(1,2-Bis{[3-(2-pyridyl)­pyrazol-1-yl]­methyl}benzene)­perchloratosodium

Bell, Z.R.; Ward, M.D.

doi:10.1107/S160053680301554X

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(1,2-Bis{[3-(2-pyridyl)pyrazol-1-yl]methyl}benzene)perchloratosodium

Z. R. Bell and M. D. Ward

In the title compound, [Na(ClO₄)(C₂₄H₂₀N₆)], the sodium cation is in a square-pyramidal geometry, which is distorted from the ideal (τ = 0.19), with the four N-donor atoms of the bis-bidentate chelating units from the ligand arranged equatorially, and with the perchlorate anion at the apical site.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301554X/cf6273sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301554X/cf6273Isup2.hkl Contains datablock I

CCDC reference: 222820

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.112
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.99

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.824     0.970
            Tmin' and Tmax expected:      0.954     0.973
            RR' =      0.866
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        O11
PLAT410_ALERT_2_C Short Intra H...H Contact  H26B   ..  H46A     =       1.91 Ang.

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

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

Comment top

The coordination chemistry of the ligand L1 has been well documented for the first row transition metals; it forms tetrahedral cages and open-chain dinuclear structures (Fleming et al., 1998; Paul et al., 2002). Several complexes of alkali metals with N-donor ligands are observed in the literature, although they usually employ highly preorganized ligands, where the cavity size is comparable to that of the alkali metal ion and the coordination geometry is particularly unsuited to a transition metal. Examples include ligands such as torands (Bell et al., 1992; Bell et al., 1993), macrocycles (Constable et al., 1988) and cryptands (Lehn & DeVains, 1992). However, a helical structure containing K⁺ ions has been reported, based on a hexadentate N-donor ligand which consists of two terdentate binding domains (Psillakis et al., 1997).

The molecular structure of the title compound is shown in Fig. 1. It is a relatively unusual example of an alkali metal complex with an open-chain N-donor chelating ligand. The sodium cation is surrounded by four nitrogen donors from L1 and a single perchlorate anion, thus yielding a neutral complex. The Na—N average bond length is 2.487 Å, which is comparable to the Na—N average bond length found in six-coordinate chelate complexes with the bidentate phen unit (Qian et al., 1994). Although there are many sodium complexes reported with cryptands (Echegoyen et al., 1991; McKee et al., 1992), the comparison of bond lengths can be complex, since it is thought that they are, in part, dependent on the rigidity of the ligand and the coordination number of the Na⁺ ion (Caron et al., 1985). The N atoms of the ligand unit are not bound to the sodium ion in a plane. One of the pyrazole–pyridine units is approximately planar, but the other has an angle of 17.1 (2)° between the rings. The approximate angle between the bidentate arms is 131.9 (14)°, thus enabling the perchlorate anion to coordinate comfortably to the Na⁺ ion in the apical position. The Na—O bond length is 2.3359 (18) Å.

For a five-coordinate geometry, there is a structural continuum between the ideal square-pyramidal (SP) and trigonal-bipyramidal (TBP) extremes. The structural index parameter τ (degree of trigonality) can be defined as τ = (β-α)/60, where β and α are the largest and smallest angles, respectively, at the central atom. τ is equal to zero for a perfect SP geometry, and equal to unity for a perfect TBP geometry (Addison et al., 1984). For the title compound, τ = 0.19, indicating that the coordination geometry of sodium is closer to, but distorted from, ideal square pyramidal.

Experimental top

Crystals of the title compound were obtained via a serendipitous route upon reaction of (CH₃CO₂)₃Mn·2H₂O and L1 in a 2:3 ratio in methanol. An aqueous solution of NaClO₄ was added, to afford a white precipitate, which was collected by filtration. The title compound was isolated upon recrystallization of the precipitate from MeCN/Et₂O.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT and SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

[Na1,2-bis[{3-(2-pyridyl)-pyrazol-1-yl}methyl]benzene][ClO₄] top

Crystal data top

[Na(ClO₄)(C₂₄H₂₀N₆)]	Z = 2
M_r = 514.90	F(000) = 532
Triclinic, P1	D_x = 1.471 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.353 (4) Å	Cell parameters from 54 reflections
b = 10.558 (3) Å	θ = 0.8–1.0°
c = 12.794 (4) Å	µ = 0.23 mm⁻¹
α = 100.26 (3)°	T = 173 K
β = 107.64 (3)°	Block, colourless
γ = 97.33 (3)°	0.20 × 0.15 × 0.12 mm
V = 1162.3 (8) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5304 independent reflections
Radiation source: fine-focus sealed tube	3677 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 8.2 pixels mm^-1	θ_max = 27.5°, θ_min = 1.7°
narrow–frame ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.824, T_max = 0.970	l = −16→16
12525 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0581P)²] where P = (F_o² + 2F_c²)/3
5304 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Na(ClO₄)(C₂₄H₂₀N₆)]	γ = 97.33 (3)°
M_r = 514.90	V = 1162.3 (8) Å³
Triclinic, P1	Z = 2
a = 9.353 (4) Å	Mo Kα radiation
b = 10.558 (3) Å	µ = 0.23 mm⁻¹
c = 12.794 (4) Å	T = 173 K
α = 100.26 (3)°	0.20 × 0.15 × 0.12 mm
β = 107.64 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5304 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3677 reflections with I > 2σ(I)
T_min = 0.824, T_max = 0.970	R_int = 0.036
12525 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
5304 reflections	Δρ_min = −0.35 e Å⁻³
325 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
Na1	0.32557 (8)	0.56586 (7)	0.25921 (6)	0.02888 (19)
N11	0.56446 (18)	0.57971 (15)	0.41378 (13)	0.0297 (4)
N21	0.44361 (17)	0.37220 (14)	0.22393 (12)	0.0250 (3)
N25	0.42073 (18)	0.26114 (14)	0.14498 (12)	0.0263 (4)
N41	0.04076 (17)	0.50705 (14)	0.17403 (12)	0.0246 (3)
N45	−0.06916 (18)	0.42002 (15)	0.08818 (12)	0.0265 (4)
N51	0.19760 (18)	0.73085 (15)	0.34344 (13)	0.0289 (4)
C12	0.6455 (2)	0.48469 (18)	0.40149 (15)	0.0251 (4)
C13	0.7866 (2)	0.48643 (19)	0.48090 (16)	0.0304 (4)
H13A	0.8405	0.4199	0.4700	0.036*
C14	0.8453 (2)	0.5879 (2)	0.57576 (16)	0.0340 (5)
H14A	0.9393	0.5909	0.6294	0.041*
C15	0.7628 (2)	0.6844 (2)	0.58981 (17)	0.0366 (5)
H15A	0.7992	0.7536	0.6532	0.044*
C16	0.6244 (2)	0.6760 (2)	0.50730 (17)	0.0371 (5)
H16A	0.5690	0.7416	0.5173	0.045*
C22	0.5797 (2)	0.37638 (17)	0.30077 (15)	0.0242 (4)
C23	0.6413 (2)	0.26702 (19)	0.27037 (16)	0.0302 (4)
H23A	0.7340	0.2474	0.3096	0.036*
C24	0.5367 (2)	0.19541 (19)	0.17109 (16)	0.0296 (4)
H24A	0.5438	0.1163	0.1293	0.036*
C26	0.2745 (2)	0.21545 (19)	0.05395 (15)	0.0285 (4)
H26A	0.2851	0.1479	−0.0040	0.034*
H26B	0.2451	0.2878	0.0205	0.034*
C31	0.1507 (2)	0.16067 (17)	0.09671 (14)	0.0242 (4)
C32	0.1761 (2)	0.05817 (18)	0.15151 (16)	0.0311 (4)
H32A	0.2655	0.0255	0.1584	0.037*
C33	0.0714 (2)	0.00425 (18)	0.19565 (16)	0.0339 (5)
H33A	0.0905	−0.0637	0.2320	0.041*
C34	−0.0622 (2)	0.05199 (19)	0.18539 (16)	0.0341 (5)
H34A	−0.1326	0.0172	0.2158	0.041*
C35	−0.0902 (2)	0.15163 (19)	0.12970 (15)	0.0306 (4)
H35A	−0.1808	0.1825	0.1219	0.037*
C36	0.0149 (2)	0.20715 (17)	0.08469 (14)	0.0238 (4)
C42	−0.0358 (2)	0.58522 (17)	0.22193 (15)	0.0248 (4)
C43	−0.1939 (2)	0.54747 (18)	0.16638 (16)	0.0301 (4)
H43A	−0.2707	0.5859	0.1833	0.036*
C44	−0.2105 (2)	0.44140 (19)	0.08155 (17)	0.0318 (4)
H44A	−0.3023	0.3930	0.0291	0.038*
C46	−0.0292 (2)	0.31220 (18)	0.02081 (15)	0.0286 (4)
H46A	0.0556	0.3465	−0.0015	0.034*
H46B	−0.1156	0.2732	−0.0472	0.034*
C52	0.0464 (2)	0.69352 (17)	0.32094 (15)	0.0260 (4)
C53	−0.0303 (2)	0.75124 (19)	0.38820 (16)	0.0315 (4)
H53A	−0.1348	0.7230	0.3707	0.038*
C54	0.0503 (3)	0.85098 (19)	0.48129 (17)	0.0374 (5)
H54A	0.0013	0.8894	0.5284	0.045*
C55	0.2044 (3)	0.89283 (19)	0.50341 (17)	0.0372 (5)
H55A	0.2613	0.9610	0.5647	0.045*
C56	0.2718 (2)	0.83059 (19)	0.43202 (17)	0.0351 (5)
H56A	0.3755	0.8599	0.4465	0.042*
Cl1	0.51614 (5)	0.82266 (4)	0.19139 (4)	0.02962 (13)
O11	0.45964 (19)	0.68368 (14)	0.16868 (13)	0.0531 (4)
O12	0.4673 (2)	0.89235 (19)	0.27574 (14)	0.0677 (5)
O13	0.67729 (19)	0.84483 (18)	0.22873 (18)	0.0717 (6)
O14	0.4618 (2)	0.86635 (15)	0.08985 (13)	0.0619 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0243 (4)	0.0285 (4)	0.0317 (4)	0.0060 (3)	0.0074 (3)	0.0045 (3)
N11	0.0280 (9)	0.0287 (9)	0.0296 (9)	0.0062 (7)	0.0075 (7)	0.0023 (7)
N21	0.0237 (9)	0.0245 (8)	0.0252 (8)	0.0035 (6)	0.0075 (7)	0.0037 (6)
N25	0.0238 (9)	0.0250 (8)	0.0278 (8)	0.0035 (7)	0.0085 (7)	0.0013 (7)
N41	0.0254 (9)	0.0231 (8)	0.0237 (8)	0.0039 (7)	0.0053 (7)	0.0067 (6)
N45	0.0258 (9)	0.0250 (8)	0.0261 (8)	0.0060 (7)	0.0046 (7)	0.0057 (7)
N51	0.0299 (10)	0.0242 (8)	0.0306 (9)	0.0051 (7)	0.0078 (7)	0.0054 (7)
C12	0.0249 (10)	0.0272 (10)	0.0257 (9)	0.0028 (8)	0.0104 (8)	0.0103 (8)
C13	0.0275 (11)	0.0328 (11)	0.0312 (10)	0.0065 (9)	0.0072 (9)	0.0123 (9)
C14	0.0294 (12)	0.0403 (12)	0.0278 (10)	0.0000 (9)	0.0035 (9)	0.0124 (9)
C15	0.0382 (13)	0.0370 (12)	0.0273 (10)	−0.0018 (10)	0.0087 (9)	−0.0007 (9)
C16	0.0362 (13)	0.0359 (12)	0.0353 (11)	0.0090 (9)	0.0094 (10)	0.0011 (9)
C22	0.0227 (10)	0.0250 (10)	0.0257 (9)	0.0027 (8)	0.0088 (8)	0.0079 (8)
C23	0.0255 (11)	0.0312 (11)	0.0344 (10)	0.0089 (8)	0.0081 (9)	0.0092 (9)
C24	0.0293 (11)	0.0259 (10)	0.0363 (11)	0.0084 (8)	0.0152 (9)	0.0042 (8)
C26	0.0245 (11)	0.0320 (11)	0.0246 (9)	0.0037 (8)	0.0054 (8)	0.0014 (8)
C31	0.0238 (10)	0.0221 (9)	0.0216 (9)	0.0003 (8)	0.0052 (8)	−0.0009 (7)
C32	0.0338 (12)	0.0240 (10)	0.0322 (10)	0.0077 (8)	0.0073 (9)	0.0028 (8)
C33	0.0452 (13)	0.0218 (10)	0.0319 (11)	0.0031 (9)	0.0096 (10)	0.0068 (8)
C34	0.0377 (13)	0.0312 (11)	0.0292 (10)	−0.0069 (9)	0.0130 (9)	0.0032 (9)
C35	0.0267 (11)	0.0315 (11)	0.0299 (10)	0.0029 (8)	0.0081 (9)	0.0019 (8)
C36	0.0246 (10)	0.0216 (9)	0.0189 (8)	0.0003 (8)	0.0036 (8)	−0.0014 (7)
C42	0.0274 (11)	0.0232 (9)	0.0275 (9)	0.0078 (8)	0.0102 (8)	0.0113 (8)
C43	0.0249 (11)	0.0298 (10)	0.0363 (11)	0.0078 (8)	0.0097 (9)	0.0086 (9)
C44	0.0221 (11)	0.0314 (11)	0.0398 (11)	0.0053 (8)	0.0052 (9)	0.0113 (9)
C46	0.0289 (11)	0.0283 (10)	0.0263 (10)	0.0071 (8)	0.0063 (8)	0.0042 (8)
C52	0.0309 (11)	0.0225 (9)	0.0279 (9)	0.0087 (8)	0.0094 (8)	0.0123 (8)
C53	0.0333 (12)	0.0306 (11)	0.0355 (11)	0.0107 (9)	0.0144 (9)	0.0118 (9)
C54	0.0543 (15)	0.0305 (11)	0.0334 (11)	0.0161 (10)	0.0197 (10)	0.0078 (9)
C55	0.0485 (15)	0.0265 (11)	0.0306 (11)	0.0084 (10)	0.0065 (10)	0.0024 (9)
C56	0.0337 (12)	0.0294 (11)	0.0373 (11)	0.0066 (9)	0.0051 (9)	0.0074 (9)
Cl1	0.0275 (3)	0.0292 (3)	0.0320 (3)	0.00300 (19)	0.0099 (2)	0.0085 (2)
O11	0.0639 (12)	0.0339 (8)	0.0501 (10)	−0.0124 (8)	0.0111 (9)	0.0110 (7)
O12	0.0839 (15)	0.0761 (13)	0.0536 (11)	0.0215 (11)	0.0410 (10)	0.0057 (10)
O13	0.0272 (10)	0.0655 (12)	0.1143 (16)	−0.0008 (8)	0.0170 (10)	0.0190 (11)
O14	0.1025 (15)	0.0451 (10)	0.0384 (9)	0.0258 (10)	0.0146 (9)	0.0178 (8)

Geometric parameters (Å, º) top

Na1—O11	2.3359 (18)	C26—H26B	0.9700
Na1—N11	2.462 (2)	C31—C36	1.395 (3)
Na1—N21	2.4805 (18)	C31—C32	1.398 (3)
Na1—N41	2.499 (2)	C32—C33	1.382 (3)
Na1—N51	2.5046 (19)	C32—H32A	0.9300
N11—C16	1.339 (3)	C33—C34	1.385 (3)
N11—C12	1.348 (2)	C33—H33A	0.9300
N21—C22	1.341 (2)	C34—C35	1.381 (3)
N21—N25	1.351 (2)	C34—H34A	0.9300
N25—C24	1.351 (2)	C35—C36	1.399 (3)
N25—C26	1.458 (2)	C35—H35A	0.9300
N41—C42	1.344 (2)	C36—C46	1.518 (2)
N41—N45	1.350 (2)	C42—C43	1.401 (3)
N45—C44	1.349 (2)	C42—C52	1.474 (3)
N45—C46	1.461 (2)	C43—C44	1.370 (3)
N51—C56	1.337 (3)	C43—H43A	0.9300
N51—C52	1.345 (2)	C44—H44A	0.9300
C12—C13	1.396 (3)	C46—H46A	0.9700
C12—C22	1.470 (3)	C46—H46B	0.9700
C13—C14	1.380 (3)	C52—C53	1.387 (3)
C13—H13A	0.9300	C53—C54	1.379 (3)
C14—C15	1.373 (3)	C53—H53A	0.9300
C14—H14A	0.9300	C54—C55	1.378 (3)
C15—C16	1.381 (3)	C54—H54A	0.9300
C15—H15A	0.9300	C55—C56	1.380 (3)
C16—H16A	0.9300	C55—H55A	0.9300
C22—C23	1.401 (3)	C56—H56A	0.9300
C23—C24	1.363 (3)	Cl1—O13	1.4101 (19)
C23—H23A	0.9300	Cl1—O12	1.4200 (17)
C24—H24A	0.9300	Cl1—O14	1.4255 (16)
C26—C31	1.517 (3)	Cl1—O11	1.4402 (16)
C26—H26A	0.9700

O11—Na1—N11	90.60 (7)	H26A—C26—H26B	108.0
O11—Na1—N21	92.44 (6)	C36—C31—C32	118.85 (17)
N11—Na1—N21	68.75 (6)	C36—C31—C26	123.73 (17)
O11—Na1—N41	117.95 (6)	C32—C31—C26	117.42 (17)
N11—Na1—N41	151.16 (6)	C33—C32—C31	121.49 (19)
N21—Na1—N41	111.12 (7)	C33—C32—H32A	119.3
O11—Na1—N51	103.64 (6)	C31—C32—H32A	119.3
N11—Na1—N51	103.28 (7)	C32—C33—C34	119.61 (18)
N21—Na1—N51	162.31 (6)	C32—C33—H33A	120.2
N41—Na1—N51	67.84 (6)	C34—C33—H33A	120.2
C16—N11—C12	116.87 (17)	C35—C34—C33	119.59 (18)
C16—N11—Na1	125.86 (14)	C35—C34—H34A	120.2
C12—N11—Na1	117.22 (12)	C33—C34—H34A	120.2
C22—N21—N25	104.68 (15)	C34—C35—C36	121.36 (19)
C22—N21—Na1	114.94 (12)	C34—C35—H35A	119.3
N25—N21—Na1	140.18 (12)	C36—C35—H35A	119.3
N21—N25—C24	112.08 (15)	C31—C36—C35	119.09 (17)
N21—N25—C26	120.28 (15)	C31—C36—C46	123.46 (16)
C24—N25—C26	127.03 (16)	C35—C36—C46	117.41 (17)
C42—N41—N45	104.58 (15)	N41—C42—C43	111.24 (17)
C42—N41—Na1	115.33 (12)	N41—C42—C52	120.80 (17)
N45—N41—Na1	140.04 (12)	C43—C42—C52	127.96 (17)
C44—N45—N41	112.03 (16)	C44—C43—C42	104.78 (17)
C44—N45—C46	127.48 (16)	C44—C43—H43A	127.6
N41—N45—C46	120.30 (15)	C42—C43—H43A	127.6
C56—N51—C52	117.07 (17)	N45—C44—C43	107.37 (18)
C56—N51—Na1	123.79 (14)	N45—C44—H44A	126.3
C52—N51—Na1	115.92 (12)	C43—C44—H44A	126.3
N11—C12—C13	122.14 (18)	N45—C46—C36	112.14 (14)
N11—C12—C22	117.64 (17)	N45—C46—H46A	109.2
C13—C12—C22	120.22 (17)	C36—C46—H46A	109.2
C14—C13—C12	119.30 (19)	N45—C46—H46B	109.2
C14—C13—H13A	120.3	C36—C46—H46B	109.2
C12—C13—H13A	120.3	H46A—C46—H46B	107.9
C15—C14—C13	119.05 (19)	N51—C52—C53	122.33 (18)
C15—C14—H14A	120.5	N51—C52—C42	116.99 (17)
C13—C14—H14A	120.5	C53—C52—C42	120.67 (18)
C14—C15—C16	118.20 (19)	C54—C53—C52	119.3 (2)
C14—C15—H15A	120.9	C54—C53—H53A	120.4
C16—C15—H15A	120.9	C52—C53—H53A	120.4
N11—C16—C15	124.4 (2)	C55—C54—C53	118.97 (19)
N11—C16—H16A	117.8	C55—C54—H54A	120.5
C15—C16—H16A	117.8	C53—C54—H54A	120.5
N21—C22—C23	110.83 (17)	C54—C55—C56	118.1 (2)
N21—C22—C12	121.18 (16)	C54—C55—H55A	121.0
C23—C22—C12	127.99 (18)	C56—C55—H55A	121.0
C24—C23—C22	105.39 (18)	N51—C56—C55	124.2 (2)
C24—C23—H23A	127.3	N51—C56—H56A	117.9
C22—C23—H23A	127.3	C55—C56—H56A	117.9
N25—C24—C23	107.01 (17)	O13—Cl1—O12	109.34 (13)
N25—C24—H24A	126.5	O13—Cl1—O14	109.48 (12)
C23—C24—H24A	126.5	O12—Cl1—O14	109.87 (11)
N25—C26—C31	111.16 (15)	O13—Cl1—O11	108.21 (11)
N25—C26—H26A	109.4	O12—Cl1—O11	111.06 (11)
C31—C26—H26A	109.4	O14—Cl1—O11	108.85 (11)
N25—C26—H26B	109.4	Cl1—O11—Na1	129.64 (10)
C31—C26—H26B	109.4

Experimental details

Crystal data
Chemical formula	[Na(ClO₄)(C₂₄H₂₀N₆)]
M_r	514.90
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.353 (4), 10.558 (3), 12.794 (4)
α, β, γ (°)	100.26 (3), 107.64 (3), 97.33 (3)
V (Å³)	1162.3 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.20 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.824, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	12525, 5304, 3677
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 1.01
No. of reflections	5304
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.35

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT and SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top

Na1—O11	2.3359 (18)	Na1—N41	2.499 (2)
Na1—N11	2.462 (2)	Na1—N51	2.5046 (19)
Na1—N21	2.4805 (18)

O11—Na1—N11	90.60 (7)	N21—Na1—N41	111.12 (7)
O11—Na1—N21	92.44 (6)	O11—Na1—N51	103.64 (6)
N11—Na1—N21	68.75 (6)	N11—Na1—N51	103.28 (7)
O11—Na1—N41	117.95 (6)	N21—Na1—N51	162.31 (6)
N11—Na1—N41	151.16 (6)	N41—Na1—N51	67.84 (6)

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