L-Isoleucyl-L-asparagine 1.094-hydrate: a hybrid hydrogen-bonding pattern

The title compound, C₁₀H₂₀N₃O₄·1.094H₂O, crystallizes with two dipeptide mol­ecules in the asymmetric unit, each participating in two head-to-tail chains with hydrogen bonds between the terminal amino and carboxyl­ate groups. As with many other dipeptides, the resulting structure is divided into distinct layers, but as the amide groups of the two peptide mol­ecules participate in different types of inter­action, the observed hydrogen bonds within a peptide main-chain layer (as distinct from the side-chain/solvent regions) cannot adapt to any of the four basic patterns observed previously for dipeptides. Instead, a rare hybrid pattern is formed.

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

L-Isoleucyl-L-asparagine

Crystal data

C10H19N3O4·1.094H2O	Dx = 1.287 Mg m^−3
Mr = 265.01	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 50.56 reflections
a = 4.7855 (4) Å	θ = 1.3–28.3°
b = 18.2887 (15) Å	µ = 0.10 mm^−1
c = 31.247 (3) Å	T = 105 K
V = 2734.8 (4) Å^3	Block, colourless
Z = 8	0.78 × 0.50 × 0.22 mm
F(000) = 1144

Data collection

Bruker APEXII CCD area-detector diffractometer	3860 independent reflections
Radiation source: fine-focus sealed tube	2902 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 8.3 pixels mm^-1	θmax = 28.3°, θmin = 1.3°
Three sets of frames each taken over 0.3° ω rotation with 20 s exposure time. Detector set at 2θ = 26°, crystal–to–detector distance 6.00 cm. scans	h = −5→6
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −24→21
Tmin = 0.751, Tmax = 0.978	l = −40→41
18243 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.6738P] where P = (Fo^2 + 2Fc^2)/3
3860 reflections	(Δ/σ)max = 0.001
376 parameters	Δρmax = 0.22 e Å^−3
25 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. Crystallized from water and 2-propanol

Refinement. Refinement of F² against ALL reflections.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	1.2190 (3)	0.45870 (9)	0.26437 (5)	0.0268 (4)
O2A	1.1326 (4)	0.29647 (9)	0.20361 (7)	0.0501 (6)
N1A	0.9555 (4)	0.41979 (9)	0.34181 (5)	0.0212 (4)
H1A	0.9141	0.3737	0.3329	0.032*
H2A	0.8832	0.4271	0.3684	0.032*
H3A	1.1443	0.4256	0.3427	0.032*
N2A	0.7851 (3)	0.44876 (8)	0.23547 (5)	0.0155 (4)
H4A	0.6050	0.4485	0.2411	0.019*
N3A	0.7000 (4)	0.25330 (9)	0.21399 (6)	0.0287 (5)
H5A	0.7613	0.2152	0.2284	0.034*
H6A	0.5196	0.2591	0.2097	0.034*
C1A	0.8328 (4)	0.47381 (10)	0.31154 (6)	0.0164 (4)
H11A	0.6263	0.4659	0.3098	0.020*
C2A	0.8904 (5)	0.55316 (11)	0.32538 (6)	0.0208 (5)
H21A	1.0968	0.5616	0.3242	0.025*
C3A	0.7907 (7)	0.56896 (12)	0.37101 (7)	0.0376 (7)
H31A	0.5854	0.5626	0.3722	0.045*
H32A	0.8756	0.5328	0.3907	0.045*
C4A	0.8639 (8)	0.64568 (14)	0.38650 (8)	0.0525 (9)
H41A	0.8245	0.6496	0.4172	0.079*
H42A	0.7515	0.6816	0.3709	0.079*
H43A	1.0627	0.6551	0.3814	0.079*
C5A	0.7509 (6)	0.60483 (11)	0.29337 (7)	0.0324 (6)
H51A	0.7966	0.6555	0.3008	0.049*
H52A	0.5479	0.5980	0.2944	0.049*
H53A	0.8189	0.5940	0.2645	0.049*
C6A	0.9630 (4)	0.45919 (10)	0.26765 (6)	0.0163 (4)
C8A	0.7595 (5)	0.36546 (10)	0.17401 (6)	0.0204 (5)
H81A	0.5533	0.3651	0.1764	0.024*
H82A	0.8092	0.3607	0.1434	0.024*
C9A	0.8793 (5)	0.30183 (11)	0.19866 (7)	0.0247 (5)
C7A	0.8735 (4)	0.43776 (10)	0.19150 (6)	0.0159 (4)	0.812 (2)
H71A	1.0819	0.4337	0.1917	0.019*	0.812 (2)
C10A	0.7989 (5)	0.50320 (10)	0.16254 (6)	0.0181 (5)	0.812 (2)
O3A	0.7196 (4)	0.56185 (7)	0.18000 (5)	0.0226 (4)	0.812 (2)
O4A	0.8293 (4)	0.49360 (9)	0.12294 (4)	0.0199 (4)	0.812 (2)
C71A	0.8735 (4)	0.43776 (10)	0.19150 (6)	0.0159 (4)	0.188 (2)
H72A	1.0822	0.4353	0.1910	0.019*	0.188 (2)
C11A	0.7808 (11)	0.4991 (2)	0.16068 (10)	0.0181 (5)	0.188 (2)
O31A	0.6080 (9)	0.5460 (2)	0.17402 (14)	0.030*	0.188 (2)
O41A	0.8709 (14)	0.4947 (3)	0.12293 (9)	0.0199 (4)	0.188 (2)
O1B	0.5777 (3)	0.39876 (7)	0.52851 (4)	0.0202 (3)
O2B	0.5780 (3)	0.19722 (7)	0.41309 (5)	0.0215 (3)
O3B	0.7463 (3)	0.41106 (7)	0.42507 (4)	0.0208 (3)
O4B	0.4277 (3)	0.37045 (8)	0.37892 (4)	0.0259 (4)
N1B	0.1538 (4)	0.45197 (8)	0.58124 (5)	0.0178 (4)
H1B	0.1400	0.4026	0.5843	0.027*
H2B	0.0033	0.4738	0.5936	0.027*
H3B	0.3130	0.4680	0.5941	0.027*
N2B	0.2361 (3)	0.38184 (8)	0.47855 (5)	0.0152 (4)
H4B	0.0634	0.3927	0.4713	0.018*
N3B	0.1701 (4)	0.18564 (9)	0.37793 (5)	0.0233 (4)
H5B	0.2387	0.1518	0.3609	0.028*
H6B	−0.0047	0.1998	0.3751	0.028*
C1B	0.1623 (4)	0.47080 (10)	0.53461 (6)	0.0165 (4)
H11B	−0.0306	0.4684	0.5224	0.020*
C2B	0.2835 (5)	0.54817 (10)	0.52808 (6)	0.0209 (5)
H21B	0.4688	0.5503	0.5428	0.025*
C3B	0.0949 (6)	0.60635 (11)	0.54807 (8)	0.0361 (7)
H31B	−0.0792	0.6097	0.5311	0.043*
H32B	0.0431	0.5905	0.5773	0.043*
C4B	0.2264 (7)	0.68202 (13)	0.55069 (10)	0.0517 (8)
H41B	0.3975	0.6796	0.5678	0.078*
H42B	0.0945	0.7160	0.5641	0.078*
H43B	0.2717	0.6992	0.5218	0.078*
C5B	0.3320 (6)	0.56207 (12)	0.48041 (7)	0.0345 (6)
H51B	0.4683	0.5268	0.4694	0.052*
H52B	0.4036	0.6118	0.4764	0.052*
H53B	0.1553	0.5566	0.4649	0.052*
C6B	0.3452 (4)	0.41319 (10)	0.51357 (6)	0.0159 (4)
C7B	0.3928 (4)	0.33022 (10)	0.45191 (6)	0.0140 (4)
H71B	0.5409	0.3065	0.4697	0.017*
C8B	0.1922 (4)	0.27172 (10)	0.43579 (6)	0.0176 (5)
H81B	0.1065	0.2469	0.4607	0.021*
H82B	0.0404	0.2956	0.4194	0.021*
C9B	0.3301 (4)	0.21541 (10)	0.40785 (6)	0.0161 (4)
C10B	0.5334 (4)	0.37404 (10)	0.41555 (6)	0.0158 (4)
O1W	0.7319 (5)	0.28591 (11)	0.32034 (7)	0.0442 (6)	0.812 (2)
H11W	0.718 (6)	0.2417 (5)	0.3121 (8)	0.066*	0.812 (2)
H12W	0.587 (3)	0.2942 (11)	0.3360 (6)	0.066*	0.812 (2)
O2W	0.7654 (4)	0.14272 (9)	0.29047 (6)	0.0448 (5)
H22W	0.630 (2)	0.1143 (7)	0.2960 (9)	0.067*
H21W	0.912 (2)	0.1204 (12)	0.2988 (10)	0.067*	0.812 (2)
H23W	0.699 (6)	0.1857 (6)	0.293 (3)	0.067*	0.188 (2)
O3W	1.1345 (19)	0.2854 (4)	0.2968 (2)	0.042 (2)*	0.188 (2)
H31W	1.164 (9)	0.293 (2)	0.2702 (3)	0.064*	0.188 (2)
H32W	1.044 (5)	0.2453 (9)	0.2971 (14)	0.064*	0.188 (2)
O4W	0.4496 (18)	0.2933 (7)	0.2991 (3)	0.077 (4)*	0.188 (2)
H41W	0.412 (6)	0.301 (2)	0.3253 (5)	0.116*	0.188 (2)
H42W	0.629 (2)	0.291 (9)	0.2981 (15)	0.116*	0.188 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0074 (7)	0.0504 (9)	0.0227 (7)	0.0015 (7)	0.0009 (6)	0.0002 (7)
O2A	0.0154 (8)	0.0245 (8)	0.1103 (17)	0.0016 (7)	−0.0026 (10)	0.0180 (9)
N1A	0.0164 (9)	0.0282 (9)	0.0191 (8)	0.0036 (8)	−0.0007 (7)	0.0041 (7)
N2A	0.0080 (8)	0.0207 (8)	0.0177 (7)	0.0003 (7)	0.0023 (7)	0.0041 (6)
N3A	0.0156 (9)	0.0228 (8)	0.0478 (11)	0.0000 (8)	−0.0028 (9)	0.0124 (8)
C1A	0.0084 (9)	0.0236 (9)	0.0173 (9)	0.0015 (8)	−0.0002 (8)	0.0065 (8)
C2A	0.0134 (10)	0.0268 (10)	0.0220 (10)	−0.0025 (9)	−0.0005 (8)	0.0028 (8)
C3A	0.0555 (17)	0.0290 (11)	0.0282 (12)	0.0031 (12)	0.0063 (12)	−0.0007 (9)
C4A	0.090 (2)	0.0353 (13)	0.0327 (13)	0.0065 (16)	0.0038 (16)	−0.0068 (11)
C5A	0.0430 (15)	0.0226 (10)	0.0317 (12)	−0.0005 (11)	−0.0041 (11)	0.0064 (9)
C6A	0.0132 (10)	0.0171 (9)	0.0186 (9)	0.0018 (8)	0.0014 (8)	0.0046 (8)
C8A	0.0176 (10)	0.0190 (9)	0.0245 (10)	−0.0006 (9)	−0.0003 (9)	0.0017 (8)
C9A	0.0190 (11)	0.0170 (9)	0.0382 (12)	0.0000 (9)	−0.0023 (10)	0.0010 (9)
C7A	0.0110 (9)	0.0184 (9)	0.0182 (9)	0.0014 (8)	0.0013 (8)	0.0020 (8)
C10A	0.0146 (10)	0.0180 (9)	0.0218 (10)	−0.0030 (9)	0.0037 (9)	0.0039 (8)
O3A	0.0298 (11)	0.0141 (7)	0.0238 (9)	0.0011 (8)	0.0044 (8)	0.0024 (7)
O4A	0.0174 (8)	0.0254 (7)	0.0170 (7)	−0.0024 (7)	−0.0003 (6)	0.0032 (6)
C71A	0.0110 (9)	0.0184 (9)	0.0182 (9)	0.0014 (8)	0.0013 (8)	0.0020 (8)
C11A	0.0146 (10)	0.0180 (9)	0.0218 (10)	−0.0030 (9)	0.0037 (9)	0.0039 (8)
O41A	0.0174 (8)	0.0254 (7)	0.0170 (7)	−0.0024 (7)	−0.0003 (6)	0.0032 (6)
O1B	0.0134 (7)	0.0254 (7)	0.0217 (7)	−0.0001 (6)	−0.0025 (6)	−0.0037 (6)
O2B	0.0136 (7)	0.0211 (7)	0.0298 (8)	0.0019 (6)	−0.0023 (6)	−0.0030 (6)
O3B	0.0181 (7)	0.0216 (6)	0.0228 (7)	−0.0042 (7)	−0.0001 (6)	0.0020 (6)
O4B	0.0192 (7)	0.0411 (8)	0.0173 (7)	−0.0005 (7)	−0.0018 (6)	0.0045 (6)
N1B	0.0143 (8)	0.0177 (7)	0.0212 (8)	−0.0019 (7)	0.0043 (7)	−0.0021 (7)
N2B	0.0088 (8)	0.0202 (7)	0.0167 (8)	0.0024 (7)	−0.0021 (7)	−0.0037 (6)
N3B	0.0167 (9)	0.0275 (9)	0.0257 (9)	0.0071 (8)	−0.0027 (8)	−0.0091 (7)
C1B	0.0110 (9)	0.0230 (9)	0.0155 (9)	−0.0001 (8)	−0.0013 (8)	−0.0029 (7)
C2B	0.0192 (10)	0.0194 (9)	0.0240 (10)	−0.0043 (9)	0.0004 (9)	−0.0026 (8)
C3B	0.0388 (15)	0.0213 (11)	0.0481 (15)	−0.0021 (11)	0.0132 (13)	−0.0054 (10)
C4B	0.063 (2)	0.0249 (12)	0.0675 (19)	−0.0033 (14)	0.0103 (17)	−0.0119 (12)
C5B	0.0488 (16)	0.0272 (11)	0.0275 (11)	−0.0009 (12)	0.0049 (12)	0.0057 (9)
C6B	0.0136 (10)	0.0154 (9)	0.0187 (9)	−0.0035 (8)	0.0036 (8)	0.0004 (8)
C7B	0.0096 (9)	0.0171 (9)	0.0154 (9)	−0.0003 (8)	0.0019 (8)	−0.0015 (7)
C8B	0.0150 (10)	0.0173 (9)	0.0206 (10)	−0.0008 (8)	0.0018 (9)	−0.0032 (7)
C9B	0.0142 (10)	0.0156 (9)	0.0184 (9)	−0.0016 (8)	0.0023 (8)	−0.0007 (7)
C10B	0.0130 (10)	0.0150 (8)	0.0193 (10)	0.0052 (8)	0.0006 (8)	−0.0009 (8)
O1W	0.0431 (13)	0.0392 (11)	0.0503 (13)	−0.0054 (12)	0.0148 (12)	−0.0166 (10)
O2W	0.0348 (10)	0.0475 (10)	0.0522 (11)	−0.0107 (9)	−0.0046 (9)	0.0118 (9)

Geometric parameters (Å, º)

O1A—C6A	1.230 (3)	N1B—C1B	1.498 (2)
O2A—C9A	1.226 (3)	N1B—H1B	0.9100
N1A—C1A	1.489 (2)	N1B—H2B	0.9100
N1A—H1A	0.9100	N1B—H3B	0.9100
N1A—H2A	0.9100	N2B—C6B	1.341 (2)
N1A—H3A	0.9100	N2B—C7B	1.465 (2)
N2A—C6A	1.331 (3)	N2B—H4B	0.8800
N2A—C7A	1.452 (2)	N3B—C9B	1.325 (3)
N2A—H4A	0.8800	N3B—H5B	0.8800
N3A—C9A	1.324 (3)	N3B—H6B	0.8800
N3A—H5A	0.8800	C1B—C6B	1.519 (3)
N3A—H6A	0.8800	C1B—C2B	1.543 (3)
C1A—C6A	1.530 (3)	C1B—H11B	1.0000
C1A—C2A	1.539 (3)	C2B—C3B	1.529 (3)
C1A—H11A	1.0000	C2B—C5B	1.529 (3)
C2A—C5A	1.529 (3)	C2B—H21B	1.0000
C2A—C3A	1.531 (3)	C3B—C4B	1.522 (3)
C2A—H21A	1.0000	C3B—H31B	0.9900
C3A—C4A	1.525 (3)	C3B—H32B	0.9900
C3A—H31A	0.9900	C4B—H41B	0.9800
C3A—H32A	0.9900	C4B—H42B	0.9800
C4A—H41A	0.9800	C4B—H43B	0.9800
C4A—H42A	0.9800	C5B—H51B	0.9800
C4A—H43A	0.9800	C5B—H52B	0.9800
C5A—H51A	0.9800	C5B—H53B	0.9800
C5A—H52A	0.9800	C7B—C8B	1.523 (3)
C5A—H53A	0.9800	C7B—C10B	1.545 (3)
C8A—C9A	1.509 (3)	C7B—H71B	1.0000
C8A—C7A	1.531 (3)	C8B—C9B	1.503 (3)
C8A—H81A	0.9900	C8B—H81B	0.9900
C8A—H82A	0.9900	C8B—H82B	0.9900
C7A—C10A	1.542 (3)	O1W—H11W	0.852 (9)
C7A—H71A	1.0000	O1W—H12W	0.860 (9)
C10A—O4A	1.258 (2)	O2W—H21W	0.853 (9)
C10A—O3A	1.262 (2)	O2W—H22W	0.850 (8)
C11A—O41A	1.259 (3)	O2W—H23W	0.852 (10)
C11A—O31A	1.262 (3)	O3W—H31W	0.855 (9)
O1B—C6B	1.235 (2)	O3W—H32W	0.854 (9)
O2B—C9B	1.243 (3)	O4W—H41W	0.850 (10)
O3B—C10B	1.259 (2)	O4W—H42W	0.858 (9)
O4B—C10B	1.253 (2)
C1A—N1A—H1A	109.5	H1B—N1B—H2B	109.5
C1A—N1A—H2A	109.5	C1B—N1B—H3B	109.5
H1A—N1A—H2A	109.5	H1B—N1B—H3B	109.5
C1A—N1A—H3A	109.5	H2B—N1B—H3B	109.5
H1A—N1A—H3A	109.5	C6B—N2B—C7B	122.67 (17)
H2A—N1A—H3A	109.5	C6B—N2B—H4B	118.7
C6A—N2A—C7A	123.27 (17)	C7B—N2B—H4B	118.7
C6A—N2A—H4A	118.4	C9B—N3B—H5B	120.0
C7A—N2A—H4A	118.4	C9B—N3B—H6B	120.0
C9A—N3A—H5A	120.0	H5B—N3B—H6B	120.0
C9A—N3A—H6A	120.0	N1B—C1B—C6B	106.09 (15)
H5A—N3A—H6A	120.0	N1B—C1B—C2B	110.47 (15)
N1A—C1A—C6A	107.05 (15)	C6B—C1B—C2B	111.23 (16)
N1A—C1A—C2A	112.11 (15)	N1B—C1B—H11B	109.7
C6A—C1A—C2A	110.10 (16)	C6B—C1B—H11B	109.7
N1A—C1A—H11A	109.2	C2B—C1B—H11B	109.7
C6A—C1A—H11A	109.2	C3B—C2B—C5B	111.85 (18)
C2A—C1A—H11A	109.2	C3B—C2B—C1B	111.24 (18)
C5A—C2A—C3A	110.87 (19)	C5B—C2B—C1B	109.79 (16)
C5A—C2A—C1A	108.70 (16)	C3B—C2B—H21B	107.9
C3A—C2A—C1A	112.57 (17)	C5B—C2B—H21B	107.9
C5A—C2A—H21A	108.2	C1B—C2B—H21B	107.9
C3A—C2A—H21A	108.2	C4B—C3B—C2B	114.3 (2)
C1A—C2A—H21A	108.2	C4B—C3B—H31B	108.7
C4A—C3A—C2A	113.4 (2)	C2B—C3B—H31B	108.7
C4A—C3A—H31A	108.9	C4B—C3B—H32B	108.7
C2A—C3A—H31A	108.9	C2B—C3B—H32B	108.7
C4A—C3A—H32A	108.9	H31B—C3B—H32B	107.6
C2A—C3A—H32A	108.9	C3B—C4B—H41B	109.5
H31A—C3A—H32A	107.7	C3B—C4B—H42B	109.5
C3A—C4A—H41A	109.5	H41B—C4B—H42B	109.5
C3A—C4A—H42A	109.5	C3B—C4B—H43B	109.5
H41A—C4A—H42A	109.5	H41B—C4B—H43B	109.5
C3A—C4A—H43A	109.5	H42B—C4B—H43B	109.5
H41A—C4A—H43A	109.5	C2B—C5B—H51B	109.5
H42A—C4A—H43A	109.5	C2B—C5B—H52B	109.5
C2A—C5A—H51A	109.5	H51B—C5B—H52B	109.5
C2A—C5A—H52A	109.5	C2B—C5B—H53B	109.5
H51A—C5A—H52A	109.5	H51B—C5B—H53B	109.5
C2A—C5A—H53A	109.5	H52B—C5B—H53B	109.5
H51A—C5A—H53A	109.5	O1B—C6B—N2B	124.60 (18)
H52A—C5A—H53A	109.5	O1B—C6B—C1B	120.22 (17)
O1A—C6A—N2A	124.98 (18)	N2B—C6B—C1B	115.17 (17)
O1A—C6A—C1A	118.79 (18)	N2B—C7B—C8B	108.53 (16)
N2A—C6A—C1A	116.22 (17)	N2B—C7B—C10B	107.86 (14)
C9A—C8A—C7A	110.40 (16)	C8B—C7B—C10B	113.31 (16)
C9A—C8A—H81A	109.6	N2B—C7B—H71B	109.0
C7A—C8A—H81A	109.6	C8B—C7B—H71B	109.0
C9A—C8A—H82A	109.6	C10B—C7B—H71B	109.0
C7A—C8A—H82A	109.6	C9B—C8B—C7B	113.37 (17)
H81A—C8A—H82A	108.1	C9B—C8B—H81B	108.9
O2A—C9A—N3A	122.8 (2)	C7B—C8B—H81B	108.9
O2A—C9A—C8A	120.1 (2)	C9B—C8B—H82B	108.9
N3A—C9A—C8A	117.11 (19)	C7B—C8B—H82B	108.9
N2A—C7A—C8A	110.72 (15)	H81B—C8B—H82B	107.7
N2A—C7A—C10A	112.36 (15)	O2B—C9B—N3B	122.31 (18)
C8A—C7A—C10A	112.22 (16)	O2B—C9B—C8B	121.73 (18)
N2A—C7A—H71A	107.1	N3B—C9B—C8B	115.95 (18)
C8A—C7A—H71A	107.1	O4B—C10B—O3B	124.80 (18)
C10A—C7A—H71A	107.1	O4B—C10B—C7B	117.97 (18)
O4A—C10A—O3A	125.37 (17)	O3B—C10B—C7B	117.23 (17)
O4A—C10A—C7A	116.22 (16)	H11W—O1W—H12W	105.9 (19)
O3A—C10A—C7A	118.39 (16)	H22W—O2W—H21W	105.9 (15)
O41A—C11A—O31A	125.2 (3)	H22W—O2W—H23W	105.0 (19)
C1B—N1B—H1B	109.5	H31W—O3W—H32W	104 (2)
C1B—N1B—H2B	109.5	H41W—O4W—H42W	105 (2)
N1A—C1A—C6A—N2A	126.30 (18)	C5A—C2A—C3A—C4A	−62.0 (3)
C1A—C6A—N2A—C7A	176.95 (15)	C7A—N2A—C6A—O1A	−2.2 (3)
C6A—N2A—C7A—C10A	−110.5 (2)	N1A—C1A—C6A—O1A	−54.5 (2)
N2A—C7A—C10A—O3A	12.1 (3)	C2A—C1A—C6A—O1A	67.6 (2)
C6A—N2A—C7A—C11A	−115.5 (3)	C2A—C1A—C6A—N2A	−111.60 (19)
N2A—C7A—C11A—O31A	−10.2 (6)	C6A—N2A—C7A—C8A	123.10 (19)
N1A—C1A—C2A—C3A	−55.2 (2)	C6A—N2A—C7A—C10A	−110.5 (2)
N1A—C1A—C2A—C5A	−178.44 (17)	C9A—C8A—C7A—C10A	169.92 (18)
C1A—C2A—C3A—C4A	176.0 (2)	N2A—C7A—C10A—O4A	−169.5 (2)
N2A—C7A—C8A—C9A	−63.7 (2)	C8A—C7A—C10A—O4A	−44.0 (3)
C7A—C8A—C9A—O2A	−51.6 (3)	C8A—C7A—C10A—O3A	137.6 (2)
C7A—C8A—C9A—N3A	128.7 (2)	C6B—C1B—C2B—C3B	178.27 (18)
N1B—C1B—C6B—N2B	130.70 (17)	C6B—C1B—C2B—C5B	53.9 (2)
C1B—C6B—N2B—C7B	174.21 (15)	C5B—C2B—C3B—C4B	−68.2 (3)
C6B—N2B—C7B—C10B	−93.1 (2)	C7B—N2B—C6B—O1B	−4.9 (3)
N2B—C7B—C10B—O3B	75.8 (2)	N1B—C1B—C6B—O1B	−50.1 (2)
N1B—C1B—C2B—C3B	−64.2 (2)	C2B—C1B—C6B—O1B	70.0 (2)
N1B—C1B—C2B—C5B	171.47 (19)	C2B—C1B—C6B—N2B	−109.13 (19)
C1B—C2B—C3B—C4B	168.6 (2)	C6B—N2B—C7B—C8B	143.78 (17)
N2B—C7B—C8B—C9B	179.88 (15)	C10B—C7B—C8B—C9B	60.1 (2)
C7B—C8B—C9B—O2B	31.5 (3)	N2B—C7B—C10B—O4B	−103.91 (19)
C7B—C8B—C9B—N3B	−149.65 (17)	C8B—C7B—C10B—O4B	16.2 (2)
C6A—C1A—C2A—C5A	62.5 (2)	C8B—C7B—C10B—O3B	−164.00 (16)
C6A—C1A—C2A—C3A	−174.27 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1W	0.91	1.87	2.755 (3)	164
N1A—H1A···O3W	0.91	2.23	2.959 (8)	136
N1A—H2A···O3B	0.91	1.91	2.792 (2)	163
N1A—H3A···O4B^i	0.91	2.03	2.695 (2)	128
N2A—H4A···O1A^ii	0.88	1.99	2.862 (2)	169
N3A—H5A···O2W	0.88	2.35	3.146 (2)	151
N3A—H6A···O2A^ii	0.88	1.98	2.846 (3)	167
C1A—H11A···O1A^ii	1.00	2.41	3.298 (2)	147
C8A—H81A···O2A^ii	0.99	2.52	3.383 (3)	146
N1B—H1B···O2B^iii	0.91	1.85	2.758 (2)	174
N1B—H2B···O4A^iv	0.91	1.93	2.835 (2)	172
N1B—H3B···O4A^v	0.91	2.06	2.968 (2)	179
N2B—H4B···O3B^ii	0.88	2.12	2.928 (2)	152
N3B—H5B···O3A^vi	0.88	2.09	2.946 (2)	163
N3B—H6B···O2B^ii	0.88	2.32	3.046 (2)	139
C1B—H11B···O1B^ii	1.00	2.27	3.098 (2)	139
C8B—H82B···O3B^ii	0.99	2.54	3.341 (2)	137
O1W—H11W···O2W	0.85 (1)	1.95 (1)	2.785 (3)	168 (3)
O1W—H12W···O4B	0.86 (1)	2.08 (1)	2.804 (3)	141 (2)
O2W—H21W···O3A^vii	0.85 (1)	2.17 (1)	3.019 (3)	179 (2)
O2W—H22W···O3A^vi	0.85 (1)	2.07 (1)	2.903 (3)	167 (2)
O2W—H22W···O31A^vi	0.85 (1)	1.93 (1)	2.749 (4)	161 (2)
O2W—H23W···O4W	0.85 (1)	2.31 (2)	3.153 (12)	170 (4)
O3W—H31W···O2A	0.86 (1)	2.09 (1)	2.917 (8)	164 (4)
O3W—H32W···O2W	0.85 (1)	2.31 (1)	3.157 (8)	172 (4)
O4W—H41W···O4B	0.85 (1)	2.10 (2)	2.867 (10)	150 (4)
O4W—H42W···O3W	0.86 (1)	2.42 (1)	3.281 (12)	179 (6)

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