organic compounds
5-Amino-6-benzoyl-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate
aDepartment of Physics, The Madura College, Madurai 625 011, India, bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
*Correspondence e-mail: plakshmannilantha@ymail.com
In the title compound C21H17N5O4·C2H6OS, the central six-membered ring derived from 1,4-dihydropyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N atom [60 (2)°] indicate that these atoms are in sp2 leading to an essentially planar imidazolidine ring. The last heterocycle, an oxindole moiety, is also nearly planar with an r.m.s. deviation of 0.0185 (1) Å. The amine NH2 group forms an intramolecular hydrogen bond with the benzoyl group, giving a S(6) motif. In the crystal, N—H⋯O hydrogen bonds lead to the formation of chains along the c-axis direction. Within the chains there are further N—H⋯O and C—H⋯O hydrogen bonds enclosing R22(14) ring motifs. The chains are linked via N—H⋯O and C—H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent molecule which acts as both an acceptor and a donor..
CCDC reference: 998123
Related literature
For a previous related work, see: Suresh et al. (2013). For of ring systems, and small rings fused to benzene, see: Cremer & Pople (1975); Allen (1981).
Experimental
Crystal data
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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.
Supporting information
CCDC reference: 998123
10.1107/S1600536814008800/bh2496sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814008800/bh2496Isup2.hkl
A mixture of benzoylacetonitrile (1.0 mmol), isatin (1.0 mmol) and 2-(nitromethylene) imidazolidine was dissolved in 10 ml of EtOH, and triethylamine (1.0 mmol) was added. The reaction mixture was refluxed for 45 min. After completion of the reaction, as evident from TLC, the precipitated solid product was filtered and dried to obtain pure pale brown solid. Yield 94%. Melting point 530 K.
Crystal data, data collection and structure
details are summarized in Table 1. H atoms were placed in calculated positions and allowed to ride on their carrier atoms with C—H = 0.93 (aromatic CH), 0.96 (methyl CH3) or 0.97 Å (methylene CH2), and N—H = 0.86 Å. Isotropic displacement parameters for H atoms were calculated as Uiso = 1.5Ueq(C) for CH3 groups and Uiso = 1.2Ueq(carrier atom) for all other H atoms.Our interest in preparing pharmacologically active pyridine-related compounds (Suresh et al., 2013) led us to the title compound, derived from a 1,4-dihydropyridine, and we have undertaken X-ray
determination of this compound in order to establish its molecular conformation.In the title compound (Fig. 1), the central pyridine ring adopts a skew-boat conformation with the puckering parameters Q = 0.127 (3) Å, θ = 87.3 (13) and ϕ = 198.3 (3)° (Cremer & Pople, 1975). The sums of bond angles around N4 and N5, 358.7 (2)° and 360 (2)° respectively, show that N atoms are in sp2 leading to an essentially planar imidazolidine ring. The C2/C8/N3/C9/C10 ring of the oxindole moiety is planar with r.m.s. deviation of 0.0185 (1) Å. The small tilt between the planes of the five and six-membered rings in the oxindole unit is 1.21 (1)°. The sum of the bond angles around N3 atom is 360 (1)° implying a noticeable flattening of the geometry about N3. The shorter bond lengths N3—C8 = 1.337 (4) Å and N3—C9 = 1.401 (4) Å indicate the electron donating effect of the N atom. The nitro group, N1/O1/O2, is twisted away from the mean plane of the six-membered ring, forming the dihedral angle of 8.90 (1)°. In the benzene ring (C9···C14) of the oxindole ring system, the expansion of the ipso angles at C9, C12 and C13 [121.9 (3), 120.8 (3) and 121.3 (3)°, respectively] and the contraction of the apical angles at C10, C11 and C14 [120.5 (3), 118.1 (3) and 117.3 (3)°, respectively] are caused by the fusion of the smaller ring to the six-membered benzene ring, and the strain is taken up by the angular distortion rather than by bond length distortions (Allen, 1981). The short contacts H2A···H7A (2.17 Å) and H2A···H7B (2.31 Å) result in the substantial widening of angle C7—N4—C4 to 124.9 (2)°.
The
features weak intra-molecular N—H···O interactions and N—H···O and C—H···O inter-molecular interactions. An inter-molecular N2—H2A···O3 interaction forms a chain along the c axis, while inter-molecular N5—H5···O3 and C6—H6B···O2 interactions form ring motifs R22(14). The solvent molecule, dimetyl sulfoxide, also takes part in the N—H···O and in the C—H···O inter-molecular interactions (Fig. 2).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).Fig. 1. The molecular structure of the title compound, showing 20% probability displacement ellipsoids. All H atoms are omitted for clarity. | |
Fig. 2. Partial packing diagram of the title compound. Dashed bonds represent inter-molecular hydrogen bonds. |
C21H17N5O4·C2H6OS | F(000) = 1008 |
Mr = 481.52 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Melting point: 530 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.476 (3) Å | Cell parameters from 2000 reflections |
b = 13.527 (2) Å | θ = 2–31° |
c = 10.0727 (18) Å | µ = 0.19 mm−1 |
β = 99.868 (5)° | T = 293 K |
V = 2211.7 (7) Å3 | Block, brown |
Z = 4 | 0.21 × 0.19 × 0.18 mm |
Bruker Kappa APEXII diffractometer | 4109 independent reflections |
Radiation source: fine-focus sealed tube | 2818 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 0 pixels mm-1 | θmax = 25.5°, θmin = 2.5° |
ω and ϕ scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | k = −16→16 |
Tmin = 0.967, Tmax = 0.974 | l = −12→12 |
31940 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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0634P)2 + 2.4142P] where P = (Fo2 + 2Fc2)/3 |
4109 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
0 constraints |
C21H17N5O4·C2H6OS | V = 2211.7 (7) Å3 |
Mr = 481.52 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.476 (3) Å | µ = 0.19 mm−1 |
b = 13.527 (2) Å | T = 293 K |
c = 10.0727 (18) Å | 0.21 × 0.19 × 0.18 mm |
β = 99.868 (5)° |
Bruker Kappa APEXII diffractometer | 4109 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2818 reflections with I > 2σ(I) |
Tmin = 0.967, Tmax = 0.974 | Rint = 0.070 |
31940 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.92 e Å−3 |
4109 reflections | Δρmin = −0.47 e Å−3 |
307 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.12735 (16) | 0.47401 (19) | 0.4943 (3) | 0.0273 (6) | |
C2 | 0.19857 (15) | 0.4409 (2) | 0.6005 (3) | 0.0268 (6) | |
C3 | 0.20085 (16) | 0.3272 (2) | 0.6119 (3) | 0.0285 (6) | |
C4 | 0.14829 (16) | 0.2694 (2) | 0.5220 (3) | 0.0292 (6) | |
C5 | 0.08157 (16) | 0.4092 (2) | 0.4049 (3) | 0.0292 (6) | |
C6 | −0.01200 (18) | 0.3357 (2) | 0.2370 (3) | 0.0429 (8) | |
H6A | −0.0032 | 0.3343 | 0.1442 | 0.051* | |
H6B | −0.0705 | 0.3291 | 0.2384 | 0.051* | |
C7 | 0.03642 (18) | 0.2551 (2) | 0.3186 (3) | 0.0432 (8) | |
H7A | 0.0010 | 0.2147 | 0.3641 | 0.052* | |
H7B | 0.0641 | 0.2132 | 0.2622 | 0.052* | |
C8 | 0.18947 (16) | 0.4842 (2) | 0.7405 (3) | 0.0293 (6) | |
C9 | 0.30975 (16) | 0.5444 (2) | 0.6929 (3) | 0.0330 (7) | |
C10 | 0.27937 (15) | 0.4874 (2) | 0.5812 (3) | 0.0295 (6) | |
C11 | 0.32187 (17) | 0.4803 (2) | 0.4754 (3) | 0.0371 (7) | |
H11 | 0.3022 | 0.4414 | 0.4006 | 0.045* | |
C12 | 0.39483 (19) | 0.5327 (2) | 0.4833 (4) | 0.0473 (8) | |
H12 | 0.4244 | 0.5293 | 0.4127 | 0.057* | |
C13 | 0.42409 (19) | 0.5898 (3) | 0.5948 (4) | 0.0494 (9) | |
H13 | 0.4731 | 0.6246 | 0.5978 | 0.059* | |
C14 | 0.38202 (18) | 0.5964 (2) | 0.7022 (4) | 0.0434 (8) | |
H14 | 0.4019 | 0.6346 | 0.7775 | 0.052* | |
C15 | 0.2595 (3) | 0.6930 (3) | 0.2703 (4) | 0.0615 (10) | |
H15A | 0.3158 | 0.6979 | 0.3147 | 0.092* | |
H15B | 0.2246 | 0.6827 | 0.3362 | 0.092* | |
H15C | 0.2439 | 0.7531 | 0.2218 | 0.092* | |
C16 | 0.1423 (2) | 0.6058 (3) | 0.0959 (4) | 0.0730 (12) | |
H16A | 0.1245 | 0.5554 | 0.0302 | 0.109* | |
H16B | 0.1319 | 0.6697 | 0.0550 | 0.109* | |
H16C | 0.1126 | 0.5995 | 0.1695 | 0.109* | |
C31 | 0.25828 (18) | 0.2769 (2) | 0.7134 (3) | 0.0362 (7) | |
C32 | 0.33727 (18) | 0.3217 (2) | 0.7853 (3) | 0.0363 (7) | |
C33 | 0.4043 (2) | 0.3233 (3) | 0.7190 (4) | 0.0495 (9) | |
H33 | 0.3980 | 0.3065 | 0.6283 | 0.059* | |
C34 | 0.4805 (2) | 0.3501 (3) | 0.7889 (5) | 0.0672 (12) | |
H34 | 0.5259 | 0.3500 | 0.7453 | 0.081* | |
C35 | 0.4901 (3) | 0.3769 (3) | 0.9213 (5) | 0.0768 (14) | |
H35 | 0.5418 | 0.3951 | 0.9672 | 0.092* | |
C36 | 0.4236 (3) | 0.3768 (3) | 0.9867 (4) | 0.0719 (13) | |
H36 | 0.4299 | 0.3968 | 1.0763 | 0.086* | |
C37 | 0.3472 (2) | 0.3471 (3) | 0.9197 (3) | 0.0519 (9) | |
H37 | 0.3027 | 0.3443 | 0.9651 | 0.062* | |
N1 | 0.10891 (14) | 0.57350 (18) | 0.4841 (2) | 0.0330 (6) | |
N2 | 0.14345 (15) | 0.17067 (18) | 0.5281 (3) | 0.0398 (6) | |
H2A | 0.1097 | 0.1391 | 0.4684 | 0.048* | |
H2B | 0.1741 | 0.1389 | 0.5917 | 0.048* | |
N3 | 0.25616 (14) | 0.53850 (17) | 0.7866 (2) | 0.0342 (6) | |
H3 | 0.2651 | 0.5665 | 0.8644 | 0.041* | |
N4 | 0.09609 (13) | 0.31051 (18) | 0.4158 (2) | 0.0326 (6) | |
N5 | 0.02048 (14) | 0.42620 (19) | 0.3037 (2) | 0.0374 (6) | |
H5 | 0.0021 | 0.4842 | 0.2801 | 0.045* | |
O1 | 0.05174 (13) | 0.60506 (16) | 0.3938 (2) | 0.0445 (6) | |
O2 | 0.14848 (13) | 0.63220 (15) | 0.5658 (2) | 0.0431 (6) | |
O3 | 0.13161 (12) | 0.46735 (14) | 0.80020 (19) | 0.0352 (5) | |
O4 | 0.24819 (17) | 0.18945 (18) | 0.7443 (3) | 0.0682 (8) | |
O5 | 0.28997 (18) | 0.6227 (3) | 0.0417 (3) | 0.0927 (12) | |
S1 | 0.24911 (7) | 0.59246 (8) | 0.15647 (10) | 0.0650 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0223 (13) | 0.0279 (15) | 0.0298 (14) | 0.0015 (11) | −0.0003 (11) | 0.0011 (12) |
C2 | 0.0203 (13) | 0.0296 (14) | 0.0287 (14) | −0.0009 (11) | −0.0009 (11) | −0.0003 (12) |
C3 | 0.0221 (13) | 0.0311 (15) | 0.0312 (15) | −0.0011 (11) | 0.0015 (11) | −0.0002 (12) |
C4 | 0.0213 (13) | 0.0322 (16) | 0.0343 (15) | −0.0013 (11) | 0.0048 (11) | −0.0007 (12) |
C5 | 0.0209 (13) | 0.0380 (17) | 0.0283 (14) | 0.0006 (11) | 0.0034 (11) | 0.0006 (12) |
C6 | 0.0273 (16) | 0.057 (2) | 0.0399 (17) | 0.0011 (14) | −0.0074 (13) | −0.0116 (15) |
C7 | 0.0305 (16) | 0.0461 (19) | 0.0474 (19) | −0.0066 (14) | −0.0093 (14) | −0.0115 (15) |
C8 | 0.0247 (14) | 0.0260 (14) | 0.0352 (15) | 0.0037 (11) | −0.0007 (12) | 0.0025 (12) |
C9 | 0.0234 (14) | 0.0331 (16) | 0.0404 (16) | 0.0002 (12) | −0.0006 (12) | −0.0012 (13) |
C10 | 0.0192 (13) | 0.0307 (15) | 0.0366 (15) | 0.0018 (11) | −0.0009 (11) | 0.0020 (12) |
C11 | 0.0277 (15) | 0.0436 (18) | 0.0385 (17) | 0.0032 (13) | 0.0015 (12) | 0.0028 (14) |
C12 | 0.0321 (17) | 0.054 (2) | 0.058 (2) | −0.0006 (15) | 0.0134 (15) | 0.0095 (17) |
C13 | 0.0248 (16) | 0.050 (2) | 0.073 (2) | −0.0077 (14) | 0.0066 (16) | 0.0033 (18) |
C14 | 0.0257 (15) | 0.0425 (19) | 0.058 (2) | −0.0073 (13) | −0.0031 (14) | −0.0093 (16) |
C15 | 0.074 (3) | 0.059 (2) | 0.049 (2) | 0.005 (2) | 0.0023 (19) | −0.0067 (18) |
C16 | 0.059 (3) | 0.089 (3) | 0.071 (3) | −0.006 (2) | 0.012 (2) | −0.018 (2) |
C31 | 0.0331 (16) | 0.0346 (17) | 0.0383 (17) | 0.0008 (13) | −0.0012 (13) | 0.0013 (13) |
C32 | 0.0307 (16) | 0.0320 (16) | 0.0423 (17) | 0.0042 (12) | −0.0049 (13) | 0.0066 (13) |
C33 | 0.0407 (19) | 0.050 (2) | 0.058 (2) | 0.0070 (15) | 0.0094 (16) | 0.0066 (17) |
C34 | 0.0297 (19) | 0.068 (3) | 0.103 (4) | 0.0031 (18) | 0.007 (2) | 0.021 (2) |
C35 | 0.042 (2) | 0.081 (3) | 0.095 (3) | −0.020 (2) | −0.024 (2) | 0.028 (3) |
C36 | 0.073 (3) | 0.081 (3) | 0.050 (2) | −0.023 (2) | −0.021 (2) | 0.009 (2) |
C37 | 0.047 (2) | 0.064 (2) | 0.0402 (19) | −0.0104 (17) | −0.0042 (15) | 0.0026 (17) |
N1 | 0.0254 (12) | 0.0367 (14) | 0.0352 (13) | 0.0021 (10) | 0.0006 (10) | 0.0050 (11) |
N2 | 0.0381 (14) | 0.0295 (14) | 0.0482 (15) | −0.0054 (11) | −0.0028 (12) | −0.0016 (11) |
N3 | 0.0299 (13) | 0.0379 (14) | 0.0322 (13) | −0.0008 (10) | −0.0019 (10) | −0.0067 (11) |
N4 | 0.0218 (12) | 0.0362 (14) | 0.0364 (13) | 0.0002 (10) | −0.0045 (10) | −0.0058 (11) |
N5 | 0.0274 (13) | 0.0447 (15) | 0.0355 (13) | 0.0032 (11) | −0.0080 (10) | −0.0004 (12) |
O1 | 0.0371 (12) | 0.0430 (13) | 0.0466 (13) | 0.0088 (10) | −0.0117 (10) | 0.0091 (10) |
O2 | 0.0402 (12) | 0.0334 (12) | 0.0500 (13) | −0.0012 (9) | −0.0083 (10) | −0.0052 (10) |
O3 | 0.0287 (11) | 0.0408 (12) | 0.0360 (11) | 0.0024 (9) | 0.0054 (9) | 0.0033 (9) |
O4 | 0.0734 (18) | 0.0428 (15) | 0.0733 (18) | −0.0118 (13) | −0.0298 (14) | 0.0201 (13) |
O5 | 0.0581 (18) | 0.163 (3) | 0.0610 (17) | −0.0245 (19) | 0.0210 (14) | −0.053 (2) |
S1 | 0.0735 (7) | 0.0610 (7) | 0.0544 (6) | 0.0189 (5) | −0.0064 (5) | −0.0117 (5) |
C1—N1 | 1.380 (4) | C13—H13 | 0.9300 |
C1—C5 | 1.384 (4) | C14—H14 | 0.9300 |
C1—C2 | 1.514 (3) | C15—S1 | 1.769 (4) |
C2—C10 | 1.515 (4) | C15—H15A | 0.9600 |
C2—C3 | 1.542 (4) | C15—H15B | 0.9600 |
C2—C8 | 1.558 (4) | C15—H15C | 0.9600 |
C3—C4 | 1.383 (4) | C16—S1 | 1.771 (4) |
C3—C31 | 1.439 (4) | C16—H16A | 0.9600 |
C4—N2 | 1.340 (4) | C16—H16B | 0.9600 |
C4—N4 | 1.370 (3) | C16—H16C | 0.9600 |
C5—N5 | 1.324 (3) | C31—O4 | 1.242 (4) |
C5—N4 | 1.357 (4) | C31—C32 | 1.504 (4) |
C6—N5 | 1.454 (4) | C32—C37 | 1.380 (5) |
C6—C7 | 1.509 (4) | C32—C33 | 1.385 (4) |
C6—H6A | 0.9700 | C33—C34 | 1.379 (5) |
C6—H6B | 0.9700 | C33—H33 | 0.9300 |
C7—N4 | 1.468 (3) | C34—C35 | 1.364 (6) |
C7—H7A | 0.9700 | C34—H34 | 0.9300 |
C7—H7B | 0.9700 | C35—C36 | 1.372 (6) |
C8—O3 | 1.232 (3) | C35—H35 | 0.9300 |
C8—N3 | 1.337 (4) | C36—C37 | 1.382 (5) |
C9—C14 | 1.373 (4) | C36—H36 | 0.9300 |
C9—C10 | 1.385 (4) | C37—H37 | 0.9300 |
C9—N3 | 1.401 (4) | N1—O2 | 1.245 (3) |
C10—C11 | 1.375 (4) | N1—O1 | 1.266 (3) |
C11—C12 | 1.386 (4) | N2—H2A | 0.8600 |
C11—H11 | 0.9300 | N2—H2B | 0.8600 |
C12—C13 | 1.380 (5) | N3—H3 | 0.8600 |
C12—H12 | 0.9300 | N5—H5 | 0.8600 |
C13—C14 | 1.384 (5) | O5—S1 | 1.491 (3) |
N1—C1—C5 | 118.8 (2) | S1—C15—H15A | 109.5 |
N1—C1—C2 | 118.4 (2) | S1—C15—H15B | 109.5 |
C5—C1—C2 | 122.8 (2) | H15A—C15—H15B | 109.5 |
C1—C2—C10 | 112.2 (2) | S1—C15—H15C | 109.5 |
C1—C2—C3 | 110.7 (2) | H15A—C15—H15C | 109.5 |
C10—C2—C3 | 114.4 (2) | H15B—C15—H15C | 109.5 |
C1—C2—C8 | 110.2 (2) | S1—C16—H16A | 109.5 |
C10—C2—C8 | 100.5 (2) | S1—C16—H16B | 109.5 |
C3—C2—C8 | 108.2 (2) | H16A—C16—H16B | 109.5 |
C4—C3—C31 | 117.4 (3) | S1—C16—H16C | 109.5 |
C4—C3—C2 | 120.7 (2) | H16A—C16—H16C | 109.5 |
C31—C3—C2 | 121.9 (2) | H16B—C16—H16C | 109.5 |
N2—C4—N4 | 114.0 (2) | O4—C31—C3 | 121.9 (3) |
N2—C4—C3 | 124.7 (3) | O4—C31—C32 | 113.9 (3) |
N4—C4—C3 | 121.4 (2) | C3—C31—C32 | 124.1 (3) |
N5—C5—N4 | 109.5 (2) | C37—C32—C33 | 119.9 (3) |
N5—C5—C1 | 130.4 (3) | C37—C32—C31 | 121.4 (3) |
N4—C5—C1 | 120.1 (2) | C33—C32—C31 | 118.1 (3) |
N5—C6—C7 | 103.8 (2) | C34—C33—C32 | 119.3 (4) |
N5—C6—H6A | 111.0 | C34—C33—H33 | 120.3 |
C7—C6—H6A | 111.0 | C32—C33—H33 | 120.3 |
N5—C6—H6B | 111.0 | C35—C34—C33 | 120.8 (4) |
C7—C6—H6B | 111.0 | C35—C34—H34 | 119.6 |
H6A—C6—H6B | 109.0 | C33—C34—H34 | 119.6 |
N4—C7—C6 | 103.1 (2) | C34—C35—C36 | 120.1 (4) |
N4—C7—H7A | 111.2 | C34—C35—H35 | 120.0 |
C6—C7—H7A | 111.2 | C36—C35—H35 | 120.0 |
N4—C7—H7B | 111.2 | C35—C36—C37 | 120.1 (4) |
C6—C7—H7B | 111.2 | C35—C36—H36 | 120.0 |
H7A—C7—H7B | 109.1 | C37—C36—H36 | 120.0 |
O3—C8—N3 | 126.2 (3) | C32—C37—C36 | 119.8 (4) |
O3—C8—C2 | 125.1 (2) | C32—C37—H37 | 120.1 |
N3—C8—C2 | 108.7 (2) | C36—C37—H37 | 120.1 |
C14—C9—C10 | 121.9 (3) | O2—N1—O1 | 120.1 (2) |
C14—C9—N3 | 128.6 (3) | O2—N1—C1 | 119.3 (2) |
C10—C9—N3 | 109.5 (2) | O1—N1—C1 | 120.6 (2) |
C11—C10—C9 | 120.5 (3) | C4—N2—H2A | 120.0 |
C11—C10—C2 | 130.2 (3) | C4—N2—H2B | 120.0 |
C9—C10—C2 | 109.3 (2) | H2A—N2—H2B | 120.0 |
C10—C11—C12 | 118.1 (3) | C8—N3—C9 | 111.9 (2) |
C10—C11—H11 | 120.9 | C8—N3—H3 | 124.1 |
C12—C11—H11 | 120.9 | C9—N3—H3 | 124.1 |
C13—C12—C11 | 120.8 (3) | C5—N4—C4 | 122.7 (2) |
C13—C12—H12 | 119.6 | C5—N4—C7 | 111.1 (2) |
C11—C12—H12 | 119.6 | C4—N4—C7 | 124.9 (2) |
C12—C13—C14 | 121.3 (3) | C5—N5—C6 | 112.4 (2) |
C12—C13—H13 | 119.3 | C5—N5—H5 | 123.8 |
C14—C13—H13 | 119.3 | C6—N5—H5 | 123.8 |
C9—C14—C13 | 117.3 (3) | O5—S1—C15 | 106.5 (2) |
C9—C14—H14 | 121.3 | O5—S1—C16 | 105.0 (2) |
C13—C14—H14 | 121.3 | C15—S1—C16 | 97.2 (2) |
N1—C1—C2—C10 | −60.0 (3) | C10—C9—C14—C13 | −0.1 (5) |
C5—C1—C2—C10 | 118.2 (3) | N3—C9—C14—C13 | 179.9 (3) |
N1—C1—C2—C3 | 170.8 (2) | C12—C13—C14—C9 | −0.4 (5) |
C5—C1—C2—C3 | −10.9 (4) | C4—C3—C31—O4 | −18.9 (5) |
N1—C1—C2—C8 | 51.1 (3) | C2—C3—C31—O4 | 162.4 (3) |
C5—C1—C2—C8 | −130.6 (3) | C4—C3—C31—C32 | 157.3 (3) |
C1—C2—C3—C4 | 6.8 (4) | C2—C3—C31—C32 | −21.4 (4) |
C10—C2—C3—C4 | −121.2 (3) | O4—C31—C32—C37 | −73.6 (4) |
C8—C2—C3—C4 | 127.7 (3) | C3—C31—C32—C37 | 109.9 (4) |
C1—C2—C3—C31 | −174.6 (2) | O4—C31—C32—C33 | 96.9 (4) |
C10—C2—C3—C31 | 57.4 (3) | C3—C31—C32—C33 | −79.6 (4) |
C8—C2—C3—C31 | −53.7 (3) | C37—C32—C33—C34 | 0.2 (5) |
C31—C3—C4—N2 | 4.5 (4) | C31—C32—C33—C34 | −170.4 (3) |
C2—C3—C4—N2 | −176.8 (3) | C32—C33—C34—C35 | −1.3 (6) |
C31—C3—C4—N4 | −174.9 (3) | C33—C34—C35—C36 | 0.3 (6) |
C2—C3—C4—N4 | 3.8 (4) | C34—C35—C36—C37 | 1.8 (7) |
N1—C1—C5—N5 | 1.4 (5) | C33—C32—C37—C36 | 1.9 (5) |
C2—C1—C5—N5 | −176.8 (3) | C31—C32—C37—C36 | 172.2 (3) |
N1—C1—C5—N4 | −177.4 (2) | C35—C36—C37—C32 | −2.8 (6) |
C2—C1—C5—N4 | 4.4 (4) | C5—C1—N1—O2 | 178.4 (2) |
N5—C6—C7—N4 | −4.7 (3) | C2—C1—N1—O2 | −3.3 (4) |
C1—C2—C8—O3 | 61.2 (3) | C5—C1—N1—O1 | −0.7 (4) |
C10—C2—C8—O3 | 179.8 (3) | C2—C1—N1—O1 | 177.6 (2) |
C3—C2—C8—O3 | −60.0 (3) | O3—C8—N3—C9 | −179.0 (3) |
C1—C2—C8—N3 | −121.4 (2) | C2—C8—N3—C9 | 3.6 (3) |
C10—C2—C8—N3 | −2.8 (3) | C14—C9—N3—C8 | 177.1 (3) |
C3—C2—C8—N3 | 117.4 (2) | C10—C9—N3—C8 | −2.9 (3) |
C14—C9—C10—C11 | 0.8 (4) | N5—C5—N4—C4 | −171.2 (2) |
N3—C9—C10—C11 | −179.2 (2) | C1—C5—N4—C4 | 7.8 (4) |
C14—C9—C10—C2 | −179.2 (3) | N5—C5—N4—C7 | −3.7 (3) |
N3—C9—C10—C2 | 0.9 (3) | C1—C5—N4—C7 | 175.3 (3) |
C1—C2—C10—C11 | −61.7 (4) | N2—C4—N4—C5 | 168.5 (3) |
C3—C2—C10—C11 | 65.5 (4) | C3—C4—N4—C5 | −12.0 (4) |
C8—C2—C10—C11 | −178.8 (3) | N2—C4—N4—C7 | 2.8 (4) |
C1—C2—C10—C9 | 118.2 (3) | C3—C4—N4—C7 | −177.8 (3) |
C3—C2—C10—C9 | −114.6 (3) | C6—C7—N4—C5 | 5.3 (3) |
C8—C2—C10—C9 | 1.1 (3) | C6—C7—N4—C4 | 172.5 (3) |
C9—C10—C11—C12 | −0.9 (4) | N4—C5—N5—C6 | 0.3 (3) |
C2—C10—C11—C12 | 179.0 (3) | C1—C5—N5—C6 | −178.6 (3) |
C10—C11—C12—C13 | 0.4 (5) | C7—C6—N5—C5 | 3.0 (3) |
C11—C12—C13—C14 | 0.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O4 | 0.86 | 1.92 | 2.549 (3) | 129 |
N2—H2A···O3i | 0.86 | 2.30 | 2.939 (3) | 131 |
N3—H3···O5ii | 0.86 | 1.92 | 2.779 (4) | 177 |
N5—H5···O1 | 0.86 | 2.08 | 2.604 (3) | 119 |
N5—H5···O3iii | 0.86 | 2.31 | 2.924 (3) | 129 |
C6—H6B···O2iii | 0.97 | 2.59 | 3.274 (4) | 128 |
C11—H11···O4i | 0.93 | 2.43 | 3.346 (4) | 167 |
C15—H15C···O2iv | 0.96 | 2.55 | 3.448 (4) | 156 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y, z+1; (iii) −x, −y+1, −z+1; (iv) x, −y+3/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O4 | 0.86 | 1.92 | 2.549 (3) | 129.1 |
N2—H2A···O3i | 0.86 | 2.30 | 2.939 (3) | 131.4 |
N3—H3···O5ii | 0.86 | 1.92 | 2.779 (4) | 176.5 |
N5—H5···O3iii | 0.86 | 2.31 | 2.924 (3) | 128.7 |
C6—H6B···O2iii | 0.97 | 2.59 | 3.274 (4) | 128.2 |
C11—H11···O4i | 0.93 | 2.43 | 3.346 (4) | 166.7 |
C15—H15C···O2iv | 0.96 | 2.55 | 3.448 (4) | 155.8 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y, z+1; (iii) −x, −y+1, −z+1; (iv) x, −y+3/2, z−1/2. |
Acknowledgements
JS and RAN thank the management of the Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009).
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