3-[3-(4-Bromo­phen­yl)-1-phenyl-1H-pyrazol-4-yl]-5-eth­oxy-2-phenyl­isoxazolidine

Etti, S.; Karthikeyan, K.; Shanmugam, G.; Perumal, P.T.

doi:10.1107/S1600536807064938

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o342

https://doi.org/10.1107/S1600536807064938

Open

access

3-[3-(4-Bromophenyl)-1-phenyl-1H-pyrazol-4-yl]-5-ethoxy-2-phenylisoxazolidine

S. Etti,^a K. Karthikeyan,^b G. Shanmugam ^a ^* and P. T. Perumal ^b

^aCentre for Advanced Studies in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India
^*Correspondence e-mail: gurushan48@yahoo.com

(Received 16 November 2007; accepted 1 December 2007; online 21 December 2007)

In the title compound, C₂₆H₂₄BrN₃O₂, the isoxazolidine ring adopts an envelope conformation, the ring N atom deviating from the mean plane of the other four atoms by an angle of 0.286°. The orientation of the phenyl ring is +sp and the bromophenyl ring is +sc relative to the attached pyrazole ring; the dihedral angles between the least-squares planes of the pyrazole and the attached phenyl and bromophenyl rings are 21.8 (3) and 41.8 (3)°.

Related literature

For related literature, see: Allen et al. (1987 ); Gayathri et al. (2007 ); Frederickson (1997 ); Gothelf et al. (2002 ); Huisgen (1984 ); Kumar et al. (2003 ).

Experimental

Crystal data

C₂₆H₂₄BrN₃O₂
M_r = 490.39
Monoclinic, C 2/c
a = 27.7493 (6) Å
b = 7.4254 (2) Å
c = 24.5230 (5) Å
β = 114.516 (1)°
V = 4597.41 (18) Å³
Z = 8
Mo Kα radiation
μ = 1.82 mm⁻¹
T = 293 (2) K
0.26 × 0.23 × 0.22 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SAINT; Bruker, 1999 ) T_min = 0.650, T_max = 0.691
23867 measured reflections
4982 independent reflections
3038 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.00
4982 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PARST97 (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807064938/lw2049sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064938/lw2049Isup2.hkl

checkCIF report

Comment top

The 1,3-dipolar cycloadditionof nitrones to alkenes provides a straight forward route to isoxazolidines(Frederickson, 1997, Gothelf et al., 2002). The nitrone cycloadducts are attractive intermediates for the synthesis of several class of natural products and biologically active compounds such as b-aminoacids and alkaloids.(Huisgen, 1984).The pyrazole unit is the core structure in a number of natural products. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as anti-hyperglycemic, analgesic, anti-inflammatory, anti-pyretic, anti-bacterial, hypoglycemic, sedative, hypnotic activity, and anticoagulant activity. Particularly, arylpyrazoles are widely used in medicinal and pesticidal chemistry. Recently some arylpyrazoles were reported to display non-nucleoside HIV-1 reverse transcriptase inhibitory activity (Kumar et al., 2003).

The isoxazolidine ring adopts envelope conformation with N as the flap, atom N7 deviates from the mean plane with a maximum deviation of 0.286 (2)°. The ethoxy group attached to the isoxazolidine adopts an extended conformation. The bond lengths and bond angles are comparable with literature values (Allen et al.,1987).The dihedral angle between the LSQ planes of pyrazole and phenyl and bromo phenyl ring is 21.8 (3)° and 41.8 (3)°, which is lower than the reported value due to the simple substitution of a bromine to the phenyl ring (Gayathri et al.,2007). The phenyl ring is equatorially substituted to the isoxazolidine ring and slightly twisted due to the steric hinderance with the bromophenyl ring and the ethoxy group is substituted axailly to the isoxazolidine ring. The molecule iss stabilized by intra molecular C—H···O hydrogen bonds in the unit cell.

Related literature top

For related literature, see: Allen et al. (1987); Gayathri et al. (2007); Frederickson (1997); Gothelf et al. (2002); Huisgen (1984); Kumar et al. (2003).

Experimental top

A solution of pyrazole nitrone (0.5 mmol) and ethyl vinyl ether (5 mmol) was refluxed in dry toluene (10 mL) at 60°C until the completion of the reaction as evidenced by thin-layer chromatography. The solvent was evaporated under reduced pressure. The crude was purified by column chromatography using ethyl acetate-petroleum ether (3:97) as eluent, to afford the pure isoxazolidine (68%) as a white solid. Single crystals were obtained by crystallization from petroleum ether and ethyl acetate mixture.

Structure description top

For related literature, see: Allen et al. (1987); Gayathri et al. (2007); Frederickson (1997); Gothelf et al. (2002); Huisgen (1984); Kumar et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PARST97 (Nardelli, 1995).

Figures top

	Fig. 1. The ORTEP diagram of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. Packing of the molecules viewed down c axis.

3-[3-(4-Bromophenyl)-1-phenyl-1H-pyrazol-4-yl]- 5-ethoxy-2-phenylisoxazolidine top

Crystal data top

C₂₆H₂₄BrN₃O₂	F(000) = 2016
M_r = 490.39	D_x = 1.417 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4982 reflections
a = 27.7493 (6) Å	θ = 2.9–27.0°
b = 7.4254 (2) Å	µ = 1.82 mm⁻¹
c = 24.5230 (5) Å	T = 293 K
β = 114.516 (1)°	Cubic, yellow
V = 4597.41 (18) Å³	0.26 × 0.23 × 0.22 mm
Z = 8

Data collection top

Bruker Kappa APEXII diffractometer	4982 independent reflections
Radiation source: fine-focus sealed tube	3038 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω and φ scans	θ_max = 27.0°, θ_min = 2.9°
Absorption correction: multi-scan (SAINT; Bruker, 1999)	h = −35→35
T_min = 0.650, T_max = 0.691	k = −9→9
23867 measured reflections	l = −31→31

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0394P)² + 2.7695P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.004
4982 reflections	Δρ_max = 0.37 e Å⁻³
289 parameters	Δρ_min = −0.49 e Å⁻³
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (11)

Crystal data top

C₂₆H₂₄BrN₃O₂	V = 4597.41 (18) Å³
M_r = 490.39	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.7493 (6) Å	µ = 1.82 mm⁻¹
b = 7.4254 (2) Å	T = 293 K
c = 24.5230 (5) Å	0.26 × 0.23 × 0.22 mm
β = 114.516 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	4982 independent reflections
Absorption correction: multi-scan (SAINT; Bruker, 1999)	3038 reflections with I > 2σ(I)
T_min = 0.650, T_max = 0.691	R_int = 0.041
23867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.00	Δρ_max = 0.37 e Å⁻³
4982 reflections	Δρ_min = −0.49 e Å⁻³
289 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
Br1	1.015166 (12)	0.61394 (5)	0.097949 (17)	0.09166 (16)
N1	0.76772 (7)	0.4888 (2)	0.08475 (8)	0.0420 (4)
N2	0.72795 (7)	0.4783 (2)	0.10324 (8)	0.0412 (4)
C3	0.74697 (9)	0.4845 (3)	0.16353 (10)	0.0436 (5)
H3	0.7268	0.4794	0.1857	0.052*
C4	0.80068 (9)	0.4996 (3)	0.18641 (9)	0.0388 (5)
C5	0.81190 (9)	0.5021 (3)	0.13506 (9)	0.0381 (5)
C11	0.67491 (9)	0.4517 (3)	0.06083 (10)	0.0419 (5)
C16	0.66488 (10)	0.3876 (3)	0.00433 (11)	0.0531 (6)
H7	0.6926	0.3660	−0.0067	0.064*
C15	0.61347 (11)	0.3559 (3)	−0.03539 (13)	0.0661 (7)
H8	0.6066	0.3131	−0.0736	0.079*
C14	0.57219 (11)	0.3861 (4)	−0.01980 (14)	0.0699 (8)
H9	0.5376	0.3615	−0.0468	0.084*
C13	0.58227 (10)	0.4529 (4)	0.03587 (14)	0.0650 (7)
H10	0.5543	0.4749	0.0465	0.078*
C12	0.63349 (10)	0.4881 (3)	0.07642 (11)	0.0524 (6)
H11	0.6400	0.5359	0.1139	0.063*
C6	0.83710 (9)	0.5082 (3)	0.25106 (9)	0.0400 (5)
H6	0.8732	0.5337	0.2555	0.048*
N7	0.83638 (7)	0.3344 (2)	0.28223 (7)	0.0396 (4)
O8	0.86261 (6)	0.3879 (2)	0.34526 (6)	0.0474 (4)
C9	0.83812 (9)	0.5532 (3)	0.34867 (10)	0.0446 (5)
H9A	0.8637	0.6299	0.3798	0.054*
C10	0.82134 (10)	0.6428 (3)	0.28798 (10)	0.0497 (6)
H10A	0.8396	0.7565	0.2916	0.060*
H10B	0.7834	0.6642	0.2698	0.060*
C17	0.86907 (9)	0.1977 (3)	0.27316 (10)	0.0412 (5)
C22	0.84549 (10)	0.0922 (3)	0.22259 (11)	0.0521 (6)
H18	0.8098	0.1067	0.1976	0.062*
C21	0.87546 (12)	−0.0354 (3)	0.20937 (13)	0.0642 (7)
H19	0.8600	−0.1039	0.1746	0.077*
C20	0.92747 (13)	−0.0614 (4)	0.24692 (15)	0.0718 (8)
H20	0.9473	−0.1480	0.2380	0.086*
C19	0.95026 (11)	0.0402 (4)	0.29764 (14)	0.0718 (8)
H21	0.9856	0.0217	0.3234	0.086*
C18	0.92128 (10)	0.1703 (3)	0.31106 (12)	0.0573 (6)
H22	0.9371	0.2391	0.3457	0.069*
O23	0.79337 (6)	0.5295 (2)	0.35987 (6)	0.0468 (4)
C24	0.80487 (10)	0.4624 (3)	0.41873 (10)	0.0504 (6)
H24A	0.8319	0.5358	0.4486	0.060*
H24B	0.8177	0.3395	0.4226	0.060*
C25	0.75456 (11)	0.4695 (4)	0.42755 (12)	0.0703 (8)
H25A	0.7610	0.4249	0.4667	0.106*
H25B	0.7281	0.3964	0.3977	0.106*
H25C	0.7423	0.5917	0.4238	0.106*
C26	0.86227 (9)	0.5288 (3)	0.12921 (9)	0.0387 (5)
C31	0.86189 (9)	0.6344 (3)	0.08219 (10)	0.0456 (5)
H27	0.8305	0.6888	0.0564	0.055*
C30	0.90731 (10)	0.6599 (3)	0.07315 (11)	0.0522 (6)
H28	0.9065	0.7291	0.0412	0.063*
C29	0.95350 (9)	0.5817 (3)	0.11189 (11)	0.0513 (6)
C28	0.95552 (10)	0.4791 (3)	0.15916 (11)	0.0544 (6)
H30	0.9873	0.4282	0.1854	0.065*
C27	0.90973 (9)	0.4523 (3)	0.16740 (10)	0.0463 (6)
H31	0.9108	0.3815	0.1992	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0616 (2)	0.1079 (3)	0.1308 (3)	0.00190 (17)	0.0650 (2)	0.0236 (2)
N1	0.0463 (11)	0.0463 (10)	0.0442 (11)	−0.0036 (9)	0.0296 (10)	−0.0001 (8)
N2	0.0440 (11)	0.0436 (10)	0.0436 (11)	−0.0031 (8)	0.0258 (9)	0.0021 (8)
C3	0.0515 (14)	0.0448 (12)	0.0477 (14)	−0.0017 (11)	0.0339 (12)	0.0042 (10)
C4	0.0502 (13)	0.0355 (11)	0.0404 (13)	0.0000 (10)	0.0285 (11)	0.0015 (9)
C5	0.0443 (13)	0.0354 (11)	0.0412 (13)	0.0000 (10)	0.0244 (11)	−0.0008 (9)
C11	0.0444 (13)	0.0365 (11)	0.0470 (14)	−0.0043 (10)	0.0211 (11)	0.0043 (10)
C16	0.0518 (15)	0.0544 (14)	0.0553 (16)	−0.0006 (12)	0.0246 (13)	−0.0019 (12)
C15	0.0646 (18)	0.0661 (17)	0.0582 (17)	−0.0037 (14)	0.0160 (15)	−0.0105 (13)
C14	0.0498 (16)	0.0674 (17)	0.080 (2)	−0.0050 (14)	0.0147 (15)	0.0006 (15)
C13	0.0474 (16)	0.0686 (17)	0.085 (2)	0.0019 (13)	0.0329 (16)	0.0117 (15)
C12	0.0518 (15)	0.0547 (14)	0.0589 (15)	−0.0013 (12)	0.0311 (13)	0.0020 (12)
C6	0.0496 (13)	0.0389 (11)	0.0418 (13)	−0.0025 (10)	0.0291 (11)	−0.0011 (10)
N7	0.0501 (11)	0.0415 (9)	0.0329 (10)	0.0028 (8)	0.0231 (9)	0.0001 (8)
O8	0.0559 (10)	0.0548 (9)	0.0356 (9)	0.0104 (8)	0.0229 (8)	−0.0017 (7)
C9	0.0498 (14)	0.0482 (13)	0.0425 (13)	−0.0005 (11)	0.0258 (11)	−0.0080 (10)
C10	0.0710 (16)	0.0422 (12)	0.0487 (14)	0.0039 (11)	0.0377 (13)	0.0000 (10)
C17	0.0507 (14)	0.0369 (11)	0.0472 (13)	0.0000 (10)	0.0314 (12)	0.0036 (10)
C22	0.0604 (15)	0.0440 (13)	0.0570 (16)	−0.0029 (11)	0.0296 (13)	−0.0065 (11)
C21	0.081 (2)	0.0482 (14)	0.0740 (19)	−0.0064 (14)	0.0422 (17)	−0.0176 (13)
C20	0.080 (2)	0.0531 (16)	0.100 (2)	0.0077 (15)	0.055 (2)	−0.0111 (16)
C19	0.0570 (17)	0.0723 (18)	0.086 (2)	0.0146 (15)	0.0292 (16)	−0.0078 (17)
C18	0.0571 (16)	0.0554 (14)	0.0623 (17)	0.0067 (12)	0.0276 (14)	−0.0070 (12)
O23	0.0522 (10)	0.0572 (9)	0.0387 (9)	0.0068 (8)	0.0266 (8)	0.0029 (7)
C24	0.0676 (16)	0.0511 (13)	0.0409 (13)	0.0092 (12)	0.0310 (12)	0.0044 (11)
C25	0.080 (2)	0.0892 (19)	0.0590 (17)	0.0074 (16)	0.0456 (16)	0.0151 (15)
C26	0.0464 (13)	0.0383 (11)	0.0402 (12)	−0.0014 (10)	0.0268 (11)	−0.0049 (10)
C31	0.0464 (13)	0.0485 (13)	0.0481 (14)	0.0030 (11)	0.0259 (11)	0.0058 (11)
C30	0.0579 (16)	0.0517 (14)	0.0611 (16)	−0.0013 (12)	0.0388 (14)	0.0091 (12)
C29	0.0469 (14)	0.0543 (14)	0.0665 (16)	−0.0033 (12)	0.0372 (13)	−0.0011 (12)
C28	0.0444 (14)	0.0663 (16)	0.0545 (16)	0.0064 (12)	0.0224 (13)	0.0017 (13)
C27	0.0536 (15)	0.0515 (13)	0.0419 (13)	0.0042 (11)	0.0277 (12)	0.0037 (10)

Geometric parameters (Å, º) top

Br1—C29	1.894 (2)	C10—H10A	0.9700
N1—C5	1.334 (3)	C10—H10B	0.9700
N1—N2	1.358 (2)	C17—C18	1.374 (3)
N2—C3	1.349 (3)	C17—C22	1.381 (3)
N2—C11	1.420 (3)	C22—C21	1.385 (3)
C3—C4	1.362 (3)	C22—H18	0.9300
C3—H3	0.9300	C21—C20	1.366 (4)
C4—C5	1.417 (3)	C21—H19	0.9300
C4—C6	1.486 (3)	C20—C19	1.365 (4)
C5—C26	1.476 (3)	C20—H20	0.9300
C11—C16	1.380 (3)	C19—C18	1.381 (3)
C11—C12	1.380 (3)	C19—H21	0.9300
C16—C15	1.373 (4)	C18—H22	0.9300
C16—H7	0.9300	O23—C24	1.432 (2)
C15—C14	1.369 (4)	C24—C25	1.500 (3)
C15—H8	0.9300	C24—H24A	0.9700
C14—C13	1.368 (4)	C24—H24B	0.9700
C14—H9	0.9300	C25—H25A	0.9600
C13—C12	1.380 (3)	C25—H25B	0.9600
C13—H10	0.9300	C25—H25C	0.9600
C12—H11	0.9300	C26—C27	1.382 (3)
C6—N7	1.504 (3)	C26—C31	1.391 (3)
C6—C10	1.529 (3)	C31—C30	1.380 (3)
C6—H6	0.9800	C31—H27	0.9300
N7—C17	1.439 (3)	C30—C29	1.368 (3)
N7—O8	1.464 (2)	C30—H28	0.9300
O8—C9	1.422 (3)	C29—C28	1.369 (3)
C9—O23	1.390 (2)	C28—C27	1.381 (3)
C9—C10	1.516 (3)	C28—H30	0.9300
C9—H9A	0.9800	C27—H31	0.9300

C5—N1—N2	104.94 (16)	C6—C10—H10B	110.9
C3—N2—N1	111.19 (17)	H10A—C10—H10B	108.9
C3—N2—C11	128.51 (17)	C18—C17—C22	119.8 (2)
N1—N2—C11	120.16 (17)	C18—C17—N7	123.8 (2)
N2—C3—C4	108.54 (17)	C22—C17—N7	116.4 (2)
N2—C3—H3	125.7	C17—C22—C21	119.4 (2)
C4—C3—H3	125.7	C17—C22—H18	120.3
C3—C4—C5	103.97 (18)	C21—C22—H18	120.3
C3—C4—C6	125.90 (18)	C20—C21—C22	120.5 (3)
C5—C4—C6	130.13 (19)	C20—C21—H19	119.7
N1—C5—C4	111.36 (18)	C22—C21—H19	119.7
N1—C5—C26	117.65 (17)	C19—C20—C21	119.8 (2)
C4—C5—C26	130.8 (2)	C19—C20—H20	120.1
C16—C11—C12	120.1 (2)	C21—C20—H20	120.1
C16—C11—N2	119.9 (2)	C20—C19—C18	120.5 (3)
C12—C11—N2	119.9 (2)	C20—C19—H21	119.7
C15—C16—C11	119.3 (2)	C18—C19—H21	119.7
C15—C16—H7	120.4	C17—C18—C19	119.8 (2)
C11—C16—H7	120.4	C17—C18—H22	120.1
C14—C15—C16	121.2 (3)	C19—C18—H22	120.1
C14—C15—H8	119.4	C9—O23—C24	113.54 (17)
C16—C15—H8	119.4	O23—C24—C25	107.5 (2)
C13—C14—C15	119.3 (3)	O23—C24—H24A	110.2
C13—C14—H9	120.3	C25—C24—H24A	110.2
C15—C14—H9	120.3	O23—C24—H24B	110.2
C14—C13—C12	120.7 (2)	C25—C24—H24B	110.2
C14—C13—H10	119.6	H24A—C24—H24B	108.5
C12—C13—H10	119.6	C24—C25—H25A	109.5
C13—C12—C11	119.4 (2)	C24—C25—H25B	109.5
C13—C12—H11	120.3	H25A—C25—H25B	109.5
C11—C12—H11	120.3	C24—C25—H25C	109.5
C4—C6—N7	111.02 (16)	H25A—C25—H25C	109.5
C4—C6—C10	115.13 (18)	H25B—C25—H25C	109.5
N7—C6—C10	101.09 (15)	C27—C26—C31	118.09 (19)
C4—C6—H6	109.8	C27—C26—C5	123.58 (19)
N7—C6—H6	109.8	C31—C26—C5	118.3 (2)
C10—C6—H6	109.8	C30—C31—C26	121.1 (2)
C17—N7—O8	106.59 (15)	C30—C31—H27	119.4
C17—N7—C6	112.61 (15)	C26—C31—H27	119.4
O8—N7—C6	101.43 (14)	C29—C30—C31	119.0 (2)
C9—O8—N7	104.82 (14)	C29—C30—H28	120.5
O23—C9—O8	112.99 (18)	C31—C30—H28	120.5
O23—C9—C10	108.29 (19)	C30—C29—C28	121.4 (2)
O8—C9—C10	106.28 (16)	C30—C29—Br1	118.51 (17)
O23—C9—H9A	109.7	C28—C29—Br1	120.05 (19)
O8—C9—H9A	109.7	C29—C28—C27	119.2 (2)
C10—C9—H9A	109.7	C29—C28—H30	120.4
C9—C10—C6	104.34 (17)	C27—C28—H30	120.4
C9—C10—H10A	110.9	C28—C27—C26	121.1 (2)
C6—C10—H10A	110.9	C28—C27—H31	119.4
C9—C10—H10B	110.9	C26—C27—H31	119.4

C5—N1—N2—C3	−0.1 (2)	N7—O8—C9—C10	−29.9 (2)
C5—N1—N2—C11	−176.21 (17)	O23—C9—C10—C6	−119.66 (19)
N1—N2—C3—C4	0.0 (2)	O8—C9—C10—C6	2.0 (2)
C11—N2—C3—C4	175.68 (19)	C4—C6—C10—C9	145.05 (18)
N2—C3—C4—C5	0.1 (2)	N7—C6—C10—C9	25.3 (2)
N2—C3—C4—C6	−179.11 (18)	O8—N7—C17—C18	−18.5 (3)
N2—N1—C5—C4	0.2 (2)	C6—N7—C17—C18	91.9 (2)
N2—N1—C5—C26	−175.78 (17)	O8—N7—C17—C22	162.37 (17)
C3—C4—C5—N1	−0.2 (2)	C6—N7—C17—C22	−87.3 (2)
C6—C4—C5—N1	178.98 (19)	C18—C17—C22—C21	−2.7 (3)
C3—C4—C5—C26	175.1 (2)	N7—C17—C22—C21	176.5 (2)
C6—C4—C5—C26	−5.7 (4)	C17—C22—C21—C20	2.2 (4)
C3—N2—C11—C16	−157.4 (2)	C22—C21—C20—C19	−0.5 (4)
N1—N2—C11—C16	17.9 (3)	C21—C20—C19—C18	−0.6 (4)
C3—N2—C11—C12	21.8 (3)	C22—C17—C18—C19	1.6 (4)
N1—N2—C11—C12	−162.82 (19)	N7—C17—C18—C19	−177.5 (2)
C12—C11—C16—C15	−1.8 (3)	C20—C19—C18—C17	0.1 (4)
N2—C11—C16—C15	177.5 (2)	O8—C9—O23—C24	68.5 (2)
C11—C16—C15—C14	−0.3 (4)	C10—C9—O23—C24	−174.05 (17)
C16—C15—C14—C13	1.5 (4)	C9—O23—C24—C25	171.8 (2)
C15—C14—C13—C12	−0.7 (4)	N1—C5—C26—C27	−143.2 (2)
C14—C13—C12—C11	−1.4 (4)	C4—C5—C26—C27	41.8 (3)
C16—C11—C12—C13	2.6 (3)	N1—C5—C26—C31	35.7 (3)
N2—C11—C12—C13	−176.7 (2)	C4—C5—C26—C31	−139.3 (2)
C3—C4—C6—N7	65.4 (3)	C27—C26—C31—C30	1.1 (3)
C5—C4—C6—N7	−113.6 (2)	C5—C26—C31—C30	−177.9 (2)
C3—C4—C6—C10	−48.7 (3)	C26—C31—C30—C29	−1.0 (3)
C5—C4—C6—C10	132.3 (2)	C31—C30—C29—C28	0.1 (4)
C4—C6—N7—C17	80.7 (2)	C31—C30—C29—Br1	178.75 (17)
C10—C6—N7—C17	−156.73 (18)	C30—C29—C28—C27	0.8 (4)
C4—C6—N7—O8	−165.78 (15)	Br1—C29—C28—C27	−177.84 (18)
C10—C6—N7—O8	−43.17 (19)	C29—C28—C27—C26	−0.8 (4)
C17—N7—O8—C9	164.37 (15)	C31—C26—C27—C28	−0.2 (3)
C6—N7—O8—C9	46.37 (17)	C5—C26—C27—C28	178.8 (2)
N7—O8—C9—O23	88.77 (19)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄BrN₃O₂
M_r	490.39
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	27.7493 (6), 7.4254 (2), 24.5230 (5)
β (°)	114.516 (1)
V (Å³)	4597.41 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.82
Crystal size (mm)	0.26 × 0.23 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SAINT; Bruker, 1999)
T_min, T_max	0.650, 0.691
No. of measured, independent and observed [I > 2σ(I)] reflections	23867, 4982, 3038
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.00
No. of reflections	4982
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.49

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997), PARST97 (Nardelli, 1995).

Acknowledgements

SE thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, for providing financial assistance as a Senior Research Fellowship (SRF).

References

Allen, F. H., Kennard, O., Watson, D., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, S1–19. CrossRef Google Scholar
Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Frederickson, M. (1997). Tetrahedron, 53, 403–425. CrossRef CAS Web of Science Google Scholar
Gayathri, D., Velmurugan, D., Ravikumar, K., Karthikeyan, K. & Perumal, P. T. (2007). Acta Cryst. E63, o2216–o2217. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gothelf, A. S., Gothelf, K. V., Hazell, R. G. & Jorgensen, K. A. (2002). Angew. Chem. Int. Ed. 41, 4236–4238. CrossRef CAS Google Scholar
Huisgen, R. (1984). 1–3-Dipolar Cycloaddition Chemistry, Vol. 1, edited by A. Padwa. New York: Wiley. Google Scholar
Kumar, K. R. R., Mallesha, H. & Rangappa, K. S. (2003). Eur. J. Med. Chem. 38, 613–619. Web of Science CrossRef PubMed Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.