Aqua­(2,2′-diamino-4,4′-bi-1,3-thia­zole-κ2N,N′)(pyridine-2,6-dicarboxyl­ato-κ3O,N,O′)cobalt(II) tetra­hydrate

Wei, C.-E.; Chen, G.-H.; Liu, B.-X.

doi:10.1107/S1600536807029595

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Aqua(2,2′-diamino-4,4′-bi-1,3-thiazole-κ²N,N′)(pyridine-2,6-dicarboxylato-κ³O,N,O′)cobalt(II) tetrahydrate

C.-E. Wei, G.-H. Chen and B.-X. Liu

The structure of the title complex, [Co(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O, displays a distorted octahedral coordination geometry around the Co^II center, formed by a diaminobithiazole molecule (DABT), one pyridine-2,6-dicarboxylate anion and one water molecule. The pyridine-2,6-dicarboxylate anion chelates the Co^II ion with a facial configuration. Within the chelating DABT ligand, the thiazole rings are twisted with respect to each other [dihedral angle 15.10 (5)°]. Uncoordinated water molecules are involved in O—H

O and N—H

O hydrogen bonds, with H

O separations in the range 1.88–2.17 Å, stabilizing the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029595/bh2116sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029595/bh2116Isup2.hkl Contains datablock I

CCDC reference: 654800

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R factor = 0.048
wR factor = 0.112
Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S11    in Main Residue .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H2 O

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co          (2)       1.67

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Transition metal complexes of 2,2'-diamino-4,4'-bi-1,3-thiazole (DABT) have shown potential applications in the field of soft magnetic materials (Sun et al., 1997). As a part of a serial structural investigation of metal complexes with DABT (Liu et al., 2003), the title Co^II complex was recently prepared and its X-ray structure is presented here.

The molecular structure of the title compound is shown in Fig. 1. The complex has a distorted octahedral coordination geometry formed by one DABT ligand, one pyridine-2,6-dicarboxylate anion and one water molecule. The asymmetric unit is completed with four lattice water molecules.

Thiazole rings of DABT are not coplanar, as observed in other complexes we have reported. The dihedral angle between thiazole rings is 15.10 (5) °, the rings being defined as C11/C12/C13/S11/N11 and C14/C15/C16/S12/N13. This angle is similar to the dihedral angle of 17.23 (7)° found in [Cr(C₄H₅NO₄)(C₆H₆N₄S₂)(H₂O)]Cl.H₂O, (Liu & Xu, 2004). Bond lengths C16—N14 [1.335 (4) Å] and C16—N13 [1.324 (4) Å] imply the existence of electron delocalization between thiazole rings and amino groups. This feature for DABT can be found in other DABT complexes based on Mn^II (Liu & Xu, 2005) and Co^II (Liu, Yu & Xu, 2005) we have reported. Other DABT complexes have been reported (Liu et al., 2006; Zhang et al., 2006).

The tridentate pyridine-2,6-dicarboxylate anion chelates to the Co^II ion with a facial configuration (Ma et al., 2002). The maximum deviation from the mean plane defined by C21···C27/N21/O21···O24 is 0.082 (3) Å, for atom N21.

The extensive hydrogen bonding scheme involving lattice water molecules and complex helps to stabilize the crystal structure, as shown in Fig. 1. and Table reporting intermolecular contacts..

Related literature top

For general background, see Liu et al. (2006); For synthesis see Zhang et al. (2006). For related structures see: Liu & Xu (2004, 2005); Liu et al. (2003, 2005); Sun et al. (1997), Ma et al. (2002).

Experimental top

The complex was prepared following a procedure similar to that previously used for a Ni^II compound (Zhang et al., 2006). An aqueous solution (20 ml) containing DABT (1 mmol) and CoCl₂ (1 mmol) was mixed with an aqueous solution (10 ml) of pyridine-2,6-dicarboxylic acid (1 mmol) and NaOH (2 mmol). The mixture was refluxed for 5 h. After cooling to room temperature the solution was filtered. Red single crystals of the title complex were obtained from the filtrate after 30 d.

Structure description top

The extensive hydrogen bonding scheme involving lattice water molecules and complex helps to stabilize the crystal structure, as shown in Fig. 1. and Table reporting intermolecular contacts..

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title complex with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). Dashed lines show the hydrogen bonds [symmetry code: (i) x - 1, y, z].

Aqua(2,2'-diamino-4,4'-bi-1,3-thiazole-κ²N,N')(pyridine- 2,6-dicarboxylato-κ³O,N,O')cobalt(II) tetrahydrate top

Crystal data top

[Co(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O	F(000) = 1052
M_r = 512.38	D_x = 1.734 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4380 reflections
a = 10.0259 (15) Å	θ = 2.0–27.5°
b = 7.0956 (11) Å	µ = 1.15 mm⁻¹
c = 27.648 (4) Å	T = 295 K
β = 93.528 (2)°	Prism, red
V = 1963.2 (5) Å³	0.26 × 0.20 × 0.15 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4488 independent reflections
Radiation source: fine-focus sealed tube	2781 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −12→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −7→9
T_min = 0.76, T_max = 0.84	l = −34→35
11819 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.041P)²] where P = (F_o² + 2F_c²)/3
4488 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Co(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O	V = 1963.2 (5) Å³
M_r = 512.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0259 (15) Å	µ = 1.15 mm⁻¹
b = 7.0956 (11) Å	T = 295 K
c = 27.648 (4) Å	0.26 × 0.20 × 0.15 mm
β = 93.528 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4488 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2781 reflections with I > 2σ(I)
T_min = 0.76, T_max = 0.84	R_int = 0.058
11819 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	Δρ_max = 0.39 e Å⁻³
4488 reflections	Δρ_min = −0.53 e Å⁻³
271 parameters

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

	x	y	z	U_iso*/U_eq
Co	0.70981 (5)	0.52542 (7)	0.673116 (16)	0.02505 (15)
N11	0.5102 (3)	0.5782 (4)	0.69340 (9)	0.0249 (7)
N12	0.3703 (3)	0.5793 (5)	0.62170 (11)	0.0416 (9)
H12A	0.4206	0.5889	0.5964	0.050*
H12B	0.2843	0.5756	0.6136	0.050*
N13	0.7381 (3)	0.5238 (4)	0.74861 (9)	0.0246 (7)
N14	0.9684 (3)	0.4777 (5)	0.76659 (11)	0.0393 (8)
H14A	0.9778	0.4265	0.7394	0.050*
H14B	1.0317	0.4637	0.7900	0.050*
N21	0.7092 (3)	0.6023 (4)	0.60086 (9)	0.0238 (7)
O1	0.9027 (2)	0.3886 (3)	0.66627 (8)	0.0322 (6)
H1A	0.9571	0.4446	0.6511	0.048*
H1B	0.8962	0.2837	0.6563	0.048*
O21	0.8075 (2)	0.8037 (3)	0.67166 (8)	0.0318 (6)
O22	0.8782 (2)	1.0307 (3)	0.62364 (9)	0.0349 (6)
O23	0.6270 (2)	0.2834 (3)	0.63337 (8)	0.0315 (6)
O24	0.5645 (3)	0.1782 (4)	0.55884 (9)	0.0449 (7)
O1W	0.4090 (3)	−0.1295 (4)	0.54364 (10)	0.0501 (8)
H1WA	0.4614	−0.0438	0.5535	0.075*
H1WB	0.4072	−0.1294	0.5134	0.075*
O2W	0.9974 (3)	0.2014 (4)	0.55043 (9)	0.0520 (8)
H2WA	0.9544	0.1987	0.5232	0.078*
H2WB	0.9475	0.1632	0.5717	0.078*
O3W	1.0712 (3)	0.5351 (4)	0.59782 (10)	0.0482 (7)
H3WA	1.0734	0.6325	0.5828	0.072*
H3WB	1.0465	0.4509	0.5799	0.072*
O4W	1.1338 (3)	0.8492 (4)	0.54165 (9)	0.0470 (7)
H4WA	1.2153	0.8601	0.5443	0.070*
H4WB	1.0993	0.9507	0.5499	0.070*
S11	0.26088 (9)	0.55446 (15)	0.70815 (4)	0.0358 (3)
S12	0.80820 (10)	0.54847 (16)	0.83941 (3)	0.0378 (3)
C11	0.4991 (4)	0.5664 (5)	0.74335 (12)	0.0263 (8)
C12	0.3732 (4)	0.5532 (5)	0.75708 (13)	0.0329 (9)
H12	0.3502	0.5446	0.7891	0.039*
C13	0.3914 (4)	0.5722 (5)	0.67035 (13)	0.0293 (8)
C14	0.6233 (3)	0.5582 (5)	0.77352 (12)	0.0268 (8)
C15	0.6420 (4)	0.5770 (5)	0.82163 (13)	0.0332 (9)
H15	0.5748	0.6020	0.8425	0.040*
C16	0.8444 (4)	0.5117 (5)	0.77936 (12)	0.0274 (8)
C21	0.7622 (3)	0.7664 (5)	0.58793 (12)	0.0246 (8)
C22	0.7694 (4)	0.8154 (5)	0.53997 (12)	0.0324 (9)
H22	0.8062	0.9302	0.5315	0.039*
C23	0.7210 (4)	0.6913 (6)	0.50479 (13)	0.0363 (9)
H23	0.7231	0.7225	0.4722	0.044*
C24	0.6693 (4)	0.5201 (5)	0.51834 (13)	0.0332 (9)
H24	0.6381	0.4337	0.4950	0.040*
C25	0.6647 (3)	0.4792 (5)	0.56717 (12)	0.0249 (8)
C26	0.6130 (4)	0.2984 (5)	0.58774 (13)	0.0298 (8)
C27	0.8201 (3)	0.8784 (5)	0.63080 (13)	0.0269 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.0258 (3)	0.0284 (3)	0.0209 (3)	−0.0019 (2)	0.00102 (19)	0.0000 (2)
N11	0.0250 (17)	0.0282 (18)	0.0219 (15)	−0.0007 (12)	0.0037 (12)	0.0019 (13)
N12	0.0281 (18)	0.069 (3)	0.0275 (17)	0.0025 (16)	−0.0039 (14)	−0.0014 (17)
N13	0.0236 (16)	0.0279 (17)	0.0222 (15)	−0.0020 (13)	0.0008 (12)	0.0033 (13)
N14	0.0272 (18)	0.063 (2)	0.0273 (17)	0.0008 (16)	−0.0065 (13)	−0.0040 (16)
N21	0.0253 (16)	0.0238 (17)	0.0221 (15)	−0.0044 (12)	−0.0006 (12)	−0.0020 (13)
O1	0.0344 (15)	0.0291 (15)	0.0330 (14)	0.0013 (11)	0.0023 (11)	−0.0048 (12)
O21	0.0390 (16)	0.0353 (16)	0.0209 (13)	−0.0092 (12)	−0.0005 (11)	−0.0014 (12)
O22	0.0403 (16)	0.0300 (15)	0.0341 (15)	−0.0124 (12)	0.0012 (12)	−0.0024 (12)
O23	0.0394 (16)	0.0256 (14)	0.0295 (14)	−0.0043 (11)	0.0039 (11)	0.0027 (12)
O24	0.0606 (19)	0.0334 (16)	0.0397 (16)	−0.0197 (14)	−0.0044 (14)	−0.0087 (14)
O1W	0.062 (2)	0.0436 (18)	0.0450 (17)	−0.0232 (15)	0.0053 (14)	−0.0062 (15)
O2W	0.058 (2)	0.060 (2)	0.0384 (16)	−0.0206 (16)	0.0055 (14)	−0.0009 (15)
O3W	0.0499 (18)	0.0456 (18)	0.0491 (18)	−0.0084 (14)	0.0023 (14)	0.0041 (15)
O4W	0.0489 (18)	0.0468 (18)	0.0451 (17)	−0.0039 (14)	0.0018 (14)	0.0022 (14)
S11	0.0258 (5)	0.0401 (6)	0.0420 (6)	−0.0004 (4)	0.0045 (4)	−0.0018 (5)
S12	0.0423 (6)	0.0492 (7)	0.0214 (5)	−0.0010 (5)	−0.0027 (4)	−0.0007 (5)
C11	0.032 (2)	0.0211 (19)	0.0265 (19)	−0.0015 (15)	0.0054 (15)	0.0001 (15)
C12	0.032 (2)	0.037 (2)	0.030 (2)	0.0015 (17)	0.0068 (16)	0.0007 (18)
C13	0.028 (2)	0.033 (2)	0.027 (2)	0.0002 (16)	0.0000 (16)	−0.0020 (17)
C14	0.031 (2)	0.025 (2)	0.0254 (19)	−0.0041 (16)	0.0038 (15)	0.0015 (16)
C15	0.033 (2)	0.040 (2)	0.027 (2)	0.0002 (17)	0.0027 (16)	−0.0010 (18)
C16	0.031 (2)	0.027 (2)	0.0235 (18)	−0.0018 (16)	−0.0027 (15)	0.0025 (16)
C21	0.0219 (18)	0.024 (2)	0.0277 (19)	−0.0013 (15)	0.0001 (15)	−0.0019 (16)
C22	0.040 (2)	0.029 (2)	0.028 (2)	−0.0080 (17)	−0.0019 (17)	0.0065 (17)
C23	0.049 (3)	0.041 (2)	0.0189 (19)	−0.0058 (19)	−0.0007 (17)	0.0024 (18)
C24	0.043 (2)	0.033 (2)	0.0228 (19)	−0.0084 (18)	0.0011 (16)	−0.0070 (17)
C25	0.0285 (19)	0.0220 (19)	0.0237 (18)	−0.0005 (15)	−0.0006 (14)	−0.0003 (15)
C26	0.029 (2)	0.031 (2)	0.029 (2)	−0.0037 (16)	0.0025 (16)	0.0000 (17)
C27	0.025 (2)	0.026 (2)	0.029 (2)	−0.0039 (15)	0.0016 (15)	−0.0050 (17)

Geometric parameters (Å, º) top

Co—N21	2.070 (3)	O1W—H1WB	0.8346
Co—N13	2.089 (3)	O2W—H2WA	0.8437
Co—N11	2.144 (3)	O2W—H2WB	0.8397
Co—O23	2.176 (2)	O3W—H3WA	0.8077
Co—O1	2.182 (2)	O3W—H3WB	0.8042
Co—O21	2.206 (2)	O4W—H4WA	0.8198
N11—C13	1.316 (4)	O4W—H4WB	0.8369
N11—C11	1.395 (4)	S11—C12	1.706 (4)
N12—C13	1.350 (4)	S11—C13	1.729 (4)
N12—H12A	0.8902	S12—C15	1.720 (4)
N12—H12B	0.8774	S12—C16	1.741 (3)
N13—C16	1.324 (4)	C11—C12	1.344 (5)
N13—C14	1.399 (4)	C11—C14	1.457 (5)
N14—C16	1.335 (4)	C12—H12	0.9300
N14—H14A	0.8454	C14—C15	1.338 (5)
N14—H14B	0.8832	C15—H15	0.9300
N21—C25	1.334 (4)	C21—C22	1.377 (4)
N21—C21	1.338 (4)	C21—C27	1.513 (4)
O1—H1A	0.8126	C22—C23	1.379 (5)
O1—H1B	0.7954	C22—H22	0.9300
O21—C27	1.261 (4)	C23—C24	1.381 (5)
O22—C27	1.250 (4)	C23—H23	0.9300
O23—C26	1.265 (4)	C24—C25	1.385 (5)
O24—C26	1.247 (4)	C24—H24	0.9300
O1W—H1WA	0.8383	C25—C26	1.508 (5)

N21—Co—N13	163.25 (11)	C15—S12—C16	90.01 (17)
N21—Co—N11	105.01 (11)	C12—C11—N11	114.7 (3)
N13—Co—N11	79.13 (10)	C12—C11—C14	128.3 (3)
N21—Co—O23	75.06 (10)	N11—C11—C14	116.8 (3)
N13—Co—O23	121.63 (10)	C11—C12—S11	111.2 (3)
N11—Co—O23	86.38 (10)	C11—C12—H12	124.4
N21—Co—O1	89.05 (10)	S11—C12—H12	124.4
N13—Co—O1	91.00 (10)	N11—C13—N12	124.3 (3)
N11—Co—O1	161.20 (10)	N11—C13—S11	113.9 (3)
O23—Co—O1	85.27 (9)	N12—C13—S11	121.8 (3)
N21—Co—O21	73.83 (10)	C15—C14—N13	116.0 (3)
N13—Co—O21	89.42 (10)	C15—C14—C11	128.9 (3)
N11—Co—O21	105.71 (10)	N13—C14—C11	115.2 (3)
O23—Co—O21	148.60 (9)	C14—C15—S12	110.2 (3)
O1—Co—O21	90.00 (9)	C14—C15—H15	124.9
C13—N11—C11	110.6 (3)	S12—C15—H15	124.9
C13—N11—Co	134.3 (2)	N13—C16—N14	124.6 (3)
C11—N11—Co	112.4 (2)	N13—C16—S12	113.3 (3)
C13—N12—H12A	136.5	N14—C16—S12	122.1 (3)
C13—N12—H12B	110.3	N21—C21—C22	121.5 (3)
H12A—N12—H12B	113.3	N21—C21—C27	112.8 (3)
C16—N13—C14	110.4 (3)	C22—C21—C27	125.6 (3)
C16—N13—Co	134.1 (2)	C21—C22—C23	118.7 (3)
C14—N13—Co	115.2 (2)	C21—C22—H22	120.6
C16—N14—H14A	118.0	C23—C22—H22	120.6
C16—N14—H14B	117.7	C22—C23—C24	119.5 (3)
H14A—N14—H14B	119.3	C22—C23—H23	120.3
C25—N21—C21	120.3 (3)	C24—C23—H23	120.3
C25—N21—Co	118.8 (2)	C23—C24—C25	119.0 (3)
C21—N21—Co	120.6 (2)	C23—C24—H24	120.5
Co—O1—H1A	117.0	C25—C24—H24	120.5
Co—O1—H1B	113.1	N21—C25—C24	120.9 (3)
H1A—O1—H1B	108.7	N21—C25—C26	113.7 (3)
C27—O21—Co	117.5 (2)	C24—C25—C26	125.4 (3)
C26—O23—Co	116.9 (2)	O24—C26—O23	126.6 (3)
H1WA—O1W—H1WB	107.5	O24—C26—C25	118.0 (3)
H2WA—O2W—H2WB	108.8	O23—C26—C25	115.3 (3)
H3WA—O3W—H3WB	109.6	O22—C27—O21	125.4 (3)
H4WA—O4W—H4WB	108.7	O22—C27—C21	119.4 (3)
C12—S11—C13	89.57 (17)	O21—C27—C21	115.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3W	0.81	2.02	2.812 (4)	163
O1—H1B···O22ⁱ	0.80	2.01	2.804 (3)	174
O1W—H1WA···O24	0.84	1.88	2.701 (4)	164
O1W—H1WB···O24ⁱⁱ	0.84	2.06	2.883 (4)	167
O2W—H2WA···O4Wⁱⁱⁱ	0.84	1.98	2.816 (4)	171
O2W—H2WB···O22ⁱ	0.84	1.88	2.700 (4)	163
O3W—H3WA···O4W	0.81	2.03	2.809 (4)	163
O3W—H3WB···O2W	0.81	2.00	2.784 (4)	165
O4W—H4WA···O1W^iv	0.82	1.94	2.760 (4)	173
O4W—H4WB···O2W^v	0.84	2.05	2.866 (4)	164
N12—H12A···O1W^v	0.89	2.47	3.030 (4)	121
N12—H12B···O3W^vi	0.88	2.17	3.047 (4)	173
N14—H14A···O1	0.85	2.13	2.881 (4)	148
N14—H14B···O21^vii	0.88	2.19	3.003 (4)	152
N14—H14B···O22^vii	0.88	2.55	3.338 (4)	150

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

Experimental details

Crystal data
Chemical formula	[Co(C₇H₃NO₄)(C₆H₆N₄S₂)(H₂O)]·4H₂O
M_r	512.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.0259 (15), 7.0956 (11), 27.648 (4)
β (°)	93.528 (2)
V (Å³)	1963.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.26 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.76, 0.84
No. of measured, independent and observed [I > 2σ(I)] reflections	11819, 4488, 2781
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.112, 1.01
No. of reflections	4488
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.53

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3W	0.81	2.02	2.812 (4)	163
O1—H1B···O22ⁱ	0.80	2.01	2.804 (3)	174
O1W—H1WA···O24	0.84	1.88	2.701 (4)	164
O1W—H1WB···O24ⁱⁱ	0.84	2.06	2.883 (4)	167
O2W—H2WA···O4Wⁱⁱⁱ	0.84	1.98	2.816 (4)	171
O2W—H2WB···O22ⁱ	0.84	1.88	2.700 (4)	163
O3W—H3WA···O4W	0.81	2.03	2.809 (4)	163
O3W—H3WB···O2W	0.81	2.00	2.784 (4)	165
O4W—H4WA···O1W^iv	0.82	1.94	2.760 (4)	173
O4W—H4WB···O2W^v	0.84	2.05	2.866 (4)	164
N12—H12B···O3W^vi	0.88	2.17	3.047 (4)	173

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

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