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High-resolution low-temperature synchrotron X-ray diffraction data of the salt L-phenylalaninium hydrogen maleate are used to test the new automated iterative Hirshfeld atom refinement (HAR) procedure for the modelling of strong hydrogen bonds. The HAR models used present the first examples of Z′ > 1 treatments in the framework of wavefunction-based refinement methods. L-Phenylalaninium hydrogen maleate exhibits several hydrogen bonds in its crystal structure, of which the shortest and the most challenging to model is the O—H...O intramolecular hydrogen bond present in the hydrogen maleate anion (O...O distance is about 2.41 Å). In particular, the reconstruction of the electron density in the hydrogen maleate moiety and the determination of hydrogen-atom properties [positions, bond distances and anisotropic displacement parameters (ADPs)] are the focus of the study. For comparison to the HAR results, different spherical (independent atom model, IAM) and aspherical (free multipole model, MM; transferable aspherical atom model, TAAM) X-ray refinement techniques as well as results from a low-temperature neutron-diffraction experiment are employed. Hydrogen-atom ADPs are furthermore compared to those derived from a TLS/rigid-body (SHADE) treatment of the X-ray structures. The reference neutron-diffraction experiment reveals a truly symmetric hydrogen bond in the hydrogen maleate anion. Only with HAR is it possible to freely refine hydrogen-atom positions and ADPs from the X-ray data, which leads to the best electron-density model and the closest agreement with the structural parameters derived from the neutron-diffraction experiment, e.g. the symmetric hydrogen position can be reproduced. The multipole-based refinement techniques (MM and TAAM) yield slightly asymmetric positions, whereas the IAM yields a significantly asymmetric position.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053273314012443/kx5029sup1.cif
Contains datablocks global, xray, neutron

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053273314012443/kx5029xraysup2.hkl
Contains datablock xray

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053273314012443/kx5029neutronsup3.hkl
Contains datablock neutron

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053273314012443/kx5029sup4.pdf
Supporting information

CCDC reference: 1005733

Computing details top

Data collection: MAATEL/ANSTO control program for neutron. Data reduction: argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2011) for neutron. Program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003) for neutron.

(xray) top
Crystal data top
C9H12NO2·C4H3O4F(000) = 296
Mr = 281.27Dx = 1.459 Mg m3
Monoclinic, P21Synchrotron radiation, λ = 0.3540 Å
Hall symbol: P 2ybCell parameters from 124185 reflections
a = 10.905 (2) Åθ = 0.9–26.3°
b = 5.2338 (10) ŵ = 0.04 mm1
c = 11.439 (2) ÅT = 25 K
β = 101.36 (3)°Block, colorless
V = 640.1 (2) Å30.20 × 0.10 × 0.03 mm
Z = 2
Data collection top
SPring-8 BL02B1 Imaging plate camera
diffractometer
Rint = 0.022
Radiation source: synchrotronθmax = 23.2°, θmin = 0.9°
ω scansh = 2423
124185 measured reflectionsk = 1111
7820 independent reflectionsl = 2425
7370 reflections with I > 2σ(I)
Refinement top
Refinement on FSecondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020H atoms treated by a mixture of independent and constrained refinement
S = 0.86w = 1/σ(F)
7370 reflections(Δ/σ)max < 0.001
105 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.20 e Å3
211 constraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.3 (3)
Special details top

Refinement. . Hirshfeld atom refinement:. Uses aspherical atomic scattering factors obtained from Hirshfeld partitioning of a Gaussian quantum chemical wavefunction.. Hirshfeld weight functions obtained from spherically averaged unrestricted atomic densities.. Wavefunction type: rks becke88lyp using cluster charges, radius=8.0 angstrom. Gaussian basis set: cc-pVTZ. Refinement based on |F| with weight=1/σ(|F|). Negative |F|2 were pruned from the data. |F| < 4.0 σ(|F|) were pruned from the data. Eigenvalues < 0.1E-04 removed from normal equations. Reflection used in the refinement appear below. Refined using the Tonto program:. Version: 3.2 ($Rev: 4042 $). Platform: GNU-mpif90-on-LINUX. Build-date: Thu May 30 16:50:27 WST 2013

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzBiso*/Beq
O10.09516 (2)0.4786 (3)0.38078 (2)
O20.12318 (2)0.5095 (3)0.58415 (2)
O30.13521 (2)0.7084 (3)0.21652 (2)
O40.17832 (2)0.8004 (3)0.70331 (2)
C10.13464 (2)0.6824 (3)0.32530 (2)
C20.18015 (2)0.9012 (3)0.38884 (2)
C30.18958 (2)0.9238 (3)0.50385 (2)
C40.16122 (2)0.7356 (3)0.60348 (2)
H10.108 (1)0.490 (3)0.482 (1)
H20.205 (1)1.067 (2)0.3353 (8)
H30.223 (1)1.103 (2)0.5310 (8)
O50.22350 (2)1.0886 (3)0.09277 (2)
O60.09514 (2)0.9225 (3)0.01777 (2)
N10.12387 (2)1.2983 (3)0.17420 (2)
C50.16349 (2)1.0922 (3)0.00443 (2)
C60.18067 (2)1.3373 (3)0.06745 (2)
C70.31499 (2)1.4370 (3)0.10137 (2)
C80.40364 (2)1.2627 (3)0.18246 (2)
C90.41968 (2)1.2878 (3)0.30620 (2)
C100.49986 (3)1.1253 (3)0.38180 (2)
C110.56582 (2)0.9369 (3)0.33443 (2)
C120.55181 (2)0.9116 (3)0.21135 (2)
C130.47072 (2)1.0735 (3)0.13591 (2)
H410.137 (1)1.462 (2)0.2237 (9)
H420.1611 (9)1.145 (2)0.2191 (9)
H430.0284 (8)1.259 (2)0.1514 (9)
H50.191 (1)0.936 (3)0.147 (1)
H60.1241 (8)1.484 (2)0.0128 (8)
H710.3113 (9)1.624 (2)0.1428 (8)
H720.3460 (9)1.469 (2)0.0183 (7)
H90.3685 (8)1.440 (2)0.3399 (8)
H100.5120 (9)1.146 (2)0.4803 (7)
H110.6284 (9)0.811 (2)0.3954 (8)
H120.6043 (9)0.768 (2)0.1718 (8)
H130.4605 (9)1.056 (2)0.0400 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.01646 (7)0.01068 (7)0.00853 (7)0.00359 (6)0.00372 (6)0.00249 (5)
O20.01926 (8)0.01050 (7)0.00815 (7)0.00152 (6)0.00366 (6)0.00258 (6)
O30.01414 (7)0.01251 (7)0.00739 (7)0.00203 (5)0.00355 (5)0.00217 (5)
O40.01598 (7)0.01452 (8)0.00723 (7)0.00031 (6)0.00405 (6)0.00077 (6)
C10.00959 (7)0.00972 (8)0.00675 (8)0.00052 (6)0.00211 (6)0.00174 (6)
C20.01340 (8)0.00952 (8)0.00690 (8)0.00159 (6)0.00205 (6)0.00159 (6)
C30.01380 (8)0.01006 (8)0.00713 (8)0.00141 (7)0.00237 (6)0.00117 (6)
C40.01101 (7)0.01069 (8)0.00660 (8)0.00068 (6)0.00212 (6)0.00140 (6)
H10.0322290.0215930.0143230.0045600.0075000.002937
H20.0509080.0202880.0204260.0113010.0080150.008378
H30.0494930.0210230.0232460.0129740.0103980.000701
O50.01394 (7)0.01418 (8)0.00831 (7)0.00443 (6)0.00508 (5)0.00296 (6)
O60.01046 (6)0.00952 (6)0.00873 (7)0.00194 (5)0.00323 (5)0.00132 (5)
N10.00898 (6)0.01308 (8)0.00862 (7)0.00013 (6)0.00222 (5)0.00330 (6)
C50.00767 (6)0.00881 (7)0.00615 (7)0.00059 (6)0.00126 (5)0.00076 (6)
C60.00766 (7)0.00837 (7)0.00778 (8)0.00008 (6)0.00032 (5)0.00099 (6)
C70.00835 (7)0.00894 (8)0.00954 (8)0.00074 (6)0.00049 (6)0.00018 (6)
C80.00734 (6)0.00977 (8)0.00804 (8)0.00020 (6)0.00105 (5)0.00087 (6)
C90.01081 (8)0.01369 (9)0.00832 (8)0.00277 (7)0.00050 (6)0.00176 (7)
C100.01242 (8)0.0170 (1)0.00842 (9)0.00363 (7)0.00063 (7)0.00010 (7)
C110.01054 (8)0.0147 (1)0.01095 (9)0.00310 (7)0.00121 (6)0.00161 (8)
C120.01130 (8)0.0143 (1)0.01159 (9)0.00439 (7)0.00238 (7)0.00025 (8)
C130.01035 (7)0.01349 (9)0.00875 (8)0.00289 (7)0.00215 (6)0.00074 (7)
H410.0287720.0196970.0201080.0013660.0061970.008044
H420.0249670.0204370.0192320.0041870.0048380.003742
H430.0154420.0305400.0214180.0024310.0028410.001821
H50.0274830.0221410.0180630.0057530.0056640.007252
H60.0246630.0207670.0201080.0033060.0014610.002606
H710.0297410.0191370.0271740.0005700.0027750.008497
H720.0274610.0341900.0158480.0019890.0077200.001710
H90.0298960.0243160.0206370.0072240.0069260.005617
H100.0312000.0317220.0117580.0022310.0040560.002203
H110.0266940.0264690.0206630.0065780.0014060.003709
H120.0286940.0260020.0235560.0077860.0086780.005035
H130.0314820.0302880.0122210.0029000.0055850.003120
Geometric parameters (Å, º) top
O1—C11.2721 (19)C5—C61.5153 (19)
O1—H11.192 (8)C6—C71.5312 (9)
O2—C41.287 (2)C6—H61.100 (5)
O2—H11.219 (8)C7—C81.5080 (14)
O3—C11.2506 (5)C7—H711.089 (5)
O4—C41.2401 (7)C7—H721.082 (4)
C1—C21.4927 (17)C8—C91.3978 (5)
C2—C31.3449 (5)C8—C131.3974 (16)
C2—H21.065 (5)C9—C101.3921 (14)
C3—C41.4919 (15)C9—H91.085 (5)
C3—H31.074 (11)C10—C111.3917 (16)
O5—C51.3078 (2)C10—H101.114 (4)
O5—H51.026 (7)C11—C121.3923 (5)
O6—C51.2180 (17)C11—H111.096 (5)
N1—H411.022 (10)C12—C131.3943 (14)
N1—H420.996 (10)C12—H121.095 (5)
N1—H431.044 (9)C13—H131.085 (9)
O1—C1—O3121.50 (12)C4—C3—H3112.7 (5)
O2—C4—O4121.44 (11)C5—C6—H6106.7 (5)
O5—C5—O6124.79 (13)C6—C7—H71107.5 (5)
O1—C1—C2120.84 (6)C6—C7—H72106.2 (5)
O2—C4—C3120.07 (6)C7—C6—H6107.9 (5)
O3—C1—C2117.65 (13)C8—C7—H71110.4 (5)
O4—C4—C3118.47 (13)C8—C7—H72111.1 (5)
O5—C5—C6113.85 (11)C8—C9—H9117.3 (5)
O6—C5—C6121.30 (6)C8—C13—H13119.1 (5)
O1—H1—O2178 (1)C9—C10—H10120.4 (6)
C1—O1—H1110.4 (7)C10—C9—H9122.1 (5)
C4—O2—H1110.5 (7)C10—C11—H11119.0 (5)
C5—O5—H5108.1 (6)C11—C10—H10119.6 (6)
C1—C2—C3129.84 (12)C11—C12—H12121.4 (5)
C2—C3—C4130.16 (13)C12—C11—H11121.1 (5)
C5—C6—C7115.84 (7)C12—C13—H13120.2 (5)
C6—C7—C8114.53 (11)C13—C12—H12118.7 (5)
C7—C8—C9120.21 (10)C6—N1—H41107.8 (6)
C7—C8—C13120.97 (5)C6—N1—H42109.9 (5)
C8—C9—C10120.64 (10)C6—N1—H43112.3 (5)
C8—C13—C12120.70 (5)H71—C7—H72106.7 (8)
C9—C8—C13118.82 (9)H41—N1—H42113.2 (8)
C9—C10—C11120.04 (5)H41—N1—H43109.1 (9)
C10—C11—C12119.93 (9)H42—N1—H43104.7 (9)
C11—C12—C13119.87 (10)N1—C6—C5107.59 (11)
C1—C2—H2114.5 (5)N1—C6—C7111.77 (2)
C2—C3—H3117.1 (5)N1—C6—H6106.5 (5)
C3—C2—H2115.6 (5)
O3—C1—O1—H1176.8 (7)C7—C8—C9—H91.9 (6)
O4—C4—O2—H1177.5 (7)C7—C8—C13—H131.8 (6)
O6—C5—O5—H59.5 (8)C8—C7—C6—H6176.9 (5)
O1—C1—C2—C31.09 (4)C8—C9—C10—H10180.0 (6)
O2—C4—C3—C21.36 (4)C8—C13—C12—H12178.7 (7)
O3—C1—C2—C3179.88 (8)C9—C8—C7—H7131.2 (6)
O4—C4—C3—C2179.50 (3)C9—C8—C7—H72149.4 (6)
O5—C5—C6—C745.70 (3)C9—C8—C13—H13178.4 (6)
O6—C5—C6—C7137.11 (2)C9—C10—C11—H11180.0 (6)
O1—C1—C2—H2175.7 (7)C10—C11—C12—H12178.5 (7)
O2—C4—C3—H3178.1 (7)C11—C10—C9—H9178.5 (6)
O3—C1—C2—H23.3 (7)C11—C12—C13—H13179.1 (6)
O4—C4—C3—H30.0 (7)C12—C11—C10—H10179.5 (6)
O5—C5—C6—H674.4 (5)C13—C8—C7—H71148.9 (6)
O6—C5—C6—H6102.8 (5)C13—C8—C7—H7230.7 (6)
O5—C5—C6—N1171.56 (2)C13—C8—C9—H9178.3 (6)
O6—C5—C6—N111.24 (3)C13—C12—C11—H11179.5 (7)
C2—C1—O1—H14.1 (7)C5—C6—N1—H41179.0 (6)
C3—C4—O2—H14.5 (7)C5—C6—N1—H4255.2 (7)
C6—C5—O5—H5167.6 (8)C5—C6—N1—H4360.9 (7)
C1—C2—C3—C41.99 (5)C7—C6—N1—H4150.7 (6)
C5—C6—C7—C863.64 (3)C7—C6—N1—H4273.0 (7)
C6—C7—C8—C990.20 (3)C7—C6—N1—H43170.9 (7)
C6—C7—C8—C1389.62 (3)H2—C2—C3—H32 (1)
C7—C8—C9—C10179.03 (3)H6—C6—C7—H7153.8 (8)
C7—C8—C13—C12179.49 (10)H6—C6—C7—H7260.1 (8)
C8—C9—C10—C110.53 (4)H9—C9—C10—H101.2 (9)
C8—C13—C12—C110.41 (4)H10—C10—C11—H110.4 (9)
C9—C8—C13—C120.32 (4)H11—C11—C12—H121 (1)
C9—C10—C11—C120.19 (16)H12—C12—C13—H130.0 (9)
C10—C9—C8—C130.79 (4)H41—N1—C6—H666.8 (9)
C10—C11—C12—C130.68 (4)H42—N1—C6—H6169.4 (9)
C1—C2—C3—H3178.6 (7)H43—N1—C6—H653.3 (9)
C4—C3—C2—H2178.8 (7)N1—C6—C7—C860.06 (14)
C5—C6—C7—H71173.3 (6)N1—C6—C7—H7163.0 (6)
C5—C6—C7—H7259.4 (6)N1—C6—C7—H72176.9 (6)
(neutron) top
Crystal data top
C9H12NO2·C4H3O4F(000) = 152
Mr = 281.27Dx = 1.459 Mg m3
Monoclinic, P21Neutron radiation, λ = 0.85 Å
Hall symbol: P 2ybCell parameters from 124185 reflections
a = 10.905 (2) Åθ = 0.9–26.3°
b = 5.2338 (10) ŵ = 0.0 mm1
c = 11.439 (2) ÅT = 25 K
β = 101.36 (3)°Block, colorless
V = 640.1 (2) Å31.8 × 1.6 × 0.7 mm
Z = 2
Data collection top
KOALA
diffractometer
Rint = 0.064
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australiaθmax = 71.0°
Laue scansh = 1818
31922 measured reflectionsk = 1818
2487 independent reflectionsl = 1818
2231 reflections with > 3σ(F)
Refinement top
Refinement on FHydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.029 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 4.39 -0.947 1.73 1.80
wR(F2) = 0.029(Δ/σ)max = 0.0002806
S = 1.00Δρmax = 0.96 e Å3
2231 reflectionsΔρmin = 1.00 e Å3
317 parametersExtinction correction: Larson (1970), Equation 22
1 restraintExtinction coefficient: 5.6 (10)
Primary atom site location: isomorphous structure methods
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.09398 (11)0.4797 (3)0.38042 (10)0.0062
C10.13435 (9)0.6832 (2)0.32466 (9)0.0049
O30.13502 (11)0.7093 (3)0.21586 (10)0.0070
C20.18056 (9)0.9027 (2)0.38813 (9)0.0061
C30.18958 (9)0.9259 (2)0.50303 (8)0.0062
C40.16080 (9)0.7375 (2)0.60262 (8)0.0051
O20.12246 (11)0.5108 (3)0.58414 (10)0.0074
O40.17820 (12)0.8024 (3)0.70279 (10)0.0077
H30.2224 (3)1.1068 (5)0.5314 (2)0.0220
H20.2053 (3)1.0688 (5)0.3314 (2)0.0218
H10.1053 (3)0.4899 (5)0.4834 (3)0.0200
O50.22401 (11)1.0900 (3)0.09239 (10)0.0075
C50.16363 (9)1.0948 (2)0.00459 (8)0.0043
O60.09486 (10)0.9256 (3)0.01774 (10)0.0066
C60.18084 (8)1.3412 (2)0.06700 (8)0.0041
N10.12404 (6)1.3033 (2)0.17391 (6)0.0060
H410.1348 (3)1.4678 (6)0.2256 (2)0.0206
H420.1613 (3)1.1467 (6)0.2250 (2)0.0214
H430.0294 (2)1.2663 (6)0.1498 (2)0.0200
C70.31497 (9)1.4413 (2)0.10135 (8)0.0053
C80.40380 (9)1.2666 (2)0.18219 (8)0.0048
C90.41924 (9)1.2907 (2)0.30587 (8)0.0064
C100.49976 (10)1.1277 (3)0.38181 (9)0.0071
C110.56617 (9)0.9395 (3)0.33456 (8)0.0068
C120.55255 (9)0.9154 (3)0.21131 (9)0.0074
C130.47136 (9)1.0775 (2)0.13570 (9)0.0062
H130.4592 (3)1.0570 (6)0.0392 (2)0.0217
H120.6056 (3)0.7704 (6)0.1741 (3)0.0242
H110.6289 (3)0.8129 (7)0.3939 (2)0.0250
H100.5115 (3)1.1508 (7)0.4775 (2)0.0255
H90.3696 (3)1.4408 (6)0.3429 (2)0.0225
H710.3114 (3)1.6287 (5)0.1434 (2)0.0199
H720.3472 (2)1.4738 (6)0.0173 (2)0.0192
H60.1255 (2)1.4865 (5)0.0116 (2)0.0158
H50.1928 (2)0.9300 (6)0.1457 (2)0.0185
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0087 (4)0.0063 (4)0.0040 (4)0.0018 (3)0.0020 (3)0.0013 (3)
C10.0059 (3)0.0047 (3)0.0043 (3)0.0003 (2)0.0017 (3)0.0008 (2)
O30.0090 (4)0.0078 (4)0.0042 (4)0.0015 (3)0.0014 (4)0.0015 (3)
C20.0077 (3)0.0054 (3)0.0054 (3)0.0010 (3)0.0020 (3)0.0006 (3)
C30.0093 (4)0.0048 (3)0.0047 (3)0.0018 (3)0.0017 (3)0.0006 (3)
C40.0060 (3)0.0062 (3)0.0036 (3)0.0002 (3)0.0018 (3)0.0004 (3)
O20.0114 (4)0.0057 (3)0.0053 (4)0.0017 (3)0.0020 (4)0.0016 (3)
O40.0111 (4)0.0072 (4)0.0048 (4)0.0007 (3)0.0019 (3)0.0001 (3)
H30.0347 (13)0.0136 (8)0.0181 (9)0.0091 (8)0.0061 (10)0.0017 (7)
H20.0375 (14)0.0145 (8)0.0142 (8)0.0080 (9)0.0070 (9)0.0063 (7)
H10.0220 (10)0.0150 (8)0.0229 (10)0.0033 (7)0.0043 (9)0.0007 (7)
O50.0090 (4)0.0086 (4)0.0054 (4)0.0031 (3)0.0022 (4)0.0015 (3)
C50.0049 (3)0.0044 (3)0.0038 (3)0.0005 (2)0.0012 (3)0.0002 (2)
O60.0070 (4)0.0063 (3)0.0065 (4)0.0025 (3)0.0015 (3)0.0014 (3)
C60.0040 (3)0.0044 (3)0.0036 (3)0.0002 (2)0.0002 (3)0.0004 (2)
N10.0050 (2)0.0079 (2)0.0052 (2)0.00027 (19)0.0013 (2)0.00171 (19)
H410.0233 (11)0.0191 (9)0.0201 (9)0.0018 (8)0.0058 (9)0.0107 (8)
H420.0258 (11)0.0214 (9)0.0172 (9)0.0057 (8)0.0048 (9)0.0057 (8)
H430.0108 (8)0.0277 (11)0.0226 (10)0.0031 (7)0.0061 (8)0.0034 (8)
C70.0041 (3)0.0052 (3)0.0065 (3)0.0001 (2)0.0006 (3)0.0003 (3)
C80.0046 (3)0.0056 (3)0.0043 (3)0.0004 (2)0.0011 (3)0.0003 (2)
C90.0068 (4)0.0075 (3)0.0047 (3)0.0017 (3)0.0005 (3)0.0006 (3)
C100.0072 (3)0.0089 (3)0.0050 (3)0.0025 (3)0.0010 (3)0.0005 (3)
C110.0058 (3)0.0085 (3)0.0060 (3)0.0025 (3)0.0013 (3)0.0009 (3)
C120.0075 (3)0.0083 (3)0.0062 (3)0.0028 (3)0.0011 (3)0.0000 (3)
C130.0067 (3)0.0076 (3)0.0050 (3)0.0019 (3)0.0024 (3)0.0002 (2)
H130.0258 (12)0.0322 (12)0.0070 (7)0.0086 (9)0.0027 (8)0.0007 (7)
H120.0284 (12)0.0248 (11)0.0201 (10)0.0122 (9)0.0066 (10)0.0036 (8)
H110.0253 (11)0.0282 (11)0.0206 (10)0.0140 (10)0.0021 (9)0.0055 (9)
H100.0320 (13)0.0326 (13)0.0111 (8)0.0103 (10)0.0022 (9)0.0010 (8)
H90.0259 (11)0.0241 (10)0.0181 (9)0.0104 (9)0.0058 (9)0.0040 (8)
H710.0206 (10)0.0124 (8)0.0248 (10)0.0006 (7)0.0002 (9)0.0037 (8)
H720.0178 (9)0.0256 (11)0.0158 (9)0.0006 (8)0.0072 (8)0.0055 (8)
H60.0146 (8)0.0139 (8)0.0180 (9)0.0039 (6)0.0009 (8)0.0035 (7)
H50.0199 (9)0.0188 (9)0.0185 (9)0.0025 (8)0.0081 (8)0.0045 (8)
Geometric parameters (Å, º) top
O1—C11.2748 (13)N1—H411.038 (2)
O1—H11.209 (3)N1—H421.041 (3)
C1—O31.2507 (14)N1—H431.032 (2)
C1—C21.4981 (14)C7—C81.5089 (13)
C2—C31.3427 (14)C7—H711.096 (3)
C2—H21.087 (2)C7—H721.100 (3)
C3—C41.4926 (13)C8—C91.3971 (13)
C3—H31.084 (3)C8—C131.3999 (14)
C4—O21.2891 (14)C9—C101.3973 (13)
C4—O41.2450 (15)C9—H91.087 (3)
O2—H11.208 (3)C10—C111.3933 (15)
O5—C51.3051 (17)C10—H101.084 (3)
O5—H51.053 (3)C11—C121.3940 (14)
C5—O61.2195 (15)C11—H111.088 (3)
C5—C61.5195 (13)C12—C131.3962 (13)
C6—N11.4890 (12)C12—H121.090 (3)
C6—C71.5304 (13)C13—H131.091 (3)
C6—H61.092 (2)
C1—O1—H1111.03 (16)C6—N1—H43111.13 (17)
O1—C1—O3121.54 (11)H41—N1—H43107.6 (2)
O1—C1—C2120.94 (10)H42—N1—H43105.1 (2)
O3—C1—C2117.51 (9)C6—C7—C8114.56 (8)
C1—C2—C3129.82 (8)C6—C7—H71107.72 (16)
C1—C2—H2113.08 (17)C8—C7—H71110.31 (15)
C3—C2—H2117.02 (16)C6—C7—H72106.39 (16)
C2—C3—C4129.96 (9)C8—C7—H72110.64 (16)
C2—C3—H3117.65 (16)H71—C7—H72106.9 (2)
C4—C3—H3112.39 (16)C7—C8—C9120.05 (8)
C3—C4—O2120.60 (10)C7—C8—C13121.20 (8)
C3—C4—O4118.35 (10)C9—C8—C13118.75 (8)
O2—C4—O4121.02 (10)C8—C9—C10120.67 (9)
C4—O2—H1110.85 (15)C8—C9—H9119.36 (16)
O2—H1—O1176.0 (3)C10—C9—H9119.95 (16)
C5—O5—H5107.88 (17)C9—C10—C11120.09 (9)
O5—C5—O6124.86 (10)C9—C10—H10119.66 (19)
O5—C5—C6113.79 (9)C11—C10—H10120.25 (18)
O6—C5—C6121.28 (10)C10—C11—C12119.76 (8)
C5—C6—N1107.60 (7)C10—C11—H11119.97 (18)
C5—C6—C7116.06 (8)C12—C11—H11120.27 (18)
N1—C6—C7111.47 (7)C11—C12—C13119.99 (9)
C5—C6—H6106.44 (15)C11—C12—H12119.90 (17)
N1—C6—H6107.28 (17)C13—C12—H12120.11 (17)
C7—C6—H6107.56 (15)C8—C13—C12120.74 (9)
C6—N1—H41109.83 (18)C8—C13—H13119.05 (16)
C6—N1—H42112.73 (18)C12—C13—H13120.21 (17)
H41—N1—H42110.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i1.0842.4013.2404 (15)133.1 (2)
C2—H2···O1i1.0872.4783.1705 (15)120.4 (2)
N1—H41···C4ii1.0382.3903.3846 (15)160.0 (2)
N1—H41···O2ii1.0382.2182.9763 (15)128.4 (2)
N1—H41···O4ii1.0381.9522.9723 (15)166.9 (3)
N1—H42···O4iii1.0411.9762.9803 (15)161.2 (3)
N1—H43···O3iv1.0322.1002.9978 (15)144.0 (2)
N1—H43···O6iv1.0322.2762.9753 (15)123.7 (2)
C12—H12···O5v1.0902.4293.4633 (15)157.8 (3)
C6—H6···O6i1.0922.3253.2161 (15)137.46 (18)
O5—H5···C11.0532.3983.3949 (15)157.6 (2)
O5—H5···O31.0531.4752.5231 (15)173.3 (3)
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z+1; (iii) x, y, z+1; (iv) x, y+1/2, z; (v) x+1, y1/2, z.
 

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