organic compounds
H-indole-3-carbonyl)-1′-methyl-2-oxo-4′-(4-oxo-4H-chromen-3-yl)spiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile
of 3′-(1aDepartment of Physics, Queen Mary's College (Autonomous), Chennai 600 004, India, bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and cIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India
*Correspondence e-mail: aspandian59@gmail.com
In the title compound, C31H22N4O4, the pyrrolidine ring adopts a twist conformation on the N—CH2 bond. The indolin-2-one and the 1H-indole rings are nearly planar (r.m.s. deviations = 0.06 and 0.011 Å, respectively) and are inclined to one another by 34.19 (9)°. The chromene ring system is also nearly planar (r.m.s. deviation = 0.029 Å). It is almost normal to the 1H-indole ring system, with a dihedral angle of 88.71 (8)°, and is inclined to the indolin-2-one ring system by 72.76 (8)°. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming slabs parallel to (10-1). The slabs are linked by C—H⋯O hydrogen bonds, forming a three-dimensional structure.
Keywords: crystal structure; indole; pyrrolidine; chromen; spiro; carbonitrile; hydrogen bonding.
CCDC reference: 1433172
1. Related literature
For the biological activities of indole derivatives, see: Macor et al. (1992); Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For the structure of a very similar compound, see: Ramesh et al. (2009).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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 and PLATON.
Supporting information
CCDC reference: 1433172
https://doi.org/10.1107/S2056989015020174/su5215sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020174/su5215Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015020174/su5215Isup3.cml
The chemistry of indole has been of increasing interest, since several compounds of this type possess diverse biological activities (Macor et al., 1992). These derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). Some of the indole
extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).The geometric parameters of the title molecule (Fig. 1) agree well with those reported for a similar compound, 1'-methyl-2,2''-dioxoindoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-indoline-4',4'-dicarbonitrile (Ramesh et al., 2009). The pyrrolidine ring (N2/C10/C11/C13/C21) adopts a twist conformation on bond N2—C21: puckering parameters and the asymmetry parameters for this ring are q2 = 0.411 (2) Å, φ2 = 160.3 (3)° nd ΔCs(C11) = 1.3 (2)°. Both indole rings, (N3/24–31) and (N4/C13—C20), are planar [maximum deviations of 0.013 Å for C27 and 0.080 (1) Å for C13 in the two rings] and are oriented at a dihedral angle of 34.19 (9)°. The sum of the bond angles around atom N2 of the central pyrrolidine ring is 337° as expected for sp3 hybridization.
In the crystal, molecules are linked by N—H···O hydrogen bonds forming slabs parallel to (101). The slabs are linked via C—H···O hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 2).
A mixture of isatin2a-f (1.0 mmol), sarcosine3 (1.1 mmol) and (E)-2-(1H-indole -3-carbonyl)-3-(4-oxo-4H-chromen-3-yl)acrylonitrile 1 (1.2 mmol) in methanol was stirred at room temperature for 120 min. The solid precipitated during the reaction mixture was filtered and dried under vacuum to obtain spirooxindoles5a-f in crude form. The resulting crude product was purified by flash
(mesh 100–200) using hexane/EtOAC (7:3). The solid single product was finally recrystallized from ethanol, giving title compound in good yield as colourless block-like crystals.The chemistry of indole has been of increasing interest, since several compounds of this type possess diverse biological activities (Macor et al., 1992). These derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). Some of the indole
extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).The geometric parameters of the title molecule (Fig. 1) agree well with those reported for a similar compound, 1'-methyl-2,2''-dioxoindoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-indoline-4',4'-dicarbonitrile (Ramesh et al., 2009). The pyrrolidine ring (N2/C10/C11/C13/C21) adopts a twist conformation on bond N2—C21: puckering parameters and the asymmetry parameters for this ring are q2 = 0.411 (2) Å, φ2 = 160.3 (3)° nd ΔCs(C11) = 1.3 (2)°. Both indole rings, (N3/24–31) and (N4/C13—C20), are planar [maximum deviations of 0.013 Å for C27 and 0.080 (1) Å for C13 in the two rings] and are oriented at a dihedral angle of 34.19 (9)°. The sum of the bond angles around atom N2 of the central pyrrolidine ring is 337° as expected for sp3 hybridization.
In the crystal, molecules are linked by N—H···O hydrogen bonds forming slabs parallel to (101). The slabs are linked via C—H···O hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 2).
For the biological activities of indole derivatives, see: Macor et al. (1992); Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For the structure of a very similar compound, see: Ramesh et al. (2009).
A mixture of isatin2a-f (1.0 mmol), sarcosine3 (1.1 mmol) and (E)-2-(1H-indole -3-carbonyl)-3-(4-oxo-4H-chromen-3-yl)acrylonitrile 1 (1.2 mmol) in methanol was stirred at room temperature for 120 min. The solid precipitated during the reaction mixture was filtered and dried under vacuum to obtain spirooxindoles5a-f in crude form. The resulting crude product was purified by flash
(mesh 100–200) using hexane/EtOAC (7:3). The solid single product was finally recrystallized from ethanol, giving title compound in good yield as colourless block-like crystals. detailsCrystal data, data collection and structure
details are summarized in Table 2. N and C-bound H atoms were positioned geometrically (N—H = 0.86 Å, C–H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(N,C) for other H atoms.Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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).C31H22N4O4 | F(000) = 1072 |
Mr = 514.53 | Dx = 1.388 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybn | Cell parameters from 4241 reflections |
a = 13.0401 (5) Å | θ = 1.8–25.0° |
b = 14.9139 (6) Å | µ = 0.09 mm−1 |
c = 13.7161 (5) Å | T = 293 K |
β = 112.603 (2)° | Block, colourless |
V = 2462.60 (16) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 4341 independent reflections |
Radiation source: fine-focus sealed tube | 3234 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω and φ scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −14→15 |
Tmin = 0.969, Tmax = 0.974 | k = −17→17 |
16591 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0575P)2 + 1.2814P] where P = (Fo2 + 2Fc2)/3 |
4329 reflections | (Δ/σ)max < 0.001 |
353 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C31H22N4O4 | V = 2462.60 (16) Å3 |
Mr = 514.53 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.0401 (5) Å | µ = 0.09 mm−1 |
b = 14.9139 (6) Å | T = 293 K |
c = 13.7161 (5) Å | 0.35 × 0.30 × 0.30 mm |
β = 112.603 (2)° |
Bruker Kappa APEXII CCD diffractometer | 4341 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 3234 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.974 | Rint = 0.030 |
16591 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.29 e Å−3 |
4329 reflections | Δρmin = −0.18 e Å−3 |
353 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 > σ(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 | 0.2880 (2) | 0.25426 (16) | −0.10673 (17) | 0.0378 (6) | |
H1 | 0.2737 | 0.3152 | −0.1193 | 0.045* | |
C2 | 0.36735 (18) | 0.12268 (16) | −0.14083 (15) | 0.0353 (5) | |
C3 | 0.4277 (2) | 0.08350 (19) | −0.19416 (18) | 0.0467 (6) | |
H3 | 0.4542 | 0.1178 | −0.2361 | 0.056* | |
C4 | 0.4468 (2) | −0.00645 (19) | −0.18327 (19) | 0.0517 (7) | |
H4 | 0.4867 | −0.0338 | −0.2186 | 0.062* | |
C5 | 0.4078 (2) | −0.05821 (18) | −0.1203 (2) | 0.0498 (7) | |
H5 | 0.4201 | −0.1198 | −0.1153 | 0.060* | |
C6 | 0.35133 (19) | −0.01845 (17) | −0.06596 (19) | 0.0427 (6) | |
H6 | 0.3269 | −0.0529 | −0.0226 | 0.051* | |
C7 | 0.33001 (17) | 0.07404 (15) | −0.07526 (15) | 0.0325 (5) | |
C8 | 0.27094 (18) | 0.11941 (15) | −0.01806 (15) | 0.0340 (5) | |
C9 | 0.24912 (18) | 0.21424 (15) | −0.04083 (15) | 0.0307 (5) | |
C10 | 0.18396 (18) | 0.26261 (15) | 0.01285 (15) | 0.0321 (5) | |
H10 | 0.1243 | 0.2227 | 0.0130 | 0.039* | |
C11 | 0.25597 (17) | 0.28881 (15) | 0.13121 (15) | 0.0298 (5) | |
C12 | 0.3687 (2) | 0.25089 (15) | 0.16436 (16) | 0.0338 (5) | |
C13 | 0.26070 (17) | 0.39617 (15) | 0.13015 (15) | 0.0315 (5) | |
C14 | 0.1881 (2) | 0.43664 (17) | 0.18886 (18) | 0.0424 (6) | |
C15 | 0.3657 (2) | 0.48427 (17) | 0.27711 (19) | 0.0464 (6) | |
C16 | 0.4568 (3) | 0.52655 (19) | 0.3503 (2) | 0.0641 (9) | |
H16 | 0.4530 | 0.5548 | 0.4093 | 0.077* | |
C17 | 0.5530 (3) | 0.5251 (2) | 0.3323 (3) | 0.0734 (10) | |
H17 | 0.6159 | 0.5529 | 0.3804 | 0.088* | |
C18 | 0.5596 (2) | 0.4835 (2) | 0.2449 (3) | 0.0683 (9) | |
H18 | 0.6256 | 0.4856 | 0.2338 | 0.082* | |
C19 | 0.4675 (2) | 0.43842 (19) | 0.1731 (2) | 0.0507 (7) | |
H19 | 0.4715 | 0.4095 | 0.1146 | 0.061* | |
C20 | 0.37124 (19) | 0.43801 (16) | 0.19138 (17) | 0.0378 (6) | |
C21 | 0.13173 (19) | 0.35150 (16) | −0.03531 (16) | 0.0382 (6) | |
H21A | 0.1129 | 0.3522 | −0.1110 | 0.046* | |
H21B | 0.0653 | 0.3635 | −0.0217 | 0.046* | |
C22 | 0.1867 (2) | 0.50981 (18) | −0.0085 (2) | 0.0581 (8) | |
H22A | 0.1694 | 0.5195 | −0.0823 | 0.087* | |
H22B | 0.2473 | 0.5479 | 0.0325 | 0.087* | |
H22C | 0.1227 | 0.5236 | 0.0073 | 0.087* | |
C23 | 0.19977 (18) | 0.25368 (15) | 0.20664 (16) | 0.0331 (5) | |
C24 | 0.25979 (18) | 0.25638 (15) | 0.32050 (16) | 0.0339 (5) | |
C25 | 0.21092 (18) | 0.23643 (15) | 0.39638 (16) | 0.0338 (5) | |
C26 | 0.1073 (2) | 0.20842 (18) | 0.39024 (19) | 0.0472 (6) | |
H26 | 0.0500 | 0.1987 | 0.3251 | 0.057* | |
C27 | 0.0911 (2) | 0.1953 (2) | 0.4831 (2) | 0.0603 (8) | |
H27 | 0.0222 | 0.1757 | 0.4799 | 0.072* | |
C28 | 0.1754 (2) | 0.2107 (2) | 0.5811 (2) | 0.0555 (7) | |
H28 | 0.1615 | 0.2020 | 0.6421 | 0.067* | |
C29 | 0.2784 (2) | 0.23842 (17) | 0.58952 (18) | 0.0456 (6) | |
H29 | 0.3350 | 0.2487 | 0.6549 | 0.055* | |
C30 | 0.29469 (19) | 0.25050 (16) | 0.49630 (16) | 0.0359 (5) | |
C31 | 0.36911 (19) | 0.27949 (17) | 0.37844 (17) | 0.0412 (6) | |
H31 | 0.4208 | 0.2950 | 0.3499 | 0.049* | |
N1 | 0.45588 (18) | 0.22200 (15) | 0.18987 (16) | 0.0502 (6) | |
N2 | 0.21796 (16) | 0.41585 (13) | 0.01775 (13) | 0.0390 (5) | |
N3 | 0.38947 (16) | 0.27611 (14) | 0.48210 (14) | 0.0430 (5) | |
H3A | 0.4522 | 0.2881 | 0.5320 | 0.052* | |
N4 | 0.25757 (18) | 0.48177 (15) | 0.27375 (16) | 0.0521 (6) | |
H4A | 0.2375 | 0.5062 | 0.3204 | 0.063* | |
O1 | 0.08831 (15) | 0.42855 (14) | 0.16214 (15) | 0.0609 (5) | |
O2 | 0.34652 (14) | 0.21307 (11) | −0.15668 (12) | 0.0435 (4) | |
O3 | 0.24130 (15) | 0.08041 (11) | 0.04650 (13) | 0.0511 (5) | |
O4 | 0.10336 (13) | 0.22832 (12) | 0.16760 (12) | 0.0457 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0488 (14) | 0.0357 (13) | 0.0302 (11) | 0.0036 (11) | 0.0165 (11) | −0.0004 (10) |
C2 | 0.0390 (13) | 0.0396 (14) | 0.0232 (10) | 0.0015 (11) | 0.0072 (9) | −0.0036 (9) |
C3 | 0.0508 (15) | 0.0603 (18) | 0.0311 (12) | 0.0063 (13) | 0.0180 (11) | −0.0023 (11) |
C4 | 0.0495 (16) | 0.0614 (19) | 0.0413 (14) | 0.0121 (14) | 0.0144 (12) | −0.0139 (13) |
C5 | 0.0469 (15) | 0.0412 (15) | 0.0549 (15) | 0.0063 (12) | 0.0124 (13) | −0.0107 (12) |
C6 | 0.0378 (14) | 0.0402 (15) | 0.0454 (14) | −0.0025 (11) | 0.0108 (11) | −0.0007 (11) |
C7 | 0.0338 (12) | 0.0348 (13) | 0.0242 (10) | −0.0015 (10) | 0.0060 (9) | −0.0028 (9) |
C8 | 0.0406 (13) | 0.0360 (13) | 0.0226 (10) | −0.0039 (10) | 0.0091 (9) | 0.0006 (9) |
C9 | 0.0364 (12) | 0.0328 (12) | 0.0193 (10) | −0.0038 (10) | 0.0069 (9) | −0.0030 (9) |
C10 | 0.0319 (12) | 0.0381 (13) | 0.0229 (10) | −0.0020 (10) | 0.0068 (9) | −0.0032 (9) |
C11 | 0.0288 (11) | 0.0360 (13) | 0.0213 (10) | 0.0038 (10) | 0.0061 (9) | −0.0026 (9) |
C12 | 0.0371 (13) | 0.0382 (14) | 0.0242 (10) | 0.0036 (11) | 0.0098 (10) | −0.0052 (9) |
C13 | 0.0305 (11) | 0.0347 (13) | 0.0260 (10) | 0.0049 (10) | 0.0074 (9) | −0.0026 (9) |
C14 | 0.0425 (15) | 0.0451 (15) | 0.0397 (13) | 0.0098 (12) | 0.0160 (11) | −0.0009 (11) |
C15 | 0.0494 (16) | 0.0387 (14) | 0.0400 (13) | 0.0073 (12) | 0.0046 (11) | −0.0077 (11) |
C16 | 0.063 (2) | 0.0510 (18) | 0.0545 (17) | 0.0071 (15) | −0.0035 (15) | −0.0207 (13) |
C17 | 0.0541 (19) | 0.0541 (19) | 0.083 (2) | −0.0019 (15) | −0.0054 (16) | −0.0189 (17) |
C18 | 0.0353 (15) | 0.063 (2) | 0.095 (2) | −0.0018 (14) | 0.0114 (15) | 0.0006 (18) |
C19 | 0.0374 (14) | 0.0514 (17) | 0.0585 (16) | −0.0003 (12) | 0.0133 (12) | −0.0029 (13) |
C20 | 0.0346 (13) | 0.0354 (13) | 0.0372 (12) | 0.0033 (11) | 0.0070 (10) | 0.0001 (10) |
C21 | 0.0389 (13) | 0.0449 (15) | 0.0240 (11) | 0.0047 (11) | 0.0045 (10) | −0.0018 (10) |
C22 | 0.0685 (19) | 0.0431 (16) | 0.0476 (15) | 0.0043 (14) | 0.0055 (13) | 0.0095 (12) |
C23 | 0.0322 (13) | 0.0363 (13) | 0.0273 (11) | 0.0027 (10) | 0.0076 (10) | 0.0001 (9) |
C24 | 0.0347 (13) | 0.0396 (14) | 0.0260 (11) | 0.0013 (10) | 0.0100 (10) | 0.0009 (9) |
C25 | 0.0369 (13) | 0.0367 (13) | 0.0262 (11) | 0.0080 (10) | 0.0104 (9) | 0.0054 (9) |
C26 | 0.0372 (14) | 0.0653 (18) | 0.0364 (13) | 0.0044 (13) | 0.0112 (11) | 0.0117 (12) |
C27 | 0.0465 (16) | 0.087 (2) | 0.0538 (17) | 0.0042 (15) | 0.0263 (14) | 0.0180 (15) |
C28 | 0.0637 (18) | 0.074 (2) | 0.0369 (14) | 0.0116 (15) | 0.0283 (13) | 0.0134 (13) |
C29 | 0.0552 (16) | 0.0538 (16) | 0.0269 (11) | 0.0094 (13) | 0.0148 (11) | 0.0038 (11) |
C30 | 0.0390 (13) | 0.0385 (14) | 0.0283 (11) | 0.0065 (11) | 0.0109 (10) | 0.0022 (9) |
C31 | 0.0377 (13) | 0.0580 (16) | 0.0263 (11) | −0.0042 (12) | 0.0105 (10) | −0.0017 (10) |
N1 | 0.0426 (13) | 0.0590 (15) | 0.0451 (12) | 0.0159 (11) | 0.0126 (10) | −0.0065 (10) |
N2 | 0.0431 (11) | 0.0376 (11) | 0.0290 (9) | 0.0023 (9) | 0.0058 (8) | 0.0027 (8) |
N3 | 0.0371 (11) | 0.0631 (14) | 0.0225 (9) | −0.0068 (10) | 0.0044 (8) | −0.0026 (9) |
N4 | 0.0581 (14) | 0.0577 (14) | 0.0411 (12) | 0.0102 (11) | 0.0196 (11) | −0.0165 (10) |
O1 | 0.0446 (12) | 0.0786 (14) | 0.0649 (12) | 0.0107 (10) | 0.0269 (9) | −0.0055 (10) |
O2 | 0.0595 (11) | 0.0454 (11) | 0.0336 (8) | 0.0034 (8) | 0.0269 (8) | 0.0051 (7) |
O3 | 0.0732 (12) | 0.0463 (11) | 0.0445 (9) | 0.0007 (9) | 0.0344 (9) | 0.0102 (8) |
O4 | 0.0334 (9) | 0.0706 (12) | 0.0293 (8) | −0.0076 (9) | 0.0080 (7) | 0.0009 (8) |
C1—C9 | 1.335 (3) | C16—H16 | 0.9300 |
C1—O2 | 1.353 (3) | C17—C18 | 1.381 (5) |
C1—H1 | 0.9300 | C17—H17 | 0.9300 |
C2—O2 | 1.376 (3) | C18—C19 | 1.398 (4) |
C2—C7 | 1.382 (3) | C18—H18 | 0.9300 |
C2—C3 | 1.392 (3) | C19—C20 | 1.372 (3) |
C3—C4 | 1.362 (4) | C19—H19 | 0.9300 |
C3—H3 | 0.9300 | C21—N2 | 1.444 (3) |
C4—C5 | 1.392 (4) | C21—H21A | 0.9700 |
C4—H4 | 0.9300 | C21—H21B | 0.9700 |
C5—C6 | 1.369 (3) | C22—N2 | 1.465 (3) |
C5—H5 | 0.9300 | C22—H22A | 0.9600 |
C6—C7 | 1.403 (3) | C22—H22B | 0.9600 |
C6—H6 | 0.9300 | C22—H22C | 0.9600 |
C7—C8 | 1.460 (3) | C23—O4 | 1.222 (3) |
C8—O3 | 1.239 (3) | C23—C24 | 1.454 (3) |
C8—C9 | 1.453 (3) | C24—C31 | 1.383 (3) |
C9—C10 | 1.505 (3) | C24—C25 | 1.445 (3) |
C10—C21 | 1.521 (3) | C25—C26 | 1.385 (3) |
C10—C11 | 1.581 (3) | C25—C30 | 1.402 (3) |
C10—H10 | 0.9800 | C26—C27 | 1.383 (3) |
C11—C12 | 1.474 (3) | C26—H26 | 0.9300 |
C11—C23 | 1.570 (3) | C27—C28 | 1.390 (4) |
C11—C13 | 1.603 (3) | C27—H27 | 0.9300 |
C12—N1 | 1.138 (3) | C28—C29 | 1.367 (4) |
C13—N2 | 1.454 (3) | C28—H28 | 0.9300 |
C13—C20 | 1.497 (3) | C29—C30 | 1.386 (3) |
C13—C14 | 1.580 (3) | C29—H29 | 0.9300 |
C14—O1 | 1.214 (3) | C30—N3 | 1.377 (3) |
C14—N4 | 1.349 (3) | C31—N3 | 1.343 (3) |
C15—C16 | 1.378 (4) | C31—H31 | 0.9300 |
C15—C20 | 1.389 (3) | N3—H3A | 0.8600 |
C15—N4 | 1.393 (3) | N4—H4A | 0.8600 |
C16—C17 | 1.369 (4) | ||
C9—C1—O2 | 125.1 (2) | C17—C18—C19 | 120.3 (3) |
C9—C1—H1 | 117.5 | C17—C18—H18 | 119.9 |
O2—C1—H1 | 117.5 | C19—C18—H18 | 119.9 |
O2—C2—C7 | 121.33 (19) | C20—C19—C18 | 118.2 (3) |
O2—C2—C3 | 116.4 (2) | C20—C19—H19 | 120.9 |
C7—C2—C3 | 122.2 (2) | C18—C19—H19 | 120.9 |
C4—C3—C2 | 118.2 (2) | C19—C20—C15 | 120.1 (2) |
C4—C3—H3 | 120.9 | C19—C20—C13 | 130.6 (2) |
C2—C3—H3 | 120.9 | C15—C20—C13 | 109.3 (2) |
C3—C4—C5 | 121.3 (2) | N2—C21—C10 | 103.20 (17) |
C3—C4—H4 | 119.4 | N2—C21—H21A | 111.1 |
C5—C4—H4 | 119.4 | C10—C21—H21A | 111.1 |
C6—C5—C4 | 119.9 (2) | N2—C21—H21B | 111.1 |
C6—C5—H5 | 120.0 | C10—C21—H21B | 111.1 |
C4—C5—H5 | 120.0 | H21A—C21—H21B | 109.1 |
C5—C6—C7 | 120.4 (2) | N2—C22—H22A | 109.5 |
C5—C6—H6 | 119.8 | N2—C22—H22B | 109.5 |
C7—C6—H6 | 119.8 | H22A—C22—H22B | 109.5 |
C2—C7—C6 | 117.9 (2) | N2—C22—H22C | 109.5 |
C2—C7—C8 | 119.8 (2) | H22A—C22—H22C | 109.5 |
C6—C7—C8 | 122.3 (2) | H22B—C22—H22C | 109.5 |
O3—C8—C9 | 121.4 (2) | O4—C23—C24 | 121.2 (2) |
O3—C8—C7 | 122.7 (2) | O4—C23—C11 | 118.47 (18) |
C9—C8—C7 | 115.85 (18) | C24—C23—C11 | 120.25 (19) |
C1—C9—C8 | 119.1 (2) | C31—C24—C25 | 106.26 (18) |
C1—C9—C10 | 123.3 (2) | C31—C24—C23 | 129.4 (2) |
C8—C9—C10 | 117.54 (18) | C25—C24—C23 | 124.3 (2) |
C9—C10—C21 | 116.64 (18) | C26—C25—C30 | 118.7 (2) |
C9—C10—C11 | 113.37 (17) | C26—C25—C24 | 135.1 (2) |
C21—C10—C11 | 102.75 (16) | C30—C25—C24 | 106.2 (2) |
C9—C10—H10 | 107.9 | C27—C26—C25 | 118.5 (2) |
C21—C10—H10 | 107.9 | C27—C26—H26 | 120.7 |
C11—C10—H10 | 107.9 | C25—C26—H26 | 120.7 |
C12—C11—C23 | 109.35 (17) | C26—C27—C28 | 121.6 (3) |
C12—C11—C10 | 110.51 (16) | C26—C27—H27 | 119.2 |
C23—C11—C10 | 110.54 (17) | C28—C27—H27 | 119.2 |
C12—C11—C13 | 110.41 (18) | C29—C28—C27 | 121.2 (2) |
C23—C11—C13 | 111.63 (16) | C29—C28—H28 | 119.4 |
C10—C11—C13 | 104.32 (16) | C27—C28—H28 | 119.4 |
N1—C12—C11 | 179.7 (3) | C28—C29—C30 | 117.1 (2) |
N2—C13—C20 | 113.88 (18) | C28—C29—H29 | 121.5 |
N2—C13—C14 | 113.76 (17) | C30—C29—H29 | 121.5 |
C20—C13—C14 | 101.03 (17) | N3—C30—C29 | 129.1 (2) |
N2—C13—C11 | 102.17 (16) | N3—C30—C25 | 107.93 (19) |
C20—C13—C11 | 116.32 (17) | C29—C30—C25 | 123.0 (2) |
C14—C13—C11 | 110.14 (18) | N3—C31—C24 | 109.9 (2) |
O1—C14—N4 | 126.6 (2) | N3—C31—H31 | 125.1 |
O1—C14—C13 | 126.2 (2) | C24—C31—H31 | 125.1 |
N4—C14—C13 | 107.2 (2) | C21—N2—C13 | 107.89 (17) |
C16—C15—C20 | 122.2 (3) | C21—N2—C22 | 114.99 (19) |
C16—C15—N4 | 127.9 (2) | C13—N2—C22 | 114.23 (18) |
C20—C15—N4 | 109.9 (2) | C31—N3—C30 | 109.70 (19) |
C17—C16—C15 | 117.0 (3) | C31—N3—H3A | 125.2 |
C17—C16—H16 | 121.5 | C30—N3—H3A | 125.2 |
C15—C16—H16 | 121.5 | C14—N4—C15 | 112.2 (2) |
C16—C17—C18 | 122.1 (3) | C14—N4—H4A | 123.9 |
C16—C17—H17 | 118.9 | C15—N4—H4A | 123.9 |
C18—C17—H17 | 118.9 | C1—O2—C2 | 118.70 (17) |
O2—C2—C3—C4 | −177.9 (2) | N4—C15—C20—C19 | 174.1 (2) |
C7—C2—C3—C4 | 2.2 (3) | C16—C15—C20—C13 | 177.2 (2) |
C2—C3—C4—C5 | −0.3 (4) | N4—C15—C20—C13 | −4.1 (3) |
C3—C4—C5—C6 | −1.6 (4) | N2—C13—C20—C19 | −49.2 (3) |
C4—C5—C6—C7 | 1.6 (4) | C14—C13—C20—C19 | −171.6 (3) |
O2—C2—C7—C6 | 177.87 (19) | C11—C13—C20—C19 | 69.2 (3) |
C3—C2—C7—C6 | −2.1 (3) | N2—C13—C20—C15 | 128.8 (2) |
O2—C2—C7—C8 | −2.4 (3) | C14—C13—C20—C15 | 6.4 (2) |
C3—C2—C7—C8 | 177.6 (2) | C11—C13—C20—C15 | −112.8 (2) |
C5—C6—C7—C2 | 0.2 (3) | C9—C10—C21—N2 | −89.1 (2) |
C5—C6—C7—C8 | −179.5 (2) | C11—C10—C21—N2 | 35.6 (2) |
C2—C7—C8—O3 | −175.6 (2) | C12—C11—C23—O4 | −135.8 (2) |
C6—C7—C8—O3 | 4.1 (3) | C10—C11—C23—O4 | −13.9 (3) |
C2—C7—C8—C9 | 4.0 (3) | C13—C11—C23—O4 | 101.7 (2) |
C6—C7—C8—C9 | −176.31 (19) | C12—C11—C23—C24 | 47.7 (3) |
O2—C1—C9—C8 | 0.8 (3) | C10—C11—C23—C24 | 169.53 (19) |
O2—C1—C9—C10 | −179.79 (19) | C13—C11—C23—C24 | −74.8 (2) |
O3—C8—C9—C1 | 176.4 (2) | O4—C23—C24—C31 | 177.3 (2) |
C7—C8—C9—C1 | −3.2 (3) | C11—C23—C24—C31 | −6.3 (4) |
O3—C8—C9—C10 | −3.0 (3) | O4—C23—C24—C25 | −4.6 (4) |
C7—C8—C9—C10 | 177.35 (17) | C11—C23—C24—C25 | 171.8 (2) |
C1—C9—C10—C21 | 18.8 (3) | C31—C24—C25—C26 | −178.7 (3) |
C8—C9—C10—C21 | −161.80 (19) | C23—C24—C25—C26 | 2.8 (4) |
C1—C9—C10—C11 | −100.3 (2) | C31—C24—C25—C30 | 1.0 (3) |
C8—C9—C10—C11 | 79.1 (2) | C23—C24—C25—C30 | −177.5 (2) |
C9—C10—C11—C12 | −5.8 (3) | C30—C25—C26—C27 | −0.2 (4) |
C21—C10—C11—C12 | −132.58 (19) | C24—C25—C26—C27 | 179.5 (3) |
C9—C10—C11—C23 | −127.01 (19) | C25—C26—C27—C28 | 0.9 (4) |
C21—C10—C11—C23 | 106.2 (2) | C26—C27—C28—C29 | −0.8 (5) |
C9—C10—C11—C13 | 112.85 (19) | C27—C28—C29—C30 | 0.1 (4) |
C21—C10—C11—C13 | −13.9 (2) | C28—C29—C30—N3 | −178.7 (3) |
C23—C11—C12—N1 | −139 (100) | C28—C29—C30—C25 | 0.6 (4) |
C10—C11—C12—N1 | 99 (58) | C26—C25—C30—N3 | 178.9 (2) |
C13—C11—C12—N1 | −16 (58) | C24—C25—C30—N3 | −0.9 (3) |
C12—C11—C13—N2 | 106.58 (18) | C26—C25—C30—C29 | −0.6 (4) |
C23—C11—C13—N2 | −131.55 (17) | C24—C25—C30—C29 | 179.6 (2) |
C10—C11—C13—N2 | −12.2 (2) | C25—C24—C31—N3 | −0.7 (3) |
C12—C11—C13—C20 | −18.1 (2) | C23—C24—C31—N3 | 177.7 (2) |
C23—C11—C13—C20 | 103.8 (2) | C10—C21—N2—C13 | −47.0 (2) |
C10—C11—C13—C20 | −136.82 (18) | C10—C21—N2—C22 | −175.8 (2) |
C12—C11—C13—C14 | −132.21 (18) | C20—C13—N2—C21 | 162.61 (19) |
C23—C11—C13—C14 | −10.3 (2) | C14—C13—N2—C21 | −82.3 (2) |
C10—C11—C13—C14 | 109.05 (18) | C11—C13—N2—C21 | 36.3 (2) |
N2—C13—C14—O1 | 50.7 (3) | C20—C13—N2—C22 | −68.2 (3) |
C20—C13—C14—O1 | 173.2 (3) | C14—C13—N2—C22 | 46.9 (3) |
C11—C13—C14—O1 | −63.3 (3) | C11—C13—N2—C22 | 165.5 (2) |
N2—C13—C14—N4 | −129.2 (2) | C24—C31—N3—C30 | 0.2 (3) |
C20—C13—C14—N4 | −6.7 (2) | C29—C30—N3—C31 | 179.9 (2) |
C11—C13—C14—N4 | 116.8 (2) | C25—C30—N3—C31 | 0.5 (3) |
C20—C15—C16—C17 | 3.2 (4) | O1—C14—N4—C15 | −175.1 (3) |
N4—C15—C16—C17 | −175.2 (3) | C13—C14—N4—C15 | 4.9 (3) |
C15—C16—C17—C18 | 0.2 (5) | C16—C15—N4—C14 | 177.9 (3) |
C16—C17—C18—C19 | −2.2 (5) | C20—C15—N4—C14 | −0.7 (3) |
C17—C18—C19—C20 | 0.9 (4) | C9—C1—O2—C2 | 1.0 (3) |
C18—C19—C20—C15 | 2.3 (4) | C7—C2—O2—C1 | −0.1 (3) |
C18—C19—C20—C13 | −179.9 (2) | C3—C2—O2—C1 | 179.87 (19) |
C16—C15—C20—C19 | −4.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4i | 0.86 | 2.14 | 2.967 (3) | 161 |
N4—H4A···O3ii | 0.86 | 2.06 | 2.866 (3) | 156 |
C29—H29···O2iii | 0.93 | 2.59 | 3.267 (3) | 131 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4i | 0.86 | 2.14 | 2.967 (3) | 161 |
N4—H4A···O3ii | 0.86 | 2.06 | 2.866 (3) | 156 |
C29—H29···O2iii | 0.93 | 2.59 | 3.267 (3) | 131 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y, z+1. |
Acknowledgements
The authors thank thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.
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