DL-Valinium nitrate

The asymmetric unit of the title compound, C₅H₁₂NO₂⁺·NO₃⁻, consists of four valinium cations and four nitrate anions. The valinium residues are related to one another by pseudo-twofold symmetry and pseudo-translation. The nitrate anions are related by a pseudo-c-glide and pseudo-translation. The crystal structure is stabilized by N—H...O and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.180
• Data-to-parameter ratio = 12.4

checkCIF results

No syntax errors found


 Alert Level B:



PLAT_112  Alert B ADDSYM Detects Additional (Pseudo) Symm. Elem.          Y


 Alert Level C:



THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5803


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

DL-valinium nitrate

Crystal data

C5H12NO2^+·NO3^−	Z = 8
Mr = 180.17	F(000) = 768
Triclinic, P1	Dx = 1.389 Mg m^−3 Dm = 1.375 Mg m^−3 Dm measured by flotation using mixture of carbon tetrachloride and xylene
a = 9.5695 (10) Å	Cu Kα radiation, λ = 1.54180 Å
b = 11.2104 (16) Å	Cell parameters from 25 reflections
c = 17.537 (3) Å	θ = 15.2–23.8°
α = 108.52 (3)°	µ = 1.08 mm^−1
β = 104.14 (2)°	T = 293 K
γ = 90.25 (2)°	Needle, colorless
V = 1722.9 (4) Å^3	0.45 × 0.3 × 0.15 mm

Data collection

Enraf-Nonius sealed tube diffractometer	4447 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.012
Graphite monochromator	θmax = 63.5°, θmin = 2.8°
ω–2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −12→11
Tmin = 0.712, Tmax = 0.851	l = −19→19
5768 measured reflections	3 standard reflections every 60 min
5409 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)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.180	w = 1/[σ^2(Fo^2) + (0.0809P)^2 + 1.5449P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
5409 reflections	Δρmax = 0.43 e Å^−3
435 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (4)

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.1736 (3)	0.6748 (3)	0.51090 (16)	0.0383 (6)
O1A	0.1612 (3)	0.6144 (3)	0.55649 (16)	0.0536 (7)
O1B	0.1719 (3)	0.6211 (2)	0.43638 (14)	0.0524 (7)
O1C	0.1884 (3)	0.7944 (2)	0.53753 (14)	0.0498 (6)
N2	0.1416 (3)	0.1749 (3)	0.50931 (16)	0.0397 (6)
O2A	0.1516 (3)	0.1128 (3)	0.55619 (17)	0.0629 (8)
O2B	0.1337 (3)	0.1246 (2)	0.43381 (15)	0.0554 (7)
O2C	0.1368 (3)	0.2936 (2)	0.53592 (14)	0.0489 (6)
N3	0.1704 (3)	0.3332 (3)	0.01105 (17)	0.0397 (6)
O3A	0.1595 (3)	0.4387 (2)	0.05717 (16)	0.0547 (7)
O3B	0.1713 (3)	0.3136 (2)	−0.06314 (15)	0.0569 (7)
O3C	0.1811 (3)	0.2391 (2)	0.03680 (14)	0.0482 (6)
N4	0.8549 (3)	0.1627 (3)	−0.00921 (16)	0.0382 (6)
O4A	0.8463 (3)	0.0542 (2)	−0.05549 (17)	0.0622 (8)
O4B	0.8636 (3)	0.1893 (2)	0.06651 (14)	0.0531 (7)
O4C	0.8580 (3)	0.2546 (2)	−0.03675 (14)	0.0507 (6)
O11	0.8927 (3)	1.1682 (2)	0.25717 (14)	0.0470 (6)
O12	0.7869 (3)	1.0479 (3)	0.31090 (14)	0.0619 (8)
H12	0.8094	1.1098	0.3533	0.093*
C11	0.8311 (3)	1.0710 (3)	0.25139 (18)	0.0359 (7)
C12	0.7917 (3)	0.9582 (3)	0.17196 (18)	0.0333 (7)
H12A	0.8145	0.8819	0.1866	0.040*
N11	0.8853 (3)	0.9727 (2)	0.11845 (15)	0.0344 (6)
H11A	0.8642	0.9077	0.0712	0.052*
H11B	0.9778	0.9749	0.1451	0.052*
H11C	0.8700	1.0442	0.1071	0.052*
C13	0.6305 (4)	0.9430 (3)	0.1256 (2)	0.0463 (8)
H13	0.6212	0.8848	0.0691	0.056*
C14	0.5402 (5)	0.8813 (5)	0.1654 (3)	0.0739 (13)
H14A	0.5795	0.8044	0.1700	0.111*
H14B	0.4423	0.8626	0.1315	0.111*
H14C	0.5417	0.9378	0.2198	0.111*
C15	0.5736 (5)	1.0651 (5)	0.1170 (3)	0.0711 (12)
H15A	0.6333	1.1015	0.0919	0.107*
H15B	0.5753	1.1230	0.1710	0.107*
H15C	0.4761	1.0482	0.0826	0.107*
O21	0.1042 (3)	0.9136 (2)	0.24535 (14)	0.0468 (6)
O22	0.2003 (3)	0.7362 (3)	0.18907 (14)	0.0593 (8)
H22	0.1754	0.7553	0.1466	0.089*
C21	0.1632 (3)	0.8214 (3)	0.25036 (18)	0.0351 (7)
C22	0.2082 (3)	0.7892 (3)	0.33035 (18)	0.0351 (7)
H22A	0.1868	0.6981	0.3167	0.042*
N21	0.1160 (3)	0.8569 (2)	0.38509 (15)	0.0349 (6)
H21A	0.1394	0.8401	0.4327	0.052*
H21B	0.0233	0.8312	0.3595	0.052*
H21C	0.1304	0.9397	0.3956	0.052*
C23	0.3694 (4)	0.8233 (4)	0.3754 (2)	0.0460 (8)
H23	0.3813	0.8205	0.4319	0.055*
C24	0.4604 (5)	0.7251 (5)	0.3340 (3)	0.0750 (14)
H24A	0.4234	0.6425	0.3291	0.112*
H24B	0.5589	0.7418	0.3671	0.112*
H24C	0.4566	0.7289	0.2796	0.112*
C25	0.4237 (4)	0.9557 (4)	0.3841 (3)	0.0658 (11)
H25A	0.3643	1.0157	0.4103	0.099*
H25B	0.4192	0.9609	0.3299	0.099*
H25C	0.5219	0.9744	0.4174	0.099*
O31	0.8968 (3)	0.6711 (2)	0.25551 (14)	0.0475 (6)
O32	0.8201 (3)	0.5390 (2)	0.31209 (14)	0.0573 (7)
H32	0.8487	0.5985	0.3554	0.086*
C31	0.8441 (3)	0.5699 (3)	0.24979 (18)	0.0345 (7)
C32	0.7936 (3)	0.4635 (3)	0.16793 (17)	0.0314 (6)
H32A	0.8012	0.3824	0.1780	0.038*
N31	0.8923 (3)	0.4737 (2)	0.11565 (15)	0.0344 (6)
H31A	0.8658	0.4123	0.0667	0.052*
H31B	0.9827	0.4666	0.1414	0.052*
H31C	0.8872	0.5483	0.1077	0.052*
C33	0.6353 (4)	0.4736 (3)	0.1242 (2)	0.0430 (8)
H33	0.6268	0.5595	0.1219	0.052*
C34	0.5349 (5)	0.4500 (6)	0.1735 (3)	0.0844 (16)
H34A	0.5641	0.5082	0.2294	0.127*
H34B	0.5393	0.3651	0.1747	0.127*
H34C	0.4377	0.4618	0.1478	0.127*
C35	0.5889 (4)	0.3815 (4)	0.0358 (2)	0.0606 (11)
H35A	0.6527	0.3961	0.0045	0.091*
H35B	0.4918	0.3936	0.0101	0.091*
H35C	0.5929	0.2965	0.0370	0.091*
O41	0.1078 (3)	0.4142 (2)	0.24196 (14)	0.0470 (6)
O42	0.1884 (3)	0.2272 (3)	0.18719 (14)	0.0566 (7)
H42	0.1615	0.2429	0.1436	0.085*
C41	0.1609 (3)	0.3196 (3)	0.24838 (18)	0.0349 (7)
C42	0.2078 (3)	0.2956 (3)	0.33083 (17)	0.0318 (7)
H42A	0.2007	0.2044	0.3209	0.038*
N41	0.1078 (3)	0.3558 (2)	0.38156 (15)	0.0341 (6)
H41A	0.1331	0.3433	0.4306	0.051*
H41B	0.0178	0.3220	0.3550	0.051*
H41C	0.1127	0.4384	0.3895	0.051*
C43	0.3651 (4)	0.3510 (4)	0.3754 (2)	0.0441 (8)
H43	0.3716	0.4404	0.3799	0.053*
C44	0.4689 (5)	0.2850 (6)	0.3252 (3)	0.0845 (16)
H44A	0.4392	0.2900	0.2700	0.127*
H44B	0.4678	0.1980	0.3222	0.127*
H44C	0.5650	0.3254	0.3519	0.127*
C45	0.4122 (4)	0.3429 (4)	0.4625 (2)	0.0593 (10)
H45A	0.3469	0.3844	0.4941	0.089*
H45B	0.5083	0.3833	0.4892	0.089*
H45C	0.4111	0.2558	0.4594	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0445 (15)	0.0408 (16)	0.0332 (15)	0.0095 (12)	0.0112 (11)	0.0160 (12)
O1A	0.0677 (17)	0.0613 (17)	0.0492 (15)	0.0133 (13)	0.0218 (13)	0.0368 (13)
O1B	0.0895 (19)	0.0365 (13)	0.0343 (13)	0.0090 (12)	0.0270 (12)	0.0076 (10)
O1C	0.0804 (18)	0.0363 (14)	0.0311 (12)	0.0042 (12)	0.0161 (12)	0.0075 (10)
N2	0.0472 (16)	0.0418 (16)	0.0358 (15)	0.0136 (12)	0.0165 (12)	0.0162 (13)
O2A	0.087 (2)	0.0676 (18)	0.0550 (16)	0.0205 (15)	0.0277 (15)	0.0412 (15)
O2B	0.095 (2)	0.0382 (14)	0.0376 (14)	0.0090 (13)	0.0312 (13)	0.0081 (10)
O2C	0.0741 (17)	0.0393 (14)	0.0322 (12)	0.0129 (12)	0.0156 (11)	0.0086 (10)
N3	0.0483 (16)	0.0375 (16)	0.0356 (15)	0.0060 (12)	0.0143 (12)	0.0123 (12)
O3A	0.0746 (18)	0.0352 (14)	0.0520 (15)	0.0093 (12)	0.0278 (13)	0.0027 (11)
O3B	0.101 (2)	0.0456 (14)	0.0380 (14)	0.0210 (14)	0.0335 (14)	0.0204 (11)
O3C	0.0761 (17)	0.0411 (13)	0.0318 (12)	0.0097 (12)	0.0156 (11)	0.0164 (10)
N4	0.0436 (15)	0.0382 (16)	0.0354 (15)	0.0045 (12)	0.0150 (12)	0.0119 (12)
O4A	0.090 (2)	0.0360 (14)	0.0525 (16)	0.0062 (13)	0.0262 (15)	−0.0026 (12)
O4B	0.0886 (19)	0.0457 (14)	0.0350 (13)	0.0162 (13)	0.0275 (12)	0.0182 (11)
O4C	0.0784 (18)	0.0453 (14)	0.0316 (12)	0.0034 (12)	0.0147 (12)	0.0166 (10)
O11	0.0607 (15)	0.0418 (14)	0.0333 (12)	−0.0067 (12)	0.0131 (11)	0.0049 (10)
O12	0.100 (2)	0.0550 (16)	0.0260 (12)	−0.0188 (14)	0.0251 (13)	0.0008 (11)
C11	0.0423 (17)	0.0397 (19)	0.0247 (15)	0.0016 (14)	0.0078 (13)	0.0100 (13)
C12	0.0451 (18)	0.0307 (16)	0.0264 (15)	0.0025 (13)	0.0134 (13)	0.0095 (12)
N11	0.0417 (14)	0.0354 (14)	0.0264 (13)	0.0080 (11)	0.0117 (11)	0.0083 (11)
C13	0.0431 (19)	0.054 (2)	0.0357 (18)	0.0001 (15)	0.0122 (14)	0.0052 (15)
C14	0.062 (3)	0.091 (3)	0.064 (3)	−0.022 (2)	0.019 (2)	0.017 (2)
C15	0.054 (2)	0.086 (3)	0.073 (3)	0.021 (2)	0.009 (2)	0.031 (2)
O21	0.0608 (15)	0.0515 (15)	0.0341 (12)	0.0209 (12)	0.0119 (11)	0.0222 (11)
O22	0.096 (2)	0.0636 (17)	0.0251 (12)	0.0341 (15)	0.0230 (12)	0.0175 (11)
C21	0.0420 (17)	0.0373 (17)	0.0257 (15)	0.0055 (14)	0.0080 (13)	0.0106 (13)
C22	0.0477 (18)	0.0340 (16)	0.0273 (15)	0.0129 (14)	0.0125 (13)	0.0129 (12)
N21	0.0452 (15)	0.0356 (14)	0.0253 (13)	0.0063 (11)	0.0109 (11)	0.0106 (11)
C23	0.0480 (19)	0.058 (2)	0.0327 (17)	0.0141 (16)	0.0096 (14)	0.0171 (15)
C24	0.063 (3)	0.097 (4)	0.068 (3)	0.040 (3)	0.022 (2)	0.027 (3)
C25	0.051 (2)	0.071 (3)	0.065 (3)	−0.005 (2)	0.0113 (19)	0.011 (2)
O31	0.0638 (15)	0.0398 (14)	0.0333 (12)	−0.0064 (11)	0.0123 (11)	0.0049 (10)
O32	0.094 (2)	0.0496 (15)	0.0270 (12)	−0.0076 (14)	0.0201 (12)	0.0073 (11)
C31	0.0393 (17)	0.0400 (19)	0.0255 (15)	0.0065 (14)	0.0091 (12)	0.0120 (13)
C32	0.0403 (17)	0.0294 (15)	0.0249 (14)	0.0031 (12)	0.0093 (12)	0.0087 (12)
N31	0.0425 (14)	0.0339 (14)	0.0265 (13)	0.0078 (11)	0.0094 (11)	0.0090 (11)
C33	0.0415 (18)	0.0401 (18)	0.0410 (18)	0.0068 (14)	0.0084 (14)	0.0063 (14)
C34	0.053 (3)	0.120 (4)	0.069 (3)	−0.002 (3)	0.023 (2)	0.011 (3)
C35	0.060 (2)	0.057 (2)	0.052 (2)	0.0129 (19)	0.0000 (18)	0.0101 (18)
O41	0.0615 (15)	0.0510 (15)	0.0317 (12)	0.0209 (12)	0.0100 (11)	0.0193 (11)
O42	0.0865 (19)	0.0593 (16)	0.0250 (12)	0.0283 (14)	0.0162 (12)	0.0136 (11)
C41	0.0399 (17)	0.0360 (17)	0.0265 (15)	0.0073 (14)	0.0071 (13)	0.0084 (13)
C42	0.0421 (17)	0.0314 (16)	0.0258 (15)	0.0119 (13)	0.0128 (12)	0.0115 (12)
N41	0.0445 (15)	0.0340 (14)	0.0252 (12)	0.0060 (11)	0.0096 (11)	0.0113 (11)
C43	0.0437 (18)	0.059 (2)	0.0350 (17)	0.0053 (16)	0.0086 (14)	0.0236 (16)
C44	0.050 (2)	0.142 (5)	0.064 (3)	0.020 (3)	0.022 (2)	0.031 (3)
C45	0.057 (2)	0.075 (3)	0.045 (2)	0.001 (2)	−0.0009 (17)	0.0284 (19)

Geometric parameters (Å, º)

N1—O1A	1.226 (3)	C24—H24A	0.96
N1—O1B	1.249 (3)	C24—H24B	0.96
N1—O1C	1.266 (4)	C24—H24C	0.96
N2—O2A	1.222 (4)	C25—H25A	0.96
N2—O2B	1.246 (3)	C25—H25B	0.96
N2—O2C	1.268 (4)	C25—H25C	0.96
N3—O3A	1.224 (4)	O31—C31	1.204 (4)
N3—O3B	1.251 (3)	O32—C31	1.315 (4)
N3—O3C	1.268 (4)	O32—H32	0.82
N4—O4A	1.218 (4)	C31—C32	1.512 (4)
N4—O4B	1.246 (3)	C32—N31	1.495 (4)
N4—O4C	1.272 (4)	C32—C33	1.543 (4)
O11—C11	1.199 (4)	C32—H32A	0.98
O12—C11	1.312 (4)	N31—H31A	0.89
O12—H12	0.82	N31—H31B	0.89
C11—C12	1.517 (4)	N31—H31C	0.89
C12—N11	1.488 (4)	C33—C34	1.514 (6)
C12—C13	1.539 (5)	C33—C35	1.519 (5)
C12—H12A	0.98	C33—H33	0.98
N11—H11A	0.89	C34—H34A	0.96
N11—H11B	0.89	C34—H34B	0.96
N11—H11C	0.89	C34—H34C	0.96
C13—C15	1.513 (6)	C35—H35A	0.96
C13—C14	1.520 (5)	C35—H35B	0.96
C13—H13	0.98	C35—H35C	0.96
C14—H14A	0.96	O41—C41	1.204 (4)
C14—H14B	0.96	O42—C41	1.314 (4)
C14—H14C	0.96	O42—H42	0.82
C15—H15A	0.96	C41—C42	1.515 (4)
C15—H15B	0.96	C42—N41	1.485 (4)
C15—H15C	0.96	C42—C43	1.540 (5)
O21—C21	1.197 (4)	C42—H42A	0.98
O22—C21	1.315 (4)	N41—H41A	0.89
O22—H22	0.82	N41—H41B	0.89
C21—C22	1.521 (4)	N41—H41C	0.89
C22—N21	1.494 (4)	C43—C45	1.516 (5)
C22—C23	1.535 (5)	C43—C44	1.526 (5)
C22—H22A	0.98	C43—H43	0.98
N21—H21A	0.89	C44—H44A	0.96
N21—H21B	0.89	C44—H44B	0.96
N21—H21C	0.89	C44—H44C	0.96
C23—C25	1.519 (6)	C45—H45A	0.96
C23—C24	1.520 (5)	C45—H45B	0.96
C23—H23	0.98	C45—H45C	0.96
O1A—N1—O1B	121.4 (3)	C23—C25—H25A	109.5
O1A—N1—O1C	121.2 (3)	C23—C25—H25B	109.5
O1B—N1—O1C	117.4 (3)	H25A—C25—H25B	109.5
O2A—N2—O2B	121.8 (3)	C23—C25—H25C	109.5
O2A—N2—O2C	120.8 (3)	H25A—C25—H25C	109.5
O2B—N2—O2C	117.4 (3)	H25B—C25—H25C	109.5
O3A—N3—O3B	121.6 (3)	C31—O32—H32	109.5
O3A—N3—O3C	121.1 (3)	O31—C31—O32	125.1 (3)
O3B—N3—O3C	117.3 (3)	O31—C31—C32	123.0 (3)
O4A—N4—O4B	122.4 (3)	O32—C31—C32	111.9 (3)
O4A—N4—O4C	120.6 (3)	N31—C32—C31	106.9 (2)
O4B—N4—O4C	117.0 (3)	N31—C32—C33	110.7 (2)
C11—O12—H12	109.5	C31—C32—C33	110.9 (2)
O11—C11—O12	125.6 (3)	N31—C32—H32A	109.4
O11—C11—C12	123.4 (3)	C31—C32—H32A	109.4
O12—C11—C12	111.0 (3)	C33—C32—H32A	109.4
N11—C12—C11	107.6 (2)	C32—N31—H31A	109.5
N11—C12—C13	111.2 (2)	C32—N31—H31B	109.5
C11—C12—C13	113.2 (3)	H31A—N31—H31B	109.5
N11—C12—H12A	108.2	C32—N31—H31C	109.5
C11—C12—H12A	108.2	H31A—N31—H31C	109.5
C13—C12—H12A	108.2	H31B—N31—H31C	109.5
C12—N11—H11A	109.5	C34—C33—C35	109.4 (3)
C12—N11—H11B	109.5	C34—C33—C32	110.2 (3)
H11A—N11—H11B	109.5	C35—C33—C32	112.2 (3)
C12—N11—H11C	109.5	C34—C33—H33	108.3
H11A—N11—H11C	109.5	C35—C33—H33	108.3
H11B—N11—H11C	109.5	C32—C33—H33	108.3
C15—C13—C14	111.8 (4)	C33—C34—H34A	109.5
C15—C13—C12	113.2 (3)	C33—C34—H34B	109.5
C14—C13—C12	110.8 (3)	H34A—C34—H34B	109.5
C15—C13—H13	106.9	C33—C34—H34C	109.5
C14—C13—H13	106.9	H34A—C34—H34C	109.5
C12—C13—H13	106.9	H34B—C34—H34C	109.5
C13—C14—H14A	109.5	C33—C35—H35A	109.5
C13—C14—H14B	109.5	C33—C35—H35B	109.5
H14A—C14—H14B	109.5	H35A—C35—H35B	109.5
C13—C14—H14C	109.5	C33—C35—H35C	109.5
H14A—C14—H14C	109.5	H35A—C35—H35C	109.5
H14B—C14—H14C	109.5	H35B—C35—H35C	109.5
C13—C15—H15A	109.5	C41—O42—H42	109.5
C13—C15—H15B	109.5	O41—C41—O42	125.4 (3)
H15A—C15—H15B	109.5	O41—C41—C42	122.7 (3)
C13—C15—H15C	109.5	O42—C41—C42	111.9 (3)
H15A—C15—H15C	109.5	N41—C42—C41	107.5 (2)
H15B—C15—H15C	109.5	N41—C42—C43	110.9 (3)
C21—O22—H22	109.5	C41—C42—C43	110.1 (3)
O21—C21—O22	125.4 (3)	N41—C42—H42A	109.4
O21—C21—C22	123.7 (3)	C41—C42—H42A	109.4
O22—C21—C22	110.9 (3)	C43—C42—H42A	109.4
N21—C22—C21	107.0 (2)	C42—N41—H41A	109.5
N21—C22—C23	110.8 (3)	C42—N41—H41B	109.5
C21—C22—C23	113.8 (3)	H41A—N41—H41B	109.5
N21—C22—H22A	108.4	C42—N41—H41C	109.5
C21—C22—H22A	108.4	H41A—N41—H41C	109.5
C23—C22—H22A	108.4	H41B—N41—H41C	109.5
C22—N21—H21A	109.5	C45—C43—C44	109.4 (3)
C22—N21—H21B	109.5	C45—C43—C42	112.3 (3)
H21A—N21—H21B	109.5	C44—C43—C42	111.0 (3)
C22—N21—H21C	109.5	C45—C43—H43	108.0
H21A—N21—H21C	109.5	C44—C43—H43	108.0
H21B—N21—H21C	109.5	C42—C43—H43	108.0
C25—C23—C24	111.3 (4)	C43—C44—H44A	109.5
C25—C23—C22	113.5 (3)	C43—C44—H44B	109.5
C24—C23—C22	110.7 (3)	H44A—C44—H44B	109.5
C25—C23—H23	107.0	C43—C44—H44C	109.5
C24—C23—H23	107.0	H44A—C44—H44C	109.5
C22—C23—H23	107.0	H44B—C44—H44C	109.5
C23—C24—H24A	109.5	C43—C45—H45A	109.5
C23—C24—H24B	109.5	C43—C45—H45B	109.5
H24A—C24—H24B	109.5	H45A—C45—H45B	109.5
C23—C24—H24C	109.5	C43—C45—H45C	109.5
H24A—C24—H24C	109.5	H45A—C45—H45C	109.5
H24B—C24—H24C	109.5	H45B—C45—H45C	109.5
O11—C11—C12—N11	19.9 (4)	O31—C31—C32—N31	33.1 (4)
O12—C11—C12—N11	−161.0 (3)	O32—C31—C32—N31	−148.5 (3)
O11—C11—C12—C13	−103.4 (4)	O31—C31—C32—C33	−87.7 (4)
O12—C11—C12—C13	75.6 (4)	O32—C31—C32—C33	90.8 (3)
N11—C12—C13—C15	−74.5 (4)	N31—C32—C33—C34	174.3 (3)
C11—C12—C13—C15	46.8 (4)	C31—C32—C33—C34	−67.3 (4)
N11—C12—C13—C14	159.0 (3)	N31—C32—C33—C35	52.2 (4)
C11—C12—C13—C14	−79.7 (4)	C31—C32—C33—C35	170.7 (3)
O21—C21—C22—N21	22.6 (4)	O41—C41—C42—N41	32.6 (4)
O22—C21—C22—N21	−158.5 (3)	O42—C41—C42—N41	−148.8 (3)
O21—C21—C22—C23	−100.1 (4)	O41—C41—C42—C43	−88.3 (4)
O22—C21—C22—C23	78.8 (4)	O42—C41—C42—C43	90.2 (3)
N21—C22—C23—C25	−73.3 (4)	N41—C42—C43—C45	54.6 (4)
C21—C22—C23—C25	47.3 (4)	C41—C42—C43—C45	173.5 (3)
N21—C22—C23—C24	160.7 (3)	N41—C42—C43—C44	177.4 (3)
C21—C22—C23—C24	−78.7 (4)	C41—C42—C43—C44	−63.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O1C^i	0.82	1.87	2.636 (3)	155
N11—H11B···O21^ii	0.89	2.18	2.907 (3)	138
N11—H11B···O4A^iii	0.89	2.53	3.014 (4)	115
N11—H11C···O4B^iv	0.89	1.97	2.843 (4)	168
N11—H11A···O3C^v	0.89	2.02	2.914 (4)	179
N11—H11A···O3B^v	0.89	2.46	3.048 (4)	124
O22—H22···O4C^v	0.82	1.84	2.628 (3)	160
N21—H21C···O2B^iv	0.89	1.96	2.840 (4)	168
N21—H21A···O1C	0.89	2.01	2.899 (3)	178
N21—H21A···O1B	0.89	2.50	3.061 (4)	122
N21—H21B···O31^vi	0.89	2.20	2.920 (4)	138
N21—H21B···O2A^vii	0.89	2.45	2.968 (4)	117
O32—H32···O2C^viii	0.82	1.88	2.660 (3)	160
N31—H31B···O41^ii	0.89	2.13	2.885 (3)	143
N31—H31B···O3A^ii	0.89	2.47	2.963 (4)	116
N31—H31A···O4C	0.89	2.08	2.946 (4)	165
N31—H31A···O4B	0.89	2.50	3.019 (4)	118
N31—H31C···O3B^v	0.89	1.97	2.835 (4)	163
O42—H42···O3C	0.82	1.91	2.667 (3)	152
N41—H41B···O11^ix	0.89	2.11	2.877 (4)	144
N41—H41B···O1A^vii	0.89	2.54	3.011 (4)	114
N41—H41C···O1B	0.89	1.97	2.832 (4)	163
N41—H41A···O2C	0.89	2.09	2.954 (3)	165
N41—H41A···O2B	0.89	2.47	3.004 (4)	119

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