μ-Oxalato-bis-[(2,2'-bipyridyl)-copper(II)] bis(perchlorate) dimethyl-formamide disolvate monohydrate.

The title compound, [Cu(2)(C(2)O(4))(C(10)H(8)N(2))(4)](ClO(4))(2)·2C(3)H(7)NO·H(2)O, contains doubly charged centrosymmetric dinuclear oxalato-bridged copper(II) complex cations, perchlorate anions, and DMF and water solvate mol-ecules. In the complex cation, the oxalate ligand is coordinated in a bis-bidentate bridging mode to the Cu atoms. Each Cu atom has a distorted tetra-gonal-bipyramidal environment, being coordinated by two N atoms of the two chelating bipy ligands and two O atoms of the doubly deprotonated oxalate anion. Pairs of perchlorate anions and water mol-ecules are linked into recta-ngles by O-H⋯O bonds in which the perchlorate O atoms act as acceptors and the water mol-ecules as donors. Methyl groups of the DMF solvent molecule are disordered over two sites with occupancies of 0.453 (7):0.547 (7), and the water molecule is half-occupied.

Related literature

For use of oxalic acid and its derivatives in mol­ecular magnetism and supra­molecular chemistry, see: Kahn (1987 ▶); Ojima & Nonoyama (1988 ▶); Fritsky et al. (1998 ▶); Świątek-Kozłowska et al. (2000 ▶). For use of oxalic acid for the preparation of mixed-ligand polynuclear complexes, see: Strotmeyer et al. (2003 ▶). For related structures, see: Krämer & Fritsky (2000 ▶); Kovbasyuk et al. (2004 ▶); Wörl et al. (2005 ▶); Tomyn et al. (2007 ▶); Moroz et al. (2010 ▶).

Experimental

Crystal data

[Cu2(C2O4)(C10n class="Species">H8N2)4](ClO4)2·2C3H7NO·H2O

M = 1202.94

Triclinic,

a = 9.6872 (5) Å

b = 11.0080 (8) Å

c = 12.2449 (5) Å

α = 97.928 (3)°

β = 99.565 (2)°

γ = 91.924 (2)°

V = 1273.16 (12) Å3

Z = 1

Mo Kα radiation

μ = 1.02 mm−1

T = 100 K

0.23 × 0.12 × 0.08 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.802, T max = 0.923

10051 measured reflections

4993 independent reflections

3955 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.04

4993 reflections

359 parameters

27 restraints

H-atom parameters constrained

Δρmax = 1.43 e Å−3

Δρmin = −0.70 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Bradenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031569/jh2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031569/jh2192Isup2.hkl

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

[Cu2(C2O4)(C10H8N2)4](ClO4)2·2C3H7NO·H2O	Z = 1
Mr = 1202.94	F(000) = 618
Triclinic, P1	Dx = 1.569 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6872 (5) Å	Cell parameters from 3860 reflections
b = 11.0080 (8) Å	θ = 2.3–27.4°
c = 12.2449 (5) Å	µ = 1.02 mm−1
α = 97.928 (3)°	T = 100 K
β = 99.565 (2)°	Block, turquoise
γ = 91.924 (2)°	0.23 × 0.12 × 0.08 mm
V = 1273.16 (12) Å3

Bruker Kappa APEXII DUO CCD diffractometer	4993 independent reflections
Radiation source: fine-focus sealed tube	3955 reflections with I > 2σ(I)
curved graphite crystal	Rint = 0.023
Detector resolution: 16 pixels mm-1	θmax = 26.0°, θmin = 1.7°
φ scans and ω scans with κ offset	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.802, Tmax = 0.923	l = −10→15
10051 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0663P)2 + 2.0663P] where P = (Fo2 + 2Fc2)/3
4993 reflections	(Δ/σ)max < 0.001
359 parameters	Δρmax = 1.43 e Å−3
27 restraints	Δρmin = −0.70 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.29558 (4)	0.30820 (4)	0.41931 (4)	0.01694 (15)
Cl1	0.71283 (9)	0.33716 (9)	0.90518 (8)	0.0256 (2)
O1	0.5313 (3)	0.3455 (2)	0.5049 (2)	0.0206 (6)
O2	0.3249 (2)	0.4898 (2)	0.4286 (2)	0.0176 (5)
O3	0.7943 (4)	0.3548 (3)	0.8209 (3)	0.0517 (9)
O4	0.7375 (3)	0.2198 (3)	0.9423 (3)	0.0351 (7)
O5	0.7470 (4)	0.4320 (3)	0.9976 (3)	0.0534 (10)
O6	0.5683 (3)	0.3377 (4)	0.8567 (3)	0.0523 (10)
O7	0.3074 (6)	0.0419 (7)	0.7731 (7)	0.138 (3)
N1	0.3182 (3)	0.1260 (3)	0.4105 (3)	0.0199 (7)
N2	0.3572 (3)	0.2758 (3)	0.2693 (3)	0.0176 (6)
N3	0.0654 (3)	0.3071 (3)	0.3574 (3)	0.0190 (6)
N4	0.2160 (3)	0.3330 (3)	0.5640 (3)	0.0177 (6)
N5	0.0955 (5)	0.0617 (5)	0.7989 (5)	0.0720 (17)
C1	0.2978 (4)	0.0562 (4)	0.4883 (4)	0.0293 (9)
H1	0.2670	0.0932	0.5542	0.035*
C2	0.3199 (4)	−0.0685 (4)	0.4759 (4)	0.0321 (10)
H2	0.3052	−0.1160	0.5325	0.039*
C3	0.3636 (4)	−0.1221 (3)	0.3802 (4)	0.0287 (9)
H3	0.3776	−0.2076	0.3694	0.034*
C4	0.3870 (4)	−0.0508 (3)	0.3001 (4)	0.0256 (8)
H4	0.4179	−0.0863	0.2338	0.031*
C5	0.3646 (3)	0.0738 (3)	0.3182 (3)	0.0186 (7)
C6	0.3871 (3)	0.1588 (3)	0.2378 (3)	0.0180 (7)
C7	0.4363 (4)	0.1248 (4)	0.1392 (3)	0.0269 (9)
H7	0.4560	0.0418	0.1176	0.032*
C8	0.4568 (4)	0.2125 (4)	0.0723 (3)	0.0292 (9)
H8	0.4916	0.1906	0.0045	0.035*
C9	0.4265 (4)	0.3320 (4)	0.1045 (3)	0.0267 (9)
H9	0.4406	0.3939	0.0599	0.032*
C10	0.3753 (4)	0.3601 (3)	0.2029 (3)	0.0233 (8)
H10	0.3520	0.4421	0.2245	0.028*
C11	−0.0050 (4)	0.2868 (4)	0.2522 (3)	0.0259 (8)
H11	0.0470	0.2737	0.1928	0.031*
C12	−0.1495 (4)	0.2839 (4)	0.2259 (4)	0.0279 (9)
H12	−0.1961	0.2686	0.1503	0.033*
C13	−0.2244 (4)	0.3038 (4)	0.3131 (4)	0.0275 (9)
H13	−0.3239	0.3025	0.2979	0.033*
C14	−0.1538 (4)	0.3256 (3)	0.4223 (3)	0.0210 (8)
H14	−0.2038	0.3397	0.4829	0.025*
C15	−0.0077 (4)	0.3266 (3)	0.4419 (3)	0.0177 (7)
C16	0.0767 (4)	0.3479 (3)	0.5566 (3)	0.0177 (7)
C17	0.0176 (4)	0.3815 (3)	0.6520 (3)	0.0233 (8)
H17	−0.0802	0.3919	0.6458	0.028*
C18	0.1027 (4)	0.3992 (4)	0.7553 (3)	0.0274 (9)
H18	0.0641	0.4226	0.8209	0.033*
C19	0.2450 (4)	0.3828 (4)	0.7632 (3)	0.0273 (9)
H19	0.3052	0.3939	0.8339	0.033*
C20	0.2973 (4)	0.3496 (3)	0.6654 (3)	0.0218 (8)
H20	0.3947	0.3381	0.6703	0.026*
C21	0.5591 (4)	0.4576 (3)	0.5219 (3)	0.0168 (7)
C22A	0.0103 (10)	0.0664 (11)	0.7051 (11)	0.049 (2)	0.453 (7)
H22A	−0.0851	0.0770	0.7202	0.074*	0.453 (7)
H22B	0.0119	−0.0101	0.6540	0.074*	0.453 (7)
H22C	0.0402	0.1359	0.6707	0.074*	0.453 (7)
C23A	0.075 (2)	0.1244 (19)	0.9138 (14)	0.107 (4)	0.453 (7)
H23A	−0.0240	0.1429	0.9113	0.161*	0.453 (7)
H23B	0.1336	0.2010	0.9343	0.161*	0.453 (7)
H23C	0.1010	0.0697	0.9696	0.161*	0.453 (7)
C22B	0.0510 (8)	0.0191 (9)	0.6636 (8)	0.049 (2)	0.547 (7)
H22D	−0.0497	0.0275	0.6410	0.074*	0.547 (7)
H22E	0.0726	−0.0668	0.6447	0.074*	0.547 (7)
H22F	0.1036	0.0711	0.6241	0.074*	0.547 (7)
C23B	−0.0322 (15)	0.1000 (16)	0.8376 (15)	0.107 (4)	0.547 (7)
H23D	−0.1106	0.0875	0.7745	0.161*	0.547 (7)
H23E	−0.0206	0.1872	0.8694	0.161*	0.547 (7)
H23F	−0.0517	0.0512	0.8950	0.161*	0.547 (7)
C24	0.2302 (8)	0.0497 (10)	0.8262 (7)	0.100 (3)
H24	0.2637	0.0475	0.9034	0.121*
O1W	0.9215 (13)	0.6412 (13)	0.9750 (10)	0.119 (4)	0.50
H1W	1.0104	0.6270	0.9637	0.179*	0.50
H2W	0.8765	0.5737	0.9756	0.179*	0.50

	U11	U22	U33	U12	U13	U23
Cu1	0.0187 (2)	0.0152 (2)	0.0193 (3)	0.00275 (16)	0.00795 (17)	0.00502 (17)
Cl1	0.0245 (5)	0.0333 (5)	0.0202 (5)	0.0044 (4)	0.0052 (4)	0.0060 (4)
O1	0.0211 (13)	0.0159 (13)	0.0269 (15)	0.0031 (10)	0.0067 (11)	0.0074 (11)
O2	0.0161 (12)	0.0166 (12)	0.0217 (14)	0.0036 (9)	0.0059 (10)	0.0043 (10)
O3	0.059 (2)	0.058 (2)	0.049 (2)	0.0059 (18)	0.0366 (18)	0.0171 (18)
O4	0.0452 (17)	0.0316 (16)	0.0297 (17)	0.0101 (13)	0.0065 (14)	0.0069 (13)
O5	0.091 (3)	0.0350 (18)	0.0285 (18)	0.0096 (18)	−0.0034 (18)	−0.0029 (15)
O6	0.0277 (16)	0.072 (3)	0.062 (2)	0.0046 (16)	−0.0021 (16)	0.035 (2)
O7	0.070 (4)	0.139 (6)	0.236 (9)	0.031 (4)	0.044 (5)	0.107 (6)
N1	0.0209 (15)	0.0146 (15)	0.0249 (17)	−0.0006 (12)	0.0043 (13)	0.0058 (13)
N2	0.0170 (14)	0.0155 (14)	0.0210 (16)	0.0020 (11)	0.0037 (12)	0.0039 (12)
N3	0.0193 (15)	0.0214 (16)	0.0181 (16)	0.0022 (12)	0.0057 (12)	0.0058 (13)
N4	0.0165 (14)	0.0169 (15)	0.0214 (17)	0.0007 (11)	0.0050 (12)	0.0070 (13)
N5	0.038 (3)	0.060 (3)	0.117 (5)	0.011 (2)	0.032 (3)	−0.015 (3)
C1	0.038 (2)	0.023 (2)	0.030 (2)	−0.0007 (17)	0.0105 (18)	0.0074 (17)
C2	0.039 (2)	0.021 (2)	0.036 (3)	−0.0037 (17)	0.0019 (19)	0.0133 (18)
C3	0.031 (2)	0.0142 (18)	0.037 (2)	0.0020 (16)	−0.0067 (18)	0.0056 (17)
C4	0.0266 (19)	0.0194 (19)	0.029 (2)	0.0046 (15)	0.0007 (17)	−0.0002 (16)
C5	0.0144 (16)	0.0192 (18)	0.0200 (19)	−0.0001 (13)	−0.0033 (14)	0.0030 (15)
C6	0.0130 (16)	0.0188 (18)	0.0208 (19)	0.0018 (13)	0.0003 (14)	0.0006 (15)
C7	0.032 (2)	0.025 (2)	0.024 (2)	0.0060 (16)	0.0081 (17)	−0.0021 (16)
C8	0.032 (2)	0.036 (2)	0.021 (2)	0.0026 (18)	0.0107 (17)	0.0004 (18)
C9	0.029 (2)	0.028 (2)	0.025 (2)	−0.0008 (16)	0.0087 (17)	0.0088 (17)
C10	0.0278 (19)	0.0192 (18)	0.025 (2)	0.0029 (15)	0.0094 (16)	0.0057 (16)
C11	0.0257 (19)	0.030 (2)	0.023 (2)	0.0024 (16)	0.0068 (16)	0.0051 (17)
C12	0.027 (2)	0.032 (2)	0.024 (2)	−0.0016 (16)	−0.0008 (16)	0.0056 (17)
C13	0.0189 (18)	0.030 (2)	0.033 (2)	0.0015 (16)	0.0027 (16)	0.0049 (18)
C14	0.0208 (17)	0.0181 (18)	0.026 (2)	0.0016 (14)	0.0077 (15)	0.0051 (15)
C15	0.0198 (17)	0.0132 (16)	0.0215 (19)	0.0017 (13)	0.0072 (15)	0.0032 (14)
C16	0.0188 (17)	0.0148 (17)	0.0213 (19)	−0.0001 (13)	0.0068 (14)	0.0055 (14)
C17	0.0205 (18)	0.0253 (19)	0.026 (2)	0.0008 (15)	0.0103 (16)	0.0030 (16)
C18	0.028 (2)	0.034 (2)	0.023 (2)	0.0019 (17)	0.0125 (17)	0.0038 (17)
C19	0.026 (2)	0.035 (2)	0.022 (2)	−0.0014 (17)	0.0053 (16)	0.0073 (17)
C20	0.0188 (17)	0.0252 (19)	0.023 (2)	0.0006 (15)	0.0053 (15)	0.0062 (16)
C21	0.0198 (17)	0.0185 (18)	0.0159 (18)	0.0044 (14)	0.0093 (14)	0.0070 (14)
C22A	0.011 (3)	0.039 (4)	0.098 (6)	0.002 (3)	0.005 (3)	0.021 (4)
C23A	0.083 (6)	0.126 (7)	0.107 (7)	0.019 (5)	0.019 (5)	−0.007 (6)
C22B	0.011 (3)	0.039 (4)	0.098 (6)	0.002 (3)	0.005 (3)	0.021 (4)
C23B	0.083 (6)	0.126 (7)	0.107 (7)	0.019 (5)	0.019 (5)	−0.007 (6)
C24	0.050 (4)	0.178 (10)	0.066 (5)	−0.029 (5)	−0.004 (4)	0.017 (5)
O1S	0.095 (8)	0.155 (12)	0.110 (10)	−0.004 (8)	0.015 (7)	0.032 (9)

Cu1—O2	1.995 (2)	C8—H8	0.9500
Cu1—N2	2.015 (3)	C9—C10	1.378 (5)
Cu1—N1	2.015 (3)	C9—H9	0.9500
Cu1—N4	2.036 (3)	C10—H10	0.9500
Cu1—N3	2.232 (3)	C11—C12	1.381 (5)
Cu1—O1	2.346 (3)	C11—H11	0.9500
Cl1—O5	1.417 (3)	C12—C13	1.383 (6)
Cl1—O6	1.428 (3)	C12—H12	0.9500
Cl1—O3	1.428 (3)	C13—C14	1.382 (6)
Cl1—O4	1.442 (3)	C13—H13	0.9500
O1—C21	1.236 (4)	C14—C15	1.395 (5)
O2—C21i	1.265 (4)	C14—H14	0.9500
O7—C24	1.065 (9)	C15—C16	1.486 (5)
N1—C1	1.339 (5)	C16—C17	1.395 (5)
N1—C5	1.348 (5)	C17—C18	1.375 (6)
N2—C10	1.340 (5)	C17—H17	0.9500
N2—C6	1.348 (4)	C18—C19	1.384 (5)
N3—C11	1.339 (5)	C18—H18	0.9500
N3—C15	1.346 (5)	C19—C20	1.385 (5)
N4—C20	1.340 (5)	C19—H19	0.9500
N4—C16	1.354 (4)	C20—H20	0.9500
N5—C22A	1.313 (11)	C21—O2i	1.265 (4)
N5—C24	1.305 (9)	C21—C21i	1.573 (7)
N5—C23B	1.463 (14)	C22A—H22A	0.9800
N5—C23A	1.527 (14)	C22A—H22B	0.9800
N5—C22B	1.631 (11)	C22A—H22C	0.9800
C1—C2	1.387 (6)	C23A—H23A	0.9800
C1—H1	0.9500	C23A—H23B	0.9800
C2—C3	1.375 (6)	C23A—H23C	0.9800
C2—H2	0.9500	C22B—H22D	0.9800
C3—C4	1.379 (6)	C22B—H22E	0.9800
C3—H3	0.9500	C22B—H22F	0.9800
C4—C5	1.390 (5)	C23B—H23D	0.9800
C4—H4	0.9500	C23B—H23E	0.9800
C5—C6	1.485 (5)	C23B—H23F	0.9800
C6—C7	1.380 (5)	C24—H24	0.9500
C7—C8	1.379 (6)	O1W—H1W	0.9100
C7—H7	0.9500	O1W—H2W	0.8500
C8—C9	1.377 (6)
O2—Cu1—N2	92.86 (11)	C8—C9—C10	118.6 (4)
O2—Cu1—N1	165.61 (11)	C8—C9—H9	120.7
N2—Cu1—N1	80.78 (12)	C10—C9—H9	120.7
O2—Cu1—N4	89.79 (11)	N2—C10—C9	122.3 (4)
N2—Cu1—N4	174.69 (12)	N2—C10—H10	118.8
N1—Cu1—N4	97.65 (12)	C9—C10—H10	118.8
O2—Cu1—N3	93.94 (10)	N3—C11—C12	123.2 (4)
N2—Cu1—N3	97.73 (11)	N3—C11—H11	118.4
N1—Cu1—N3	99.68 (12)	C12—C11—H11	118.4
N4—Cu1—N3	77.48 (11)	C11—C12—C13	118.1 (4)
O2—Cu1—O1	77.12 (9)	C11—C12—H12	121.0
N2—Cu1—O1	89.30 (11)	C13—C12—H12	121.0
N1—Cu1—O1	89.83 (10)	C14—C13—C12	119.7 (4)
N4—Cu1—O1	95.78 (10)	C14—C13—H13	120.2
N3—Cu1—O1	168.94 (10)	C12—C13—H13	120.2
O5—Cl1—O6	110.2 (2)	C13—C14—C15	118.8 (4)
O5—Cl1—O3	110.4 (2)	C13—C14—H14	120.6
O6—Cl1—O3	107.9 (2)	C15—C14—H14	120.6
O5—Cl1—O4	109.5 (2)	N3—C15—C14	121.6 (3)
O6—Cl1—O4	108.4 (2)	N3—C15—C16	115.9 (3)
O3—Cl1—O4	110.2 (2)	C14—C15—C16	122.5 (3)
C21—O1—Cu1	108.6 (2)	N4—C16—C17	121.1 (3)
C21i—O2—Cu1	119.4 (2)	N4—C16—C15	116.2 (3)
C1—N1—C5	118.8 (3)	C17—C16—C15	122.7 (3)
C1—N1—Cu1	126.4 (3)	C18—C17—C16	119.2 (3)
C5—N1—Cu1	114.7 (2)	C18—C17—H17	120.4
C10—N2—C6	119.1 (3)	C16—C17—H17	120.4
C10—N2—Cu1	125.8 (3)	C17—C18—C19	119.8 (4)
C6—N2—Cu1	115.0 (2)	C17—C18—H18	120.1
C11—N3—C15	118.6 (3)	C19—C18—H18	120.1
C11—N3—Cu1	129.3 (3)	C20—C19—C18	118.3 (4)
C15—N3—Cu1	112.0 (2)	C20—C19—H19	120.9
C20—N4—C16	119.0 (3)	C18—C19—H19	120.9
C20—N4—Cu1	122.7 (2)	N4—C20—C19	122.7 (3)
C16—N4—Cu1	117.9 (2)	N4—C20—H20	118.7
C22A—N5—C24	134.7 (8)	C19—C20—H20	118.7
C22A—N5—C23B	78.1 (9)	O1—C21—O2i	125.4 (3)
C24—N5—C23B	146.3 (9)	O1—C21—C21i	117.5 (4)
C22A—N5—C23A	125.4 (9)	O2i—C21—C21i	117.1 (4)
C24—N5—C23A	96.1 (9)	N5—C22A—H22A	109.4
C23B—N5—C23A	49.9 (9)	N5—C22A—H22B	109.5
C24—N5—C22B	108.0 (6)	H22A—C22A—H22B	109.5
C23B—N5—C22B	105.5 (9)	N5—C22A—H22C	109.5
C23A—N5—C22B	154.7 (8)	H22A—C22A—H22C	109.5
N1—C1—C2	122.2 (4)	H22B—C22A—H22C	109.5
N1—C1—H1	118.9	N5—C23A—H23A	109.5
C2—C1—H1	118.9	N5—C23A—H23B	109.4
C3—C2—C1	118.8 (4)	H23A—C23A—H23B	109.5
C3—C2—H2	120.6	N5—C23A—H23C	109.5
C1—C2—H2	120.6	H23A—C23A—H23C	109.5
C2—C3—C4	119.6 (4)	H23B—C23A—H23C	109.5
C2—C3—H3	120.2	N5—C22B—H22D	109.5
C4—C3—H3	120.2	N5—C22B—H22E	109.5
C3—C4—C5	118.7 (4)	H22D—C22B—H22E	109.5
C3—C4—H4	120.6	N5—C22B—H22F	109.5
C5—C4—H4	120.6	H22D—C22B—H22F	109.5
N1—C5—C4	121.8 (3)	H22E—C22B—H22F	109.5
N1—C5—C6	115.0 (3)	N5—C23B—H23D	109.5
C4—C5—C6	123.2 (4)	N5—C23B—H23E	109.5
N2—C6—C7	121.2 (3)	H23D—C23B—H23E	109.5
N2—C6—C5	114.4 (3)	N5—C23B—H23F	109.4
C7—C6—C5	124.4 (3)	H23D—C23B—H23F	109.5
C8—C7—C6	119.3 (4)	H23E—C23B—H23F	109.5
C8—C7—H7	120.3	O7—C24—N5	128.6 (9)
C6—C7—H7	120.3	O7—C24—H24	115.7
C9—C8—C7	119.4 (4)	N5—C24—H24	115.7
C9—C8—H8	120.3	H1W—O1W—H2W	110.2
C7—C8—H8	120.3

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O5ii	0.91	2.45	3.311 (13)	159.
O1W—H2W···O5	0.85	2.04	2.882 (14)	169.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O5i	0.91	2.45	3.311 (13)	159
O1W—H2W⋯O5	0.85	2.04	2.882 (14)	169

Symmetry code: (i) .