Crystal structure and synthesis of 3-(1H-pyrrol-2-yl)-1-(thio­phen-2-yl)propanone

The mol­ecule is essentially planar with a maximum deviation of 0.085 Å from the mean plane through all non-H atoms. In the crystal, N—H...O hydrogen bonds involving the pyrrole amine and the ketone carbonyl O atoms link the mol­ecules into [100] ribbons which form offset stacks along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.082
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 and s.u.        0.04 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-(1H-Pyrrol-2-yl)-1-(thiophen-2-yl)propanone

Crystal data

C11H9NOS	Dx = 1.425 Mg m^−3
Mr = 203.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 9918 reflections
a = 11.1559 (3) Å	θ = 3.7–27.5°
b = 3.9258 (1) Å	µ = 0.30 mm^−1
c = 21.6293 (6) Å	T = 100 K
V = 947.27 (4) Å^3	Triangular, yellow
Z = 4	0.2 × 0.09 × 0.07 mm
F(000) = 424

Data collection

Bruker SMART APEXII area detector diffractometer	2159 independent reflections
Radiation source: standard sealed X-ray tube, Siemens, KFF Mo 2K -90 C	2070 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 7.9 pixels mm^-1	θmax = 27.5°, θmin = 1.9°
ω and φ scans	h = −14→14
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −5→5
Tmin = 0.658, Tmax = 0.746	l = −27→28
25996 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 0.3056P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.28 e Å^−3
2159 reflections	Δρmin = −0.17 e Å^−3
131 parameters	Absolute structure: Flack x determined using 956 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.00 (4)
Primary atom site location: dual

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4383 (3)	0.3593 (7)	0.30581 (13)	0.0220 (6)
H1	0.4090	0.2839	0.2669	0.026*
C2	0.5545 (3)	0.3241 (7)	0.32434 (13)	0.0199 (5)
H2	0.6149	0.2208	0.2997	0.024*
C3	0.5754 (2)	0.4580 (6)	0.38425 (12)	0.0146 (5)
H3	0.6510	0.4546	0.4045	0.018*
C4	0.4712 (2)	0.5956 (7)	0.40983 (12)	0.0154 (5)
C5	0.4521 (2)	0.7623 (7)	0.46958 (11)	0.0158 (5)
C6	0.5566 (2)	0.7940 (7)	0.51008 (13)	0.0167 (5)
H6	0.6303	0.6917	0.4983	0.020*
C7	0.5498 (2)	0.9663 (7)	0.56396 (12)	0.0166 (5)
H7	0.4753	1.0719	0.5733	0.020*
C8	0.6436 (2)	1.0055 (7)	0.60829 (13)	0.0160 (5)
C9	0.6393 (2)	1.1517 (7)	0.66686 (12)	0.0183 (5)
H9	0.5713	1.2570	0.6852	0.022*
C10	0.7529 (3)	1.1168 (7)	0.69428 (12)	0.0195 (5)
H10	0.7758	1.1928	0.7343	0.023*
C11	0.8247 (2)	0.9509 (7)	0.65194 (13)	0.0182 (6)
H11	0.9065	0.8924	0.6579	0.022*
N1	0.7588 (2)	0.8850 (6)	0.60020 (11)	0.0179 (5)
H1A	0.787 (3)	0.791 (9)	0.5687 (16)	0.019 (8)*
O1	0.35144 (16)	0.8661 (6)	0.48409 (9)	0.0199 (4)
S1	0.35151 (5)	0.55340 (15)	0.36015 (3)	0.01928 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0338 (15)	0.0180 (12)	0.0144 (12)	−0.0026 (11)	−0.0025 (10)	0.0009 (10)
C2	0.0266 (13)	0.0172 (13)	0.0160 (12)	−0.0001 (10)	0.0048 (10)	−0.0005 (11)
C3	0.0173 (11)	0.0139 (11)	0.0126 (11)	−0.0020 (9)	0.0005 (9)	0.0009 (9)
C4	0.0187 (12)	0.0154 (12)	0.0120 (11)	−0.0046 (9)	−0.0014 (9)	0.0023 (9)
C5	0.0200 (12)	0.0166 (10)	0.0108 (11)	−0.0016 (10)	0.0010 (10)	0.0036 (10)
C6	0.0158 (11)	0.0201 (12)	0.0140 (11)	−0.0006 (10)	−0.0014 (10)	0.0010 (11)
C7	0.0188 (12)	0.0165 (12)	0.0146 (12)	−0.0002 (10)	0.0013 (10)	0.0030 (10)
C8	0.0195 (12)	0.0155 (12)	0.0130 (12)	−0.0010 (10)	0.0007 (9)	0.0016 (9)
C9	0.0244 (13)	0.0168 (12)	0.0138 (12)	0.0011 (10)	0.0017 (10)	−0.0013 (10)
C10	0.0274 (13)	0.0182 (12)	0.0129 (12)	−0.0024 (10)	−0.0025 (10)	−0.0010 (10)
C11	0.0194 (13)	0.0205 (13)	0.0149 (12)	−0.0040 (10)	−0.0010 (10)	0.0006 (10)
N1	0.0191 (11)	0.0218 (11)	0.0129 (11)	−0.0012 (9)	0.0016 (9)	−0.0015 (9)
O1	0.0183 (9)	0.0272 (9)	0.0143 (9)	0.0008 (8)	0.0013 (7)	0.0014 (8)
S1	0.0198 (3)	0.0223 (3)	0.0157 (3)	−0.0019 (2)	−0.0033 (3)	0.0002 (3)

Geometric parameters (Å, º)

C1—H1	0.9500	C6—C7	1.350 (4)
C1—C2	1.364 (4)	C7—H7	0.9500
C1—S1	1.702 (3)	C7—C8	1.428 (4)
C2—H2	0.9500	C8—C9	1.392 (4)
C2—C3	1.418 (4)	C8—N1	1.381 (3)
C3—H3	0.9500	C9—H9	0.9500
C3—C4	1.397 (4)	C9—C10	1.406 (4)
C4—C5	1.464 (3)	C10—H10	0.9500
C4—S1	1.722 (3)	C10—C11	1.380 (4)
C5—C6	1.463 (3)	C11—H11	0.9500
C5—O1	1.236 (3)	C11—N1	1.364 (4)
C6—H6	0.9500	N1—H1A	0.84 (4)
C2—C1—H1	123.7	C6—C7—C8	126.4 (3)
C2—C1—S1	112.5 (2)	C8—C7—H7	116.8
S1—C1—H1	123.7	C9—C8—C7	129.1 (2)
C1—C2—H2	123.6	N1—C8—C7	124.1 (2)
C1—C2—C3	112.8 (3)	N1—C8—C9	106.8 (2)
C3—C2—H2	123.6	C8—C9—H9	125.9
C2—C3—H3	124.2	C8—C9—C10	108.2 (2)
C4—C3—C2	111.6 (2)	C10—C9—H9	125.9
C4—C3—H3	124.2	C9—C10—H10	126.6
C3—C4—C5	130.0 (2)	C11—C10—C9	106.8 (2)
C3—C4—S1	111.2 (2)	C11—C10—H10	126.6
C5—C4—S1	118.77 (19)	C10—C11—H11	125.6
C6—C5—C4	116.8 (2)	N1—C11—C10	108.7 (2)
O1—C5—C4	120.2 (2)	N1—C11—H11	125.6
O1—C5—C6	122.9 (2)	C8—N1—H1A	127 (2)
C5—C6—H6	119.5	C11—N1—C8	109.4 (2)
C7—C6—C5	121.0 (2)	C11—N1—H1A	124 (2)
C7—C6—H6	119.5	C1—S1—C4	91.90 (14)
C6—C7—H7	116.8
C1—C2—C3—C4	−0.2 (3)	C7—C8—C9—C10	177.3 (3)
C2—C1—S1—C4	0.4 (2)	C7—C8—N1—C11	−177.4 (3)
C2—C3—C4—C5	−179.2 (2)	C8—C9—C10—C11	0.2 (3)
C2—C3—C4—S1	0.5 (3)	C9—C8—N1—C11	0.3 (3)
C3—C4—C5—C6	0.0 (4)	C9—C10—C11—N1	0.0 (3)
C3—C4—C5—O1	−179.5 (3)	C10—C11—N1—C8	−0.2 (3)
C3—C4—S1—C1	−0.5 (2)	N1—C8—C9—C10	−0.3 (3)
C4—C5—C6—C7	175.0 (2)	O1—C5—C6—C7	−5.6 (4)
C5—C4—S1—C1	179.2 (2)	S1—C1—C2—C3	−0.2 (3)
C5—C6—C7—C8	177.7 (2)	S1—C4—C5—C6	−179.67 (19)
C6—C7—C8—C9	−173.4 (3)	S1—C4—C5—O1	0.9 (3)
C6—C7—C8—N1	3.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.84 (4)	2.06 (4)	2.889 (3)	171 (3)
C6—H6···O1^i	0.95	2.50	3.396 (3)	158

Symmetry code: (i) x+1/2, −y+3/2, z.

Route mean square (r. m. s.) deviations and twist angles of the two five-membered heterocycles in 1 and the two derivatives known in literature (Li & Su, 1995; Ocak Ískeleli et al., 2005)

Compound	R. M. S. deviation (Å)	Twist angle (o)
1	0.056	2.87 (11)
2 (First independent molecule)	0.093 (2)	7.15 (6)
Second independent molecule	0.02 (2)	0.20 (15)
3 (First independent molecule)	0.104	8.41 (6)
Second independent molecule	0.122	11.11 (7)