Aqua­(imino­diacetato-κ3O,N,O′)(1,10-phenanthroline-κ2N,N′)cobalt(II) monohydrate

Ng, H.L.; Ng, C.H.; Ng, S.W.

doi:10.1107/S1600536808041226

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m41

doi:10.1107/S1600536808041226

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Aqua(iminodiacetato-κ³O,N,O′)(1,10-phenanthroline-κ²N,N′)cobalt(II) monohydrate

Hwa Loong Ng,^a Chew Hee Ng ^a and Seik Weng Ng ^b ^*

^aFaculty of Engineering & Science, Universiti Tunku Abdul Rahman, Jalan Genting Kelang, 53100 Kuala Lumpur, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 3 December 2008; accepted 6 December 2008; online 10 December 2008)

The iminodiacetate dianion in the title compound, [Co(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·H₂O, chelates to the cobalt(II) atom, its N and two O atoms occupying the fac sites of the distorted octahedron around the metal atom. The metal atom is also chelated by the N-heterocycle. The dianion, and coordinated and uncoordinated water molecules interact through hydrogen bonds, generating a layer motif. The crystal studied was a racemic twin with a 0.62 (2):0.38 (2) domain ratio.

Related literature

For structural examples of the N-heterocycle adducts of cobalt iminodiacetate, see: Su & Xu (2004 ); Xu et al. (1989 ).

Experimental

Crystal data

[Co(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·H₂O
M_r = 406.26
Monoclinic, P n
a = 6.7884 (3) Å
b = 12.0903 (5) Å
c = 10.4945 (4) Å
β = 108.357 (3)°
V = 817.49 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 100 (2) K
0.35 × 0.02 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.701, T_max = 0.979
6417 measured reflections
3639 independent reflections
2997 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.126
S = 1.00
3639 reflections
248 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.49 e Å⁻³
Absolute structure: Flack (1983 ), 1746 Friedel pairs
Flack parameter: 0.38 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O2ⁱ	0.84 (5)	1.82 (4)	2.656 (5)	174 (6)
O1w—H12⋯O4ⁱⁱ	0.84 (6)	1.87 (4)	2.682 (5)	162 (6)
O2w—H21⋯O1ⁱ	0.84 (5)	1.98 (4)	2.815 (5)	174 (7)
O2w—H22⋯O4	0.84 (6)	2.05 (5)	2.871 (5)	165 (6)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ .

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: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041226/sj2563sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041226/sj2563Isup2.hkl

checkCIF report

Related literature top

For structural examples of the N-heterocycle adducts of cobalt iminodiacetate, see: Su & Xu (2004); Xu et al. (1989).

Experimental top

An aqueous solution of cobalt(II) chloride (0.24 g, 1 mmol) was mixed with an aqueous solutin of disodium iminodiacetate monohydrate (0.20 g, 1 mmol); this was added to a water-methanol solution of 1,10-phenanthroline (0.20 g, 1 mmol). The solution was set aside for the growth of orange crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: pubCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Co(C₁₂H₈N₂)(C₄H₅NO₄)(H₂O)^.H₂O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Aqua(iminodiacetato-κ³O,N,O')(1,10- phenanthroline-κ²N,N')cobalt(II) monohydrate top

Crystal data top

[Co(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·H₂O	F(000) = 418
M_r = 406.26	D_x = 1.650 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yac	Cell parameters from 1265 reflections
a = 6.7884 (3) Å	θ = 2.6–24.5°
b = 12.0903 (5) Å	µ = 1.09 mm⁻¹
c = 10.4945 (4) Å	T = 100 K
β = 108.357 (3)°	Prism, orange
V = 817.49 (6) Å³	0.35 × 0.02 × 0.02 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	3639 independent reflections
Radiation source: fine-focus sealed tube	2997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.701, T_max = 0.979	k = −15→15
6417 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0697P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3639 reflections	Δρ_max = 0.86 e Å⁻³
248 parameters	Δρ_min = −0.49 e Å⁻³
8 restraints	Absolute structure: Flack (1983), 1746 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.38 (2)

Crystal data top

[Co(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·H₂O	V = 817.49 (6) Å³
M_r = 406.26	Z = 2
Monoclinic, Pn	Mo Kα radiation
a = 6.7884 (3) Å	µ = 1.09 mm⁻¹
b = 12.0903 (5) Å	T = 100 K
c = 10.4945 (4) Å	0.35 × 0.02 × 0.02 mm
β = 108.357 (3)°

Data collection top

Bruker SMART APEX diffractometer	3639 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2997 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.979	R_int = 0.048
6417 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	Δρ_max = 0.86 e Å⁻³
S = 1.00	Δρ_min = −0.49 e Å⁻³
3639 reflections	Absolute structure: Flack (1983), 1746 Friedel pairs
248 parameters	Absolute structure parameter: 0.38 (2)
8 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.49999 (10)	0.85733 (5)	0.50000 (8)	0.01527 (16)
O1	0.4183 (7)	0.8730 (3)	0.6730 (4)	0.0222 (9)
O2	0.3360 (6)	1.0019 (3)	0.7965 (4)	0.0254 (8)
O3	0.7258 (6)	0.9787 (3)	0.5790 (3)	0.0196 (9)
O4	0.7806 (5)	1.1607 (3)	0.5786 (3)	0.0190 (7)
O1W	0.5702 (6)	0.8446 (3)	0.3211 (4)	0.0194 (9)
H11	0.652 (7)	0.896 (3)	0.317 (5)	0.029*
H12	0.493 (7)	0.830 (4)	0.243 (2)	0.029*
O2W	0.9365 (7)	1.2706 (3)	0.3875 (4)	0.0307 (9)
H21	0.939 (10)	1.225 (4)	0.327 (4)	0.046*
H22	0.870 (9)	1.243 (4)	0.435 (5)	0.046*
N1	0.3129 (7)	1.0058 (4)	0.4480 (4)	0.0162 (10)
H1	0.2104	0.9968	0.3727	0.019*
N2	0.6902 (8)	0.7165 (4)	0.5733 (5)	0.0171 (10)
N3	0.2824 (7)	0.7278 (4)	0.4343 (4)	0.0168 (11)
C1	0.3389 (7)	0.9654 (4)	0.6867 (5)	0.0193 (10)
C2	0.2335 (7)	1.0313 (4)	0.5604 (5)	0.0202 (10)
H2A	0.0826	1.0160	0.5320	0.024*
H2B	0.2533	1.1112	0.5814	0.024*
C3	0.4607 (8)	1.0907 (4)	0.4324 (5)	0.0183 (10)
H3A	0.4062	1.1653	0.4414	0.022*
H3B	0.4760	1.0849	0.3419	0.022*
C4	0.6704 (8)	1.0754 (4)	0.5382 (5)	0.0177 (10)
C5	0.8890 (9)	0.7128 (5)	0.6410 (5)	0.0217 (13)
H5	0.9625	0.7806	0.6638	0.026*
C6	0.9974 (10)	0.6143 (5)	0.6811 (6)	0.0256 (13)
H6	1.1410	0.6154	0.7310	0.031*
C7	0.8948 (9)	0.5164 (5)	0.6478 (5)	0.0246 (13)
H7	0.9666	0.4485	0.6736	0.030*
C8	0.6812 (10)	0.5167 (5)	0.5748 (5)	0.0221 (13)
C9	0.5835 (10)	0.6199 (5)	0.5401 (7)	0.0210 (14)
C10	0.5597 (10)	0.4182 (5)	0.5380 (6)	0.0269 (14)
H10	0.6247	0.3481	0.5601	0.032*
C11	0.3534 (10)	0.4234 (4)	0.4720 (6)	0.0230 (12)
H11A	0.2754	0.3570	0.4500	0.028*
C12	0.2518 (10)	0.5267 (5)	0.4351 (5)	0.0205 (13)
C13	0.3668 (10)	0.6250 (4)	0.4676 (6)	0.0128 (12)
C14	0.0390 (9)	0.5374 (4)	0.3682 (5)	0.0220 (12)
H14	−0.0462	0.4734	0.3459	0.026*
C15	−0.0462 (10)	0.6399 (4)	0.3350 (6)	0.0238 (14)
H15	−0.1902	0.6475	0.2884	0.029*
C16	0.0795 (8)	0.7328 (5)	0.3699 (6)	0.0182 (11)
H16	0.0175	0.8035	0.3467	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0158 (3)	0.0120 (3)	0.0173 (3)	0.0003 (3)	0.0041 (2)	−0.0001 (3)
O1	0.033 (3)	0.0132 (18)	0.024 (2)	0.0052 (16)	0.0135 (19)	0.0029 (14)
O2	0.0220 (19)	0.032 (2)	0.0207 (17)	0.0070 (16)	0.0052 (14)	−0.0024 (16)
O3	0.017 (2)	0.0178 (19)	0.021 (2)	0.0012 (15)	0.0013 (16)	0.0033 (15)
O4	0.0219 (18)	0.0127 (17)	0.0210 (17)	−0.0021 (14)	0.0048 (14)	0.0012 (13)
O1W	0.014 (2)	0.023 (2)	0.0183 (19)	−0.0049 (15)	0.0022 (16)	0.0039 (15)
O2W	0.049 (3)	0.0175 (19)	0.029 (2)	−0.0081 (18)	0.0165 (19)	−0.0030 (15)
N1	0.010 (2)	0.022 (3)	0.012 (2)	−0.0009 (18)	−0.0025 (17)	0.0020 (19)
N2	0.019 (2)	0.011 (2)	0.022 (2)	0.0010 (19)	0.0077 (19)	−0.0011 (19)
N3	0.021 (2)	0.015 (2)	0.014 (2)	0.0008 (19)	0.0053 (19)	−0.0012 (18)
C1	0.012 (2)	0.027 (3)	0.017 (2)	0.001 (2)	0.0017 (19)	−0.001 (2)
C2	0.015 (2)	0.021 (2)	0.025 (3)	0.0072 (19)	0.008 (2)	0.003 (2)
C3	0.017 (3)	0.013 (2)	0.022 (2)	−0.002 (2)	0.002 (2)	0.0032 (19)
C4	0.020 (3)	0.016 (3)	0.017 (2)	0.001 (2)	0.007 (2)	0.001 (2)
C5	0.019 (3)	0.026 (3)	0.018 (3)	0.002 (2)	0.003 (2)	−0.004 (2)
C6	0.017 (3)	0.034 (3)	0.022 (3)	0.008 (3)	0.002 (2)	0.004 (2)
C7	0.027 (3)	0.021 (3)	0.026 (3)	0.012 (2)	0.008 (2)	0.008 (2)
C8	0.027 (3)	0.020 (3)	0.023 (3)	0.004 (2)	0.013 (2)	0.007 (2)
C9	0.023 (3)	0.018 (3)	0.024 (3)	0.001 (2)	0.009 (2)	0.000 (2)
C10	0.041 (4)	0.011 (2)	0.033 (3)	0.004 (2)	0.017 (3)	0.002 (2)
C11	0.029 (3)	0.013 (2)	0.030 (3)	−0.001 (2)	0.014 (2)	0.001 (2)
C12	0.029 (3)	0.015 (3)	0.022 (3)	−0.004 (2)	0.013 (3)	0.000 (2)
C13	0.016 (3)	0.010 (3)	0.013 (2)	0.003 (2)	0.006 (2)	0.0001 (19)
C14	0.019 (3)	0.019 (3)	0.027 (3)	−0.007 (2)	0.006 (2)	−0.002 (2)
C15	0.019 (3)	0.025 (3)	0.027 (3)	−0.005 (2)	0.006 (2)	−0.003 (2)
C16	0.012 (2)	0.016 (3)	0.023 (3)	0.003 (2)	0.001 (2)	−0.003 (2)

Geometric parameters (Å, º) top

Co1—O1	2.067 (4)	C3—C4	1.516 (7)
Co1—O1W	2.083 (4)	C3—H3A	0.9900
Co1—O3	2.095 (4)	C3—H3B	0.9900
Co1—N3	2.113 (5)	C5—C6	1.394 (8)
Co1—N2	2.129 (5)	C5—H5	0.9500
Co1—N1	2.167 (5)	C6—C7	1.362 (8)
O1—C1	1.269 (6)	C6—H6	0.9500
O2—C1	1.240 (6)	C7—C8	1.411 (8)
O3—C4	1.260 (6)	C7—H7	0.9500
O4—C4	1.267 (6)	C8—C9	1.406 (9)
O1W—H11	0.84 (5)	C8—C10	1.430 (8)
O1W—H12	0.84 (6)	C9—C13	1.429 (8)
O2W—H21	0.84 (5)	C10—C11	1.355 (9)
O2W—H22	0.84 (6)	C10—H10	0.9500
N1—C2	1.476 (6)	C11—C12	1.420 (8)
N1—C3	1.480 (6)	C11—H11A	0.9500
N1—H1	0.8800	C12—C14	1.399 (9)
N2—C5	1.313 (8)	C12—C13	1.403 (8)
N2—C9	1.360 (8)	C14—C15	1.365 (8)
N3—C16	1.331 (7)	C14—H14	0.9500
N3—C13	1.368 (7)	C15—C16	1.389 (8)
C1—C2	1.518 (6)	C15—H15	0.9500
C2—H2A	0.9900	C16—H16	0.9500
C2—H2B	0.9900

O1—Co1—O1W	177.6 (2)	C4—C3—H3A	109.6
O1—Co1—O3	87.34 (16)	N1—C3—H3B	109.6
O1W—Co1—O3	93.54 (15)	C4—C3—H3B	109.6
O1—Co1—N3	90.07 (17)	H3A—C3—H3B	108.1
O1W—Co1—N3	89.20 (16)	O3—C4—O4	124.0 (5)
O3—Co1—N3	175.53 (17)	O3—C4—C3	118.3 (5)
O1—Co1—N2	93.20 (16)	O4—C4—C3	117.7 (4)
O1W—Co1—N2	88.95 (17)	N2—C5—C6	123.2 (6)
O3—Co1—N2	97.62 (17)	N2—C5—H5	118.4
N3—Co1—N2	78.88 (15)	C6—C5—H5	118.4
O1—Co1—N1	81.23 (15)	C7—C6—C5	119.1 (6)
O1W—Co1—N1	96.68 (15)	C7—C6—H6	120.4
O3—Co1—N1	79.47 (17)	C5—C6—H6	120.4
N3—Co1—N1	103.74 (19)	C6—C7—C8	119.5 (5)
N2—Co1—N1	173.79 (18)	C6—C7—H7	120.2
C1—O1—Co1	114.9 (3)	C8—C7—H7	120.2
C4—O3—Co1	114.3 (3)	C9—C8—C7	117.5 (5)
Co1—O1W—H11	109 (3)	C9—C8—C10	119.0 (5)
Co1—O1W—H12	130 (3)	C7—C8—C10	123.5 (5)
H11—O1W—H12	109 (5)	N2—C9—C8	121.7 (6)
H21—O2W—H22	109 (5)	N2—C9—C13	118.4 (6)
C2—N1—C3	111.9 (4)	C8—C9—C13	119.9 (6)
C2—N1—Co1	107.7 (3)	C11—C10—C8	121.0 (5)
C3—N1—Co1	103.8 (3)	C11—C10—H10	119.5
C2—N1—H1	111.0	C8—C10—H10	119.5
C3—N1—H1	111.0	C10—C11—C12	121.0 (6)
Co1—N1—H1	111.0	C10—C11—H11A	119.5
C5—N2—C9	118.9 (5)	C12—C11—H11A	119.5
C5—N2—Co1	128.7 (4)	C14—C12—C13	116.9 (5)
C9—N2—Co1	112.4 (4)	C14—C12—C11	123.6 (5)
C16—N3—C13	117.0 (5)	C13—C12—C11	119.5 (6)
C16—N3—Co1	129.6 (4)	N3—C13—C12	123.5 (6)
C13—N3—Co1	113.4 (4)	N3—C13—C9	116.9 (6)
O2—C1—O1	123.4 (5)	C12—C13—C9	119.6 (6)
O2—C1—C2	118.9 (4)	C15—C14—C12	119.9 (5)
O1—C1—C2	117.6 (4)	C15—C14—H14	120.0
N1—C2—C1	113.4 (4)	C12—C14—H14	120.0
N1—C2—H2A	108.9	C14—C15—C16	119.5 (6)
C1—C2—H2A	108.9	C14—C15—H15	120.3
N1—C2—H2B	108.9	C16—C15—H15	120.3
C1—C2—H2B	108.9	N3—C16—C15	123.3 (5)
H2A—C2—H2B	107.7	N3—C16—H16	118.4
N1—C3—C4	110.3 (4)	C15—C16—H16	118.4
N1—C3—H3A	109.6

O3—Co1—O1—C1	66.7 (4)	Co1—O3—C4—C3	−4.4 (6)
N3—Co1—O1—C1	−116.9 (4)	N1—C3—C4—O3	31.4 (6)
N2—Co1—O1—C1	164.2 (4)	N1—C3—C4—O4	−149.6 (4)
N1—Co1—O1—C1	−13.1 (4)	C9—N2—C5—C6	−0.1 (8)
O1—Co1—O3—C4	−96.3 (4)	Co1—N2—C5—C6	−178.6 (4)
O1W—Co1—O3—C4	81.5 (4)	N2—C5—C6—C7	0.8 (9)
N2—Co1—O3—C4	170.9 (3)	C5—C6—C7—C8	−0.6 (8)
N1—Co1—O3—C4	−14.7 (4)	C6—C7—C8—C9	−0.3 (8)
O1—Co1—N1—C2	−1.0 (3)	C6—C7—C8—C10	−178.6 (5)
O1W—Co1—N1—C2	177.7 (3)	C5—N2—C9—C8	−0.9 (8)
O3—Co1—N1—C2	−89.9 (3)	Co1—N2—C9—C8	177.9 (4)
N3—Co1—N1—C2	86.9 (3)	C5—N2—C9—C13	179.4 (5)
O1—Co1—N1—C3	117.8 (3)	Co1—N2—C9—C13	−1.9 (6)
O1W—Co1—N1—C3	−63.4 (3)	C7—C8—C9—N2	1.0 (8)
O3—Co1—N1—C3	28.9 (3)	C10—C8—C9—N2	179.4 (5)
N3—Co1—N1—C3	−154.3 (3)	C7—C8—C9—C13	−179.2 (5)
O1—Co1—N2—C5	−90.5 (5)	C10—C8—C9—C13	−0.8 (7)
O1W—Co1—N2—C5	90.7 (5)	C9—C8—C10—C11	−0.7 (8)
O3—Co1—N2—C5	−2.8 (5)	C7—C8—C10—C11	177.6 (5)
N3—Co1—N2—C5	−180.0 (5)	C8—C10—C11—C12	1.1 (8)
O1—Co1—N2—C9	90.9 (4)	C10—C11—C12—C14	−179.3 (5)
O1W—Co1—N2—C9	−88.0 (4)	C10—C11—C12—C13	0.0 (8)
O3—Co1—N2—C9	178.6 (4)	C16—N3—C13—C12	1.3 (8)
N3—Co1—N2—C9	1.4 (4)	Co1—N3—C13—C12	179.6 (4)
O1—Co1—N3—C16	84.0 (5)	C16—N3—C13—C9	−178.2 (5)
O1W—Co1—N3—C16	−93.7 (5)	Co1—N3—C13—C9	0.1 (6)
N2—Co1—N3—C16	177.2 (5)	C14—C12—C13—N3	−1.7 (8)
N1—Co1—N3—C16	3.0 (5)	C11—C12—C13—N3	179.0 (5)
O1—Co1—N3—C13	−94.1 (4)	C14—C12—C13—C9	177.8 (5)
O1W—Co1—N3—C13	88.3 (4)	C11—C12—C13—C9	−1.5 (7)
N2—Co1—N3—C13	−0.8 (4)	N2—C9—C13—N3	1.2 (7)
N1—Co1—N3—C13	−175.0 (3)	C8—C9—C13—N3	−178.5 (5)
Co1—O1—C1—O2	−158.4 (4)	N2—C9—C13—C12	−178.3 (5)
Co1—O1—C1—C2	24.6 (6)	C8—C9—C13—C12	1.9 (7)
C3—N1—C2—C1	−101.0 (5)	C13—C12—C14—C15	1.4 (8)
Co1—N1—C2—C1	12.5 (5)	C11—C12—C14—C15	−179.2 (5)
O2—C1—C2—N1	157.4 (4)	C12—C14—C15—C16	−0.9 (9)
O1—C1—C2—N1	−25.4 (6)	C13—N3—C16—C15	−0.7 (8)
C2—N1—C3—C4	77.1 (5)	Co1—N3—C16—C15	−178.7 (4)
Co1—N1—C3—C4	−38.8 (4)	C14—C15—C16—N3	0.5 (9)
Co1—O3—C4—O4	176.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2ⁱ	0.84 (5)	1.82 (4)	2.656 (5)	174 (6)
O1w—H12···O4ⁱⁱ	0.84 (6)	1.87 (4)	2.682 (5)	162 (6)
O2w—H21···O1ⁱ	0.84 (5)	1.98 (4)	2.815 (5)	174 (7)
O2w—H22···O4	0.84 (6)	2.05 (5)	2.871 (5)	165 (6)
N1—H1···O2ⁱⁱ	0.88	2.41	3.126 (6)	139

Symmetry codes: (i) x+1/2, −y+2, z−1/2; (ii) x−1/2, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₄H₅NO₄)(C₁₂H₈N₂)(H₂O)]·H₂O
M_r	406.26
Crystal system, space group	Monoclinic, Pn
Temperature (K)	100
a, b, c (Å)	6.7884 (3), 12.0903 (5), 10.4945 (4)
β (°)	108.357 (3)
V (Å³)	817.49 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.35 × 0.02 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.701, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	6417, 3639, 2997
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.126, 1.00
No. of reflections	3639
No. of parameters	248
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.49
Absolute structure	Flack (1983), 1746 Friedel pairs
Absolute structure parameter	0.38 (2)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2ⁱ	0.84 (5)	1.82 (4)	2.656 (5)	174 (6)
O1w—H12···O4ⁱⁱ	0.84 (6)	1.87 (4)	2.682 (5)	162 (6)
O2w—H21···O1ⁱ	0.84 (5)	1.98 (4)	2.815 (5)	174 (7)
O2w—H22···O4	0.84 (6)	2.05 (5)	2.871 (5)	165 (6)

Symmetry codes: (i) x+1/2, −y+2, z−1/2; (ii) x−1/2, −y+2, z−1/2.

Acknowledgements

We thank Universiti Tunku Abdul Rahman and the University of Malaya for supporting this study.

References

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