Supramolecular self-assembly via inter-ligands hydrogen bonds in [Cu(H₂O)₂(NO₃)₂(tb)] (tb is thia­bendazole)

In the title complex, di­aqua­dinitrato­[2-(4-thia­zolyl)­benz­imidazole]copper(II), [Cu(NO₃)₂(C₁₀H₇N₃S)(H₂O)₂], the Cu atom has a distorted octahedral geometry. Thia­bendazole [2-(4-thia­zolyl)­benz­imidazole] acts as a neutral bidentate chelate, coordinating through the imidazole and thia­zole N atoms. The equatorial positions are occupied by the two N atoms of the thia­bendazole mol­ecule and two O atoms of two water mol­ecules. The axial positions are occupied by two O atoms of two nitrate ions acting as monodentate ligands. The complex units are further self-assembled into a supramolecular motif by extensive inter-ligand O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.029
• wR factor = 0.077
• Data-to-parameter ratio = 9.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_031  Alert B Refined Extinction parameter within range ....       2.00 Sigma


 Alert Level C:



PLAT_354  Alert C Short O-H Bond (0.82A)     O(1)   -   H(1B)  =       0.71 Ang.

PLAT_354  Alert C Short O-H Bond (0.82A)     O(2)   -   H(2A)  =       0.71 Ang.

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.729
          Tmax scaled      0.722 Tmin scaled      0.649


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXS97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1997).

(I)

Crystal data

[Cu(NO3)2(C10H7N3S)(H2O)2]	F(000) = 860
Mr = 424.86	Dx = 1.856 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.580 (4) Å	Cell parameters from 25 reflections
b = 20.065 (5) Å	θ = 10–15°
c = 10.606 (2) Å	µ = 1.63 mm^−1
β = 109.51 (3)°	T = 293 K
V = 1520.4 (10) Å^3	Plate, green
Z = 4	0.3 × 0.3 × 0.2 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	2057 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω–2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→23
Tmin = 0.89, Tmax = 0.99	l = −12→11
2857 measured reflections	2 standard reflections every 60 min
2649 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	All H-atom parameters refined
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0263P)^2 + 1.6719P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
2649 reflections	Δρmax = 0.35 e Å^−3
271 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0008 (4)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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

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

	x	y	z	Uiso*/Ueq
Cu1	0.12303 (6)	0.34522 (2)	0.40545 (4)	0.0300 (1)
S12	0.22328 (14)	0.39105 (5)	0.84313 (8)	0.0427 (3)
O1	0.1192 (5)	0.32379 (14)	0.2246 (3)	0.0381 (9)
O2	0.0144 (4)	0.25740 (12)	0.4247 (3)	0.0340 (8)
O4A	−0.4458 (4)	0.39494 (14)	0.1393 (3)	0.0679 (11)
O4B	−0.2041 (3)	0.37774 (12)	0.3127 (2)	0.0420 (8)
O4C	−0.2653 (3)	0.31208 (12)	0.1416 (2)	0.0446 (8)
O5A	0.4214 (3)	0.28082 (14)	0.4971 (2)	0.0508 (9)
O5B	0.6912 (4)	0.25019 (15)	0.4934 (3)	0.0602 (10)
O5C	0.4724 (4)	0.27265 (17)	0.3096 (3)	0.0677 (13)
N1	0.2067 (4)	0.43931 (12)	0.3953 (2)	0.0287 (8)
N3	0.2756 (4)	0.53739 (14)	0.4974 (3)	0.0326 (9)
N4	−0.3087 (4)	0.36156 (13)	0.1961 (3)	0.0347 (9)
N5	0.5286 (4)	0.26820 (14)	0.4331 (3)	0.0391 (10)
N14	0.1614 (4)	0.37313 (13)	0.5956 (2)	0.0306 (8)
C2	0.2364 (4)	0.47293 (15)	0.5080 (3)	0.0282 (9)
C4	0.2924 (5)	0.60482 (18)	0.2995 (4)	0.0412 (11)
C5	0.2721 (6)	0.5977 (2)	0.1663 (4)	0.0460 (12)
C6	0.2313 (6)	0.5361 (2)	0.1028 (4)	0.0474 (16)
C7	0.2072 (5)	0.47919 (19)	0.1679 (3)	0.0390 (11)
C8	0.2256 (4)	0.48586 (15)	0.3030 (3)	0.0297 (10)
C9	0.2685 (4)	0.54799 (16)	0.3663 (3)	0.0313 (10)
C10	0.2220 (4)	0.43802 (15)	0.6237 (3)	0.0295 (10)
C11	0.2620 (5)	0.45627 (18)	0.7527 (3)	0.0368 (11)
C13	0.1551 (5)	0.34309 (19)	0.7031 (3)	0.0376 (11)
H1A	0.208 (7)	0.308 (2)	0.230 (5)	0.061 (17)*
H1B	0.037 (8)	0.307 (3)	0.185 (5)	0.09 (2)*
H2A	0.061 (5)	0.2372 (17)	0.481 (3)	0.020 (10)*
H2B	−0.094 (6)	0.259 (2)	0.425 (4)	0.053 (14)*
H3	0.291 (5)	0.5637 (18)	0.554 (3)	0.036 (10)*
H4	0.321 (5)	0.6457 (17)	0.337 (3)	0.036 (10)*
H5	0.287 (6)	0.634 (2)	0.122 (4)	0.069 (14)*
H6	0.230 (5)	0.5350 (19)	0.022 (4)	0.054 (12)*
H7	0.183 (5)	0.4374 (19)	0.130 (4)	0.045 (10)*
H11	0.305 (5)	0.4950 (17)	0.794 (3)	0.035 (9)*
H13	0.121 (5)	0.3000 (19)	0.704 (4)	0.047 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0398 (2)	0.0255 (2)	0.0259 (2)	−0.0024 (2)	0.0126 (2)	−0.0043 (2)
S12	0.0596 (6)	0.0438 (5)	0.0255 (4)	0.0027 (4)	0.0151 (4)	0.0007 (4)
O1	0.0405 (17)	0.0424 (15)	0.0330 (14)	−0.0031 (14)	0.0143 (13)	−0.0096 (11)
O2	0.0324 (16)	0.0302 (13)	0.0365 (14)	0.0025 (11)	0.0076 (12)	0.0062 (11)
O4A	0.0557 (18)	0.0588 (19)	0.0653 (19)	0.0211 (15)	−0.0117 (15)	−0.0047 (15)
O4B	0.0396 (14)	0.0441 (14)	0.0347 (13)	0.0069 (11)	0.0022 (11)	−0.0143 (11)
O4C	0.0432 (15)	0.0455 (15)	0.0423 (14)	−0.0011 (12)	0.0106 (12)	−0.0207 (12)
O5A	0.0372 (14)	0.079 (2)	0.0419 (14)	0.0059 (13)	0.0206 (12)	−0.0038 (13)
O5B	0.0360 (16)	0.085 (2)	0.0636 (18)	0.0198 (15)	0.0219 (14)	0.0257 (16)
O5C	0.0576 (19)	0.108 (3)	0.0430 (16)	0.0225 (18)	0.0241 (14)	0.0014 (16)
N1	0.0345 (15)	0.0261 (14)	0.0249 (13)	−0.0010 (11)	0.0092 (12)	−0.0027 (10)
N3	0.0414 (17)	0.0262 (15)	0.0288 (14)	−0.0030 (12)	0.0098 (13)	−0.0064 (12)
N4	0.0322 (16)	0.0344 (16)	0.0325 (15)	−0.0004 (12)	0.0043 (13)	−0.0017 (12)
N5	0.0386 (18)	0.0383 (16)	0.0458 (18)	−0.0009 (14)	0.0214 (15)	0.0018 (14)
N14	0.0388 (16)	0.0276 (14)	0.0263 (14)	0.0002 (12)	0.0120 (12)	−0.0009 (11)
C2	0.0317 (18)	0.0258 (16)	0.0251 (15)	0.0015 (13)	0.0070 (14)	−0.0027 (12)
C4	0.046 (2)	0.0318 (19)	0.047 (2)	−0.0039 (16)	0.0172 (18)	0.0019 (16)
C5	0.055 (2)	0.041 (2)	0.048 (2)	−0.0033 (18)	0.0251 (19)	0.0111 (18)
C6	0.057 (3)	0.059 (3)	0.032 (2)	−0.001 (2)	0.0226 (19)	0.0066 (18)
C7	0.051 (2)	0.041 (2)	0.0285 (17)	−0.0036 (17)	0.0178 (16)	−0.0048 (15)
C8	0.0304 (17)	0.0296 (17)	0.0299 (16)	−0.0006 (14)	0.0110 (14)	0.0008 (13)
C9	0.0291 (18)	0.0320 (17)	0.0324 (17)	0.0004 (14)	0.0097 (14)	−0.0016 (14)
C10	0.0332 (18)	0.0272 (16)	0.0278 (16)	0.0022 (14)	0.0097 (14)	−0.0030 (13)
C11	0.047 (2)	0.0349 (19)	0.0271 (17)	0.0013 (16)	0.0104 (15)	−0.0040 (15)
C13	0.047 (2)	0.0327 (19)	0.0358 (18)	−0.0010 (17)	0.0176 (16)	−0.0005 (16)

Geometric parameters (Å, º)

Cu1—O1	1.956 (3)	N3—C9	1.390 (4)
Cu1—O2	1.984 (3)	N3—C2	1.340 (4)
Cu1—O4B	2.432 (3)	N14—C13	1.305 (4)
Cu1—O5A	2.502 (3)	N14—C10	1.380 (4)
Cu1—N1	2.006 (3)	N3—H3	0.78 (3)
Cu1—N14	2.018 (2)	C2—C10	1.448 (4)
S12—C11	1.705 (4)	C4—C9	1.386 (5)
S12—C13	1.699 (4)	C4—C5	1.376 (6)
O4A—N4	1.214 (4)	C5—C6	1.392 (6)
O4B—N4	1.268 (4)	C6—C7	1.378 (6)
O4C—N4	1.247 (4)	C7—C8	1.399 (4)
O5A—N5	1.246 (4)	C8—C9	1.402 (4)
O5B—N5	1.238 (4)	C10—C11	1.349 (4)
O5C—N5	1.238 (4)	C4—H4	0.91 (3)
O1—H1B	0.71 (6)	C5—H5	0.89 (4)
O1—H1A	0.73 (5)	C6—H6	0.85 (4)
O2—H2B	0.82 (5)	C7—H7	0.92 (4)
O2—H2A	0.71 (3)	C11—H11	0.90 (3)
N1—C8	1.395 (4)	C13—H13	0.90 (4)
N1—C2	1.325 (4)
Cu1···O4C	3.382 (3)	O5B···H2A^x	2.86 (4)
Cu1···O5C	3.459 (4)	O5C···H1A	2.03 (5)
Cu1···N3	4.050 (4)	O5C···H13^ix	2.34 (4)
Cu1···O4C^i	3.941 (3)	N3···Cu1	4.050 (4)
Cu1···H7	3.61 (4)	N3···O4B^iii	2.825 (4)
S12···O4A^ii	3.302 (4)	N4···O5C^vi	2.953 (5)
S12···C4^iii	3.691 (5)	N4···H1B	2.88 (6)
S12···O5B^iv	3.300 (4)	N4···H11^iii	2.88 (3)
O1···O4C	2.759 (5)	N4···H2A^v	2.93 (3)
O1···O5C	2.724 (5)	N5···H1A	2.77 (5)
O1···C7	3.286 (5)	N5···H2B^x	2.90 (5)
O1···O5A^v	3.172 (4)	N5···H4^viii	2.89 (3)
O1···O5B^v	3.067 (5)	C2···C9^viii	3.563 (5)
O2···O4C	3.235 (4)	C4···S12^iii	3.691 (5)
O2···O5B^vi	2.783 (5)	C4···O5A^viii	3.391 (5)
O2···O4C^i	2.731 (4)	C4···C10^viii	3.598 (5)
O4A···O5C^vi	3.227 (5)	C4···C13^iii	3.541 (6)
O4A···S12^vii	3.302 (4)	C5···C11^viii	3.515 (6)
O4A···C11^iii	3.332 (5)	C7···O1	3.286 (5)
O4A···C7^vi	3.225 (5)	C7···O4A^x	3.225 (5)
O4B···O5C^vi	3.226 (4)	C9···C2^viii	3.563 (5)
O4B···C11^iii	3.400 (5)	C10···C4^viii	3.598 (5)
O4B···N3^iii	2.825 (4)	C11···C5^viii	3.515 (6)
O4C···O1	2.759 (5)	C11···O4A^iii	3.332 (5)
O4C···O5A^v	3.045 (4)	C11···O4B^iii	3.400 (5)
O4C···Cu1	3.382 (3)	C13···O5C^iv	3.104 (5)
O4C···Cu1^v	3.941 (3)	C13···C4^iii	3.541 (6)
O4C···O2^v	2.731 (4)	C13···O4C^i	3.278 (5)
O4C···O5C^vi	3.181 (4)	C11···H3	3.07 (3)
O4C···C13^v	3.278 (5)	C13···H2A	3.07 (3)
O4C···O2	3.235 (4)	H1A···O5C	2.03 (5)
O5A···O4C^i	3.045 (4)	H1A···N5	2.77 (5)
O5A···C4^viii	3.391 (5)	H1A···O5B^v	2.73 (5)
O5A···O1^i	3.172 (4)	H1B···O4C	2.18 (6)
O5B···S12^ix	3.300 (4)	H1B···N4	2.88 (6)
O5B···O1^i	3.067 (5)	H1B···O5A^v	2.58 (6)
O5B···O2^x	2.783 (5)	H1B···O5B^v	2.90 (6)
O5C···O1	2.724 (5)	H2A···O5B^vi	2.86 (4)
O5C···C13^ix	3.104 (5)	H2A···C13	3.07 (3)
O5C···O4C^x	3.181 (4)	H2A···H13	2.58 (5)
O5C···O4B^x	3.226 (4)	H2A···O4C^i	2.03 (3)
O5C···N4^x	2.953 (5)	H2A···N4^i	2.93 (3)
O5C···Cu1	3.459 (4)	H2B···O5B^vi	2.00 (5)
O5C···O4A^x	3.227 (5)	H2B···N5^vi	2.90 (5)
O1···H7	2.60 (4)	H3···C11	3.07 (3)
O4A···H7^vi	2.91 (4)	H3···O4B^iii	2.11 (3)
O4A···H11^iii	2.45 (3)	H4···O5A^viii	2.61 (3)
O4B···H3^iii	2.11 (3)	H4···O5B^viii	2.78 (3)
O4B···H11^iii	2.79 (3)	H4···N5^viii	2.89 (3)
O4C···H1B	2.18 (6)	H7···Cu1	3.61 (4)
O4C···H13^v	2.57 (4)	H7···O1	2.60 (4)
O4C···H2A^v	2.03 (3)	H7···O4A^x	2.91 (4)
O5A···H1B^i	2.58 (6)	H11···O4A^iii	2.45 (3)
O5A···H4^viii	2.61 (3)	H11···O4B^iii	2.79 (3)
O5B···H1B^i	2.90 (6)	H11···N4^iii	2.88 (3)
O5B···H4^viii	2.78 (3)	H13···H2A	2.58 (5)
O5B···H2B^x	2.00 (5)	H13···O4C^i	2.57 (4)
O5B···H1A^i	2.73 (5)	H13···O5C^iv	2.34 (4)
O1—Cu1—O2	92.00 (13)	Cu1—N14—C10	113.84 (19)
O1—Cu1—O4B	89.03 (12)	C10—N14—C13	110.7 (3)
O1—Cu1—O5A	89.02 (12)	C2—N3—H3	125 (2)
O1—Cu1—N1	93.19 (11)	C9—N3—H3	128 (2)
O1—Cu1—N14	172.14 (14)	N1—C2—C10	118.7 (3)
O2—Cu1—O4B	82.98 (11)	N3—C2—C10	128.3 (3)
O2—Cu1—O5A	81.59 (11)	N1—C2—N3	113.0 (3)
O2—Cu1—N1	172.25 (13)	C5—C4—C9	116.8 (3)
O2—Cu1—N14	94.01 (12)	C4—C5—C6	121.3 (4)
O4B—Cu1—O5A	164.37 (9)	C5—C6—C7	122.6 (4)
O4B—Cu1—N1	91.36 (11)	C6—C7—C8	116.7 (3)
O4B—Cu1—N14	96.72 (10)	N1—C8—C7	131.0 (3)
O5A—Cu1—N1	104.24 (11)	N1—C8—C9	108.7 (3)
O5A—Cu1—N14	86.86 (10)	C7—C8—C9	120.2 (3)
N1—Cu1—N14	81.36 (10)	N3—C9—C8	105.6 (3)
C11—S12—C13	90.13 (17)	C4—C9—C8	122.4 (3)
Cu1—O4B—N4	123.1 (2)	N3—C9—C4	132.0 (3)
Cu1—O5A—N5	124.22 (19)	N14—C10—C2	112.8 (3)
Cu1—O1—H1A	108 (4)	N14—C10—C11	114.9 (3)
Cu1—O1—H1B	114 (5)	C2—C10—C11	132.3 (3)
H1A—O1—H1B	116 (6)	S12—C11—C10	109.8 (3)
Cu1—O2—H2A	119 (3)	S12—C13—N14	114.4 (3)
Cu1—O2—H2B	115 (3)	C5—C4—H4	118 (2)
H2A—O2—H2B	104 (4)	C9—C4—H4	125 (2)
Cu1—N1—C2	113.1 (2)	C4—C5—H5	118 (3)
Cu1—N1—C8	140.94 (19)	C6—C5—H5	121 (3)
C2—N1—C8	105.4 (2)	C5—C6—H6	116 (3)
C2—N3—C9	107.2 (3)	C7—C6—H6	121 (3)
O4A—N4—O4C	121.6 (3)	C6—C7—H7	125 (3)
O4B—N4—O4C	118.7 (3)	C8—C7—H7	118 (3)
O4A—N4—O4B	119.7 (3)	S12—C11—H11	119 (2)
O5A—N5—O5C	120.3 (3)	C10—C11—H11	131 (2)
O5A—N5—O5B	119.7 (3)	S12—C13—H13	123 (3)
O5B—N5—O5C	119.9 (3)	N14—C13—H13	123 (3)
Cu1—N14—C13	135.2 (2)
O1—Cu1—O4B—N4	16.5 (2)	C8—N1—C2—C10	178.6 (3)
O2—Cu1—O4B—N4	−75.7 (2)	C2—N1—C8—C7	−179.1 (4)
N1—Cu1—O4B—N4	109.7 (2)	C2—N1—C8—C9	0.3 (4)
N14—Cu1—O4B—N4	−168.9 (2)	Cu1—N1—C2—C10	5.2 (4)
O1—Cu1—O5A—N5	21.3 (3)	Cu1—N1—C8—C7	−8.7 (6)
O2—Cu1—O5A—N5	113.5 (3)	C9—N3—C2—N1	1.0 (4)
N1—Cu1—O5A—N5	−71.7 (3)	C2—N3—C9—C8	−0.8 (4)
N14—Cu1—O5A—N5	−152.0 (3)	C9—N3—C2—C10	−178.3 (3)
O1—Cu1—N1—C2	−177.0 (3)	C2—N3—C9—C4	178.2 (4)
O4B—Cu1—N1—C2	93.9 (2)	C10—N14—C13—S12	−0.5 (4)
O5A—Cu1—N1—C2	−87.2 (2)	C13—N14—C10—C11	0.4 (4)
N14—Cu1—N1—C2	−2.7 (2)	Cu1—N14—C13—S12	173.9 (2)
O1—Cu1—N1—C8	13.1 (4)	Cu1—N14—C10—C11	−175.3 (3)
O4B—Cu1—N1—C8	−76.0 (4)	C13—N14—C10—C2	178.4 (3)
O5A—Cu1—N1—C8	102.9 (4)	Cu1—N14—C10—C2	2.7 (4)
N14—Cu1—N1—C8	−172.6 (4)	N1—C2—C10—N14	−5.3 (4)
N1—Cu1—N14—C10	−0.1 (2)	N1—C2—C10—C11	172.2 (4)
O2—Cu1—N14—C13	11.9 (4)	N3—C2—C10—N14	174.0 (3)
O4B—Cu1—N14—C13	95.3 (4)	N3—C2—C10—C11	−8.4 (6)
O5A—Cu1—N14—C13	−69.4 (4)	C5—C4—C9—N3	−178.8 (4)
O2—Cu1—N14—C10	−173.9 (2)	C9—C4—C5—C6	−0.6 (6)
O4B—Cu1—N14—C10	−90.5 (2)	C5—C4—C9—C8	0.0 (6)
O5A—Cu1—N14—C10	104.8 (2)	C4—C5—C6—C7	0.6 (7)
N1—Cu1—N14—C13	−174.4 (4)	C5—C6—C7—C8	0.0 (6)
C11—S12—C13—N14	0.4 (3)	C6—C7—C8—C9	−0.7 (5)
C13—S12—C11—C10	−0.2 (3)	C6—C7—C8—N1	178.7 (4)
Cu1—O4B—N4—O4A	−156.4 (3)	C7—C8—C9—C4	0.7 (5)
Cu1—O4B—N4—O4C	22.3 (4)	N1—C8—C9—N3	0.3 (4)
Cu1—O5A—N5—O5B	163.2 (2)	N1—C8—C9—C4	−178.8 (3)
Cu1—O5A—N5—O5C	−17.9 (4)	C7—C8—C9—N3	179.7 (3)
Cu1—N1—C8—C9	170.7 (3)	N14—C10—C11—S12	−0.1 (4)
Cu1—N1—C2—N3	−174.3 (2)	C2—C10—C11—S12	−177.6 (3)
C8—N1—C2—N3	−0.8 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O5C	0.73 (5)	2.03 (5)	2.724 (5)	161 (5)
O1—H1B···O4C	0.71 (6)	2.18 (6)	2.759 (5)	139 (6)
O1—H1B···O5A^v	0.71 (6)	2.58 (6)	3.172 (4)	142 (6)
O2—H2A···O4C^i	0.71 (3)	2.03 (3)	2.731 (4)	170 (4)
O2—H2B···O5B^vi	0.82 (5)	2.00 (5)	2.783 (5)	159 (4)
N3—H3···O4B^iii	0.78 (3)	2.11 (3)	2.825 (4)	154 (4)
C11—H11···O4A^iii	0.90 (3)	2.45 (3)	3.332 (5)	166 (3)
C13—H13···O4C^i	0.90 (4)	2.57 (4)	3.278 (5)	135 (3)
C13—H13···O5C^iv	0.90 (4)	2.34 (4)	3.104 (5)	142 (3)

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