1H-Benzotriazol-3-ium (1H-benzo­triazole-κN3)trichloridocobaltate(II) monohydrate: a reformulation

Sieroń, L.

doi:10.1107/S1600536807063131

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m58

https://doi.org/10.1107/S1600536807063131

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1H-Benzotriazol-3-ium (1H-benzotriazole-κN³)trichloridocobaltate(II) monohydrate: a reformulation

Lesław Sieroń ^a ^*

^aInstitute of General & Ecological Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland
^*Correspondence e-mail: lsieron@p.lodz.pl

(Received 14 November 2007; accepted 25 November 2007; online 6 December 2007)

The asymmetric unit of the title compound, (C₆H₆N₃)[CoCl₃(C₆H₅N₃)]·H₂O, contains two crystallographically independent cations, two anions and two water molecules. The structure has been reported previously [Zhang, Li, Wang, Xie, Wang & Shen (2004 ). Acta Cryst E60, m498–m500] as a neutral cobalt(III) complex accompanied by unprotonated benzotriazole molecules and here has been redetermined as an anionic cobalt(II) complex accompanied by protonated benzotriazole cations. For both complex anions, a tetrahedral CoNCl₃ geometry arises. A network of N—H⋯O, N—H⋯Cl, O—H⋯O and O—H⋯Cl hydrogen bonds helps to establish the packing.

Related literature

For the previous stucture, see: Zhang et al. (2004). For related Co(II)-containing structures, see: Hahn et al. (1997 ); Krawczyk & Gdaniec (2005 ); Pan & Xu (2004 ); Zhang et al. (2006 );

Experimental

Crystal data

(C₆H₆N₃)[CoCl₃(C₆H₅N₃)]·H₂O
M_r = 422.56
Triclinic, P 1
a = 6.8760 (8) Å
b = 7.8033 (12) Å
c = 16.657 (3) Å
α = 95.450 (13)°
β = 95.962 (8)°
γ = 103.989 (9)°
V = 855.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.48 mm⁻¹
T = 293 (2) K
0.40 × 0.40 × 0.20 mm

Data collection

Bruker P4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.611, T_max = 0.744
4906 measured reflections
4846 independent reflections
4526 reflections with I > 2σ(I)
R_int = 0.078
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.078
S = 1.08
4846 reflections
417 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 920 Friedel pairs
Flack parameter: −0.008 (13)

Table 1
Selected bond lengths (Å)

Co1—Cl1	2.2649 (13)
Co1—Cl2	2.2616 (13)
Co1—Cl3	2.2195 (16)
Co1—N1	2.027 (3)
Co2—Cl4	2.2441 (13)
Co2—Cl5	2.2450 (15)
Co2—Cl6	2.2584 (16)
Co2—N11	2.022 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯Cl6	0.82	2.79	3.279 (5)	120
O2—H2A⋯O1ⁱ	0.82	2.41	3.142 (7)	148
O2—H2B⋯Cl6	0.82	2.52	3.295 (5)	159
N3—H3⋯O2ⁱⁱ	0.86	1.87	2.721 (4)	173
N13—H13⋯Cl2ⁱⁱⁱ	0.86	2.28	3.127 (3)	169
N21—H21⋯Cl4	0.86	2.80	3.458 (4)	134
N21—H21⋯Cl6^iv	0.86	2.75	3.316 (4)	125
N23—H23⋯Cl1^v	0.86	2.30	3.123 (3)	160
N31—H31⋯Cl3^vi	0.86	2.61	3.214 (4)	128
N33—H33⋯O1ⁱ	0.86	1.79	2.646 (5)	170
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) x, y, z-1; (iv) x+1, y, z; (v) x+1, y+1, z; (vi) x-1, y+1, z-1.

Data collection: XSCANS (Bruker, 1997 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 2003 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063131/hb2664sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063131/hb2664Isup2.hkl

checkCIF report

Comment top

The crystal structure of the salt-like title compound, (I), C₆H₆N₃⁺.[CoCl₃(C₆H₅N₃)]^-.H₂O, was originally modelled as a [CoCl₃(C₆H₅N₃)].C₆H₅N₃.H₂O complex (Zhang et al., 2004). A few facts point that the structure was incorrectly described as Co^III instead of Co^II complex. The blue colour of the crystal and a tetrahedral coordination geometry around the central metal atom is typical for the Co^IICl₃N chromophore, e.g. in pyridinium trichloro-pyridine-cobalt(II) (Hahn et al., 1997), quinolinium trichloro-quinoline-cobalt(II) (Pan & Xu, 2004) and 2-aminopyridinium (2-aminopyridine)-trichloro-cobalt(II) (Zhang et al., 2006).

A decrease of the metal oxidation number in (I) from III to II requires the presence of an additional proton for charge balance. In fact, an analysis of difference Fourier maps has shown two peaks in the positions expected for missing benzotriazole H atoms (N–Q = 0.85 and 0.89 Å). Both of these are involved in short, strong N–H···O_water hydrogen bonds which confirms the supposition (Fig. 1). The N–N bond lengths in the benzimidazolium cations are practically equalized and range from 1.309 (4) to 1.316 (5) Å, indicating full delocalization of their π electrons, which is not observed in neutral benzotriazole molecules (Krawczyk & Gdaniec, 2005). The metal bond distances and hydrogen bonds are listed in Tables 1 and 2, respectively.

Related literature top

For the previous stucture, see: Zhang et al. (2006). For related Co(II)-containing structures, see: Hahn et al. (1997); Krawczyk & Gdaniec (2005); Pan & Xu (2004); Zhang et al. (2004)

Experimental top

Due to the unsuccesful attempts at the synthesis of (I), the deposited structure factors and other data have been taken from the original paper of Zhang et al. (2004).

Structure description top

For the previous stucture, see: Zhang et al. (2006). For related Co(II)-containing structures, see: Hahn et al. (1997); Krawczyk & Gdaniec (2005); Pan & Xu (2004); Zhang et al. (2004)

Computing details top

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS (Bruker, 1997); data reduction: XSCANS (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL (Bruker, 2003); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. A view of (I), showing displacement ellipsoids for the non-H atoms drawn at the 30% probability level.

1H-Benzotriazol-3-ium (1H-benzotriazole-κN³)trichloridocobalt(II) monohydrate top

Crystal data top

(C₆H₆N₃)[CoCl₃(C₆H₅N₃)]·H₂O	Z = 2
M_r = 422.56	F(000) = 426
Triclinic, P1	D_x = 1.640 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8760 (8) Å	Cell parameters from 28 reflections
b = 7.8033 (12) Å	θ = 5.3–12.6°
c = 16.657 (3) Å	µ = 1.48 mm⁻¹
α = 95.450 (13)°	T = 293 K
β = 95.962 (8)°	Prism, blue
γ = 103.989 (9)°	0.40 × 0.40 × 0.20 mm
V = 855.8 (2) Å³

Data collection top

Bruker P4 diffractometer	4526 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.078
Graphite monochromator	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −8→1
Absorption correction: ψ scan (North et al., 1968)	k = −9→10
T_min = 0.611, T_max = 0.744	l = −21→21
4906 measured reflections	3 standard reflections every 100 reflections
4846 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0331P)² + 0.2297P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
4846 reflections	Δρ_max = 0.34 e Å⁻³
417 parameters	Δρ_min = −0.26 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 920 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.008 (13)

Crystal data top

(C₆H₆N₃)[CoCl₃(C₆H₅N₃)]·H₂O	γ = 103.989 (9)°
M_r = 422.56	V = 855.8 (2) Å³
Triclinic, P1	Z = 2
a = 6.8760 (8) Å	Mo Kα radiation
b = 7.8033 (12) Å	µ = 1.48 mm⁻¹
c = 16.657 (3) Å	T = 293 K
α = 95.450 (13)°	0.40 × 0.40 × 0.20 mm
β = 95.962 (8)°

Data collection top

Bruker P4 diffractometer	4526 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.078
T_min = 0.611, T_max = 0.744	3 standard reflections every 100 reflections
4906 measured reflections	intensity decay: none
4846 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.34 e Å⁻³
S = 1.08	Δρ_min = −0.26 e Å⁻³
4846 reflections	Absolute structure: Flack (1983), 920 Friedel pairs
417 parameters	Absolute structure parameter: −0.008 (13)
3 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

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

	x	y	z	U_iso*/U_eq
Co1	0.44420 (6)	0.01369 (5)	0.90042 (3)	0.0462 (1)
Cl1	0.1994 (2)	−0.24333 (13)	0.89041 (6)	0.0706 (3)
Cl2	0.3415 (2)	0.22168 (14)	0.97717 (6)	0.0707 (4)
Cl3	0.7529 (2)	−0.0156 (3)	0.93735 (8)	0.0969 (6)
N1	0.4450 (5)	0.0908 (4)	0.78758 (16)	0.0436 (8)
N2	0.3859 (5)	−0.0327 (4)	0.72406 (17)	0.0491 (9)
N3	0.3929 (5)	0.0501 (4)	0.65771 (17)	0.0487 (9)
C4	0.4831 (7)	0.3714 (6)	0.6303 (3)	0.0585 (12)
C5	0.5466 (8)	0.5379 (6)	0.6726 (3)	0.0669 (16)
C6	0.5824 (8)	0.5658 (5)	0.7580 (3)	0.0674 (15)
C7	0.5560 (6)	0.4277 (5)	0.8042 (2)	0.0560 (11)
C8	0.4911 (5)	0.2557 (4)	0.7616 (2)	0.0441 (9)
C9	0.4567 (5)	0.2298 (5)	0.6770 (2)	0.0446 (9)
Co2	0.55479 (7)	0.48473 (5)	0.39999 (3)	0.0484 (1)
Cl4	0.6620 (2)	0.24123 (14)	0.42163 (7)	0.0745 (4)
Cl5	0.7823 (3)	0.72314 (15)	0.46890 (8)	0.0979 (6)
Cl6	0.2402 (2)	0.4745 (2)	0.43067 (8)	0.0891 (5)
N11	0.5282 (5)	0.5107 (4)	0.27999 (16)	0.0445 (8)
N12	0.4780 (6)	0.3689 (4)	0.22487 (17)	0.0514 (9)
N13	0.4662 (6)	0.4279 (4)	0.15251 (17)	0.0542 (9)
C14	0.5165 (7)	0.7309 (6)	0.1018 (2)	0.0570 (11)
C15	0.5618 (8)	0.9044 (6)	0.1336 (3)	0.0630 (16)
C16	0.5992 (7)	0.9600 (5)	0.2186 (3)	0.0606 (13)
C17	0.5933 (6)	0.8414 (5)	0.2737 (2)	0.0512 (10)
C18	0.5479 (5)	0.6616 (4)	0.24206 (18)	0.0409 (9)
C19	0.5082 (6)	0.6077 (5)	0.1583 (2)	0.0453 (10)
N21	0.9897 (6)	0.4698 (4)	0.59051 (19)	0.0554 (10)
N22	1.0593 (6)	0.6201 (4)	0.6387 (2)	0.0608 (11)
N23	1.0793 (5)	0.5710 (4)	0.71148 (18)	0.0531 (9)
C24	1.0184 (7)	0.2821 (6)	0.7735 (2)	0.0581 (11)
C25	0.9546 (7)	0.1017 (6)	0.7485 (3)	0.0670 (16)
C26	0.8995 (7)	0.0348 (6)	0.6655 (3)	0.0695 (16)
C27	0.9026 (7)	0.1394 (5)	0.6052 (3)	0.0605 (14)
C28	0.9658 (6)	0.3237 (5)	0.6305 (2)	0.0462 (10)
C29	1.0242 (5)	0.3911 (5)	0.7118 (2)	0.0439 (10)
N31	0.0523 (6)	0.8803 (5)	0.0749 (2)	0.0609 (13)
N32	0.0951 (7)	1.0044 (5)	0.1374 (2)	0.0673 (14)
N33	0.0884 (6)	0.9186 (5)	0.2018 (2)	0.0581 (11)
C34	0.0247 (7)	0.5974 (7)	0.2283 (3)	0.0671 (16)
C35	−0.0210 (9)	0.4337 (7)	0.1856 (4)	0.0788 (19)
C36	−0.0493 (8)	0.4068 (6)	0.1003 (4)	0.0805 (18)
C37	−0.0293 (8)	0.5435 (6)	0.0545 (3)	0.0688 (14)
C38	0.0182 (7)	0.7128 (5)	0.0974 (2)	0.0531 (11)
C39	0.0438 (6)	0.7406 (5)	0.1818 (2)	0.0514 (11)
O1	0.1150 (10)	0.0529 (7)	0.3557 (2)	0.127 (2)
O2	0.3201 (10)	0.8988 (6)	0.4999 (2)	0.124 (2)
H3	0.36100	−0.00330	0.60880	0.0580*
H4	0.45880	0.35330	0.57380	0.0710*
H5	0.56690	0.63600	0.64400	0.0810*
H6	0.62540	0.68190	0.78410	0.0810*
H7	0.57990	0.44690	0.86070	0.0670*
H13	0.43520	0.35920	0.10710	0.0650*
H14	0.49230	0.69560	0.04600	0.0680*
H15	0.56870	0.99050	0.09830	0.0760*
H16	0.62860	1.08080	0.23720	0.0730*
H17	0.61810	0.87790	0.32940	0.0620*
H21	0.96190	0.46410	0.53860	0.074 (15)*
H23	1.12300	0.64520	0.75490	0.0640*
H24	1.05520	0.32800	0.82800	0.0700*
H25	0.94790	0.02270	0.78710	0.0800*
H26	0.85880	−0.08790	0.65150	0.0840*
H27	0.86550	0.09280	0.55080	0.0730*
H31	0.04630	0.90190	0.02520	0.0730*
H33	0.11010	0.97010	0.25110	0.10 (2)*
H34	0.04250	0.61440	0.28480	0.0810*
H35	−0.03420	0.33520	0.21380	0.0940*
H36	−0.08290	0.29080	0.07420	0.0970*
H37	−0.04650	0.52480	−0.00210	0.0820*
H1A	0.23890	0.07600	0.36260	0.1910*
H1B	0.04880	0.12670	0.36090	0.1910*
H2A	0.30780	0.97330	0.46940	0.1850*
H2B	0.27160	0.79140	0.48810	0.1850*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0523 (3)	0.0539 (2)	0.0332 (2)	0.0160 (2)	0.0026 (2)	0.0071 (2)
Cl1	0.0959 (8)	0.0581 (5)	0.0467 (4)	−0.0033 (5)	0.0175 (5)	0.0019 (4)
Cl2	0.1015 (9)	0.0690 (6)	0.0423 (4)	0.0284 (6)	0.0096 (5)	−0.0074 (4)
Cl3	0.0682 (7)	0.1819 (15)	0.0594 (6)	0.0585 (9)	0.0058 (5)	0.0423 (7)
N1	0.0503 (16)	0.0458 (13)	0.0372 (12)	0.0171 (13)	0.0039 (12)	0.0076 (10)
N2	0.0596 (18)	0.0496 (14)	0.0389 (13)	0.0173 (14)	0.0029 (13)	0.0050 (11)
N3	0.0563 (18)	0.0541 (15)	0.0365 (12)	0.0166 (15)	0.0054 (13)	0.0034 (11)
C4	0.060 (2)	0.072 (2)	0.055 (2)	0.026 (2)	0.0196 (19)	0.0287 (19)
C5	0.066 (3)	0.061 (2)	0.088 (3)	0.024 (2)	0.030 (2)	0.038 (2)
C6	0.065 (3)	0.0468 (19)	0.093 (3)	0.0146 (19)	0.019 (2)	0.0109 (19)
C7	0.057 (2)	0.0533 (18)	0.0544 (19)	0.0098 (18)	0.0087 (18)	−0.0001 (15)
C8	0.0424 (17)	0.0504 (16)	0.0423 (15)	0.0161 (14)	0.0055 (14)	0.0084 (13)
C9	0.0431 (18)	0.0526 (16)	0.0426 (15)	0.0169 (15)	0.0089 (14)	0.0118 (13)
Co2	0.0625 (3)	0.0495 (2)	0.0336 (2)	0.0159 (2)	0.0033 (2)	0.0060 (2)
Cl4	0.1100 (10)	0.0605 (5)	0.0572 (5)	0.0355 (6)	−0.0038 (6)	0.0083 (4)
Cl5	0.1390 (14)	0.0598 (6)	0.0697 (7)	0.0027 (8)	−0.0386 (8)	−0.0015 (5)
Cl6	0.0837 (9)	0.1346 (11)	0.0667 (6)	0.0474 (9)	0.0314 (6)	0.0256 (7)
N11	0.0564 (17)	0.0426 (13)	0.0350 (11)	0.0145 (13)	0.0044 (12)	0.0038 (10)
N12	0.069 (2)	0.0467 (14)	0.0382 (13)	0.0191 (15)	0.0004 (14)	0.0000 (11)
N13	0.069 (2)	0.0590 (16)	0.0355 (12)	0.0233 (16)	0.0014 (14)	−0.0013 (11)
C14	0.061 (2)	0.077 (2)	0.0418 (17)	0.027 (2)	0.0099 (17)	0.0230 (17)
C15	0.067 (3)	0.073 (3)	0.062 (2)	0.029 (2)	0.017 (2)	0.035 (2)
C16	0.068 (3)	0.0489 (18)	0.069 (2)	0.0182 (19)	0.010 (2)	0.0174 (17)
C17	0.061 (2)	0.0456 (16)	0.0485 (18)	0.0161 (17)	0.0085 (17)	0.0057 (14)
C18	0.0440 (17)	0.0461 (15)	0.0353 (14)	0.0155 (14)	0.0053 (13)	0.0083 (11)
C19	0.048 (2)	0.0568 (18)	0.0362 (14)	0.0211 (16)	0.0094 (14)	0.0070 (13)
N21	0.065 (2)	0.0601 (17)	0.0392 (14)	0.0147 (16)	−0.0007 (15)	0.0087 (12)
N22	0.069 (2)	0.0514 (16)	0.0605 (19)	0.0148 (16)	−0.0018 (18)	0.0115 (14)
N23	0.0579 (19)	0.0524 (15)	0.0470 (15)	0.0168 (15)	−0.0020 (14)	−0.0018 (12)
C24	0.058 (2)	0.078 (2)	0.0472 (18)	0.028 (2)	0.0105 (18)	0.0202 (17)
C25	0.056 (2)	0.073 (3)	0.084 (3)	0.024 (2)	0.019 (2)	0.040 (2)
C26	0.055 (2)	0.0473 (19)	0.105 (4)	0.0122 (19)	0.005 (2)	0.011 (2)
C27	0.057 (2)	0.0491 (19)	0.071 (3)	0.0143 (18)	−0.003 (2)	−0.0047 (17)
C28	0.0429 (18)	0.0501 (17)	0.0452 (16)	0.0122 (15)	0.0032 (14)	0.0064 (13)
C29	0.0408 (18)	0.0527 (17)	0.0400 (15)	0.0162 (15)	0.0043 (14)	0.0044 (13)
N31	0.072 (3)	0.0657 (19)	0.0476 (16)	0.0224 (19)	0.0014 (17)	0.0150 (14)
N32	0.079 (3)	0.063 (2)	0.063 (2)	0.0251 (19)	0.0019 (19)	0.0135 (16)
N33	0.060 (2)	0.0635 (19)	0.0504 (17)	0.0182 (17)	0.0014 (15)	0.0054 (14)
C34	0.053 (2)	0.088 (3)	0.069 (3)	0.023 (2)	0.013 (2)	0.034 (2)
C35	0.069 (3)	0.066 (3)	0.109 (4)	0.019 (2)	0.019 (3)	0.036 (3)
C36	0.068 (3)	0.056 (2)	0.116 (4)	0.013 (2)	0.017 (3)	0.005 (2)
C37	0.069 (3)	0.070 (2)	0.065 (2)	0.016 (2)	0.011 (2)	−0.0019 (19)
C38	0.052 (2)	0.063 (2)	0.0476 (17)	0.0197 (18)	0.0068 (16)	0.0093 (15)
C39	0.045 (2)	0.0578 (18)	0.0526 (19)	0.0151 (17)	0.0035 (16)	0.0111 (15)
O1	0.161 (5)	0.126 (4)	0.074 (2)	0.015 (4)	0.002 (3)	−0.019 (2)
O2	0.187 (6)	0.111 (3)	0.065 (2)	0.033 (4)	0.016 (3)	−0.014 (2)

Geometric parameters (Å, º) top

Co1—Cl1	2.2649 (13)	C6—C7	1.371 (6)
Co1—Cl2	2.2616 (13)	C7—C8	1.403 (5)
Co1—Cl3	2.2195 (16)	C8—C9	1.392 (5)
Co1—N1	2.027 (3)	C4—H4	0.93
Co2—Cl4	2.2441 (13)	C5—H5	0.93
Co2—Cl5	2.2450 (15)	C6—H6	0.93
Co2—Cl6	2.2584 (16)	C7—H7	0.93
Co2—N11	2.022 (3)	C14—C15	1.355 (6)
O1—H1B	0.82	C14—C19	1.404 (5)
O1—H1A	0.82	C15—C16	1.419 (7)
N1—C8	1.371 (4)	C16—C17	1.361 (6)
N1—N2	1.320 (4)	C17—C18	1.399 (5)
N2—N3	1.332 (4)	C18—C19	1.397 (4)
N3—C9	1.360 (5)	C14—H14	0.93
O2—H2B	0.82	C15—H15	0.93
O2—H2A	0.82	C16—H16	0.93
N3—H3	0.86	C17—H17	0.93
N11—N12	1.320 (4)	C24—C25	1.378 (6)
N11—C18	1.373 (4)	C24—C29	1.393 (5)
N12—N13	1.332 (4)	C25—C26	1.409 (7)
N13—C19	1.354 (5)	C26—C27	1.352 (7)
N13—H13	0.86	C27—C28	1.407 (5)
N21—C28	1.359 (5)	C28—C29	1.386 (5)
N21—N22	1.311 (4)	C24—H24	0.93
N22—N23	1.309 (4)	C25—H25	0.93
N23—C29	1.363 (5)	C26—H26	0.93
N21—H21	0.86	C27—H27	0.93
N23—H23	0.86	C34—C39	1.407 (6)
N31—C38	1.366 (5)	C34—C35	1.350 (8)
N31—N32	1.310 (5)	C35—C36	1.403 (9)
N32—N33	1.316 (5)	C36—C37	1.358 (7)
N33—C39	1.349 (5)	C37—C38	1.388 (6)
N31—H31	0.86	C38—C39	1.388 (5)
N33—H33	0.86	C34—H34	0.93
C4—C5	1.365 (7)	C35—H35	0.93
C4—C9	1.398 (6)	C36—H36	0.93
C5—C6	1.405 (7)	C37—H37	0.93

Cl1—Co1—Cl2	106.81 (5)	C5—C6—H6	119
Cl1—Co1—Cl3	113.73 (7)	C8—C7—H7	122
Cl1—Co1—N1	106.87 (10)	C6—C7—H7	122
Cl2—Co1—Cl3	116.75 (6)	C15—C14—C19	115.9 (3)
Cl2—Co1—N1	105.84 (10)	C14—C15—C16	122.6 (4)
Cl3—Co1—N1	106.16 (11)	C15—C16—C17	121.8 (4)
Cl6—Co2—N11	102.70 (11)	C16—C17—C18	116.4 (3)
Cl4—Co2—Cl6	114.49 (6)	C17—C18—C19	121.4 (3)
Cl4—Co2—N11	110.22 (10)	N11—C18—C19	107.4 (3)
Cl4—Co2—Cl5	108.33 (6)	N11—C18—C17	131.2 (3)
Cl5—Co2—N11	109.56 (10)	N13—C19—C14	134.5 (3)
Cl5—Co2—Cl6	111.40 (7)	C14—C19—C18	121.8 (3)
H1A—O1—H1B	125	N13—C19—C18	103.7 (3)
N2—N1—C8	109.5 (3)	C15—C14—H14	122
Co1—N1—N2	118.5 (2)	C19—C14—H14	122
Co1—N1—C8	131.9 (2)	C16—C15—H15	119
N1—N2—N3	107.4 (3)	C14—C15—H15	119
N2—N3—C9	111.5 (3)	C15—C16—H16	119
H2A—O2—H2B	124	C17—C16—H16	119
C9—N3—H3	124	C18—C17—H17	122
N2—N3—H3	124	C16—C17—H17	122
N12—N11—C18	109.6 (3)	C25—C24—C29	115.7 (3)
Co2—N11—N12	120.6 (2)	C24—C25—C26	121.3 (4)
Co2—N11—C18	129.7 (2)	C25—C26—C27	123.6 (4)
N11—N12—N13	106.7 (3)	C26—C27—C28	115.4 (4)
N12—N13—C19	112.7 (3)	N21—C28—C29	104.7 (3)
N12—N13—H13	124	N21—C28—C27	133.7 (3)
C19—N13—H13	124	C27—C28—C29	121.6 (4)
N22—N21—C28	113.5 (3)	C24—C29—C28	122.5 (4)
N21—N22—N23	104.1 (3)	N23—C29—C24	133.3 (3)
N22—N23—C29	113.6 (3)	N23—C29—C28	104.3 (3)
C28—N21—H21	123	C29—C24—H24	122
N22—N21—H21	123	C25—C24—H24	122
N22—N23—H23	123	C24—C25—H25	119
C29—N23—H23	123	C26—C25—H25	119
N32—N31—C38	112.6 (3)	C25—C26—H26	118
N31—N32—N33	105.2 (3)	C27—C26—H26	118
N32—N33—C39	112.3 (3)	C28—C27—H27	122
C38—N31—H31	124	C26—C27—H27	122
N32—N31—H31	124	C35—C34—C39	115.8 (5)
C39—N33—H33	124	C34—C35—C36	122.5 (5)
N32—N33—H33	124	C35—C36—C37	122.5 (5)
C5—C4—C9	116.0 (4)	C36—C37—C38	115.8 (5)
C4—C5—C6	122.1 (4)	N31—C38—C39	104.2 (3)
C5—C6—C7	122.2 (4)	N31—C38—C37	133.7 (4)
C6—C7—C8	116.4 (3)	C37—C38—C39	122.1 (4)
N1—C8—C9	107.2 (3)	C34—C39—C38	121.3 (4)
N1—C8—C7	131.9 (3)	N33—C39—C34	133.0 (4)
C7—C8—C9	120.9 (3)	N33—C39—C38	105.7 (3)
N3—C9—C8	104.5 (3)	C35—C34—H34	122
N3—C9—C4	133.1 (3)	C39—C34—H34	122
C4—C9—C8	122.4 (4)	C36—C35—H35	119
C5—C4—H4	122	C34—C35—H35	119
C9—C4—H4	122	C35—C36—H36	119
C6—C5—H5	119	C37—C36—H36	119
C4—C5—H5	119	C38—C37—H37	122
C7—C6—H6	119	C36—C37—H37	122

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···Cl6	0.82	2.79	3.279 (5)	120
O2—H2A···O1ⁱ	0.82	2.41	3.142 (7)	148
O2—H2B···Cl6	0.82	2.52	3.295 (5)	159
N3—H3···O2ⁱⁱ	0.86	1.87	2.721 (4)	173
N13—H13···Cl2ⁱⁱⁱ	0.86	2.28	3.127 (3)	169
N21—H21···Cl4	0.86	2.80	3.458 (4)	134
N21—H21···Cl6^iv	0.86	2.75	3.316 (4)	125
N23—H23···Cl1^v	0.86	2.30	3.123 (3)	160
N31—H31···Cl3^vi	0.86	2.61	3.214 (4)	128
N33—H33···O1ⁱ	0.86	1.79	2.646 (5)	170

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

Experimental details

Crystal data
Chemical formula	(C₆H₆N₃)[CoCl₃(C₆H₅N₃)]·H₂O
M_r	422.56
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.8760 (8), 7.8033 (12), 16.657 (3)
α, β, γ (°)	95.450 (13), 95.962 (8), 103.989 (9)
V (Å³)	855.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.48
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Bruker P4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.611, 0.744
No. of measured, independent and observed [I > 2σ(I)] reflections	4906, 4846, 4526
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.078, 1.08
No. of reflections	4846
No. of parameters	417
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.26
Absolute structure	Flack (1983), 920 Friedel pairs
Absolute structure parameter	−0.008 (13)

Computer programs: XSCANS (Bruker, 1997), SHELXTL (Bruker, 2003), PLATON (Spek, 2003).

Selected bond lengths (Å) top

Co1—Cl1	2.2649 (13)	Co2—Cl4	2.2441 (13)
Co1—Cl2	2.2616 (13)	Co2—Cl5	2.2450 (15)
Co1—Cl3	2.2195 (16)	Co2—Cl6	2.2584 (16)
Co1—N1	2.027 (3)	Co2—N11	2.022 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···Cl6	0.82	2.79	3.279 (5)	120
O2—H2A···O1ⁱ	0.82	2.41	3.142 (7)	148
O2—H2B···Cl6	0.82	2.52	3.295 (5)	159
N3—H3···O2ⁱⁱ	0.86	1.87	2.721 (4)	173
N13—H13···Cl2ⁱⁱⁱ	0.86	2.28	3.127 (3)	169
N21—H21···Cl4	0.86	2.80	3.458 (4)	134
N21—H21···Cl6^iv	0.86	2.75	3.316 (4)	125
N23—H23···Cl1^v	0.86	2.30	3.123 (3)	160
N31—H31···Cl3^vi	0.86	2.61	3.214 (4)	128
N33—H33···O1ⁱ	0.86	1.79	2.646 (5)	170

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

References

Bruker (1997). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hahn, F. E., Scharn, D. & Lugger, T. (1997). Z. Kristallogr. New Cryst. Struct. 212, 472. Google Scholar
Krawczyk, S. & Gdaniec, M. (2005). Acta Cryst. E61, o2967–o2969. Web of Science CSD CrossRef IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Pan, T.-T. & Xu, D.-J. (2004). Acta Cryst. E60, m56–m58. CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z.-F., Li, L.-X., Wang, X.-Q., Xie, C.-Z., Wang, R.-J. & Shen, G.-Q. (2004). Acta Cryst. E60, m498–m500. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, G., Yang, G., Wu, N. & Ma, J. S. (2006). Cryst. Growth Des. 6, 229–234. Web of Science CSD CrossRef Google Scholar

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