(4-But­oxy­phen­yl)(1H-pyrrol-2-yl)methanone

Prakash, V.; Kapoor, K.; Shet Prakash, M.; Gupta, V.K.; Kant, R.

doi:10.1107/S1600536812017370

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1521

doi:10.1107/S1600536812017370

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(4-Butoxyphenyl)(1H-pyrrol-2-yl)methanone

V. Prakash,^a Kamini Kapoor,^b M. Shet Prakash,^c,^d Vivek K. Gupta ^b and Rajni Kant ^b ^*

^aShirdi Sai Engineering College, Anekal, Bangalore 562 106, India, ^bX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^cCentre for Advanced Materials, Tumkur University, Tumkur, India, and ^dDepartment of Chemistry, University College of Science, Tumkur University, Tumkur, India, Tumkur, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 2 April 2012; accepted 19 April 2012; online 25 April 2012)

The asymmetric unit of the title compound, C₁₅H₁₇NO₂, contains two independent molecules in which the dihedral angles between the pyrrole and benzene rings are 42.43 (9) and 45.70 (9)°. In both molecules, the butoxy chains are disordered over two sets of sites, with occupancy ratios of 0.701 (7):0.299 (7) and 0.869 (4):0.131 (4). Each molecule forms a dimer with an inversion-related molecule, through a pair of N—H⋯O hydrogen bonds. Weak C—H⋯O interactions link these dimers in the crystal structure.

Related literature

For background and applications of pyrrole derivatives, see: Fischer & Orth (1934 ); Mohamed et al. (2009 ). For related structures, see: English et al. (1980 ).

Experimental

Crystal data

C₁₅H₁₇NO₂
M_r = 243.30
Triclinic, $[P \overline 1]$
a = 9.4779 (4) Å
b = 11.4478 (5) Å
c = 13.1117 (7) Å
α = 95.155 (4)°
β = 104.118 (4)°
γ = 94.626 (3)°
V = 1366.31 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.935, T_max = 1.000
13503 measured reflections
5344 independent reflections
3273 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.160
S = 1.03
5344 reflections
385 parameters
38 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O7Aⁱ	0.93 (3)	2.00 (2)	2.864 (2)	154 (2)
N1B—H1B⋯O7Bⁱⁱ	0.88 (3)	2.06 (2)	2.834 (3)	146 (2)
C9B—H9B⋯O7Aⁱ	0.93	2.59	3.426 (3)	149
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+2, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812017370/bh2427sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017370/bh2427Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017370/bh2427Isup3.cml

checkCIF report

Comment top

The chemistry of pyrrole compounds and biological activities of the related compounds have been extensively studied (Fischer & Orth, 1934; Mohamed et al., 2009). With the view of biological importance, the title compound was synthesized and we report here its crystal structure.

The asymmetric unit of the title compound comprises of two crystallographically independent molecules, A and B (Fig. 1). The geometry of both independent molecules indicates a high degree of similarity in terms of their bond distances and bond angles. A comparison of these parameters with some related structures (English et al., 1980) indicates a good agreement. The pyrrole and benzene rings are not coplanar, the dihedral angle being 42.43 (9)° for molecule A and 45.70 (9)° for molecule B. The crystal packing is stabilized by N—H···O intermolecular hydrogen bonds, generating centrosymmetric dimers (Fig. 2). The crystal structure is further stabilized by weak C—H···O interactions between dimers.

Related literature top

For background and applications of pyrrole derivatives, see: Fischer & Orth (1934); Mohamed et al. (2009). For related structures, see: English et al. (1980).

Experimental top

Amide-phosphoryl complex was prepared by treating 1 equiv. of N,N-dimethyl-4-butoxy benzamide with 3 equiv. of POCl₃ at room temperature and stirred for 6 h. Subsequently, the reaction product was treated with pyrrole in anhydrous 1,2-dichloroethane at 25°C, stirred for another one hour, and left as such overnight. The resulting mixture was hydrolyzed using saturated sodium carbonate solution, followed by heating for 45 min., to afford the title compound. The compound was extracted with 1,2-dichloroethane and recrystallized from methanol. Single crystals of the compound were obtained by slow evaporation of a methanolic solution.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the title compound with thermal ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A molecular packing view of the title compound, showing intermolecular interactions. For clarity, hydrogen atoms not involved in hydrogen bonding have been omitted.

(4-Butoxyphenyl)(1H-pyrrol-2-yl)methanone top

Crystal data top

C₁₅H₁₇NO₂	Z = 4
M_r = 243.30	F(000) = 520
Triclinic, P1	D_x = 1.183 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4779 (4) Å	Cell parameters from 4854 reflections
b = 11.4478 (5) Å	θ = 3.5–29.0°
c = 13.1117 (7) Å	µ = 0.08 mm⁻¹
α = 95.155 (4)°	T = 293 K
β = 104.118 (4)°	Block, brown
γ = 94.626 (3)°	0.3 × 0.2 × 0.2 mm
V = 1366.31 (11) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5344 independent reflections
Radiation source: fine-focus sealed tube	3273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −14→14
T_min = 0.935, T_max = 1.000	l = −16→16
13503 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.0667P)² + 0.1402P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
5344 reflections	Δρ_max = 0.32 e Å⁻³
385 parameters	Δρ_min = −0.18 e Å⁻³
38 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.013 (2)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₇NO₂	γ = 94.626 (3)°
M_r = 243.30	V = 1366.31 (11) Å³
Triclinic, P1	Z = 4
a = 9.4779 (4) Å	Mo Kα radiation
b = 11.4478 (5) Å	µ = 0.08 mm⁻¹
c = 13.1117 (7) Å	T = 293 K
α = 95.155 (4)°	0.3 × 0.2 × 0.2 mm
β = 104.118 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5344 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	3273 reflections with I > 2σ(I)
T_min = 0.935, T_max = 1.000	R_int = 0.028
13503 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	38 restraints
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.32 e Å⁻³
5344 reflections	Δρ_min = −0.18 e Å⁻³
385 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.3964 (2)	0.38234 (18)	0.58381 (17)	0.0676 (5)
H1A	0.415 (3)	0.456 (2)	0.5625 (19)	0.080 (8)*
C2A	0.4091 (2)	0.27769 (18)	0.52819 (17)	0.0570 (6)
C3A	0.3733 (3)	0.1891 (2)	0.58493 (19)	0.0701 (6)
H3A	0.3731	0.1086	0.5669	0.084*
C4A	0.3373 (3)	0.2415 (2)	0.6740 (2)	0.0853 (8)
H4A	0.3086	0.2028	0.7262	0.102*
C5A	0.3522 (3)	0.3598 (3)	0.6703 (2)	0.0838 (8)
H5A	0.3344	0.4163	0.7200	0.101*
C6A	0.4623 (2)	0.27838 (17)	0.43447 (16)	0.0533 (5)
O7A	0.51771 (17)	0.37123 (12)	0.41197 (12)	0.0678 (4)
C8A	0.4488 (2)	0.16796 (16)	0.36334 (15)	0.0505 (5)
C9A	0.3340 (2)	0.08001 (17)	0.34810 (16)	0.0549 (5)
H9A	0.2654	0.0873	0.3877	0.066*
C10A	0.3189 (2)	−0.01866 (18)	0.27531 (17)	0.0592 (6)
H10A	0.2407	−0.0765	0.2658	0.071*
C11A	0.4209 (3)	−0.03003 (17)	0.21720 (17)	0.0589 (6)
C12A	0.5375 (3)	0.05661 (18)	0.23217 (18)	0.0626 (6)
H12A	0.6070	0.0485	0.1935	0.075*
C13A	0.5504 (2)	0.15421 (17)	0.30394 (17)	0.0579 (6)
H13A	0.6285	0.2121	0.3129	0.069*
O14A	0.4161 (2)	−0.12257 (13)	0.14272 (13)	0.0798 (5)
C15A	0.3187 (7)	−0.2278 (4)	0.1406 (5)	0.0747 (17)	0.701 (7)
H15A	0.2176	−0.2116	0.1176	0.090*	0.701 (7)
H15B	0.3347	−0.2530	0.2108	0.090*	0.701 (7)
C16A	0.3504 (6)	−0.3227 (3)	0.0649 (3)	0.0749 (14)	0.701 (7)
H161	0.4519	−0.3373	0.0894	0.090*	0.701 (7)
H162	0.2902	−0.3948	0.0664	0.090*	0.701 (7)
C17A	0.3236 (6)	−0.2945 (4)	−0.0474 (3)	0.0872 (15)	0.701 (7)
H171	0.3879	−0.2250	−0.0499	0.105*	0.701 (7)
H172	0.2236	−0.2761	−0.0711	0.105*	0.701 (7)
C18A	0.3490 (11)	−0.3948 (5)	−0.1226 (5)	0.0885 (19)	0.701 (7)
H181	0.4461	−0.4167	−0.0973	0.133*	0.701 (7)
H182	0.3381	−0.3698	−0.1918	0.133*	0.701 (7)
H183	0.2789	−0.4614	−0.1261	0.133*	0.701 (7)
C15C	0.2747 (12)	−0.1933 (10)	0.1086 (9)	0.072 (4)	0.299 (7)
H15C	0.1977	−0.1416	0.0956	0.086*	0.299 (7)
H15D	0.2610	−0.2397	0.1645	0.086*	0.299 (7)
C16C	0.2635 (10)	−0.2746 (8)	0.0093 (9)	0.081 (3)	0.299 (7)
H163	0.1744	−0.3280	−0.0049	0.097*	0.299 (7)
H164	0.2563	−0.2280	−0.0497	0.097*	0.299 (7)
C17C	0.3914 (12)	−0.3461 (10)	0.0157 (9)	0.095 (4)	0.299 (7)
H173	0.3998	−0.3924	0.0749	0.114*	0.299 (7)
H174	0.4807	−0.2932	0.0284	0.114*	0.299 (7)
C18C	0.375 (3)	−0.4285 (15)	−0.0856 (10)	0.093 (5)	0.299 (7)
H184	0.2962	−0.4895	−0.0920	0.139*	0.299 (7)
H185	0.4639	−0.4633	−0.0832	0.139*	0.299 (7)
H186	0.3528	−0.3845	−0.1455	0.139*	0.299 (7)
N1B	0.0500 (2)	0.87463 (18)	0.59698 (16)	0.0639 (5)
H1B	0.042 (3)	0.947 (2)	0.5801 (18)	0.075 (8)*
C2B	0.0550 (2)	0.78032 (17)	0.52617 (17)	0.0567 (5)
C3B	0.0572 (3)	0.6824 (2)	0.5801 (2)	0.0712 (7)
H3B	0.0602	0.6053	0.5523	0.085*
C4B	0.0540 (3)	0.7193 (2)	0.6838 (2)	0.0781 (7)
H4B	0.0546	0.6717	0.7377	0.094*
C5B	0.0497 (3)	0.8383 (2)	0.6909 (2)	0.0716 (7)
H5B	0.0469	0.8864	0.7513	0.086*
C6B	0.0488 (2)	0.79522 (18)	0.41681 (18)	0.0586 (6)
O7B	0.01924 (19)	0.88961 (13)	0.38164 (12)	0.0746 (5)
C8B	0.0762 (2)	0.69620 (17)	0.34547 (17)	0.0553 (5)
C9B	0.1814 (2)	0.62104 (18)	0.37939 (17)	0.0618 (6)
H9B	0.2352	0.6310	0.4497	0.074*
C10B	0.2078 (2)	0.53160 (18)	0.31047 (18)	0.0627 (6)
H10B	0.2805	0.4833	0.3343	0.075*
C11B	0.1270 (2)	0.51385 (17)	0.20688 (17)	0.0547 (5)
C12B	0.0225 (2)	0.58900 (18)	0.17103 (17)	0.0587 (6)
H12B	−0.0316	0.5784	0.1008	0.070*
C13B	−0.0008 (2)	0.67900 (18)	0.23941 (17)	0.0596 (6)
H13B	−0.0698	0.7298	0.2143	0.072*
O14B	0.14249 (17)	0.42661 (12)	0.13369 (12)	0.0673 (4)
C15B	0.2520 (3)	0.3485 (2)	0.1675 (2)	0.0840 (8)
H15E	0.2263	0.3027	0.2204	0.101*	0.869 (4)
H15F	0.3461	0.3939	0.1988	0.101*	0.869 (4)
H15G	0.2512	0.3191	0.2345	0.101*	0.131 (4)
H15H	0.3497	0.3793	0.1658	0.101*	0.131 (4)
C16B	0.2609 (4)	0.2670 (3)	0.0721 (3)	0.0886 (11)	0.869 (4)
H165	0.2643	0.3134	0.0142	0.106*	0.869 (4)
H166	0.3511	0.2302	0.0894	0.106*	0.869 (4)
C17B	0.1392 (5)	0.1761 (3)	0.0378 (3)	0.1069 (13)	0.869 (4)
H175	0.0510	0.2122	0.0093	0.128*	0.869 (4)
H176	0.1257	0.1384	0.0986	0.128*	0.869 (4)
C18B	0.1608 (6)	0.0812 (5)	−0.0471 (3)	0.127 (2)	0.869 (4)
H18A	0.1743	0.1178	−0.1075	0.191*	0.869 (4)
H18B	0.0760	0.0242	−0.0681	0.191*	0.869 (4)
H18C	0.2454	0.0425	−0.0183	0.191*	0.869 (4)
C16D	0.188 (2)	0.2305 (13)	0.1055 (19)	0.0886 (11)	0.131 (4)
H16A	0.1455	0.1854	0.1521	0.106*	0.131 (4)
H16B	0.1069	0.2457	0.0485	0.106*	0.131 (4)
C17D	0.278 (3)	0.151 (2)	0.0574 (17)	0.1069 (13)	0.131 (4)
H17A	0.2925	0.0863	0.1002	0.128*	0.131 (4)
H17B	0.3732	0.1952	0.0680	0.128*	0.131 (4)
C18D	0.234 (5)	0.097 (4)	−0.057 (2)	0.127 (2)	0.131 (4)
H18D	0.1298	0.0778	−0.0793	0.191*	0.131 (4)
H18E	0.2808	0.0261	−0.0639	0.191*	0.131 (4)
H18F	0.2637	0.1518	−0.1011	0.191*	0.131 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0743 (14)	0.0553 (12)	0.0701 (13)	0.0051 (10)	0.0195 (10)	−0.0120 (10)
C2A	0.0581 (13)	0.0514 (12)	0.0563 (13)	0.0084 (10)	0.0085 (10)	−0.0072 (10)
C3A	0.0808 (17)	0.0638 (14)	0.0656 (15)	0.0095 (12)	0.0203 (13)	0.0002 (12)
C4A	0.102 (2)	0.0872 (19)	0.0708 (17)	0.0053 (16)	0.0345 (15)	0.0026 (14)
C5A	0.091 (2)	0.088 (2)	0.0722 (17)	0.0070 (15)	0.0302 (15)	−0.0166 (14)
C6A	0.0511 (13)	0.0462 (12)	0.0567 (13)	0.0074 (10)	0.0042 (10)	−0.0018 (10)
O7A	0.0819 (11)	0.0456 (8)	0.0726 (10)	0.0007 (8)	0.0189 (9)	−0.0024 (7)
C8A	0.0514 (12)	0.0452 (11)	0.0526 (12)	0.0069 (9)	0.0101 (10)	−0.0001 (9)
C9A	0.0508 (13)	0.0577 (12)	0.0553 (13)	0.0039 (10)	0.0163 (10)	−0.0052 (10)
C10A	0.0570 (13)	0.0547 (12)	0.0625 (13)	−0.0083 (10)	0.0182 (11)	−0.0076 (10)
C11A	0.0721 (15)	0.0468 (12)	0.0590 (13)	−0.0006 (10)	0.0257 (11)	−0.0079 (10)
C12A	0.0665 (15)	0.0541 (13)	0.0724 (15)	−0.0009 (11)	0.0339 (12)	−0.0047 (11)
C13A	0.0559 (13)	0.0463 (11)	0.0692 (14)	−0.0043 (9)	0.0176 (11)	−0.0014 (10)
O14A	0.0978 (13)	0.0611 (10)	0.0833 (12)	−0.0177 (9)	0.0482 (10)	−0.0234 (8)
C15A	0.104 (4)	0.046 (3)	0.077 (3)	−0.018 (2)	0.041 (3)	−0.009 (2)
C16A	0.097 (4)	0.056 (2)	0.075 (3)	−0.011 (2)	0.038 (3)	−0.003 (2)
C17A	0.102 (3)	0.088 (3)	0.072 (3)	0.014 (3)	0.029 (3)	−0.011 (2)
C18A	0.117 (5)	0.079 (4)	0.072 (4)	0.006 (3)	0.038 (4)	−0.013 (3)
C15C	0.106 (9)	0.036 (6)	0.073 (8)	−0.012 (5)	0.035 (6)	−0.015 (5)
C16C	0.085 (7)	0.076 (6)	0.079 (8)	0.002 (5)	0.023 (6)	−0.006 (5)
C17C	0.126 (10)	0.104 (8)	0.068 (8)	0.015 (7)	0.049 (7)	0.015 (6)
C18C	0.118 (10)	0.093 (9)	0.076 (9)	0.020 (8)	0.042 (8)	−0.006 (7)
N1B	0.0719 (13)	0.0550 (12)	0.0665 (13)	0.0095 (10)	0.0214 (10)	0.0025 (10)
C2B	0.0596 (14)	0.0480 (12)	0.0604 (14)	0.0006 (10)	0.0154 (11)	−0.0021 (10)
C3B	0.0794 (17)	0.0531 (13)	0.0778 (17)	−0.0040 (11)	0.0190 (13)	0.0020 (12)
C4B	0.0880 (19)	0.0750 (17)	0.0723 (17)	−0.0023 (13)	0.0222 (14)	0.0169 (13)
C5B	0.0720 (17)	0.0831 (18)	0.0608 (15)	0.0056 (13)	0.0219 (12)	0.0027 (13)
C6B	0.0597 (14)	0.0490 (12)	0.0670 (15)	0.0033 (10)	0.0187 (11)	0.0004 (11)
O7B	0.1014 (13)	0.0535 (9)	0.0751 (11)	0.0211 (8)	0.0294 (9)	0.0081 (8)
C8B	0.0596 (13)	0.0458 (11)	0.0596 (13)	0.0052 (10)	0.0153 (11)	0.0017 (10)
C9B	0.0634 (14)	0.0563 (13)	0.0582 (13)	0.0077 (11)	0.0037 (11)	−0.0025 (10)
C10B	0.0622 (14)	0.0540 (13)	0.0683 (15)	0.0132 (11)	0.0089 (12)	0.0030 (11)
C11B	0.0573 (13)	0.0459 (11)	0.0601 (13)	0.0017 (10)	0.0171 (11)	−0.0011 (10)
C12B	0.0609 (14)	0.0594 (13)	0.0549 (13)	0.0080 (11)	0.0127 (11)	0.0053 (10)
C13B	0.0619 (14)	0.0583 (13)	0.0608 (14)	0.0153 (10)	0.0155 (11)	0.0110 (11)
O14B	0.0763 (11)	0.0571 (9)	0.0655 (10)	0.0110 (8)	0.0159 (8)	−0.0061 (7)
C15B	0.0922 (19)	0.0690 (16)	0.0907 (19)	0.0299 (14)	0.0213 (15)	−0.0065 (14)
C16B	0.103 (3)	0.071 (2)	0.101 (3)	0.0203 (19)	0.042 (2)	0.0037 (17)
C17B	0.142 (4)	0.082 (2)	0.089 (3)	0.009 (2)	0.023 (2)	−0.0127 (19)
C18B	0.209 (6)	0.080 (3)	0.090 (2)	0.008 (3)	0.045 (3)	−0.016 (2)
C16D	0.103 (3)	0.071 (2)	0.101 (3)	0.0203 (19)	0.042 (2)	0.0037 (17)
C17D	0.142 (4)	0.082 (2)	0.089 (3)	0.009 (2)	0.023 (2)	−0.0127 (19)
C18D	0.209 (6)	0.080 (3)	0.090 (2)	0.008 (3)	0.045 (3)	−0.016 (2)

Geometric parameters (Å, º) top

N1A—C5A	1.340 (3)	N1B—C5B	1.335 (3)
N1A—C2A	1.375 (3)	N1B—C2B	1.371 (3)
N1A—H1A	0.92 (2)	N1B—H1B	0.88 (2)
C2A—C3A	1.379 (3)	C2B—C3B	1.377 (3)
C2A—C6A	1.438 (3)	C2B—C6B	1.447 (3)
C3A—C4A	1.394 (3)	C3B—C4B	1.395 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.356 (4)	C4B—C5B	1.362 (3)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—O7A	1.239 (2)	C6B—O7B	1.239 (2)
C6A—C8A	1.479 (3)	C6B—C8B	1.484 (3)
C8A—C9A	1.385 (3)	C8B—C9B	1.387 (3)
C8A—C13A	1.388 (3)	C8B—C13B	1.392 (3)
C9A—C10A	1.386 (3)	C9B—C10B	1.383 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.376 (3)	C10B—C11B	1.375 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—O14A	1.365 (2)	C11B—O14B	1.364 (2)
C11A—C12A	1.388 (3)	C11B—C12B	1.387 (3)
C12A—C13A	1.372 (3)	C12B—C13B	1.372 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—H13A	0.9300	C13B—H13B	0.9300
O14A—C15A	1.451 (5)	O14B—C15B	1.439 (3)
O14A—C15C	1.456 (9)	C15B—C16D	1.512 (10)
C15A—C16A	1.503 (6)	C15B—C16B	1.515 (3)
C15A—H15A	0.9700	C15B—H15E	0.9700
C15A—H15B	0.9700	C15B—H15F	0.9700
C16A—C17A	1.501 (5)	C15B—H15G	0.9700
C16A—H161	0.9700	C15B—H15H	0.9700
C16A—H162	0.9700	C16B—C17B	1.444 (5)
C17A—C18A	1.518 (6)	C16B—H165	0.9700
C17A—H171	0.9700	C16B—H166	0.9700
C17A—H172	0.9700	C17B—C18B	1.546 (5)
C18A—H181	0.9600	C17B—H175	0.9700
C18A—H182	0.9600	C17B—H176	0.9700
C18A—H183	0.9600	C18B—H18A	0.9600
C15C—C16C	1.507 (9)	C18B—H18B	0.9600
C15C—H15C	0.9700	C18B—H18C	0.9600
C15C—H15D	0.9700	C16D—C17D	1.496 (10)
C16C—C17C	1.506 (9)	C16D—H16A	0.9700
C16C—H163	0.9700	C16D—H16B	0.9700
C16C—H164	0.9700	C17D—C18D	1.519 (10)
C17C—C18C	1.525 (9)	C17D—H17A	0.9700
C17C—H173	0.9700	C17D—H17B	0.9700
C17C—H174	0.9700	C18D—H18D	0.9600
C18C—H184	0.9600	C18D—H18E	0.9600
C18C—H185	0.9600	C18D—H18F	0.9600
C18C—H186	0.9600

C5A—N1A—C2A	109.3 (2)	C17C—C18C—H186	109.5
C5A—N1A—H1A	126.9 (15)	H184—C18C—H186	109.5
C2A—N1A—H1A	123.8 (15)	H185—C18C—H186	109.5
N1A—C2A—C3A	106.6 (2)	C5B—N1B—C2B	109.9 (2)
N1A—C2A—C6A	120.1 (2)	C5B—N1B—H1B	126.4 (15)
C3A—C2A—C6A	133.22 (19)	C2B—N1B—H1B	123.6 (15)
C2A—C3A—C4A	107.9 (2)	N1B—C2B—C3B	106.4 (2)
C2A—C3A—H3A	126.1	N1B—C2B—C6B	120.85 (18)
C4A—C3A—H3A	126.1	C3B—C2B—C6B	132.7 (2)
C5A—C4A—C3A	107.1 (2)	C2B—C3B—C4B	108.0 (2)
C5A—C4A—H4A	126.5	C2B—C3B—H3B	126.0
C3A—C4A—H4A	126.5	C4B—C3B—H3B	126.0
N1A—C5A—C4A	109.2 (2)	C5B—C4B—C3B	106.9 (2)
N1A—C5A—H5A	125.4	C5B—C4B—H4B	126.5
C4A—C5A—H5A	125.4	C3B—C4B—H4B	126.5
O7A—C6A—C2A	120.48 (18)	N1B—C5B—C4B	108.8 (2)
O7A—C6A—C8A	119.59 (19)	N1B—C5B—H5B	125.6
C2A—C6A—C8A	119.92 (19)	C4B—C5B—H5B	125.6
C9A—C8A—C13A	117.99 (18)	O7B—C6B—C2B	120.60 (19)
C9A—C8A—C6A	122.99 (18)	O7B—C6B—C8B	119.5 (2)
C13A—C8A—C6A	118.90 (19)	C2B—C6B—C8B	119.88 (18)
C8A—C9A—C10A	121.60 (19)	C9B—C8B—C13B	117.58 (19)
C8A—C9A—H9A	119.2	C9B—C8B—C6B	122.3 (2)
C10A—C9A—H9A	119.2	C13B—C8B—C6B	120.08 (18)
C11A—C10A—C9A	119.27 (19)	C10B—C9B—C8B	121.1 (2)
C11A—C10A—H10A	120.4	C10B—C9B—H9B	119.4
C9A—C10A—H10A	120.4	C8B—C9B—H9B	119.4
O14A—C11A—C10A	124.27 (19)	C11B—C10B—C9B	120.23 (19)
O14A—C11A—C12A	115.79 (18)	C11B—C10B—H10B	119.9
C10A—C11A—C12A	119.94 (19)	C9B—C10B—H10B	119.9
C13A—C12A—C11A	120.14 (19)	O14B—C11B—C10B	124.59 (18)
C13A—C12A—H12A	119.9	O14B—C11B—C12B	115.90 (19)
C11A—C12A—H12A	119.9	C10B—C11B—C12B	119.50 (19)
C12A—C13A—C8A	121.06 (19)	C13B—C12B—C11B	119.8 (2)
C12A—C13A—H13A	119.5	C13B—C12B—H12B	120.1
C8A—C13A—H13A	119.5	C11B—C12B—H12B	120.1
C11A—O14A—C15A	118.1 (3)	C12B—C13B—C8B	121.65 (19)
C11A—O14A—C15C	113.8 (5)	C12B—C13B—H13B	119.2
O14A—C15A—C16A	108.0 (4)	C8B—C13B—H13B	119.2
O14A—C15A—H15A	110.1	C11B—O14B—C15B	117.42 (17)
C16A—C15A—H15A	110.1	O14B—C15B—C16D	104.5 (9)
O14A—C15A—H15B	110.1	O14B—C15B—C16B	108.6 (2)
C16A—C15A—H15B	110.1	O14B—C15B—H15E	110.0
H15A—C15A—H15B	108.4	C16B—C15B—H15E	110.0
C17A—C16A—C15A	114.5 (5)	O14B—C15B—H15F	110.0
C17A—C16A—H161	108.6	C16B—C15B—H15F	110.0
C15A—C16A—H161	108.6	H15E—C15B—H15F	108.4
C17A—C16A—H162	108.6	O14B—C15B—H15G	114.2
C15A—C16A—H162	108.6	C16B—C15B—H15G	121.5
H161—C16A—H162	107.6	O14B—C15B—H15H	113.8
C16A—C17A—C18A	113.1 (5)	C16D—C15B—H15H	118.5
C16A—C17A—H171	109.0	H15E—C15B—H15H	126.6
C18A—C17A—H171	109.0	H15G—C15B—H15H	111.7
C16A—C17A—H172	109.0	C17B—C16B—C15B	113.1 (3)
C18A—C17A—H172	109.0	C17B—C16B—H165	109.0
H171—C17A—H172	107.8	C15B—C16B—H165	109.0
O14A—C15C—C16C	111.5 (8)	C17B—C16B—H166	109.0
O14A—C15C—H15C	109.3	C15B—C16B—H166	109.0
C16C—C15C—H15C	109.3	H165—C16B—H166	107.8
O14A—C15C—H15D	109.3	C16B—C17B—C18B	113.0 (3)
C16C—C15C—H15D	109.3	C16B—C17B—H175	109.0
H15C—C15C—H15D	108.0	C18B—C17B—H175	109.0
C17C—C16C—C15C	113.5 (10)	C16B—C17B—H176	109.0
C17C—C16C—H163	108.9	C18B—C17B—H176	109.0
C15C—C16C—H163	108.9	H175—C17B—H176	107.8
C17C—C16C—H164	108.9	C17D—C16D—C15B	122.0 (15)
C15C—C16C—H164	108.9	C17D—C16D—H16A	106.8
H163—C16C—H164	107.7	C15B—C16D—H16A	106.8
C16C—C17C—C18C	111.8 (12)	C17D—C16D—H16B	106.8
C16C—C17C—H173	109.2	C15B—C16D—H16B	106.8
C18C—C17C—H173	109.2	H16A—C16D—H16B	106.7
C16C—C17C—H174	109.2	C16D—C17D—C18D	124 (3)
C18C—C17C—H174	109.3	C16D—C17D—H17A	106.4
H173—C17C—H174	107.9	C18D—C17D—H17A	106.4
C17C—C18C—H184	109.5	C16D—C17D—H17B	106.4
C17C—C18C—H185	109.5	C18D—C17D—H17B	106.4
H184—C18C—H185	109.5	H17A—C17D—H17B	106.5

C5A—N1A—C2A—C3A	−1.0 (3)	C15C—C16C—C17C—C18C	179.1 (11)
C5A—N1A—C2A—C6A	−176.9 (2)	C5B—N1B—C2B—C3B	0.2 (3)
N1A—C2A—C3A—C4A	0.7 (3)	C5B—N1B—C2B—C6B	176.8 (2)
C6A—C2A—C3A—C4A	175.8 (2)	N1B—C2B—C3B—C4B	−0.2 (3)
C2A—C3A—C4A—C5A	−0.2 (3)	C6B—C2B—C3B—C4B	−176.2 (2)
C2A—N1A—C5A—C4A	0.9 (3)	C2B—C3B—C4B—C5B	0.1 (3)
C3A—C4A—C5A—N1A	−0.4 (3)	C2B—N1B—C5B—C4B	−0.2 (3)
N1A—C2A—C6A—O7A	11.1 (3)	C3B—C4B—C5B—N1B	0.0 (3)
C3A—C2A—C6A—O7A	−163.5 (2)	N1B—C2B—C6B—O7B	−9.8 (3)
N1A—C2A—C6A—C8A	−168.00 (18)	C3B—C2B—C6B—O7B	165.7 (2)
C3A—C2A—C6A—C8A	17.5 (4)	N1B—C2B—C6B—C8B	171.02 (18)
O7A—C6A—C8A—C9A	−146.7 (2)	C3B—C2B—C6B—C8B	−13.4 (4)
C2A—C6A—C8A—C9A	32.4 (3)	O7B—C6B—C8B—C9B	142.7 (2)
O7A—C6A—C8A—C13A	29.2 (3)	C2B—C6B—C8B—C9B	−38.1 (3)
C2A—C6A—C8A—C13A	−151.68 (19)	O7B—C6B—C8B—C13B	−34.7 (3)
C13A—C8A—C9A—C10A	−0.6 (3)	C2B—C6B—C8B—C13B	144.5 (2)
C6A—C8A—C9A—C10A	175.36 (19)	C13B—C8B—C9B—C10B	−0.6 (3)
C8A—C9A—C10A—C11A	0.4 (3)	C6B—C8B—C9B—C10B	−178.0 (2)
C9A—C10A—C11A—O14A	−179.3 (2)	C8B—C9B—C10B—C11B	−1.6 (3)
C9A—C10A—C11A—C12A	0.2 (3)	C9B—C10B—C11B—O14B	−178.45 (19)
O14A—C11A—C12A—C13A	178.81 (19)	C9B—C10B—C11B—C12B	2.4 (3)
C10A—C11A—C12A—C13A	−0.7 (3)	O14B—C11B—C12B—C13B	179.75 (18)
C11A—C12A—C13A—C8A	0.5 (3)	C10B—C11B—C12B—C13B	−1.0 (3)
C9A—C8A—C13A—C12A	0.1 (3)	C11B—C12B—C13B—C8B	−1.2 (3)
C6A—C8A—C13A—C12A	−176.02 (19)	C9B—C8B—C13B—C12B	2.0 (3)
C10A—C11A—O14A—C15A	−14.7 (4)	C6B—C8B—C13B—C12B	179.5 (2)
C12A—C11A—O14A—C15A	165.8 (4)	C10B—C11B—O14B—C15B	−0.5 (3)
C10A—C11A—O14A—C15C	15.6 (6)	C12B—C11B—O14B—C15B	178.7 (2)
C12A—C11A—O14A—C15C	−163.9 (6)	C11B—O14B—C15B—C16D	145.8 (10)
C11A—O14A—C15A—C16A	−171.0 (3)	C11B—O14B—C15B—C16B	−174.4 (2)
C15C—O14A—C15A—C16A	101.0 (15)	O14B—C15B—C16B—C17B	−74.7 (3)
O14A—C15A—C16A—C17A	−62.0 (7)	C16D—C15B—C16B—C17B	15.3 (15)
C15A—C16A—C17A—C18A	−177.0 (5)	C15B—C16B—C17B—C18B	−170.5 (3)
C11A—O14A—C15C—C16C	166.2 (7)	O14B—C15B—C16D—C17D	139 (2)
C15A—O14A—C15C—C16C	−88.3 (16)	C16B—C15B—C16D—C17D	36.7 (15)
O14A—C15C—C16C—C17C	50.3 (14)	C15B—C16D—C17D—C18D	−130 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O7Aⁱ	0.93 (3)	2.00 (2)	2.864 (2)	154 (2)
N1B—H1B···O7Bⁱⁱ	0.88 (3)	2.06 (2)	2.834 (3)	146 (2)
C9B—H9B···O7Aⁱ	0.93	2.59	3.426 (3)	149

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO₂
M_r	243.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4779 (4), 11.4478 (5), 13.1117 (7)
α, β, γ (°)	95.155 (4), 104.118 (4), 94.626 (3)
V (Å³)	1366.31 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.935, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13503, 5344, 3273
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.160, 1.03
No. of reflections	5344
No. of parameters	385
No. of restraints	38
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O7Aⁱ	0.93 (3)	2.00 (2)	2.864 (2)	154 (2)
N1B—H1B···O7Bⁱⁱ	0.88 (3)	2.06 (2)	2.834 (3)	146 (2)
C9B—H9B···O7Aⁱ	0.93	2.59	3.426 (3)	149

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1.

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

English, R. B., McGillivray, G. & Smal, E. (1980). Acta Cryst. B36, 1136–1141. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fischer, H. & Orth, H. (1934). Die Chemie des Pyrrols, Vol. 1, p. 333. Leipzig: Akademische Verlagsgesellschaft. Google Scholar
Mohamed, M. S., EL-Domany, R. A. & EL-Hameed, R. H. A. (2009). Acta Pharm. 59, 145–158. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar