[1,8-Bis(2-benzyl)-1,3,6,8,10,13-hexa­aza­cyclo­tetra­decane]­nickel(II) diperchlorate

In the title compound, [Ni(C₂₂H₃₄N₆)](ClO₄)₂, the 14-membered hexa­aza­cyclo­tetra­decane macrocycle chelates to the Ni atom through its four secondary N atoms. The asymmetric unit contains two independent half-mol­ecules, with the Ni atoms located on inversion centers. The Ni atoms have a distorted octahedral geometry, with long Ni-O(perchlorate) bonds. The occurrence of hydrogen-bonding interactions results in a linear chain structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.105
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

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

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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLUTON (Spek, 1990); software used to prepare material for publication: SHELXL97.

[1,8-Bis(2-benzyl)-1,3,6,8,10,13-hexaazacyclotetradecane]nickel(II) diperchlorate

Crystal data

[Ni(C22H34N6)](ClO4)2	Z = 2
Mr = 640.16	F(000) = 668
Triclinic, P1	Dx = 1.552 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.209 (1) Å	Cell parameters from 855 reflections
b = 11.617 (1) Å	θ = 4.0–29.8°
c = 11.916 (1) Å	µ = 0.96 mm^−1
α = 87.633 (2)°	T = 298 K
β = 75.940 (2)°	Prism, yellow
γ = 88.501 (2)°	0.23 × 0.22 × 0.12 mm
V = 1369.5 (2) Å^3

Data collection

Bruker SMART 1K area-detector diffractometer	6134 independent reflections
Radiation source: normal-focus sealed tube	5089 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 4.1°
φ and ω scans	h = −13→9
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	k = −15→12
Tmin = 0.809, Tmax = 0.893	l = −15→12
8366 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.4245P] where P = (Fo^2 + 2Fc^2)/3
6134 reflections	(Δ/σ)max = 0.001
357 parameters	Δρmax = 0.66 e Å^−3
96 restraints	Δρmin = −0.51 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.02862 (10)
Ni2	0.5000	0.0000	0.0000	0.02726 (10)
C1	0.5635 (3)	0.5956 (2)	0.7049 (2)	0.0451 (5)
H1A	0.5782	0.6711	0.6666	0.054*
H1B	0.5305	0.6068	0.7872	0.054*
C2	0.3270 (3)	0.6017 (2)	0.6905 (2)	0.0454 (5)
H2A	0.3417	0.6824	0.6679	0.054*
H2B	0.2864	0.5957	0.7730	0.054*
C3	0.2370 (2)	0.5499 (2)	0.6242 (2)	0.0456 (5)
H3A	0.2105	0.4733	0.6554	0.055*
H3B	0.1561	0.5971	0.6294	0.055*
C4	0.2433 (2)	0.4740 (2)	0.4340 (2)	0.0425 (5)
H4A	0.2322	0.3969	0.4691	0.051*
H4B	0.1539	0.5072	0.4397	0.051*
C5	0.3153 (2)	0.5733 (2)	0.2428 (2)	0.0432 (5)
H5A	0.3691	0.5593	0.1653	0.052*
H5B	0.3600	0.6317	0.2751	0.052*
C6	0.1781 (2)	0.6184 (2)	0.23504 (19)	0.0406 (5)
C7	0.1166 (3)	0.5790 (2)	0.1530 (2)	0.0539 (6)
H7	0.1585	0.5212	0.1046	0.065*
C8	−0.0066 (3)	0.6247 (3)	0.1421 (3)	0.0657 (8)
H8	−0.0457	0.5992	0.0850	0.079*
C9	−0.0713 (3)	0.7080 (3)	0.2158 (3)	0.0634 (8)
H9	−0.1548	0.7377	0.2094	0.076*
C10	−0.0127 (3)	0.7469 (3)	0.2980 (3)	0.0606 (7)
H10	−0.0564	0.8030	0.3480	0.073*
C11	0.1121 (3)	0.7029 (2)	0.3073 (2)	0.0511 (6)
H11	0.1519	0.7306	0.3629	0.061*
C12	0.2410 (2)	−0.1159 (2)	0.0301 (2)	0.0429 (5)
H12A	0.2788	−0.1878	0.0536	0.052*
H12B	0.1459	−0.1135	0.0691	0.052*
C13	0.2878 (2)	−0.0234 (2)	0.19751 (17)	0.0395 (5)
H13A	0.3083	−0.1004	0.2239	0.047*
H13B	0.1945	−0.0044	0.2343	0.047*
C14	0.3805 (2)	0.0622 (2)	0.22703 (18)	0.0398 (5)
H14A	0.3513	0.1402	0.2118	0.048*
H14B	0.3814	0.0536	0.3082	0.048*
C15	0.6124 (2)	0.13189 (19)	0.1601 (2)	0.0385 (5)
H15A	0.5768	0.2044	0.1358	0.046*
H15B	0.6155	0.1377	0.2404	0.046*
C16	0.8320 (2)	0.0343 (2)	0.1414 (2)	0.0421 (5)
H16A	0.9017	0.0025	0.0795	0.051*
H16B	0.7778	−0.0289	0.1820	0.051*
C17	0.8971 (2)	0.0935 (2)	0.2244 (2)	0.0390 (5)
C18	0.8651 (3)	0.0638 (2)	0.3413 (2)	0.0514 (6)
H18	0.8008	0.0080	0.3704	0.062*
C19	0.9289 (3)	0.1170 (3)	0.4158 (3)	0.0646 (8)
H19	0.9072	0.0964	0.4943	0.078*
C20	1.0231 (3)	0.1992 (3)	0.3740 (3)	0.0645 (8)
H20	1.0661	0.2338	0.4240	0.077*
C21	1.0545 (3)	0.2312 (3)	0.2588 (3)	0.0596 (7)
H21	1.1180	0.2880	0.2308	0.071*
C22	0.9916 (2)	0.1787 (2)	0.1839 (2)	0.0496 (6)
H22	1.0129	0.2009	0.1058	0.059*
N1	0.45669 (19)	0.53585 (15)	0.66207 (15)	0.0349 (4)
H1	0.4418	0.4674	0.7027	0.042*
N2	0.31535 (17)	0.54460 (15)	0.50175 (15)	0.0342 (4)
H2	0.3177	0.6178	0.4710	0.041*
N3	0.3102 (2)	0.46581 (16)	0.31442 (16)	0.0411 (4)
N4	0.30957 (17)	−0.01765 (15)	0.06928 (14)	0.0323 (4)
H4	0.2676	0.0481	0.0511	0.039*
N5	0.51754 (17)	0.03758 (15)	0.15204 (14)	0.0321 (4)
H5	0.5488	−0.0275	0.1828	0.039*
N6	0.74627 (19)	0.11509 (16)	0.09187 (16)	0.0391 (4)
Cl1	0.53145 (6)	0.81334 (4)	0.42677 (5)	0.04294 (14)
O11	0.5861 (2)	0.90013 (18)	0.34389 (19)	0.0719 (6)
O12	0.5997 (3)	0.70582 (17)	0.4011 (2)	0.0792 (7)
O13	0.3930 (2)	0.7962 (2)	0.4239 (3)	0.0947 (8)
O14	0.5366 (5)	0.8438 (2)	0.5369 (2)	0.1286 (13)
Cl2	0.36834 (6)	0.29594 (5)	−0.04832 (5)	0.04134 (14)
O21	0.3469 (2)	0.39121 (17)	−0.12005 (19)	0.0674 (6)
O22	0.4846 (3)	0.2315 (2)	−0.1008 (3)	0.1066 (10)
O23	0.2580 (2)	0.2180 (2)	−0.0296 (3)	0.1031 (10)
O24	0.3812 (6)	0.3315 (3)	0.0565 (3)	0.1586 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.03381 (19)	0.02616 (18)	0.02739 (18)	0.00008 (13)	−0.01048 (14)	−0.00026 (13)
Ni2	0.03079 (18)	0.02865 (18)	0.02325 (17)	−0.00063 (13)	−0.00834 (13)	−0.00073 (13)
C1	0.0639 (15)	0.0354 (11)	0.0433 (12)	0.0033 (10)	−0.0263 (11)	−0.0074 (9)
C2	0.0537 (14)	0.0440 (12)	0.0371 (12)	0.0139 (10)	−0.0091 (10)	−0.0055 (9)
C3	0.0391 (12)	0.0507 (14)	0.0435 (13)	0.0060 (10)	−0.0046 (10)	0.0022 (10)
C4	0.0441 (12)	0.0406 (12)	0.0474 (13)	−0.0105 (10)	−0.0208 (10)	0.0098 (10)
C5	0.0476 (13)	0.0437 (12)	0.0423 (12)	−0.0040 (10)	−0.0196 (10)	0.0080 (10)
C6	0.0441 (12)	0.0413 (12)	0.0386 (11)	−0.0057 (9)	−0.0153 (10)	0.0107 (9)
C7	0.0617 (16)	0.0541 (15)	0.0526 (15)	0.0000 (12)	−0.0269 (13)	−0.0011 (12)
C8	0.0622 (17)	0.076 (2)	0.0698 (19)	−0.0096 (15)	−0.0391 (16)	0.0094 (16)
C9	0.0471 (15)	0.0679 (18)	0.076 (2)	0.0012 (13)	−0.0220 (14)	0.0231 (16)
C10	0.0614 (17)	0.0567 (16)	0.0603 (17)	0.0099 (13)	−0.0107 (14)	0.0065 (13)
C11	0.0594 (15)	0.0479 (14)	0.0496 (14)	−0.0007 (11)	−0.0210 (12)	0.0018 (11)
C12	0.0432 (12)	0.0473 (13)	0.0403 (12)	−0.0128 (10)	−0.0138 (10)	0.0060 (10)
C13	0.0388 (11)	0.0515 (13)	0.0257 (10)	−0.0024 (9)	−0.0032 (8)	0.0013 (9)
C14	0.0389 (11)	0.0509 (13)	0.0289 (10)	0.0037 (10)	−0.0061 (9)	−0.0085 (9)
C15	0.0421 (11)	0.0368 (11)	0.0415 (12)	0.0007 (9)	−0.0188 (10)	−0.0085 (9)
C16	0.0392 (11)	0.0469 (13)	0.0436 (12)	0.0027 (9)	−0.0157 (10)	−0.0064 (10)
C17	0.0330 (10)	0.0456 (12)	0.0412 (12)	0.0038 (9)	−0.0142 (9)	−0.0032 (9)
C18	0.0556 (15)	0.0543 (15)	0.0448 (13)	−0.0048 (12)	−0.0130 (11)	0.0011 (11)
C19	0.082 (2)	0.0737 (19)	0.0430 (14)	0.0038 (16)	−0.0240 (14)	−0.0062 (13)
C20	0.0671 (18)	0.0682 (19)	0.072 (2)	0.0038 (15)	−0.0405 (16)	−0.0226 (15)
C21	0.0443 (14)	0.0572 (16)	0.081 (2)	−0.0081 (12)	−0.0218 (14)	−0.0059 (14)
C22	0.0427 (13)	0.0574 (15)	0.0497 (14)	−0.0058 (11)	−0.0142 (11)	0.0050 (11)
N1	0.0457 (10)	0.0306 (9)	0.0297 (8)	0.0041 (7)	−0.0122 (8)	−0.0001 (7)
N2	0.0369 (9)	0.0321 (9)	0.0346 (9)	−0.0006 (7)	−0.0113 (7)	0.0039 (7)
N3	0.0516 (11)	0.0374 (10)	0.0404 (10)	−0.0036 (8)	−0.0233 (9)	0.0031 (8)
N4	0.0330 (9)	0.0360 (9)	0.0288 (8)	−0.0009 (7)	−0.0096 (7)	0.0023 (7)
N5	0.0362 (9)	0.0332 (9)	0.0289 (8)	0.0018 (7)	−0.0119 (7)	−0.0017 (7)
N6	0.0390 (9)	0.0441 (10)	0.0386 (10)	−0.0033 (8)	−0.0177 (8)	−0.0028 (8)
Cl1	0.0632 (4)	0.0310 (3)	0.0349 (3)	−0.0052 (2)	−0.0128 (2)	0.0043 (2)
O11	0.0920 (15)	0.0579 (12)	0.0685 (13)	−0.0242 (11)	−0.0276 (12)	0.0324 (10)
O12	0.0881 (16)	0.0418 (11)	0.1023 (18)	0.0110 (10)	−0.0145 (14)	−0.0004 (11)
O13	0.0630 (14)	0.0772 (16)	0.142 (3)	−0.0115 (12)	−0.0235 (15)	0.0178 (16)
O14	0.260 (4)	0.088 (2)	0.0543 (15)	−0.015 (2)	−0.068 (2)	−0.0070 (13)
Cl2	0.0473 (3)	0.0423 (3)	0.0358 (3)	0.0040 (2)	−0.0140 (2)	0.0042 (2)
O21	0.0668 (12)	0.0590 (12)	0.0768 (14)	0.0002 (10)	−0.0235 (11)	0.0301 (10)
O22	0.0846 (17)	0.0700 (16)	0.136 (2)	0.0284 (14)	0.0227 (16)	0.0227 (15)
O23	0.0710 (15)	0.0916 (18)	0.148 (3)	−0.0240 (13)	−0.0394 (16)	0.0666 (17)
O24	0.313 (6)	0.112 (2)	0.086 (2)	0.020 (3)	−0.116 (3)	−0.0286 (18)

Geometric parameters (Å, º)

Ni1—N1	1.9340 (17)	C13—N4	1.489 (3)
Ni1—N2	1.9372 (17)	C13—C14	1.500 (3)
Ni1—O12	2.730 (2)	C13—H13A	0.9700
Ni2—N4	1.9314 (17)	C13—H13B	0.9700
Ni2—N5	1.9318 (16)	C14—N5	1.494 (3)
Ni2—O22	2.916 (2)	C14—H14A	0.9700
C1—N3^i	1.431 (3)	C14—H14B	0.9700
C1—N1	1.506 (3)	C15—N6	1.424 (3)
C1—H1A	0.9700	C15—N5	1.502 (3)
C1—H1B	0.9700	C15—H15A	0.9700
C2—N1	1.484 (3)	C15—H15B	0.9700
C2—C3	1.501 (4)	C16—N6	1.469 (3)
C2—H2A	0.9700	C16—C17	1.514 (3)
C2—H2B	0.9700	C16—H16A	0.9700
C3—N2	1.487 (3)	C16—H16B	0.9700
C3—H3A	0.9700	C17—C18	1.383 (3)
C3—H3B	0.9700	C17—C22	1.388 (3)
C4—N3	1.429 (3)	C18—C19	1.393 (4)
C4—N2	1.497 (3)	C18—H18	0.9300
C4—H4A	0.9700	C19—C20	1.364 (5)
C4—H4B	0.9700	C19—H19	0.9300
C5—N3	1.478 (3)	C20—C21	1.370 (4)
C5—C6	1.506 (3)	C20—H20	0.9300
C5—H5A	0.9700	C21—C22	1.387 (4)
C5—H5B	0.9700	C21—H21	0.9300
C6—C7	1.381 (3)	C22—H22	0.9300
C6—C11	1.382 (4)	N1—H1	0.9100
C7—C8	1.386 (4)	N2—H2	0.9100
C7—H7	0.9300	N3—C1^i	1.431 (3)
C8—C9	1.378 (5)	N4—H4	0.9100
C8—H8	0.9300	N5—H5	0.9100
C9—C10	1.363 (4)	N6—C12^ii	1.427 (3)
C9—H9	0.9300	Cl1—O14	1.387 (2)
C10—C11	1.388 (4)	Cl1—O11	1.4082 (18)
C10—H10	0.9300	Cl1—O12	1.422 (2)
C11—H11	0.9300	Cl1—O13	1.441 (2)
C12—N6^ii	1.427 (3)	Cl2—O24	1.369 (3)
C12—N4	1.502 (3)	Cl2—O22	1.411 (2)
C12—H12A	0.9700	Cl2—O21	1.4156 (18)
C12—H12B	0.9700	Cl2—O23	1.433 (2)
N1—Ni1—N2	86.66 (7)	N5—C14—H14B	110.5
N1^i—Ni1—N2	93.34 (7)	C13—C14—H14B	110.5
N1—Ni1—O12	100.60 (8)	H14A—C14—H14B	108.7
N1^i—Ni1—O12	79.40 (8)	N6—C15—N5	113.97 (17)
N2—Ni1—O12	93.11 (7)	N6—C15—H15A	108.8
N2^i—Ni1—O12	86.89 (7)	N5—C15—H15A	108.8
N4—Ni2—N5	86.70 (7)	N6—C15—H15B	108.8
N4^ii—Ni2—N5	93.30 (7)	N5—C15—H15B	108.8
N4—Ni2—O22	97.51 (7)	H15A—C15—H15B	107.7
N4^ii—Ni2—O22	82.49 (7)	N6—C16—C17	111.14 (18)
N5—Ni2—O22	99.83 (9)	N6—C16—H16A	109.4
N5^ii—Ni2—O22	80.17 (9)	C17—C16—H16A	109.4
N3^i—C1—N1	113.94 (17)	N6—C16—H16B	109.4
N3^i—C1—H1A	108.8	C17—C16—H16B	109.4
N1—C1—H1A	108.8	H16A—C16—H16B	108.0
N3^i—C1—H1B	108.8	C18—C17—C22	118.5 (2)
N1—C1—H1B	108.8	C18—C17—C16	121.1 (2)
H1A—C1—H1B	107.7	C22—C17—C16	120.3 (2)
N1—C2—C3	106.59 (18)	C17—C18—C19	120.3 (3)
N1—C2—H2A	110.4	C17—C18—H18	119.9
C3—C2—H2A	110.4	C19—C18—H18	119.9
N1—C2—H2B	110.4	C20—C19—C18	120.2 (3)
C3—C2—H2B	110.4	C20—C19—H19	119.9
H2A—C2—H2B	108.6	C18—C19—H19	119.9
N2—C3—C2	107.05 (19)	C19—C20—C21	120.3 (3)
N2—C3—H3A	110.3	C19—C20—H20	119.8
C2—C3—H3A	110.3	C21—C20—H20	119.8
N2—C3—H3B	110.3	C20—C21—C22	119.9 (3)
C2—C3—H3B	110.3	C20—C21—H21	120.1
H3A—C3—H3B	108.6	C22—C21—H21	120.1
N3—C4—N2	114.45 (18)	C21—C22—C17	120.7 (2)
N3—C4—H4A	108.6	C21—C22—H22	119.6
N2—C4—H4A	108.6	C17—C22—H22	119.6
N3—C4—H4B	108.6	C2—N1—C1	110.69 (17)
N2—C4—H4B	108.6	C2—N1—Ni1	109.20 (13)
H4A—C4—H4B	107.6	C1—N1—Ni1	116.87 (14)
N3—C5—C6	113.32 (19)	C2—N1—H1	106.5
N3—C5—H5A	108.9	C1—N1—H1	106.5
C6—C5—H5A	108.9	Ni1—N1—H1	106.5
N3—C5—H5B	108.9	C3—N2—C4	110.50 (18)
C6—C5—H5B	108.9	C3—N2—Ni1	108.53 (14)
H5A—C5—H5B	107.7	C4—N2—Ni1	117.16 (14)
C7—C6—C11	118.2 (2)	C3—N2—H2	106.7
C7—C6—C5	120.8 (2)	C4—N2—H2	106.7
C11—C6—C5	121.0 (2)	Ni1—N2—H2	106.7
C6—C7—C8	120.8 (3)	C4—N3—C1^i	113.60 (18)
C6—C7—H7	119.6	C4—N3—C5	116.03 (19)
C8—C7—H7	119.6	C1^i—N3—C5	113.48 (19)
C9—C8—C7	120.0 (3)	C13—N4—C12	110.37 (16)
C9—C8—H8	120.0	C13—N4—Ni2	108.90 (12)
C7—C8—H8	120.0	C12—N4—Ni2	116.98 (14)
C10—C9—C8	119.9 (3)	C13—N4—H4	106.7
C10—C9—H9	120.0	C12—N4—H4	106.7
C8—C9—H9	120.0	Ni2—N4—H4	106.7
C9—C10—C11	120.0 (3)	C14—N5—C15	110.04 (16)
C9—C10—H10	120.0	C14—N5—Ni2	109.00 (12)
C11—C10—H10	120.0	C15—N5—Ni2	117.86 (13)
C6—C11—C10	121.0 (3)	C14—N5—H5	106.4
C6—C11—H11	119.5	C15—N5—H5	106.4
C10—C11—H11	119.5	Ni2—N5—H5	106.4
N6^ii—C12—N4	114.05 (18)	C15—N6—C12^ii	115.04 (18)
N6^ii—C12—H12A	108.7	C15—N6—C16	115.85 (19)
N4—C12—H12A	108.7	C12^ii—N6—C16	118.18 (19)
N6^ii—C12—H12B	108.7	O14—Cl1—O11	110.92 (16)
N4—C12—H12B	108.7	O14—Cl1—O12	109.43 (18)
H12A—C12—H12B	107.6	O11—Cl1—O12	111.66 (15)
N4—C13—C14	106.83 (17)	O14—Cl1—O13	109.4 (2)
N4—C13—H13A	110.4	O11—Cl1—O13	108.84 (15)
C14—C13—H13A	110.4	O12—Cl1—O13	106.45 (16)
N4—C13—H13B	110.4	O24—Cl2—O22	109.1 (3)
C14—C13—H13B	110.4	O24—Cl2—O21	110.85 (18)
H13A—C13—H13B	108.6	O22—Cl2—O21	111.45 (15)
N5—C14—C13	106.27 (17)	O24—Cl2—O23	108.9 (3)
N5—C14—H14A	110.5	O22—Cl2—O23	105.89 (18)
C13—C14—H14A	110.5	O21—Cl2—O23	110.45 (13)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21^iii	0.91	2.25	3.024 (3)	142
N1—H1···O12^i	0.91	2.50	3.042 (3)	118
N2—H2···O13	0.91	2.23	3.094 (3)	158
N4—H4···O23	0.91	2.17	3.020 (3)	155
N5—H5···O11^iv	0.91	2.18	2.947 (3)	142

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