organic compounds
3-(2,3-Dioxoindolin-1-yl)propanenitrile
aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco, bLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, cX-Ray Structure Analysis Unit, University of Regensburg, D-93053 Regensburg, Germany, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: qachchachi.fatimazahrae@gmail.com
The 11H8N2O2, contains two independent molecules (A and B). Each molecule is build up from fused five- and six-membered rings with the former linked to a cyanoethyl group. The indoline ring and two carbonyl O atoms of each molecule are nearly coplanar, with the largest deviations from the mean planes being 0.0198 (9) (molecule A) and 0.0902 (9) Å (molecule B), each by a carbonyl O atom. The fused ring system is nearly perpendicular to the mean plane passing through the cyanoethyl chains, as indicated by the dihedral angles between them of 69.72 (9) (molecule A) and 69.15 (9)° (molecule B). In the crystal, molecules are linked by C—H⋯O and π–π [intercentroid distance between inversion-related indoline (A) rings = 3.6804 (7) Å] interactions into a double layer that stacks along the a-axis direction.
of the title compound, CCCDC reference: 988036
Related literature
For biological activity of indoline derivatives, see: Bhrigu et al. (2010); Ramachandran (2011); Smitha et al. (2008). For similar structures, see: Qachchachi et al. (2013, 2014).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 988036
10.1107/S1600536814003985/tk5297sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003985/tk5297Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003985/tk5297Isup3.cml
Heterocyclic compounds are acquiring more importance in recent years because of their broad pharmacological activities. Isatin and its derivatives are used in organic synthesis and in evaluating new product possessing different biological activities. Isatin derivatives have been reported to show considerable pharmacological actions such as, anti-convulsant, anti-anixity and anti-psychoactives activities (Bhrigu et al., 2010; Ramachandran, 2011; Smitha et al., 2008). As a continuation of our research work devoted to the development of isatin derivatives (Qachchachi et al., 2013; Qachchachi et al., 2014), we report the synthesis of new indoline-2,3-dione derivative by action of alkyl halides to explore other applications.
Each independent molecule of title compound is build up from a fused five- and six-membered rings linked, to a cyanoethyl chain and to two carbonyl oxygen atoms as shown in Fig. 1. The indoline ring and the two ketonic oxygen atoms are nearly coplanar, with the largest deviation from the mean plane being 0.0198 (9) Å for O1 atom, and 0.0902 (9) Å for the O4 atom, respectively, in the first and second molecule. The fused ring system planes, (N1, C1 to C8) and (N3, C12 to C19), are nearly perpendicular to the mean plane passing through the cyanoethyl chains (N2, C9–C11 and N4, C20–C22) as indicated by the dihedral angles between them of 69.47 (9) and 69.06 (9)°, respectviely. The two molecules in the
have a similar conformation, except the cyanoethyl group orientation as shown in Fig. 2.In the crystal, the molecules are linked by C—H···O hydrogen bonds, Table 1, and π—π interactions between the five- and six-membered rings of the N1-containing molecule [inter-centroid distance = 3.6804 (7) Å for 1-x, 1-y, 2-z] to form double layers that stack along the a axis.
To a solution of isatin (0.5 g, 3.4 mmol) dissolved in DMF (30 ml) was added, potassium carbonate (0.61 g, 4.4 mmol), a catalytic quantity of tetra-n-butylammonium bromide (0.1 g, 0.4 mmol) and 3-bromopropanenitrile (0.3 ml, 3.7 mmol). The mixture was stirred for 48 h; the reaction was monitored by thin layer
The mixture was filtered and the solvent removed under vacuum. The solid obtained was recrystallized from ethanol to afford the title compound as orange crystals (yield: 52%; M.pt: 383 K).Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).Fig. 1. Molecular plot the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. View showing the fitting of the two molecules in the asymmetric unit. |
C11H8N2O2 | Z = 4 |
Mr = 200.19 | F(000) = 416 |
Triclinic, P1 | Dx = 1.438 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 7.1967 (2) Å | Cell parameters from 4004 reflections |
b = 9.9909 (3) Å | θ = 4.6–73.3° |
c = 13.5534 (5) Å | µ = 0.84 mm−1 |
α = 77.508 (3)° | T = 123 K |
β = 81.551 (3)° | Plate, orange |
γ = 77.717 (3)° | 0.26 × 0.17 × 0.12 mm |
V = 924.44 (5) Å3 |
Agilent SuperNova (Single source at offset, Atlas) diffractometer | 3546 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 3292 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.013 |
Detector resolution: 10.3546 pixels mm-1 | θmax = 73.7°, θmin = 4.6° |
ω scans | h = −8→8 |
Absorption correction: analytical (Clark & Reid, 1995) | k = −12→9 |
Tmin = 0.827, Tmax = 0.917 | l = −16→16 |
5751 measured reflections |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.2333P] where P = (Fo2 + 2Fc2)/3 |
3546 reflections | (Δ/σ)max = 0.001 |
271 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C11H8N2O2 | γ = 77.717 (3)° |
Mr = 200.19 | V = 924.44 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.1967 (2) Å | Cu Kα radiation |
b = 9.9909 (3) Å | µ = 0.84 mm−1 |
c = 13.5534 (5) Å | T = 123 K |
α = 77.508 (3)° | 0.26 × 0.17 × 0.12 mm |
β = 81.551 (3)° |
Agilent SuperNova (Single source at offset, Atlas) diffractometer | 3546 independent reflections |
Absorption correction: analytical (Clark & Reid, 1995) | 3292 reflections with I > 2σ(I) |
Tmin = 0.827, Tmax = 0.917 | Rint = 0.013 |
5751 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.19 e Å−3 |
3546 reflections | Δρmin = −0.28 e Å−3 |
271 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(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 | 0.35182 (15) | 0.75842 (11) | 1.04434 (8) | 0.0189 (2) | |
C2 | 0.27845 (15) | 0.61738 (11) | 1.07606 (8) | 0.0193 (2) | |
C3 | 0.27526 (15) | 0.57304 (11) | 0.98035 (8) | 0.0181 (2) | |
C4 | 0.33583 (14) | 0.67561 (11) | 0.90158 (8) | 0.0171 (2) | |
C5 | 0.34919 (16) | 0.66466 (11) | 0.80081 (8) | 0.0196 (2) | |
H5 | 0.3914 | 0.7340 | 0.7475 | 0.023* | |
C6 | 0.29746 (16) | 0.54636 (11) | 0.78129 (9) | 0.0213 (2) | |
H6 | 0.3044 | 0.5357 | 0.7128 | 0.026* | |
C7 | 0.23621 (16) | 0.44382 (11) | 0.85865 (9) | 0.0218 (2) | |
H7 | 0.2015 | 0.3652 | 0.8423 | 0.026* | |
C8 | 0.22547 (15) | 0.45570 (11) | 0.95987 (9) | 0.0201 (2) | |
H8 | 0.1853 | 0.3857 | 1.0133 | 0.024* | |
C9 | 0.44795 (16) | 0.90577 (11) | 0.87921 (8) | 0.0210 (2) | |
H9A | 0.5298 | 0.8784 | 0.8187 | 0.025* | |
H9B | 0.5278 | 0.9390 | 0.9189 | 0.025* | |
C10 | 0.28577 (18) | 1.02563 (12) | 0.84414 (9) | 0.0253 (2) | |
H10A | 0.3403 | 1.0976 | 0.7927 | 0.030* | |
H10B | 0.1974 | 0.9897 | 0.8113 | 0.030* | |
C11 | 0.17723 (17) | 1.09045 (11) | 0.92779 (9) | 0.0241 (2) | |
C12 | 0.35805 (16) | 0.79086 (12) | 1.50595 (9) | 0.0231 (2) | |
C13 | 0.30355 (17) | 0.93949 (12) | 1.53235 (9) | 0.0232 (2) | |
C14 | 0.22133 (16) | 1.02896 (12) | 1.44313 (9) | 0.0220 (2) | |
C15 | 0.22224 (15) | 0.94421 (12) | 1.37283 (8) | 0.0204 (2) | |
C16 | 0.15683 (16) | 1.00021 (12) | 1.27902 (9) | 0.0232 (2) | |
H16 | 0.1550 | 0.9430 | 1.2317 | 0.028* | |
C17 | 0.09340 (17) | 1.14485 (13) | 1.25670 (9) | 0.0265 (3) | |
H17 | 0.0477 | 1.1861 | 1.1927 | 0.032* | |
C18 | 0.09507 (18) | 1.23038 (13) | 1.32516 (10) | 0.0285 (3) | |
H18 | 0.0522 | 1.3283 | 1.3072 | 0.034* | |
C19 | 0.15933 (17) | 1.17260 (13) | 1.41961 (9) | 0.0262 (3) | |
H19 | 0.1609 | 1.2298 | 1.4670 | 0.031* | |
C20 | 0.35533 (17) | 0.68910 (12) | 1.35580 (9) | 0.0233 (2) | |
H20A | 0.4907 | 0.6454 | 1.3637 | 0.028* | |
H20B | 0.3452 | 0.7277 | 1.2827 | 0.028* | |
C21 | 0.23180 (18) | 0.57728 (12) | 1.39112 (9) | 0.0264 (3) | |
H21A | 0.2874 | 0.4972 | 1.3572 | 0.032* | |
H21B | 0.2345 | 0.5436 | 1.4653 | 0.032* | |
C22 | 0.03284 (19) | 0.62732 (13) | 1.36936 (9) | 0.0283 (3) | |
N1 | 0.38031 (13) | 0.78390 (9) | 0.94098 (7) | 0.01830 (19) | |
N2 | 0.09333 (16) | 1.14251 (11) | 0.99259 (9) | 0.0312 (2) | |
N3 | 0.30023 (14) | 0.80320 (10) | 1.41232 (7) | 0.0216 (2) | |
N4 | −0.12343 (17) | 0.66540 (14) | 1.35365 (10) | 0.0410 (3) | |
O1 | 0.37857 (12) | 0.82987 (8) | 1.10106 (6) | 0.02410 (18) | |
O2 | 0.23689 (12) | 0.56414 (9) | 1.16318 (6) | 0.02605 (19) | |
O3 | 0.33463 (13) | 0.96621 (9) | 1.61077 (6) | 0.0300 (2) | |
O4 | 0.43958 (13) | 0.68559 (9) | 1.55714 (6) | 0.0300 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0187 (5) | 0.0186 (5) | 0.0195 (5) | −0.0013 (4) | −0.0037 (4) | −0.0046 (4) |
C2 | 0.0190 (5) | 0.0186 (5) | 0.0202 (5) | −0.0023 (4) | −0.0033 (4) | −0.0042 (4) |
C3 | 0.0168 (5) | 0.0180 (5) | 0.0191 (5) | −0.0017 (4) | −0.0027 (4) | −0.0038 (4) |
C4 | 0.0159 (5) | 0.0152 (5) | 0.0207 (5) | −0.0010 (4) | −0.0035 (4) | −0.0052 (4) |
C5 | 0.0221 (5) | 0.0176 (5) | 0.0187 (5) | −0.0024 (4) | −0.0028 (4) | −0.0037 (4) |
C6 | 0.0239 (5) | 0.0209 (5) | 0.0202 (5) | −0.0003 (4) | −0.0054 (4) | −0.0079 (4) |
C7 | 0.0230 (5) | 0.0171 (5) | 0.0278 (6) | −0.0029 (4) | −0.0061 (4) | −0.0081 (4) |
C8 | 0.0194 (5) | 0.0167 (5) | 0.0238 (5) | −0.0030 (4) | −0.0027 (4) | −0.0033 (4) |
C9 | 0.0238 (5) | 0.0188 (5) | 0.0221 (5) | −0.0083 (4) | 0.0004 (4) | −0.0052 (4) |
C10 | 0.0350 (6) | 0.0189 (5) | 0.0230 (6) | −0.0065 (5) | −0.0061 (5) | −0.0029 (4) |
C11 | 0.0257 (6) | 0.0150 (5) | 0.0318 (6) | −0.0062 (4) | −0.0057 (5) | −0.0011 (5) |
C12 | 0.0247 (6) | 0.0265 (6) | 0.0187 (5) | −0.0073 (4) | 0.0000 (4) | −0.0044 (4) |
C13 | 0.0240 (6) | 0.0278 (6) | 0.0195 (5) | −0.0086 (4) | 0.0007 (4) | −0.0064 (4) |
C14 | 0.0207 (5) | 0.0262 (6) | 0.0205 (5) | −0.0072 (4) | 0.0005 (4) | −0.0065 (4) |
C15 | 0.0173 (5) | 0.0233 (5) | 0.0210 (5) | −0.0057 (4) | 0.0011 (4) | −0.0053 (4) |
C16 | 0.0199 (5) | 0.0300 (6) | 0.0204 (5) | −0.0040 (4) | −0.0014 (4) | −0.0072 (4) |
C17 | 0.0213 (6) | 0.0315 (6) | 0.0242 (6) | −0.0020 (5) | −0.0034 (4) | −0.0024 (5) |
C18 | 0.0253 (6) | 0.0238 (6) | 0.0347 (7) | −0.0011 (5) | −0.0042 (5) | −0.0049 (5) |
C19 | 0.0247 (6) | 0.0264 (6) | 0.0293 (6) | −0.0054 (4) | −0.0007 (5) | −0.0103 (5) |
C20 | 0.0259 (6) | 0.0241 (6) | 0.0208 (5) | −0.0034 (4) | −0.0011 (4) | −0.0083 (4) |
C21 | 0.0359 (7) | 0.0226 (6) | 0.0217 (6) | −0.0065 (5) | −0.0048 (5) | −0.0042 (4) |
C22 | 0.0360 (7) | 0.0307 (6) | 0.0232 (6) | −0.0137 (5) | 0.0018 (5) | −0.0117 (5) |
N1 | 0.0218 (4) | 0.0158 (4) | 0.0187 (4) | −0.0050 (3) | −0.0024 (3) | −0.0048 (3) |
N2 | 0.0303 (5) | 0.0220 (5) | 0.0406 (6) | −0.0057 (4) | 0.0009 (5) | −0.0070 (5) |
N3 | 0.0259 (5) | 0.0222 (5) | 0.0178 (4) | −0.0052 (4) | −0.0020 (4) | −0.0056 (4) |
N4 | 0.0322 (7) | 0.0549 (8) | 0.0445 (7) | −0.0133 (5) | −0.0001 (5) | −0.0254 (6) |
O1 | 0.0306 (4) | 0.0231 (4) | 0.0219 (4) | −0.0061 (3) | −0.0050 (3) | −0.0089 (3) |
O2 | 0.0318 (4) | 0.0277 (4) | 0.0181 (4) | −0.0077 (3) | −0.0017 (3) | −0.0019 (3) |
O3 | 0.0380 (5) | 0.0351 (5) | 0.0205 (4) | −0.0101 (4) | −0.0033 (4) | −0.0095 (4) |
O4 | 0.0379 (5) | 0.0287 (4) | 0.0216 (4) | −0.0030 (4) | −0.0056 (4) | −0.0026 (3) |
C1—O1 | 1.2153 (14) | C12—O4 | 1.2137 (15) |
C1—N1 | 1.3612 (14) | C12—N3 | 1.3655 (15) |
C1—C2 | 1.5610 (15) | C12—C13 | 1.5581 (16) |
C2—O2 | 1.2079 (14) | C13—O3 | 1.2120 (15) |
C2—C3 | 1.4633 (15) | C13—C14 | 1.4591 (17) |
C3—C8 | 1.3886 (15) | C14—C19 | 1.3898 (17) |
C3—C4 | 1.4000 (15) | C14—C15 | 1.4035 (16) |
C4—C5 | 1.3812 (15) | C15—C16 | 1.3811 (16) |
C4—N1 | 1.4163 (13) | C15—N3 | 1.4184 (15) |
C5—C6 | 1.3990 (15) | C16—C17 | 1.3997 (17) |
C5—H5 | 0.9500 | C16—H16 | 0.9500 |
C6—C7 | 1.3910 (16) | C17—C18 | 1.3935 (18) |
C6—H6 | 0.9500 | C17—H17 | 0.9500 |
C7—C8 | 1.3919 (16) | C18—C19 | 1.3880 (18) |
C7—H7 | 0.9500 | C18—H18 | 0.9500 |
C8—H8 | 0.9500 | C19—H19 | 0.9500 |
C9—N1 | 1.4533 (14) | C20—N3 | 1.4627 (14) |
C9—C10 | 1.5311 (16) | C20—C21 | 1.5277 (16) |
C9—H9A | 0.9900 | C20—H20A | 0.9900 |
C9—H9B | 0.9900 | C20—H20B | 0.9900 |
C10—C11 | 1.4686 (17) | C21—C22 | 1.4638 (19) |
C10—H10A | 0.9900 | C21—H21A | 0.9900 |
C10—H10B | 0.9900 | C21—H21B | 0.9900 |
C11—N2 | 1.1465 (17) | C22—N4 | 1.1437 (18) |
O1—C1—N1 | 127.39 (10) | O3—C13—C14 | 131.27 (11) |
O1—C1—C2 | 126.58 (10) | O3—C13—C12 | 123.77 (11) |
N1—C1—C2 | 106.03 (9) | C14—C13—C12 | 104.90 (9) |
O2—C2—C3 | 131.42 (10) | C19—C14—C15 | 121.09 (11) |
O2—C2—C1 | 123.65 (10) | C19—C14—C13 | 131.24 (11) |
C3—C2—C1 | 104.94 (9) | C15—C14—C13 | 107.57 (10) |
C8—C3—C4 | 120.97 (10) | C16—C15—C14 | 121.14 (11) |
C8—C3—C2 | 131.70 (10) | C16—C15—N3 | 128.32 (10) |
C4—C3—C2 | 107.33 (9) | C14—C15—N3 | 110.52 (10) |
C5—C4—C3 | 121.79 (10) | C15—C16—C17 | 117.12 (11) |
C5—C4—N1 | 127.51 (10) | C15—C16—H16 | 121.4 |
C3—C4—N1 | 110.69 (9) | C17—C16—H16 | 121.4 |
C4—C5—C6 | 116.62 (10) | C18—C17—C16 | 122.25 (11) |
C4—C5—H5 | 121.7 | C18—C17—H17 | 118.9 |
C6—C5—H5 | 121.7 | C16—C17—H17 | 118.9 |
C7—C6—C5 | 122.30 (10) | C19—C18—C17 | 120.05 (11) |
C7—C6—H6 | 118.9 | C19—C18—H18 | 120.0 |
C5—C6—H6 | 118.9 | C17—C18—H18 | 120.0 |
C6—C7—C8 | 120.37 (10) | C18—C19—C14 | 118.32 (11) |
C6—C7—H7 | 119.8 | C18—C19—H19 | 120.8 |
C8—C7—H7 | 119.8 | C14—C19—H19 | 120.8 |
C3—C8—C7 | 117.95 (10) | N3—C20—C21 | 112.93 (9) |
C3—C8—H8 | 121.0 | N3—C20—H20A | 109.0 |
C7—C8—H8 | 121.0 | C21—C20—H20A | 109.0 |
N1—C9—C10 | 113.21 (9) | N3—C20—H20B | 109.0 |
N1—C9—H9A | 108.9 | C21—C20—H20B | 109.0 |
C10—C9—H9A | 108.9 | H20A—C20—H20B | 107.8 |
N1—C9—H9B | 108.9 | C22—C21—C20 | 113.17 (10) |
C10—C9—H9B | 108.9 | C22—C21—H21A | 108.9 |
H9A—C9—H9B | 107.7 | C20—C21—H21A | 108.9 |
C11—C10—C9 | 112.92 (10) | C22—C21—H21B | 108.9 |
C11—C10—H10A | 109.0 | C20—C21—H21B | 108.9 |
C9—C10—H10A | 109.0 | H21A—C21—H21B | 107.8 |
C11—C10—H10B | 109.0 | N4—C22—C21 | 179.04 (15) |
C9—C10—H10B | 109.0 | C1—N1—C4 | 111.00 (9) |
H10A—C10—H10B | 107.8 | C1—N1—C9 | 124.54 (9) |
N2—C11—C10 | 179.16 (13) | C4—N1—C9 | 124.46 (9) |
O4—C12—N3 | 126.70 (11) | C12—N3—C15 | 110.66 (9) |
O4—C12—C13 | 127.01 (10) | C12—N3—C20 | 121.49 (10) |
N3—C12—C13 | 106.28 (10) | C15—N3—C20 | 126.46 (9) |
O1—C1—C2—O2 | 1.10 (18) | C19—C14—C15—N3 | 177.06 (10) |
N1—C1—C2—O2 | −179.24 (10) | C13—C14—C15—N3 | 0.37 (13) |
O1—C1—C2—C3 | −178.80 (11) | C14—C15—C16—C17 | 1.18 (16) |
N1—C1—C2—C3 | 0.85 (11) | N3—C15—C16—C17 | −177.39 (11) |
O2—C2—C3—C8 | −0.7 (2) | C15—C16—C17—C18 | 0.00 (17) |
C1—C2—C3—C8 | 179.16 (11) | C16—C17—C18—C19 | −0.66 (19) |
O2—C2—C3—C4 | 179.23 (12) | C17—C18—C19—C14 | 0.14 (18) |
C1—C2—C3—C4 | −0.87 (11) | C15—C14—C19—C18 | 1.04 (18) |
C8—C3—C4—C5 | −0.18 (16) | C13—C14—C19—C18 | 176.84 (12) |
C2—C3—C4—C5 | 179.85 (10) | N3—C20—C21—C22 | 66.72 (13) |
C8—C3—C4—N1 | −179.42 (9) | O1—C1—N1—C4 | 179.14 (11) |
C2—C3—C4—N1 | 0.61 (12) | C2—C1—N1—C4 | −0.51 (11) |
C3—C4—C5—C6 | 0.55 (16) | O1—C1—N1—C9 | −0.68 (18) |
N1—C4—C5—C6 | 179.66 (10) | C2—C1—N1—C9 | 179.67 (9) |
C4—C5—C6—C7 | −0.27 (16) | C5—C4—N1—C1 | −179.22 (10) |
C5—C6—C7—C8 | −0.40 (17) | C3—C4—N1—C1 | −0.04 (12) |
C4—C3—C8—C7 | −0.50 (16) | C5—C4—N1—C9 | 0.60 (17) |
C2—C3—C8—C7 | 179.47 (11) | C3—C4—N1—C9 | 179.78 (9) |
C6—C7—C8—C3 | 0.77 (16) | C10—C9—N1—C1 | −93.32 (12) |
N1—C9—C10—C11 | 69.07 (12) | C10—C9—N1—C4 | 86.88 (12) |
O4—C12—C13—O3 | −1.59 (19) | O4—C12—N3—C15 | −175.78 (11) |
N3—C12—C13—O3 | 179.97 (11) | C13—C12—N3—C15 | 2.67 (12) |
O4—C12—C13—C14 | 176.08 (12) | O4—C12—N3—C20 | −8.40 (18) |
N3—C12—C13—C14 | −2.37 (12) | C13—C12—N3—C20 | 170.05 (9) |
O3—C13—C14—C19 | 2.4 (2) | C16—C15—N3—C12 | 176.66 (11) |
C12—C13—C14—C19 | −175.05 (12) | C14—C15—N3—C12 | −2.04 (13) |
O3—C13—C14—C15 | 178.60 (12) | C16—C15—N3—C20 | 10.05 (19) |
C12—C13—C14—C15 | 1.18 (12) | C14—C15—N3—C20 | −168.64 (10) |
C19—C14—C15—C16 | −1.74 (17) | C21—C20—N3—C12 | 80.57 (13) |
C13—C14—C15—C16 | −178.43 (10) | C21—C20—N3—C15 | −114.16 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O1 | 0.95 | 2.50 | 3.2787 (14) | 139 |
C20—H20B···O1 | 0.99 | 2.45 | 3.4287 (14) | 170 |
C6—H6···O4i | 0.95 | 2.51 | 3.1740 (14) | 127 |
C5—H5···O3i | 0.95 | 2.63 | 3.5085 (14) | 153 |
C9—H9B···O1ii | 0.99 | 2.49 | 3.2269 (13) | 131 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O1 | 0.95 | 2.50 | 3.2787 (14) | 139 |
C20—H20B···O1 | 0.99 | 2.45 | 3.4287 (14) | 170 |
C6—H6···O4i | 0.95 | 2.51 | 3.1740 (14) | 127 |
C5—H5···O3i | 0.95 | 2.63 | 3.5085 (14) | 153 |
C9—H9B···O1ii | 0.99 | 2.49 | 3.2269 (13) | 131 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, −z+2. |
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