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

Li, M.; Chen, X.

doi:10.1107/S160053680803688X

organic compounds

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Volume 64| Part 12| December 2008| Page o2349

doi:10.1107/S160053680803688X

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

Mei Li ^a ^* and Xin Chen ^a

^aCollege of Sciences, Tianjin University of Science and Technology, Tianjin 300457, People's Republic of China
^*Correspondence e-mail: li_mei999@163.com

(Received 29 October 2008; accepted 9 November 2008; online 13 November 2008)

In the title compound, C₂₄H₂₀BrN₃O₄S, the central benzene ring makes dihedral angles of 24.55 (8), 49.52 (12) and 59.65 (7)°, respectively, with the pyrazolone ring, the bromobenzene ring and the terminal phenyl ring. The packing is stabilized by weak non-classical intermolecular C—H⋯O=C hydrogen bonds that form inversion-related dimers.

Related literature

For general background to Schiff base ligands, see: Chen & Yu (2006 ); Kahwa et al. (1986 ); Santos et al. (2001 ); Zhao et al. (2006 ). For bond-length data, see: Allen et al. (1987 );

Experimental

Crystal data

C₂₄H₂₀BrN₃O₄S
M_r = 526.40
Triclinic, $[P \overline 1]$
a = 9.3152 (17) Å
b = 10.1223 (18) Å
c = 13.472 (3) Å
α = 94.507 (3)°
β = 109.034 (3)°
γ = 102.953 (3)°
V = 1154.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.91 mm⁻¹
T = 294 (2) K
0.20 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.623, T_max = 0.826
6027 measured reflections
4035 independent reflections
3133 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.088
S = 1.02
4035 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O4	0.93	2.40	3.056 (3)	127
C21—H21⋯O4ⁱ	0.93	2.57	3.290 (4)	135
Symmetry code: (i) -x, -y+1, -z+1.

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/S160053680803688X/at2667sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803688X/at2667Isup2.hkl

checkCIF report

Comment top

Schiff-base ligands have received a good deal of attention in biology and chemistry (Kahwa et al., 1986). 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)-5-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yliminomethyl)-2-methoxyphenyl benzenesulfonate (Chen & Yu, 2006) and (E)-4-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yliminomethyl)-2-methoxyphenyl benzenesulfonate (Zhao et al., 2006) have been reported. Structural information is useful when investigating the coordination properties of Schiff bases functioning as ligands. We report here the synthesis and molecular structure of the title Schiff base compound, (I), (Fig. 1)

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The pyrazolone ring (C14—C16/N1—N3/O4) is almost planar, with an r.m.s. deviation for fitted atoms of 0.0345 Å. It makes a dihedral angle of 42.12 (8)° with the attached phenyl ring (C19—C24). The central benzene ring (C7—C13/O3) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0264 Å. This group makes dihedral angles of 24.55 (8)°, 49.52 (12)° and 59.65 (7)°, respectively, with the the pyrazolone ring (C14—C16/N1—N3/O4), the bromobenzene ring (C1—C6) and the terminal phenyl ring (C19—C24).

An intramolecular C13—H13···O4═C15 hydrogen bond is found in (I) (Table 1), which helps to stabilize the conformation of the molecule. Packing is stabilized by weak, non-classical intermolecular C21—H21···O4═C15 hydrogen bonds that form inversion related dimers (Table 1, Fig. 2).

Related literature top

For general background on Schiff base ligands, see: Chen & Yu (2006); Kahwa et al. (1986); Santos et al. (2001); Zhao et al. (2006). For bond-length data, see: Allen et al. (1987);

Experimental top

An anhydrous ethanol solution (50 ml) of 3-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 81% yield. Yellow single crystals of (I) suitable for X-ray analysis 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 structure of (I), with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I), with hydrogen bonds drawn as dashed lines.

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

Crystal data top

C₂₄H₂₀BrN₃O₄S	Z = 2
M_r = 526.40	F(000) = 536
Triclinic, P1	D_x = 1.515 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3152 (17) Å	Cell parameters from 2541 reflections
b = 10.1223 (18) Å	θ = 2.4–26.1°
c = 13.472 (3) Å	µ = 1.91 mm⁻¹
α = 94.507 (3)°	T = 294 K
β = 109.034 (3)°	Block, yellow
γ = 102.953 (3)°	0.20 × 0.18 × 0.10 mm
V = 1154.3 (4) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4035 independent reflections
Radiation source: fine-focus sealed tube	3133 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→11
T_min = 0.623, T_max = 0.826	k = −12→11
6027 measured reflections	l = −16→15

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.038P)² + 0.609P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4035 reflections	Δρ_max = 0.27 e Å⁻³
301 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0475 (19)

Crystal data top

C₂₄H₂₀BrN₃O₄S	γ = 102.953 (3)°
M_r = 526.40	V = 1154.3 (4) Å³
Triclinic, P1	Z = 2
a = 9.3152 (17) Å	Mo Kα radiation
b = 10.1223 (18) Å	µ = 1.91 mm⁻¹
c = 13.472 (3) Å	T = 294 K
α = 94.507 (3)°	0.20 × 0.18 × 0.10 mm
β = 109.034 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4035 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3133 reflections with I > 2σ(I)
T_min = 0.623, T_max = 0.826	R_int = 0.018
6027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
4035 reflections	Δρ_min = −0.37 e Å⁻³
301 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	1.29069 (4)	0.88146 (3)	0.88042 (3)	0.05949 (16)
S1	1.23680 (9)	0.25329 (8)	0.93033 (8)	0.0591 (3)
N1	0.6951 (3)	0.4506 (2)	0.71737 (18)	0.0415 (6)
N2	0.4487 (3)	0.6559 (2)	0.57841 (19)	0.0422 (6)
N3	0.5999 (3)	0.7481 (2)	0.61946 (19)	0.0434 (6)
O1	1.1993 (3)	0.2290 (2)	1.02189 (19)	0.0751 (7)
O2	1.3668 (3)	0.2167 (3)	0.9141 (3)	0.0903 (10)
O3	1.0922 (2)	0.1687 (2)	0.82766 (17)	0.0521 (5)
O4	0.3384 (2)	0.4347 (2)	0.59904 (17)	0.0511 (5)
C1	1.1929 (4)	0.5050 (3)	0.9740 (2)	0.0508 (8)
H1	1.1501	0.4679	1.0223	0.061*
C2	1.2014 (3)	0.6396 (3)	0.9614 (2)	0.0481 (7)
H2	1.1620	0.6935	0.9996	0.058*
C3	1.2687 (3)	0.6936 (3)	0.8917 (2)	0.0429 (7)
C4	1.3231 (5)	0.6147 (4)	0.8332 (3)	0.0708 (10)
H4	1.3674	0.6525	0.7858	0.085*
C5	1.3127 (5)	0.4803 (4)	0.8442 (3)	0.0718 (11)
H5	1.3491	0.4262	0.8040	0.086*
C6	1.2479 (3)	0.4251 (3)	0.9152 (2)	0.0466 (7)
C7	0.9359 (3)	0.1566 (3)	0.8247 (2)	0.0411 (7)
C8	0.8593 (3)	0.2500 (3)	0.7803 (2)	0.0408 (7)
H8	0.9115	0.3239	0.7572	0.049*
C9	0.7025 (3)	0.2331 (3)	0.7700 (2)	0.0402 (7)
C10	0.6279 (4)	0.1203 (3)	0.8041 (2)	0.0477 (7)
H10	0.5224	0.1068	0.7963	0.057*
C11	0.7077 (4)	0.0283 (3)	0.8491 (2)	0.0511 (8)
H11	0.6562	−0.0461	0.8721	0.061*
C12	0.8633 (4)	0.0457 (3)	0.8604 (2)	0.0459 (7)
H12	0.9181	−0.0158	0.8912	0.055*
C13	0.6187 (3)	0.3337 (3)	0.7256 (2)	0.0423 (7)
H13	0.5094	0.3118	0.7033	0.051*
C14	0.6199 (3)	0.5460 (3)	0.6704 (2)	0.0386 (6)
C15	0.4552 (3)	0.5307 (3)	0.6145 (2)	0.0380 (6)
C16	0.7007 (3)	0.6739 (3)	0.6675 (2)	0.0414 (7)
C17	0.8746 (3)	0.7324 (3)	0.7076 (3)	0.0617 (9)
H17A	0.9236	0.6804	0.7589	0.093*
H17B	0.9003	0.8264	0.7406	0.093*
H17C	0.9121	0.7282	0.6493	0.093*
C18	0.6390 (4)	0.8479 (3)	0.5533 (3)	0.0575 (9)
H18A	0.7288	0.9211	0.5962	0.086*
H18B	0.5509	0.8848	0.5229	0.086*
H18C	0.6628	0.8035	0.4973	0.086*
C19	0.3137 (3)	0.7097 (3)	0.5527 (2)	0.0424 (7)
C20	0.1735 (3)	0.6289 (3)	0.4787 (2)	0.0513 (8)
H20	0.1674	0.5420	0.4468	0.062*
C21	0.0424 (4)	0.6802 (4)	0.4531 (3)	0.0666 (10)
H21	−0.0533	0.6265	0.4045	0.080*
C22	0.0526 (5)	0.8098 (5)	0.4988 (4)	0.0758 (12)
H22	−0.0355	0.8441	0.4797	0.091*
C23	0.1922 (5)	0.8887 (4)	0.5725 (3)	0.0729 (11)
H23	0.1985	0.9761	0.6037	0.087*
C24	0.3232 (4)	0.8382 (3)	0.6003 (3)	0.0575 (8)
H24	0.4176	0.8908	0.6510	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0675 (3)	0.03803 (19)	0.0694 (3)	0.00752 (14)	0.02286 (17)	0.01353 (15)
S1	0.0468 (5)	0.0447 (4)	0.0819 (6)	0.0191 (4)	0.0097 (4)	0.0255 (4)
N1	0.0401 (13)	0.0415 (13)	0.0438 (14)	0.0172 (11)	0.0109 (11)	0.0109 (11)
N2	0.0332 (12)	0.0372 (12)	0.0536 (15)	0.0124 (10)	0.0087 (11)	0.0134 (11)
N3	0.0360 (13)	0.0368 (12)	0.0551 (15)	0.0087 (10)	0.0122 (11)	0.0136 (11)
O1	0.0811 (17)	0.0595 (15)	0.0663 (16)	0.0108 (12)	0.0024 (13)	0.0320 (12)
O2	0.0494 (15)	0.0619 (16)	0.161 (3)	0.0314 (12)	0.0258 (16)	0.0295 (17)
O3	0.0504 (13)	0.0454 (12)	0.0675 (14)	0.0236 (9)	0.0218 (11)	0.0122 (10)
O4	0.0360 (11)	0.0454 (12)	0.0679 (14)	0.0091 (9)	0.0120 (10)	0.0196 (10)
C1	0.0534 (19)	0.0499 (18)	0.0507 (19)	0.0076 (14)	0.0228 (15)	0.0153 (15)
C2	0.0526 (18)	0.0402 (16)	0.0526 (19)	0.0080 (13)	0.0237 (15)	0.0040 (14)
C3	0.0439 (16)	0.0379 (15)	0.0430 (17)	0.0076 (12)	0.0123 (13)	0.0074 (13)
C4	0.103 (3)	0.055 (2)	0.082 (3)	0.024 (2)	0.063 (2)	0.0270 (19)
C5	0.101 (3)	0.056 (2)	0.092 (3)	0.037 (2)	0.064 (2)	0.022 (2)
C6	0.0444 (17)	0.0411 (16)	0.0542 (19)	0.0139 (13)	0.0136 (14)	0.0167 (14)
C7	0.0419 (16)	0.0369 (15)	0.0437 (17)	0.0155 (12)	0.0109 (13)	0.0056 (12)
C8	0.0464 (17)	0.0360 (15)	0.0417 (16)	0.0116 (12)	0.0158 (13)	0.0121 (12)
C9	0.0413 (16)	0.0382 (15)	0.0383 (16)	0.0113 (12)	0.0092 (12)	0.0082 (12)
C10	0.0425 (17)	0.0459 (17)	0.0507 (18)	0.0088 (13)	0.0127 (14)	0.0102 (14)
C11	0.057 (2)	0.0392 (16)	0.0540 (19)	0.0058 (14)	0.0182 (15)	0.0143 (14)
C12	0.0564 (19)	0.0313 (14)	0.0466 (18)	0.0143 (13)	0.0107 (14)	0.0123 (13)
C13	0.0385 (16)	0.0458 (17)	0.0433 (17)	0.0142 (13)	0.0118 (13)	0.0126 (13)
C14	0.0361 (15)	0.0405 (15)	0.0410 (16)	0.0153 (12)	0.0115 (12)	0.0107 (12)
C15	0.0372 (16)	0.0386 (15)	0.0411 (16)	0.0137 (13)	0.0137 (12)	0.0121 (12)
C16	0.0366 (15)	0.0414 (16)	0.0468 (17)	0.0143 (12)	0.0120 (13)	0.0111 (13)
C17	0.0378 (17)	0.0502 (19)	0.087 (3)	0.0096 (14)	0.0105 (17)	0.0128 (17)
C18	0.0542 (19)	0.0484 (18)	0.070 (2)	0.0110 (15)	0.0201 (17)	0.0249 (16)
C19	0.0411 (16)	0.0506 (17)	0.0445 (17)	0.0204 (13)	0.0182 (13)	0.0221 (14)
C20	0.0414 (17)	0.065 (2)	0.0489 (19)	0.0165 (15)	0.0136 (14)	0.0203 (16)
C21	0.0413 (19)	0.097 (3)	0.068 (2)	0.0250 (19)	0.0174 (17)	0.039 (2)
C22	0.062 (3)	0.102 (3)	0.098 (3)	0.054 (2)	0.042 (2)	0.058 (3)
C23	0.084 (3)	0.070 (2)	0.094 (3)	0.049 (2)	0.047 (2)	0.035 (2)
C24	0.060 (2)	0.0531 (19)	0.064 (2)	0.0269 (16)	0.0192 (17)	0.0161 (16)

Geometric parameters (Å, º) top

Br1—C3	1.890 (3)	C9—C10	1.390 (4)
S1—O1	1.412 (3)	C9—C13	1.467 (4)
S1—O2	1.419 (3)	C10—C11	1.376 (4)
S1—O3	1.594 (2)	C10—H10	0.9300
S1—C6	1.751 (3)	C11—C12	1.376 (4)
N1—C13	1.270 (3)	C11—H11	0.9300
N1—C14	1.390 (3)	C12—H12	0.9300
N2—C15	1.399 (3)	C13—H13	0.9300
N2—N3	1.408 (3)	C14—C16	1.355 (4)
N2—C19	1.432 (3)	C14—C15	1.437 (4)
N3—C16	1.364 (3)	C16—C17	1.488 (4)
N3—C18	1.462 (4)	C17—H17A	0.9600
O3—C7	1.420 (3)	C17—H17B	0.9600
O4—C15	1.232 (3)	C17—H17C	0.9600
C1—C2	1.375 (4)	C18—H18A	0.9600
C1—C6	1.376 (4)	C18—H18B	0.9600
C1—H1	0.9300	C18—H18C	0.9600
C2—C3	1.373 (4)	C19—C24	1.374 (4)
C2—H2	0.9300	C19—C20	1.383 (4)
C3—C4	1.363 (4)	C20—C21	1.385 (4)
C4—C5	1.366 (5)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.374 (6)
C5—C6	1.378 (4)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.372 (6)
C7—C8	1.368 (4)	C22—H22	0.9300
C7—C12	1.380 (4)	C23—C24	1.380 (5)
C8—C9	1.391 (4)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300

O1—S1—O2	121.47 (17)	C10—C11—H11	119.8
O1—S1—O3	108.79 (13)	C11—C12—C7	118.3 (3)
O2—S1—O3	102.68 (16)	C11—C12—H12	120.8
O1—S1—C6	109.11 (16)	C7—C12—H12	120.8
O2—S1—C6	109.41 (15)	N1—C13—C9	120.1 (3)
O3—S1—C6	103.86 (13)	N1—C13—H13	119.9
C13—N1—C14	121.9 (2)	C9—C13—H13	119.9
C15—N2—N3	109.4 (2)	C16—C14—N1	122.1 (2)
C15—N2—C19	125.0 (2)	C16—C14—C15	108.3 (2)
N3—N2—C19	119.0 (2)	N1—C14—C15	129.5 (2)
C16—N3—N2	106.3 (2)	O4—C15—N2	123.9 (2)
C16—N3—C18	121.9 (2)	O4—C15—C14	131.5 (2)
N2—N3—C18	116.9 (2)	N2—C15—C14	104.6 (2)
C7—O3—S1	119.49 (18)	C14—C16—N3	110.7 (2)
C2—C1—C6	120.0 (3)	C14—C16—C17	127.6 (3)
C2—C1—H1	120.0	N3—C16—C17	121.7 (2)
C6—C1—H1	120.0	C16—C17—H17A	109.5
C3—C2—C1	119.1 (3)	C16—C17—H17B	109.5
C3—C2—H2	120.4	H17A—C17—H17B	109.5
C1—C2—H2	120.4	C16—C17—H17C	109.5
C4—C3—C2	121.0 (3)	H17A—C17—H17C	109.5
C4—C3—Br1	120.0 (2)	H17B—C17—H17C	109.5
C2—C3—Br1	119.0 (2)	N3—C18—H18A	109.5
C3—C4—C5	120.1 (3)	N3—C18—H18B	109.5
C3—C4—H4	120.0	H18A—C18—H18B	109.5
C5—C4—H4	120.0	N3—C18—H18C	109.5
C4—C5—C6	119.7 (3)	H18A—C18—H18C	109.5
C4—C5—H5	120.2	H18B—C18—H18C	109.5
C6—C5—H5	120.2	C24—C19—C20	120.9 (3)
C1—C6—C5	120.1 (3)	C24—C19—N2	120.9 (3)
C1—C6—S1	120.3 (2)	C20—C19—N2	118.2 (3)
C5—C6—S1	119.6 (3)	C19—C20—C21	118.6 (3)
C8—C7—C12	122.4 (3)	C19—C20—H20	120.7
C8—C7—O3	118.9 (2)	C21—C20—H20	120.7
C12—C7—O3	118.6 (2)	C22—C21—C20	120.5 (3)
C7—C8—C9	119.3 (3)	C22—C21—H21	119.7
C7—C8—H8	120.4	C20—C21—H21	119.7
C9—C8—H8	120.4	C23—C22—C21	120.3 (3)
C10—C9—C8	118.7 (3)	C23—C22—H22	119.9
C10—C9—C13	120.8 (3)	C21—C22—H22	119.9
C8—C9—C13	120.5 (2)	C22—C23—C24	119.9 (4)
C11—C10—C9	121.0 (3)	C22—C23—H23	120.1
C11—C10—H10	119.5	C24—C23—H23	120.1
C9—C10—H10	119.5	C19—C24—C23	119.8 (3)
C12—C11—C10	120.4 (3)	C19—C24—H24	120.1
C12—C11—H11	119.8	C23—C24—H24	120.1

C15—N2—N3—C16	8.2 (3)	O3—C7—C12—C11	−174.7 (3)
C19—N2—N3—C16	161.0 (2)	C14—N1—C13—C9	176.4 (2)
C15—N2—N3—C18	148.2 (3)	C10—C9—C13—N1	163.9 (3)
C19—N2—N3—C18	−58.9 (3)	C8—C9—C13—N1	−15.1 (4)
O1—S1—O3—C7	37.5 (2)	C13—N1—C14—C16	175.7 (3)
O2—S1—O3—C7	167.5 (2)	C13—N1—C14—C15	−7.4 (5)
C6—S1—O3—C7	−78.6 (2)	N3—N2—C15—O4	173.4 (3)
C6—C1—C2—C3	−1.6 (5)	C19—N2—C15—O4	22.5 (4)
C1—C2—C3—C4	1.7 (5)	N3—N2—C15—C14	−5.7 (3)
C1—C2—C3—Br1	−176.5 (2)	C19—N2—C15—C14	−156.6 (3)
C2—C3—C4—C5	−0.7 (6)	C16—C14—C15—O4	−177.8 (3)
Br1—C3—C4—C5	177.5 (3)	N1—C14—C15—O4	5.0 (5)
C3—C4—C5—C6	−0.4 (6)	C16—C14—C15—N2	1.2 (3)
C2—C1—C6—C5	0.5 (5)	N1—C14—C15—N2	−176.0 (3)
C2—C1—C6—S1	−179.7 (2)	N1—C14—C16—N3	−178.6 (2)
C4—C5—C6—C1	0.5 (6)	C15—C14—C16—N3	4.0 (3)
C4—C5—C6—S1	−179.2 (3)	N1—C14—C16—C17	2.4 (5)
O1—S1—C6—C1	−12.4 (3)	C15—C14—C16—C17	−175.1 (3)
O2—S1—C6—C1	−147.5 (3)	N2—N3—C16—C14	−7.5 (3)
O3—S1—C6—C1	103.5 (3)	C18—N3—C16—C14	−145.0 (3)
O1—S1—C6—C5	167.3 (3)	N2—N3—C16—C17	171.7 (3)
O2—S1—C6—C5	32.3 (3)	C18—N3—C16—C17	34.1 (4)
O3—S1—C6—C5	−76.8 (3)	C15—N2—C19—C24	124.7 (3)
S1—O3—C7—C8	93.0 (3)	N3—N2—C19—C24	−23.7 (4)
S1—O3—C7—C12	−91.3 (3)	C15—N2—C19—C20	−55.3 (4)
C12—C7—C8—C9	−0.2 (4)	N3—N2—C19—C20	156.3 (3)
O3—C7—C8—C9	175.3 (2)	C24—C19—C20—C21	0.2 (4)
C7—C8—C9—C10	−0.9 (4)	N2—C19—C20—C21	−179.8 (3)
C7—C8—C9—C13	178.2 (3)	C19—C20—C21—C22	1.3 (5)
C8—C9—C10—C11	1.3 (4)	C20—C21—C22—C23	−1.6 (5)
C13—C9—C10—C11	−177.8 (3)	C21—C22—C23—C24	0.4 (6)
C9—C10—C11—C12	−0.6 (5)	C20—C19—C24—C23	−1.3 (5)
C10—C11—C12—C7	−0.4 (4)	N2—C19—C24—C23	178.7 (3)
C8—C7—C12—C11	0.9 (4)	C22—C23—C24—C19	1.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O4	0.93	2.40	3.056 (3)	127
C21—H21···O4ⁱ	0.93	2.57	3.290 (4)	135

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀BrN₃O₄S
M_r	526.40
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	9.3152 (17), 10.1223 (18), 13.472 (3)
α, β, γ (°)	94.507 (3), 109.034 (3), 102.953 (3)
V (Å³)	1154.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.91
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.623, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	6027, 4035, 3133
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.088, 1.02
No. of reflections	4035
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.37

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
C13—H13···O4	0.93	2.40	3.056 (3)	127
C21—H21···O4ⁱ	0.93	2.57	3.290 (4)	135

Symmetry code: (i) −x, −y+1, −z+1.

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 for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, X. & Yu, M. (2006). Acta Cryst. E62, o4592–o4593. 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
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
Zhao, Y.-L., Zhang, Q.-Z., Chen, X. & Yu, M. (2006). Acta Cryst. E62, o4590–o4591. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

(E)-3-[(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

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Refinement

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References

organic compounds

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