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The novel polar material 2-amino-3-nitropyridinium hydrogen sulfate, C5H6N3O2(HSO4) (abbreviated as 2A3NP-HS), was obtained and structurally characterized by means of single-crystal X-ray diffraction. At room temperature, 2A3NP-HS crystallizes as a non-centrosymmetric disordered phase (I) in the orthorhombic Pna21 space group. On cooling below 298 K, 2A3NP-HS undergoes a reversible phase transition to phase (II) with the monoclinic non-centrosymmetric P21 space group. This transition might be classified as an `order–disorder' type. The structural details in both phases are analysed. Additionally, for phase (I), in the 304–365 K temperature range, diffuse scattering was found to be present in the form of elongated streaks parallel to the a* direction. This can be unravelled when implementing a short-range order affecting anionic cationic ribbons occurring in the structure, with correlations acting both in the a-direction and in the bc-plane. The results of Monte Carlo simulations, adapting a two-dimensional Ising-type model, reveal the formation of domains, which are b-elongated and thin along a. Locally, the stacking of the ribbons in the domains reflects the ordered arrangement observed in the low-temperature monoclinic phase (II).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617001524/wf5131sup1.cif
Contains datablocks I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617001524/wf5131Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617001524/wf5131IIsup3.hkl
Contains datablock II

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617001524/wf5131sup4.pdf
Supporting figures and tables

CCDC references: 1530073; 1530074

Computing details top

For both compounds, data collection: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015); cell refinement: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015); data reduction: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015). Program(s) used to solve structure: SHELXS (Sheldrick, 2008) for (I); olex2.solve (Bourhis et al., 2015) for (II). For both compounds, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Diamond (Brandenburg, 1997); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(I) top
Crystal data top
C5H6N3O2·HO4SDx = 1.755 Mg m3
Mr = 237.20Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 2457 reflections
a = 17.891 (5) Åθ = 2.9–25.8°
b = 4.586 (3) ŵ = 0.38 mm1
c = 10.941 (4) ÅT = 304 K
V = 897.7 (7) Å3Block, yellow
Z = 40.28 × 0.21 × 0.13 mm
F(000) = 488
Data collection top
Xcalibur, Atlas
diffractometer
1951 independent reflections
Graphite monochromator1528 reflections with I > 2σ(I)
Detector resolution: 10.6249 pixels mm-1Rint = 0.022
ω scansθmax = 29.6°, θmin = 2.9°
Absorption correction: analytical
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
h = 2222
Tmin = 0.918, Tmax = 0.958k = 64
5597 measured reflectionsl = 1413
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0372P)2 + 0.1468P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.038(Δ/σ)max < 0.001
wR(F2) = 0.088Δρmax = 0.19 e Å3
S = 1.07Δρmin = 0.25 e Å3
1951 reflectionsExtinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
196 parametersExtinction coefficient: 0.0065 (19)
24 restraintsAbsolute structure: Flack x determined using 525 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (4)
Hydrogen site location: inferred from neighbouring sites
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N20.4310 (6)0.272 (2)0.2309 (8)0.061 (2)0.536 (13)
H2A0.46630.15040.24630.073*0.536 (13)
H2B0.41520.29370.15720.073*0.536 (13)
C30.3431 (5)0.626 (2)0.3148 (9)0.042 (3)*0.536 (13)
C20.4015 (6)0.425 (2)0.3193 (9)0.036 (3)*0.536 (13)
N10.4299 (4)0.3785 (16)0.4350 (9)0.038 (2)*0.536 (13)
H10.46470.25080.44270.045*0.536 (13)
C60.4069 (5)0.518 (2)0.5366 (7)0.038 (2)*0.536 (13)
H60.43010.47750.61070.046*0.536 (13)
C50.3512 (5)0.716 (2)0.5330 (9)0.048 (2)*0.536 (13)
H50.33570.81370.60300.057*0.536 (13)
C40.3175 (5)0.768 (2)0.4195 (11)0.049 (3)*0.536 (13)
H40.27780.89800.41390.059*0.536 (13)
N30.3044 (10)0.701 (5)0.2025 (15)0.078 (5)0.536 (13)
O110.3179 (8)0.537 (3)0.1147 (10)0.111 (4)0.536 (13)
O120.2643 (8)0.905 (4)0.2015 (19)0.142 (10)0.536 (13)
S10.58544 (5)0.13483 (17)0.37503 (13)0.0513 (3)
O10.65726 (14)0.0499 (5)0.3612 (3)0.0618 (8)
H1B0.64670.22340.36680.093*
O20.5421 (11)0.002 (4)0.4850 (18)0.052 (3)0.536 (13)
O40.6205 (4)0.4103 (12)0.4243 (9)0.063 (2)0.536 (13)
O4A0.6018 (5)0.4265 (14)0.3360 (11)0.067 (3)0.464 (13)
N2A0.4101 (6)0.363 (2)0.1957 (9)0.050 (3)0.464 (13)
H2AA0.44640.24070.19050.060*0.464 (13)
H2AB0.38680.41760.13090.060*0.464 (13)
C3A0.3346 (5)0.672 (2)0.3374 (9)0.035 (3)*0.464 (13)
C2A0.3900 (7)0.468 (3)0.3041 (9)0.046 (4)*0.464 (13)
N1A0.4320 (4)0.3612 (19)0.3985 (11)0.048 (3)*0.464 (13)
H1A0.46710.23940.38210.057*0.464 (13)
C6A0.4209 (7)0.438 (3)0.5161 (12)0.056 (3)*0.464 (13)
H6A0.45100.35970.57720.067*0.464 (13)
C5A0.3657 (8)0.631 (3)0.5456 (10)0.057 (3)*0.464 (13)
H5A0.35640.67770.62680.069*0.464 (13)
C4A0.3246 (6)0.752 (2)0.4556 (12)0.046 (3)*0.464 (13)
H4A0.28900.89210.47490.056*0.464 (13)
N3A0.2895 (9)0.795 (4)0.2372 (14)0.050 (3)0.464 (13)
O11A0.2881 (9)0.668 (3)0.1350 (11)0.076 (3)0.464 (13)
O12A0.2562 (7)1.014 (3)0.2589 (12)0.076 (4)0.464 (13)
O30.5491 (7)0.147 (3)0.2744 (9)0.068 (3)0.536 (13)
O3A0.5333 (8)0.022 (3)0.2650 (12)0.068 (3)0.464 (13)
O2A0.5520 (14)0.083 (5)0.476 (2)0.066 (5)0.464 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.067 (6)0.073 (7)0.042 (5)0.002 (4)0.008 (4)0.006 (4)
N30.056 (8)0.102 (14)0.075 (12)0.020 (8)0.012 (8)0.032 (10)
O110.124 (11)0.129 (10)0.081 (7)0.027 (7)0.057 (7)0.037 (6)
O120.090 (8)0.18 (2)0.159 (18)0.043 (9)0.030 (10)0.094 (17)
S10.0538 (5)0.0345 (4)0.0655 (6)0.0006 (4)0.0145 (6)0.0000 (6)
O10.0487 (14)0.0444 (11)0.092 (2)0.0007 (10)0.0147 (15)0.0014 (19)
O20.060 (5)0.055 (8)0.041 (6)0.023 (5)0.016 (4)0.000 (5)
O40.092 (5)0.036 (3)0.062 (5)0.011 (3)0.005 (4)0.004 (3)
O4A0.083 (5)0.032 (3)0.084 (8)0.004 (3)0.010 (4)0.003 (4)
N2A0.049 (5)0.055 (7)0.045 (6)0.015 (4)0.004 (4)0.004 (5)
N3A0.044 (7)0.056 (7)0.051 (6)0.003 (5)0.004 (5)0.006 (6)
O11A0.085 (8)0.090 (9)0.054 (6)0.016 (6)0.018 (5)0.007 (6)
O12A0.052 (5)0.059 (5)0.117 (9)0.017 (4)0.009 (5)0.000 (5)
O30.081 (6)0.082 (8)0.042 (4)0.006 (5)0.020 (4)0.006 (5)
O3A0.074 (6)0.062 (8)0.068 (6)0.016 (5)0.025 (4)0.002 (5)
O2A0.078 (10)0.068 (12)0.051 (6)0.001 (7)0.035 (6)0.013 (8)
Geometric parameters (Å, º) top
N2—H2A0.8600S1—O31.280 (10)
N2—H2B0.8600S1—O3A1.610 (11)
N2—C21.306 (10)S1—O2A1.28 (2)
C3—C21.394 (12)O1—H1B0.8200
C3—C41.395 (12)N2A—H2AA0.8600
C3—N31.452 (13)N2A—H2AB0.8600
C2—N11.381 (11)N2A—C2A1.329 (12)
N1—H10.8600C3A—C2A1.411 (13)
N1—C61.347 (12)C3A—C4A1.356 (13)
C6—H60.9300C3A—N3A1.473 (13)
C6—C51.348 (12)C2A—N1A1.369 (13)
C5—H50.9300N1A—H1A0.8600
C5—C41.400 (12)N1A—C6A1.348 (15)
C4—H40.9300C6A—H6A0.9300
N3—O111.24 (2)C6A—C5A1.364 (15)
N3—O121.18 (2)C5A—H5A0.9300
S1—O11.547 (3)C5A—C4A1.348 (15)
S1—O21.563 (15)C4A—H4A0.9300
S1—O41.510 (6)N3A—O11A1.26 (2)
S1—O4A1.435 (7)N3A—O12A1.193 (19)
H2A—N2—H2B120.0O3—S1—O2115.3 (9)
C2—N2—H2A120.0O3—S1—O4118.7 (6)
C2—N2—H2B120.0O2A—S1—O1111.8 (13)
C2—C3—C4121.7 (8)O2A—S1—O4A121.8 (11)
C2—C3—N3122.9 (13)O2A—S1—O3A108.3 (12)
C4—C3—N3115.4 (12)S1—O1—H1B109.5
N2—C2—C3129.2 (10)H2AA—N2A—H2AB120.0
N2—C2—N1116.6 (10)C2A—N2A—H2AA120.0
N1—C2—C3114.2 (7)C2A—N2A—H2AB120.0
C2—N1—H1117.6C2A—C3A—N3A116.5 (10)
C6—N1—C2124.8 (7)C4A—C3A—C2A121.2 (9)
C6—N1—H1117.6C4A—C3A—N3A122.3 (12)
N1—C6—H6119.3N2A—C2A—C3A131.4 (11)
N1—C6—C5121.4 (7)N2A—C2A—N1A113.3 (10)
C5—C6—H6119.3N1A—C2A—C3A115.3 (8)
C6—C5—H5121.4C2A—N1A—H1A118.4
C6—C5—C4117.3 (7)C6A—N1A—C2A123.1 (9)
C4—C5—H5121.4C6A—N1A—H1A118.4
C3—C4—C5120.5 (8)N1A—C6A—H6A120.0
C3—C4—H4119.7N1A—C6A—C5A120.1 (9)
C5—C4—H4119.7C5A—C6A—H6A120.0
O11—N3—C3114.8 (17)C6A—C5A—H5A120.3
O12—N3—C3119 (2)C4A—C5A—C6A119.3 (10)
O12—N3—O11126.2 (15)C4A—C5A—H5A120.3
O1—S1—O2105.6 (9)C3A—C4A—H4A119.6
O1—S1—O3A103.4 (6)C5A—C4A—C3A120.9 (10)
O4—S1—O198.5 (3)C5A—C4A—H4A119.6
O4—S1—O2105.5 (7)O11A—N3A—C3A119.7 (14)
O4A—S1—O1108.2 (3)O12A—N3A—C3A116.6 (13)
O4A—S1—O3A101.3 (6)O12A—N3A—O11A123.7 (12)
O3—S1—O1111.3 (6)
N2—C2—N1—C6179.2 (8)N2A—C2A—N1A—C6A179.8 (11)
C3—C2—N1—C62.6 (13)C3A—C2A—N1A—C6A1.5 (15)
C2—C3—C4—C51.2 (13)C2A—C3A—C4A—C5A2.4 (16)
C2—C3—N3—O1112.1 (19)C2A—C3A—N3A—O11A17 (2)
C2—C3—N3—O12167.6 (13)C2A—C3A—N3A—O12A162.1 (14)
C2—N1—C6—C51.8 (13)C2A—N1A—C6A—C5A0.0 (17)
N1—C6—C5—C40.6 (12)N1A—C6A—C5A—C4A2.8 (17)
C6—C5—C4—C32.0 (12)C6A—C5A—C4A—C3A4.0 (17)
C4—C3—C2—N2179.0 (10)C4A—C3A—C2A—N2A178.7 (12)
C4—C3—C2—N11.1 (12)C4A—C3A—C2A—N1A0.3 (15)
C4—C3—N3—O11167.6 (12)C4A—C3A—N3A—O11A163.4 (15)
C4—C3—N3—O1212.8 (19)C4A—C3A—N3A—O12A17 (2)
N3—C3—C2—N20.6 (17)N3A—C3A—C2A—N2A0 (2)
N3—C3—C2—N1178.6 (11)N3A—C3A—C2A—N1A178.8 (11)
N3—C3—C4—C5179.2 (10)N3A—C3A—C4A—C5A178.5 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.862.042.897 (13)177
N2—H2B···O110.862.122.682 (14)122
N2—H2B···O2i0.862.443.01 (2)124
N1—H1···O20.861.852.704 (15)171
C6—H6···O3ii0.932.373.207 (13)149
O1—H1B···O4iii0.821.852.652 (7)164
O1—H1B···O4Aiii0.821.832.612 (7)160
N2A—H2AA···O3A0.862.132.923 (12)154
N2A—H2AB···O11A0.862.112.676 (17)123
N1A—H1A···O3A0.862.122.916 (18)155
N1A—H1A···O2A0.862.353.08 (2)142
Symmetry codes: (i) x+1, y, z1/2; (ii) x+1, y, z+1/2; (iii) x, y+1, z.
(II) top
Crystal data top
C5H6N3O2·HO4SF(000) = 976
Mr = 237.20Dx = 1.793 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.051 (3) ÅCell parameters from 26437 reflections
b = 10.968 (4) Åθ = 2.4–29.5°
c = 18.268 (5) ŵ = 0.39 mm1
β = 104.35 (3)°T = 100 K
V = 1756.9 (10) Å3Block, yellow
Z = 80.56 × 0.41 × 0.14 mm
Data collection top
Xcalibur, Atlas
diffractometer
8812 independent reflections
Graphite monochromator8592 reflections with I > 2σ(I)
Detector resolution: 10.6249 pixels mm-1Rint = 0.020
ω scansθmax = 29.5°, θmin = 1.9°
Absorption correction: analytical
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
h = 1212
Tmin = 0.967, Tmax = 1.000k = 1414
46250 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.052 w = 1/[σ2(Fo2) + (0.031P)2 + 0.172P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
8812 reflectionsΔρmax = 0.20 e Å3
546 parametersΔρmin = 0.42 e Å3
1 restraintAbsolute structure: Twinning involves inversion, so Flack parameter cannot be determined
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.4029 (3)0.7320 (2)0.43391 (13)0.0143 (5)
H110.35650.73910.47070.017*
C120.4119 (4)0.6185 (3)0.40504 (14)0.0146 (7)
N120.3488 (3)0.5275 (2)0.43339 (13)0.0183 (6)
H12A0.30280.54110.46980.022*
H12B0.35270.45310.41590.022*
C130.4882 (4)0.6143 (3)0.34551 (15)0.0151 (7)
N130.5057 (3)0.4981 (3)0.30902 (15)0.0236 (6)
O10.4339 (3)0.4088 (2)0.32156 (13)0.0289 (6)
O20.5921 (3)0.4972 (3)0.26634 (13)0.0372 (7)
C140.5440 (4)0.7185 (3)0.31982 (17)0.0192 (8)
H140.59230.71380.27930.023*
C150.5298 (4)0.8308 (3)0.35321 (17)0.0201 (7)
H150.56850.90310.33620.024*
C160.4596 (4)0.8342 (3)0.41033 (17)0.0167 (7)
H160.45000.90970.43420.020*
N210.8949 (3)0.6883 (2)0.43557 (13)0.0161 (5)
H210.84970.66970.47150.019*
C220.9303 (4)0.5952 (3)0.39390 (15)0.0129 (6)
N220.8945 (3)0.4841 (2)0.41067 (13)0.0170 (5)
H22A0.84940.47250.44760.020*
H22B0.91560.42140.38490.020*
C231.0027 (4)0.6305 (3)0.33708 (16)0.0135 (6)
N231.0514 (3)0.5383 (2)0.29027 (13)0.0152 (5)
O30.9927 (3)0.4364 (2)0.28644 (13)0.0245 (5)
O41.1499 (2)0.5676 (2)0.25813 (11)0.0217 (5)
C241.0329 (3)0.7516 (3)0.32514 (16)0.0179 (8)
H241.08110.77330.28630.021*
C250.9923 (4)0.8417 (3)0.37034 (17)0.0190 (7)
H251.01180.92530.36260.023*
C260.9241 (4)0.8077 (3)0.42591 (16)0.0196 (7)
H260.89700.86770.45780.024*
N310.0351 (3)0.7304 (2)0.06554 (13)0.0132 (5)
H310.11770.73800.02840.016*
C320.0024 (4)0.6171 (3)0.09381 (14)0.0126 (6)
N320.0903 (3)0.5257 (2)0.06450 (13)0.0169 (5)
H32A0.17250.54000.02810.020*
H32B0.06940.45100.08150.020*
C330.1389 (4)0.6109 (3)0.15302 (16)0.0177 (7)
N330.1927 (3)0.4941 (3)0.18829 (15)0.0232 (6)
O50.1053 (3)0.4059 (2)0.17510 (12)0.0285 (5)
O60.3224 (3)0.4902 (3)0.22958 (13)0.0363 (7)
C340.2213 (4)0.7136 (3)0.17920 (18)0.0212 (8)
H340.31080.70690.21920.025*
C350.1762 (4)0.8276 (3)0.14818 (17)0.0216 (7)
H350.23310.89900.16610.026*
C360.0453 (4)0.8325 (3)0.09027 (17)0.0173 (7)
H360.01140.90870.06750.021*
N410.5341 (3)0.6876 (3)0.06634 (13)0.0155 (5)
H410.61500.67020.02990.019*
C420.4593 (3)0.5934 (3)0.10763 (14)0.0136 (6)
N420.5113 (3)0.4821 (2)0.09082 (13)0.0178 (5)
H42A0.59280.47030.05360.021*
H42B0.46470.41960.11680.021*
C430.3276 (4)0.6279 (3)0.16478 (15)0.0148 (6)
N430.2358 (3)0.5343 (2)0.21171 (13)0.0160 (6)
O70.2930 (3)0.4339 (2)0.21597 (12)0.0249 (5)
O80.1058 (2)0.5623 (2)0.24486 (11)0.0229 (5)
C440.2841 (4)0.7474 (3)0.17639 (17)0.0186 (7)
H440.19620.76770.21500.022*
C450.3675 (5)0.8394 (3)0.13211 (17)0.0213 (8)
H450.33810.92250.13970.026*
C460.4938 (4)0.8056 (3)0.07702 (18)0.0196 (7)
H460.55340.86630.04610.023*
S10.21518 (10)0.68409 (8)0.59158 (5)0.01190 (19)
O110.3470 (3)0.6661 (2)0.66437 (11)0.0182 (5)
H11A0.43110.66510.65260.027*
O140.0876 (2)0.72424 (18)0.62073 (12)0.0183 (5)
O120.2639 (3)0.7788 (2)0.54631 (11)0.0159 (5)
O130.1896 (2)0.5679 (2)0.55224 (12)0.0190 (5)
S20.71331 (11)0.65600 (7)0.58390 (5)0.0126 (2)
O210.8358 (3)0.6461 (3)0.66030 (12)0.0179 (5)
H21A0.91870.67490.65530.027*
O240.5732 (2)0.6230 (2)0.60385 (12)0.0202 (5)
O220.7174 (3)0.7790 (2)0.55594 (13)0.0223 (5)
O230.7532 (2)0.5672 (2)0.53231 (12)0.0210 (5)
S30.37920 (11)0.68151 (8)0.09352 (4)0.01170 (19)
O310.3135 (3)0.6681 (2)0.16461 (11)0.0179 (6)
H31A0.22040.65060.15090.027*
O320.2901 (3)0.7764 (2)0.04586 (11)0.0167 (5)
O330.3659 (3)0.5655 (2)0.05501 (12)0.0207 (5)
O340.5358 (2)0.72037 (18)0.12587 (11)0.0180 (5)
S40.86551 (10)0.65476 (8)0.08034 (4)0.0128 (2)
O410.8217 (3)0.6433 (3)0.15829 (11)0.0197 (5)
H41A0.72690.65070.15140.030*
O420.8268 (3)0.7776 (2)0.05264 (12)0.0227 (5)
O430.7740 (2)0.5651 (2)0.02974 (11)0.0216 (5)
O441.0261 (2)0.6255 (2)0.09767 (11)0.0181 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0165 (13)0.0145 (13)0.0121 (11)0.0014 (12)0.0039 (10)0.0007 (9)
C120.0155 (15)0.0137 (16)0.0121 (12)0.0016 (11)0.0014 (11)0.0023 (11)
N120.0241 (14)0.0131 (14)0.0183 (12)0.0002 (10)0.0065 (10)0.0018 (9)
C130.0146 (15)0.0167 (16)0.0130 (12)0.0046 (12)0.0015 (12)0.0020 (11)
N130.0256 (14)0.0266 (16)0.0170 (12)0.0122 (13)0.0018 (11)0.0027 (11)
O10.0356 (13)0.0199 (12)0.0295 (12)0.0053 (11)0.0050 (11)0.0095 (9)
O20.0497 (16)0.0428 (17)0.0248 (12)0.0145 (14)0.0200 (12)0.0053 (11)
C140.0137 (16)0.029 (2)0.0144 (14)0.0013 (13)0.0028 (12)0.0012 (11)
C150.0196 (16)0.0212 (16)0.0174 (14)0.0035 (12)0.0004 (13)0.0078 (12)
C160.0158 (15)0.0108 (15)0.0197 (13)0.0015 (11)0.0027 (13)0.0002 (11)
N210.0189 (13)0.0147 (13)0.0151 (11)0.0007 (11)0.0050 (10)0.0000 (10)
C220.0112 (13)0.0130 (14)0.0136 (12)0.0024 (11)0.0013 (11)0.0006 (10)
N220.0249 (13)0.0112 (13)0.0180 (11)0.0038 (10)0.0113 (10)0.0001 (9)
C230.0152 (13)0.0129 (15)0.0117 (11)0.0001 (12)0.0020 (11)0.0015 (10)
N230.0146 (11)0.0184 (14)0.0121 (11)0.0004 (10)0.0020 (10)0.0034 (9)
O30.0319 (12)0.0170 (12)0.0268 (11)0.0051 (10)0.0115 (10)0.0049 (9)
O40.0181 (10)0.0328 (13)0.0168 (9)0.0007 (9)0.0092 (8)0.0029 (9)
C240.0196 (17)0.0166 (18)0.0158 (13)0.0039 (12)0.0010 (12)0.0079 (12)
C250.0205 (16)0.0104 (13)0.0219 (15)0.0018 (12)0.0027 (13)0.0036 (11)
C260.0206 (15)0.0165 (17)0.0172 (14)0.0030 (13)0.0037 (12)0.0024 (11)
N310.0130 (12)0.0144 (14)0.0122 (11)0.0014 (11)0.0031 (10)0.0002 (9)
C320.0146 (14)0.0132 (16)0.0120 (11)0.0032 (11)0.0069 (11)0.0008 (11)
N320.0203 (13)0.0126 (13)0.0169 (11)0.0001 (10)0.0031 (10)0.0013 (9)
C330.0201 (18)0.0210 (18)0.0136 (12)0.0071 (13)0.0071 (13)0.0023 (12)
N330.0244 (14)0.0288 (16)0.0172 (12)0.0100 (13)0.0066 (11)0.0057 (11)
O50.0368 (13)0.0235 (13)0.0256 (11)0.0091 (11)0.0087 (11)0.0094 (9)
O60.0297 (14)0.0451 (17)0.0277 (12)0.0184 (14)0.0049 (11)0.0054 (11)
C340.0179 (16)0.031 (2)0.0146 (13)0.0041 (14)0.0043 (12)0.0038 (12)
C350.0183 (17)0.0292 (18)0.0172 (14)0.0036 (13)0.0046 (13)0.0069 (13)
C360.0197 (17)0.0159 (16)0.0169 (13)0.0012 (12)0.0056 (13)0.0023 (11)
N410.0152 (12)0.0190 (14)0.0125 (10)0.0001 (12)0.0038 (10)0.0011 (11)
C420.0137 (15)0.0161 (14)0.0122 (12)0.0016 (12)0.0056 (11)0.0026 (11)
N420.0175 (12)0.0175 (13)0.0152 (11)0.0025 (10)0.0016 (10)0.0002 (9)
C430.0119 (14)0.0213 (16)0.0106 (11)0.0023 (13)0.0018 (11)0.0007 (11)
N430.0184 (13)0.0172 (14)0.0111 (11)0.0031 (11)0.0013 (10)0.0023 (10)
O70.0259 (12)0.0205 (12)0.0232 (11)0.0009 (9)0.0038 (10)0.0080 (9)
O80.0156 (11)0.0341 (14)0.0160 (9)0.0022 (9)0.0016 (8)0.0017 (9)
C440.0203 (18)0.0218 (18)0.0148 (13)0.0056 (13)0.0065 (13)0.0023 (12)
C450.038 (2)0.0127 (14)0.0157 (14)0.0037 (14)0.0119 (15)0.0022 (11)
C460.0239 (16)0.0158 (16)0.0221 (15)0.0047 (14)0.0114 (14)0.0026 (12)
S10.0120 (4)0.0095 (5)0.0148 (4)0.0005 (3)0.0046 (3)0.0005 (3)
O110.0147 (11)0.0271 (14)0.0141 (8)0.0034 (9)0.0060 (9)0.0013 (8)
O140.0158 (9)0.0147 (11)0.0271 (11)0.0016 (8)0.0107 (8)0.0041 (8)
O120.0192 (10)0.0116 (10)0.0196 (9)0.0017 (8)0.0098 (8)0.0024 (8)
O130.0236 (11)0.0109 (11)0.0229 (11)0.0025 (9)0.0064 (9)0.0037 (9)
S20.0116 (4)0.0117 (5)0.0146 (3)0.0015 (3)0.0033 (3)0.0014 (3)
O210.0115 (11)0.0254 (12)0.0162 (9)0.0020 (10)0.0021 (9)0.0050 (8)
O240.0122 (9)0.0233 (13)0.0264 (11)0.0003 (8)0.0075 (8)0.0039 (8)
O220.0245 (12)0.0140 (11)0.0268 (11)0.0013 (10)0.0035 (10)0.0071 (9)
O230.0265 (11)0.0170 (11)0.0232 (11)0.0034 (9)0.0134 (9)0.0035 (8)
S30.0105 (3)0.0118 (5)0.0129 (3)0.0004 (3)0.0031 (3)0.0005 (3)
O310.0122 (11)0.0302 (15)0.0122 (8)0.0001 (9)0.0048 (9)0.0020 (8)
O320.0156 (10)0.0136 (11)0.0186 (9)0.0023 (9)0.0001 (8)0.0038 (8)
O330.0208 (11)0.0162 (12)0.0234 (11)0.0024 (9)0.0024 (9)0.0048 (9)
O340.0129 (9)0.0177 (12)0.0237 (10)0.0005 (8)0.0052 (8)0.0020 (8)
S40.0100 (4)0.0156 (6)0.0128 (3)0.0005 (3)0.0031 (3)0.0018 (3)
O410.0159 (11)0.0293 (12)0.0142 (8)0.0058 (11)0.0042 (9)0.0042 (8)
O420.0242 (13)0.0168 (12)0.0284 (11)0.0039 (10)0.0093 (10)0.0075 (9)
O430.0172 (11)0.0219 (12)0.0230 (10)0.0023 (9)0.0001 (8)0.0051 (9)
O440.0116 (9)0.0241 (12)0.0185 (10)0.0001 (8)0.0035 (7)0.0022 (8)
Geometric parameters (Å, º) top
N11—H110.8800N33—O61.229 (4)
N11—C121.362 (4)C34—H340.9500
N11—C161.347 (4)C34—C351.392 (5)
C12—N121.319 (4)C35—H350.9500
C12—C131.426 (4)C35—C361.380 (4)
N12—H12A0.8800C36—H360.9500
N12—H12B0.8800N41—H410.8800
C13—N131.465 (4)N41—C421.357 (4)
C13—C141.378 (5)N41—C461.346 (4)
N13—O11.227 (4)C42—N421.317 (4)
N13—O21.233 (4)C42—C431.427 (4)
C14—H140.9500N42—H42A0.8800
C14—C151.394 (5)N42—H42B0.8800
C15—H150.9500C43—N431.458 (4)
C15—C161.350 (4)C43—C441.370 (5)
C16—H160.9500N43—O71.228 (3)
N21—H210.8800N43—O81.221 (3)
N21—C221.358 (4)C44—H440.9500
N21—C261.357 (4)C44—C451.393 (5)
C22—N221.317 (4)C45—H450.9500
C22—C231.412 (4)C45—C461.373 (5)
N22—H22A0.8800C46—H460.9500
N22—H22B0.8800S1—O111.563 (2)
C23—N231.461 (4)S1—O141.454 (2)
C23—C241.385 (4)S1—O121.462 (2)
N23—O31.232 (3)S1—O131.453 (2)
N23—O41.226 (3)O11—H11A0.8400
C24—H240.9500S2—O211.556 (2)
C24—C251.394 (5)S2—O241.450 (2)
C25—H250.9500S2—O221.446 (3)
C25—C261.365 (5)S2—O231.461 (2)
C26—H260.9500O21—H21A0.8400
N31—H310.8800S3—O311.563 (2)
N31—C321.357 (4)S3—O321.464 (2)
N31—C361.351 (4)S3—O331.444 (2)
C32—N321.331 (4)S3—O341.458 (2)
C32—C331.427 (4)O31—H31A0.8400
N32—H32A0.8800S4—O411.575 (2)
N32—H32B0.8800S4—O421.451 (3)
C33—N331.462 (4)S4—O431.459 (2)
C33—C341.370 (5)S4—O441.445 (2)
N33—O51.235 (4)O41—H41A0.8400
C12—N11—H11117.5O6—N33—O5124.1 (3)
C16—N11—H11117.5C33—C34—H34119.4
C16—N11—C12124.9 (3)C33—C34—C35121.1 (3)
N11—C12—C13114.3 (3)C35—C34—H34119.4
N12—C12—N11117.8 (3)C34—C35—H35121.4
N12—C12—C13127.9 (3)C36—C35—C34117.2 (3)
C12—N12—H12A120.0C36—C35—H35121.4
C12—N12—H12B120.0N31—C36—C35120.9 (3)
H12A—N12—H12B120.0N31—C36—H36119.6
C12—C13—N13120.1 (3)C35—C36—H36119.6
C14—C13—C12121.4 (3)C42—N41—H41117.6
C14—C13—N13118.5 (3)C46—N41—H41117.6
O1—N13—C13119.2 (3)C46—N41—C42124.9 (3)
O1—N13—O2124.0 (3)N41—C42—C43114.6 (3)
O2—N13—C13116.8 (3)N42—C42—N41118.4 (3)
C13—C14—H14119.9N42—C42—C43127.0 (3)
C13—C14—C15120.1 (3)C42—N42—H42A120.0
C15—C14—H14119.9C42—N42—H42B120.0
C14—C15—H15120.8H42A—N42—H42B120.0
C16—C15—C14118.3 (3)C42—C43—N43119.7 (3)
C16—C15—H15120.8C44—C43—C42121.5 (3)
N11—C16—C15120.9 (3)C44—C43—N43118.8 (3)
N11—C16—H16119.5O7—N43—C43118.7 (3)
C15—C16—H16119.5O8—N43—C43117.0 (3)
C22—N21—H21117.5O8—N43—O7124.3 (3)
C26—N21—H21117.5C43—C44—H44119.7
C26—N21—C22124.9 (3)C43—C44—C45120.6 (3)
N21—C22—C23115.0 (3)C45—C44—H44119.7
N22—C22—N21117.3 (3)C44—C45—H45121.2
N22—C22—C23127.6 (3)C46—C45—C44117.6 (3)
C22—N22—H22A120.0C46—C45—H45121.2
C22—N22—H22B120.0N41—C46—C45120.8 (3)
H22A—N22—H22B120.0N41—C46—H46119.6
C22—C23—N23120.2 (3)C45—C46—H46119.6
C24—C23—C22121.6 (3)O14—S1—O11103.57 (13)
C24—C23—N23118.2 (3)O14—S1—O12111.73 (13)
O3—N23—C23118.2 (3)O12—S1—O11107.26 (14)
O4—N23—C23117.4 (3)O13—S1—O11107.74 (13)
O4—N23—O3124.4 (3)O13—S1—O14113.79 (14)
C23—C24—H24120.2O13—S1—O12112.10 (14)
C23—C24—C25119.7 (3)S1—O11—H11A109.5
C25—C24—H24120.2O24—S2—O21103.32 (14)
C24—C25—H25120.6O24—S2—O23111.54 (14)
C26—C25—C24118.8 (3)O22—S2—O21107.88 (15)
C26—C25—H25120.6O22—S2—O24114.97 (15)
N21—C26—C25119.9 (3)O22—S2—O23111.21 (14)
N21—C26—H26120.0O23—S2—O21107.28 (14)
C25—C26—H26120.0S2—O21—H21A109.5
C32—N31—H31117.7O32—S3—O31107.10 (13)
C36—N31—H31117.7O33—S3—O31108.60 (13)
C36—N31—C32124.7 (3)O33—S3—O32111.66 (13)
N31—C32—C33114.8 (3)O33—S3—O34114.21 (14)
N32—C32—N31117.6 (3)O34—S3—O31102.86 (13)
N32—C32—C33127.6 (3)O34—S3—O32111.74 (14)
C32—N32—H32A120.0S3—O31—H31A109.5
C32—N32—H32B120.0O42—S4—O41107.25 (14)
H32A—N32—H32B120.0O42—S4—O43110.79 (14)
C32—C33—N33120.5 (3)O43—S4—O41106.77 (14)
C34—C33—C32121.3 (3)O44—S4—O41104.43 (14)
C34—C33—N33118.2 (3)O44—S4—O42115.18 (15)
O5—N33—C33118.2 (3)O44—S4—O43111.78 (14)
O6—N33—C33117.7 (3)S4—O41—H41A109.5
N11—C12—C13—N13179.8 (3)N31—C32—C33—N33179.7 (3)
N11—C12—C13—C141.2 (4)N31—C32—C33—C341.4 (4)
C12—N11—C16—C151.2 (4)C32—N31—C36—C350.1 (5)
C12—C13—N13—O111.5 (4)C32—C33—N33—O512.2 (4)
C12—C13—N13—O2169.3 (3)C32—C33—N33—O6168.1 (3)
C12—C13—C14—C151.5 (5)C32—C33—C34—C351.0 (5)
N12—C12—C13—N131.0 (5)N32—C32—C33—N330.8 (5)
N12—C12—C13—C14177.6 (3)N32—C32—C33—C34178.1 (3)
C13—C14—C15—C160.5 (5)C33—C34—C35—C360.1 (5)
N13—C13—C14—C15179.9 (3)N33—C33—C34—C35179.9 (3)
C14—C13—N13—O1167.1 (3)C34—C33—N33—O5166.7 (3)
C14—C13—N13—O212.1 (4)C34—C33—N33—O613.0 (4)
C14—C15—C16—N110.8 (4)C34—C35—C36—N310.4 (4)
C16—N11—C12—N12179.0 (3)C36—N31—C32—N32178.6 (3)
C16—N11—C12—C130.1 (4)C36—N31—C32—C330.9 (4)
N21—C22—C23—N23177.8 (3)N41—C42—C43—N43178.6 (3)
N21—C22—C23—C240.6 (5)N41—C42—C43—C440.8 (4)
C22—N21—C26—C250.8 (5)C42—N41—C46—C451.0 (5)
C22—C23—N23—O319.8 (4)C42—C43—N43—O719.6 (4)
C22—C23—N23—O4159.3 (3)C42—C43—N43—O8160.9 (3)
C22—C23—C24—C250.5 (5)C42—C43—C44—C450.3 (5)
N22—C22—C23—N232.0 (5)N42—C42—C43—N430.1 (5)
N22—C22—C23—C24179.5 (3)N42—C42—C43—C44179.3 (3)
C23—C24—C25—C260.4 (4)C43—C44—C45—C460.0 (4)
N23—C23—C24—C25178.0 (3)N43—C43—C44—C45179.1 (3)
C24—C23—N23—O3161.7 (3)C44—C43—N43—O7161.0 (3)
C24—C23—N23—O419.2 (4)C44—C43—N43—O818.5 (4)
C24—C25—C26—N211.0 (4)C44—C45—C46—N410.4 (5)
C26—N21—C22—N22179.9 (3)C46—N41—C42—N42179.8 (3)
C26—N21—C22—C230.0 (5)C46—N41—C42—C431.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O120.881.842.710 (3)171
N12—H12A···O130.882.042.922 (3)178
N12—H12B···O10.882.092.691 (3)125
N12—H12B···O22i0.882.122.808 (4)135
C16—H16···O24ii0.952.433.186 (4)136
N21—H21···O220.882.483.187 (4)138
N21—H21···O230.881.932.767 (4)157
N22—H22A···O230.882.212.969 (3)144
N22—H22B···O30.882.092.686 (3)124
N22—H22B···O14i0.882.172.919 (3)144
C24—H24···O5iii0.952.553.419 (4)152
C26—H26···O13ii0.952.323.093 (4)138
N31—H31···O320.881.842.719 (3)172
N32—H32A···O330.882.032.912 (3)177
N32—H32B···O50.882.082.678 (3)124
N32—H32B···O42iv0.882.132.816 (4)135
C36—H36···O44iii0.952.443.223 (4)140
N41—H41···O420.882.433.141 (4)138
N41—H41···O430.881.952.777 (4)156
N42—H42A···O32iv0.882.372.875 (3)117
N42—H42A···O430.882.202.955 (3)143
N42—H42B···O70.882.082.678 (3)125
N42—H42B···O34iv0.882.192.950 (3)144
C46—H46···O33iii0.952.323.106 (4)139
O11—H11A···O240.841.802.599 (3)159
O21—H21A···O14v0.841.872.696 (3)166
O31—H31A···O44vi0.841.812.628 (3)165
O41—H41A···O340.841.842.646 (3)160
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+1, y+1/2, z+1; (iii) x+1, y+1/2, z; (iv) x+1, y1/2, z; (v) x+1, y, z; (vi) x1, y, z.
 

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