 (3) Å3

Bruker APEXII DUO CCD area-detector diffractometer	8056 independent reflections
Radiation source: fine-focus sealed tube	5995 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 34.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.656, Tmax = 0.911	k = −18→19
29845 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3
8056 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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

	x	y	z	Uiso*/Ueq
Cu1	0.76442 (2)	0.603112 (14)	0.250328 (14)	0.02828 (5)
O1W	0.45829 (16)	0.66307 (10)	0.28057 (11)	0.0473 (3)
H1W1	0.3972	0.7227	0.2422	0.071*
H2W1	0.3770	0.6135	0.3201	0.071*
O1	0.77687 (16)	0.50694 (9)	0.42081 (9)	0.0359 (2)
O2	0.7643 (2)	0.52774 (11)	0.59298 (9)	0.0493 (3)
O3	1.07351 (19)	0.74151 (11)	0.44492 (13)	0.0558 (3)
H1O3	1.0957	0.6609	0.4891	0.084*
N1	0.72609 (17)	0.45456 (11)	0.22337 (11)	0.0325 (2)
N2	0.80300 (17)	0.67993 (11)	0.06759 (10)	0.0305 (2)
N3	0.83142 (17)	0.74053 (10)	0.28305 (10)	0.0296 (2)
H1N3	0.9497	0.7564	0.2596	0.036*
H2N3	0.7570	0.8122	0.2433	0.036*
C1	0.74069 (19)	0.47692 (13)	0.10467 (13)	0.0314 (3)
C2	0.6821 (2)	0.34333 (14)	0.30518 (16)	0.0407 (3)
H2A	0.6704	0.3275	0.3869	0.049*
C3	0.6532 (3)	0.24997 (15)	0.27161 (19)	0.0491 (4)
H3A	0.6223	0.1733	0.3307	0.059*
C4	0.6702 (3)	0.27118 (16)	0.15218 (19)	0.0484 (4)
H4A	0.6526	0.2088	0.1296	0.058*
C5	0.7146 (2)	0.38811 (15)	0.06321 (16)	0.0394 (3)
C6	0.7318 (2)	0.42233 (18)	−0.06444 (17)	0.0482 (4)
H6A	0.7168	0.3641	−0.0932	0.058*
C7	0.7694 (2)	0.53790 (18)	−0.14407 (16)	0.0467 (4)
H7A	0.7796	0.5575	−0.2265	0.056*
C8	0.7939 (2)	0.63054 (16)	−0.10411 (14)	0.0381 (3)
C9	0.8273 (2)	0.75297 (17)	−0.18067 (14)	0.0454 (4)
H9A	0.8351	0.7788	−0.2638	0.054*
C10	0.8481 (2)	0.83416 (16)	−0.13287 (14)	0.0437 (4)
H10A	0.8698	0.9154	−0.1833	0.052*
C11	0.8368 (2)	0.79473 (14)	−0.00808 (13)	0.0364 (3)
H11A	0.8534	0.8506	0.0232	0.044*
C12	0.78101 (19)	0.59920 (14)	0.01996 (13)	0.0309 (3)
C13	0.7721 (2)	0.57113 (13)	0.48255 (12)	0.0322 (3)
C14	0.7668 (2)	0.71093 (13)	0.41344 (12)	0.0319 (3)
H14A	0.6330	0.7421	0.4225	0.038*
C15	0.8735 (3)	0.77207 (14)	0.46657 (14)	0.0409 (3)
H15A	0.8300	0.7424	0.5541	0.049*
C16	0.8433 (3)	0.91054 (16)	0.4121 (2)	0.0563 (5)
H16A	0.9172	0.9447	0.4461	0.084*
H16B	0.7109	0.9346	0.4297	0.084*
H16C	0.8827	0.9403	0.3261	0.084*
Cl1	0.22654 (6)	0.87371 (4)	0.09619 (4)	0.04803 (10)
O2W	0.4269 (2)	0.03917 (12)	0.83732 (12)	0.0539 (3)
H1W2	0.5174	0.0603	0.8600	0.081*
H2W2	0.3827	−0.0182	0.9014	0.081*
O3W	0.6557 (2)	0.08312 (18)	0.59634 (17)	0.0851 (5)
H1W3	0.5665	0.0630	0.6763	0.128*
H2W3	0.7213	0.1408	0.6002	0.128*

	U11	U22	U33	U12	U13	U23
Cu1	0.03672 (10)	0.02541 (8)	0.02496 (8)	−0.00530 (6)	−0.00529 (6)	−0.01097 (6)
O1W	0.0328 (5)	0.0366 (6)	0.0579 (7)	−0.0045 (4)	−0.0043 (5)	−0.0048 (5)
O1	0.0538 (6)	0.0256 (4)	0.0297 (5)	−0.0058 (4)	−0.0116 (4)	−0.0091 (4)
O2	0.0797 (9)	0.0429 (6)	0.0247 (5)	−0.0253 (6)	−0.0091 (5)	−0.0056 (4)
O3	0.0573 (8)	0.0389 (6)	0.0764 (9)	−0.0043 (5)	−0.0328 (7)	−0.0172 (6)
N1	0.0361 (6)	0.0288 (6)	0.0358 (6)	−0.0036 (5)	−0.0063 (5)	−0.0153 (5)
N2	0.0347 (6)	0.0314 (6)	0.0278 (5)	−0.0040 (5)	−0.0045 (4)	−0.0138 (4)
N3	0.0370 (6)	0.0273 (5)	0.0246 (5)	−0.0077 (4)	−0.0041 (4)	−0.0088 (4)
C1	0.0290 (6)	0.0341 (7)	0.0391 (7)	0.0011 (5)	−0.0089 (5)	−0.0221 (6)
C2	0.0470 (8)	0.0300 (7)	0.0449 (8)	−0.0055 (6)	−0.0078 (7)	−0.0137 (6)
C3	0.0521 (10)	0.0301 (7)	0.0664 (12)	−0.0059 (7)	−0.0099 (9)	−0.0192 (8)
C4	0.0465 (9)	0.0380 (8)	0.0762 (13)	0.0006 (7)	−0.0169 (9)	−0.0357 (9)
C5	0.0348 (7)	0.0408 (8)	0.0566 (10)	0.0045 (6)	−0.0136 (7)	−0.0326 (7)
C6	0.0465 (9)	0.0598 (11)	0.0623 (11)	0.0067 (8)	−0.0192 (8)	−0.0464 (10)
C7	0.0465 (9)	0.0663 (11)	0.0438 (9)	0.0066 (8)	−0.0156 (7)	−0.0378 (9)
C8	0.0339 (7)	0.0530 (9)	0.0345 (7)	0.0040 (6)	−0.0100 (6)	−0.0246 (7)
C9	0.0470 (9)	0.0588 (10)	0.0288 (7)	0.0008 (8)	−0.0080 (6)	−0.0165 (7)
C10	0.0497 (9)	0.0430 (8)	0.0308 (7)	−0.0044 (7)	−0.0045 (6)	−0.0076 (6)
C11	0.0421 (8)	0.0338 (7)	0.0319 (7)	−0.0060 (6)	−0.0033 (6)	−0.0118 (6)
C12	0.0274 (6)	0.0383 (7)	0.0324 (6)	0.0009 (5)	−0.0066 (5)	−0.0194 (6)
C13	0.0390 (7)	0.0303 (6)	0.0266 (6)	−0.0096 (5)	−0.0058 (5)	−0.0080 (5)
C14	0.0401 (7)	0.0293 (6)	0.0275 (6)	−0.0050 (5)	−0.0042 (5)	−0.0120 (5)
C15	0.0605 (10)	0.0353 (7)	0.0331 (7)	−0.0103 (7)	−0.0100 (7)	−0.0161 (6)
C16	0.0703 (12)	0.0361 (8)	0.0740 (13)	−0.0048 (8)	−0.0184 (10)	−0.0296 (9)
Cl1	0.0520 (2)	0.03659 (19)	0.0500 (2)	−0.01029 (17)	−0.01205 (18)	−0.00742 (17)
O2W	0.0616 (8)	0.0483 (7)	0.0475 (7)	−0.0081 (6)	−0.0133 (6)	−0.0114 (6)
O3W	0.0749 (11)	0.1128 (15)	0.0905 (13)	−0.0229 (10)	−0.0039 (9)	−0.0616 (12)

Cu1—O1	1.9450 (10)	C4—H4A	0.9300
Cu1—N3	1.9921 (11)	C5—C6	1.432 (2)
Cu1—N1	2.0059 (12)	C6—C7	1.354 (3)
Cu1—N2	2.0210 (11)	C6—H6A	0.9300
Cu1—O1W	2.2167 (11)	C7—C8	1.431 (2)
O1W—H1W1	0.7992	C7—H7A	0.9300
O1W—H2W1	0.8250	C8—C12	1.398 (2)
O1—C13	1.2770 (17)	C8—C9	1.403 (3)
O2—C13	1.2295 (17)	C9—C10	1.366 (2)
O3—C15	1.429 (2)	C9—H9A	0.9300
O3—H1O3	0.9002	C10—C11	1.395 (2)
N1—C2	1.3333 (19)	C10—H10A	0.9300
N1—C1	1.3545 (19)	C11—H11A	0.9300
N2—C11	1.3298 (18)	C13—C14	1.5326 (19)
N2—C12	1.3615 (17)	C14—C15	1.524 (2)
N3—C14	1.4778 (17)	C14—H14A	0.9800
N3—H1N3	0.8636	C15—C16	1.511 (2)
N3—H2N3	0.9420	C15—H15A	0.9800
C1—C5	1.4047 (19)	C16—H16A	0.9600
C1—C12	1.435 (2)	C16—H16B	0.9600
C2—C3	1.397 (2)	C16—H16C	0.9600
C2—H2A	0.9300	O2W—H1W2	0.8654
C3—C4	1.365 (3)	O2W—H2W2	0.8422
C3—H3A	0.9300	O3W—H1W3	1.0137
C4—C5	1.410 (3)	O3W—H2W3	0.9153
O1—Cu1—N3	84.44 (4)	C7—C6—H6A	119.4
O1—Cu1—N1	92.20 (5)	C5—C6—H6A	119.4
N3—Cu1—N1	173.26 (5)	C6—C7—C8	121.40 (15)
O1—Cu1—N2	167.52 (5)	C6—C7—H7A	119.3
N3—Cu1—N2	99.88 (5)	C8—C7—H7A	119.3
N1—Cu1—N2	82.23 (5)	C12—C8—C9	116.68 (14)
O1—Cu1—O1W	94.75 (5)	C12—C8—C7	118.61 (16)
N3—Cu1—O1W	89.99 (5)	C9—C8—C7	124.70 (15)
N1—Cu1—O1W	96.12 (5)	C10—C9—C8	119.91 (14)
N2—Cu1—O1W	96.94 (5)	C10—C9—H9A	120.0
Cu1—O1W—H1W1	131.4	C8—C9—H9A	120.0
Cu1—O1W—H2W1	121.8	C9—C10—C11	119.74 (15)
H1W1—O1W—H2W1	103.0	C9—C10—H10A	120.1
C13—O1—Cu1	114.26 (9)	C11—C10—H10A	120.1
C15—O3—H1O3	108.0	N2—C11—C10	122.16 (14)
C2—N1—C1	118.50 (13)	N2—C11—H11A	118.9
C2—N1—Cu1	128.75 (11)	C10—C11—H11A	118.9
C1—N1—Cu1	112.69 (9)	N2—C12—C8	123.41 (14)
C11—N2—C12	118.07 (12)	N2—C12—C1	116.42 (12)
C11—N2—Cu1	129.83 (10)	C8—C12—C1	120.17 (13)
C12—N2—Cu1	112.02 (9)	O2—C13—O1	123.99 (13)
C14—N3—Cu1	106.69 (8)	O2—C13—C14	119.04 (13)
C14—N3—H1N3	113.4	O1—C13—C14	116.91 (11)
Cu1—N3—H1N3	114.4	N3—C14—C15	114.04 (12)
C14—N3—H2N3	105.0	N3—C14—C13	109.43 (11)
Cu1—N3—H2N3	108.9	C15—C14—C13	112.30 (12)
H1N3—N3—H2N3	108.0	N3—C14—H14A	106.9
N1—C1—C5	123.26 (14)	C15—C14—H14A	106.9
N1—C1—C12	116.62 (12)	C13—C14—H14A	106.9
C5—C1—C12	120.10 (14)	O3—C15—C16	107.21 (14)
N1—C2—C3	121.86 (16)	O3—C15—C14	110.23 (13)
N1—C2—H2A	119.1	C16—C15—C14	112.68 (14)
C3—C2—H2A	119.1	O3—C15—H15A	108.9
C4—C3—C2	120.03 (16)	C16—C15—H15A	108.9
C4—C3—H3A	120.0	C14—C15—H15A	108.9
C2—C3—H3A	120.0	C15—C16—H16A	109.5
C3—C4—C5	119.66 (15)	C15—C16—H16B	109.5
C3—C4—H4A	120.2	H16A—C16—H16B	109.5
C5—C4—H4A	120.2	C15—C16—H16C	109.5
C1—C5—C4	116.68 (15)	H16A—C16—H16C	109.5
C1—C5—C6	118.46 (15)	H16B—C16—H16C	109.5
C4—C5—C6	124.85 (15)	H1W2—O2W—H2W2	101.9
C7—C6—C5	121.24 (15)	H1W3—O3W—H2W3	98.8
N3—Cu1—O1—C13	16.30 (10)	C1—C5—C6—C7	−1.0 (2)
N1—Cu1—O1—C13	−169.56 (10)	C4—C5—C6—C7	178.03 (17)
N2—Cu1—O1—C13	127.31 (19)	C5—C6—C7—C8	0.1 (3)
O1W—Cu1—O1—C13	−73.23 (10)	C6—C7—C8—C12	0.9 (2)
O1—Cu1—N1—C2	13.31 (14)	C6—C7—C8—C9	−177.91 (16)
N2—Cu1—N1—C2	−177.92 (14)	C12—C8—C9—C10	1.0 (2)
O1W—Cu1—N1—C2	−81.72 (14)	C7—C8—C9—C10	179.83 (16)
O1—Cu1—N1—C1	−169.68 (10)	C8—C9—C10—C11	0.2 (3)
N2—Cu1—N1—C1	−0.91 (10)	C12—N2—C11—C10	0.7 (2)
O1W—Cu1—N1—C1	95.29 (10)	Cu1—N2—C11—C10	−175.89 (12)
O1—Cu1—N2—C11	−117.8 (2)	C9—C10—C11—N2	−1.1 (3)
N3—Cu1—N2—C11	−8.41 (14)	C11—N2—C12—C8	0.6 (2)
N1—Cu1—N2—C11	178.06 (14)	Cu1—N2—C12—C8	177.78 (11)
O1W—Cu1—N2—C11	82.79 (13)	C11—N2—C12—C1	−178.71 (13)
O1—Cu1—N2—C12	65.5 (2)	Cu1—N2—C12—C1	−1.56 (15)
N3—Cu1—N2—C12	174.87 (9)	C9—C8—C12—N2	−1.4 (2)
N1—Cu1—N2—C12	1.34 (9)	C7—C8—C12—N2	179.62 (14)
O1W—Cu1—N2—C12	−93.92 (10)	C9—C8—C12—C1	177.88 (14)
O1—Cu1—N3—C14	−25.06 (9)	C7—C8—C12—C1	−1.1 (2)
N2—Cu1—N3—C14	166.76 (9)	N1—C1—C12—N2	0.85 (19)
O1W—Cu1—N3—C14	69.72 (9)	C5—C1—C12—N2	179.55 (13)
C2—N1—C1—C5	−1.0 (2)	N1—C1—C12—C8	−178.52 (13)
Cu1—N1—C1—C5	−178.33 (11)	C5—C1—C12—C8	0.2 (2)
C2—N1—C1—C12	177.68 (13)	Cu1—O1—C13—O2	174.42 (13)
Cu1—N1—C1—C12	0.33 (16)	Cu1—O1—C13—C14	−2.72 (16)
C1—N1—C2—C3	0.7 (2)	Cu1—N3—C14—C15	155.66 (11)
Cu1—N1—C2—C3	177.57 (12)	Cu1—N3—C14—C13	28.94 (13)
N1—C2—C3—C4	0.2 (3)	O2—C13—C14—N3	164.17 (14)
C2—C3—C4—C5	−0.8 (3)	O1—C13—C14—N3	−18.54 (18)
N1—C1—C5—C4	0.4 (2)	O2—C13—C14—C15	36.5 (2)
C12—C1—C5—C4	−178.26 (14)	O1—C13—C14—C15	−146.24 (14)
N1—C1—C5—C6	179.43 (14)	N3—C14—C15—O3	−55.86 (17)
C12—C1—C5—C6	0.8 (2)	C13—C14—C15—O3	69.36 (16)
C3—C4—C5—C1	0.6 (2)	N3—C14—C15—C16	63.86 (19)
C3—C4—C5—C6	−178.46 (16)	C13—C14—C15—C16	−170.93 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···Cl1	0.80	2.36	3.1411 (13)	166
O1W—H2W1···O2i	0.82	1.90	2.7114 (18)	167
O3—H1O3···O1ii	0.90	2.03	2.9089 (18)	164
N3—H1N3···Cl1iii	0.86	2.62	3.3992 (13)	151
N3—H2N3···O2Wi	0.94	2.07	3.0085 (19)	175
O2W—H1W2···Cl1i	0.87	2.35	3.2104 (16)	175
O2W—H2W2···Cl1iv	0.84	2.33	3.1463 (14)	162
O3W—H1W3···O2W	1.01	1.95	2.954 (2)	170
O3W—H2W3···O3ii	0.91	2.03	2.901 (2)	159
C7—H7A···O2v	0.93	2.41	3.292 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯Cl1	0.80	2.36	3.1411 (13)	166
O1W—H2W1⋯O2i	0.82	1.90	2.7114 (18)	167
O3—H1O3⋯O1ii	0.90	2.03	2.9089 (18)	164
N3—H1N3⋯Cl1iii	0.86	2.62	3.3992 (13)	151
N3—H2N3⋯O2Wi	0.94	2.07	3.0085 (19)	175
O2W—H1W2⋯Cl1i	0.87	2.35	3.2104 (16)	175
O2W—H2W2⋯Cl1iv	0.84	2.33	3.1463 (14)	162
O3W—H1W3⋯O2W	1.01	1.95	2.954 (2)	170
O3W—H2W3⋯O3ii	0.91	2.03	2.901 (2)	159
C7—H7A⋯O2v	0.93	2.41	3.292 (2)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .