organic compounds
{2-[(1H-Indol-3-ylmethylidene)amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}(phenyl)methanone
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cMaterials Science Center, University of Mysore, Vijyana Bhavan Building, Manasagangothri, Mysore 570 006, India
*Correspondence e-mail: jjasinski@keene.edu
The title compound, C24H20N2OS, crystallizes with two independent molecules (A and B) in the in each of which the cyclohexene rings adopt half-chair conformations. The mean plane of the indole ring is twisted from those of the phenyl and thiophene rings by 69.0 (7) and 8.3 (5)°, respectively, in molecule A and by 65.4 (9) and 6.7 (5)°, respectively, in molecule B. The dihedral angles between the mean planes of the phenyl and thiophene rings are 63.0 (4) and 58.8 (9)° in molecules A and B, respectively. In the crystal, N—H⋯O hydrogen bonds lead to the formation of an infinite chain along [101]. In addition, π–π stacking interactions are observed involving the thiophene and pyrrole rings of the two molecules, with a shortest intercentroid distance of 3.468 (2) Å.
CCDC reference: 993031
Related literature
For applications of 2-aminothiophene derivatives, see: Sabnis et al. (1999); Puterová et al. (2010); Cannito et al. (1990); Nikolakopoulos et al. (2006); Lütjens et al. (2005). For the biological and industrial importance of see: Desai et al. (2001); Karia & Parsania (1999); Samadhiya & Halve (2001); Singh & Dash (1988); Aydogan et al. (2001); Taggi et al. (2002). For a related structure, see: Kubicki et al. (2012). For puckering parameters, see Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 993031
10.1107/S1600536814006345/bt6971sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006345/bt6971Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814006345/bt6971Isup3.cml
To a solution of (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)phenyl methanone (200 mg, 0.79 mmol) in 10 ml of methanol an equimolar amount of 1H-Indole-3-carbaldehyde (115 mg, 0.79 mmol) was added with constant stirring. The mixture was refluxed for 6 hours. An orange colored precipitate was obtained. The reaction completion was confirmed by thin layer
The precipitate was filtered and dried at room temperature overnight. The solid was recrystallized using methanol and the crystals were used as such for X-ray diffraction studies.All of the H atoms were placed in their calculated positions and then refined using the riding model with atom—H lengths of 0.93Å (CH); 0.97Å (CH2) or 0.86Å (NH). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2, NH) times Ueq of the parent atom.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C24H20N2OS | F(000) = 808 |
Mr = 384.48 | Dx = 1.364 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 8.66858 (16) Å | Cell parameters from 6047 reflections |
b = 21.8200 (4) Å | θ = 4.1–71.4° |
c = 10.41956 (18) Å | µ = 1.66 mm−1 |
β = 108.1709 (19)° | T = 173 K |
V = 1872.55 (6) Å3 | Block, orange |
Z = 4 | 0.22 × 0.18 × 0.06 mm |
Agilent Eos Gemini diffractometer | 6843 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 6396 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.039 |
ω scans | θmax = 71.4°, θmin = 4.1° |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | h = −10→10 |
Tmin = 0.865, Tmax = 1.000 | k = −26→24 |
11535 measured reflections | l = −10→12 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0599P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.098 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 0.42 e Å−3 |
6843 reflections | Δρmin = −0.26 e Å−3 |
505 parameters | Absolute structure: Flack parameter determined using 2790 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.171 (10) |
Primary atom site location: structure-invariant direct methods |
C24H20N2OS | V = 1872.55 (6) Å3 |
Mr = 384.48 | Z = 4 |
Monoclinic, P21 | Cu Kα radiation |
a = 8.66858 (16) Å | µ = 1.66 mm−1 |
b = 21.8200 (4) Å | T = 173 K |
c = 10.41956 (18) Å | 0.22 × 0.18 × 0.06 mm |
β = 108.1709 (19)° |
Agilent Eos Gemini diffractometer | 6843 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 6396 reflections with I > 2σ(I) |
Tmin = 0.865, Tmax = 1.000 | Rint = 0.039 |
11535 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.098 | Δρmax = 0.42 e Å−3 |
S = 1.01 | Δρmin = −0.26 e Å−3 |
6843 reflections | Absolute structure: Flack parameter determined using 2790 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
505 parameters | Absolute structure parameter: 0.171 (10) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.47092 (9) | 0.61450 (3) | 1.00227 (7) | 0.02402 (17) | |
O1A | 0.3541 (3) | 0.75120 (12) | 0.6132 (2) | 0.0308 (5) | |
N1A | 0.6290 (3) | 0.72540 (12) | 1.0124 (3) | 0.0214 (5) | |
N2A | 1.0929 (3) | 0.76763 (15) | 1.3669 (3) | 0.0294 (6) | |
H2A | 1.1732 | 0.7651 | 1.4402 | 0.035* | |
C1A | 0.3945 (4) | 0.75388 (16) | 0.7365 (3) | 0.0220 (6) | |
C2A | 0.3944 (4) | 0.69809 (14) | 0.8176 (3) | 0.0209 (6) | |
C3A | 0.2860 (4) | 0.64697 (14) | 0.7671 (3) | 0.0232 (6) | |
C4A | 0.1599 (4) | 0.64209 (16) | 0.6297 (3) | 0.0304 (7) | |
H4AA | 0.2062 | 0.6558 | 0.5611 | 0.037* | |
H4AB | 0.0686 | 0.6685 | 0.6263 | 0.037* | |
C5A | 0.1007 (4) | 0.57594 (17) | 0.6006 (4) | 0.0326 (8) | |
H5AA | 0.0047 | 0.5752 | 0.5218 | 0.039* | |
H5AB | 0.1841 | 0.5518 | 0.5803 | 0.039* | |
C6A | 0.0609 (5) | 0.54746 (18) | 0.7194 (4) | 0.0360 (8) | |
H6AA | 0.0138 | 0.5072 | 0.6944 | 0.043* | |
H6AB | −0.0183 | 0.5727 | 0.7432 | 0.043* | |
C7A | 0.2142 (4) | 0.54194 (16) | 0.8409 (4) | 0.0302 (7) | |
H7AA | 0.1847 | 0.5341 | 0.9219 | 0.036* | |
H7AB | 0.2794 | 0.5079 | 0.8277 | 0.036* | |
C8A | 0.3107 (4) | 0.60052 (15) | 0.8572 (3) | 0.0249 (6) | |
C9A | 0.5045 (4) | 0.68713 (14) | 0.9440 (3) | 0.0207 (6) | |
C10A | 0.4374 (4) | 0.81499 (15) | 0.8025 (3) | 0.0225 (6) | |
C11A | 0.5143 (4) | 0.85813 (17) | 0.7429 (4) | 0.0319 (7) | |
H11A | 0.5438 | 0.8475 | 0.6673 | 0.038* | |
C12A | 0.5459 (5) | 0.91625 (18) | 0.7967 (4) | 0.0409 (9) | |
H12A | 0.6015 | 0.9441 | 0.7599 | 0.049* | |
C13A | 0.4957 (5) | 0.93340 (17) | 0.9049 (4) | 0.0442 (10) | |
H13A | 0.5137 | 0.9732 | 0.9384 | 0.053* | |
C14A | 0.4184 (5) | 0.89116 (19) | 0.9637 (4) | 0.0393 (9) | |
H14A | 0.3846 | 0.9026 | 1.0366 | 0.047* | |
C15A | 0.3916 (4) | 0.83197 (16) | 0.9137 (3) | 0.0291 (7) | |
H15A | 0.3427 | 0.8035 | 0.9549 | 0.035* | |
C16A | 0.7273 (4) | 0.70843 (15) | 1.1267 (3) | 0.0213 (6) | |
H16A | 0.7091 | 0.6710 | 1.1621 | 0.026* | |
C17A | 0.8636 (4) | 0.74433 (15) | 1.2023 (3) | 0.0227 (6) | |
C18A | 0.9206 (4) | 0.80258 (15) | 1.1706 (3) | 0.0226 (6) | |
C19A | 0.8656 (4) | 0.84400 (16) | 1.0639 (3) | 0.0289 (7) | |
H19A | 0.7702 | 0.8366 | 0.9940 | 0.035* | |
C20A | 0.9562 (5) | 0.89634 (18) | 1.0644 (4) | 0.0373 (8) | |
H20A | 0.9212 | 0.9241 | 0.9935 | 0.045* | |
C21A | 1.0994 (5) | 0.90821 (18) | 1.1692 (4) | 0.0378 (8) | |
H21A | 1.1577 | 0.9438 | 1.1670 | 0.045* | |
C22A | 1.1558 (4) | 0.86806 (19) | 1.2761 (4) | 0.0344 (8) | |
H22A | 1.2510 | 0.8759 | 1.3459 | 0.041* | |
C23A | 1.0650 (4) | 0.81545 (17) | 1.2756 (3) | 0.0268 (7) | |
C24A | 0.9739 (4) | 0.72543 (17) | 1.3226 (3) | 0.0258 (7) | |
H24A | 0.9673 | 0.6890 | 1.3668 | 0.031* | |
S1B | 0.58516 (9) | 0.82206 (3) | 0.31301 (7) | 0.02433 (17) | |
O1B | 0.7245 (3) | 0.70323 (12) | 0.7261 (2) | 0.0310 (5) | |
N1B | 0.4361 (3) | 0.71109 (13) | 0.3214 (3) | 0.0221 (5) | |
N2B | −0.0273 (3) | 0.66696 (14) | −0.0369 (3) | 0.0255 (6) | |
H2B | −0.1076 | 0.6698 | −0.1102 | 0.031* | |
C1B | 0.6804 (4) | 0.69303 (15) | 0.6038 (3) | 0.0224 (6) | |
C2B | 0.6739 (4) | 0.74464 (15) | 0.5103 (3) | 0.0222 (6) | |
C3B | 0.7811 (4) | 0.79705 (15) | 0.5483 (3) | 0.0244 (6) | |
C4B | 0.9186 (4) | 0.80540 (16) | 0.6792 (4) | 0.0328 (8) | |
H4BA | 1.0085 | 0.7790 | 0.6788 | 0.039* | |
H4BB | 0.8821 | 0.7934 | 0.7545 | 0.039* | |
C5B | 0.9759 (5) | 0.87144 (17) | 0.6973 (4) | 0.0330 (8) | |
H5BA | 1.0771 | 0.8738 | 0.7709 | 0.040* | |
H5BB | 0.8962 | 0.8961 | 0.7216 | 0.040* | |
C6B | 1.0013 (5) | 0.89755 (18) | 0.5699 (4) | 0.0365 (8) | |
H6BA | 1.0791 | 0.8724 | 0.5441 | 0.044* | |
H6BB | 1.0454 | 0.9386 | 0.5880 | 0.044* | |
C7B | 0.8411 (5) | 0.89950 (17) | 0.4535 (4) | 0.0315 (8) | |
H7BA | 0.7765 | 0.9341 | 0.4651 | 0.038* | |
H7BB | 0.8632 | 0.9045 | 0.3683 | 0.038* | |
C8B | 0.7491 (4) | 0.84082 (16) | 0.4515 (3) | 0.0254 (7) | |
C9B | 0.5592 (4) | 0.75132 (15) | 0.3840 (3) | 0.0211 (6) | |
C10B | 0.6424 (4) | 0.62857 (15) | 0.5582 (3) | 0.0250 (6) | |
C11B | 0.5927 (4) | 0.58857 (17) | 0.6427 (4) | 0.0314 (7) | |
H11B | 0.5740 | 0.6035 | 0.7201 | 0.038* | |
C12B | 0.5714 (5) | 0.52710 (19) | 0.6113 (4) | 0.0433 (9) | |
H12B | 0.5373 | 0.5008 | 0.6673 | 0.052* | |
C13B | 0.6003 (6) | 0.50458 (18) | 0.4975 (4) | 0.0448 (10) | |
H13B | 0.5871 | 0.4630 | 0.4775 | 0.054* | |
C14B | 0.6494 (5) | 0.54392 (18) | 0.4123 (4) | 0.0394 (9) | |
H14B | 0.6695 | 0.5286 | 0.3358 | 0.047* | |
C15B | 0.6681 (4) | 0.60575 (17) | 0.4415 (3) | 0.0291 (7) | |
H15B | 0.6979 | 0.6322 | 0.3833 | 0.035* | |
C16B | 0.3368 (4) | 0.72624 (15) | 0.2058 (3) | 0.0219 (6) | |
H16B | 0.3536 | 0.7636 | 0.1692 | 0.026* | |
C17B | 0.2019 (4) | 0.68968 (15) | 0.1295 (3) | 0.0225 (6) | |
C18B | 0.1459 (4) | 0.63051 (14) | 0.1581 (3) | 0.0221 (6) | |
C19B | 0.2011 (4) | 0.58836 (17) | 0.2628 (3) | 0.0282 (7) | |
H19B | 0.2962 | 0.5954 | 0.3333 | 0.034* | |
C20B | 0.1103 (5) | 0.53570 (17) | 0.2591 (4) | 0.0346 (8) | |
H20B | 0.1458 | 0.5070 | 0.3281 | 0.042* | |
C21B | −0.0332 (5) | 0.52460 (18) | 0.1541 (4) | 0.0361 (8) | |
H21B | −0.0916 | 0.4890 | 0.1553 | 0.043* | |
C22B | −0.0899 (4) | 0.56541 (17) | 0.0489 (4) | 0.0295 (7) | |
H22B | −0.1851 | 0.5580 | −0.0212 | 0.035* | |
C23B | 0.0021 (4) | 0.61853 (16) | 0.0524 (3) | 0.0237 (6) | |
C24B | 0.0910 (4) | 0.70917 (16) | 0.0096 (3) | 0.0248 (6) | |
H24B | 0.0971 | 0.7461 | −0.0330 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0249 (4) | 0.0210 (4) | 0.0232 (3) | 0.0012 (3) | 0.0033 (3) | 0.0041 (3) |
O1A | 0.0297 (12) | 0.0381 (14) | 0.0193 (11) | −0.0017 (10) | −0.0002 (9) | 0.0041 (10) |
N1A | 0.0206 (13) | 0.0236 (13) | 0.0180 (12) | 0.0000 (10) | 0.0032 (10) | −0.0002 (10) |
N2A | 0.0220 (13) | 0.0421 (17) | 0.0186 (12) | 0.0033 (12) | −0.0016 (10) | −0.0068 (11) |
C1A | 0.0155 (13) | 0.0277 (16) | 0.0197 (14) | 0.0028 (11) | 0.0009 (11) | 0.0023 (12) |
C2A | 0.0176 (14) | 0.0209 (15) | 0.0225 (14) | 0.0003 (11) | 0.0037 (11) | −0.0015 (11) |
C3A | 0.0213 (15) | 0.0211 (16) | 0.0259 (15) | 0.0023 (12) | 0.0053 (12) | −0.0040 (11) |
C4A | 0.0289 (17) | 0.0267 (17) | 0.0282 (16) | 0.0002 (13) | −0.0020 (13) | −0.0019 (13) |
C5A | 0.0288 (17) | 0.0314 (19) | 0.0304 (17) | 0.0001 (14) | −0.0009 (13) | −0.0074 (14) |
C6A | 0.0280 (17) | 0.0291 (18) | 0.047 (2) | −0.0054 (14) | 0.0068 (15) | −0.0081 (15) |
C7A | 0.0305 (17) | 0.0210 (16) | 0.0379 (18) | −0.0019 (13) | 0.0091 (14) | −0.0004 (13) |
C8A | 0.0213 (14) | 0.0217 (16) | 0.0290 (15) | 0.0018 (12) | 0.0040 (12) | −0.0024 (12) |
C9A | 0.0224 (15) | 0.0210 (15) | 0.0191 (14) | 0.0022 (11) | 0.0070 (12) | 0.0003 (11) |
C10A | 0.0214 (13) | 0.0208 (15) | 0.0208 (13) | 0.0034 (11) | 0.0000 (11) | 0.0060 (11) |
C11A | 0.0312 (18) | 0.0325 (19) | 0.0280 (16) | 0.0019 (14) | 0.0034 (14) | 0.0096 (14) |
C12A | 0.040 (2) | 0.0287 (19) | 0.046 (2) | −0.0044 (15) | 0.0013 (17) | 0.0151 (16) |
C13A | 0.049 (2) | 0.0215 (18) | 0.046 (2) | 0.0053 (15) | −0.0089 (18) | 0.0000 (15) |
C14A | 0.044 (2) | 0.036 (2) | 0.0315 (18) | 0.0114 (16) | 0.0022 (16) | −0.0061 (15) |
C15A | 0.0310 (17) | 0.0261 (17) | 0.0271 (15) | 0.0058 (13) | 0.0044 (13) | 0.0052 (13) |
C16A | 0.0220 (15) | 0.0228 (15) | 0.0189 (13) | 0.0017 (12) | 0.0062 (11) | 0.0007 (11) |
C17A | 0.0206 (15) | 0.0260 (16) | 0.0201 (14) | 0.0036 (12) | 0.0045 (12) | 0.0007 (11) |
C18A | 0.0207 (14) | 0.0249 (16) | 0.0218 (14) | 0.0034 (12) | 0.0060 (12) | −0.0033 (12) |
C19A | 0.0279 (16) | 0.0279 (18) | 0.0277 (16) | 0.0026 (14) | 0.0040 (13) | −0.0002 (13) |
C20A | 0.040 (2) | 0.0300 (19) | 0.043 (2) | 0.0006 (15) | 0.0150 (17) | 0.0023 (15) |
C21A | 0.0339 (19) | 0.0302 (19) | 0.053 (2) | −0.0053 (15) | 0.0188 (17) | −0.0076 (16) |
C22A | 0.0235 (17) | 0.041 (2) | 0.0380 (19) | −0.0042 (14) | 0.0086 (14) | −0.0160 (16) |
C23A | 0.0223 (15) | 0.0343 (18) | 0.0229 (15) | 0.0036 (13) | 0.0059 (12) | −0.0088 (13) |
C24A | 0.0225 (14) | 0.0328 (18) | 0.0207 (15) | 0.0023 (13) | 0.0045 (12) | −0.0005 (12) |
S1B | 0.0254 (3) | 0.0217 (4) | 0.0228 (3) | −0.0004 (3) | 0.0030 (3) | 0.0029 (3) |
O1B | 0.0328 (13) | 0.0339 (13) | 0.0211 (11) | 0.0015 (10) | 0.0012 (9) | 0.0000 (10) |
N1B | 0.0209 (14) | 0.0230 (13) | 0.0214 (12) | 0.0019 (11) | 0.0054 (10) | 0.0016 (10) |
N2B | 0.0211 (13) | 0.0312 (15) | 0.0196 (12) | 0.0012 (11) | −0.0005 (10) | −0.0007 (11) |
C1B | 0.0182 (14) | 0.0271 (17) | 0.0189 (15) | 0.0042 (11) | 0.0015 (11) | 0.0010 (12) |
C2B | 0.0202 (14) | 0.0233 (16) | 0.0212 (14) | 0.0035 (12) | 0.0039 (11) | −0.0013 (12) |
C3B | 0.0224 (15) | 0.0212 (15) | 0.0263 (15) | 0.0027 (12) | 0.0028 (12) | −0.0026 (12) |
C4B | 0.0294 (17) | 0.0255 (18) | 0.0329 (17) | 0.0036 (13) | −0.0057 (14) | −0.0063 (13) |
C5B | 0.0284 (18) | 0.0277 (18) | 0.0350 (18) | 0.0012 (13) | −0.0015 (14) | −0.0104 (14) |
C6B | 0.0287 (18) | 0.0307 (19) | 0.049 (2) | −0.0063 (14) | 0.0111 (16) | −0.0138 (16) |
C7B | 0.0325 (19) | 0.0227 (17) | 0.0376 (19) | −0.0051 (14) | 0.0085 (15) | −0.0031 (13) |
C8B | 0.0238 (15) | 0.0218 (16) | 0.0279 (16) | −0.0006 (12) | 0.0045 (13) | −0.0050 (12) |
C9B | 0.0218 (14) | 0.0205 (14) | 0.0216 (14) | 0.0030 (12) | 0.0078 (12) | 0.0029 (11) |
C10B | 0.0194 (14) | 0.0252 (17) | 0.0274 (15) | 0.0037 (11) | 0.0029 (12) | 0.0032 (12) |
C11B | 0.0297 (17) | 0.0314 (18) | 0.0314 (17) | 0.0037 (14) | 0.0068 (13) | 0.0058 (13) |
C12B | 0.041 (2) | 0.033 (2) | 0.049 (2) | −0.0053 (16) | 0.0049 (17) | 0.0124 (17) |
C13B | 0.050 (2) | 0.0216 (17) | 0.049 (2) | 0.0006 (15) | −0.0041 (18) | 0.0004 (15) |
C14B | 0.042 (2) | 0.0323 (19) | 0.0360 (19) | 0.0076 (16) | 0.0002 (16) | −0.0066 (15) |
C15B | 0.0277 (16) | 0.0301 (18) | 0.0262 (15) | 0.0032 (13) | 0.0037 (12) | 0.0006 (13) |
C16B | 0.0219 (15) | 0.0235 (15) | 0.0207 (14) | 0.0029 (12) | 0.0071 (12) | 0.0032 (11) |
C17B | 0.0218 (15) | 0.0262 (16) | 0.0191 (14) | 0.0052 (12) | 0.0060 (11) | 0.0010 (11) |
C18B | 0.0195 (14) | 0.0231 (16) | 0.0231 (14) | 0.0029 (12) | 0.0057 (12) | −0.0049 (12) |
C19B | 0.0286 (17) | 0.0259 (17) | 0.0268 (16) | 0.0043 (13) | 0.0039 (13) | 0.0018 (13) |
C20B | 0.043 (2) | 0.0249 (18) | 0.0335 (18) | 0.0040 (15) | 0.0083 (15) | 0.0054 (14) |
C21B | 0.039 (2) | 0.0236 (17) | 0.047 (2) | −0.0053 (15) | 0.0145 (16) | −0.0045 (15) |
C22B | 0.0255 (16) | 0.0292 (17) | 0.0306 (16) | −0.0038 (13) | 0.0044 (13) | −0.0082 (13) |
C23B | 0.0231 (15) | 0.0243 (16) | 0.0226 (14) | 0.0045 (13) | 0.0054 (12) | −0.0041 (12) |
C24B | 0.0243 (15) | 0.0279 (16) | 0.0204 (14) | 0.0017 (13) | 0.0045 (12) | 0.0024 (12) |
S1A—C8A | 1.732 (3) | S1B—C8B | 1.729 (3) |
S1A—C9A | 1.754 (3) | S1B—C9B | 1.756 (3) |
O1A—C1A | 1.223 (4) | O1B—C1B | 1.232 (4) |
N1A—C9A | 1.375 (4) | N1B—C9B | 1.379 (4) |
N1A—C16A | 1.284 (4) | N1B—C16B | 1.286 (4) |
N2A—H2A | 0.8600 | N2B—H2B | 0.8600 |
N2A—C23A | 1.381 (5) | N2B—C23B | 1.378 (4) |
N2A—C24A | 1.352 (5) | N2B—C24B | 1.351 (4) |
C1A—C2A | 1.482 (4) | C1B—C2B | 1.479 (4) |
C1A—C10A | 1.493 (5) | C1B—C10B | 1.488 (5) |
C2A—C3A | 1.447 (4) | C2B—C3B | 1.448 (5) |
C2A—C9A | 1.386 (4) | C2B—C9B | 1.388 (4) |
C3A—C4A | 1.510 (4) | C3B—C4B | 1.517 (4) |
C3A—C8A | 1.352 (5) | C3B—C8B | 1.353 (5) |
C4A—H4AA | 0.9700 | C4B—H4BA | 0.9700 |
C4A—H4AB | 0.9700 | C4B—H4BB | 0.9700 |
C4A—C5A | 1.530 (5) | C4B—C5B | 1.517 (5) |
C5A—H5AA | 0.9700 | C5B—H5BA | 0.9700 |
C5A—H5AB | 0.9700 | C5B—H5BB | 0.9700 |
C5A—C6A | 1.519 (6) | C5B—C6B | 1.522 (6) |
C6A—H6AA | 0.9700 | C6B—H6BA | 0.9700 |
C6A—H6AB | 0.9700 | C6B—H6BB | 0.9700 |
C6A—C7A | 1.528 (5) | C6B—C7B | 1.533 (5) |
C7A—H7AA | 0.9700 | C7B—H7BA | 0.9700 |
C7A—H7AB | 0.9700 | C7B—H7BB | 0.9700 |
C7A—C8A | 1.508 (5) | C7B—C8B | 1.506 (5) |
C10A—C11A | 1.405 (5) | C10B—C11B | 1.399 (5) |
C10A—C15A | 1.387 (5) | C10B—C15B | 1.394 (5) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C11A—C12A | 1.379 (6) | C11B—C12B | 1.379 (6) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C12A—C13A | 1.380 (7) | C12B—C13B | 1.377 (7) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C13A—C14A | 1.389 (7) | C13B—C14B | 1.393 (6) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C14A—C15A | 1.385 (5) | C14B—C15B | 1.382 (5) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C16A—C17A | 1.432 (4) | C16B—C17B | 1.434 (5) |
C17A—C18A | 1.439 (5) | C17B—C18B | 1.443 (5) |
C17A—C24A | 1.381 (4) | C17B—C24B | 1.384 (4) |
C18A—C19A | 1.396 (5) | C18B—C19B | 1.393 (5) |
C18A—C23A | 1.410 (4) | C18B—C23B | 1.407 (4) |
C19A—H19A | 0.9300 | C19B—H19B | 0.9300 |
C19A—C20A | 1.385 (5) | C19B—C20B | 1.386 (5) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C20A—C21A | 1.399 (6) | C20B—C21B | 1.398 (6) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C21A—C22A | 1.381 (6) | C21B—C22B | 1.378 (5) |
C22A—H22A | 0.9300 | C22B—H22B | 0.9300 |
C22A—C23A | 1.391 (5) | C22B—C23B | 1.401 (5) |
C24A—H24A | 0.9300 | C24B—H24B | 0.9300 |
C8A—S1A—C9A | 91.80 (15) | C8B—S1B—C9B | 92.09 (16) |
C16A—N1A—C9A | 119.5 (3) | C16B—N1B—C9B | 118.2 (3) |
C23A—N2A—H2A | 125.4 | C23B—N2B—H2B | 125.6 |
C24A—N2A—H2A | 125.4 | C24B—N2B—H2B | 125.6 |
C24A—N2A—C23A | 109.2 (3) | C24B—N2B—C23B | 108.7 (3) |
O1A—C1A—C2A | 120.6 (3) | O1B—C1B—C2B | 118.7 (3) |
O1A—C1A—C10A | 118.4 (3) | O1B—C1B—C10B | 117.9 (3) |
C2A—C1A—C10A | 121.0 (3) | C2B—C1B—C10B | 123.4 (3) |
C3A—C2A—C1A | 122.8 (3) | C3B—C2B—C1B | 122.1 (3) |
C9A—C2A—C1A | 124.1 (3) | C9B—C2B—C1B | 125.0 (3) |
C9A—C2A—C3A | 112.9 (3) | C9B—C2B—C3B | 112.7 (3) |
C2A—C3A—C4A | 126.5 (3) | C2B—C3B—C4B | 126.7 (3) |
C8A—C3A—C2A | 112.4 (3) | C8B—C3B—C2B | 112.9 (3) |
C8A—C3A—C4A | 121.1 (3) | C8B—C3B—C4B | 120.4 (3) |
C3A—C4A—H4AA | 109.5 | C3B—C4B—H4BA | 109.4 |
C3A—C4A—H4AB | 109.5 | C3B—C4B—H4BB | 109.4 |
C3A—C4A—C5A | 110.7 (3) | C3B—C4B—C5B | 111.2 (3) |
H4AA—C4A—H4AB | 108.1 | H4BA—C4B—H4BB | 108.0 |
C5A—C4A—H4AA | 109.5 | C5B—C4B—H4BA | 109.4 |
C5A—C4A—H4AB | 109.5 | C5B—C4B—H4BB | 109.4 |
C4A—C5A—H5AA | 109.3 | C4B—C5B—H5BA | 109.2 |
C4A—C5A—H5AB | 109.3 | C4B—C5B—H5BB | 109.2 |
H5AA—C5A—H5AB | 107.9 | C4B—C5B—C6B | 112.2 (3) |
C6A—C5A—C4A | 111.8 (3) | H5BA—C5B—H5BB | 107.9 |
C6A—C5A—H5AA | 109.3 | C6B—C5B—H5BA | 109.2 |
C6A—C5A—H5AB | 109.3 | C6B—C5B—H5BB | 109.2 |
C5A—C6A—H6AA | 109.6 | C5B—C6B—H6BA | 109.4 |
C5A—C6A—H6AB | 109.6 | C5B—C6B—H6BB | 109.4 |
C5A—C6A—C7A | 110.3 (3) | C5B—C6B—C7B | 111.0 (3) |
H6AA—C6A—H6AB | 108.1 | H6BA—C6B—H6BB | 108.0 |
C7A—C6A—H6AA | 109.6 | C7B—C6B—H6BA | 109.4 |
C7A—C6A—H6AB | 109.6 | C7B—C6B—H6BB | 109.4 |
C6A—C7A—H7AA | 109.8 | C6B—C7B—H7BA | 109.8 |
C6A—C7A—H7AB | 109.8 | C6B—C7B—H7BB | 109.8 |
H7AA—C7A—H7AB | 108.2 | H7BA—C7B—H7BB | 108.2 |
C8A—C7A—C6A | 109.6 (3) | C8B—C7B—C6B | 109.4 (3) |
C8A—C7A—H7AA | 109.8 | C8B—C7B—H7BA | 109.8 |
C8A—C7A—H7AB | 109.8 | C8B—C7B—H7BB | 109.8 |
C3A—C8A—S1A | 112.6 (2) | C3B—C8B—S1B | 112.3 (3) |
C3A—C8A—C7A | 126.5 (3) | C3B—C8B—C7B | 127.3 (3) |
C7A—C8A—S1A | 120.9 (2) | C7B—C8B—S1B | 120.4 (3) |
N1A—C9A—S1A | 123.9 (2) | N1B—C9B—S1B | 122.8 (2) |
N1A—C9A—C2A | 125.8 (3) | N1B—C9B—C2B | 127.0 (3) |
C2A—C9A—S1A | 110.2 (2) | C2B—C9B—S1B | 110.1 (2) |
C11A—C10A—C1A | 118.6 (3) | C11B—C10B—C1B | 118.0 (3) |
C15A—C10A—C1A | 121.9 (3) | C15B—C10B—C1B | 122.4 (3) |
C15A—C10A—C11A | 119.3 (3) | C15B—C10B—C11B | 119.3 (3) |
C10A—C11A—H11A | 120.1 | C10B—C11B—H11B | 119.9 |
C12A—C11A—C10A | 119.8 (4) | C12B—C11B—C10B | 120.2 (4) |
C12A—C11A—H11A | 120.1 | C12B—C11B—H11B | 119.9 |
C11A—C12A—H12A | 119.7 | C11B—C12B—H12B | 119.9 |
C11A—C12A—C13A | 120.6 (4) | C13B—C12B—C11B | 120.3 (4) |
C13A—C12A—H12A | 119.7 | C13B—C12B—H12B | 119.9 |
C12A—C13A—H13A | 120.1 | C12B—C13B—H13B | 119.9 |
C12A—C13A—C14A | 119.9 (4) | C12B—C13B—C14B | 120.2 (4) |
C14A—C13A—H13A | 120.1 | C14B—C13B—H13B | 119.9 |
C13A—C14A—H14A | 120.0 | C13B—C14B—H14B | 120.0 |
C15A—C14A—C13A | 120.0 (4) | C15B—C14B—C13B | 120.0 (4) |
C15A—C14A—H14A | 120.0 | C15B—C14B—H14B | 120.0 |
C10A—C15A—H15A | 119.8 | C10B—C15B—H15B | 120.0 |
C14A—C15A—C10A | 120.4 (3) | C14B—C15B—C10B | 120.1 (4) |
C14A—C15A—H15A | 119.8 | C14B—C15B—H15B | 120.0 |
N1A—C16A—H16A | 118.4 | N1B—C16B—H16B | 117.7 |
N1A—C16A—C17A | 123.2 (3) | N1B—C16B—C17B | 124.6 (3) |
C17A—C16A—H16A | 118.4 | C17B—C16B—H16B | 117.7 |
C16A—C17A—C18A | 129.8 (3) | C16B—C17B—C18B | 130.7 (3) |
C24A—C17A—C16A | 123.7 (3) | C24B—C17B—C16B | 123.1 (3) |
C24A—C17A—C18A | 106.4 (3) | C24B—C17B—C18B | 106.1 (3) |
C19A—C18A—C17A | 134.3 (3) | C19B—C18B—C17B | 134.2 (3) |
C19A—C18A—C23A | 119.3 (3) | C19B—C18B—C23B | 119.7 (3) |
C23A—C18A—C17A | 106.4 (3) | C23B—C18B—C17B | 106.1 (3) |
C18A—C19A—H19A | 120.7 | C18B—C19B—H19B | 120.9 |
C20A—C19A—C18A | 118.6 (3) | C20B—C19B—C18B | 118.1 (3) |
C20A—C19A—H19A | 120.7 | C20B—C19B—H19B | 120.9 |
C19A—C20A—H20A | 119.4 | C19B—C20B—H20B | 119.2 |
C19A—C20A—C21A | 121.3 (4) | C19B—C20B—C21B | 121.6 (4) |
C21A—C20A—H20A | 119.4 | C21B—C20B—H20B | 119.2 |
C20A—C21A—H21A | 119.4 | C20B—C21B—H21B | 119.3 |
C22A—C21A—C20A | 121.1 (4) | C22B—C21B—C20B | 121.3 (4) |
C22A—C21A—H21A | 119.4 | C22B—C21B—H21B | 119.3 |
C21A—C22A—H22A | 121.2 | C21B—C22B—H22B | 121.5 |
C21A—C22A—C23A | 117.6 (3) | C21B—C22B—C23B | 117.1 (3) |
C23A—C22A—H22A | 121.2 | C23B—C22B—H22B | 121.5 |
N2A—C23A—C18A | 107.8 (3) | N2B—C23B—C18B | 108.6 (3) |
N2A—C23A—C22A | 130.0 (3) | N2B—C23B—C22B | 129.3 (3) |
C22A—C23A—C18A | 122.1 (3) | C22B—C23B—C18B | 122.1 (3) |
N2A—C24A—C17A | 110.2 (3) | N2B—C24B—C17B | 110.5 (3) |
N2A—C24A—H24A | 124.9 | N2B—C24B—H24B | 124.8 |
C17A—C24A—H24A | 124.9 | C17B—C24B—H24B | 124.8 |
O1A—C1A—C2A—C3A | −28.7 (5) | O1B—C1B—C2B—C3B | 29.5 (5) |
O1A—C1A—C2A—C9A | 146.2 (3) | O1B—C1B—C2B—C9B | −144.7 (3) |
O1A—C1A—C10A—C11A | −34.1 (4) | O1B—C1B—C10B—C11B | 26.2 (4) |
O1A—C1A—C10A—C15A | 140.5 (3) | O1B—C1B—C10B—C15B | −148.1 (3) |
N1A—C16A—C17A—C18A | −1.1 (5) | N1B—C16B—C17B—C18B | −0.6 (6) |
N1A—C16A—C17A—C24A | −177.3 (3) | N1B—C16B—C17B—C24B | 175.6 (3) |
C1A—C2A—C3A—C4A | −0.2 (5) | C1B—C2B—C3B—C4B | 4.6 (5) |
C1A—C2A—C3A—C8A | 178.3 (3) | C1B—C2B—C3B—C8B | −176.2 (3) |
C1A—C2A—C9A—S1A | −176.7 (2) | C1B—C2B—C9B—S1B | 174.9 (3) |
C1A—C2A—C9A—N1A | −0.3 (5) | C1B—C2B—C9B—N1B | −2.4 (5) |
C1A—C10A—C11A—C12A | 175.9 (3) | C1B—C10B—C11B—C12B | −173.7 (3) |
C1A—C10A—C15A—C14A | −173.2 (3) | C1B—C10B—C15B—C14B | 172.2 (3) |
C2A—C1A—C10A—C11A | 148.3 (3) | C2B—C1B—C10B—C11B | −156.3 (3) |
C2A—C1A—C10A—C15A | −37.1 (4) | C2B—C1B—C10B—C15B | 29.4 (5) |
C2A—C3A—C4A—C5A | 165.5 (3) | C2B—C3B—C4B—C5B | −166.0 (3) |
C2A—C3A—C8A—S1A | −3.0 (4) | C2B—C3B—C8B—S1B | 1.8 (4) |
C2A—C3A—C8A—C7A | 176.6 (3) | C2B—C3B—C8B—C7B | −176.5 (3) |
C3A—C2A—C9A—S1A | −1.4 (3) | C3B—C2B—C9B—S1B | 0.2 (3) |
C3A—C2A—C9A—N1A | 175.0 (3) | C3B—C2B—C9B—N1B | −177.1 (3) |
C3A—C4A—C5A—C6A | 46.8 (4) | C3B—C4B—C5B—C6B | −47.0 (4) |
C4A—C3A—C8A—S1A | 175.6 (3) | C4B—C3B—C8B—S1B | −178.9 (3) |
C4A—C3A—C8A—C7A | −4.8 (5) | C4B—C3B—C8B—C7B | 2.8 (6) |
C4A—C5A—C6A—C7A | −64.8 (4) | C4B—C5B—C6B—C7B | 63.3 (4) |
C5A—C6A—C7A—C8A | 44.4 (4) | C5B—C6B—C7B—C8B | −42.8 (4) |
C6A—C7A—C8A—S1A | 168.1 (2) | C6B—C7B—C8B—S1B | −166.6 (3) |
C6A—C7A—C8A—C3A | −11.4 (5) | C6B—C7B—C8B—C3B | 11.6 (5) |
C8A—S1A—C9A—N1A | −176.7 (3) | C8B—S1B—C9B—N1B | 178.1 (3) |
C8A—S1A—C9A—C2A | −0.2 (3) | C8B—S1B—C9B—C2B | 0.7 (3) |
C8A—C3A—C4A—C5A | −12.9 (5) | C8B—C3B—C4B—C5B | 14.8 (5) |
C9A—S1A—C8A—C3A | 1.8 (3) | C9B—S1B—C8B—C3B | −1.5 (3) |
C9A—S1A—C8A—C7A | −177.8 (3) | C9B—S1B—C8B—C7B | 177.0 (3) |
C9A—N1A—C16A—C17A | 177.6 (3) | C9B—N1B—C16B—C17B | −179.1 (3) |
C9A—C2A—C3A—C4A | −175.6 (3) | C9B—C2B—C3B—C4B | 179.4 (3) |
C9A—C2A—C3A—C8A | 2.9 (4) | C9B—C2B—C3B—C8B | −1.4 (4) |
C10A—C1A—C2A—C3A | 148.8 (3) | C10B—C1B—C2B—C3B | −148.0 (3) |
C10A—C1A—C2A—C9A | −36.3 (4) | C10B—C1B—C2B—C9B | 37.8 (5) |
C10A—C11A—C12A—C13A | −3.1 (5) | C10B—C11B—C12B—C13B | 0.6 (6) |
C11A—C10A—C15A—C14A | 1.3 (5) | C11B—C10B—C15B—C14B | −2.0 (5) |
C11A—C12A—C13A—C14A | 2.6 (6) | C11B—C12B—C13B—C14B | −0.8 (6) |
C12A—C13A—C14A—C15A | −0.1 (6) | C12B—C13B—C14B—C15B | −0.4 (6) |
C13A—C14A—C15A—C10A | −1.9 (5) | C13B—C14B—C15B—C10B | 1.8 (5) |
C15A—C10A—C11A—C12A | 1.1 (5) | C15B—C10B—C11B—C12B | 0.8 (5) |
C16A—N1A—C9A—S1A | −0.8 (4) | C16B—N1B—C9B—S1B | 0.2 (4) |
C16A—N1A—C9A—C2A | −176.8 (3) | C16B—N1B—C9B—C2B | 177.2 (3) |
C16A—C17A—C18A—C19A | 2.3 (6) | C16B—C17B—C18B—C19B | −1.9 (6) |
C16A—C17A—C18A—C23A | −176.5 (3) | C16B—C17B—C18B—C23B | 176.2 (3) |
C16A—C17A—C24A—N2A | 177.2 (3) | C16B—C17B—C24B—N2B | −177.0 (3) |
C17A—C18A—C19A—C20A | −178.0 (4) | C17B—C18B—C19B—C20B | 177.6 (4) |
C17A—C18A—C23A—N2A | −0.6 (3) | C17B—C18B—C23B—N2B | 0.9 (3) |
C17A—C18A—C23A—C22A | 178.5 (3) | C17B—C18B—C23B—C22B | −177.8 (3) |
C18A—C17A—C24A—N2A | 0.3 (4) | C18B—C17B—C24B—N2B | 0.0 (4) |
C18A—C19A—C20A—C21A | −0.4 (6) | C18B—C19B—C20B—C21B | −0.2 (6) |
C19A—C18A—C23A—N2A | −179.5 (3) | C19B—C18B—C23B—N2B | 179.3 (3) |
C19A—C18A—C23A—C22A | −0.5 (5) | C19B—C18B—C23B—C22B | 0.7 (5) |
C19A—C20A—C21A—C22A | 0.1 (6) | C19B—C20B—C21B—C22B | 0.6 (6) |
C20A—C21A—C22A—C23A | 0.0 (6) | C20B—C21B—C22B—C23B | −0.3 (6) |
C21A—C22A—C23A—N2A | 179.0 (3) | C21B—C22B—C23B—N2B | −178.7 (3) |
C21A—C22A—C23A—C18A | 0.2 (5) | C21B—C22B—C23B—C18B | −0.3 (5) |
C23A—N2A—C24A—C17A | −0.6 (4) | C23B—N2B—C24B—C17B | 0.6 (4) |
C23A—C18A—C19A—C20A | 0.6 (5) | C23B—C18B—C19B—C20B | −0.4 (5) |
C24A—N2A—C23A—C18A | 0.7 (4) | C24B—N2B—C23B—C18B | −0.9 (4) |
C24A—N2A—C23A—C22A | −178.2 (3) | C24B—N2B—C23B—C22B | 177.6 (3) |
C24A—C17A—C18A—C19A | 178.9 (4) | C24B—C17B—C18B—C19B | −178.6 (4) |
C24A—C17A—C18A—C23A | 0.2 (3) | C24B—C17B—C18B—C23B | −0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O1Ai | 0.86 | 2.01 | 2.866 (4) | 175 |
N2B—H2B···O1Bii | 0.86 | 2.00 | 2.835 (3) | 163 |
Symmetry codes: (i) x+1, y, z+1; (ii) x−1, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O1Ai | 0.86 | 2.01 | 2.866 (4) | 174.7 |
N2B—H2B···O1Bii | 0.86 | 2.00 | 2.835 (3) | 162.6 |
Symmetry codes: (i) x+1, y, z+1; (ii) x−1, y, z−1. |
Acknowledgements
MK is grateful to the CPEPA–UGC for the award of a JRF and thanks th University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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2-Aminothiophene derivatives have been used in a number of applications in pesticides, dyes and pharmaceuticals. A review on the synthesis and properties of these compounds was reported by Sabnis et al. ( 1999)and more recently by Puterová et al. (2010). Substituted 2-aminothiophenes are active as allosteric enhancers at the human A1 adenosine receptor (Cannito et al.,1990; Nikolakopoulos et al., 2006; Lütjens et al., 2005). Schiff base compounds are an important class of compounds both synthetically and biologically. These compounds show biological activities including antibacterial, antifungal, anticancer and herbicidal activities (Desai et al., 2001; Karia & Parsania, 1999; Samadhiya & Halve, 2001; Singh & Dash, 1988). Furthermore, Schiff bases are utilized as starting materials in the synthesis of compounds of industrial (Aydogan et al., 2001) and biological interest such as /b-lactams (Taggi et al., 2002). The crystal structures and molecular structures of two 2-aminothiphenes have been previously reported by our group (Kubicki et al., 2012). In continuation of our work on schiff base derivatives of 2-aminothiophenes, we report here the crystal structure of the title compound, C24H20N2OS.
The title compound crystallizes with two independent molecules in the asymmetric unit (A and B) (Fig. 1). In each of the molecules, the cyclohexene rings adopt half-chair conformations (puckering parameters Q, θ, and ϕ = 0.508 (4)Å, 53.1 (5)° and 149.2 (5)° (A); Q, θ, and ϕ = 0.492 (4)Å, 128.3 (5)° and 327.5 (6)° (B), respectively; Cremer & Pople, 1975). The mean plane of the indole ring is twisted from that of the phenyl and thiophene ringsby 69.0 (7)° (A); 65.4 (9)° (B) and 8.3 (5)° (A); 6.7 (5)° (B), respectively. The dihedral angles between the mean plane of the phenyl rings and thiophene rings is 63.0 (4)° (A) and 58.8 (9)° (B), respectively. Bond lengths are in normal ranges (Allen et al., 1987). N—H···O intermolecular hydrogen bonds influence the crystal packing forming an infinite 1D chain along [1 0 1] (Fig. 2). In addition, weak Cg–Cg π–π stacking interactions are observed involving the thiophene rings and pyrrole rings of the two molecules with the shortest intercentroid distance of 3.468 (2)Å.