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
CCDC references: 1530073; 1530074
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).
Crystal data top
C5H6N3O2·HO4S | Dx = 1.755 Mg m−3 |
Mr = 237.20 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 2457 reflections |
a = 17.891 (5) Å | θ = 2.9–25.8° |
b = 4.586 (3) Å | µ = 0.38 mm−1 |
c = 10.941 (4) Å | T = 304 K |
V = 897.7 (7) Å3 | Block, yellow |
Z = 4 | 0.28 × 0.21 × 0.13 mm |
F(000) = 488 | |
Data collection top
Xcalibur, Atlas diffractometer | 1951 independent reflections |
Graphite monochromator | 1528 reflections with I > 2σ(I) |
Detector resolution: 10.6249 pixels mm-1 | Rint = 0.022 |
ω scans | θmax = 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 = −22→22 |
Tmin = 0.918, Tmax = 0.958 | k = −6→4 |
5597 measured reflections | l = −14→13 |
Refinement top
Refinement on F2 | H-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) = 0.088 | Δρmax = 0.19 e Å−3 |
S = 1.07 | Δρmin = −0.25 e Å−3 |
1951 reflections | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
196 parameters | Extinction coefficient: 0.0065 (19) |
24 restraints | Absolute 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 methods | Absolute 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
N2 | 0.4310 (6) | 0.272 (2) | 0.2309 (8) | 0.061 (2) | 0.536 (13) |
H2A | 0.4663 | 0.1504 | 0.2463 | 0.073* | 0.536 (13) |
H2B | 0.4152 | 0.2937 | 0.1572 | 0.073* | 0.536 (13) |
C3 | 0.3431 (5) | 0.626 (2) | 0.3148 (9) | 0.042 (3)* | 0.536 (13) |
C2 | 0.4015 (6) | 0.425 (2) | 0.3193 (9) | 0.036 (3)* | 0.536 (13) |
N1 | 0.4299 (4) | 0.3785 (16) | 0.4350 (9) | 0.038 (2)* | 0.536 (13) |
H1 | 0.4647 | 0.2508 | 0.4427 | 0.045* | 0.536 (13) |
C6 | 0.4069 (5) | 0.518 (2) | 0.5366 (7) | 0.038 (2)* | 0.536 (13) |
H6 | 0.4301 | 0.4775 | 0.6107 | 0.046* | 0.536 (13) |
C5 | 0.3512 (5) | 0.716 (2) | 0.5330 (9) | 0.048 (2)* | 0.536 (13) |
H5 | 0.3357 | 0.8137 | 0.6030 | 0.057* | 0.536 (13) |
C4 | 0.3175 (5) | 0.768 (2) | 0.4195 (11) | 0.049 (3)* | 0.536 (13) |
H4 | 0.2778 | 0.8980 | 0.4139 | 0.059* | 0.536 (13) |
N3 | 0.3044 (10) | 0.701 (5) | 0.2025 (15) | 0.078 (5) | 0.536 (13) |
O11 | 0.3179 (8) | 0.537 (3) | 0.1147 (10) | 0.111 (4) | 0.536 (13) |
O12 | 0.2643 (8) | 0.905 (4) | 0.2015 (19) | 0.142 (10) | 0.536 (13) |
S1 | 0.58544 (5) | −0.13483 (17) | 0.37503 (13) | 0.0513 (3) | |
O1 | 0.65726 (14) | 0.0499 (5) | 0.3612 (3) | 0.0618 (8) | |
H1B | 0.6467 | 0.2234 | 0.3668 | 0.093* | |
O2 | 0.5421 (11) | 0.002 (4) | 0.4850 (18) | 0.052 (3) | 0.536 (13) |
O4 | 0.6205 (4) | −0.4103 (12) | 0.4243 (9) | 0.063 (2) | 0.536 (13) |
O4A | 0.6018 (5) | −0.4265 (14) | 0.3360 (11) | 0.067 (3) | 0.464 (13) |
N2A | 0.4101 (6) | 0.363 (2) | 0.1957 (9) | 0.050 (3) | 0.464 (13) |
H2AA | 0.4464 | 0.2407 | 0.1905 | 0.060* | 0.464 (13) |
H2AB | 0.3868 | 0.4176 | 0.1309 | 0.060* | 0.464 (13) |
C3A | 0.3346 (5) | 0.672 (2) | 0.3374 (9) | 0.035 (3)* | 0.464 (13) |
C2A | 0.3900 (7) | 0.468 (3) | 0.3041 (9) | 0.046 (4)* | 0.464 (13) |
N1A | 0.4320 (4) | 0.3612 (19) | 0.3985 (11) | 0.048 (3)* | 0.464 (13) |
H1A | 0.4671 | 0.2394 | 0.3821 | 0.057* | 0.464 (13) |
C6A | 0.4209 (7) | 0.438 (3) | 0.5161 (12) | 0.056 (3)* | 0.464 (13) |
H6A | 0.4510 | 0.3597 | 0.5772 | 0.067* | 0.464 (13) |
C5A | 0.3657 (8) | 0.631 (3) | 0.5456 (10) | 0.057 (3)* | 0.464 (13) |
H5A | 0.3564 | 0.6777 | 0.6268 | 0.069* | 0.464 (13) |
C4A | 0.3246 (6) | 0.752 (2) | 0.4556 (12) | 0.046 (3)* | 0.464 (13) |
H4A | 0.2890 | 0.8921 | 0.4749 | 0.056* | 0.464 (13) |
N3A | 0.2895 (9) | 0.795 (4) | 0.2372 (14) | 0.050 (3) | 0.464 (13) |
O11A | 0.2881 (9) | 0.668 (3) | 0.1350 (11) | 0.076 (3) | 0.464 (13) |
O12A | 0.2562 (7) | 1.014 (3) | 0.2589 (12) | 0.076 (4) | 0.464 (13) |
O3 | 0.5491 (7) | −0.147 (3) | 0.2744 (9) | 0.068 (3) | 0.536 (13) |
O3A | 0.5333 (8) | −0.022 (3) | 0.2650 (12) | 0.068 (3) | 0.464 (13) |
O2A | 0.5520 (14) | −0.083 (5) | 0.476 (2) | 0.066 (5) | 0.464 (13) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N2 | 0.067 (6) | 0.073 (7) | 0.042 (5) | 0.002 (4) | −0.008 (4) | 0.006 (4) |
N3 | 0.056 (8) | 0.102 (14) | 0.075 (12) | −0.020 (8) | −0.012 (8) | 0.032 (10) |
O11 | 0.124 (11) | 0.129 (10) | 0.081 (7) | −0.027 (7) | −0.057 (7) | 0.037 (6) |
O12 | 0.090 (8) | 0.18 (2) | 0.159 (18) | 0.043 (9) | −0.030 (10) | 0.094 (17) |
S1 | 0.0538 (5) | 0.0345 (4) | 0.0655 (6) | −0.0006 (4) | 0.0145 (6) | 0.0000 (6) |
O1 | 0.0487 (14) | 0.0444 (11) | 0.092 (2) | 0.0007 (10) | 0.0147 (15) | −0.0014 (19) |
O2 | 0.060 (5) | 0.055 (8) | 0.041 (6) | 0.023 (5) | 0.016 (4) | 0.000 (5) |
O4 | 0.092 (5) | 0.036 (3) | 0.062 (5) | 0.011 (3) | 0.005 (4) | 0.004 (3) |
O4A | 0.083 (5) | 0.032 (3) | 0.084 (8) | 0.004 (3) | −0.010 (4) | −0.003 (4) |
N2A | 0.049 (5) | 0.055 (7) | 0.045 (6) | 0.015 (4) | 0.004 (4) | −0.004 (5) |
N3A | 0.044 (7) | 0.056 (7) | 0.051 (6) | 0.003 (5) | −0.004 (5) | −0.006 (6) |
O11A | 0.085 (8) | 0.090 (9) | 0.054 (6) | 0.016 (6) | −0.018 (5) | −0.007 (6) |
O12A | 0.052 (5) | 0.059 (5) | 0.117 (9) | 0.017 (4) | 0.009 (5) | 0.000 (5) |
O3 | 0.081 (6) | 0.082 (8) | 0.042 (4) | 0.006 (5) | −0.020 (4) | −0.006 (5) |
O3A | 0.074 (6) | 0.062 (8) | 0.068 (6) | 0.016 (5) | −0.025 (4) | 0.002 (5) |
O2A | 0.078 (10) | 0.068 (12) | 0.051 (6) | 0.001 (7) | 0.035 (6) | −0.013 (8) |
Geometric parameters (Å, º) top
N2—H2A | 0.8600 | S1—O3 | 1.280 (10) |
N2—H2B | 0.8600 | S1—O3A | 1.610 (11) |
N2—C2 | 1.306 (10) | S1—O2A | 1.28 (2) |
C3—C2 | 1.394 (12) | O1—H1B | 0.8200 |
C3—C4 | 1.395 (12) | N2A—H2AA | 0.8600 |
C3—N3 | 1.452 (13) | N2A—H2AB | 0.8600 |
C2—N1 | 1.381 (11) | N2A—C2A | 1.329 (12) |
N1—H1 | 0.8600 | C3A—C2A | 1.411 (13) |
N1—C6 | 1.347 (12) | C3A—C4A | 1.356 (13) |
C6—H6 | 0.9300 | C3A—N3A | 1.473 (13) |
C6—C5 | 1.348 (12) | C2A—N1A | 1.369 (13) |
C5—H5 | 0.9300 | N1A—H1A | 0.8600 |
C5—C4 | 1.400 (12) | N1A—C6A | 1.348 (15) |
C4—H4 | 0.9300 | C6A—H6A | 0.9300 |
N3—O11 | 1.24 (2) | C6A—C5A | 1.364 (15) |
N3—O12 | 1.18 (2) | C5A—H5A | 0.9300 |
S1—O1 | 1.547 (3) | C5A—C4A | 1.348 (15) |
S1—O2 | 1.563 (15) | C4A—H4A | 0.9300 |
S1—O4 | 1.510 (6) | N3A—O11A | 1.26 (2) |
S1—O4A | 1.435 (7) | N3A—O12A | 1.193 (19) |
| | | |
H2A—N2—H2B | 120.0 | O3—S1—O2 | 115.3 (9) |
C2—N2—H2A | 120.0 | O3—S1—O4 | 118.7 (6) |
C2—N2—H2B | 120.0 | O2A—S1—O1 | 111.8 (13) |
C2—C3—C4 | 121.7 (8) | O2A—S1—O4A | 121.8 (11) |
C2—C3—N3 | 122.9 (13) | O2A—S1—O3A | 108.3 (12) |
C4—C3—N3 | 115.4 (12) | S1—O1—H1B | 109.5 |
N2—C2—C3 | 129.2 (10) | H2AA—N2A—H2AB | 120.0 |
N2—C2—N1 | 116.6 (10) | C2A—N2A—H2AA | 120.0 |
N1—C2—C3 | 114.2 (7) | C2A—N2A—H2AB | 120.0 |
C2—N1—H1 | 117.6 | C2A—C3A—N3A | 116.5 (10) |
C6—N1—C2 | 124.8 (7) | C4A—C3A—C2A | 121.2 (9) |
C6—N1—H1 | 117.6 | C4A—C3A—N3A | 122.3 (12) |
N1—C6—H6 | 119.3 | N2A—C2A—C3A | 131.4 (11) |
N1—C6—C5 | 121.4 (7) | N2A—C2A—N1A | 113.3 (10) |
C5—C6—H6 | 119.3 | N1A—C2A—C3A | 115.3 (8) |
C6—C5—H5 | 121.4 | C2A—N1A—H1A | 118.4 |
C6—C5—C4 | 117.3 (7) | C6A—N1A—C2A | 123.1 (9) |
C4—C5—H5 | 121.4 | C6A—N1A—H1A | 118.4 |
C3—C4—C5 | 120.5 (8) | N1A—C6A—H6A | 120.0 |
C3—C4—H4 | 119.7 | N1A—C6A—C5A | 120.1 (9) |
C5—C4—H4 | 119.7 | C5A—C6A—H6A | 120.0 |
O11—N3—C3 | 114.8 (17) | C6A—C5A—H5A | 120.3 |
O12—N3—C3 | 119 (2) | C4A—C5A—C6A | 119.3 (10) |
O12—N3—O11 | 126.2 (15) | C4A—C5A—H5A | 120.3 |
O1—S1—O2 | 105.6 (9) | C3A—C4A—H4A | 119.6 |
O1—S1—O3A | 103.4 (6) | C5A—C4A—C3A | 120.9 (10) |
O4—S1—O1 | 98.5 (3) | C5A—C4A—H4A | 119.6 |
O4—S1—O2 | 105.5 (7) | O11A—N3A—C3A | 119.7 (14) |
O4A—S1—O1 | 108.2 (3) | O12A—N3A—C3A | 116.6 (13) |
O4A—S1—O3A | 101.3 (6) | O12A—N3A—O11A | 123.7 (12) |
O3—S1—O1 | 111.3 (6) | | |
| | | |
N2—C2—N1—C6 | 179.2 (8) | N2A—C2A—N1A—C6A | −179.8 (11) |
C3—C2—N1—C6 | −2.6 (13) | C3A—C2A—N1A—C6A | 1.5 (15) |
C2—C3—C4—C5 | 1.2 (13) | C2A—C3A—C4A—C5A | −2.4 (16) |
C2—C3—N3—O11 | 12.1 (19) | C2A—C3A—N3A—O11A | 17 (2) |
C2—C3—N3—O12 | −167.6 (13) | C2A—C3A—N3A—O12A | −162.1 (14) |
C2—N1—C6—C5 | 1.8 (13) | C2A—N1A—C6A—C5A | 0.0 (17) |
N1—C6—C5—C4 | 0.6 (12) | N1A—C6A—C5A—C4A | −2.8 (17) |
C6—C5—C4—C3 | −2.0 (12) | C6A—C5A—C4A—C3A | 4.0 (17) |
C4—C3—C2—N2 | 179.0 (10) | C4A—C3A—C2A—N2A | −178.7 (12) |
C4—C3—C2—N1 | 1.1 (12) | C4A—C3A—C2A—N1A | −0.3 (15) |
C4—C3—N3—O11 | −167.6 (12) | C4A—C3A—N3A—O11A | −163.4 (15) |
C4—C3—N3—O12 | 12.8 (19) | C4A—C3A—N3A—O12A | 17 (2) |
N3—C3—C2—N2 | −0.6 (17) | N3A—C3A—C2A—N2A | 0 (2) |
N3—C3—C2—N1 | −178.6 (11) | N3A—C3A—C2A—N1A | 178.8 (11) |
N3—C3—C4—C5 | −179.2 (10) | N3A—C3A—C4A—C5A | 178.5 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3 | 0.86 | 2.04 | 2.897 (13) | 177 |
N2—H2B···O11 | 0.86 | 2.12 | 2.682 (14) | 122 |
N2—H2B···O2i | 0.86 | 2.44 | 3.01 (2) | 124 |
N1—H1···O2 | 0.86 | 1.85 | 2.704 (15) | 171 |
C6—H6···O3ii | 0.93 | 2.37 | 3.207 (13) | 149 |
O1—H1B···O4iii | 0.82 | 1.85 | 2.652 (7) | 164 |
O1—H1B···O4Aiii | 0.82 | 1.83 | 2.612 (7) | 160 |
N2A—H2AA···O3A | 0.86 | 2.13 | 2.923 (12) | 154 |
N2A—H2AB···O11A | 0.86 | 2.11 | 2.676 (17) | 123 |
N1A—H1A···O3A | 0.86 | 2.12 | 2.916 (18) | 155 |
N1A—H1A···O2A | 0.86 | 2.35 | 3.08 (2) | 142 |
Symmetry codes: (i) −x+1, −y, z−1/2; (ii) −x+1, −y, z+1/2; (iii) x, y+1, z. |
Crystal data top
C5H6N3O2·HO4S | F(000) = 976 |
Mr = 237.20 | Dx = 1.793 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.051 (3) Å | Cell parameters from 26437 reflections |
b = 10.968 (4) Å | θ = 2.4–29.5° |
c = 18.268 (5) Å | µ = 0.39 mm−1 |
β = 104.35 (3)° | T = 100 K |
V = 1756.9 (10) Å3 | Block, yellow |
Z = 8 | 0.56 × 0.41 × 0.14 mm |
Data collection top
Xcalibur, Atlas diffractometer | 8812 independent reflections |
Graphite monochromator | 8592 reflections with I > 2σ(I) |
Detector resolution: 10.6249 pixels mm-1 | Rint = 0.020 |
ω scans | θmax = 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 = −12→12 |
Tmin = 0.967, Tmax = 1.000 | k = −14→14 |
46250 measured reflections | l = −24→24 |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.022 | H-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 reflections | Δρmax = 0.20 e Å−3 |
546 parameters | Δρmin = −0.42 e Å−3 |
1 restraint | Absolute 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 | x | y | z | Uiso*/Ueq | |
N11 | 0.4029 (3) | 0.7320 (2) | 0.43391 (13) | 0.0143 (5) | |
H11 | 0.3565 | 0.7391 | 0.4707 | 0.017* | |
C12 | 0.4119 (4) | 0.6185 (3) | 0.40504 (14) | 0.0146 (7) | |
N12 | 0.3488 (3) | 0.5275 (2) | 0.43339 (13) | 0.0183 (6) | |
H12A | 0.3028 | 0.5411 | 0.4698 | 0.022* | |
H12B | 0.3527 | 0.4531 | 0.4159 | 0.022* | |
C13 | 0.4882 (4) | 0.6143 (3) | 0.34551 (15) | 0.0151 (7) | |
N13 | 0.5057 (3) | 0.4981 (3) | 0.30902 (15) | 0.0236 (6) | |
O1 | 0.4339 (3) | 0.4088 (2) | 0.32156 (13) | 0.0289 (6) | |
O2 | 0.5921 (3) | 0.4972 (3) | 0.26634 (13) | 0.0372 (7) | |
C14 | 0.5440 (4) | 0.7185 (3) | 0.31982 (17) | 0.0192 (8) | |
H14 | 0.5923 | 0.7138 | 0.2793 | 0.023* | |
C15 | 0.5298 (4) | 0.8308 (3) | 0.35321 (17) | 0.0201 (7) | |
H15 | 0.5685 | 0.9031 | 0.3362 | 0.024* | |
C16 | 0.4596 (4) | 0.8342 (3) | 0.41033 (17) | 0.0167 (7) | |
H16 | 0.4500 | 0.9097 | 0.4342 | 0.020* | |
N21 | 0.8949 (3) | 0.6883 (2) | 0.43557 (13) | 0.0161 (5) | |
H21 | 0.8497 | 0.6697 | 0.4715 | 0.019* | |
C22 | 0.9303 (4) | 0.5952 (3) | 0.39390 (15) | 0.0129 (6) | |
N22 | 0.8945 (3) | 0.4841 (2) | 0.41067 (13) | 0.0170 (5) | |
H22A | 0.8494 | 0.4725 | 0.4476 | 0.020* | |
H22B | 0.9156 | 0.4214 | 0.3849 | 0.020* | |
C23 | 1.0027 (4) | 0.6305 (3) | 0.33708 (16) | 0.0135 (6) | |
N23 | 1.0514 (3) | 0.5383 (2) | 0.29027 (13) | 0.0152 (5) | |
O3 | 0.9927 (3) | 0.4364 (2) | 0.28644 (13) | 0.0245 (5) | |
O4 | 1.1499 (2) | 0.5676 (2) | 0.25813 (11) | 0.0217 (5) | |
C24 | 1.0329 (3) | 0.7516 (3) | 0.32514 (16) | 0.0179 (8) | |
H24 | 1.0811 | 0.7733 | 0.2863 | 0.021* | |
C25 | 0.9923 (4) | 0.8417 (3) | 0.37034 (17) | 0.0190 (7) | |
H25 | 1.0118 | 0.9253 | 0.3626 | 0.023* | |
C26 | 0.9241 (4) | 0.8077 (3) | 0.42591 (16) | 0.0196 (7) | |
H26 | 0.8970 | 0.8677 | 0.4578 | 0.024* | |
N31 | 0.0351 (3) | 0.7304 (2) | −0.06554 (13) | 0.0132 (5) | |
H31 | 0.1177 | 0.7380 | −0.0284 | 0.016* | |
C32 | −0.0024 (4) | 0.6171 (3) | −0.09381 (14) | 0.0126 (6) | |
N32 | 0.0903 (3) | 0.5257 (2) | −0.06450 (13) | 0.0169 (5) | |
H32A | 0.1725 | 0.5400 | −0.0281 | 0.020* | |
H32B | 0.0694 | 0.4510 | −0.0815 | 0.020* | |
C33 | −0.1389 (4) | 0.6109 (3) | −0.15302 (16) | 0.0177 (7) | |
N33 | −0.1927 (3) | 0.4941 (3) | −0.18829 (15) | 0.0232 (6) | |
O5 | −0.1053 (3) | 0.4059 (2) | −0.17510 (12) | 0.0285 (5) | |
O6 | −0.3224 (3) | 0.4902 (3) | −0.22958 (13) | 0.0363 (7) | |
C34 | −0.2213 (4) | 0.7136 (3) | −0.17920 (18) | 0.0212 (8) | |
H34 | −0.3108 | 0.7069 | −0.2192 | 0.025* | |
C35 | −0.1762 (4) | 0.8276 (3) | −0.14818 (17) | 0.0216 (7) | |
H35 | −0.2331 | 0.8990 | −0.1661 | 0.026* | |
C36 | −0.0453 (4) | 0.8325 (3) | −0.09027 (17) | 0.0173 (7) | |
H36 | −0.0114 | 0.9087 | −0.0675 | 0.021* | |
N41 | 0.5341 (3) | 0.6876 (3) | −0.06634 (13) | 0.0155 (5) | |
H41 | 0.6150 | 0.6702 | −0.0299 | 0.019* | |
C42 | 0.4593 (3) | 0.5934 (3) | −0.10763 (14) | 0.0136 (6) | |
N42 | 0.5113 (3) | 0.4821 (2) | −0.09082 (13) | 0.0178 (5) | |
H42A | 0.5928 | 0.4703 | −0.0536 | 0.021* | |
H42B | 0.4647 | 0.4196 | −0.1168 | 0.021* | |
C43 | 0.3276 (4) | 0.6279 (3) | −0.16478 (15) | 0.0148 (6) | |
N43 | 0.2358 (3) | 0.5343 (2) | −0.21171 (13) | 0.0160 (6) | |
O7 | 0.2930 (3) | 0.4339 (2) | −0.21597 (12) | 0.0249 (5) | |
O8 | 0.1058 (2) | 0.5623 (2) | −0.24486 (11) | 0.0229 (5) | |
C44 | 0.2841 (4) | 0.7474 (3) | −0.17639 (17) | 0.0186 (7) | |
H44 | 0.1962 | 0.7677 | −0.2150 | 0.022* | |
C45 | 0.3675 (5) | 0.8394 (3) | −0.13211 (17) | 0.0213 (8) | |
H45 | 0.3381 | 0.9225 | −0.1397 | 0.026* | |
C46 | 0.4938 (4) | 0.8056 (3) | −0.07702 (18) | 0.0196 (7) | |
H46 | 0.5534 | 0.8663 | −0.0461 | 0.023* | |
S1 | 0.21518 (10) | 0.68409 (8) | 0.59158 (5) | 0.01190 (19) | |
O11 | 0.3470 (3) | 0.6661 (2) | 0.66437 (11) | 0.0182 (5) | |
H11A | 0.4311 | 0.6651 | 0.6526 | 0.027* | |
O14 | 0.0876 (2) | 0.72424 (18) | 0.62073 (12) | 0.0183 (5) | |
O12 | 0.2639 (3) | 0.7788 (2) | 0.54631 (11) | 0.0159 (5) | |
O13 | 0.1896 (2) | 0.5679 (2) | 0.55224 (12) | 0.0190 (5) | |
S2 | 0.71331 (11) | 0.65600 (7) | 0.58390 (5) | 0.0126 (2) | |
O21 | 0.8358 (3) | 0.6461 (3) | 0.66030 (12) | 0.0179 (5) | |
H21A | 0.9187 | 0.6749 | 0.6553 | 0.027* | |
O24 | 0.5732 (2) | 0.6230 (2) | 0.60385 (12) | 0.0202 (5) | |
O22 | 0.7174 (3) | 0.7790 (2) | 0.55594 (13) | 0.0223 (5) | |
O23 | 0.7532 (2) | 0.5672 (2) | 0.53231 (12) | 0.0210 (5) | |
S3 | 0.37920 (11) | 0.68151 (8) | 0.09352 (4) | 0.01170 (19) | |
O31 | 0.3135 (3) | 0.6681 (2) | 0.16461 (11) | 0.0179 (6) | |
H31A | 0.2204 | 0.6506 | 0.1509 | 0.027* | |
O32 | 0.2901 (3) | 0.7764 (2) | 0.04586 (11) | 0.0167 (5) | |
O33 | 0.3659 (3) | 0.5655 (2) | 0.05501 (12) | 0.0207 (5) | |
O34 | 0.5358 (2) | 0.72037 (18) | 0.12587 (11) | 0.0180 (5) | |
S4 | 0.86551 (10) | 0.65476 (8) | 0.08034 (4) | 0.0128 (2) | |
O41 | 0.8217 (3) | 0.6433 (3) | 0.15829 (11) | 0.0197 (5) | |
H41A | 0.7269 | 0.6507 | 0.1514 | 0.030* | |
O42 | 0.8268 (3) | 0.7776 (2) | 0.05264 (12) | 0.0227 (5) | |
O43 | 0.7740 (2) | 0.5651 (2) | 0.02974 (11) | 0.0216 (5) | |
O44 | 1.0261 (2) | 0.6255 (2) | 0.09767 (11) | 0.0181 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0165 (13) | 0.0145 (13) | 0.0121 (11) | 0.0014 (12) | 0.0039 (10) | 0.0007 (9) |
C12 | 0.0155 (15) | 0.0137 (16) | 0.0121 (12) | 0.0016 (11) | −0.0014 (11) | −0.0023 (11) |
N12 | 0.0241 (14) | 0.0131 (14) | 0.0183 (12) | 0.0002 (10) | 0.0065 (10) | −0.0018 (9) |
C13 | 0.0146 (15) | 0.0167 (16) | 0.0130 (12) | 0.0046 (12) | 0.0015 (12) | −0.0020 (11) |
N13 | 0.0256 (14) | 0.0266 (16) | 0.0170 (12) | 0.0122 (13) | 0.0018 (11) | −0.0027 (11) |
O1 | 0.0356 (13) | 0.0199 (12) | 0.0295 (12) | 0.0053 (11) | 0.0050 (11) | −0.0095 (9) |
O2 | 0.0497 (16) | 0.0428 (17) | 0.0248 (12) | 0.0145 (14) | 0.0200 (12) | −0.0053 (11) |
C14 | 0.0137 (16) | 0.029 (2) | 0.0144 (14) | 0.0013 (13) | 0.0028 (12) | 0.0012 (11) |
C15 | 0.0196 (16) | 0.0212 (16) | 0.0174 (14) | −0.0035 (12) | 0.0004 (13) | 0.0078 (12) |
C16 | 0.0158 (15) | 0.0108 (15) | 0.0197 (13) | −0.0015 (11) | −0.0027 (13) | 0.0002 (11) |
N21 | 0.0189 (13) | 0.0147 (13) | 0.0151 (11) | 0.0007 (11) | 0.0050 (10) | 0.0000 (10) |
C22 | 0.0112 (13) | 0.0130 (14) | 0.0136 (12) | 0.0024 (11) | 0.0013 (11) | 0.0006 (10) |
N22 | 0.0249 (13) | 0.0112 (13) | 0.0180 (11) | −0.0038 (10) | 0.0113 (10) | −0.0001 (9) |
C23 | 0.0152 (13) | 0.0129 (15) | 0.0117 (11) | −0.0001 (12) | 0.0020 (11) | −0.0015 (10) |
N23 | 0.0146 (11) | 0.0184 (14) | 0.0121 (11) | −0.0004 (10) | 0.0020 (10) | 0.0034 (9) |
O3 | 0.0319 (12) | 0.0170 (12) | 0.0268 (11) | −0.0051 (10) | 0.0115 (10) | −0.0049 (9) |
O4 | 0.0181 (10) | 0.0328 (13) | 0.0168 (9) | 0.0007 (9) | 0.0092 (8) | 0.0029 (9) |
C24 | 0.0196 (17) | 0.0166 (18) | 0.0158 (13) | −0.0039 (12) | 0.0010 (12) | 0.0079 (12) |
C25 | 0.0205 (16) | 0.0104 (13) | 0.0219 (15) | −0.0018 (12) | −0.0027 (13) | 0.0036 (11) |
C26 | 0.0206 (15) | 0.0165 (17) | 0.0172 (14) | 0.0030 (13) | −0.0037 (12) | −0.0024 (11) |
N31 | 0.0130 (12) | 0.0144 (14) | 0.0122 (11) | −0.0014 (11) | 0.0031 (10) | −0.0002 (9) |
C32 | 0.0146 (14) | 0.0132 (16) | 0.0120 (11) | −0.0032 (11) | 0.0069 (11) | −0.0008 (11) |
N32 | 0.0203 (13) | 0.0126 (13) | 0.0169 (11) | 0.0001 (10) | 0.0031 (10) | −0.0013 (9) |
C33 | 0.0201 (18) | 0.0210 (18) | 0.0136 (12) | −0.0071 (13) | 0.0071 (13) | −0.0023 (12) |
N33 | 0.0244 (14) | 0.0288 (16) | 0.0172 (12) | −0.0100 (13) | 0.0066 (11) | −0.0057 (11) |
O5 | 0.0368 (13) | 0.0235 (13) | 0.0256 (11) | −0.0091 (11) | 0.0087 (11) | −0.0094 (9) |
O6 | 0.0297 (14) | 0.0451 (17) | 0.0277 (12) | −0.0184 (14) | −0.0049 (11) | −0.0054 (11) |
C34 | 0.0179 (16) | 0.031 (2) | 0.0146 (13) | −0.0041 (14) | 0.0043 (12) | 0.0038 (12) |
C35 | 0.0183 (17) | 0.0292 (18) | 0.0172 (14) | 0.0036 (13) | 0.0046 (13) | 0.0069 (13) |
C36 | 0.0197 (17) | 0.0159 (16) | 0.0169 (13) | −0.0012 (12) | 0.0056 (13) | 0.0023 (11) |
N41 | 0.0152 (12) | 0.0190 (14) | 0.0125 (10) | −0.0001 (12) | 0.0038 (10) | 0.0011 (11) |
C42 | 0.0137 (15) | 0.0161 (14) | 0.0122 (12) | 0.0016 (12) | 0.0056 (11) | −0.0026 (11) |
N42 | 0.0175 (12) | 0.0175 (13) | 0.0152 (11) | 0.0025 (10) | −0.0016 (10) | −0.0002 (9) |
C43 | 0.0119 (14) | 0.0213 (16) | 0.0106 (11) | 0.0023 (13) | 0.0018 (11) | −0.0007 (11) |
N43 | 0.0184 (13) | 0.0172 (14) | 0.0111 (11) | −0.0031 (11) | 0.0013 (10) | −0.0023 (10) |
O7 | 0.0259 (12) | 0.0205 (12) | 0.0232 (11) | 0.0009 (9) | −0.0038 (10) | −0.0080 (9) |
O8 | 0.0156 (11) | 0.0341 (14) | 0.0160 (9) | 0.0022 (9) | −0.0016 (8) | 0.0017 (9) |
C44 | 0.0203 (18) | 0.0218 (18) | 0.0148 (13) | 0.0056 (13) | 0.0065 (13) | 0.0023 (12) |
C45 | 0.038 (2) | 0.0127 (14) | 0.0157 (14) | 0.0037 (14) | 0.0119 (15) | 0.0022 (11) |
C46 | 0.0239 (16) | 0.0158 (16) | 0.0221 (15) | −0.0047 (14) | 0.0114 (14) | −0.0026 (12) |
S1 | 0.0120 (4) | 0.0095 (5) | 0.0148 (4) | 0.0005 (3) | 0.0046 (3) | 0.0005 (3) |
O11 | 0.0147 (11) | 0.0271 (14) | 0.0141 (8) | 0.0034 (9) | 0.0060 (9) | 0.0013 (8) |
O14 | 0.0158 (9) | 0.0147 (11) | 0.0271 (11) | 0.0016 (8) | 0.0107 (8) | 0.0041 (8) |
O12 | 0.0192 (10) | 0.0116 (10) | 0.0196 (9) | 0.0017 (8) | 0.0098 (8) | 0.0024 (8) |
O13 | 0.0236 (11) | 0.0109 (11) | 0.0229 (11) | −0.0025 (9) | 0.0064 (9) | −0.0037 (9) |
S2 | 0.0116 (4) | 0.0117 (5) | 0.0146 (3) | 0.0015 (3) | 0.0033 (3) | 0.0014 (3) |
O21 | 0.0115 (11) | 0.0254 (12) | 0.0162 (9) | −0.0020 (10) | 0.0021 (9) | 0.0050 (8) |
O24 | 0.0122 (9) | 0.0233 (13) | 0.0264 (11) | −0.0003 (8) | 0.0075 (8) | −0.0039 (8) |
O22 | 0.0245 (12) | 0.0140 (11) | 0.0268 (11) | 0.0013 (10) | 0.0035 (10) | 0.0071 (9) |
O23 | 0.0265 (11) | 0.0170 (11) | 0.0232 (11) | −0.0034 (9) | 0.0134 (9) | −0.0035 (8) |
S3 | 0.0105 (3) | 0.0118 (5) | 0.0129 (3) | −0.0004 (3) | 0.0031 (3) | 0.0005 (3) |
O31 | 0.0122 (11) | 0.0302 (15) | 0.0122 (8) | 0.0001 (9) | 0.0048 (9) | 0.0020 (8) |
O32 | 0.0156 (10) | 0.0136 (11) | 0.0186 (9) | −0.0023 (9) | −0.0001 (8) | 0.0038 (8) |
O33 | 0.0208 (11) | 0.0162 (12) | 0.0234 (11) | 0.0024 (9) | 0.0024 (9) | −0.0048 (9) |
O34 | 0.0129 (9) | 0.0177 (12) | 0.0237 (10) | 0.0005 (8) | 0.0052 (8) | 0.0020 (8) |
S4 | 0.0100 (4) | 0.0156 (6) | 0.0128 (3) | 0.0005 (3) | 0.0031 (3) | 0.0018 (3) |
O41 | 0.0159 (11) | 0.0293 (12) | 0.0142 (8) | 0.0058 (11) | 0.0042 (9) | 0.0042 (8) |
O42 | 0.0242 (13) | 0.0168 (12) | 0.0284 (11) | 0.0039 (10) | 0.0093 (10) | 0.0075 (9) |
O43 | 0.0172 (11) | 0.0219 (12) | 0.0230 (10) | −0.0023 (9) | 0.0001 (8) | −0.0051 (9) |
O44 | 0.0116 (9) | 0.0241 (12) | 0.0185 (10) | 0.0001 (8) | 0.0035 (7) | −0.0022 (8) |
Geometric parameters (Å, º) top
N11—H11 | 0.8800 | N33—O6 | 1.229 (4) |
N11—C12 | 1.362 (4) | C34—H34 | 0.9500 |
N11—C16 | 1.347 (4) | C34—C35 | 1.392 (5) |
C12—N12 | 1.319 (4) | C35—H35 | 0.9500 |
C12—C13 | 1.426 (4) | C35—C36 | 1.380 (4) |
N12—H12A | 0.8800 | C36—H36 | 0.9500 |
N12—H12B | 0.8800 | N41—H41 | 0.8800 |
C13—N13 | 1.465 (4) | N41—C42 | 1.357 (4) |
C13—C14 | 1.378 (5) | N41—C46 | 1.346 (4) |
N13—O1 | 1.227 (4) | C42—N42 | 1.317 (4) |
N13—O2 | 1.233 (4) | C42—C43 | 1.427 (4) |
C14—H14 | 0.9500 | N42—H42A | 0.8800 |
C14—C15 | 1.394 (5) | N42—H42B | 0.8800 |
C15—H15 | 0.9500 | C43—N43 | 1.458 (4) |
C15—C16 | 1.350 (4) | C43—C44 | 1.370 (5) |
C16—H16 | 0.9500 | N43—O7 | 1.228 (3) |
N21—H21 | 0.8800 | N43—O8 | 1.221 (3) |
N21—C22 | 1.358 (4) | C44—H44 | 0.9500 |
N21—C26 | 1.357 (4) | C44—C45 | 1.393 (5) |
C22—N22 | 1.317 (4) | C45—H45 | 0.9500 |
C22—C23 | 1.412 (4) | C45—C46 | 1.373 (5) |
N22—H22A | 0.8800 | C46—H46 | 0.9500 |
N22—H22B | 0.8800 | S1—O11 | 1.563 (2) |
C23—N23 | 1.461 (4) | S1—O14 | 1.454 (2) |
C23—C24 | 1.385 (4) | S1—O12 | 1.462 (2) |
N23—O3 | 1.232 (3) | S1—O13 | 1.453 (2) |
N23—O4 | 1.226 (3) | O11—H11A | 0.8400 |
C24—H24 | 0.9500 | S2—O21 | 1.556 (2) |
C24—C25 | 1.394 (5) | S2—O24 | 1.450 (2) |
C25—H25 | 0.9500 | S2—O22 | 1.446 (3) |
C25—C26 | 1.365 (5) | S2—O23 | 1.461 (2) |
C26—H26 | 0.9500 | O21—H21A | 0.8400 |
N31—H31 | 0.8800 | S3—O31 | 1.563 (2) |
N31—C32 | 1.357 (4) | S3—O32 | 1.464 (2) |
N31—C36 | 1.351 (4) | S3—O33 | 1.444 (2) |
C32—N32 | 1.331 (4) | S3—O34 | 1.458 (2) |
C32—C33 | 1.427 (4) | O31—H31A | 0.8400 |
N32—H32A | 0.8800 | S4—O41 | 1.575 (2) |
N32—H32B | 0.8800 | S4—O42 | 1.451 (3) |
C33—N33 | 1.462 (4) | S4—O43 | 1.459 (2) |
C33—C34 | 1.370 (5) | S4—O44 | 1.445 (2) |
N33—O5 | 1.235 (4) | O41—H41A | 0.8400 |
| | | |
C12—N11—H11 | 117.5 | O6—N33—O5 | 124.1 (3) |
C16—N11—H11 | 117.5 | C33—C34—H34 | 119.4 |
C16—N11—C12 | 124.9 (3) | C33—C34—C35 | 121.1 (3) |
N11—C12—C13 | 114.3 (3) | C35—C34—H34 | 119.4 |
N12—C12—N11 | 117.8 (3) | C34—C35—H35 | 121.4 |
N12—C12—C13 | 127.9 (3) | C36—C35—C34 | 117.2 (3) |
C12—N12—H12A | 120.0 | C36—C35—H35 | 121.4 |
C12—N12—H12B | 120.0 | N31—C36—C35 | 120.9 (3) |
H12A—N12—H12B | 120.0 | N31—C36—H36 | 119.6 |
C12—C13—N13 | 120.1 (3) | C35—C36—H36 | 119.6 |
C14—C13—C12 | 121.4 (3) | C42—N41—H41 | 117.6 |
C14—C13—N13 | 118.5 (3) | C46—N41—H41 | 117.6 |
O1—N13—C13 | 119.2 (3) | C46—N41—C42 | 124.9 (3) |
O1—N13—O2 | 124.0 (3) | N41—C42—C43 | 114.6 (3) |
O2—N13—C13 | 116.8 (3) | N42—C42—N41 | 118.4 (3) |
C13—C14—H14 | 119.9 | N42—C42—C43 | 127.0 (3) |
C13—C14—C15 | 120.1 (3) | C42—N42—H42A | 120.0 |
C15—C14—H14 | 119.9 | C42—N42—H42B | 120.0 |
C14—C15—H15 | 120.8 | H42A—N42—H42B | 120.0 |
C16—C15—C14 | 118.3 (3) | C42—C43—N43 | 119.7 (3) |
C16—C15—H15 | 120.8 | C44—C43—C42 | 121.5 (3) |
N11—C16—C15 | 120.9 (3) | C44—C43—N43 | 118.8 (3) |
N11—C16—H16 | 119.5 | O7—N43—C43 | 118.7 (3) |
C15—C16—H16 | 119.5 | O8—N43—C43 | 117.0 (3) |
C22—N21—H21 | 117.5 | O8—N43—O7 | 124.3 (3) |
C26—N21—H21 | 117.5 | C43—C44—H44 | 119.7 |
C26—N21—C22 | 124.9 (3) | C43—C44—C45 | 120.6 (3) |
N21—C22—C23 | 115.0 (3) | C45—C44—H44 | 119.7 |
N22—C22—N21 | 117.3 (3) | C44—C45—H45 | 121.2 |
N22—C22—C23 | 127.6 (3) | C46—C45—C44 | 117.6 (3) |
C22—N22—H22A | 120.0 | C46—C45—H45 | 121.2 |
C22—N22—H22B | 120.0 | N41—C46—C45 | 120.8 (3) |
H22A—N22—H22B | 120.0 | N41—C46—H46 | 119.6 |
C22—C23—N23 | 120.2 (3) | C45—C46—H46 | 119.6 |
C24—C23—C22 | 121.6 (3) | O14—S1—O11 | 103.57 (13) |
C24—C23—N23 | 118.2 (3) | O14—S1—O12 | 111.73 (13) |
O3—N23—C23 | 118.2 (3) | O12—S1—O11 | 107.26 (14) |
O4—N23—C23 | 117.4 (3) | O13—S1—O11 | 107.74 (13) |
O4—N23—O3 | 124.4 (3) | O13—S1—O14 | 113.79 (14) |
C23—C24—H24 | 120.2 | O13—S1—O12 | 112.10 (14) |
C23—C24—C25 | 119.7 (3) | S1—O11—H11A | 109.5 |
C25—C24—H24 | 120.2 | O24—S2—O21 | 103.32 (14) |
C24—C25—H25 | 120.6 | O24—S2—O23 | 111.54 (14) |
C26—C25—C24 | 118.8 (3) | O22—S2—O21 | 107.88 (15) |
C26—C25—H25 | 120.6 | O22—S2—O24 | 114.97 (15) |
N21—C26—C25 | 119.9 (3) | O22—S2—O23 | 111.21 (14) |
N21—C26—H26 | 120.0 | O23—S2—O21 | 107.28 (14) |
C25—C26—H26 | 120.0 | S2—O21—H21A | 109.5 |
C32—N31—H31 | 117.7 | O32—S3—O31 | 107.10 (13) |
C36—N31—H31 | 117.7 | O33—S3—O31 | 108.60 (13) |
C36—N31—C32 | 124.7 (3) | O33—S3—O32 | 111.66 (13) |
N31—C32—C33 | 114.8 (3) | O33—S3—O34 | 114.21 (14) |
N32—C32—N31 | 117.6 (3) | O34—S3—O31 | 102.86 (13) |
N32—C32—C33 | 127.6 (3) | O34—S3—O32 | 111.74 (14) |
C32—N32—H32A | 120.0 | S3—O31—H31A | 109.5 |
C32—N32—H32B | 120.0 | O42—S4—O41 | 107.25 (14) |
H32A—N32—H32B | 120.0 | O42—S4—O43 | 110.79 (14) |
C32—C33—N33 | 120.5 (3) | O43—S4—O41 | 106.77 (14) |
C34—C33—C32 | 121.3 (3) | O44—S4—O41 | 104.43 (14) |
C34—C33—N33 | 118.2 (3) | O44—S4—O42 | 115.18 (15) |
O5—N33—C33 | 118.2 (3) | O44—S4—O43 | 111.78 (14) |
O6—N33—C33 | 117.7 (3) | S4—O41—H41A | 109.5 |
| | | |
N11—C12—C13—N13 | −179.8 (3) | N31—C32—C33—N33 | −179.7 (3) |
N11—C12—C13—C14 | −1.2 (4) | N31—C32—C33—C34 | 1.4 (4) |
C12—N11—C16—C15 | 1.2 (4) | C32—N31—C36—C35 | 0.1 (5) |
C12—C13—N13—O1 | 11.5 (4) | C32—C33—N33—O5 | −12.2 (4) |
C12—C13—N13—O2 | −169.3 (3) | C32—C33—N33—O6 | 168.1 (3) |
C12—C13—C14—C15 | 1.5 (5) | C32—C33—C34—C35 | −1.0 (5) |
N12—C12—C13—N13 | −1.0 (5) | N32—C32—C33—N33 | 0.8 (5) |
N12—C12—C13—C14 | 177.6 (3) | N32—C32—C33—C34 | −178.1 (3) |
C13—C14—C15—C16 | −0.5 (5) | C33—C34—C35—C36 | 0.1 (5) |
N13—C13—C14—C15 | −179.9 (3) | N33—C33—C34—C35 | −179.9 (3) |
C14—C13—N13—O1 | −167.1 (3) | C34—C33—N33—O5 | 166.7 (3) |
C14—C13—N13—O2 | 12.1 (4) | C34—C33—N33—O6 | −13.0 (4) |
C14—C15—C16—N11 | −0.8 (4) | C34—C35—C36—N31 | 0.4 (4) |
C16—N11—C12—N12 | −179.0 (3) | C36—N31—C32—N32 | 178.6 (3) |
C16—N11—C12—C13 | −0.1 (4) | C36—N31—C32—C33 | −0.9 (4) |
N21—C22—C23—N23 | 177.8 (3) | N41—C42—C43—N43 | −178.6 (3) |
N21—C22—C23—C24 | −0.6 (5) | N41—C42—C43—C44 | 0.8 (4) |
C22—N21—C26—C25 | 0.8 (5) | C42—N41—C46—C45 | 1.0 (5) |
C22—C23—N23—O3 | 19.8 (4) | C42—C43—N43—O7 | −19.6 (4) |
C22—C23—N23—O4 | −159.3 (3) | C42—C43—N43—O8 | 160.9 (3) |
C22—C23—C24—C25 | 0.5 (5) | C42—C43—C44—C45 | −0.3 (5) |
N22—C22—C23—N23 | −2.0 (5) | N42—C42—C43—N43 | −0.1 (5) |
N22—C22—C23—C24 | 179.5 (3) | N42—C42—C43—C44 | 179.3 (3) |
C23—C24—C25—C26 | 0.4 (4) | C43—C44—C45—C46 | 0.0 (4) |
N23—C23—C24—C25 | −178.0 (3) | N43—C43—C44—C45 | 179.1 (3) |
C24—C23—N23—O3 | −161.7 (3) | C44—C43—N43—O7 | 161.0 (3) |
C24—C23—N23—O4 | 19.2 (4) | C44—C43—N43—O8 | −18.5 (4) |
C24—C25—C26—N21 | −1.0 (4) | C44—C45—C46—N41 | −0.4 (5) |
C26—N21—C22—N22 | 179.9 (3) | C46—N41—C42—N42 | −179.8 (3) |
C26—N21—C22—C23 | 0.0 (5) | C46—N41—C42—C43 | −1.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O12 | 0.88 | 1.84 | 2.710 (3) | 171 |
N12—H12A···O13 | 0.88 | 2.04 | 2.922 (3) | 178 |
N12—H12B···O1 | 0.88 | 2.09 | 2.691 (3) | 125 |
N12—H12B···O22i | 0.88 | 2.12 | 2.808 (4) | 135 |
C16—H16···O24ii | 0.95 | 2.43 | 3.186 (4) | 136 |
N21—H21···O22 | 0.88 | 2.48 | 3.187 (4) | 138 |
N21—H21···O23 | 0.88 | 1.93 | 2.767 (4) | 157 |
N22—H22A···O23 | 0.88 | 2.21 | 2.969 (3) | 144 |
N22—H22B···O3 | 0.88 | 2.09 | 2.686 (3) | 124 |
N22—H22B···O14i | 0.88 | 2.17 | 2.919 (3) | 144 |
C24—H24···O5iii | 0.95 | 2.55 | 3.419 (4) | 152 |
C26—H26···O13ii | 0.95 | 2.32 | 3.093 (4) | 138 |
N31—H31···O32 | 0.88 | 1.84 | 2.719 (3) | 172 |
N32—H32A···O33 | 0.88 | 2.03 | 2.912 (3) | 177 |
N32—H32B···O5 | 0.88 | 2.08 | 2.678 (3) | 124 |
N32—H32B···O42iv | 0.88 | 2.13 | 2.816 (4) | 135 |
C36—H36···O44iii | 0.95 | 2.44 | 3.223 (4) | 140 |
N41—H41···O42 | 0.88 | 2.43 | 3.141 (4) | 138 |
N41—H41···O43 | 0.88 | 1.95 | 2.777 (4) | 156 |
N42—H42A···O32iv | 0.88 | 2.37 | 2.875 (3) | 117 |
N42—H42A···O43 | 0.88 | 2.20 | 2.955 (3) | 143 |
N42—H42B···O7 | 0.88 | 2.08 | 2.678 (3) | 125 |
N42—H42B···O34iv | 0.88 | 2.19 | 2.950 (3) | 144 |
C46—H46···O33iii | 0.95 | 2.32 | 3.106 (4) | 139 |
O11—H11A···O24 | 0.84 | 1.80 | 2.599 (3) | 159 |
O21—H21A···O14v | 0.84 | 1.87 | 2.696 (3) | 166 |
O31—H31A···O44vi | 0.84 | 1.81 | 2.628 (3) | 165 |
O41—H41A···O34 | 0.84 | 1.84 | 2.646 (3) | 160 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y+1/2, −z; (iv) −x+1, y−1/2, −z; (v) x+1, y, z; (vi) x−1, y, z. |