(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino-meth-yl]phenyl 4-bromo-benzene-sulfonate.

In the title compound, C(24)H(20)BrN(3)O(4)S, the central benzene ring makes dihedral angles of 17.13 (13), 39.83 (13) and 58.37 (13)°, respectively, with the pyrazolone ring, the bromo-benzene ring and the terminal phenyl ring. In the crystal structure, the packing is stabilized by a weak non-classical inter-molecular C-H⋯O hydrogen bond which links the mol-ecules into a chain propagating in [100].

Related literature

For a related structure, see: Han et al. (2007 ▶). For general background, see: Kahwa et al. (1986 ▶); Klayman et al. (1979 ▶); Santos et al. (2001 ▶). For reference geometrical data: see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H20BrN3O4S

M = 526.40

Monoclinic,

a = 6.9959 (14) Å

b = 33.222 (6) Å

c = 10.218 (2) Å

β = 95.992 (3)°

V = 2361.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.86 mm−1

T = 294 (2) K

0.18 × 0.16 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.693, T max = 0.815

12151 measured reflections

4174 independent reflections

2506 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.107

S = 1.01

4174 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035034/hb2828sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035034/hb2828Isup2.hkl

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

C24H20BrN3O4S	F(000) = 1072
Mr = 526.40	Dx = 1.480 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1963 reflections
a = 6.9959 (14) Å	θ = 2.9–25.2°
b = 33.222 (6) Å	µ = 1.86 mm−1
c = 10.218 (2) Å	T = 294 K
β = 95.992 (3)°	Block, yellow
V = 2361.9 (8) Å3	0.18 × 0.16 × 0.11 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4174 independent reflections
Radiation source: fine-focus sealed tube	2506 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.693, Tmax = 0.815	k = −39→27
12151 measured reflections	l = −12→10

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0386P)2 + 1.1353P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4174 reflections	Δρmax = 0.28 e Å−3
300 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (5)

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 > 2σ(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	−0.44278 (7)	0.221319 (15)	−0.16276 (5)	0.0730 (2)
S1	0.32046 (15)	0.32822 (3)	−0.18138 (10)	0.0519 (3)
N1	0.0354 (4)	0.49730 (9)	0.2384 (3)	0.0428 (8)
N2	−0.1008 (4)	0.56730 (9)	0.4793 (3)	0.0424 (8)
N3	0.0680 (4)	0.58680 (9)	0.4468 (3)	0.0413 (8)
O1	0.4033 (4)	0.31657 (9)	−0.2973 (3)	0.0710 (9)
O2	0.4292 (4)	0.32724 (8)	−0.0550 (3)	0.0649 (8)
O3	0.2468 (4)	0.37319 (7)	−0.2123 (2)	0.0557 (7)
O4	0.3126 (3)	0.57085 (8)	0.3161 (3)	0.0523 (7)
C1	0.0241 (6)	0.29604 (12)	−0.0562 (4)	0.0516 (10)
H1	0.0806	0.3080	0.0206	0.062*
C2	−0.1397 (6)	0.27304 (12)	−0.0533 (4)	0.0580 (11)
H2	−0.1926	0.2694	0.0257	0.070*
C3	−0.2254 (6)	0.25539 (12)	−0.1669 (4)	0.0515 (10)
C4	−0.1490 (7)	0.26142 (13)	−0.2856 (4)	0.0638 (12)
H4	−0.2087	0.2502	−0.3626	0.077*
C5	0.0158 (6)	0.28417 (13)	−0.2892 (4)	0.0590 (11)
H5	0.0674	0.2880	−0.3685	0.071*
C6	0.1050 (5)	0.30142 (11)	−0.1744 (3)	0.0421 (9)
C7	0.2344 (6)	0.40100 (11)	−0.1067 (4)	0.0450 (10)
C8	0.0584 (6)	0.40745 (11)	−0.0611 (4)	0.0470 (10)
H8	−0.0479	0.3923	−0.0935	0.056*
C9	0.0417 (5)	0.43669 (11)	0.0336 (4)	0.0471 (10)
H9	−0.0766	0.4412	0.0649	0.057*
C10	0.2019 (5)	0.45956 (11)	0.0826 (4)	0.0429 (9)
C11	0.3780 (5)	0.45208 (12)	0.0337 (4)	0.0534 (11)
H11	0.4856	0.4670	0.0653	0.064*
C12	0.3946 (6)	0.42264 (12)	−0.0617 (4)	0.0549 (11)
H12	0.5119	0.4178	−0.0941	0.066*
C13	0.1877 (5)	0.49231 (11)	0.1787 (4)	0.0463 (10)
H13	0.2908	0.5098	0.1967	0.056*
C14	0.0223 (5)	0.52968 (10)	0.3248 (3)	0.0373 (9)
C15	0.1548 (5)	0.56282 (11)	0.3545 (3)	0.0384 (9)
C16	−0.1307 (5)	0.53488 (11)	0.3982 (4)	0.0395 (9)
C17	−0.3093 (5)	0.50989 (12)	0.3944 (4)	0.0570 (11)
H17A	−0.4194	0.5264	0.3685	0.086*
H17B	−0.3201	0.4988	0.4801	0.086*
H17C	−0.3031	0.4884	0.3322	0.086*
C18	−0.2542 (5)	0.59204 (12)	0.5268 (4)	0.0584 (12)
H18A	−0.3351	0.6026	0.4530	0.088*
H18B	−0.1979	0.6139	0.5788	0.088*
H18C	−0.3297	0.5758	0.5796	0.088*
C19	0.1734 (5)	0.61215 (11)	0.5422 (4)	0.0405 (9)
C20	0.2802 (5)	0.64372 (12)	0.4972 (4)	0.0512 (10)
H20	0.2788	0.6486	0.4075	0.061*
C21	0.3887 (6)	0.66770 (13)	0.5880 (5)	0.0652 (12)
H21	0.4630	0.6884	0.5586	0.078*
C22	0.3878 (7)	0.66132 (14)	0.7211 (5)	0.0707 (13)
H22	0.4591	0.6778	0.7814	0.085*
C23	0.2799 (7)	0.63016 (14)	0.7642 (5)	0.0719 (13)
H23	0.2789	0.6258	0.8540	0.086*
C24	0.1737 (6)	0.60533 (12)	0.6761 (4)	0.0568 (11)
H24	0.1028	0.5842	0.7063	0.068*

	U11	U22	U33	U12	U13	U23
Br1	0.0799 (4)	0.0750 (4)	0.0635 (3)	−0.0191 (3)	0.0040 (2)	0.0108 (2)
S1	0.0520 (7)	0.0551 (7)	0.0491 (7)	0.0086 (5)	0.0076 (5)	−0.0027 (5)
N1	0.0394 (19)	0.0448 (19)	0.044 (2)	0.0047 (14)	0.0013 (16)	0.0025 (15)
N2	0.0279 (17)	0.051 (2)	0.050 (2)	0.0043 (15)	0.0134 (14)	0.0036 (16)
N3	0.0293 (17)	0.048 (2)	0.048 (2)	−0.0008 (14)	0.0101 (15)	0.0016 (15)
O1	0.068 (2)	0.076 (2)	0.075 (2)	0.0053 (16)	0.0348 (17)	−0.0107 (16)
O2	0.0584 (18)	0.069 (2)	0.063 (2)	0.0112 (15)	−0.0128 (15)	0.0004 (15)
O3	0.080 (2)	0.0478 (17)	0.0394 (17)	0.0059 (14)	0.0052 (14)	0.0025 (13)
O4	0.0341 (15)	0.0641 (18)	0.0611 (19)	−0.0074 (13)	0.0166 (13)	−0.0066 (14)
C1	0.063 (3)	0.058 (3)	0.033 (2)	0.007 (2)	0.003 (2)	−0.0026 (18)
C2	0.072 (3)	0.071 (3)	0.033 (2)	−0.001 (2)	0.015 (2)	0.003 (2)
C3	0.056 (3)	0.050 (3)	0.048 (3)	0.008 (2)	0.000 (2)	0.0074 (19)
C4	0.077 (3)	0.076 (3)	0.037 (3)	−0.013 (3)	−0.003 (2)	−0.004 (2)
C5	0.069 (3)	0.075 (3)	0.033 (2)	−0.004 (2)	0.008 (2)	0.000 (2)
C6	0.049 (2)	0.044 (2)	0.033 (2)	0.0098 (18)	0.0056 (18)	0.0027 (17)
C7	0.054 (3)	0.040 (2)	0.041 (2)	0.002 (2)	0.008 (2)	0.0055 (18)
C8	0.047 (2)	0.053 (3)	0.041 (2)	−0.0049 (19)	−0.0005 (19)	0.0059 (19)
C9	0.046 (2)	0.050 (2)	0.047 (2)	0.006 (2)	0.0109 (19)	0.005 (2)
C10	0.043 (2)	0.040 (2)	0.046 (2)	0.0046 (18)	0.0061 (19)	0.0056 (18)
C11	0.044 (2)	0.054 (3)	0.064 (3)	−0.009 (2)	0.009 (2)	−0.006 (2)
C12	0.046 (3)	0.055 (3)	0.066 (3)	0.003 (2)	0.015 (2)	−0.001 (2)
C13	0.039 (2)	0.050 (2)	0.051 (3)	0.0012 (18)	0.007 (2)	0.0028 (19)
C14	0.030 (2)	0.041 (2)	0.041 (2)	0.0020 (17)	0.0004 (17)	0.0061 (17)
C15	0.030 (2)	0.046 (2)	0.039 (2)	0.0096 (18)	0.0053 (17)	0.0072 (17)
C16	0.029 (2)	0.042 (2)	0.047 (2)	0.0031 (17)	0.0022 (18)	0.0102 (18)
C17	0.037 (2)	0.063 (3)	0.072 (3)	−0.003 (2)	0.008 (2)	0.005 (2)
C18	0.038 (2)	0.075 (3)	0.065 (3)	0.011 (2)	0.018 (2)	0.002 (2)
C19	0.035 (2)	0.038 (2)	0.049 (3)	0.0077 (17)	0.0058 (18)	0.0037 (18)
C20	0.053 (3)	0.053 (3)	0.049 (3)	0.007 (2)	0.011 (2)	0.003 (2)
C21	0.064 (3)	0.054 (3)	0.078 (4)	−0.015 (2)	0.010 (3)	−0.004 (2)
C22	0.076 (3)	0.066 (3)	0.068 (4)	−0.017 (3)	−0.003 (3)	−0.014 (3)
C23	0.091 (4)	0.075 (3)	0.047 (3)	−0.007 (3)	−0.003 (3)	−0.002 (2)
C24	0.062 (3)	0.056 (3)	0.051 (3)	−0.006 (2)	0.003 (2)	0.007 (2)

Br1—C3	1.900 (4)	C9—C10	1.403 (5)
S1—O1	1.425 (3)	C9—H9	0.9300
S1—O2	1.429 (3)	C10—C11	1.399 (5)
S1—O3	1.601 (3)	C10—C13	1.475 (5)
S1—C6	1.758 (4)	C11—C12	1.394 (5)
N1—C13	1.292 (4)	C11—H11	0.9300
N1—C14	1.401 (4)	C12—H12	0.9300
N2—C16	1.362 (4)	C13—H13	0.9300
N2—N3	1.416 (4)	C14—C16	1.380 (5)
N2—C18	1.474 (4)	C14—C15	1.451 (5)
N3—C15	1.418 (4)	C16—C17	1.497 (5)
N3—C19	1.433 (5)	C17—H17A	0.9600
O3—C7	1.430 (4)	C17—H17B	0.9600
O4—C15	1.239 (4)	C17—H17C	0.9600
C1—C2	1.380 (5)	C18—H18A	0.9600
C1—C6	1.398 (5)	C18—H18B	0.9600
C1—H1	0.9300	C18—H18C	0.9600
C2—C3	1.381 (5)	C19—C24	1.386 (5)
C2—H2	0.9300	C19—C20	1.394 (5)
C3—C4	1.390 (5)	C20—C21	1.387 (6)
C4—C5	1.382 (6)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.378 (6)
C5—C6	1.393 (5)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.380 (6)
C7—C12	1.370 (5)	C22—H22	0.9300
C7—C8	1.378 (5)	C23—C24	1.380 (6)
C8—C9	1.385 (5)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300
O1—S1—O2	121.36 (18)	C10—C11—H11	119.5
O1—S1—O3	103.89 (16)	C7—C12—C11	118.5 (4)
O2—S1—O3	109.24 (15)	C7—C12—H12	120.7
O1—S1—C6	108.71 (18)	C11—C12—H12	120.7
O2—S1—C6	109.24 (17)	N1—C13—C10	121.7 (3)
O3—S1—C6	102.77 (16)	N1—C13—H13	119.2
C13—N1—C14	120.5 (3)	C10—C13—H13	119.2
C16—N2—N3	107.3 (3)	C16—C14—N1	123.0 (3)
C16—N2—C18	124.8 (3)	C16—C14—C15	107.8 (3)
N3—N2—C18	118.4 (3)	N1—C14—C15	129.2 (3)
N2—N3—C15	108.9 (3)	O4—C15—N3	123.2 (3)
N2—N3—C19	119.4 (3)	O4—C15—C14	131.9 (3)
C15—N3—C19	123.9 (3)	N3—C15—C14	104.9 (3)
C7—O3—S1	119.9 (2)	N2—C16—C14	110.5 (3)
C2—C1—C6	120.1 (4)	N2—C16—C17	121.9 (3)
C2—C1—H1	120.0	C14—C16—C17	127.5 (4)
C6—C1—H1	120.0	C16—C17—H17A	109.5
C1—C2—C3	120.4 (4)	C16—C17—H17B	109.5
C1—C2—H2	119.8	H17A—C17—H17B	109.5
C3—C2—H2	119.8	C16—C17—H17C	109.5
C2—C3—C4	120.0 (4)	H17A—C17—H17C	109.5
C2—C3—Br1	120.8 (3)	H17B—C17—H17C	109.5
C4—C3—Br1	119.1 (3)	N2—C18—H18A	109.5
C5—C4—C3	119.9 (4)	N2—C18—H18B	109.5
C5—C4—H4	120.0	H18A—C18—H18B	109.5
C3—C4—H4	120.0	N2—C18—H18C	109.5
C4—C5—C6	120.3 (4)	H18A—C18—H18C	109.5
C4—C5—H5	119.8	H18B—C18—H18C	109.5
C6—C5—H5	119.8	C24—C19—C20	120.2 (4)
C5—C6—C1	119.2 (4)	C24—C19—N3	121.5 (3)
C5—C6—S1	119.0 (3)	C20—C19—N3	118.2 (3)
C1—C6—S1	121.7 (3)	C21—C20—C19	119.1 (4)
C12—C7—C8	122.2 (4)	C21—C20—H20	120.5
C12—C7—O3	118.7 (3)	C19—C20—H20	120.5
C8—C7—O3	118.9 (4)	C22—C21—C20	120.9 (4)
C7—C8—C9	119.3 (4)	C22—C21—H21	119.5
C7—C8—H8	120.3	C20—C21—H21	119.5
C9—C8—H8	120.3	C21—C22—C23	119.3 (4)
C8—C9—C10	120.5 (4)	C21—C22—H22	120.4
C8—C9—H9	119.8	C23—C22—H22	120.4
C10—C9—H9	119.8	C24—C23—C22	121.1 (4)
C11—C10—C9	118.5 (4)	C24—C23—H23	119.5
C11—C10—C13	119.5 (3)	C22—C23—H23	119.5
C9—C10—C13	122.0 (3)	C23—C24—C19	119.4 (4)
C12—C11—C10	121.0 (4)	C23—C24—H24	120.3
C12—C11—H11	119.5	C19—C24—H24	120.3
C16—N2—N3—C15	−7.1 (4)	C10—C11—C12—C7	−0.1 (6)
C18—N2—N3—C15	−155.2 (3)	C14—N1—C13—C10	−177.2 (3)
C16—N2—N3—C19	−157.5 (3)	C11—C10—C13—N1	−171.6 (3)
C18—N2—N3—C19	54.4 (4)	C9—C10—C13—N1	11.5 (6)
O1—S1—O3—C7	−152.2 (3)	C13—N1—C14—C16	−175.3 (3)
O2—S1—O3—C7	−21.4 (3)	C13—N1—C14—C15	5.1 (6)
C6—S1—O3—C7	94.5 (3)	N2—N3—C15—O4	−174.2 (3)
C6—C1—C2—C3	−0.4 (6)	C19—N3—C15—O4	−25.4 (5)
C1—C2—C3—C4	−1.3 (6)	N2—N3—C15—C14	4.5 (4)
C1—C2—C3—Br1	176.6 (3)	C19—N3—C15—C14	153.3 (3)
C2—C3—C4—C5	1.8 (6)	C16—C14—C15—O4	178.2 (4)
Br1—C3—C4—C5	−176.2 (3)	N1—C14—C15—O4	−2.2 (6)
C3—C4—C5—C6	−0.6 (7)	C16—C14—C15—N3	−0.4 (4)
C4—C5—C6—C1	−1.1 (6)	N1—C14—C15—N3	179.2 (3)
C4—C5—C6—S1	177.1 (3)	N3—N2—C16—C14	6.9 (4)
C2—C1—C6—C5	1.6 (6)	C18—N2—C16—C14	152.4 (3)
C2—C1—C6—S1	−176.6 (3)	N3—N2—C16—C17	−172.9 (3)
O1—S1—C6—C5	−19.4 (4)	C18—N2—C16—C17	−27.4 (5)
O2—S1—C6—C5	−153.8 (3)	N1—C14—C16—N2	176.3 (3)
O3—S1—C6—C5	90.3 (3)	C15—C14—C16—N2	−4.0 (4)
O1—S1—C6—C1	158.8 (3)	N1—C14—C16—C17	−3.9 (6)
O2—S1—C6—C1	24.4 (4)	C15—C14—C16—C17	175.7 (3)
O3—S1—C6—C1	−91.5 (3)	N2—N3—C19—C24	29.2 (5)
S1—O3—C7—C12	86.2 (4)	C15—N3—C19—C24	−116.5 (4)
S1—O3—C7—C8	−99.0 (4)	N2—N3—C19—C20	−152.1 (3)
C12—C7—C8—C9	−0.1 (6)	C15—N3—C19—C20	62.2 (5)
O3—C7—C8—C9	−174.7 (3)	C24—C19—C20—C21	1.0 (5)
C7—C8—C9—C10	0.0 (6)	N3—C19—C20—C21	−177.7 (3)
C8—C9—C10—C11	0.0 (5)	C19—C20—C21—C22	−1.7 (6)
C8—C9—C10—C13	176.9 (3)	C20—C21—C22—C23	1.2 (7)
C9—C10—C11—C12	0.1 (6)	C21—C22—C23—C24	0.1 (7)
C13—C10—C11—C12	−177.0 (4)	C22—C23—C24—C19	−0.8 (7)
C8—C7—C12—C11	0.1 (6)	C20—C19—C24—C23	0.3 (6)
O3—C7—C12—C11	174.8 (3)	N3—C19—C24—C23	178.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O4i	0.96	2.40	3.361 (5)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O4i	0.96	2.40	3.361 (5)	176

Symmetry code: (i) .