Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexa-hydro-benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl-ate.

In the title compound, C(24)H(23)NO(3), the dihedral angle between the naphthalene ring system and the phenyl ring is 76.82 (6)°. The pyrrolidine ring adopts an envelope conformation. In the crystal, weak inter-molecular C-H⋯O and C-H⋯π inter-actions are observed.

Related literature

For the biological activity of chromenopyrrole, see: Caine (1993 ▶); Tidey (1992 ▶); Carlson (1993 ▶); Sokoloff et al. (1990 ▶); Wilner (1985 ▶); Sobral & Rocha Gonsalves (2001a ▶,b ▶); Brockmann & Tour (1995 ▶); Suslick et al. (1992 ▶); Di Natale et al. (1998 ▶). For a related structure, see: Nirmala et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H23NO3

M = 373.43

Monoclinic,

a = 13.2332 (6) Å

b = 10.3574 (4) Å

c = 15.0865 (6) Å

β = 111.530 (2)°

V = 1923.50 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEX2 CCD diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.987

19089 measured reflections

3499 independent reflections

2413 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.02

3499 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012914/is2404sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012914/is2404Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H23NO3	F(000) = 792
Mr = 373.43	Dx = 1.290 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3865 reflections
a = 13.2332 (6) Å	θ = 1.8–25.3°
b = 10.3574 (4) Å	µ = 0.09 mm−1
c = 15.0865 (6) Å	T = 293 K
β = 111.530 (2)°	Block, colourless
V = 1923.50 (14) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Bruker Kappa APEX2 CCD diffractometer	3499 independent reflections
Radiation source: fine-focus sealed tube	2413 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 0 pixels mm-1	θmax = 25.3°, θmin = 2.4°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
Tmin = 0.979, Tmax = 0.987	l = −18→18
19089 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0458P)2 + 0.3587P] where P = (Fo2 + 2Fc2)/3
3499 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.87620 (10)	0.79656 (11)	0.16896 (8)	0.0560 (3)
O3	0.64358 (10)	1.04425 (13)	0.12731 (9)	0.0610 (4)
C8	0.80155 (13)	0.91239 (15)	0.02018 (11)	0.0404 (4)
O2	0.72839 (11)	0.94550 (14)	0.26458 (9)	0.0684 (4)
C7	0.83173 (14)	0.80090 (16)	0.07191 (12)	0.0473 (4)
N1	0.91939 (11)	1.10692 (13)	0.08087 (9)	0.0452 (4)
C13	0.81799 (13)	1.03987 (15)	0.07102 (10)	0.0388 (4)
H13	0.7558	1.0965	0.0393	0.047*
C9	0.74815 (13)	0.90220 (16)	−0.08105 (12)	0.0452 (4)
C11	0.91380 (14)	0.91616 (15)	0.21733 (12)	0.0483 (4)
H11A	0.9827	0.9387	0.2124	0.058*
H11B	0.9258	0.9059	0.2843	0.058*
C10	0.70597 (14)	1.00976 (19)	−0.14052 (12)	0.0508 (4)
H10	0.7133	1.0915	−0.1134	0.061*
C4	0.73409 (15)	0.77937 (18)	−0.12524 (13)	0.0553 (5)
C12	0.83340 (13)	1.02418 (15)	0.17618 (10)	0.0394 (4)
C23	0.73092 (14)	0.99806 (16)	0.19506 (11)	0.0439 (4)
C6	0.81600 (17)	0.67864 (17)	0.02815 (15)	0.0605 (5)
H6	0.8373	0.6044	0.0650	0.073*
C17	0.95781 (14)	1.15779 (15)	0.32102 (11)	0.0440 (4)
C15	0.88052 (14)	1.15911 (15)	0.21892 (11)	0.0448 (4)
H15	0.8187	1.2134	0.2160	0.054*
C5	0.76969 (17)	0.66982 (19)	−0.06782 (15)	0.0665 (6)
H5	0.7613	0.5889	−0.0964	0.080*
C16	0.93000 (15)	1.15213 (18)	−0.00619 (12)	0.0555 (5)
H16A	0.8733	1.2130	−0.0371	0.083*
H16B	0.9244	1.0802	−0.0479	0.083*
H16C	0.9993	1.1931	0.0087	0.083*
C3	0.68054 (18)	0.7705 (2)	−0.22541 (15)	0.0715 (6)
H3	0.6717	0.6900	−0.2546	0.086*
C22	1.06811 (15)	1.14119 (17)	0.34720 (13)	0.0580 (5)
H22	1.0977	1.1295	0.3006	0.070*
C1	0.65478 (16)	0.9971 (2)	−0.23651 (13)	0.0629 (5)
H1	0.6280	1.0699	−0.2738	0.076*
C2	0.64222 (18)	0.8763 (3)	−0.27927 (15)	0.0753 (6)
H2	0.6075	0.8685	−0.3449	0.090*
C14	0.92485 (17)	1.21276 (17)	0.14582 (12)	0.0580 (5)
H14A	0.8811	1.2850	0.1117	0.070*
H14B	0.9992	1.2417	0.1771	0.070*
C18	0.91714 (17)	1.17418 (17)	0.39259 (12)	0.0571 (5)
H18	0.8428	1.1855	0.3765	0.069*
C19	0.9842 (2)	1.1741 (2)	0.48683 (14)	0.0760 (7)
H19	0.9550	1.1846	0.5338	0.091*
C21	1.13528 (18)	1.14174 (19)	0.44215 (15)	0.0725 (6)
H21	1.2097	1.1306	0.4588	0.087*
C20	1.0936 (2)	1.1585 (2)	0.51178 (15)	0.0784 (7)
H20	1.1392	1.1594	0.5756	0.094*
C24	0.54215 (16)	1.0313 (2)	0.14187 (16)	0.0749 (6)
H24A	0.5298	0.9421	0.1518	0.112*
H24B	0.4839	1.0628	0.0868	0.112*
H24C	0.5453	1.0806	0.1967	0.112*

	U11	U22	U33	U12	U13	U23
O1	0.0678 (9)	0.0358 (7)	0.0620 (8)	0.0033 (6)	0.0211 (6)	0.0046 (6)
O3	0.0449 (7)	0.0785 (9)	0.0673 (8)	0.0114 (7)	0.0296 (6)	0.0219 (7)
C8	0.0387 (9)	0.0373 (9)	0.0525 (10)	−0.0033 (7)	0.0254 (8)	−0.0041 (8)
O2	0.0685 (9)	0.0824 (10)	0.0587 (8)	−0.0099 (7)	0.0284 (7)	0.0197 (7)
C7	0.0473 (11)	0.0413 (10)	0.0600 (11)	−0.0024 (8)	0.0278 (9)	−0.0016 (8)
N1	0.0440 (9)	0.0439 (8)	0.0500 (8)	−0.0079 (6)	0.0199 (6)	0.0019 (6)
C13	0.0379 (9)	0.0367 (9)	0.0441 (9)	0.0004 (7)	0.0180 (7)	0.0023 (7)
C9	0.0407 (10)	0.0490 (10)	0.0540 (10)	−0.0075 (8)	0.0270 (8)	−0.0092 (8)
C11	0.0501 (11)	0.0396 (10)	0.0527 (10)	0.0019 (8)	0.0159 (8)	0.0033 (8)
C10	0.0472 (10)	0.0607 (12)	0.0481 (10)	−0.0038 (9)	0.0217 (8)	−0.0073 (9)
C4	0.0563 (12)	0.0537 (12)	0.0659 (12)	−0.0100 (9)	0.0343 (10)	−0.0151 (10)
C12	0.0400 (9)	0.0372 (9)	0.0411 (8)	0.0006 (7)	0.0151 (7)	0.0032 (7)
C23	0.0505 (11)	0.0385 (9)	0.0441 (9)	−0.0032 (8)	0.0190 (8)	−0.0006 (8)
C6	0.0731 (14)	0.0364 (10)	0.0847 (14)	−0.0042 (9)	0.0437 (11)	−0.0044 (9)
C17	0.0488 (11)	0.0331 (9)	0.0479 (9)	−0.0020 (8)	0.0150 (8)	−0.0029 (7)
C15	0.0481 (10)	0.0374 (9)	0.0470 (9)	0.0000 (8)	0.0151 (8)	−0.0005 (7)
C5	0.0817 (15)	0.0477 (12)	0.0858 (15)	−0.0156 (11)	0.0492 (12)	−0.0239 (11)
C16	0.0533 (12)	0.0587 (12)	0.0626 (11)	−0.0069 (9)	0.0310 (9)	0.0072 (9)
C3	0.0717 (15)	0.0794 (16)	0.0716 (14)	−0.0169 (12)	0.0357 (12)	−0.0354 (12)
C22	0.0532 (12)	0.0536 (12)	0.0621 (12)	−0.0017 (9)	0.0151 (9)	−0.0105 (9)
C1	0.0578 (12)	0.0812 (15)	0.0518 (11)	0.0006 (10)	0.0225 (9)	−0.0056 (10)
C2	0.0688 (15)	0.1018 (19)	0.0555 (12)	−0.0036 (13)	0.0228 (11)	−0.0226 (13)
C14	0.0734 (14)	0.0471 (11)	0.0495 (10)	−0.0171 (9)	0.0178 (9)	−0.0005 (8)
C18	0.0661 (13)	0.0527 (11)	0.0553 (11)	−0.0083 (9)	0.0255 (10)	−0.0086 (9)
C19	0.104 (2)	0.0731 (15)	0.0519 (12)	−0.0254 (13)	0.0300 (13)	−0.0113 (10)
C21	0.0602 (14)	0.0545 (13)	0.0789 (15)	−0.0040 (10)	−0.0026 (12)	−0.0073 (11)
C20	0.103 (2)	0.0590 (14)	0.0502 (12)	−0.0214 (13)	0.0010 (13)	−0.0019 (10)
C24	0.0524 (13)	0.0869 (16)	0.1010 (16)	0.0095 (11)	0.0467 (12)	0.0171 (13)

O1—C7	1.3637 (19)	C17—C18	1.382 (2)
O1—C11	1.4311 (19)	C17—C15	1.504 (2)
O3—C23	1.320 (2)	C15—C14	1.531 (2)
O3—C24	1.444 (2)	C15—H15	0.9800
C8—C7	1.369 (2)	C5—H5	0.9300
C8—C9	1.432 (2)	C16—H16A	0.9600
C8—C13	1.502 (2)	C16—H16B	0.9600
O2—C23	1.1931 (18)	C16—H16C	0.9600
C7—C6	1.408 (2)	C3—C2	1.347 (3)
N1—C16	1.449 (2)	C3—H3	0.9300
N1—C14	1.454 (2)	C22—C21	1.381 (3)
N1—C13	1.469 (2)	C22—H22	0.9300
C13—C12	1.532 (2)	C1—C2	1.389 (3)
C13—H13	0.9800	C1—H1	0.9300
C9—C10	1.411 (2)	C2—H2	0.9300
C9—C4	1.417 (2)	C14—H14A	0.9700
C11—C12	1.511 (2)	C14—H14B	0.9700
C11—H11A	0.9700	C18—C19	1.372 (3)
C11—H11B	0.9700	C18—H18	0.9300
C10—C1	1.361 (2)	C19—C20	1.364 (3)
C10—H10	0.9300	C19—H19	0.9300
C4—C5	1.400 (3)	C21—C20	1.365 (3)
C4—C3	1.417 (3)	C21—H21	0.9300
C12—C23	1.509 (2)	C20—H20	0.9300
C12—C15	1.569 (2)	C24—H24A	0.9600
C6—C5	1.352 (3)	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C17—C22	1.376 (2)
C7—O1—C11	116.82 (12)	C14—C15—C12	103.10 (12)
C23—O3—C24	116.58 (14)	C17—C15—H15	107.1
C7—C8—C9	118.20 (15)	C14—C15—H15	107.1
C7—C8—C13	119.55 (14)	C12—C15—H15	107.1
C9—C8—C13	122.11 (14)	C6—C5—C4	121.67 (17)
O1—C7—C8	124.11 (15)	C6—C5—H5	119.2
O1—C7—C6	113.89 (16)	C4—C5—H5	119.2
C8—C7—C6	121.97 (16)	N1—C16—H16A	109.5
C16—N1—C14	111.70 (13)	N1—C16—H16B	109.5
C16—N1—C13	116.73 (13)	H16A—C16—H16B	109.5
C14—N1—C13	104.01 (13)	N1—C16—H16C	109.5
N1—C13—C8	115.02 (13)	H16A—C16—H16C	109.5
N1—C13—C12	100.13 (12)	H16B—C16—H16C	109.5
C8—C13—C12	112.01 (13)	C2—C3—C4	121.4 (2)
N1—C13—H13	109.8	C2—C3—H3	119.3
C8—C13—H13	109.8	C4—C3—H3	119.3
C12—C13—H13	109.8	C17—C22—C21	120.56 (19)
C10—C9—C4	117.20 (15)	C17—C22—H22	119.7
C10—C9—C8	123.04 (15)	C21—C22—H22	119.7
C4—C9—C8	119.75 (16)	C10—C1—C2	120.6 (2)
O1—C11—C12	111.76 (13)	C10—C1—H1	119.7
O1—C11—H11A	109.3	C2—C1—H1	119.7
C12—C11—H11A	109.3	C3—C2—C1	119.85 (19)
O1—C11—H11B	109.3	C3—C2—H2	120.1
C12—C11—H11B	109.3	C1—C2—H2	120.1
H11A—C11—H11B	107.9	N1—C14—C15	105.93 (13)
C1—C10—C9	121.78 (18)	N1—C14—H14A	110.6
C1—C10—H10	119.1	C15—C14—H14A	110.6
C9—C10—H10	119.1	N1—C14—H14B	110.6
C5—C4—C9	118.71 (17)	C15—C14—H14B	110.6
C5—C4—C3	122.04 (19)	H14A—C14—H14B	108.7
C9—C4—C3	119.19 (19)	C19—C18—C17	121.3 (2)
C23—C12—C11	109.62 (13)	C19—C18—H18	119.3
C23—C12—C13	115.29 (13)	C17—C18—H18	119.3
C11—C12—C13	108.05 (13)	C20—C19—C18	120.2 (2)
C23—C12—C15	109.34 (13)	C20—C19—H19	119.9
C11—C12—C15	112.14 (13)	C18—C19—H19	119.9
C13—C12—C15	102.29 (12)	C20—C21—C22	120.7 (2)
O2—C23—O3	123.16 (16)	C20—C21—H21	119.7
O2—C23—C12	124.39 (16)	C22—C21—H21	119.7
O3—C23—C12	112.40 (13)	C19—C20—C21	119.35 (19)
C5—C6—C7	119.59 (18)	C19—C20—H20	120.3
C5—C6—H6	120.2	C21—C20—H20	120.3
C7—C6—H6	120.2	O3—C24—H24A	109.5
C22—C17—C18	117.86 (16)	O3—C24—H24B	109.5
C22—C17—C15	123.11 (16)	H24A—C24—H24B	109.5
C18—C17—C15	119.03 (16)	O3—C24—H24C	109.5
C17—C15—C14	116.40 (15)	H24A—C24—H24C	109.5
C17—C15—C12	115.53 (13)	H24B—C24—H24C	109.5
C11—O1—C7—C8	−13.5 (2)	C13—C12—C23—O2	155.96 (16)
C11—O1—C7—C6	168.25 (15)	C15—C12—C23—O2	−89.50 (19)
C9—C8—C7—O1	−175.27 (14)	C11—C12—C23—O3	−148.53 (14)
C13—C8—C7—O1	0.5 (2)	C13—C12—C23—O3	−26.37 (19)
C9—C8—C7—C6	2.8 (2)	C15—C12—C23—O3	88.17 (16)
C13—C8—C7—C6	178.56 (16)	O1—C7—C6—C5	178.20 (16)
C16—N1—C13—C8	66.33 (19)	C8—C7—C6—C5	−0.1 (3)
C14—N1—C13—C8	−170.14 (13)	C22—C17—C15—C14	−31.9 (2)
C16—N1—C13—C12	−173.44 (13)	C18—C17—C15—C14	148.01 (16)
C14—N1—C13—C12	−49.91 (15)	C22—C17—C15—C12	89.3 (2)
C7—C8—C13—N1	94.95 (17)	C18—C17—C15—C12	−90.82 (19)
C9—C8—C13—N1	−89.46 (18)	C23—C12—C15—C17	88.85 (17)
C7—C8—C13—C12	−18.5 (2)	C11—C12—C15—C17	−32.95 (19)
C9—C8—C13—C12	157.09 (14)	C13—C12—C15—C17	−148.48 (14)
C7—C8—C9—C10	174.89 (15)	C23—C12—C15—C14	−143.05 (14)
C13—C8—C9—C10	−0.8 (2)	C11—C12—C15—C14	95.15 (16)
C7—C8—C9—C4	−3.9 (2)	C13—C12—C15—C14	−20.38 (16)
C13—C8—C9—C4	−179.52 (14)	C7—C6—C5—C4	−1.7 (3)
C7—O1—C11—C12	44.22 (19)	C9—C4—C5—C6	0.5 (3)
C4—C9—C10—C1	−0.7 (2)	C3—C4—C5—C6	−176.74 (18)
C8—C9—C10—C1	−179.46 (15)	C5—C4—C3—C2	176.87 (19)
C10—C9—C4—C5	−176.58 (16)	C9—C4—C3—C2	−0.4 (3)
C8—C9—C4—C5	2.3 (2)	C18—C17—C22—C21	−0.3 (3)
C10—C9—C4—C3	0.8 (2)	C15—C17—C22—C21	179.54 (17)
C8—C9—C4—C3	179.63 (15)	C9—C10—C1—C2	0.1 (3)
O1—C11—C12—C23	66.29 (17)	C4—C3—C2—C1	−0.1 (3)
O1—C11—C12—C13	−60.09 (17)	C10—C1—C2—C3	0.3 (3)
O1—C11—C12—C15	−172.07 (13)	C16—N1—C14—C15	164.03 (14)
N1—C13—C12—C23	160.94 (13)	C13—N1—C14—C15	37.29 (17)
C8—C13—C12—C23	−76.68 (17)	C17—C15—C14—N1	118.28 (16)
N1—C13—C12—C11	−76.07 (15)	C12—C15—C14—N1	−9.28 (17)
C8—C13—C12—C11	46.31 (17)	C22—C17—C18—C19	0.0 (3)
N1—C13—C12—C15	42.39 (15)	C15—C17—C18—C19	−179.84 (17)
C8—C13—C12—C15	164.78 (13)	C17—C18—C19—C20	0.5 (3)
C24—O3—C23—O2	1.5 (3)	C17—C22—C21—C20	0.1 (3)
C24—O3—C23—C12	−176.18 (15)	C18—C19—C20—C21	−0.7 (3)
C11—C12—C23—O2	33.8 (2)	C22—C21—C20—C19	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···N1	0.97	2.54	2.874 (2)	100
C13—H13···O3	0.98	2.39	2.7366 (19)	100
C15—H15···O2i	0.98	2.53	3.347 (2)	141
C16—H16C···Cgii	0.96	2.79	3.689 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2i	0.98	2.53	3.347 (2)	141
C16—H16C⋯Cgii	0.96	2.79	3.689 (4)	156

Symmetry codes: (i) ; (ii) . Cg is the centroid of the C4–C9 ring.