Ethyl 2-phenyl-5,6-dihydro­pyrrolo­[2,1-a]isoquinoline-3-carboxyl­ate

Yu, Z.-P.; Zhao, M.; Feng, C.-T.

doi:10.1107/S1600536812024853

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2021

https://doi.org/10.1107/S1600536812024853

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Ethyl 2-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate

Zhao-Peng Yu,^a ^* Ming Zhao ^b and Cheng-Tao Feng ^c

^aSchool of Chemistry and Chemical Engineering, Linyi University, Linyi, Shandong 276005, People's Republic of China, ^bDepartment of Chemistry, Huainan Union University, Huainan 232038, People's Republic of China, and ^cDepartment of Chemistry, University of Science and Technology of China, 230026 Hefei, People's Republic of China
^*Correspondence e-mail: yuzp@mail.ustc.edu.cn

(Received 28 May 2012; accepted 31 May 2012; online 13 June 2012)

In the title compound, C₂₁H₁₉NO₂, the six-membered heterocycle assumes a screw-boat conformation. The phenyl ring is oriented with respect to the pyrrole ring at a dihedral angle of 64.76 (10)°. An intramolecular C—H⋯O hydrogen bond helps to stabilize the molecular structure. There are weak C—H⋯π interactions between inversion-related molecules in the crystal.

Related literature

For background and applications of lamellarins, see: Bailly (2004 ); Zou et al. (2011 ). For a related compound, see: Feng et al. (2012 ).

Experimental

Crystal data

C₂₁H₁₉NO₂
M_r = 317.37
Triclinic, $[P \overline 1]$
a = 8.1527 (6) Å
b = 8.4029 (6) Å
c = 12.4220 (8) Å
α = 100.117 (6)°
β = 101.155 (5)°
γ = 94.312 (6)°
V = 816.66 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 K
0.42 × 0.37 × 0.32 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
6799 measured reflections
3340 independent reflections
2233 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.117
S = 1.02
3340 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyrrole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1	0.97	2.29	2.913 (2)	121
C8—H8B⋯Cg1ⁱ	0.97	2.69	3.6411 (19)	166
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024853/xu5552sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024853/xu5552Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024853/xu5552Isup3.cml

checkCIF report

Comment top

Lamellarin alkaloids, a new family of marine natural products that contain a pyrrolo[2,1-a]isoquinoline core, were found to exhibit a wide spectrum of biological activities (Bailly, 2004). Natural as well as synthetic lamellarins should be excellent candidates for the development of new drugs due to their unique skeletal structure and their important biological activities especially as antitumor agents (Zou et al., 2011). As part of our previous studies concerning anticancer agents, we here report a crystal structure of open chain analogues of lamellarins (Feng et al., 2012).

The conformational analysis show that the conformation of 6-membered hetero-ring is screw boat. The phenyl ring is oriented with respect to the pyrrole ring at 64.76 (10)°. An intramolecular C—H···O hydrogen bond helps to stabilize the molecular structure. There is weak C—H···π interaction between inversion-related molecules in the crystal.

Related literature top

For background and applications of lamellarins, see: Bailly (2004); Zou et al. (2011). For a related compound, see: Feng et al. (2012).

Experimental top

Synthesis or separation ??

Colourless blocky single crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow evaporation of the mixed solvent ethanol/CH₂Cl₂ (2:1, v/v) at room temperature for five days.

Structure description top

For background and applications of lamellarins, see: Bailly (2004); Zou et al. (2011). For a related compound, see: Feng et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 45% probability level.

Ethyl 2-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate top

Crystal data top

C₂₁H₁₉NO₂	Z = 2
M_r = 317.37	F(000) = 336
Triclinic, P1	D_x = 1.291 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1527 (6) Å	Cell parameters from 1649 reflections
b = 8.4029 (6) Å	θ = 3.3–29.0°
c = 12.4220 (8) Å	µ = 0.08 mm⁻¹
α = 100.117 (6)°	T = 291 K
β = 101.155 (5)°	Block, colourless
γ = 94.312 (6)°	0.42 × 0.37 × 0.32 mm
V = 816.66 (10) Å³

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2233 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.027
Graphite monochromator	θ_max = 26.4°, θ_min = 3.3°
Detector resolution: 15.9149 pixels mm^-1	h = −9→10
ω scans	k = −10→10
6799 measured reflections	l = −15→15
3340 independent reflections

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0468P)² + 0.0731P] where P = (F_o² + 2F_c²)/3
3340 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₁₉NO₂	γ = 94.312 (6)°
M_r = 317.37	V = 816.66 (10) Å³
Triclinic, P1	Z = 2
a = 8.1527 (6) Å	Mo Kα radiation
b = 8.4029 (6) Å	µ = 0.08 mm⁻¹
c = 12.4220 (8) Å	T = 291 K
α = 100.117 (6)°	0.42 × 0.37 × 0.32 mm
β = 101.155 (5)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2233 reflections with I > 2σ(I)
6799 measured reflections	R_int = 0.027
3340 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	Δρ_max = 0.14 e Å⁻³
3340 reflections	Δρ_min = −0.18 e Å⁻³
218 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.42666 (15)	0.27334 (17)	0.95299 (10)	0.0434 (4)
O1	0.77604 (15)	0.2297 (2)	1.03663 (11)	0.0740 (5)
O2	0.69802 (14)	0.16479 (18)	1.18676 (10)	0.0631 (4)
C5	0.1606 (2)	0.3304 (2)	0.84460 (13)	0.0443 (4)
C18	0.2738 (2)	0.0419 (2)	1.23460 (15)	0.0539 (5)
H18	0.2135	−0.0303	1.1714	0.065*
C8	0.5153 (2)	0.3175 (2)	0.86845 (13)	0.0505 (5)
H8A	0.6167	0.2637	0.8705	0.061*
H8B	0.5475	0.4341	0.8840	0.061*
C12	0.49185 (19)	0.2354 (2)	1.05503 (13)	0.0434 (4)
C13	0.3623 (2)	0.1813 (2)	1.22237 (13)	0.0454 (4)
C10	0.2142 (2)	0.2488 (2)	1.03899 (13)	0.0480 (4)
H10	0.1065	0.2455	1.0537	0.058*
C11	0.3589 (2)	0.2190 (2)	1.10987 (13)	0.0447 (4)
C6	0.0014 (2)	0.3795 (2)	0.84292 (14)	0.0536 (5)
H6	−0.0453	0.3829	0.9058	0.064*
C1	−0.0877 (2)	0.4233 (2)	0.74877 (15)	0.0600 (5)
H1	−0.1942	0.4563	0.7482	0.072*
C9	0.25855 (19)	0.2840 (2)	0.94354 (13)	0.0439 (4)
C17	0.2729 (3)	0.0075 (3)	1.33909 (17)	0.0671 (6)
H17	0.2136	−0.0879	1.3458	0.080*
C4	0.2309 (2)	0.3253 (2)	0.74989 (13)	0.0488 (4)
C20	0.8689 (2)	0.1447 (3)	1.23534 (15)	0.0621 (5)
H20B	0.9460	0.2307	1.2238	0.075*
H20A	0.8983	0.0409	1.2010	0.075*
C16	0.3596 (3)	0.1139 (3)	1.43305 (17)	0.0696 (6)
H16	0.3590	0.0908	1.5035	0.084*
C14	0.4485 (2)	0.2875 (3)	1.31825 (15)	0.0610 (5)
H14	0.5085	0.3829	1.3120	0.073*
C15	0.4469 (3)	0.2539 (3)	1.42279 (15)	0.0708 (6)
H15	0.5052	0.3266	1.4864	0.085*
C7	0.4011 (2)	0.2665 (2)	0.75443 (13)	0.0556 (5)
H7A	0.4538	0.3089	0.7001	0.067*
H7B	0.3873	0.1487	0.7338	0.067*
C19	0.6685 (2)	0.2107 (2)	1.08874 (14)	0.0474 (4)
C3	0.1386 (2)	0.3693 (2)	0.65604 (15)	0.0610 (5)
H3	0.1837	0.3658	0.5925	0.073*
C2	−0.0192 (3)	0.4181 (3)	0.65534 (16)	0.0646 (5)
H2	−0.0796	0.4476	0.5917	0.077*
C21	0.8791 (3)	0.1518 (3)	1.35720 (17)	0.0809 (7)
H21A	0.8039	0.0649	1.3675	0.121*
H21B	0.8479	0.2543	1.3900	0.121*
H21C	0.9921	0.1408	1.3926	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0427 (7)	0.0525 (9)	0.0368 (8)	0.0057 (6)	0.0130 (6)	0.0080 (6)
O1	0.0462 (7)	0.1197 (14)	0.0634 (9)	0.0135 (8)	0.0206 (6)	0.0257 (8)
O2	0.0443 (7)	0.0917 (11)	0.0587 (8)	0.0135 (7)	0.0087 (6)	0.0292 (7)
C5	0.0485 (9)	0.0444 (11)	0.0373 (9)	0.0012 (8)	0.0068 (7)	0.0047 (7)
C18	0.0594 (11)	0.0530 (12)	0.0541 (11)	0.0124 (9)	0.0195 (9)	0.0124 (9)
C8	0.0518 (10)	0.0596 (12)	0.0454 (10)	0.0072 (9)	0.0218 (8)	0.0115 (9)
C12	0.0434 (9)	0.0488 (11)	0.0396 (9)	0.0073 (8)	0.0117 (7)	0.0090 (8)
C13	0.0432 (9)	0.0564 (12)	0.0411 (10)	0.0138 (8)	0.0133 (7)	0.0130 (8)
C10	0.0416 (9)	0.0614 (12)	0.0429 (10)	0.0067 (8)	0.0130 (7)	0.0107 (8)
C11	0.0452 (9)	0.0502 (11)	0.0405 (9)	0.0077 (8)	0.0122 (7)	0.0094 (8)
C6	0.0510 (10)	0.0624 (13)	0.0461 (10)	0.0072 (9)	0.0094 (8)	0.0080 (9)
C1	0.0551 (11)	0.0656 (14)	0.0553 (11)	0.0085 (9)	0.0009 (9)	0.0125 (10)
C9	0.0432 (9)	0.0487 (11)	0.0395 (9)	0.0042 (8)	0.0108 (7)	0.0057 (8)
C17	0.0864 (14)	0.0631 (14)	0.0653 (14)	0.0175 (11)	0.0318 (11)	0.0274 (11)
C4	0.0575 (10)	0.0492 (11)	0.0375 (9)	0.0010 (8)	0.0090 (8)	0.0057 (8)
C20	0.0442 (10)	0.0721 (15)	0.0652 (13)	0.0141 (9)	0.0003 (9)	0.0098 (10)
C16	0.0869 (15)	0.0860 (17)	0.0510 (12)	0.0336 (13)	0.0261 (11)	0.0304 (12)
C14	0.0657 (12)	0.0681 (14)	0.0482 (11)	−0.0001 (10)	0.0126 (9)	0.0115 (10)
C15	0.0806 (14)	0.0864 (18)	0.0420 (11)	0.0104 (12)	0.0088 (10)	0.0075 (11)
C7	0.0629 (11)	0.0663 (13)	0.0407 (10)	0.0068 (10)	0.0198 (8)	0.0093 (9)
C19	0.0468 (10)	0.0487 (11)	0.0456 (10)	0.0046 (8)	0.0112 (8)	0.0050 (8)
C3	0.0706 (13)	0.0690 (14)	0.0427 (11)	0.0028 (10)	0.0107 (9)	0.0128 (9)
C2	0.0707 (13)	0.0690 (15)	0.0501 (11)	0.0055 (11)	−0.0030 (10)	0.0193 (10)
C21	0.0661 (13)	0.103 (2)	0.0663 (14)	0.0083 (12)	−0.0041 (10)	0.0175 (13)

Geometric parameters (Å, º) top

N1—C9	1.3639 (19)	C6—H6	0.9300
N1—C12	1.3775 (19)	C1—C2	1.377 (3)
N1—C8	1.4675 (18)	C1—H1	0.9300
O1—C19	1.2036 (19)	C17—C16	1.371 (3)
O2—C19	1.325 (2)	C17—H17	0.9300
O2—C20	1.442 (2)	C4—C3	1.384 (2)
C5—C6	1.389 (2)	C4—C7	1.502 (2)
C5—C4	1.401 (2)	C20—C21	1.490 (2)
C5—C9	1.461 (2)	C20—H20B	0.9700
C18—C13	1.376 (2)	C20—H20A	0.9700
C18—C17	1.380 (2)	C16—C15	1.367 (3)
C18—H18	0.9300	C16—H16	0.9300
C8—C7	1.508 (2)	C14—C15	1.379 (2)
C8—H8A	0.9700	C14—H14	0.9300
C8—H8B	0.9700	C15—H15	0.9300
C12—C11	1.398 (2)	C7—H7A	0.9700
C12—C19	1.461 (2)	C7—H7B	0.9700
C13—C14	1.385 (2)	C3—C2	1.379 (3)
C13—C11	1.482 (2)	C3—H3	0.9300
C10—C9	1.377 (2)	C2—H2	0.9300
C10—C11	1.396 (2)	C21—H21A	0.9600
C10—H10	0.9300	C21—H21B	0.9600
C6—C1	1.376 (2)	C21—H21C	0.9600

C9—N1—C12	109.29 (12)	C3—C4—C5	118.70 (17)
C9—N1—C8	121.26 (13)	C3—C4—C7	123.36 (15)
C12—N1—C8	129.05 (13)	C5—C4—C7	117.91 (14)
C19—O2—C20	118.09 (13)	O2—C20—C21	107.19 (15)
C6—C5—C4	119.82 (15)	O2—C20—H20B	110.3
C6—C5—C9	121.65 (14)	C21—C20—H20B	110.3
C4—C5—C9	118.53 (15)	O2—C20—H20A	110.3
C13—C18—C17	121.11 (18)	C21—C20—H20A	110.3
C13—C18—H18	119.4	H20B—C20—H20A	108.5
C17—C18—H18	119.4	C15—C16—C17	119.77 (18)
N1—C8—C7	109.17 (13)	C15—C16—H16	120.1
N1—C8—H8A	109.8	C17—C16—H16	120.1
C7—C8—H8A	109.8	C15—C14—C13	120.98 (19)
N1—C8—H8B	109.8	C15—C14—H14	119.5
C7—C8—H8B	109.8	C13—C14—H14	119.5
H8A—C8—H8B	108.3	C16—C15—C14	120.1 (2)
N1—C12—C11	107.38 (13)	C16—C15—H15	120.0
N1—C12—C19	122.42 (13)	C14—C15—H15	120.0
C11—C12—C19	130.12 (15)	C4—C7—C8	112.81 (14)
C18—C13—C14	117.99 (15)	C4—C7—H7A	109.0
C18—C13—C11	120.63 (16)	C8—C7—H7A	109.0
C14—C13—C11	121.33 (16)	C4—C7—H7B	109.0
C9—C10—C11	108.17 (14)	C8—C7—H7B	109.0
C9—C10—H10	125.9	H7A—C7—H7B	107.8
C11—C10—H10	125.9	O1—C19—O2	123.10 (16)
C10—C11—C12	107.05 (14)	O1—C19—C12	125.80 (16)
C10—C11—C13	124.05 (14)	O2—C19—C12	111.10 (14)
C12—C11—C13	128.89 (14)	C2—C3—C4	121.00 (17)
C1—C6—C5	120.41 (16)	C2—C3—H3	119.5
C1—C6—H6	119.8	C4—C3—H3	119.5
C5—C6—H6	119.8	C1—C2—C3	120.08 (17)
C6—C1—C2	119.99 (18)	C1—C2—H2	120.0
C6—C1—H1	120.0	C3—C2—H2	120.0
C2—C1—H1	120.0	C20—C21—H21A	109.5
N1—C9—C10	108.09 (14)	C20—C21—H21B	109.5
N1—C9—C5	120.21 (13)	H21A—C21—H21B	109.5
C10—C9—C5	131.69 (15)	C20—C21—H21C	109.5
C16—C17—C18	120.0 (2)	H21A—C21—H21C	109.5
C16—C17—H17	120.0	H21B—C21—H21C	109.5
C18—C17—H17	120.0

C9—N1—C8—C7	−36.6 (2)	C4—C5—C9—N1	15.1 (2)
C12—N1—C8—C7	151.50 (17)	C6—C5—C9—C10	13.7 (3)
C9—N1—C12—C11	1.12 (19)	C4—C5—C9—C10	−166.59 (18)
C8—N1—C12—C11	173.80 (16)	C13—C18—C17—C16	0.8 (3)
C9—N1—C12—C19	178.10 (15)	C6—C5—C4—C3	−0.2 (3)
C8—N1—C12—C19	−9.2 (3)	C9—C5—C4—C3	−179.93 (16)
C17—C18—C13—C14	−1.0 (3)	C6—C5—C4—C7	−178.17 (16)
C17—C18—C13—C11	−178.47 (16)	C9—C5—C4—C7	2.1 (2)
C9—C10—C11—C12	−0.5 (2)	C19—O2—C20—C21	160.33 (17)
C9—C10—C11—C13	178.27 (16)	C18—C17—C16—C15	−0.1 (3)
N1—C12—C11—C10	−0.3 (2)	C18—C13—C14—C15	0.5 (3)
C19—C12—C11—C10	−177.02 (18)	C11—C13—C14—C15	177.98 (16)
N1—C12—C11—C13	−179.07 (17)	C17—C16—C15—C14	−0.4 (3)
C19—C12—C11—C13	4.3 (3)	C13—C14—C15—C16	0.2 (3)
C18—C13—C11—C10	63.7 (2)	C3—C4—C7—C8	146.38 (18)
C14—C13—C11—C10	−113.6 (2)	C5—C4—C7—C8	−35.8 (2)
C18—C13—C11—C12	−117.7 (2)	N1—C8—C7—C4	51.0 (2)
C14—C13—C11—C12	64.9 (3)	C20—O2—C19—O1	3.1 (3)
C4—C5—C6—C1	0.0 (3)	C20—O2—C19—C12	−176.31 (15)
C9—C5—C6—C1	179.69 (17)	N1—C12—C19—O1	4.8 (3)
C5—C6—C1—C2	0.1 (3)	C11—C12—C19—O1	−178.94 (18)
C12—N1—C9—C10	−1.46 (19)	N1—C12—C19—O2	−175.75 (15)
C8—N1—C9—C10	−174.81 (15)	C11—C12—C19—O2	0.5 (3)
C12—N1—C9—C5	177.22 (15)	C5—C4—C3—C2	0.3 (3)
C8—N1—C9—C5	3.9 (2)	C7—C4—C3—C2	178.15 (17)
C11—C10—C9—N1	1.2 (2)	C6—C1—C2—C3	0.0 (3)
C11—C10—C9—C5	−177.24 (18)	C4—C3—C2—C1	−0.2 (3)
C6—C5—C9—N1	−164.60 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the pyrrole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.97	2.29	2.913 (2)	121
C8—H8B···Cg1ⁱ	0.97	2.69	3.6411 (19)	166

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉NO₂
M_r	317.37
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.1527 (6), 8.4029 (6), 12.4220 (8)
α, β, γ (°)	100.117 (6), 101.155 (5), 94.312 (6)
V (Å³)	816.66 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.37 × 0.32

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6799, 3340, 2233
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.117, 1.02
No. of reflections	3340
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the pyrrole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.97	2.29	2.913 (2)	121
C8—H8B···Cg1ⁱ	0.97	2.69	3.6411 (19)	166

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

This work was supported by the Natural Science Foundation of the Higher Education Institutions of the Education Bureau of Anhui Province (grant No. KJ2011B154), the Science and Technology Planning Project of Huainan (grant No. 2011 A08101) and Huainan Union University, China (grant No. LYB1005).

References

Bailly, C. (2004). Curr. Med. Chem. Anticancer Agents, 4, 363–378. CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Feng, C.-T., Wang, L.-D., Yan, Y.-G., Liu, J. & Li, S.-H. (2012). Med. Chem. Res. 21, 315–320. Web of Science CrossRef CAS Google Scholar
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zou, Y.-Q., Lu, L.-Q., Fu, L., Chang, N.-J., Rong, J., Chen, J.-R. & Xiao, W.-J. (2011). Angew. Chem. Int. Ed. 50, 7171–7175. Web of Science CSD CrossRef CAS Google Scholar

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