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The title compound, C5H12NO2+·ClO4, crystallizes in the triclinic space group P\overline 1 with four valinium cations and four perchlorate anions in the asymmetric unit. In the crystal, three of the four crystallographically independent valinium residues are linked to the perchlorate anions via O—H...O hydrogen bonds. The fourth residue, on the other hand, forms O—H...O hydrogen bonds with an inversion-related residue, thereby forming a dimer. Both class I and class III hydrogen-bonding patterns are observed. All the four residues have similar gauche II–gauche I side-chain conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022225/ci6187sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022225/ci6187Isup2.hkl
Contains datablock I

CCDC reference: 202989

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.105
  • Data-to-parameter ratio = 32.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 35.06 From the CIF: _reflns_number_total 15604 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 16726 Completeness (_total/calc) 93.29% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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 perchlorate top
Crystal data top
C5H12NO2+·ClO4Z = 8
Mr = 217.61F(000) = 912
Triclinic, P1Dx = 1.530 Mg m3
Dm = 1.50 Mg m3
Dm measured by flotation in a mixture of carbon tetrachloride and xylene
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 10.3005 (6) ÅCell parameters from 8152 reflections
b = 13.0905 (8) Åθ = 2.5–35.0°
c = 14.6105 (9) ŵ = 0.41 mm1
α = 81.288 (2)°T = 105 K
β = 88.4473 (19)°Plate, colorless
γ = 75.9648 (19)°0.7 × 0.5 × 0.15 mm
V = 1889.1 (2) Å3
Data collection top
Bruker SMART CCD
diffractometer
15604 independent reflections
Radiation source: fine-focus sealed tube12138 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 8.33 pixels mm-1θmax = 35.1°, θmin = 1.4°
ω scansh = 1616
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2121
Tmin = 0.76, Tmax = 0.94l = 2323
35831 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0522P)2 + 0.6779P]
where P = (Fo2 + 2Fc2)/3
15604 reflections(Δ/σ)max = 0.002
485 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 0.54 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.66873 (2)0.893149 (19)0.817212 (17)0.01552 (5)
O110.76072 (9)0.84376 (8)0.89155 (6)0.02528 (18)
O120.73948 (9)0.92487 (7)0.73479 (6)0.02430 (17)
O130.59270 (9)0.82024 (7)0.79486 (6)0.02318 (17)
O140.57590 (10)0.98674 (8)0.84367 (7)0.0308 (2)
Cl20.66344 (2)1.005117 (19)0.408864 (17)0.01586 (5)
O210.74562 (10)1.01445 (8)0.32912 (7)0.0295 (2)
O220.54022 (10)0.98222 (9)0.38580 (8)0.0347 (2)
O230.73582 (10)0.92302 (8)0.47938 (8)0.0338 (2)
O240.63256 (9)1.10502 (7)0.44624 (6)0.02397 (17)
Cl30.33296 (3)0.501837 (19)0.098497 (17)0.01683 (5)
O310.36925 (14)0.57718 (9)0.02752 (10)0.0550 (4)
O320.19527 (10)0.53822 (9)0.12232 (7)0.0322 (2)
O330.35737 (9)0.39904 (7)0.06830 (7)0.02488 (18)
O340.41625 (12)0.49198 (9)0.17972 (8)0.0414 (3)
Cl40.67119 (2)0.378808 (19)0.330192 (16)0.01480 (5)
O410.76844 (9)0.33058 (8)0.40217 (6)0.02494 (17)
O420.73619 (9)0.41280 (7)0.24598 (6)0.02373 (17)
O430.59667 (9)0.30374 (7)0.31094 (6)0.02147 (16)
O440.57803 (9)0.47075 (7)0.35974 (7)0.02634 (19)
O1A0.56652 (9)0.27665 (7)0.75114 (6)0.02522 (18)
O1B0.71043 (10)0.37587 (7)0.69865 (7)0.02738 (19)
H1B0.670 (2)0.4151 (16)0.7383 (14)0.041 (5)*
C110.65508 (11)0.29506 (8)0.69959 (7)0.01787 (19)
C120.71516 (10)0.22531 (8)0.62752 (7)0.01470 (17)
H120.69770.26880.56630.018*
N10.64138 (9)0.13933 (7)0.63272 (6)0.01647 (16)
H1A0.67420.09680.59120.025*
H1C0.55490.16840.62090.025*
H1D0.65110.10160.68920.025*
C130.86793 (11)0.18040 (9)0.63866 (8)0.01858 (19)
H130.90950.24050.62220.022*
C140.91084 (13)0.13110 (11)0.73832 (9)0.0260 (2)
H14A0.87700.18230.77910.039*
H14B1.00680.11060.74250.039*
H14C0.87570.06950.75590.039*
C150.91918 (12)0.10227 (11)0.56990 (10)0.0276 (3)
H15A0.89040.13610.50840.041*
H15B0.88410.04040.58580.041*
H15C1.01520.08150.57250.041*
O2A0.43593 (9)0.30578 (7)0.53587 (6)0.02418 (17)
O2B0.31609 (10)0.47309 (7)0.49077 (6)0.02417 (17)
H2B0.352 (2)0.4873 (15)0.5387 (14)0.038 (5)*
C210.36053 (11)0.37166 (8)0.48176 (7)0.01643 (18)
C220.30666 (10)0.34589 (8)0.39431 (7)0.01484 (17)
H220.34280.38490.34100.018*
N20.36225 (9)0.22939 (7)0.39283 (6)0.01628 (16)
H2A0.33280.21120.34240.024*
H2C0.33580.19240.44300.024*
H2D0.45120.21530.39220.024*
C230.15237 (10)0.37941 (9)0.38645 (7)0.01732 (18)
H230.12660.45740.37640.021*
C240.10323 (13)0.34255 (11)0.30178 (9)0.0254 (2)
H24A0.14820.36710.24750.038*
H24B0.00850.37130.29410.038*
H24C0.12230.26620.31070.038*
C250.08330 (12)0.34197 (12)0.47498 (9)0.0271 (2)
H25A0.11600.36620.52670.041*
H25B0.10220.26560.48520.041*
H25C0.01160.37070.46860.041*
O3A0.87416 (8)0.50013 (6)0.07502 (6)0.01906 (15)
O3B0.93978 (8)0.64102 (7)0.00291 (6)0.02141 (16)
H3B1.004 (2)0.5902 (16)0.0235 (14)0.042 (5)*
C310.86245 (10)0.59610 (8)0.05362 (7)0.01574 (17)
C320.75478 (10)0.67735 (8)0.09498 (7)0.01546 (17)
H320.71680.73580.04570.019*
N30.64675 (9)0.62359 (7)0.13106 (6)0.01619 (16)
H3A0.58230.66960.15570.024*
H3C0.68090.56840.17410.024*
H3D0.61290.60080.08480.024*
C330.81640 (12)0.72299 (9)0.17046 (8)0.0203 (2)
H330.88550.75570.14010.024*
C340.71305 (15)0.81187 (13)0.20703 (13)0.0395 (4)
H34A0.67150.86360.15600.059*
H34B0.75640.84540.24710.059*
H34C0.64620.78250.24100.059*
C350.88633 (18)0.63760 (12)0.24833 (10)0.0361 (3)
H35A0.95020.58340.22240.054*
H35B0.82120.60650.28270.054*
H35C0.93160.66930.28880.054*
O4A0.53591 (9)0.19130 (7)0.98022 (6)0.02402 (17)
O4B0.67023 (10)0.02596 (7)1.00905 (7)0.02782 (19)
H4B0.633 (2)0.0168 (17)0.9597 (15)0.045 (6)*
C410.62229 (11)0.12492 (9)1.02561 (7)0.01772 (18)
C420.68971 (10)0.14625 (8)1.11005 (7)0.01526 (17)
H420.66820.09981.16450.018*
N40.62721 (9)0.25923 (7)1.12166 (6)0.01644 (16)
H4A0.66380.27521.17050.025*
H4C0.53970.26731.13030.025*
H4D0.64100.30241.07110.025*
C430.84372 (11)0.12400 (9)1.10210 (8)0.01909 (19)
H430.87840.04651.11030.023*
C440.88945 (14)0.16861 (12)1.00713 (10)0.0302 (3)
H44A0.85050.14180.95970.045*
H44B0.98520.14711.00390.045*
H44C0.86140.24500.99820.045*
C450.90418 (12)0.16514 (11)1.18006 (9)0.0258 (2)
H45A0.87410.13611.23880.039*
H45B0.87620.24151.17210.039*
H45C1.00000.14351.17790.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01572 (10)0.01488 (10)0.01617 (10)0.00331 (8)0.00024 (8)0.00355 (8)
O110.0240 (4)0.0285 (4)0.0196 (4)0.0016 (3)0.0055 (3)0.0012 (3)
O120.0244 (4)0.0269 (4)0.0217 (4)0.0112 (3)0.0025 (3)0.0040 (3)
O130.0276 (4)0.0255 (4)0.0225 (4)0.0162 (3)0.0049 (3)0.0074 (3)
O140.0273 (5)0.0269 (4)0.0362 (5)0.0070 (4)0.0081 (4)0.0191 (4)
Cl20.01441 (10)0.01559 (10)0.01817 (11)0.00497 (8)0.00199 (8)0.00248 (8)
O210.0307 (5)0.0366 (5)0.0229 (4)0.0107 (4)0.0129 (3)0.0079 (4)
O220.0265 (5)0.0456 (6)0.0405 (6)0.0219 (4)0.0010 (4)0.0118 (5)
O230.0258 (5)0.0247 (4)0.0419 (6)0.0007 (4)0.0009 (4)0.0142 (4)
O240.0279 (4)0.0198 (4)0.0244 (4)0.0029 (3)0.0008 (3)0.0081 (3)
Cl30.01736 (11)0.01462 (10)0.01771 (11)0.00293 (8)0.00001 (8)0.00137 (8)
O310.0529 (7)0.0309 (6)0.0645 (8)0.0004 (5)0.0249 (6)0.0236 (6)
O320.0223 (4)0.0368 (5)0.0351 (5)0.0003 (4)0.0066 (4)0.0115 (4)
O330.0243 (4)0.0203 (4)0.0302 (4)0.0002 (3)0.0058 (3)0.0115 (3)
O340.0375 (6)0.0400 (6)0.0454 (6)0.0068 (5)0.0205 (5)0.0244 (5)
Cl40.01465 (10)0.01603 (10)0.01437 (10)0.00412 (8)0.00006 (7)0.00359 (8)
O410.0227 (4)0.0295 (4)0.0205 (4)0.0031 (3)0.0075 (3)0.0010 (3)
O420.0240 (4)0.0247 (4)0.0214 (4)0.0079 (3)0.0059 (3)0.0023 (3)
O430.0246 (4)0.0223 (4)0.0216 (4)0.0129 (3)0.0011 (3)0.0045 (3)
O440.0218 (4)0.0273 (4)0.0296 (4)0.0028 (3)0.0036 (3)0.0168 (4)
O1A0.0281 (4)0.0242 (4)0.0242 (4)0.0068 (3)0.0110 (3)0.0075 (3)
O1B0.0385 (5)0.0198 (4)0.0281 (4)0.0125 (4)0.0077 (4)0.0095 (3)
C110.0214 (5)0.0149 (4)0.0168 (4)0.0034 (4)0.0015 (4)0.0026 (3)
C120.0160 (4)0.0144 (4)0.0140 (4)0.0043 (3)0.0016 (3)0.0021 (3)
N10.0151 (4)0.0167 (4)0.0184 (4)0.0047 (3)0.0002 (3)0.0037 (3)
C130.0147 (4)0.0213 (5)0.0208 (5)0.0057 (4)0.0011 (3)0.0044 (4)
C140.0214 (5)0.0289 (6)0.0267 (6)0.0058 (4)0.0079 (4)0.0003 (5)
C150.0169 (5)0.0326 (6)0.0342 (6)0.0020 (4)0.0050 (4)0.0149 (5)
O2A0.0265 (4)0.0216 (4)0.0223 (4)0.0001 (3)0.0088 (3)0.0048 (3)
O2B0.0306 (5)0.0187 (4)0.0231 (4)0.0012 (3)0.0062 (3)0.0090 (3)
C210.0161 (4)0.0173 (4)0.0165 (4)0.0037 (3)0.0001 (3)0.0049 (3)
C220.0160 (4)0.0143 (4)0.0143 (4)0.0033 (3)0.0001 (3)0.0029 (3)
N20.0169 (4)0.0159 (4)0.0164 (4)0.0029 (3)0.0004 (3)0.0048 (3)
C230.0146 (4)0.0175 (4)0.0189 (4)0.0019 (3)0.0015 (3)0.0024 (4)
C240.0209 (5)0.0303 (6)0.0253 (5)0.0045 (4)0.0060 (4)0.0069 (5)
C250.0184 (5)0.0363 (7)0.0254 (6)0.0059 (5)0.0051 (4)0.0028 (5)
O3A0.0195 (4)0.0162 (3)0.0193 (4)0.0013 (3)0.0048 (3)0.0016 (3)
O3B0.0185 (4)0.0178 (4)0.0258 (4)0.0023 (3)0.0085 (3)0.0014 (3)
C310.0143 (4)0.0178 (4)0.0140 (4)0.0019 (3)0.0009 (3)0.0022 (3)
C320.0145 (4)0.0154 (4)0.0157 (4)0.0020 (3)0.0025 (3)0.0026 (3)
N30.0153 (4)0.0166 (4)0.0165 (4)0.0032 (3)0.0024 (3)0.0036 (3)
C330.0198 (5)0.0212 (5)0.0224 (5)0.0070 (4)0.0031 (4)0.0078 (4)
C340.0291 (7)0.0372 (7)0.0588 (10)0.0060 (6)0.0056 (6)0.0325 (7)
C350.0504 (9)0.0354 (7)0.0241 (6)0.0115 (6)0.0136 (6)0.0055 (5)
O4A0.0236 (4)0.0264 (4)0.0212 (4)0.0023 (3)0.0058 (3)0.0057 (3)
O4B0.0318 (5)0.0237 (4)0.0295 (5)0.0026 (4)0.0044 (4)0.0148 (4)
C410.0179 (4)0.0199 (5)0.0170 (4)0.0054 (4)0.0015 (3)0.0068 (4)
C420.0163 (4)0.0152 (4)0.0145 (4)0.0034 (3)0.0004 (3)0.0032 (3)
N40.0173 (4)0.0165 (4)0.0160 (4)0.0034 (3)0.0003 (3)0.0049 (3)
C430.0153 (4)0.0197 (5)0.0219 (5)0.0036 (4)0.0012 (4)0.0032 (4)
C440.0257 (6)0.0394 (7)0.0266 (6)0.0111 (5)0.0096 (5)0.0039 (5)
C450.0185 (5)0.0312 (6)0.0295 (6)0.0077 (4)0.0041 (4)0.0064 (5)
Geometric parameters (Å, º) top
Cl1—O111.4287 (9)C23—C241.5339 (16)
Cl1—O121.4497 (9)C23—H230.98
Cl1—O131.4498 (9)C24—H24A0.96
Cl1—O141.4560 (9)C24—H24B0.96
Cl2—O211.4292 (9)C24—H24C0.96
Cl2—O221.4327 (10)C25—H25A0.96
Cl2—O231.4456 (10)C25—H25B0.96
Cl2—O241.4543 (9)C25—H25C0.96
Cl3—O311.4269 (11)O3A—C311.2248 (13)
Cl3—O321.4337 (10)O3B—C311.3064 (13)
Cl3—O331.4416 (9)O3B—H3B0.90 (2)
Cl3—O341.4547 (10)C31—C321.5208 (14)
Cl4—O411.4342 (9)C32—N31.4989 (14)
Cl4—O421.4471 (9)C32—C331.5484 (16)
Cl4—O431.4475 (8)C32—H320.98
Cl4—O441.4596 (9)N3—H3A0.89
O1A—C111.2132 (14)N3—H3C0.89
O1B—C111.3161 (14)N3—H3D0.89
O1B—H1B0.86 (2)C33—C341.5261 (17)
C11—C121.5190 (15)C33—C351.5269 (19)
C12—N11.4953 (13)C33—H330.98
C12—C131.5443 (15)C34—H34A0.96
C12—H120.98C34—H34B0.96
N1—H1A0.89C34—H34C0.96
N1—H1C0.89C35—H35A0.96
N1—H1D0.89C35—H35B0.96
C13—C141.5309 (17)C35—H35C0.96
C13—C151.5345 (17)O4A—C411.2121 (14)
C13—H130.98O4B—C411.3262 (14)
C14—H14A0.96O4B—H4B0.86 (2)
C14—H14B0.96C41—C421.5254 (15)
C14—H14C0.96C42—N41.4962 (13)
C15—H15A0.96C42—C431.5463 (15)
C15—H15B0.96C42—H420.98
C15—H15C0.96N4—H4A0.89
O2A—C211.2141 (13)N4—H4C0.89
O2B—C211.3209 (13)N4—H4D0.89
O2B—H2B0.87 (2)C43—C441.5301 (17)
C21—C221.5212 (15)C43—C451.5369 (17)
C22—N21.4966 (13)C43—H430.98
C22—C231.5453 (15)C44—H44A0.96
C22—H220.98C44—H44B0.96
N2—H2A0.89C44—H44C0.96
N2—H2C0.89C45—H45A0.96
N2—H2D0.89C45—H45B0.96
C23—C251.5320 (16)C45—H45C0.96
O11—Cl1—O12110.58 (6)C23—C24—H24A109.5
O11—Cl1—O13110.72 (6)C23—C24—H24B109.5
O12—Cl1—O13107.98 (5)H24A—C24—H24B109.5
O11—Cl1—O14109.70 (6)C23—C24—H24C109.5
O12—Cl1—O14109.19 (6)H24A—C24—H24C109.5
O13—Cl1—O14108.63 (6)H24B—C24—H24C109.5
O21—Cl2—O22111.14 (6)C23—C25—H25A109.5
O21—Cl2—O23109.52 (6)C23—C25—H25B109.5
O22—Cl2—O23110.61 (7)H25A—C25—H25B109.5
O21—Cl2—O24109.24 (6)C23—C25—H25C109.5
O22—Cl2—O24108.44 (6)H25A—C25—H25C109.5
O23—Cl2—O24107.81 (6)H25B—C25—H25C109.5
O31—Cl3—O32109.92 (7)C31—O3B—H3B109.2 (13)
O31—Cl3—O33110.00 (7)O3A—C31—O3B125.86 (10)
O32—Cl3—O33111.06 (6)O3A—C31—C32121.89 (9)
O31—Cl3—O34108.49 (9)O3B—C31—C32112.21 (9)
O32—Cl3—O34109.04 (7)N3—C32—C31107.69 (8)
O33—Cl3—O34108.27 (6)N3—C32—C33113.06 (9)
O41—Cl4—O42110.42 (6)C31—C32—C33110.13 (9)
O41—Cl4—O43110.43 (5)N3—C32—H32108.6
O42—Cl4—O43108.45 (5)C31—C32—H32108.6
O41—Cl4—O44109.33 (5)C33—C32—H32108.6
O42—Cl4—O44109.40 (6)C32—N3—H3A109.5
O43—Cl4—O44108.78 (5)C32—N3—H3C109.5
C11—O1B—H1B108.8 (13)H3A—N3—H3C109.5
O1A—C11—O1B125.16 (10)C32—N3—H3D109.5
O1A—C11—C12122.82 (10)H3A—N3—H3D109.5
O1B—C11—C12112.02 (9)H3C—N3—H3D109.5
N1—C12—C11107.12 (8)C34—C33—C35112.19 (12)
N1—C12—C13112.34 (8)C34—C33—C32111.18 (10)
C11—C12—C13113.40 (9)C35—C33—C32113.27 (10)
N1—C12—H12107.9C34—C33—H33106.6
C11—C12—H12107.9C35—C33—H33106.6
C13—C12—H12107.9C32—C33—H33106.6
C12—N1—H1A109.5C33—C34—H34A109.5
C12—N1—H1C109.5C33—C34—H34B109.5
H1A—N1—H1C109.5H34A—C34—H34B109.5
C12—N1—H1D109.5C33—C34—H34C109.5
H1A—N1—H1D109.5H34A—C34—H34C109.5
H1C—N1—H1D109.5H34B—C34—H34C109.5
C14—C13—C15112.01 (10)C33—C35—H35A109.5
C14—C13—C12112.93 (9)C33—C35—H35B109.5
C15—C13—C12110.41 (9)H35A—C35—H35B109.5
C14—C13—H13107.0C33—C35—H35C109.5
C15—C13—H13107.0H35A—C35—H35C109.5
C12—C13—H13107.0H35B—C35—H35C109.5
C13—C14—H14A109.5C41—O4B—H4B109.7 (14)
C13—C14—H14B109.5O4A—C41—O4B125.17 (10)
H14A—C14—H14B109.5O4A—C41—C42123.30 (10)
C13—C14—H14C109.5O4B—C41—C42111.53 (9)
H14A—C14—H14C109.5N4—C42—C41106.44 (8)
H14B—C14—H14C109.5N4—C42—C43112.39 (9)
C13—C15—H15A109.5C41—C42—C43113.14 (9)
C13—C15—H15B109.5N4—C42—H42108.2
H15A—C15—H15B109.5C41—C42—H42108.2
C13—C15—H15C109.5C43—C42—H42108.2
H15A—C15—H15C109.5C42—N4—H4A109.5
H15B—C15—H15C109.5C42—N4—H4C109.5
C21—O2B—H2B110.7 (13)H4A—N4—H4C109.5
O2A—C21—O2B124.84 (10)C42—N4—H4D109.5
O2A—C21—C22123.15 (10)H4A—N4—H4D109.5
O2B—C21—C22112.02 (9)H4C—N4—H4D109.5
N2—C22—C21106.83 (8)C44—C43—C45111.04 (10)
N2—C22—C23113.00 (8)C44—C43—C42112.87 (10)
C21—C22—C23113.28 (9)C45—C43—C42110.94 (9)
N2—C22—H22107.8C44—C43—H43107.2
C21—C22—H22107.8C45—C43—H43107.2
C23—C22—H22107.8C42—C43—H43107.2
C22—N2—H2A109.5C43—C44—H44A109.5
C22—N2—H2C109.5C43—C44—H44B109.5
H2A—N2—H2C109.5H44A—C44—H44B109.5
C22—N2—H2D109.5C43—C44—H44C109.5
H2A—N2—H2D109.5H44A—C44—H44C109.5
H2C—N2—H2D109.5H44B—C44—H44C109.5
C25—C23—C24111.38 (10)C43—C45—H45A109.5
C25—C23—C22112.90 (9)C43—C45—H45B109.5
C24—C23—C22110.96 (9)H45A—C45—H45B109.5
C25—C23—H23107.1C43—C45—H45C109.5
C24—C23—H23107.1H45A—C45—H45C109.5
C22—C23—H23107.1H45B—C45—H45C109.5
O1A—C11—C12—N12.09 (14)O3A—C31—C32—N320.98 (14)
O1B—C11—C12—N1177.91 (9)O3B—C31—C32—N3161.07 (9)
O1A—C11—C12—C13122.43 (12)O3A—C31—C32—C33102.72 (12)
O1B—C11—C12—C1357.57 (12)O3B—C31—C32—C3375.23 (11)
N1—C12—C13—C1473.50 (12)N3—C32—C33—C3464.56 (13)
C11—C12—C13—C1448.14 (13)C31—C32—C33—C34174.92 (11)
N1—C12—C13—C1552.77 (12)N3—C32—C33—C3562.85 (13)
C11—C12—C13—C15174.41 (10)C31—C32—C33—C3557.67 (13)
O2A—C21—C22—N21.11 (14)O4A—C41—C42—N40.30 (15)
O2B—C21—C22—N2179.21 (9)O4B—C41—C42—N4179.76 (9)
O2A—C21—C22—C23126.19 (12)O4A—C41—C42—C43123.63 (12)
O2B—C21—C22—C2354.14 (12)O4B—C41—C42—C4356.32 (13)
N2—C22—C23—C2453.19 (12)N4—C42—C43—C4475.99 (12)
C21—C22—C23—C24174.87 (9)C41—C42—C43—C4444.61 (13)
N2—C22—C23—C2572.66 (12)N4—C42—C43—C4549.37 (12)
C21—C22—C23—C2549.02 (13)C41—C42—C43—C45169.97 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1B···O34i0.86 (2)1.89 (2)2.7503 (14)177 (2)
N1—H1A···O24ii0.892.152.8349 (13)133
N1—H1C···O2A0.892.152.8670 (12)137
N1—H1D···O12ii0.892.272.9264 (13)130
O2B—H2B···O44i0.87 (2)1.88 (2)2.7395 (12)175 (2)
N2—H2A···O13i0.892.192.9124 (13)138
N2—H2A···O12i0.892.513.3055 (13)149
N2—H2C···O23i0.892.022.8695 (13)159
N2—H2D···O24ii0.892.152.9234 (13)145
N2—H2D···O430.892.312.9731 (13)132
O3B—H3B···O3Aiii0.90 (2)1.74 (2)2.6381 (11)174 (2)
N3—H3A···O1Ai0.892.092.9288 (12)158
N3—H3D···O33iv0.892.252.9745 (13)139
N3—H3C···O420.892.102.9546 (13)161
O4B—H4B···O14ii0.86 (2)1.93 (2)2.7913 (13)172 (2)
N4—H4A···O43v0.892.202.9049 (12)135
N4—H4A···O42v0.892.513.3032 (13)148
N4—H4C···O13vi0.892.162.8827 (13)138
N4—H4C···O33v0.892.322.9834 (13)132
N4—H4D···O31i0.891.952.8208 (14)165
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z; (iii) x+2, y+1, z; (iv) x+1, y+1, z; (v) x, y, z+1; (vi) x+1, y+1, z+2.
 

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