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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110020895/jz3182sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110020895/jz3182Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270110020895/jz3182sup3.pdf
Supplementary material

CCDC reference: 786813

Computing details top

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 top
Crystal data top
C10H19N3O4·1.094H2ODx = 1.287 Mg m3
Mr = 265.01Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 50.56 reflections
a = 4.7855 (4) Åθ = 1.3–28.3°
b = 18.2887 (15) ŵ = 0.10 mm1
c = 31.247 (3) ÅT = 105 K
V = 2734.8 (4) Å3Block, colourless
Z = 80.78 × 0.50 × 0.22 mm
F(000) = 1144
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3860 independent reflections
Radiation source: fine-focus sealed tube2902 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
Detector resolution: 8.3 pixels mm-1θmax = 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. scansh = 56
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
k = 2421
Tmin = 0.751, Tmax = 0.978l = 4041
18243 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0479P)2 + 0.6738P]
where P = (Fo2 + 2Fc2)/3
3860 reflections(Δ/σ)max = 0.001
376 parametersΔρmax = 0.22 e Å3
25 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. Crystallized from water and 2-propanol

Refinement. Refinement of F2 against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A1.2190 (3)0.45870 (9)0.26437 (5)0.0268 (4)
O2A1.1326 (4)0.29647 (9)0.20361 (7)0.0501 (6)
N1A0.9555 (4)0.41979 (9)0.34181 (5)0.0212 (4)
H1A0.91410.37370.33290.032*
H2A0.88320.42710.36840.032*
H3A1.14430.42560.34270.032*
N2A0.7851 (3)0.44876 (8)0.23547 (5)0.0155 (4)
H4A0.60500.44850.24110.019*
N3A0.7000 (4)0.25330 (9)0.21399 (6)0.0287 (5)
H5A0.76130.21520.22840.034*
H6A0.51960.25910.20970.034*
C1A0.8328 (4)0.47381 (10)0.31154 (6)0.0164 (4)
H11A0.62630.46590.30980.020*
C2A0.8904 (5)0.55316 (11)0.32538 (6)0.0208 (5)
H21A1.09680.56160.32420.025*
C3A0.7907 (7)0.56896 (12)0.37101 (7)0.0376 (7)
H31A0.58540.56260.37220.045*
H32A0.87560.53280.39070.045*
C4A0.8639 (8)0.64568 (14)0.38650 (8)0.0525 (9)
H41A0.82450.64960.41720.079*
H42A0.75150.68160.37090.079*
H43A1.06270.65510.38140.079*
C5A0.7509 (6)0.60483 (11)0.29337 (7)0.0324 (6)
H51A0.79660.65550.30080.049*
H52A0.54790.59800.29440.049*
H53A0.81890.59400.26450.049*
C6A0.9630 (4)0.45919 (10)0.26765 (6)0.0163 (4)
C8A0.7595 (5)0.36546 (10)0.17401 (6)0.0204 (5)
H81A0.55330.36510.17640.024*
H82A0.80920.36070.14340.024*
C9A0.8793 (5)0.30183 (11)0.19866 (7)0.0247 (5)
C7A0.8735 (4)0.43776 (10)0.19150 (6)0.0159 (4)0.812 (2)
H71A1.08190.43370.19170.019*0.812 (2)
C10A0.7989 (5)0.50320 (10)0.16254 (6)0.0181 (5)0.812 (2)
O3A0.7196 (4)0.56185 (7)0.18000 (5)0.0226 (4)0.812 (2)
O4A0.8293 (4)0.49360 (9)0.12294 (4)0.0199 (4)0.812 (2)
C71A0.8735 (4)0.43776 (10)0.19150 (6)0.0159 (4)0.188 (2)
H72A1.08220.43530.19100.019*0.188 (2)
C11A0.7808 (11)0.4991 (2)0.16068 (10)0.0181 (5)0.188 (2)
O31A0.6080 (9)0.5460 (2)0.17402 (14)0.030*0.188 (2)
O41A0.8709 (14)0.4947 (3)0.12293 (9)0.0199 (4)0.188 (2)
O1B0.5777 (3)0.39876 (7)0.52851 (4)0.0202 (3)
O2B0.5780 (3)0.19722 (7)0.41309 (5)0.0215 (3)
O3B0.7463 (3)0.41106 (7)0.42507 (4)0.0208 (3)
O4B0.4277 (3)0.37045 (8)0.37892 (4)0.0259 (4)
N1B0.1538 (4)0.45197 (8)0.58124 (5)0.0178 (4)
H1B0.14000.40260.58430.027*
H2B0.00330.47380.59360.027*
H3B0.31300.46800.59410.027*
N2B0.2361 (3)0.38184 (8)0.47855 (5)0.0152 (4)
H4B0.06340.39270.47130.018*
N3B0.1701 (4)0.18564 (9)0.37793 (5)0.0233 (4)
H5B0.23870.15180.36090.028*
H6B0.00470.19980.37510.028*
C1B0.1623 (4)0.47080 (10)0.53461 (6)0.0165 (4)
H11B0.03060.46840.52240.020*
C2B0.2835 (5)0.54817 (10)0.52808 (6)0.0209 (5)
H21B0.46880.55030.54280.025*
C3B0.0949 (6)0.60635 (11)0.54807 (8)0.0361 (7)
H31B0.07920.60970.53110.043*
H32B0.04310.59050.57730.043*
C4B0.2264 (7)0.68202 (13)0.55069 (10)0.0517 (8)
H41B0.39750.67960.56780.078*
H42B0.09450.71600.56410.078*
H43B0.27170.69920.52180.078*
C5B0.3320 (6)0.56207 (12)0.48041 (7)0.0345 (6)
H51B0.46830.52680.46940.052*
H52B0.40360.61180.47640.052*
H53B0.15530.55660.46490.052*
C6B0.3452 (4)0.41319 (10)0.51357 (6)0.0159 (4)
C7B0.3928 (4)0.33022 (10)0.45191 (6)0.0140 (4)
H71B0.54090.30650.46970.017*
C8B0.1922 (4)0.27172 (10)0.43579 (6)0.0176 (5)
H81B0.10650.24690.46070.021*
H82B0.04040.29560.41940.021*
C9B0.3301 (4)0.21541 (10)0.40785 (6)0.0161 (4)
C10B0.5334 (4)0.37404 (10)0.41555 (6)0.0158 (4)
O1W0.7319 (5)0.28591 (11)0.32034 (7)0.0442 (6)0.812 (2)
H11W0.718 (6)0.2417 (5)0.3121 (8)0.066*0.812 (2)
H12W0.587 (3)0.2942 (11)0.3360 (6)0.066*0.812 (2)
O2W0.7654 (4)0.14272 (9)0.29047 (6)0.0448 (5)
H22W0.630 (2)0.1143 (7)0.2960 (9)0.067*
H21W0.912 (2)0.1204 (12)0.2988 (10)0.067*0.812 (2)
H23W0.699 (6)0.1857 (6)0.293 (3)0.067*0.188 (2)
O3W1.1345 (19)0.2854 (4)0.2968 (2)0.042 (2)*0.188 (2)
H31W1.164 (9)0.293 (2)0.2702 (3)0.064*0.188 (2)
H32W1.044 (5)0.2453 (9)0.2971 (14)0.064*0.188 (2)
O4W0.4496 (18)0.2933 (7)0.2991 (3)0.077 (4)*0.188 (2)
H41W0.412 (6)0.301 (2)0.3253 (5)0.116*0.188 (2)
H42W0.629 (2)0.291 (9)0.2981 (15)0.116*0.188 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0074 (7)0.0504 (9)0.0227 (7)0.0015 (7)0.0009 (6)0.0002 (7)
O2A0.0154 (8)0.0245 (8)0.1103 (17)0.0016 (7)0.0026 (10)0.0180 (9)
N1A0.0164 (9)0.0282 (9)0.0191 (8)0.0036 (8)0.0007 (7)0.0041 (7)
N2A0.0080 (8)0.0207 (8)0.0177 (7)0.0003 (7)0.0023 (7)0.0041 (6)
N3A0.0156 (9)0.0228 (8)0.0478 (11)0.0000 (8)0.0028 (9)0.0124 (8)
C1A0.0084 (9)0.0236 (9)0.0173 (9)0.0015 (8)0.0002 (8)0.0065 (8)
C2A0.0134 (10)0.0268 (10)0.0220 (10)0.0025 (9)0.0005 (8)0.0028 (8)
C3A0.0555 (17)0.0290 (11)0.0282 (12)0.0031 (12)0.0063 (12)0.0007 (9)
C4A0.090 (2)0.0353 (13)0.0327 (13)0.0065 (16)0.0038 (16)0.0068 (11)
C5A0.0430 (15)0.0226 (10)0.0317 (12)0.0005 (11)0.0041 (11)0.0064 (9)
C6A0.0132 (10)0.0171 (9)0.0186 (9)0.0018 (8)0.0014 (8)0.0046 (8)
C8A0.0176 (10)0.0190 (9)0.0245 (10)0.0006 (9)0.0003 (9)0.0017 (8)
C9A0.0190 (11)0.0170 (9)0.0382 (12)0.0000 (9)0.0023 (10)0.0010 (9)
C7A0.0110 (9)0.0184 (9)0.0182 (9)0.0014 (8)0.0013 (8)0.0020 (8)
C10A0.0146 (10)0.0180 (9)0.0218 (10)0.0030 (9)0.0037 (9)0.0039 (8)
O3A0.0298 (11)0.0141 (7)0.0238 (9)0.0011 (8)0.0044 (8)0.0024 (7)
O4A0.0174 (8)0.0254 (7)0.0170 (7)0.0024 (7)0.0003 (6)0.0032 (6)
C71A0.0110 (9)0.0184 (9)0.0182 (9)0.0014 (8)0.0013 (8)0.0020 (8)
C11A0.0146 (10)0.0180 (9)0.0218 (10)0.0030 (9)0.0037 (9)0.0039 (8)
O41A0.0174 (8)0.0254 (7)0.0170 (7)0.0024 (7)0.0003 (6)0.0032 (6)
O1B0.0134 (7)0.0254 (7)0.0217 (7)0.0001 (6)0.0025 (6)0.0037 (6)
O2B0.0136 (7)0.0211 (7)0.0298 (8)0.0019 (6)0.0023 (6)0.0030 (6)
O3B0.0181 (7)0.0216 (6)0.0228 (7)0.0042 (7)0.0001 (6)0.0020 (6)
O4B0.0192 (7)0.0411 (8)0.0173 (7)0.0005 (7)0.0018 (6)0.0045 (6)
N1B0.0143 (8)0.0177 (7)0.0212 (8)0.0019 (7)0.0043 (7)0.0021 (7)
N2B0.0088 (8)0.0202 (7)0.0167 (8)0.0024 (7)0.0021 (7)0.0037 (6)
N3B0.0167 (9)0.0275 (9)0.0257 (9)0.0071 (8)0.0027 (8)0.0091 (7)
C1B0.0110 (9)0.0230 (9)0.0155 (9)0.0001 (8)0.0013 (8)0.0029 (7)
C2B0.0192 (10)0.0194 (9)0.0240 (10)0.0043 (9)0.0004 (9)0.0026 (8)
C3B0.0388 (15)0.0213 (11)0.0481 (15)0.0021 (11)0.0132 (13)0.0054 (10)
C4B0.063 (2)0.0249 (12)0.0675 (19)0.0033 (14)0.0103 (17)0.0119 (12)
C5B0.0488 (16)0.0272 (11)0.0275 (11)0.0009 (12)0.0049 (12)0.0057 (9)
C6B0.0136 (10)0.0154 (9)0.0187 (9)0.0035 (8)0.0036 (8)0.0004 (8)
C7B0.0096 (9)0.0171 (9)0.0154 (9)0.0003 (8)0.0019 (8)0.0015 (7)
C8B0.0150 (10)0.0173 (9)0.0206 (10)0.0008 (8)0.0018 (9)0.0032 (7)
C9B0.0142 (10)0.0156 (9)0.0184 (9)0.0016 (8)0.0023 (8)0.0007 (7)
C10B0.0130 (10)0.0150 (8)0.0193 (10)0.0052 (8)0.0006 (8)0.0009 (8)
O1W0.0431 (13)0.0392 (11)0.0503 (13)0.0054 (12)0.0148 (12)0.0166 (10)
O2W0.0348 (10)0.0475 (10)0.0522 (11)0.0107 (9)0.0046 (9)0.0118 (9)
Geometric parameters (Å, º) top
O1A—C6A1.230 (3)N1B—C1B1.498 (2)
O2A—C9A1.226 (3)N1B—H1B0.9100
N1A—C1A1.489 (2)N1B—H2B0.9100
N1A—H1A0.9100N1B—H3B0.9100
N1A—H2A0.9100N2B—C6B1.341 (2)
N1A—H3A0.9100N2B—C7B1.465 (2)
N2A—C6A1.331 (3)N2B—H4B0.8800
N2A—C7A1.452 (2)N3B—C9B1.325 (3)
N2A—H4A0.8800N3B—H5B0.8800
N3A—C9A1.324 (3)N3B—H6B0.8800
N3A—H5A0.8800C1B—C6B1.519 (3)
N3A—H6A0.8800C1B—C2B1.543 (3)
C1A—C6A1.530 (3)C1B—H11B1.0000
C1A—C2A1.539 (3)C2B—C3B1.529 (3)
C1A—H11A1.0000C2B—C5B1.529 (3)
C2A—C5A1.529 (3)C2B—H21B1.0000
C2A—C3A1.531 (3)C3B—C4B1.522 (3)
C2A—H21A1.0000C3B—H31B0.9900
C3A—C4A1.525 (3)C3B—H32B0.9900
C3A—H31A0.9900C4B—H41B0.9800
C3A—H32A0.9900C4B—H42B0.9800
C4A—H41A0.9800C4B—H43B0.9800
C4A—H42A0.9800C5B—H51B0.9800
C4A—H43A0.9800C5B—H52B0.9800
C5A—H51A0.9800C5B—H53B0.9800
C5A—H52A0.9800C7B—C8B1.523 (3)
C5A—H53A0.9800C7B—C10B1.545 (3)
C8A—C9A1.509 (3)C7B—H71B1.0000
C8A—C7A1.531 (3)C8B—C9B1.503 (3)
C8A—H81A0.9900C8B—H81B0.9900
C8A—H82A0.9900C8B—H82B0.9900
C7A—C10A1.542 (3)O1W—H11W0.852 (9)
C7A—H71A1.0000O1W—H12W0.860 (9)
C10A—O4A1.258 (2)O2W—H21W0.853 (9)
C10A—O3A1.262 (2)O2W—H22W0.850 (8)
C11A—O41A1.259 (3)O2W—H23W0.852 (10)
C11A—O31A1.262 (3)O3W—H31W0.855 (9)
O1B—C6B1.235 (2)O3W—H32W0.854 (9)
O2B—C9B1.243 (3)O4W—H41W0.850 (10)
O3B—C10B1.259 (2)O4W—H42W0.858 (9)
O4B—C10B1.253 (2)
C1A—N1A—H1A109.5H1B—N1B—H2B109.5
C1A—N1A—H2A109.5C1B—N1B—H3B109.5
H1A—N1A—H2A109.5H1B—N1B—H3B109.5
C1A—N1A—H3A109.5H2B—N1B—H3B109.5
H1A—N1A—H3A109.5C6B—N2B—C7B122.67 (17)
H2A—N1A—H3A109.5C6B—N2B—H4B118.7
C6A—N2A—C7A123.27 (17)C7B—N2B—H4B118.7
C6A—N2A—H4A118.4C9B—N3B—H5B120.0
C7A—N2A—H4A118.4C9B—N3B—H6B120.0
C9A—N3A—H5A120.0H5B—N3B—H6B120.0
C9A—N3A—H6A120.0N1B—C1B—C6B106.09 (15)
H5A—N3A—H6A120.0N1B—C1B—C2B110.47 (15)
N1A—C1A—C6A107.05 (15)C6B—C1B—C2B111.23 (16)
N1A—C1A—C2A112.11 (15)N1B—C1B—H11B109.7
C6A—C1A—C2A110.10 (16)C6B—C1B—H11B109.7
N1A—C1A—H11A109.2C2B—C1B—H11B109.7
C6A—C1A—H11A109.2C3B—C2B—C5B111.85 (18)
C2A—C1A—H11A109.2C3B—C2B—C1B111.24 (18)
C5A—C2A—C3A110.87 (19)C5B—C2B—C1B109.79 (16)
C5A—C2A—C1A108.70 (16)C3B—C2B—H21B107.9
C3A—C2A—C1A112.57 (17)C5B—C2B—H21B107.9
C5A—C2A—H21A108.2C1B—C2B—H21B107.9
C3A—C2A—H21A108.2C4B—C3B—C2B114.3 (2)
C1A—C2A—H21A108.2C4B—C3B—H31B108.7
C4A—C3A—C2A113.4 (2)C2B—C3B—H31B108.7
C4A—C3A—H31A108.9C4B—C3B—H32B108.7
C2A—C3A—H31A108.9C2B—C3B—H32B108.7
C4A—C3A—H32A108.9H31B—C3B—H32B107.6
C2A—C3A—H32A108.9C3B—C4B—H41B109.5
H31A—C3A—H32A107.7C3B—C4B—H42B109.5
C3A—C4A—H41A109.5H41B—C4B—H42B109.5
C3A—C4A—H42A109.5C3B—C4B—H43B109.5
H41A—C4A—H42A109.5H41B—C4B—H43B109.5
C3A—C4A—H43A109.5H42B—C4B—H43B109.5
H41A—C4A—H43A109.5C2B—C5B—H51B109.5
H42A—C4A—H43A109.5C2B—C5B—H52B109.5
C2A—C5A—H51A109.5H51B—C5B—H52B109.5
C2A—C5A—H52A109.5C2B—C5B—H53B109.5
H51A—C5A—H52A109.5H51B—C5B—H53B109.5
C2A—C5A—H53A109.5H52B—C5B—H53B109.5
H51A—C5A—H53A109.5O1B—C6B—N2B124.60 (18)
H52A—C5A—H53A109.5O1B—C6B—C1B120.22 (17)
O1A—C6A—N2A124.98 (18)N2B—C6B—C1B115.17 (17)
O1A—C6A—C1A118.79 (18)N2B—C7B—C8B108.53 (16)
N2A—C6A—C1A116.22 (17)N2B—C7B—C10B107.86 (14)
C9A—C8A—C7A110.40 (16)C8B—C7B—C10B113.31 (16)
C9A—C8A—H81A109.6N2B—C7B—H71B109.0
C7A—C8A—H81A109.6C8B—C7B—H71B109.0
C9A—C8A—H82A109.6C10B—C7B—H71B109.0
C7A—C8A—H82A109.6C9B—C8B—C7B113.37 (17)
H81A—C8A—H82A108.1C9B—C8B—H81B108.9
O2A—C9A—N3A122.8 (2)C7B—C8B—H81B108.9
O2A—C9A—C8A120.1 (2)C9B—C8B—H82B108.9
N3A—C9A—C8A117.11 (19)C7B—C8B—H82B108.9
N2A—C7A—C8A110.72 (15)H81B—C8B—H82B107.7
N2A—C7A—C10A112.36 (15)O2B—C9B—N3B122.31 (18)
C8A—C7A—C10A112.22 (16)O2B—C9B—C8B121.73 (18)
N2A—C7A—H71A107.1N3B—C9B—C8B115.95 (18)
C8A—C7A—H71A107.1O4B—C10B—O3B124.80 (18)
C10A—C7A—H71A107.1O4B—C10B—C7B117.97 (18)
O4A—C10A—O3A125.37 (17)O3B—C10B—C7B117.23 (17)
O4A—C10A—C7A116.22 (16)H11W—O1W—H12W105.9 (19)
O3A—C10A—C7A118.39 (16)H22W—O2W—H21W105.9 (15)
O41A—C11A—O31A125.2 (3)H22W—O2W—H23W105.0 (19)
C1B—N1B—H1B109.5H31W—O3W—H32W104 (2)
C1B—N1B—H2B109.5H41W—O4W—H42W105 (2)
N1A—C1A—C6A—N2A126.30 (18)C5A—C2A—C3A—C4A62.0 (3)
C1A—C6A—N2A—C7A176.95 (15)C7A—N2A—C6A—O1A2.2 (3)
C6A—N2A—C7A—C10A110.5 (2)N1A—C1A—C6A—O1A54.5 (2)
N2A—C7A—C10A—O3A12.1 (3)C2A—C1A—C6A—O1A67.6 (2)
C6A—N2A—C7A—C11A115.5 (3)C2A—C1A—C6A—N2A111.60 (19)
N2A—C7A—C11A—O31A10.2 (6)C6A—N2A—C7A—C8A123.10 (19)
N1A—C1A—C2A—C3A55.2 (2)C6A—N2A—C7A—C10A110.5 (2)
N1A—C1A—C2A—C5A178.44 (17)C9A—C8A—C7A—C10A169.92 (18)
C1A—C2A—C3A—C4A176.0 (2)N2A—C7A—C10A—O4A169.5 (2)
N2A—C7A—C8A—C9A63.7 (2)C8A—C7A—C10A—O4A44.0 (3)
C7A—C8A—C9A—O2A51.6 (3)C8A—C7A—C10A—O3A137.6 (2)
C7A—C8A—C9A—N3A128.7 (2)C6B—C1B—C2B—C3B178.27 (18)
N1B—C1B—C6B—N2B130.70 (17)C6B—C1B—C2B—C5B53.9 (2)
C1B—C6B—N2B—C7B174.21 (15)C5B—C2B—C3B—C4B68.2 (3)
C6B—N2B—C7B—C10B93.1 (2)C7B—N2B—C6B—O1B4.9 (3)
N2B—C7B—C10B—O3B75.8 (2)N1B—C1B—C6B—O1B50.1 (2)
N1B—C1B—C2B—C3B64.2 (2)C2B—C1B—C6B—O1B70.0 (2)
N1B—C1B—C2B—C5B171.47 (19)C2B—C1B—C6B—N2B109.13 (19)
C1B—C2B—C3B—C4B168.6 (2)C6B—N2B—C7B—C8B143.78 (17)
N2B—C7B—C8B—C9B179.88 (15)C10B—C7B—C8B—C9B60.1 (2)
C7B—C8B—C9B—O2B31.5 (3)N2B—C7B—C10B—O4B103.91 (19)
C7B—C8B—C9B—N3B149.65 (17)C8B—C7B—C10B—O4B16.2 (2)
C6A—C1A—C2A—C5A62.5 (2)C8B—C7B—C10B—O3B164.00 (16)
C6A—C1A—C2A—C3A174.27 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1W0.911.872.755 (3)164
N1A—H1A···O3W0.912.232.959 (8)136
N1A—H2A···O3B0.911.912.792 (2)163
N1A—H3A···O4Bi0.912.032.695 (2)128
N2A—H4A···O1Aii0.881.992.862 (2)169
N3A—H5A···O2W0.882.353.146 (2)151
N3A—H6A···O2Aii0.881.982.846 (3)167
C1A—H11A···O1Aii1.002.413.298 (2)147
C8A—H81A···O2Aii0.992.523.383 (3)146
N1B—H1B···O2Biii0.911.852.758 (2)174
N1B—H2B···O4Aiv0.911.932.835 (2)172
N1B—H3B···O4Av0.912.062.968 (2)179
N2B—H4B···O3Bii0.882.122.928 (2)152
N3B—H5B···O3Avi0.882.092.946 (2)163
N3B—H6B···O2Bii0.882.323.046 (2)139
C1B—H11B···O1Bii1.002.273.098 (2)139
C8B—H82B···O3Bii0.992.543.341 (2)137
O1W—H11W···O2W0.85 (1)1.95 (1)2.785 (3)168 (3)
O1W—H12W···O4B0.86 (1)2.08 (1)2.804 (3)141 (2)
O2W—H21W···O3Avii0.85 (1)2.17 (1)3.019 (3)179 (2)
O2W—H22W···O3Avi0.85 (1)2.07 (1)2.903 (3)167 (2)
O2W—H22W···O31Avi0.85 (1)1.93 (1)2.749 (4)161 (2)
O2W—H23W···O4W0.85 (1)2.31 (2)3.153 (12)170 (4)
O3W—H31W···O2A0.86 (1)2.09 (1)2.917 (8)164 (4)
O3W—H32W···O2W0.85 (1)2.31 (1)3.157 (8)172 (4)
O4W—H41W···O4B0.85 (1)2.10 (2)2.867 (10)150 (4)
O4W—H42W···O3W0.86 (1)2.42 (1)3.281 (12)179 (6)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x1/2, 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, y1/2, z+1/2; (vii) x+2, y1/2, z+1/2.
Selected torsion angles (°) for molecules A and B top
Molecule AMolecule B
N1—C1—C6—N2126.30 (18)130.70 (17)
C1—C6—N2—C7176.95 (15)174.21 (15)
C6—N2—C7—C10-110.5 (2)-93.1 (2)
N2—C7—C10—O312.1 (3)75.8 (2)
C6—N2—C7—C11-115.5 (3)
N2—C7—C11—O31-10.2 (6)
N1—C1—C2—C3-55.2 (2)-64.2 (2)
N1—C1—C2—C5-178.44 (17)171.47 (19)
C1—C2—C3—C4176.0 (2)168.6 (2)
N2—C7—C8—C9-63.7 (2)179.88 (15)
C7—C8—C9—O2-51.6 (3)31.5 (3)
C7—C8—C9—N3128.7 (2)-149.65 (17)
 

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