3-[3-(4-Bromo-phen-yl)-1-phenyl-1H-pyrazol-4-yl]-5-eth-oxy-2-phenyl-isoxazolidine.

In the title compound, C(26)H(24)BrN(3)O(2), 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 = 490.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.00

4982 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064938/lw2049Isup2.hkl

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

C26H24BrN3O2	F000 = 2016
Mr = 490.39	Dx = 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 = 2.9–27.0º
b = 7.4254 (2) Å	µ = 1.82 mm−1
c = 24.5230 (5) Å	T = 293 (2) K
β = 114.516 (1)º	Cubic, yellow
V = 4597.41 (18) Å3	0.26 × 0.23 × 0.22 mm
Z = 8

Bruker Kappa APEXII diffractometer	4982 independent reflections
Radiation source: fine-focus sealed tube	3038 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 293(2) K	θmax = 27.0º
ω and φ scans	θmin = 2.9º
Absorption correction: multi-scan(SAINT; Bruker, 1999)	h = −35→35
Tmin = 0.650, Tmax = 0.691	k = −9→9
23867 measured reflections	l = −31→31

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0394P)2 + 2.7695P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max = 0.004
S = 1.00	Δρmax = 0.37 e Å−3
4982 reflections	Δρmin = −0.49 e Å−3
289 parameters	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (11)
Secondary atom site location: difference Fourier map

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
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*

	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)

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)