(2-Amino-7-methyl-4-oxidopteridine-6-carboxyl-ato-κ(3) O (4),N (5),O (6))(ethane-1,2-diamine-κ(2) N,N')(1H-imidazole-κN (3))nickel(II) dihydrate.

In the title complex, [Ni(C8H5N5O3)(C2H8N2)(C3N2H4)]·2H2O, a tridentate 2-amino-7-methyl-4-oxidopteridine-6-carboxyl-ate (pterin) ligand, a bidentate ancillary ethane-1,2-diamine (en) ligand and a monodentate 1H-imidazole (im) ligand complete a distorted octa-hedral geometry around the Ni(II) atom. The pterin ligand forms two chelate rings. Both the en and im ligands are arranged nearly orthogonally relative to the pterin ligand [dihedral angles between the mean planes of the en and pterin ligands and of the im and pterin ligands are 84.62 (9) and 85.14 (9)°, respectively]. N-H⋯N, N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds link the complex mol-ecules and lattice water mol-ecules into a three-dimensional network.

Related literature

For the importance of pterin in metalloenzymes, see: Basu & Burgmayer (2011 ▶); Burgmayer (1998 ▶); Fitzpatrick (2003 ▶); Fukuzumi & Kojima (2008 ▶); Kaim et al. (1999 ▶). For the structures of related nickel complexes, see: Baisya & Roy (2013 ▶); Crispini et al. (2005 ▶). For the structures of related copper complexes, see: Odani et al. (1992 ▶). For the electron-shuffling ability of the pterin unit as well as its donor groups and the effect on the geometric parameters of related complexes, see: Beddoes et al. (1993 ▶); Kohzuma et al. (1988 ▶); Russell et al. (1992 ▶). For the synthesis of the pterin ligand, see: Wittle et al. (1947 ▶). For refinement of H atoms, see: Cooper et al. (2010 ▶).

Experimental

Crystal data

[Ni(C8H5N5O3)(C2H8N2)(C3H4N2)]·2H2O

M = 442.08

Orthorhombic,

a = 13.484 (2) Å

b = 8.8741 (15) Å

c = 29.959 (5) Å

V = 3584.9 (10) Å3

Z = 8

Mo Kα radiation

μ = 1.13 mm−1

T = 293 K

0.24 × 0.24 × 0.03 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.77, T max = 0.97

19640 measured reflections

4231 independent reflections

3521 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.091

S = 0.95

4231 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005898/hy2617sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005898/hy2617Isup2.hkl

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

[Ni(C8H5N5O3)(C2H8N2)(C3H4N2)]·2H2O	F(000) = 1840
Mr = 442.08	Dx = 1.638 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4231 reflections
a = 13.484 (2) Å	θ = 1.4–28.3°
b = 8.8741 (15) Å	µ = 1.13 mm−1
c = 29.959 (5) Å	T = 293 K
V = 3584.9 (10) Å3	Plate, orange
Z = 8	0.24 × 0.24 × 0.03 mm

Bruker Kappa APEXII CCD diffractometer	3521 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.77, Tmax = 0.97	k = −11→11
19640 measured reflections	l = −24→38
4231 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.091	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.04P)2 + 3.53P], where P = [max(Fo2,0) + 2Fc2]/3
S = 0.95	(Δ/σ)max = 0.001
4231 reflections	Δρmax = 0.62 e Å−3
253 parameters	Δρmin = −0.32 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
Ni1	0.461327 (17)	0.49322 (3)	0.372395 (8)	0.0275
O1	0.54402 (10)	0.60856 (16)	0.32134 (5)	0.0335
C1	0.63525 (15)	0.5742 (2)	0.31846 (6)	0.0292
O2	0.69402 (11)	0.62442 (18)	0.29021 (5)	0.0423
C2	0.67092 (14)	0.4597 (2)	0.35277 (6)	0.0262
N1	0.59680 (11)	0.40936 (17)	0.37761 (5)	0.0254
C7	0.61252 (13)	0.3066 (2)	0.40867 (6)	0.0252
C4	0.70658 (13)	0.2460 (2)	0.41611 (6)	0.0246
N2	0.78491 (11)	0.29914 (18)	0.39231 (5)	0.0286
C3	0.76772 (14)	0.4043 (2)	0.36124 (6)	0.0273
C8	0.85670 (16)	0.4622 (2)	0.33676 (8)	0.0407
H111	0.9180	0.4284	0.3494	0.0629*
H113	0.8523	0.4298	0.3069	0.0630*
H112	0.8565	0.5676	0.3363	0.0619*
N3	0.71925 (12)	0.13478 (18)	0.44623 (5)	0.0293
C5	0.63537 (14)	0.0864 (2)	0.46626 (6)	0.0297
N4	0.54093 (12)	0.14309 (19)	0.46268 (5)	0.0312
C6	0.52732 (13)	0.2575 (2)	0.43450 (6)	0.0268
O3	0.44423 (10)	0.32158 (16)	0.42815 (5)	0.0329
N5	0.64372 (14)	−0.0319 (2)	0.49338 (6)	0.0414
H172	0.5918	−0.0634	0.5068	0.0504*
H171	0.7003	−0.0668	0.4983	0.0503*
N6	0.32580 (14)	0.6051 (2)	0.36971 (7)	0.0478
C9	0.3190 (2)	0.7106 (3)	0.40720 (9)	0.0610
C10	0.4178 (2)	0.7830 (3)	0.41328 (10)	0.0556
N7	0.49397 (14)	0.66577 (19)	0.41780 (6)	0.0367
H211	0.5548	0.7039	0.4136	0.0564*
H212	0.4950	0.6335	0.4452	0.0559*
H202	0.4167	0.8476	0.4384	0.0688*
H201	0.4317	0.8402	0.3867	0.0695*
H192	0.2669	0.7839	0.4035	0.0736*
H191	0.3043	0.6540	0.4352	0.0746*
H181	0.2742	0.5434	0.3674	0.0732*
H182	0.3228	0.6546	0.3442	0.0727*
N8	0.41434 (14)	0.3313 (2)	0.32768 (6)	0.0383
C11	0.41880 (17)	0.1814 (2)	0.33182 (8)	0.0416
N9	0.38881 (18)	0.1135 (3)	0.29413 (9)	0.0652
C12	0.3599 (3)	0.2243 (3)	0.26639 (9)	0.0699
C13	0.3786 (3)	0.3547 (3)	0.28659 (9)	0.0733
H261	0.3671	0.4468	0.2743	0.0892*
H251	0.3344	0.2134	0.2406	0.0848*
H241	0.3806	0.0153	0.2892	0.0825*
H231	0.4395	0.1296	0.3568	0.0527*
O4	0.37876 (13)	0.4892 (2)	0.50415 (6)	0.0543
H271	0.3379	0.4436	0.5195	0.0824*
H272	0.3890	0.4340	0.4833	0.0825*
O5	0.38933 (16)	0.7745 (2)	0.28388 (6)	0.0685
H281	0.3645	0.7400	0.2605	0.1040*
H282	0.4446	0.7401	0.2817	0.1049*

	U11	U22	U33	U12	U13	U23
Ni1	0.02605 (14)	0.02545 (14)	0.03107 (14)	0.00016 (9)	−0.00317 (9)	0.00076 (9)
O1	0.0339 (7)	0.0321 (7)	0.0344 (7)	−0.0011 (6)	−0.0042 (6)	0.0073 (6)
C1	0.0361 (10)	0.0262 (9)	0.0253 (9)	−0.0028 (8)	−0.0023 (7)	0.0001 (7)
O2	0.0456 (9)	0.0479 (9)	0.0334 (7)	−0.0033 (7)	0.0059 (6)	0.0132 (7)
C2	0.0310 (9)	0.0226 (8)	0.0250 (8)	−0.0023 (7)	0.0013 (7)	−0.0009 (7)
N1	0.0259 (7)	0.0252 (8)	0.0250 (7)	0.0000 (6)	−0.0009 (6)	0.0005 (6)
C7	0.0274 (9)	0.0237 (8)	0.0245 (8)	−0.0002 (7)	0.0010 (7)	−0.0007 (7)
C4	0.0271 (9)	0.0238 (8)	0.0228 (8)	−0.0001 (7)	0.0000 (7)	−0.0030 (7)
N2	0.0280 (8)	0.0257 (8)	0.0320 (8)	0.0009 (6)	0.0034 (6)	−0.0004 (6)
C3	0.0297 (10)	0.0236 (8)	0.0286 (9)	−0.0025 (7)	0.0039 (7)	−0.0027 (7)
C8	0.0323 (10)	0.0358 (11)	0.0541 (13)	0.0004 (9)	0.0119 (9)	0.0109 (10)
N3	0.0282 (8)	0.0304 (8)	0.0293 (8)	0.0033 (6)	0.0010 (6)	0.0046 (6)
C5	0.0340 (10)	0.0275 (9)	0.0275 (9)	0.0017 (8)	0.0013 (7)	0.0023 (7)
N4	0.0290 (8)	0.0321 (8)	0.0324 (8)	−0.0002 (6)	0.0042 (6)	0.0064 (7)
C6	0.0263 (9)	0.0281 (9)	0.0258 (8)	−0.0016 (7)	0.0007 (7)	−0.0003 (7)
O3	0.0255 (6)	0.0372 (7)	0.0359 (7)	0.0023 (6)	0.0030 (5)	0.0058 (6)
N5	0.0376 (10)	0.0412 (10)	0.0454 (10)	0.0058 (8)	0.0078 (8)	0.0188 (8)
N6	0.0336 (10)	0.0475 (11)	0.0624 (13)	0.0043 (8)	−0.0076 (9)	0.0034 (9)
C9	0.0523 (15)	0.0690 (18)	0.0617 (16)	0.0258 (14)	0.0095 (13)	0.0033 (14)
C10	0.0660 (17)	0.0399 (13)	0.0610 (16)	0.0132 (12)	−0.0007 (13)	−0.0132 (11)
N7	0.0413 (10)	0.0360 (9)	0.0329 (9)	−0.0008 (8)	−0.0013 (7)	−0.0027 (7)
N8	0.0422 (10)	0.0324 (9)	0.0402 (9)	−0.0059 (8)	−0.0084 (8)	−0.0020 (7)
C11	0.0428 (12)	0.0323 (11)	0.0498 (13)	−0.0009 (9)	−0.0073 (10)	−0.0025 (9)
N9	0.0756 (16)	0.0430 (12)	0.0769 (16)	−0.0070 (11)	−0.0090 (13)	−0.0200 (11)
C12	0.112 (3)	0.0476 (15)	0.0503 (15)	−0.0073 (16)	−0.0420 (16)	−0.0115 (12)
C13	0.122 (3)	0.0437 (14)	0.0544 (16)	−0.0051 (16)	−0.0438 (17)	0.0012 (12)
O4	0.0545 (10)	0.0558 (11)	0.0525 (10)	−0.0125 (8)	0.0175 (8)	−0.0034 (8)
O5	0.0879 (14)	0.0667 (12)	0.0509 (10)	0.0327 (11)	−0.0241 (10)	−0.0153 (9)

Ni1—O1	2.1519 (14)	N5—H172	0.853
Ni1—N1	1.9787 (16)	N5—H171	0.837
Ni1—O3	2.2722 (14)	N6—C9	1.465 (3)
Ni1—N6	2.0812 (19)	N6—H181	0.888
Ni1—N7	2.0949 (17)	N6—H182	0.881
Ni1—N8	2.0638 (17)	C9—C10	1.491 (4)
O1—C1	1.270 (2)	C9—H192	0.964
C1—O2	1.242 (2)	C9—H191	0.997
C1—C2	1.523 (3)	C10—N7	1.468 (3)
C2—N1	1.324 (2)	C10—H202	0.945
C2—C3	1.418 (3)	C10—H201	0.962
N1—C7	1.320 (2)	N7—H211	0.896
C7—C4	1.395 (2)	N7—H212	0.869
C7—C6	1.452 (2)	N8—C11	1.338 (3)
C4—N2	1.359 (2)	N8—C13	1.338 (3)
C4—N3	1.348 (2)	C11—N9	1.342 (3)
N2—C3	1.338 (2)	C11—H231	0.922
C3—C8	1.497 (3)	N9—C12	1.346 (4)
C8—H111	0.957	N9—H241	0.890
C8—H113	0.940	C12—C13	1.329 (4)
C8—H112	0.936	C12—H251	0.850
N3—C5	1.351 (2)	C13—H261	0.910
C5—N4	1.373 (2)	O4—H271	0.825
C5—N5	1.332 (2)	O4—H272	0.807
N4—C6	1.333 (2)	O5—H281	0.834
C6—O3	1.271 (2)	O5—H282	0.808
O1—Ni1—N1	75.91 (6)	C7—C6—O3	118.92 (16)
O1—Ni1—O3	153.37 (5)	N4—C6—O3	123.85 (16)
N1—Ni1—O3	77.50 (6)	Ni1—O3—C6	108.69 (11)
O1—Ni1—N6	101.58 (7)	C5—N5—H172	118.4
N1—Ni1—N6	173.26 (7)	C5—N5—H171	118.4
O3—Ni1—N6	105.01 (7)	H172—N5—H171	122.9
O1—Ni1—N7	90.29 (6)	Ni1—N6—C9	109.29 (15)
N1—Ni1—N7	91.70 (7)	Ni1—N6—H181	113.4
O3—Ni1—N7	91.95 (6)	C9—N6—H181	113.8
N6—Ni1—N7	82.01 (8)	Ni1—N6—H182	108.1
O1—Ni1—N8	91.65 (7)	C9—N6—H182	110.0
N1—Ni1—N8	94.18 (7)	H181—N6—H182	101.8
O3—Ni1—N8	88.82 (7)	N6—C9—C10	108.2 (2)
N6—Ni1—N8	92.13 (8)	N6—C9—H192	112.9
N7—Ni1—N8	174.10 (7)	C10—C9—H192	112.0
Ni1—O1—C1	115.85 (12)	N6—C9—H191	109.6
O1—C1—O2	125.32 (18)	C10—C9—H191	107.0
O1—C1—C2	114.83 (16)	H192—C9—H191	107.0
O2—C1—C2	119.84 (17)	C9—C10—N7	109.3 (2)
C1—C2—N1	111.47 (16)	C9—C10—H202	110.1
C1—C2—C3	130.01 (16)	N7—C10—H202	111.5
N1—C2—C3	118.51 (16)	C9—C10—H201	107.5
C2—N1—Ni1	121.72 (13)	N7—C10—H201	108.3
C2—N1—C7	120.55 (16)	H202—C10—H201	110.0
Ni1—N1—C7	117.63 (12)	C10—N7—Ni1	108.13 (14)
N1—C7—C4	121.65 (16)	C10—N7—H211	111.1
N1—C7—C6	117.12 (16)	Ni1—N7—H211	112.2
C4—C7—C6	121.23 (16)	C10—N7—H212	109.4
C7—C4—N2	119.28 (16)	Ni1—N7—H212	112.0
C7—C4—N3	120.28 (16)	H211—N7—H212	104.0
N2—C4—N3	120.44 (16)	Ni1—N8—C11	128.20 (15)
C4—N2—C3	118.19 (16)	Ni1—N8—C13	126.88 (17)
C2—C3—N2	121.72 (16)	C11—N8—C13	104.8 (2)
C2—C3—C8	122.07 (17)	N8—C11—N9	110.8 (2)
N2—C3—C8	116.19 (17)	N8—C11—H231	125.8
C3—C8—H111	113.0	N9—C11—H231	123.4
C3—C8—H113	108.0	C11—N9—C12	106.2 (2)
H111—C8—H113	109.6	C11—N9—H241	128.0
C3—C8—H112	110.4	C12—N9—H241	125.3
H111—C8—H112	108.7	N9—C12—C13	107.5 (2)
H113—C8—H112	107.0	N9—C12—H251	126.4
C4—N3—C5	115.09 (15)	C13—C12—H251	126.1
N3—C5—N4	128.71 (17)	N8—C13—C12	110.6 (2)
N3—C5—N5	116.80 (17)	N8—C13—H261	124.9
N4—C5—N5	114.49 (17)	C12—C13—H261	124.4
C5—N4—C6	117.14 (16)	H271—O4—H272	104.5
C7—C6—N4	117.19 (16)	H281—O5—H282	99.5

D—H···A	D—H	H···A	D···A	D—H···A
N5—H171···O4i	0.84	2.50	3.193 (3)	140
N5—H172···N4ii	0.85	2.13	2.984 (3)	177
N6—H182···O5	0.88	2.28	3.099 (3)	154
N7—H211···N2iii	0.90	2.41	3.298 (2)	173
N7—H212···O4iv	0.87	2.53	3.210 (3)	136
N9—H241···O5v	0.89	2.15	3.024 (3)	168
O4—H271···N3vi	0.82	2.02	2.837 (2)	169
O4—H272···O3	0.81	2.07	2.859 (2)	167
O5—H281···O2vii	0.83	2.00	2.822 (2)	170
O5—H282···O1	0.81	2.14	2.789 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H171⋯O4i	0.84	2.50	3.193 (3)	140
N5—H172⋯N4ii	0.85	2.13	2.984 (3)	177
N6—H182⋯O5	0.88	2.28	3.099 (3)	154
N7—H211⋯N2iii	0.90	2.41	3.298 (2)	173
N7—H212⋯O4iv	0.87	2.53	3.210 (3)	136
N9—H241⋯O5v	0.89	2.15	3.024 (3)	168
O4—H271⋯N3vi	0.82	2.02	2.837 (2)	169
O4—H272⋯O3	0.81	2.07	2.859 (2)	167
O5—H281⋯O2vii	0.83	2.00	2.822 (2)	170
O5—H282⋯O1	0.81	2.14	2.789 (2)	138

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