Benzene-1,3-diammonium bis­(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)cobaltate(II) penta­hydrate

Pasdar, H.; Sadat Kashani, S.; Ghiasi, R.; Aghabozorg, H.; Notash, B.

doi:10.1107/S1600536811009858

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m507-m508

doi:10.1107/S1600536811009858

Open

access

Benzene-1,3-diammonium bis(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)cobaltate(II) pentahydrate

Hoda Pasdar,^a ^* Saghi Sadat Kashani,^a Reza Ghiasi,^b Hossein Aghabozorg ^a and Behrouz Notash ^c

^aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^bDepartment of Chemistry, Basic Science Faculty, East Tehran Branch, Islamic Azad University, Qiam Dasht, Tehran, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: h_pasdar@iau-tnb.ac.ir

(Received 16 February 2011; accepted 16 March 2011; online 31 March 2011)

In the title compound, (C₆H₁₀N₂)[Co(C₇H₃NO₄)₂]·5H₂O, the Co^II ion is six-coordinated in an N₂O₄ environment by two pyridine-2,6-dicarboxylate (pydc) ligands, having a distorted octahedral geometry. The crystal packing is stabilized by intermolecular N—H⋯O, O—H⋯O and weak C—H⋯O hydrogen bonds. There are also π–π interactions between the pyridine rings of the pydc ligands and between the pydc ligands and the benzene-1,3-diammonium cations, with centroid–centroid distances of 3.4575 (15) and 3.7521 (15) Å.

Related literature

For general background to proton-transfer compounds, see: Aghabozorg et al. (2008 ). For related structures, see: Beatty et al. (2002 ); Dobrzycki & Woźniak (2008 ); Imaz et al. (2007 ); Pasdar et al. (2010 , 2011a ,b ).

Experimental

Crystal data

(C₆H₁₀N₂)[Co(C₇H₃NO₄)₂]·5H₂O
M_r = 589.38
Monoclinic, P 2₁ /n
a = 7.5236 (2) Å
b = 18.0200 (7) Å
c = 18.7122 (6) Å
β = 100.883 (2)°
V = 2491.29 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 298 K
0.50 × 0.15 × 0.10 mm

Data collection

Stoe IPDS-2 diffractometer
19874 measured reflections
6702 independent reflections
5366 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.113
S = 1.21
6702 reflections
407 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3ⁱ	0.93	2.57	3.311 (3)	136
C18—H18⋯O8ⁱⁱ	0.93	2.47	3.099 (3)	125
O9—H9A⋯O3	0.86 (4)	1.97 (4)	2.789 (3)	160 (3)
O9—H9B⋯O10	0.76 (3)	2.07 (3)	2.833 (4)	176 (4)
O10—H10A⋯O6ⁱ	0.81 (6)	2.10 (6)	2.913 (4)	173 (5)
O10—H10B⋯O11	0.80 (5)	1.97 (5)	2.764 (5)	170 (5)
O11—H11A⋯O8	0.97 (5)	1.84 (5)	2.746 (4)	153 (4)
O11—H11B⋯O13ⁱⁱⁱ	0.86 (5)	2.08 (5)	2.907 (4)	161 (5)
O12—H12A⋯O10	0.93 (7)	2.03 (7)	2.946 (5)	171 (5)
O12—H12B⋯O2^iv	0.73 (5)	2.09 (5)	2.786 (4)	161 (5)
O13—H13A⋯O12	0.86 (3)	1.95 (3)	2.805 (4)	176 (5)
O13—H13B⋯O5^v	0.78 (5)	2.13 (5)	2.873 (3)	161 (5)
N3—H3A⋯O4ⁱⁱⁱ	0.87 (4)	1.93 (4)	2.791 (3)	169 (3)
N3—H3B⋯O7	0.96 (4)	1.78 (4)	2.714 (3)	163 (3)
N3—H3C⋯O13ⁱⁱⁱ	0.98 (4)	2.04 (4)	2.890 (4)	144 (3)
N3—H3C⋯O9ⁱⁱⁱ	0.98 (4)	2.29 (4)	2.899 (3)	120 (3)
N4—H4A⋯O9	0.89 (4)	1.97 (4)	2.844 (3)	168 (4)
N4—H4B⋯O2^iv	0.90 (4)	1.87 (4)	2.752 (3)	166 (3)
N4—H4C⋯O6^v	0.88 (4)	2.00 (4)	2.873 (3)	175 (3)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009858/hy2407sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009858/hy2407Isup2.hkl

checkCIF report

Comment top

Our group used pyridine-2,6-dicarboxylic acid (pydcH₂) in several proton-transfer systems (Aghabozorg et al., 2008; Pasdar et al., 2010, 2011a,b). Benzene-1,3-diamine (bda) has ability to act as a proton acceptor in proton-transfer compounds. The formation of mono- (Beatty et al., 2002) and diprotonated benzene-1,3-diamine (Dobrzycki & Woźniak, 2008; Imaz et al., 2007) has been observed previously.

Herein, we report the synthesis and crystal structure of the title compound (Fig. 1). The Co^II ion in the complex anion is six-coordinated by two tridentate pydc ligands in a distorted octahedral geometry. We have recently reported the synthesis and crystal structure of a nickle(II) analogue, (bdaH₂)[Ni(pydc)₂].5H₂O (Pasdar et al., 2011b). The nickle(II) and cobalt(II) complexes are isostructural. Crystal packing of the title compound is stabilized by intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonds (Fig. 2, Table 1). There are also π–π interactions between the pyridine rings of the pydc ligands and between the pyridine ring of the pydc ligand and the benzene ring of the benzene-1,3-diammonium cation, with centroid–centroid distances of 3.4575 (15) and 3.7521 (15) Å.

Related literature top

For general background to proton-transfer compounds, see: Aghabozorg et al. (2008). For related structures, see: Beatty et al. (2002); Dobrzycki & Woźniak (2008); Imaz et al. (2007); Pasdar et al. (2010, 2011a,b).

Experimental top

A solution of pydcH₂ (162 mg, 0.9 mmol) in 17 ml water was added to a solution of bda (108 mg, 0.6 mmol) in 11 ml water with stirring for an hour, and then a solution of CoCl₂.6H₂O (118 mg, 0.6 mmol) in 5 ml water was added. The resulting solution was stirred for 2 h and dark pink crystals of the title compound suitable for X-ray analysis were obtained after one week (m.p. 260°C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing diagram of the title compound, viewed down the a axis. Intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonds are shown as blue dashed lines.
	Fig. 3. The packing diagram of the title compound, showing intermolecular π–π interactions (dashed lines) between the pyridine rings of the pydc ligands [centroid–centroid distance = 3.4575 (15) Å] and between the benzene rings of the (bdaH₂)²⁺ cations and the pyridine rings of the pydc ligands [centroid–centroid distance = 3.7521 (15) Å]. Water molecules have been omitted for clarity.

Benzene-1,3-diammonium bis(pyridine-2,6-dicarboxylato- κ³O²,N,O⁶)cobaltate(II) pentahydrate top

Crystal data top

(C₆H₁₀N₂)[Co(C₇H₃NO₄)₂]·5H₂O	F(000) = 1220
M_r = 589.38	D_x = 1.571 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6702 reflections
a = 7.5236 (2) Å	θ = 2.2–29.2°
b = 18.0200 (7) Å	µ = 0.76 mm⁻¹
c = 18.7122 (6) Å	T = 298 K
β = 100.883 (2)°	Needle, dark pink
V = 2491.29 (14) Å³	0.50 × 0.15 × 0.10 mm
Z = 4

Data collection top

Stoe IPDS-2 diffractometer	5366 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.064
Graphite monochromator	θ_max = 29.2°, θ_min = 2.2°
ω scans	h = −10→9
19874 measured reflections	k = −23→24
6702 independent reflections	l = −25→25

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ²(F_o²) + (0.031P)² + 1.7282P] where P = (F_o² + 2F_c²)/3
6702 reflections	(Δ/σ)_max = 0.007
407 parameters	Δρ_max = 0.34 e Å⁻³
2 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

(C₆H₁₀N₂)[Co(C₇H₃NO₄)₂]·5H₂O	V = 2491.29 (14) Å³
M_r = 589.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5236 (2) Å	µ = 0.76 mm⁻¹
b = 18.0200 (7) Å	T = 298 K
c = 18.7122 (6) Å	0.50 × 0.15 × 0.10 mm
β = 100.883 (2)°

Data collection top

Stoe IPDS-2 diffractometer	5366 reflections with I > 2σ(I)
19874 measured reflections	R_int = 0.064
6702 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	2 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	Δρ_max = 0.34 e Å⁻³
6702 reflections	Δρ_min = −0.32 e Å⁻³
407 parameters

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

	x	y	z	U_iso*/U_eq
Co1	0.64449 (5)	0.982592 (19)	0.312577 (16)	0.02479 (9)
O1	0.8779 (3)	1.03503 (13)	0.28454 (10)	0.0426 (5)
O2	1.0026 (3)	1.06589 (13)	0.19026 (12)	0.0481 (6)
O3	0.4033 (3)	0.91494 (11)	0.28828 (9)	0.0341 (4)
O4	0.2123 (3)	0.86302 (14)	0.19579 (11)	0.0471 (5)
O5	0.4980 (3)	1.08443 (11)	0.31941 (10)	0.0355 (4)
O6	0.4177 (3)	1.16437 (10)	0.39852 (11)	0.0348 (4)
O7	0.8000 (3)	0.88934 (11)	0.35988 (9)	0.0367 (4)
O8	0.9307 (3)	0.83948 (12)	0.46576 (11)	0.0448 (5)
O9	0.3372 (3)	0.77720 (13)	0.34605 (11)	0.0393 (5)
O10	0.5258 (5)	0.72787 (18)	0.48332 (16)	0.0614 (7)
O11	0.8434 (5)	0.69320 (18)	0.43693 (16)	0.0659 (7)
O12	0.3223 (4)	0.5943 (2)	0.42544 (17)	0.0670 (8)
O13	0.0351 (4)	0.65086 (15)	0.32207 (15)	0.0519 (6)
N1	0.6128 (3)	0.96490 (11)	0.20453 (10)	0.0251 (4)
N2	0.6870 (3)	1.00350 (10)	0.42057 (10)	0.0220 (4)
N3	0.9659 (3)	0.80230 (14)	0.27389 (12)	0.0292 (4)
N4	0.3688 (3)	0.68621 (13)	0.22490 (13)	0.0282 (4)
C1	0.7387 (4)	0.99011 (14)	0.16927 (13)	0.0288 (5)
C2	0.7267 (4)	0.97588 (17)	0.09568 (14)	0.0392 (6)
H2	0.8153	0.9927	0.0711	0.047*
C3	0.5791 (4)	0.93595 (17)	0.05974 (14)	0.0404 (7)
H3	0.5683	0.9257	0.0104	0.048*
C4	0.4476 (4)	0.91124 (16)	0.09695 (13)	0.0356 (6)
H4	0.3470	0.8851	0.0731	0.043*
C5	0.4702 (3)	0.92658 (14)	0.17044 (12)	0.0261 (5)
C6	0.8870 (4)	1.03362 (15)	0.21823 (14)	0.0327 (5)
C7	0.3483 (3)	0.89943 (14)	0.22113 (13)	0.0290 (5)
C8	0.6188 (3)	1.06555 (13)	0.44373 (12)	0.0242 (4)
C9	0.6530 (4)	1.08338 (15)	0.51711 (13)	0.0301 (5)
H9	0.6071	1.1268	0.5334	0.036*
C10	0.7571 (4)	1.03510 (15)	0.56585 (13)	0.0309 (5)
H10	0.7816	1.0462	0.6153	0.037*
C11	0.8246 (3)	0.97036 (14)	0.54083 (12)	0.0266 (5)
H11	0.8943	0.9375	0.5728	0.032*
C12	0.7848 (3)	0.95620 (13)	0.46633 (12)	0.0228 (4)
C13	0.5029 (3)	1.10953 (13)	0.38304 (13)	0.0261 (5)
C14	0.8452 (3)	0.88883 (14)	0.42920 (13)	0.0277 (5)
C15	0.8107 (3)	0.77539 (13)	0.22120 (12)	0.0242 (4)
C16	0.8140 (4)	0.77813 (15)	0.14768 (13)	0.0304 (5)
H16	0.9120	0.7987	0.1310	0.036*
C17	0.6676 (4)	0.74947 (17)	0.09941 (13)	0.0359 (6)
H17	0.6678	0.7504	0.0497	0.043*
C18	0.5211 (4)	0.71944 (15)	0.12409 (13)	0.0312 (5)
H18	0.4236	0.7002	0.0913	0.037*
C19	0.5212 (3)	0.71837 (13)	0.19752 (13)	0.0250 (5)
C20	0.6661 (3)	0.74587 (14)	0.24743 (12)	0.0266 (5)
H20	0.6659	0.7445	0.2971	0.032*
H3A	1.041 (5)	0.8267 (19)	0.2526 (18)	0.042 (9)*
H4A	0.342 (5)	0.714 (2)	0.261 (2)	0.057 (11)*
H9A	0.381 (5)	0.819 (2)	0.3366 (18)	0.043 (9)*
H10A	0.543 (7)	0.755 (3)	0.519 (3)	0.093 (18)*
H11A	0.903 (7)	0.741 (3)	0.439 (3)	0.087 (16)*
H12A	0.387 (9)	0.634 (4)	0.448 (3)	0.12 (2)*
H13A	0.125 (6)	0.633 (3)	0.352 (3)	0.11 (2)*
H3B	0.929 (5)	0.8373 (19)	0.3069 (18)	0.044 (9)*
H4B	0.403 (5)	0.642 (2)	0.2465 (19)	0.052 (10)*
H9B	0.385 (5)	0.763 (2)	0.3831 (17)	0.055 (12)*
H10B	0.624 (7)	0.719 (3)	0.475 (2)	0.068 (15)*
H11B	0.886 (7)	0.671 (3)	0.403 (3)	0.081 (15)*
H12B	0.380 (7)	0.580 (3)	0.401 (3)	0.074 (16)*
H13B	0.033 (7)	0.624 (3)	0.289 (3)	0.089 (17)*
H3C	1.035 (5)	0.762 (2)	0.301 (2)	0.057 (11)*
H4C	0.277 (5)	0.6805 (19)	0.1891 (19)	0.045 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02959 (17)	0.02648 (16)	0.01790 (13)	−0.00151 (14)	0.00348 (11)	−0.00162 (12)
O1	0.0403 (11)	0.0565 (14)	0.0311 (9)	−0.0213 (10)	0.0069 (8)	−0.0076 (9)
O2	0.0504 (13)	0.0507 (13)	0.0487 (12)	−0.0263 (11)	0.0232 (10)	−0.0087 (10)
O3	0.0383 (10)	0.0402 (10)	0.0258 (8)	−0.0118 (8)	0.0109 (7)	−0.0033 (7)
O4	0.0383 (11)	0.0640 (15)	0.0388 (10)	−0.0237 (10)	0.0065 (9)	−0.0065 (10)
O5	0.0451 (11)	0.0319 (10)	0.0269 (8)	0.0085 (8)	0.0001 (8)	0.0007 (7)
O6	0.0304 (10)	0.0303 (10)	0.0425 (10)	0.0070 (8)	0.0039 (8)	−0.0020 (8)
O7	0.0486 (12)	0.0358 (10)	0.0244 (8)	0.0155 (9)	0.0036 (8)	−0.0048 (7)
O8	0.0575 (14)	0.0389 (11)	0.0366 (10)	0.0198 (10)	0.0052 (9)	0.0045 (9)
O9	0.0457 (12)	0.0370 (12)	0.0338 (10)	−0.0053 (9)	0.0035 (9)	−0.0008 (9)
O10	0.0624 (19)	0.0697 (19)	0.0494 (14)	0.0069 (15)	0.0035 (13)	−0.0104 (13)
O11	0.082 (2)	0.0566 (17)	0.0617 (17)	0.0052 (15)	0.0205 (15)	−0.0063 (14)
O12	0.0659 (19)	0.084 (2)	0.0579 (16)	0.0049 (17)	0.0296 (15)	−0.0025 (15)
O13	0.0587 (16)	0.0464 (14)	0.0483 (13)	0.0015 (11)	0.0047 (12)	−0.0124 (11)
N1	0.0312 (11)	0.0235 (10)	0.0206 (8)	−0.0037 (8)	0.0054 (7)	−0.0010 (7)
N2	0.0222 (9)	0.0237 (10)	0.0203 (8)	−0.0007 (7)	0.0045 (7)	−0.0012 (7)
N3	0.0210 (10)	0.0362 (12)	0.0301 (10)	−0.0029 (9)	0.0036 (8)	−0.0084 (9)
N4	0.0239 (10)	0.0273 (11)	0.0331 (11)	−0.0015 (8)	0.0048 (9)	−0.0008 (9)
C1	0.0346 (13)	0.0261 (12)	0.0271 (11)	−0.0048 (10)	0.0093 (9)	0.0001 (9)
C2	0.0521 (17)	0.0404 (15)	0.0294 (12)	−0.0096 (13)	0.0184 (11)	−0.0011 (11)
C3	0.0572 (19)	0.0425 (16)	0.0224 (11)	−0.0083 (13)	0.0099 (11)	−0.0042 (11)
C4	0.0434 (15)	0.0367 (14)	0.0247 (11)	−0.0083 (12)	0.0009 (10)	−0.0068 (10)
C5	0.0276 (12)	0.0261 (12)	0.0242 (10)	−0.0022 (9)	0.0036 (9)	0.0001 (9)
C6	0.0352 (13)	0.0302 (13)	0.0346 (12)	−0.0081 (10)	0.0118 (10)	−0.0034 (10)
C7	0.0279 (12)	0.0311 (13)	0.0282 (11)	−0.0048 (10)	0.0058 (9)	−0.0014 (10)
C8	0.0227 (11)	0.0241 (11)	0.0263 (10)	−0.0014 (8)	0.0056 (8)	−0.0023 (9)
C9	0.0322 (13)	0.0304 (12)	0.0285 (11)	−0.0010 (10)	0.0077 (10)	−0.0102 (10)
C10	0.0337 (13)	0.0384 (14)	0.0204 (10)	−0.0044 (10)	0.0044 (9)	−0.0079 (9)
C11	0.0249 (11)	0.0335 (13)	0.0212 (10)	−0.0012 (9)	0.0036 (8)	0.0022 (9)
C12	0.0205 (10)	0.0271 (11)	0.0213 (10)	0.0000 (8)	0.0053 (8)	0.0002 (8)
C13	0.0223 (11)	0.0249 (11)	0.0307 (11)	−0.0024 (9)	0.0036 (9)	−0.0003 (9)
C14	0.0277 (12)	0.0284 (12)	0.0266 (11)	0.0023 (9)	0.0043 (9)	0.0008 (9)
C15	0.0194 (10)	0.0261 (11)	0.0263 (10)	0.0018 (9)	0.0022 (8)	−0.0058 (9)
C16	0.0287 (12)	0.0345 (13)	0.0295 (12)	−0.0015 (10)	0.0094 (10)	−0.0021 (10)
C17	0.0377 (15)	0.0482 (16)	0.0219 (11)	−0.0040 (12)	0.0060 (10)	−0.0036 (11)
C18	0.0298 (13)	0.0331 (13)	0.0284 (11)	−0.0040 (10)	−0.0004 (9)	−0.0074 (10)
C19	0.0200 (11)	0.0238 (11)	0.0312 (11)	0.0007 (9)	0.0044 (9)	−0.0027 (9)
C20	0.0252 (12)	0.0310 (12)	0.0235 (10)	−0.0004 (9)	0.0042 (9)	−0.0035 (9)

Geometric parameters (Å, º) top

Co1—N1	2.0160 (19)	N4—C19	1.461 (3)
Co1—N2	2.0209 (18)	N4—H4A	0.89 (4)
Co1—O7	2.1414 (19)	N4—H4B	0.90 (4)
Co1—O1	2.145 (2)	N4—H4C	0.88 (4)
Co1—O5	2.1570 (19)	C1—C2	1.387 (3)
Co1—O3	2.1621 (19)	C1—C6	1.521 (4)
O1—C6	1.256 (3)	C2—C3	1.386 (4)
O2—C6	1.241 (3)	C2—H2	0.9300
O3—C7	1.277 (3)	C3—C4	1.387 (4)
O4—C7	1.233 (3)	C3—H3	0.9300
O5—C13	1.268 (3)	C4—C5	1.381 (3)
O6—C13	1.242 (3)	C4—H4	0.9300
O7—C14	1.277 (3)	C5—C7	1.519 (3)
O8—C14	1.228 (3)	C8—C9	1.386 (3)
O9—H9A	0.86 (4)	C8—C13	1.518 (3)
O9—H9B	0.76 (3)	C9—C10	1.390 (4)
O10—H10A	0.81 (6)	C9—H9	0.9300
O10—H10B	0.80 (5)	C10—C11	1.389 (4)
O11—H11A	0.97 (5)	C10—H10	0.9300
O11—H11B	0.86 (5)	C11—C12	1.393 (3)
O12—H12A	0.93 (7)	C11—H11	0.9300
O12—H12B	0.73 (5)	C12—C14	1.511 (3)
O13—H13A	0.86 (3)	C15—C16	1.381 (3)
O13—H13B	0.78 (5)	C15—C20	1.382 (3)
N1—C5	1.332 (3)	C16—C17	1.386 (4)
N1—C1	1.333 (3)	C16—H16	0.9300
N2—C12	1.328 (3)	C17—C18	1.383 (4)
N2—C8	1.336 (3)	C17—H17	0.9300
N3—C15	1.462 (3)	C18—C19	1.374 (3)
N3—H3A	0.87 (4)	C18—H18	0.9300
N3—H3B	0.96 (4)	C19—C20	1.386 (3)
N3—H3C	0.98 (4)	C20—H20	0.9300

N1—Co1—N2	177.16 (8)	C5—C4—C3	118.0 (2)
N1—Co1—O7	104.03 (7)	C5—C4—H4	121.0
N2—Co1—O7	76.23 (7)	C3—C4—H4	121.0
N1—Co1—O1	76.81 (8)	N1—C5—C4	121.1 (2)
N2—Co1—O1	100.37 (7)	N1—C5—C7	113.2 (2)
O7—Co1—O1	92.18 (9)	C4—C5—C7	125.6 (2)
N1—Co1—O5	103.23 (8)	O2—C6—O1	125.5 (3)
N2—Co1—O5	76.60 (7)	O2—C6—C1	118.7 (2)
O7—Co1—O5	152.70 (7)	O1—C6—C1	115.8 (2)
O1—Co1—O5	95.22 (9)	O4—C7—O3	125.9 (2)
N1—Co1—O3	76.36 (7)	O4—C7—C5	119.1 (2)
N2—Co1—O3	106.48 (7)	O3—C7—C5	115.0 (2)
O7—Co1—O3	90.92 (8)	N2—C8—C9	120.3 (2)
O1—Co1—O3	152.93 (7)	N2—C8—C13	113.31 (19)
O5—Co1—O3	94.25 (8)	C9—C8—C13	126.4 (2)
C6—O1—Co1	115.64 (17)	C8—C9—C10	118.7 (2)
C7—O3—Co1	115.67 (16)	C8—C9—H9	120.6
C13—O5—Co1	115.76 (16)	C10—C9—H9	120.6
C14—O7—Co1	116.43 (16)	C11—C10—C9	120.1 (2)
H9A—O9—H9B	111 (4)	C11—C10—H10	120.0
H10A—O10—H10B	106 (5)	C9—C10—H10	120.0
H11A—O11—H11B	102 (4)	C10—C11—C12	117.9 (2)
H12A—O12—H12B	104 (5)	C10—C11—H11	121.0
H13A—O13—H13B	100 (5)	C12—C11—H11	121.0
C5—N1—C1	121.5 (2)	N2—C12—C11	121.1 (2)
C5—N1—Co1	119.62 (16)	N2—C12—C14	113.42 (19)
C1—N1—Co1	118.82 (16)	C11—C12—C14	125.5 (2)
C12—N2—C8	121.87 (19)	O6—C13—O5	125.3 (2)
C12—N2—Co1	119.28 (15)	O6—C13—C8	119.3 (2)
C8—N2—Co1	118.84 (15)	O5—C13—C8	115.3 (2)
C15—N3—H3A	111 (2)	O8—C14—O7	125.6 (2)
C15—N3—H3B	111 (2)	O8—C14—C12	119.8 (2)
H3A—N3—H3B	105 (3)	O7—C14—C12	114.6 (2)
C15—N3—H3C	112 (2)	C16—C15—C20	122.1 (2)
H3A—N3—H3C	107 (3)	C16—C15—N3	119.8 (2)
H3B—N3—H3C	110 (3)	C20—C15—N3	118.1 (2)
C19—N4—H4A	110 (3)	C15—C16—C17	118.3 (2)
C19—N4—H4B	109 (2)	C15—C16—H16	120.8
H4A—N4—H4B	104 (3)	C17—C16—H16	120.8
C19—N4—H4C	110 (2)	C18—C17—C16	120.9 (2)
H4A—N4—H4C	112 (3)	C18—C17—H17	119.5
H4B—N4—H4C	111 (3)	C16—C17—H17	119.5
N1—C1—C2	120.6 (2)	C19—C18—C17	119.3 (2)
N1—C1—C6	112.8 (2)	C19—C18—H18	120.4
C2—C1—C6	126.6 (2)	C17—C18—H18	120.4
C3—C2—C1	118.3 (2)	C18—C19—C20	121.4 (2)
C3—C2—H2	120.9	C18—C19—N4	120.3 (2)
C1—C2—H2	120.9	C20—C19—N4	118.3 (2)
C2—C3—C4	120.4 (2)	C15—C20—C19	118.0 (2)
C2—C3—H3	119.8	C15—C20—H20	121.0
C4—C3—H3	119.8	C19—C20—H20	121.0

N1—Co1—O1—C6	2.1 (2)	C3—C4—C5—C7	−175.3 (3)
N2—Co1—O1—C6	−177.6 (2)	Co1—O1—C6—O2	173.7 (2)
O7—Co1—O1—C6	106.0 (2)	Co1—O1—C6—C1	−4.3 (3)
O5—Co1—O1—C6	−100.3 (2)	N1—C1—C6—O2	−173.2 (3)
O3—Co1—O1—C6	9.7 (3)	C2—C1—C6—O2	6.8 (4)
N1—Co1—O3—C7	−3.76 (19)	N1—C1—C6—O1	5.0 (4)
N2—Co1—O3—C7	176.12 (18)	C2—C1—C6—O1	−174.9 (3)
O7—Co1—O3—C7	−107.98 (19)	Co1—O3—C7—O4	−178.5 (2)
O1—Co1—O3—C7	−11.4 (3)	Co1—O3—C7—C5	4.3 (3)
O5—Co1—O3—C7	98.85 (19)	N1—C5—C7—O4	−179.7 (3)
N1—Co1—O5—C13	−177.44 (18)	C4—C5—C7—O4	−3.2 (4)
N2—Co1—O5—C13	−0.35 (18)	N1—C5—C7—O3	−2.3 (3)
O7—Co1—O5—C13	5.3 (3)	C4—C5—C7—O3	174.2 (3)
O1—Co1—O5—C13	−99.79 (19)	C12—N2—C8—C9	1.8 (3)
O3—Co1—O5—C13	105.59 (19)	Co1—N2—C8—C9	−176.81 (18)
N1—Co1—O7—C14	177.36 (19)	C12—N2—C8—C13	−176.8 (2)
N2—Co1—O7—C14	0.26 (19)	Co1—N2—C8—C13	4.6 (3)
O1—Co1—O7—C14	100.4 (2)	N2—C8—C9—C10	−0.9 (4)
O5—Co1—O7—C14	−5.4 (3)	C13—C8—C9—C10	177.6 (2)
O3—Co1—O7—C14	−106.5 (2)	C8—C9—C10—C11	−0.1 (4)
O7—Co1—N1—C5	89.93 (19)	C9—C10—C11—C12	0.1 (4)
O1—Co1—N1—C5	178.9 (2)	C8—N2—C12—C11	−1.7 (3)
O5—Co1—N1—C5	−88.78 (19)	Co1—N2—C12—C11	176.86 (17)
O3—Co1—N1—C5	2.43 (18)	C8—N2—C12—C14	178.6 (2)
O7—Co1—N1—C1	−88.0 (2)	Co1—N2—C12—C14	−2.8 (3)
O1—Co1—N1—C1	0.90 (19)	C10—C11—C12—N2	0.7 (4)
O5—Co1—N1—C1	93.24 (19)	C10—C11—C12—C14	−179.7 (2)
O3—Co1—N1—C1	−175.5 (2)	Co1—O5—C13—O6	−174.9 (2)
O7—Co1—N2—C12	1.51 (17)	Co1—O5—C13—C8	2.7 (3)
O1—Co1—N2—C12	−88.20 (18)	N2—C8—C13—O6	173.0 (2)
O5—Co1—N2—C12	178.85 (19)	C9—C8—C13—O6	−5.5 (4)
O3—Co1—N2—C12	88.34 (18)	N2—C8—C13—O5	−4.8 (3)
O7—Co1—N2—C8	−179.87 (19)	C9—C8—C13—O5	176.7 (2)
O1—Co1—N2—C8	90.42 (18)	Co1—O7—C14—O8	178.4 (2)
O5—Co1—N2—C8	−2.53 (17)	Co1—O7—C14—C12	−1.7 (3)
O3—Co1—N2—C8	−93.04 (18)	N2—C12—C14—O8	−177.2 (2)
C5—N1—C1—C2	−1.2 (4)	C11—C12—C14—O8	3.1 (4)
Co1—N1—C1—C2	176.7 (2)	N2—C12—C14—O7	2.9 (3)
C5—N1—C1—C6	178.8 (2)	C11—C12—C14—O7	−176.7 (2)
Co1—N1—C1—C6	−3.2 (3)	C20—C15—C16—C17	−0.7 (4)
N1—C1—C2—C3	1.0 (4)	N3—C15—C16—C17	177.5 (2)
C6—C1—C2—C3	−179.0 (3)	C15—C16—C17—C18	0.5 (4)
C1—C2—C3—C4	0.1 (5)	C16—C17—C18—C19	0.2 (4)
C2—C3—C4—C5	−1.1 (5)	C17—C18—C19—C20	−0.9 (4)
C1—N1—C5—C4	0.2 (4)	C17—C18—C19—N4	−179.3 (2)
Co1—N1—C5—C4	−177.8 (2)	C16—C15—C20—C19	0.1 (4)
C1—N1—C5—C7	176.9 (2)	N3—C15—C20—C19	−178.1 (2)
Co1—N1—C5—C7	−1.0 (3)	C18—C19—C20—C15	0.7 (4)
C3—C4—C5—N1	1.0 (4)	N4—C19—C20—C15	179.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3ⁱ	0.93	2.57	3.311 (3)	136
C18—H18···O8ⁱⁱ	0.93	2.47	3.099 (3)	125
O9—H9A···O3	0.86 (4)	1.97 (4)	2.789 (3)	160 (3)
O9—H9B···O10	0.76 (3)	2.07 (3)	2.833 (4)	176 (4)
O10—H10A···O6ⁱ	0.81 (6)	2.10 (6)	2.913 (4)	173 (5)
O10—H10B···O11	0.80 (5)	1.97 (5)	2.764 (5)	170 (5)
O11—H11A···O8	0.97 (5)	1.84 (5)	2.746 (4)	153 (4)
O11—H11B···O13ⁱⁱⁱ	0.86 (5)	2.08 (5)	2.907 (4)	161 (5)
O12—H12A···O10	0.93 (7)	2.03 (7)	2.946 (5)	171 (5)
O12—H12B···O2^iv	0.73 (5)	2.09 (5)	2.786 (4)	161 (5)
O13—H13A···O12	0.86 (3)	1.95 (3)	2.805 (4)	176 (5)
O13—H13B···O5^v	0.78 (5)	2.13 (5)	2.873 (3)	161 (5)
N3—H3A···O4ⁱⁱⁱ	0.87 (4)	1.93 (4)	2.791 (3)	169 (3)
N3—H3B···O7	0.96 (4)	1.78 (4)	2.714 (3)	163 (3)
N3—H3C···O13ⁱⁱⁱ	0.98 (4)	2.04 (4)	2.890 (4)	144 (3)
N3—H3C···O9ⁱⁱⁱ	0.98 (4)	2.29 (4)	2.899 (3)	120 (3)
N4—H4A···O9	0.89 (4)	1.97 (4)	2.844 (3)	168 (4)
N4—H4B···O2^iv	0.90 (4)	1.87 (4)	2.752 (3)	166 (3)
N4—H4C···O6^v	0.88 (4)	2.00 (4)	2.873 (3)	175 (3)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1, y, z; (iv) −x+3/2, y−1/2, −z+1/2; (v) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	(C₆H₁₀N₂)[Co(C₇H₃NO₄)₂]·5H₂O
M_r	589.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.5236 (2), 18.0200 (7), 18.7122 (6)
β (°)	100.883 (2)
V (Å³)	2491.29 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.50 × 0.15 × 0.10

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19874, 6702, 5366
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.113, 1.21
No. of reflections	6702
No. of parameters	407
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.32

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3ⁱ	0.93	2.57	3.311 (3)	136
C18—H18···O8ⁱⁱ	0.93	2.47	3.099 (3)	125
O9—H9A···O3	0.86 (4)	1.97 (4)	2.789 (3)	160 (3)
O9—H9B···O10	0.76 (3)	2.07 (3)	2.833 (4)	176 (4)
O10—H10A···O6ⁱ	0.81 (6)	2.10 (6)	2.913 (4)	173 (5)
O10—H10B···O11	0.80 (5)	1.97 (5)	2.764 (5)	170 (5)
O11—H11A···O8	0.97 (5)	1.84 (5)	2.746 (4)	153 (4)
O11—H11B···O13ⁱⁱⁱ	0.86 (5)	2.08 (5)	2.907 (4)	161 (5)
O12—H12A···O10	0.93 (7)	2.03 (7)	2.946 (5)	171 (5)
O12—H12B···O2^iv	0.73 (5)	2.09 (5)	2.786 (4)	161 (5)
O13—H13A···O12	0.86 (3)	1.95 (3)	2.805 (4)	176 (5)
O13—H13B···O5^v	0.78 (5)	2.13 (5)	2.873 (3)	161 (5)
N3—H3A···O4ⁱⁱⁱ	0.87 (4)	1.93 (4)	2.791 (3)	169 (3)
N3—H3B···O7	0.96 (4)	1.78 (4)	2.714 (3)	163 (3)
N3—H3C···O13ⁱⁱⁱ	0.98 (4)	2.04 (4)	2.890 (4)	144 (3)
N3—H3C···O9ⁱⁱⁱ	0.98 (4)	2.29 (4)	2.899 (3)	120 (3)
N4—H4A···O9	0.89 (4)	1.97 (4)	2.844 (3)	168 (4)
N4—H4B···O2^iv	0.90 (4)	1.87 (4)	2.752 (3)	166 (3)
N4—H4C···O6^v	0.88 (4)	2.00 (4)	2.873 (3)	175 (3)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1, y, z; (iv) −x+3/2, y−1/2, −z+1/2; (v) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

The authors are grateful to Islamic Azad University, North Branch, for financial support of this work.

References

Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
Beatty, A. M., Granger, K. E. & Simpson, A. E. (2002). Chem. Eur. J. 8, 3254–3259. CrossRef PubMed CAS Google Scholar
Dobrzycki, L. & Woźniak, K. (2008). CrystEngComm, 10, 577–589. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Imaz, I., Thillet, A. & Sutter, J. P. (2007). Cryst. Growth Des. 7, 1753–1761. Web of Science CSD CrossRef CAS Google Scholar
Pasdar, H., Ebdam, A., Aghabozorg, H. & Notash, B. (2011a). Acta Cryst. E67, m294. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pasdar, H., Heidari, S., Aghabozorg, H. & Notash, B. (2010). Acta Cryst. E66, m1581. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pasdar, H., Sadat Kashani, S., Aghabozorg, H. & Notash, B. (2011b). Acta Cryst. E67, m193–m194. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.