(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­meth­yl]phenyl 4-bromo­benzene­sulfonate

Han, J.-R.; Tian, X.; Zhen, X.-L.; Li, Z.-C.; Liu, S.-X.

doi:10.1107/S1600536808035034

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2244

doi:10.1107/S1600536808035034

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(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]phenyl 4-bromobenzenesulfonate

Jian-Rong Han,^a ^* Xia Tian,^a Xiao-Li Zhen,^a Zhen-Chao Li ^a and Shou-Xin Liu ^b ‡

^aCollege of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China, and ^bCollege of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
^*Correspondence e-mail: han_jianrong@163.com

(Received 27 October 2008; accepted 28 October 2008; online 31 October 2008)

In the title compound, C₂₄H₂₀BrN₃O₄S, the central benzene ring makes dihedral angles of 17.13 (13), 39.83 (13) and 58.37 (13)°, respectively, with the pyrazolone ring, the bromobenzene ring and the terminal phenyl ring. In the crystal structure, the packing is stabilized by a weak non-classical intermolecular C—H⋯O hydrogen bond which links the molecules 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_r = 526.40
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.107
S = 1.01
4174 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) x-1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

The synthesis and structure of Schiff bases have attracted much attention in biology and chemistry (Kahwa et al., 1986; Klayman et al., 1979). Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). Among the large number of compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them, such as (E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino) methyl]-phenyl 4-chlorobenzoate (Han et al., 2007) has been reported.

As part of an investigation of the potential coordination properties of Schiff bases that could function as ligands, we now report the synthesis and structure of the title compound, (I).

In the title molecule (Fig. 1), the pyrazolone ring (C14—C16/N1/N2/N3/O4) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.029 Å. It makes a dihedral angle of 50.07 (13)° with its attached phenyl ring (C19—C24). The central benzene ring (C7—C13/O3) is almost planar, with an r.m.s. deviation for fitted atoms of 0.040Å. This group makes dihedral angles of 17.13 (13)°, 39.83 (13)° and 58.37 (13)°, respectively, with the the pyrazolone ring (C14—C16/N1/N2/N3/O4), the terminal C1—C6 benzene ring and the terminal C19—C24 phenyl ring. Otherwise, all bond lengths and angles are within their normal ranges (Allen et al., 1987).

In the crystal, the packing is stabilized by a weak, non-classical intermolecular C17—H17A···O4 hydrogen bond that links molecules into one-dimensional extended chains running along the a axis (Table 1, Fig. 2).

Related literature top

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 top

An anhydrous ethanol solution (50 ml) of 4-formylphenyl 4-bromobenzenesulfonate (3.41 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) and the mixture stirred at 350 K for 3 h under N₂, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile, and then dried in a vacuum to give pure compound (I) in 87% yield. Yellow blocks of (I) were obtained by slow evaporation of an acetonitrile solution.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. Packing diagram for (I), with H bonds drawn as dashed lines.

(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4- yl)iminomethyl]phenyl 4-bromobenzenesulfonate top

Crystal data top

C₂₄H₂₀BrN₃O₄S	F(000) = 1072
M_r = 526.40	D_x = 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

Data collection top

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

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0386P)² + 1.1353P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4174 reflections	Δρ_max = 0.28 e Å⁻³
300 parameters	Δρ_min = −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)

Crystal data top

C₂₄H₂₀BrN₃O₄S	V = 2361.9 (8) Å³
M_r = 526.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9959 (14) Å	µ = 1.86 mm⁻¹
b = 33.222 (6) Å	T = 294 K
c = 10.218 (2) Å	0.18 × 0.16 × 0.11 mm
β = 95.992 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4174 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2506 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.815	R_int = 0.058
12151 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.01	Δρ_max = 0.28 e Å⁻³
4174 reflections	Δρ_min = −0.23 e Å⁻³
300 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀BrN₃O₄S
M_r	526.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	6.9959 (14), 33.222 (6), 10.218 (2)
β (°)	95.992 (3)
V (Å³)	2361.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.18 × 0.16 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.693, 0.815
No. of measured, independent and observed [I > 2σ(I)] reflections	12151, 4174, 2506
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.107, 1.01
No. of reflections	4174
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.23

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Footnotes

‡Additional contact author, e-mail: liu_shouxin@163.com.

Acknowledgements

The project was supported by the Foundation of the Education Department of Hebei Province (grant No. 606022).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Han, J.-R., Zhen, X.-L., Tian, X., Li, F. & Liu, S.-X. (2007). Acta Cryst. E63, o4035. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Klayman, D. L., Bartosevich, J. F., Griffin, T. S., Mason, C. J. & Scovill, J. P. (1979). J. Med. Chem. 22, 855–862. CrossRef CAS PubMed Web of Science Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

(E)-4-[(1,5-Di­methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)imino­meth­yl]phenyl 4-bromo­benzene­sulfonate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]phenyl 4-bromobenzenesulfonate