organic compounds
of 2-phenylethanaminium 3-carboxyprop-2-enoate
aDepartment of Applied Physics, Sri Venkateswara College of Engineering, Chennai 602 117, India, bDepartment of Physics, Aksheyaa College of Engineering, Kancheepuram 603 314, India, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dDepartment of Physics, Presidency College, Chennai 600 005, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, mohan66@hotmail.com
The title molecular salt, C8H12N+·C4H3O4−, crystallized with two independent cations and anions in the The ethanaminium side chains of the cations exhibit anti conformations [C—C—C—N torsion angles = 176.5 (3) and −179.4 (3)°]. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds connect adjacent anions and cations, and , O—H⋯O hydrogen bonds connect adjacent anions, generating sheets parallel to (001).
CCDC reference: 1415628
1. Related literature
For the crystal structures of related compounds, see: Ambalatharasu et al. (2014); Lejon et al. (2006); Smith et al. (2003).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PLATON.
Supporting information
CCDC reference: 1415628
https://doi.org/10.1107/S2056989015014292/su5183sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014292/su5183Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015014292/su5183Isup3.cml
The molecular structure of the title molecular salt is illustrated in Fig. 1. The geometric parameters are comparable with those reported for similar structures (Ambalatharasu et al., 2014; Lejon et al., 2006; Smith et al., 2003). The
consists of two independent 2-phenylethanaminium cations and 3-carboxyprop-2-enoate anions. The cations are protonated at amine-N atoms, and in the cations the side chains exhibit anti-conformations [C1—C7—C8—N1 = 176.5 (3) ° and C9—C15—C16—N2 = 179.4 (3) °]. The dihedral angle between the aromatic rings, (C1—C6) and (C9—C14), is 34.0 (3)Å.In the crystal, the molecular structure is stabilized by a medium-strength intramolecular cation-anion N—H···O hydrogen bond (Table 1 and Fig. 2). Adjacent anions and cations are linked by further N—H···O and O—H···O hydrogen bonds into infinite two-dimensional networks parallel to the ab plane (Table 1 and Fig. 2). There are also weak C—H···O hydrogen bonds within the sheets (Table 1).
The title slat was synthesized by mixing 2-phenylethylamine (1.26 g) and fumaric acid (1.16 g) in methanol-water (1:1) and the single crystals suitable for X-ray diffraction were grown by slow evaporation.
Crystal data, data collection and structure
details are summarized in Table 2. All the H atoms were positioned geometrically and refined using a riding model: O—H = 0.82 Å, N—H = 0.89 Å, C—H = 0.93 - 0.97 Å with Uiso(H) = 1.5Ueq(O,N) for OH and NH3 H atoms and 1.2Ueq(C) for other H atoms. The bond distances C1—C6, C3—C4 and C5—C6 were restrained to 1.390 (1) Å.The molecular structure of the title molecular salt is illustrated in Fig. 1. The geometric parameters are comparable with those reported for similar structures (Ambalatharasu et al., 2014; Lejon et al., 2006; Smith et al., 2003). The
consists of two independent 2-phenylethanaminium cations and 3-carboxyprop-2-enoate anions. The cations are protonated at amine-N atoms, and in the cations the side chains exhibit anti-conformations [C1—C7—C8—N1 = 176.5 (3) ° and C9—C15—C16—N2 = 179.4 (3) °]. The dihedral angle between the aromatic rings, (C1—C6) and (C9—C14), is 34.0 (3)Å.In the crystal, the molecular structure is stabilized by a medium-strength intramolecular cation-anion N—H···O hydrogen bond (Table 1 and Fig. 2). Adjacent anions and cations are linked by further N—H···O and O—H···O hydrogen bonds into infinite two-dimensional networks parallel to the ab plane (Table 1 and Fig. 2). There are also weak C—H···O hydrogen bonds within the sheets (Table 1).
For the crystal structures of related compounds, see: Ambalatharasu et al. (2014); Lejon et al. (2006); Smith et al. (2003).
The title slat was synthesized by mixing 2-phenylethylamine (1.26 g) and fumaric acid (1.16 g) in methanol-water (1:1) and the single crystals suitable for X-ray diffraction were grown by slow evaporation.
detailsCrystal data, data collection and structure
details are summarized in Table 2. All the H atoms were positioned geometrically and refined using a riding model: O—H = 0.82 Å, N—H = 0.89 Å, C—H = 0.93 - 0.97 Å with Uiso(H) = 1.5Ueq(O,N) for OH and NH3 H atoms and 1.2Ueq(C) for other H atoms. The bond distances C1—C6, C3—C4 and C5—C6 were restrained to 1.390 (1) Å.Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title salt, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. The crystal packing of the title salt viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1) and C-bound H atoms have been omitted for clarity. |
C8H12N+·C4H3O4− | Z = 4 |
Mr = 237.25 | F(000) = 504 |
Triclinic, P1 | Dx = 1.246 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2940 (5) Å | Cell parameters from 7705 reflections |
b = 10.8010 (7) Å | θ = 2.2–27.1° |
c = 12.7470 (8) Å | µ = 0.09 mm−1 |
α = 81.773 (4)° | T = 295 K |
β = 88.907 (5)° | Block, colourless |
γ = 87.396 (4)° | 0.26 × 0.24 × 0.20 mm |
V = 1265.02 (13) Å3 |
Bruker Kappa APEXII CCD diffractometer | 5579 independent reflections |
Radiation source: fine-focus sealed tube | 3453 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω and φ scan | θmax = 27.2°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.976, Tmax = 0.982 | k = −13→13 |
29606 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0955P)2 + 0.6291P] where P = (Fo2 + 2Fc2)/3 |
5579 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 0.39 e Å−3 |
3 restraints | Δρmin = −0.28 e Å−3 |
C8H12N+·C4H3O4− | γ = 87.396 (4)° |
Mr = 237.25 | V = 1265.02 (13) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.2940 (5) Å | Mo Kα radiation |
b = 10.8010 (7) Å | µ = 0.09 mm−1 |
c = 12.7470 (8) Å | T = 295 K |
α = 81.773 (4)° | 0.26 × 0.24 × 0.20 mm |
β = 88.907 (5)° |
Bruker Kappa APEXII CCD diffractometer | 5579 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3453 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.982 | Rint = 0.039 |
29606 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 3 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.39 e Å−3 |
5579 reflections | Δρmin = −0.28 e Å−3 |
309 parameters |
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. 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3953 (4) | 0.2508 (4) | −0.0808 (3) | 0.0901 (13) | |
C2 | 0.3882 (6) | 0.1650 (6) | 0.0060 (4) | 0.1224 (18) | |
H2 | 0.3988 | 0.0810 | −0.0024 | 0.147* | |
C3 | 0.3664 (7) | 0.1939 (8) | 0.1061 (4) | 0.159 (3) | |
H3 | 0.3691 | 0.1307 | 0.1639 | 0.191* | |
C4 | 0.3403 (8) | 0.3176 (9) | 0.1216 (5) | 0.175 (4) | |
H4 | 0.3165 | 0.3389 | 0.1881 | 0.210* | |
C5 | 0.3508 (11) | 0.4049 (10) | 0.0362 (5) | 0.214 (4) | |
H5 | 0.3414 | 0.4888 | 0.0453 | 0.257* | |
C6 | 0.3750 (9) | 0.3752 (5) | −0.0654 (4) | 0.175 (3) | |
H6 | 0.3777 | 0.4386 | −0.1230 | 0.210* | |
C7 | 0.4238 (4) | 0.2131 (5) | −0.1903 (3) | 0.0956 (14) | |
H7A | 0.4901 | 0.2704 | −0.2290 | 0.115* | |
H7B | 0.4695 | 0.1299 | −0.1824 | 0.115* | |
C8 | 0.2922 (3) | 0.2139 (3) | −0.2520 (2) | 0.0587 (8) | |
H8A | 0.2434 | 0.2957 | −0.2558 | 0.070* | |
H8B | 0.2285 | 0.1529 | −0.2152 | 0.070* | |
C9 | −0.0810 (4) | 0.2157 (3) | 0.0186 (3) | 0.0697 (9) | |
C10 | −0.0453 (7) | 0.3273 (4) | −0.0371 (4) | 0.1176 (18) | |
H10 | −0.0028 | 0.3866 | −0.0030 | 0.141* | |
C11 | −0.0731 (8) | 0.3531 (5) | −0.1475 (4) | 0.142 (2) | |
H11 | −0.0477 | 0.4290 | −0.1859 | 0.171* | |
C12 | −0.1362 (7) | 0.2677 (6) | −0.1965 (4) | 0.124 (2) | |
H12 | −0.1611 | 0.2872 | −0.2674 | 0.149* | |
C13 | −0.1632 (6) | 0.1557 (6) | −0.1439 (4) | 0.1197 (19) | |
H13 | −0.1986 | 0.0946 | −0.1798 | 0.144* | |
C14 | −0.1388 (5) | 0.1290 (4) | −0.0354 (3) | 0.0941 (13) | |
H14 | −0.1619 | 0.0514 | 0.0009 | 0.113* | |
C15 | −0.0560 (4) | 0.1892 (4) | 0.1377 (3) | 0.0710 (9) | |
H15A | −0.0280 | 0.1014 | 0.1571 | 0.085* | |
H15B | 0.0224 | 0.2383 | 0.1556 | 0.085* | |
C16 | −0.1874 (3) | 0.2197 (3) | 0.1996 (2) | 0.0553 (7) | |
H16A | −0.2159 | 0.3073 | 0.1793 | 0.066* | |
H16B | −0.2654 | 0.1700 | 0.1819 | 0.066* | |
C17 | 0.9242 (2) | 0.0767 (2) | −0.40812 (17) | 0.0297 (5) | |
C18 | 0.8125 (2) | −0.0199 (2) | −0.39499 (18) | 0.0323 (5) | |
H18 | 0.8431 | −0.1039 | −0.3845 | 0.039* | |
C19 | 0.6736 (2) | 0.0079 (2) | −0.39746 (18) | 0.0314 (5) | |
H19 | 0.6431 | 0.0919 | −0.4074 | 0.038* | |
C20 | 0.5617 (2) | −0.0890 (2) | −0.38511 (17) | 0.0312 (5) | |
C21 | 0.8888 (2) | −0.3850 (2) | −0.43107 (19) | 0.0347 (5) | |
C22 | 0.7711 (2) | −0.4760 (2) | −0.42610 (19) | 0.0365 (5) | |
H22 | 0.7233 | −0.4982 | −0.3619 | 0.044* | |
C23 | 0.7326 (2) | −0.5258 (2) | −0.5096 (2) | 0.0352 (5) | |
H23 | 0.7801 | −0.5022 | −0.5737 | 0.042* | |
C24 | 0.6170 (2) | −0.61804 (19) | −0.50667 (19) | 0.0336 (5) | |
N1 | 0.3190 (2) | 0.1850 (2) | −0.36129 (16) | 0.0433 (5) | |
H1A | 0.3817 | 0.2375 | −0.3943 | 0.065* | |
H1B | 0.2366 | 0.1933 | −0.3966 | 0.065* | |
H1C | 0.3547 | 0.1067 | −0.3585 | 0.065* | |
N2 | −0.1646 (2) | 0.1957 (2) | 0.31577 (16) | 0.0439 (5) | |
H2A | −0.1254 | 0.1189 | 0.3334 | 0.066* | |
H2B | −0.2488 | 0.2021 | 0.3495 | 0.066* | |
H2C | −0.1058 | 0.2515 | 0.3341 | 0.066* | |
O1 | 1.04844 (16) | 0.04879 (15) | −0.37585 (14) | 0.0410 (4) | |
O2 | 0.88262 (16) | 0.18467 (14) | −0.45441 (13) | 0.0388 (4) | |
H2D | 0.9498 | 0.2318 | −0.4584 | 0.058* | |
O3 | 0.60245 (17) | −0.19778 (15) | −0.40468 (15) | 0.0428 (4) | |
O4 | 0.43731 (16) | −0.05906 (15) | −0.35813 (15) | 0.0436 (4) | |
O5 | 0.92154 (17) | −0.33377 (15) | −0.52644 (14) | 0.0421 (4) | |
O6 | 0.9469 (2) | −0.36439 (18) | −0.34987 (15) | 0.0531 (5) | |
O7 | 0.59639 (17) | −0.65424 (16) | −0.59847 (14) | 0.0446 (4) | |
H7 | 0.5322 | −0.7045 | −0.5928 | 0.067* | |
O8 | 0.54969 (18) | −0.65294 (16) | −0.42533 (14) | 0.0459 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.093 (3) | 0.133 (4) | 0.049 (2) | −0.040 (3) | 0.0008 (18) | −0.020 (2) |
C2 | 0.131 (4) | 0.163 (5) | 0.068 (3) | 0.013 (4) | −0.012 (3) | −0.005 (3) |
C3 | 0.155 (6) | 0.270 (10) | 0.044 (3) | −0.002 (6) | −0.010 (3) | 0.007 (4) |
C4 | 0.144 (5) | 0.322 (13) | 0.080 (4) | −0.031 (7) | 0.014 (4) | −0.098 (6) |
C5 | 0.302 (11) | 0.240 (10) | 0.131 (6) | −0.054 (8) | 0.012 (7) | −0.116 (7) |
C6 | 0.287 (10) | 0.155 (6) | 0.094 (4) | −0.065 (6) | −0.012 (5) | −0.041 (4) |
C7 | 0.070 (2) | 0.161 (4) | 0.061 (2) | −0.027 (3) | −0.0009 (18) | −0.029 (2) |
C8 | 0.0557 (17) | 0.076 (2) | 0.0464 (17) | −0.0103 (15) | 0.0040 (13) | −0.0135 (14) |
C9 | 0.082 (2) | 0.080 (2) | 0.0449 (18) | 0.0080 (19) | 0.0043 (16) | −0.0078 (17) |
C10 | 0.197 (6) | 0.087 (3) | 0.068 (3) | −0.021 (3) | 0.015 (3) | −0.005 (2) |
C11 | 0.242 (7) | 0.099 (4) | 0.073 (3) | 0.021 (4) | 0.035 (4) | 0.017 (3) |
C12 | 0.183 (6) | 0.136 (5) | 0.047 (2) | 0.078 (4) | −0.006 (3) | −0.014 (3) |
C13 | 0.154 (5) | 0.143 (5) | 0.070 (3) | 0.037 (4) | −0.025 (3) | −0.049 (3) |
C14 | 0.125 (4) | 0.098 (3) | 0.062 (2) | −0.003 (3) | −0.005 (2) | −0.021 (2) |
C15 | 0.064 (2) | 0.096 (3) | 0.0515 (19) | 0.0026 (18) | 0.0002 (15) | −0.0069 (18) |
C16 | 0.0506 (16) | 0.074 (2) | 0.0401 (15) | −0.0053 (14) | −0.0039 (12) | −0.0041 (14) |
C17 | 0.0272 (11) | 0.0323 (11) | 0.0316 (12) | −0.0103 (9) | 0.0020 (9) | −0.0085 (9) |
C18 | 0.0310 (11) | 0.0294 (11) | 0.0374 (13) | −0.0104 (9) | −0.0003 (9) | −0.0054 (9) |
C19 | 0.0292 (11) | 0.0284 (11) | 0.0375 (12) | −0.0084 (9) | −0.0008 (9) | −0.0050 (9) |
C20 | 0.0271 (11) | 0.0356 (12) | 0.0320 (12) | −0.0116 (9) | −0.0032 (9) | −0.0046 (9) |
C21 | 0.0315 (11) | 0.0289 (11) | 0.0441 (14) | −0.0078 (9) | −0.0032 (10) | −0.0042 (10) |
C22 | 0.0335 (12) | 0.0340 (12) | 0.0419 (13) | −0.0116 (9) | 0.0010 (10) | −0.0016 (10) |
C23 | 0.0286 (11) | 0.0304 (11) | 0.0472 (14) | −0.0102 (9) | 0.0034 (10) | −0.0049 (10) |
C24 | 0.0279 (11) | 0.0275 (11) | 0.0467 (14) | −0.0069 (9) | −0.0003 (10) | −0.0075 (10) |
N1 | 0.0332 (10) | 0.0536 (13) | 0.0438 (12) | −0.0058 (9) | −0.0007 (9) | −0.0078 (10) |
N2 | 0.0374 (11) | 0.0566 (13) | 0.0385 (12) | −0.0057 (10) | −0.0005 (9) | −0.0087 (10) |
O1 | 0.0283 (8) | 0.0406 (9) | 0.0546 (11) | −0.0102 (7) | −0.0051 (7) | −0.0052 (8) |
O2 | 0.0294 (8) | 0.0324 (8) | 0.0538 (11) | −0.0136 (6) | −0.0033 (7) | 0.0006 (7) |
O3 | 0.0306 (8) | 0.0359 (9) | 0.0656 (12) | −0.0113 (7) | 0.0020 (8) | −0.0169 (8) |
O4 | 0.0277 (8) | 0.0411 (9) | 0.0630 (12) | −0.0097 (7) | 0.0057 (7) | −0.0088 (8) |
O5 | 0.0384 (9) | 0.0423 (9) | 0.0452 (10) | −0.0192 (7) | −0.0041 (7) | 0.0014 (8) |
O6 | 0.0586 (11) | 0.0563 (11) | 0.0474 (11) | −0.0278 (9) | −0.0094 (9) | −0.0081 (9) |
O7 | 0.0358 (9) | 0.0456 (10) | 0.0569 (11) | −0.0192 (7) | 0.0046 (8) | −0.0177 (8) |
O8 | 0.0420 (10) | 0.0457 (10) | 0.0510 (11) | −0.0205 (8) | 0.0058 (8) | −0.0055 (8) |
C1—C2 | 1.341 (6) | C15—H15A | 0.9700 |
C1—C6 | 1.3894 (10) | C15—H15B | 0.9700 |
C1—C7 | 1.524 (5) | C16—N2 | 1.484 (3) |
C2—C3 | 1.366 (8) | C16—H16A | 0.9700 |
C2—H2 | 0.9300 | C16—H16B | 0.9700 |
C3—C4 | 1.3888 (10) | C17—O1 | 1.243 (3) |
C3—H3 | 0.9300 | C17—O2 | 1.276 (3) |
C4—C5 | 1.339 (11) | C17—C18 | 1.496 (3) |
C4—H4 | 0.9300 | C18—C19 | 1.312 (3) |
C5—C6 | 1.3902 (10) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.499 (3) |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—C8 | 1.465 (5) | C20—O4 | 1.242 (3) |
C7—H7A | 0.9700 | C20—O3 | 1.276 (3) |
C7—H7B | 0.9700 | C21—O6 | 1.229 (3) |
C8—N1 | 1.485 (4) | C21—O5 | 1.298 (3) |
C8—H8A | 0.9700 | C21—C22 | 1.498 (3) |
C8—H8B | 0.9700 | C22—C23 | 1.322 (3) |
C9—C10 | 1.360 (6) | C22—H22 | 0.9300 |
C9—C14 | 1.373 (5) | C23—C24 | 1.495 (3) |
C9—C15 | 1.524 (4) | C23—H23 | 0.9300 |
C10—C11 | 1.421 (7) | C24—O8 | 1.222 (3) |
C10—H10 | 0.9300 | C24—O7 | 1.306 (3) |
C11—C12 | 1.347 (8) | N1—H1A | 0.8900 |
C11—H11 | 0.9300 | N1—H1B | 0.8900 |
C12—C13 | 1.329 (8) | N1—H1C | 0.8900 |
C12—H12 | 0.9300 | N2—H2A | 0.8900 |
C13—C14 | 1.393 (6) | N2—H2B | 0.8900 |
C13—H13 | 0.9300 | N2—H2C | 0.8900 |
C14—H14 | 0.9300 | O2—H2D | 0.8200 |
C15—C16 | 1.491 (4) | O7—H7 | 0.8200 |
C2—C1—C6 | 116.4 (5) | C16—C15—H15A | 109.2 |
C2—C1—C7 | 121.5 (5) | C9—C15—H15A | 109.2 |
C6—C1—C7 | 122.1 (4) | C16—C15—H15B | 109.2 |
C1—C2—C3 | 123.8 (6) | C9—C15—H15B | 109.2 |
C1—C2—H2 | 118.1 | H15A—C15—H15B | 107.9 |
C3—C2—H2 | 118.1 | N2—C16—C15 | 112.6 (2) |
C2—C3—C4 | 120.0 (6) | N2—C16—H16A | 109.1 |
C2—C3—H3 | 120.0 | C15—C16—H16A | 109.1 |
C4—C3—H3 | 120.0 | N2—C16—H16B | 109.1 |
C5—C4—C3 | 116.9 (6) | C15—C16—H16B | 109.1 |
C5—C4—H4 | 121.6 | H16A—C16—H16B | 107.8 |
C3—C4—H4 | 121.6 | O1—C17—O2 | 124.44 (18) |
C4—C5—C6 | 122.7 (8) | O1—C17—C18 | 119.9 (2) |
C4—C5—H5 | 118.6 | O2—C17—C18 | 115.61 (18) |
C6—C5—H5 | 118.6 | C19—C18—C17 | 123.3 (2) |
C1—C6—C5 | 119.9 (6) | C19—C18—H18 | 118.4 |
C1—C6—H6 | 120.0 | C17—C18—H18 | 118.4 |
C5—C6—H6 | 120.0 | C18—C19—C20 | 123.3 (2) |
C8—C7—C1 | 112.8 (3) | C18—C19—H19 | 118.4 |
C8—C7—H7A | 109.0 | C20—C19—H19 | 118.4 |
C1—C7—H7A | 109.0 | O4—C20—O3 | 124.52 (19) |
C8—C7—H7B | 109.0 | O4—C20—C19 | 119.1 (2) |
C1—C7—H7B | 109.0 | O3—C20—C19 | 116.41 (19) |
H7A—C7—H7B | 107.8 | O6—C21—O5 | 125.11 (19) |
C7—C8—N1 | 113.5 (3) | O6—C21—C22 | 120.8 (2) |
C7—C8—H8A | 108.9 | O5—C21—C22 | 114.1 (2) |
N1—C8—H8A | 108.9 | C23—C22—C21 | 122.5 (2) |
C7—C8—H8B | 108.9 | C23—C22—H22 | 118.8 |
N1—C8—H8B | 108.9 | C21—C22—H22 | 118.8 |
H8A—C8—H8B | 107.7 | C22—C23—C24 | 123.6 (2) |
C10—C9—C14 | 118.2 (4) | C22—C23—H23 | 118.2 |
C10—C9—C15 | 120.1 (4) | C24—C23—H23 | 118.2 |
C14—C9—C15 | 121.7 (3) | O8—C24—O7 | 125.07 (19) |
C9—C10—C11 | 119.9 (5) | O8—C24—C23 | 121.8 (2) |
C9—C10—H10 | 120.0 | O7—C24—C23 | 113.2 (2) |
C11—C10—H10 | 120.0 | C8—N1—H1A | 109.5 |
C12—C11—C10 | 120.0 (5) | C8—N1—H1B | 109.5 |
C12—C11—H11 | 120.0 | H1A—N1—H1B | 109.5 |
C10—C11—H11 | 120.0 | C8—N1—H1C | 109.5 |
C13—C12—C11 | 120.3 (5) | H1A—N1—H1C | 109.5 |
C13—C12—H12 | 119.9 | H1B—N1—H1C | 109.5 |
C11—C12—H12 | 119.9 | C16—N2—H2A | 109.5 |
C12—C13—C14 | 120.5 (5) | C16—N2—H2B | 109.5 |
C12—C13—H13 | 119.8 | H2A—N2—H2B | 109.5 |
C14—C13—H13 | 119.8 | C16—N2—H2C | 109.5 |
C9—C14—C13 | 120.9 (5) | H2A—N2—H2C | 109.5 |
C9—C14—H14 | 119.6 | H2B—N2—H2C | 109.5 |
C13—C14—H14 | 119.6 | C17—O2—H2D | 109.5 |
C16—C15—C9 | 111.8 (3) | C24—O7—H7 | 109.5 |
C6—C1—C2—C3 | −1.7 (8) | C10—C9—C14—C13 | −1.4 (7) |
C7—C1—C2—C3 | 178.4 (5) | C15—C9—C14—C13 | 178.9 (4) |
C1—C2—C3—C4 | 4.4 (10) | C12—C13—C14—C9 | −2.7 (8) |
C2—C3—C4—C5 | −5.9 (12) | C10—C9—C15—C16 | 94.4 (5) |
C3—C4—C5—C6 | 5.1 (14) | C14—C9—C15—C16 | −85.9 (4) |
C2—C1—C6—C5 | 0.7 (10) | C9—C15—C16—N2 | −179.4 (3) |
C7—C1—C6—C5 | −179.3 (6) | O1—C17—C18—C19 | 159.4 (2) |
C4—C5—C6—C1 | −2.6 (14) | O2—C17—C18—C19 | −21.4 (3) |
C2—C1—C7—C8 | 100.0 (5) | C17—C18—C19—C20 | 179.5 (2) |
C6—C1—C7—C8 | −79.9 (6) | C18—C19—C20—O4 | 159.5 (2) |
C1—C7—C8—N1 | 176.5 (3) | C18—C19—C20—O3 | −21.2 (3) |
C14—C9—C10—C11 | 2.3 (8) | O6—C21—C22—C23 | −161.6 (2) |
C15—C9—C10—C11 | −178.0 (5) | O5—C21—C22—C23 | 18.0 (3) |
C9—C10—C11—C12 | 0.8 (9) | C21—C22—C23—C24 | 179.2 (2) |
C10—C11—C12—C13 | −4.9 (10) | C22—C23—C24—O8 | 0.3 (4) |
C11—C12—C13—C14 | 5.9 (9) | C22—C23—C24—O7 | 179.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O4 | 0.89 | 1.92 | 2.805 (3) | 177 |
N1—H1A···O8i | 0.89 | 2.00 | 2.863 (3) | 163 |
N1—H1B···O1ii | 0.89 | 2.38 | 2.992 (2) | 126 |
N1—H1B···O5iii | 0.89 | 2.20 | 2.961 (3) | 143 |
N2—H2A···O1iv | 0.89 | 1.92 | 2.814 (3) | 177 |
N2—H2C···O6iv | 0.89 | 1.99 | 2.863 (3) | 167 |
N2—H2B···O7v | 0.89 | 2.23 | 2.974 (3) | 141 |
N2—H2B···O4vi | 0.89 | 2.38 | 2.992 (2) | 126 |
O2—H2D···O5vii | 0.82 | 1.65 | 2.470 (2) | 176 |
O7—H7···O3viii | 0.82 | 1.68 | 2.494 (2) | 174 |
C7—H7A···O8i | 0.97 | 2.58 | 3.349 (4) | 136 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y, −z−1; (iv) −x+1, −y, −z; (v) x−1, y+1, z+1; (vi) −x, −y, −z; (vii) −x+2, −y, −z−1; (viii) −x+1, −y−1, −z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O4 | 0.89 | 1.92 | 2.805 (3) | 177 |
N1—H1A···O8i | 0.89 | 2.00 | 2.863 (3) | 163 |
N1—H1B···O1ii | 0.89 | 2.38 | 2.992 (2) | 126 |
N1—H1B···O5iii | 0.89 | 2.20 | 2.961 (3) | 143 |
N2—H2A···O1iv | 0.89 | 1.92 | 2.814 (3) | 177 |
N2—H2C···O6iv | 0.89 | 1.99 | 2.863 (3) | 167 |
N2—H2B···O7v | 0.89 | 2.23 | 2.974 (3) | 141 |
N2—H2B···O4vi | 0.89 | 2.38 | 2.992 (2) | 126 |
O2—H2D···O5vii | 0.82 | 1.65 | 2.470 (2) | 176 |
O7—H7···O3viii | 0.82 | 1.68 | 2.494 (2) | 174 |
C7—H7A···O8i | 0.97 | 2.58 | 3.349 (4) | 136 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y, −z−1; (iv) −x+1, −y, −z; (v) x−1, y+1, z+1; (vi) −x, −y, −z; (vii) −x+2, −y, −z−1; (viii) −x+1, −y−1, −z−1. |
Acknowledgements
The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.
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