Methyl 3-(4-bromo­phen­yl)-1-methyl-1,2,3,3a,4,9b-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

Nirmala, S.; Kamala, E.T.S.; Sudha, L.; Kathiravan, S.; Raghunathan, R.

doi:10.1107/S1600536809029389

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o2028-o2029

doi:10.1107/S1600536809029389

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Methyl 3-(4-bromophenyl)-1-methyl-1,2,3,3a,4,9b-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate

S. Nirmala,^a E. Theboral Sugi Kamala,^a L. Sudha,^b ^* S. Kathiravan ^c and R. Raghunathan ^c

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: sudharose18@gmail.com

(Received 17 July 2009; accepted 23 July 2009; online 29 July 2009)

In the title compound, C₂₄H₂₂BrNO₃, the dihydropyran ring adopts a half-chair conformation, whereas the pyrrolidine ring is in an envelope conformation. The bromophenyl group is oriented at an angle of 66.44 (4)° with respect to the naphthalene ring system. In the crystal structure, molecules are linked into centrosymmetric dimers by C—H⋯π interactions and the dimers are connected via C—H⋯Br hydrogen bonds. The crystal structure is further stabilized by π–π interactions [centroid–centroid distance = 3.453 (1) Å].

Related literature

For the biological activity of pyrrole derivatives, see: Biava et al. (2005 ); Borthwick et al. (2000 ); Caine (1993 ); Carlson (1993 ); Fernandes et al. (2004 ); Jiang et al. (2004 ); Sokoloff et al. (1990 ); Tidey (1992 ); Wilner (1985 ). For a related structure, see: Nirmala et al. (2009 ). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₂BrNO₃
M_r = 452.34
Monoclinic, P 2₁ /c
a = 12.7856 (4) Å
b = 19.9348 (6) Å
c = 8.0189 (3) Å
β = 106.163 (2)°
V = 1963.06 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.12 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.619, T_max = 0.742
49847 measured reflections
6162 independent reflections
4068 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.102
S = 1.02
6162 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24A⋯Br1ⁱ	0.96	2.84	3.789 (3)	172
C20—H20⋯Cg1ⁱⁱ	0.93	2.77	3.653 (2)	160
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+2. Cg1 is the centroid of the C3–C8 ring.

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: 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/S1600536809029389/ci2858sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029389/ci2858Isup2.hkl

checkCIF report

Comment top

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993), aggressiveness (Tidey, 1992), parkinson's disease (Carlson, 1993), psychoses, memory disorders (Sokoloff et al., 1990), anxiety and depression (Wilner, 1985). Pyrrole derivatives have good in vitro activities against mycobacteria and candidae (Biava et al., 2005). These derivatives also possess anti-inflammatory (Fernandes et al., 2004) and antiviral (Borthwick et al., 2000) activities. It has also been shown that N-substituted pyrrole derivatives inhibit human immuno deficiency virus type-I (HIV-I) (Jiang et al., 2004). In view of its medicinal importance, the crystal structure determination of the title compound was undertaken.

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for a similar structure (Nirmala et al., 2009). The sum of bond angles around atom N1 [332.0 (8)°] is in accordance with sp³ hybridization. The naphthalene ring system (C2-C11) and the bromophenyl group (Br1/C16-C21) are oriented at an angle of 66.44 (4)° with respect to each other. The heterocyclic ring (O1/C1/C2/C11-C13) of the chromenopyrrole unit adopts a half chair conformation with puckering parameters Q = 0.468 (2) Å, θ = 132.5 (2)° and ϕ = 83.1 (3)° (Cremer & Pople, 1975). The pyrrolidine ring (N1/C1/C13-C15) adopts an envelope conformation with puckering parameters q₂ = 0.433 (2) Å and ϕ = 214.5 (3)° (Cremer & Pople, 1975). Atom C1 deviates by -0.654 Å from the least-square plane through the remaining four atoms.

The crystal packing is stabilized by intermolecular C—H···Br hydrogen bonds. The molecules are linked into centrosymmetric dimers by C—H···π (C20—H20···Cg1; Cg1 is the centroid of the C3—C8 ring) interactions (Table 1). In addition, π–π interactions between C3—C8 rings at (x, y, z) and (2 -x, 1 -y, 2 -z) stabilize the structure, with a centroid-to-centroid distance of 3.453 (1) Å.

Related literature top

For the biological activity of pyrrole derivatives, see: Biava et al. (2005); Borthwick et al. (2000); Caine (1993); Carlson (1993); Fernandes et al. (2004); Jiang et al. (2004); Sokoloff et al. (1990); Tidey (1992); Wilner (1985). For a related structure, see: Nirmala et al. (2009). For ring-puckering parameters, see: Cremer & Pople (1975). Cg1 is the centroid of the C3–C8 ring.

Experimental top

A mixture of (Z)-methyl 2-((1-formylnaphthalen-2-yloxy)methyl)-3-(4-bromophenyl)acrylate (20 mmol) and sarcosine (30 mmol) were refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. Chloroform and methanol (1:1) solvent mixture was used for the crystallization under slow evaporation method.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. The molecular structure of the title compound, with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the molecules viewed down a axis. H atoms not involed in C—H···Br and C—H···π interactions have been omitted.

Methyl 3-(4-bromophenyl)-1-methyl-1,2,3,3a,4,9b- hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate top

Crystal data top

C₂₄H₂₂BrNO₃	F(000) = 928
M_r = 452.34	D_x = 1.531 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14860 reflections
a = 12.7856 (4) Å	θ = 2.6–25.2°
b = 19.9348 (6) Å	µ = 2.12 mm⁻¹
c = 8.0189 (3) Å	T = 293 K
β = 106.163 (2)°	Prism, colourless
V = 1963.06 (11) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEXII area-detector diffractometer	6162 independent reflections
Radiation source: fine-focus sealed tube	4068 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 30.9°, θ_min = 2.0°
Absorption correction: multi-scan (Blessing, 1995)	h = −18→18
T_min = 0.619, T_max = 0.742	k = −16→28
49847 measured reflections	l = −11→11

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0439P)² + 0.7192P] where P = (F_o² + 2F_c²)/3
6162 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₄H₂₂BrNO₃	V = 1963.06 (11) Å³
M_r = 452.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7856 (4) Å	µ = 2.12 mm⁻¹
b = 19.9348 (6) Å	T = 293 K
c = 8.0189 (3) Å	0.25 × 0.20 × 0.15 mm
β = 106.163 (2)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	6162 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	4068 reflections with I > 2σ(I)
T_min = 0.619, T_max = 0.742	R_int = 0.031
49847 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	Δρ_max = 0.58 e Å⁻³
6162 reflections	Δρ_min = −0.51 e Å⁻³
262 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
C1	0.68758 (13)	0.58289 (8)	0.6893 (2)	0.0281 (3)
H1	0.7433	0.6171	0.6940	0.034*
C2	0.73957 (13)	0.52048 (8)	0.7836 (2)	0.0287 (3)
C3	0.84557 (13)	0.49812 (8)	0.7827 (2)	0.0306 (3)
C4	0.91361 (15)	0.53431 (10)	0.7029 (2)	0.0381 (4)
H4	0.8889	0.5745	0.6470	0.046*
C5	1.01452 (16)	0.51164 (11)	0.7061 (2)	0.0455 (5)
H5	1.0576	0.5367	0.6530	0.055*
C6	1.05416 (17)	0.45149 (12)	0.7878 (3)	0.0510 (5)
H6	1.1226	0.4360	0.7869	0.061*
C7	0.99246 (17)	0.41579 (11)	0.8685 (3)	0.0474 (5)
H7	1.0195	0.3759	0.9241	0.057*
C8	0.88813 (15)	0.43783 (9)	0.8699 (2)	0.0357 (4)
C9	0.82649 (16)	0.40202 (9)	0.9600 (3)	0.0425 (4)
H9	0.8535	0.3620	1.0149	0.051*
C10	0.72848 (16)	0.42484 (9)	0.9681 (2)	0.0417 (4)
H10	0.6893	0.4013	1.0309	0.050*
C11	0.68588 (14)	0.48451 (8)	0.8811 (2)	0.0329 (3)
C12	0.52824 (14)	0.55294 (8)	0.7923 (2)	0.0338 (4)
H12A	0.4714	0.5700	0.8396	0.041*
H12B	0.4935	0.5324	0.6810	0.041*
C13	0.59903 (13)	0.61089 (8)	0.7656 (2)	0.0289 (3)
C14	0.53395 (14)	0.65915 (8)	0.6186 (2)	0.0333 (4)
H14	0.5695	0.7031	0.6403	0.040*
C15	0.55720 (16)	0.63062 (10)	0.4547 (2)	0.0424 (4)
H15A	0.4896	0.6189	0.3692	0.051*
H15B	0.5952	0.6635	0.4040	0.051*
C16	0.41597 (13)	0.66967 (8)	0.6127 (2)	0.0308 (3)
C17	0.38794 (16)	0.72456 (9)	0.6967 (3)	0.0449 (5)
H17	0.4420	0.7544	0.7536	0.054*
C18	0.28173 (17)	0.73619 (10)	0.6981 (3)	0.0491 (5)
H18	0.2645	0.7732	0.7558	0.059*
C19	0.20242 (15)	0.69243 (9)	0.6136 (2)	0.0379 (4)
C20	0.22678 (14)	0.63726 (9)	0.5282 (2)	0.0362 (4)
H20	0.1721	0.6077	0.4715	0.043*
C21	0.33319 (14)	0.62635 (8)	0.5280 (2)	0.0337 (4)
H21	0.3499	0.5892	0.4699	0.040*
C22	0.68903 (16)	0.55698 (9)	0.3883 (2)	0.0385 (4)
H22A	0.7326	0.5177	0.4259	0.058*
H22B	0.7357	0.5945	0.3858	0.058*
H22C	0.6413	0.5496	0.2740	0.058*
C23	0.63964 (14)	0.65052 (8)	0.9323 (2)	0.0338 (4)
C24	0.7836 (2)	0.71536 (12)	1.1053 (3)	0.0631 (7)
H24A	0.8555	0.7299	1.1072	0.095*
H24B	0.7869	0.6896	1.2078	0.095*
H24C	0.7378	0.7538	1.1018	0.095*
N1	0.62481 (12)	0.57086 (7)	0.50776 (18)	0.0322 (3)
O1	0.58933 (10)	0.50339 (6)	0.90663 (17)	0.0412 (3)
O2	0.73947 (11)	0.67466 (8)	0.9542 (2)	0.0529 (4)
O3	0.58771 (13)	0.66160 (9)	1.03113 (19)	0.0594 (4)
Br1	0.056104 (18)	0.708461 (13)	0.61041 (4)	0.06427 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0292 (8)	0.0257 (7)	0.0314 (8)	−0.0020 (6)	0.0121 (6)	0.0029 (6)
C2	0.0324 (8)	0.0275 (7)	0.0275 (8)	0.0002 (6)	0.0103 (7)	0.0006 (6)
C3	0.0332 (8)	0.0333 (8)	0.0255 (8)	0.0009 (6)	0.0085 (6)	−0.0059 (6)
C4	0.0382 (9)	0.0452 (10)	0.0322 (9)	0.0007 (7)	0.0118 (7)	−0.0013 (7)
C5	0.0370 (10)	0.0638 (13)	0.0382 (10)	−0.0007 (9)	0.0144 (8)	−0.0083 (9)
C6	0.0379 (10)	0.0685 (14)	0.0469 (12)	0.0140 (10)	0.0121 (9)	−0.0119 (10)
C7	0.0477 (11)	0.0486 (11)	0.0429 (11)	0.0169 (9)	0.0076 (9)	−0.0056 (9)
C8	0.0382 (9)	0.0375 (9)	0.0297 (9)	0.0063 (7)	0.0064 (7)	−0.0052 (7)
C9	0.0523 (11)	0.0324 (9)	0.0405 (10)	0.0103 (8)	0.0092 (9)	0.0053 (8)
C10	0.0512 (11)	0.0344 (9)	0.0426 (10)	0.0008 (8)	0.0181 (9)	0.0105 (8)
C11	0.0362 (9)	0.0315 (8)	0.0326 (9)	0.0004 (7)	0.0124 (7)	0.0030 (7)
C12	0.0304 (8)	0.0343 (8)	0.0397 (9)	0.0005 (6)	0.0146 (7)	0.0089 (7)
C13	0.0278 (8)	0.0288 (7)	0.0324 (8)	0.0006 (6)	0.0122 (6)	0.0043 (6)
C14	0.0322 (8)	0.0302 (8)	0.0375 (9)	0.0009 (6)	0.0100 (7)	0.0072 (7)
C15	0.0399 (10)	0.0523 (11)	0.0375 (10)	0.0099 (8)	0.0150 (8)	0.0143 (8)
C16	0.0321 (8)	0.0260 (7)	0.0334 (9)	0.0029 (6)	0.0077 (7)	0.0028 (6)
C17	0.0396 (10)	0.0328 (9)	0.0559 (12)	0.0008 (7)	0.0024 (9)	−0.0141 (8)
C18	0.0480 (11)	0.0385 (10)	0.0585 (13)	0.0110 (8)	0.0106 (10)	−0.0155 (9)
C19	0.0348 (9)	0.0392 (9)	0.0401 (10)	0.0095 (7)	0.0110 (8)	0.0041 (7)
C20	0.0348 (9)	0.0346 (9)	0.0373 (9)	−0.0027 (7)	0.0068 (7)	−0.0015 (7)
C21	0.0377 (9)	0.0293 (8)	0.0346 (9)	0.0016 (7)	0.0110 (7)	−0.0045 (7)
C22	0.0453 (10)	0.0421 (10)	0.0315 (9)	−0.0002 (8)	0.0164 (8)	0.0016 (7)
C23	0.0333 (9)	0.0317 (8)	0.0367 (9)	0.0059 (7)	0.0103 (7)	0.0042 (7)
C24	0.0480 (13)	0.0636 (14)	0.0739 (16)	−0.0068 (10)	0.0107 (11)	−0.0321 (12)
N1	0.0346 (7)	0.0358 (7)	0.0280 (7)	−0.0006 (6)	0.0118 (6)	0.0051 (6)
O1	0.0393 (7)	0.0416 (7)	0.0498 (8)	0.0059 (5)	0.0238 (6)	0.0190 (6)
O2	0.0394 (7)	0.0582 (9)	0.0646 (9)	−0.0116 (6)	0.0203 (7)	−0.0283 (7)
O3	0.0555 (9)	0.0822 (11)	0.0476 (8)	−0.0085 (8)	0.0263 (7)	−0.0169 (8)
Br1	0.04256 (13)	0.07000 (17)	0.0859 (2)	0.01747 (10)	0.02724 (12)	0.00945 (12)

Geometric parameters (Å, º) top

C1—N1	1.473 (2)	C14—C16	1.511 (2)
C1—C2	1.510 (2)	C14—C15	1.536 (3)
C1—C13	1.534 (2)	C14—H14	0.98
C1—H1	0.98	C15—N1	1.464 (2)
C2—C11	1.377 (2)	C15—H15A	0.97
C2—C3	1.429 (2)	C15—H15B	0.97
C3—C4	1.413 (2)	C16—C17	1.383 (2)
C3—C8	1.421 (2)	C16—C21	1.388 (2)
C4—C5	1.361 (3)	C17—C18	1.381 (3)
C4—H4	0.93	C17—H17	0.93
C5—C6	1.392 (3)	C18—C19	1.366 (3)
C5—H5	0.93	C18—H18	0.93
C6—C7	1.353 (3)	C19—C20	1.376 (3)
C6—H6	0.93	C19—Br1	1.8910 (18)
C7—C8	1.408 (3)	C20—C21	1.378 (2)
C7—H7	0.93	C20—H20	0.93
C8—C9	1.403 (3)	C21—H21	0.93
C9—C10	1.352 (3)	C22—N1	1.452 (2)
C9—H9	0.93	C22—H22A	0.96
C10—C11	1.410 (2)	C22—H22B	0.96
C10—H10	0.93	C22—H22C	0.96
C11—O1	1.360 (2)	C23—O3	1.188 (2)
C12—O1	1.424 (2)	C23—O2	1.329 (2)
C12—C13	1.519 (2)	C24—O2	1.437 (3)
C12—H12A	0.97	C24—H24A	0.96
C12—H12B	0.97	C24—H24B	0.96
C13—C23	1.514 (2)	C24—H24C	0.96
C13—C14	1.569 (2)

N1—C1—C2	113.78 (13)	C16—C14—C13	115.15 (13)
N1—C1—C13	101.17 (13)	C15—C14—C13	103.15 (13)
C2—C1—C13	111.80 (13)	C16—C14—H14	107.0
N1—C1—H1	109.9	C15—C14—H14	107.0
C2—C1—H1	109.9	C13—C14—H14	107.0
C13—C1—H1	109.9	N1—C15—C14	106.96 (14)
C11—C2—C3	117.65 (15)	N1—C15—H15A	110.3
C11—C2—C1	119.57 (14)	C14—C15—H15A	110.3
C3—C2—C1	122.72 (14)	N1—C15—H15B	110.3
C4—C3—C8	117.08 (16)	C14—C15—H15B	110.3
C4—C3—C2	123.20 (15)	H15A—C15—H15B	108.6
C8—C3—C2	119.69 (15)	C17—C16—C21	117.69 (16)
C5—C4—C3	121.46 (18)	C17—C16—C14	119.11 (15)
C5—C4—H4	119.3	C21—C16—C14	123.20 (15)
C3—C4—H4	119.3	C18—C17—C16	121.72 (17)
C4—C5—C6	120.93 (19)	C18—C17—H17	119.1
C4—C5—H5	119.5	C16—C17—H17	119.1
C6—C5—H5	119.5	C19—C18—C17	118.97 (17)
C7—C6—C5	119.57 (18)	C19—C18—H18	120.5
C7—C6—H6	120.2	C17—C18—H18	120.5
C5—C6—H6	120.2	C18—C19—C20	121.18 (17)
C6—C7—C8	121.30 (19)	C18—C19—Br1	119.58 (14)
C6—C7—H7	119.4	C20—C19—Br1	119.23 (14)
C8—C7—H7	119.4	C19—C20—C21	119.14 (16)
C9—C8—C7	120.97 (17)	C19—C20—H20	120.4
C9—C8—C3	119.39 (16)	C21—C20—H20	120.4
C7—C8—C3	119.61 (18)	C20—C21—C16	121.29 (15)
C10—C9—C8	120.98 (17)	C20—C21—H21	119.4
C10—C9—H9	119.5	C16—C21—H21	119.4
C8—C9—H9	119.5	N1—C22—H22A	109.5
C9—C10—C11	119.71 (17)	N1—C22—H22B	109.5
C9—C10—H10	120.1	H22A—C22—H22B	109.5
C11—C10—H10	120.1	N1—C22—H22C	109.5
O1—C11—C2	123.97 (15)	H22A—C22—H22C	109.5
O1—C11—C10	113.62 (15)	H22B—C22—H22C	109.5
C2—C11—C10	122.39 (16)	O3—C23—O2	122.60 (17)
O1—C12—C13	112.14 (14)	O3—C23—C13	124.61 (16)
O1—C12—H12A	109.2	O2—C23—C13	112.73 (14)
C13—C12—H12A	109.2	O2—C24—H24A	109.5
O1—C12—H12B	109.2	O2—C24—H24B	109.5
C13—C12—H12B	109.2	H24A—C24—H24B	109.5
H12A—C12—H12B	107.9	O2—C24—H24C	109.5
C23—C13—C12	110.09 (14)	H24A—C24—H24C	109.5
C23—C13—C1	115.59 (13)	H24B—C24—H24C	109.5
C12—C13—C1	108.33 (13)	C22—N1—C15	111.10 (13)
C23—C13—C14	108.83 (13)	C22—N1—C1	115.52 (14)
C12—C13—C14	111.11 (13)	C15—N1—C1	105.67 (13)
C1—C13—C14	102.70 (13)	C11—O1—C12	116.96 (12)
C16—C14—C15	117.01 (15)	C23—O2—C24	116.95 (16)

N1—C1—C2—C11	−94.11 (18)	C12—C13—C14—C16	37.3 (2)
C13—C1—C2—C11	19.7 (2)	C1—C13—C14—C16	152.89 (14)
N1—C1—C2—C3	88.72 (18)	C23—C13—C14—C15	147.21 (14)
C13—C1—C2—C3	−157.44 (15)	C12—C13—C14—C15	−91.41 (16)
C11—C2—C3—C4	−173.26 (16)	C1—C13—C14—C15	24.21 (16)
C1—C2—C3—C4	4.0 (2)	C16—C14—C15—N1	−125.38 (15)
C11—C2—C3—C8	4.7 (2)	C13—C14—C15—N1	2.14 (18)
C1—C2—C3—C8	−178.13 (15)	C15—C14—C16—C17	−143.63 (18)
C8—C3—C4—C5	1.5 (3)	C13—C14—C16—C17	94.9 (2)
C2—C3—C4—C5	179.42 (16)	C15—C14—C16—C21	37.0 (2)
C3—C4—C5—C6	0.3 (3)	C13—C14—C16—C21	−84.4 (2)
C4—C5—C6—C7	−1.5 (3)	C21—C16—C17—C18	0.5 (3)
C5—C6—C7—C8	0.7 (3)	C14—C16—C17—C18	−178.94 (19)
C6—C7—C8—C9	−177.30 (18)	C16—C17—C18—C19	−0.3 (3)
C6—C7—C8—C3	1.1 (3)	C17—C18—C19—C20	0.2 (3)
C4—C3—C8—C9	176.27 (16)	C17—C18—C19—Br1	−178.80 (16)
C2—C3—C8—C9	−1.8 (2)	C18—C19—C20—C21	−0.2 (3)
C4—C3—C8—C7	−2.1 (2)	Br1—C19—C20—C21	178.80 (13)
C2—C3—C8—C7	179.83 (16)	C19—C20—C21—C16	0.3 (3)
C7—C8—C9—C10	176.89 (18)	C17—C16—C21—C20	−0.5 (3)
C3—C8—C9—C10	−1.5 (3)	C14—C16—C21—C20	178.91 (16)
C8—C9—C10—C11	1.8 (3)	C12—C13—C23—O3	−37.5 (2)
C3—C2—C11—O1	173.77 (15)	C1—C13—C23—O3	−160.58 (17)
C1—C2—C11—O1	−3.5 (3)	C14—C13—C23—O3	84.5 (2)
C3—C2—C11—C10	−4.5 (3)	C12—C13—C23—O2	145.27 (15)
C1—C2—C11—C10	178.16 (16)	C1—C13—C23—O2	22.1 (2)
C9—C10—C11—O1	−177.08 (17)	C14—C13—C23—O2	−92.74 (17)
C9—C10—C11—C2	1.4 (3)	C14—C15—N1—C22	−155.30 (15)
O1—C12—C13—C23	−67.90 (18)	C14—C15—N1—C1	−29.30 (18)
O1—C12—C13—C1	59.38 (18)	C2—C1—N1—C22	−72.26 (17)
O1—C12—C13—C14	171.46 (13)	C13—C1—N1—C22	167.70 (13)
N1—C1—C13—C23	−160.07 (13)	C2—C1—N1—C15	164.50 (13)
C2—C1—C13—C23	78.49 (17)	C13—C1—N1—C15	44.46 (15)
N1—C1—C13—C12	75.89 (15)	C2—C11—O1—C12	16.4 (2)
C2—C1—C13—C12	−45.55 (18)	C10—C11—O1—C12	−165.22 (16)
N1—C1—C13—C14	−41.73 (14)	C13—C12—O1—C11	−45.0 (2)
C2—C1—C13—C14	−163.17 (13)	O3—C23—O2—C24	0.2 (3)
C23—C13—C14—C16	−84.11 (17)	C13—C23—O2—C24	177.54 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24A···Br1ⁱ	0.96	2.84	3.789 (3)	172
C20—H20···Cg1ⁱⁱ	0.93	2.77	3.653 (2)	160

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂BrNO₃
M_r	452.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.7856 (4), 19.9348 (6), 8.0189 (3)
β (°)	106.163 (2)
V (Å³)	1963.06 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.12
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.619, 0.742
No. of measured, independent and observed [I > 2σ(I)] reflections	49847, 6162, 4068
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.722

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.02
No. of reflections	6162
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.51

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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
C24—H24A···Br1ⁱ	0.96	2.84	3.789 (3)	172
C20—H20···Cg1ⁱⁱ	0.93	2.77	3.653 (2)	160

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) −x+1, −y, −z+2.

Acknowledgements

SN thanks Dr Babu Vargheese, SAIF, IIT Madras, India, for his help with the data collection and SRM management, India, for their support.

References

Biava, M., Porretta, G. C., Poce, G., Deidda, D., Pompei, R., Tafi, A. & Manetti, F. (2005). Bioorg. Med. Chem. 13, 1221–1230. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 65| Part 8| August 2009| Pages o2028-o2029

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 3-(4-bromo­phen­yl)-1-methyl-1,2,3,3a,4,9b-hexa­hydro­benzo[f]chromeno[4,3-b]pyrrole-3a-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 3-(4-bromophenyl)-1-methyl-1,2,3,3a,4,9b-hexahydrobenzo[f]chromeno[4,3-b]pyrrole-3a-carboxylate