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

Duan, Z.-Y.; Ma, G.-L.; Yang, L.-P.

doi:10.1107/S1600536812010057

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1039

doi:10.1107/S1600536812010057

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

Zhong-Yu Duan,^a ^* Guo-Li Ma ^a and Li-Ping Yang ^a

^aCollege of Chemical Engineering, Hebei University of Technology, Tianjin 300130, People's Republic of China
^*Correspondence e-mail: duan_zhongyu99@163.com

(Received 6 March 2012; accepted 7 March 2012; online 10 March 2012)

In the title compound, C₂₅H₂₂BrN₃O₅S, the central benzene ring makes dihedral angles of 4.41 (10), 67.09 (9) and 62.05 (10)°, respectively, with the pyrazolone, bromobenzene and terminal phenyl rings. The dihedral angle between the pyrazolone and phenyl rings is 57.75 (11)°. In the crystal, two pairs of C—H⋯O hydrogen bonds link the molecules into inversion dimers. A weak intramolecular C—H⋯O hydrogen bonds is also observed.

Related literature

For general background to the use of Schiff base derivatives in the development protein and enzyme mimics, see: Santos et al. (2001 ). For closely related crystal structures, see: Guo et al. (2010 ); Han et al. (2008 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₅H₂₂BrN₃O₅S
M_r = 556.43
Triclinic, $[P \overline 1]$
a = 7.271 (2) Å
b = 12.654 (4) Å
c = 13.645 (5) Å
α = 88.252 (15)°
β = 85.695 (14)°
γ = 73.623 (12)°
V = 1201.0 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.84 mm⁻¹
T = 294 K
0.25 × 0.20 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.628, T_max = 0.787
10073 measured reflections
4225 independent reflections
3239 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.059
S = 0.95
4225 reflections
319 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O5	0.93	2.32	3.020 (3)	132
C22—H22⋯O1ⁱ	0.93	2.51	3.394 (3)	158
C12—H12⋯O5ⁱ	0.93	2.52	3.212 (3)	131
Symmetry code: (i) -x+2, -y+1, -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/S1600536812010057/is5089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010057/is5089Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010057/is5089Isup3.cml

checkCIF report

Comment top

There has been steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potentially biological activities such as 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-ylimino)methyl]-2-methoxyphenyl 4-bromobenzenesulfonate (Guo et al., 2010) and (E)-4-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl]phenyl 4-bromobenzenesulfonate (Han et al., 2008) 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 are within normal ranges (Allen et al., 1987). The pyrazolone ring (C15–C17/N1/N2) is almost planar with an r.m.s. deviation for fitted atoms of 0.058 (2) Å. It makes a dihedral angle of 57.75 (11)° with the attached phenyl ring (C20–C25). The central benzene ring (C7–C12) makes dihedral angles of 4.41 (10), 67.09 (9) and 62.05 (10)°, respectively, with the pyrazolone ring (C15–C17/N1/N2), the bromobenzene ring (C1–C6) and the terminal phenyl ring (C20—C25).

An intramolecular C13—H13···O5═C16 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 C12—H12···O5═C16 and C22—H22···O1═S1 hydrogen bonds that form inversion related dimers (Table 1 and Fig. 2).

Related literature top

For general background to the use of Schiff base derivatives in the development protein and enzyme mimics, see: Santos et al. (2001). For closely related crystal structures, see: Guo et al. (2010); Han et al. (2008). For reference bond-length data, see: Allen et al. (1987).

Experimental top

An anhydrous ethanol solution (50 ml) of 4-formyl-2-methoxyphenyl 4-bromobenzenesulfonate (3.71 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 83% yield. Yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

Structure description top

For general background to the use of Schiff base derivatives in the development protein and enzyme mimics, see: Santos et al. (2001). For closely related crystal structures, see: Guo et al. (2010); Han et al. (2008). For reference bond-length data, see: Allen et al. (1987).

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 the title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound, with hydrogen bonds drawn as dashed lines.

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

Crystal data top

C₂₅H₂₂BrN₃O₅S	Z = 2
M_r = 556.43	F(000) = 568
Triclinic, P1	D_x = 1.539 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.271 (2) Å	Cell parameters from 4454 reflections
b = 12.654 (4) Å	θ = 1.5–27.9°
c = 13.645 (5) Å	µ = 1.84 mm⁻¹
α = 88.252 (15)°	T = 294 K
β = 85.695 (14)°	Block, yellow
γ = 73.623 (12)°	0.25 × 0.20 × 0.13 mm
V = 1201.0 (7) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4225 independent reflections
Radiation source: fine-focus sealed tube	3239 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.628, T_max = 0.787	k = −15→15
10073 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0229P)²] where P = (F_o² + 2F_c²)/3
4225 reflections	(Δ/σ)_max = 0.001
319 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₅H₂₂BrN₃O₅S	γ = 73.623 (12)°
M_r = 556.43	V = 1201.0 (7) Å³
Triclinic, P1	Z = 2
a = 7.271 (2) Å	Mo Kα radiation
b = 12.654 (4) Å	µ = 1.84 mm⁻¹
c = 13.645 (5) Å	T = 294 K
α = 88.252 (15)°	0.25 × 0.20 × 0.13 mm
β = 85.695 (14)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4225 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3239 reflections with I > 2σ(I)
T_min = 0.628, T_max = 0.787	R_int = 0.034
10073 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 0.95	Δρ_max = 0.26 e Å⁻³
4225 reflections	Δρ_min = −0.40 e Å⁻³
319 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	0.01790 (3)	0.265549 (18)	0.722422 (16)	0.02781 (8)
S1	0.77530 (8)	0.26428 (4)	0.45611 (4)	0.01811 (13)
N1	0.4302 (2)	0.65367 (13)	0.05220 (11)	0.0157 (4)
N2	0.2503 (2)	0.88912 (13)	−0.10094 (12)	0.0167 (4)
N3	0.4400 (2)	0.85402 (13)	−0.14262 (12)	0.0171 (4)
O1	0.9083 (2)	0.16360 (12)	0.48414 (10)	0.0264 (4)
O2	0.8183 (2)	0.36677 (11)	0.46382 (10)	0.0232 (4)
O3	0.7449 (2)	0.24482 (10)	0.34352 (9)	0.0170 (3)
O4	0.3891 (2)	0.37409 (11)	0.33591 (10)	0.0199 (3)
O5	0.7202 (2)	0.72221 (11)	−0.10465 (10)	0.0196 (3)
C1	0.4676 (3)	0.36032 (16)	0.57928 (14)	0.0192 (5)
H1	0.5192	0.4197	0.5801	0.023*
C2	0.3033 (3)	0.36003 (17)	0.63858 (15)	0.0217 (5)
H2	0.2443	0.4187	0.6800	0.026*
C3	0.2296 (3)	0.27100 (17)	0.63476 (14)	0.0179 (5)
C4	0.3105 (3)	0.18384 (16)	0.57180 (14)	0.0197 (5)
H4	0.2549	0.1263	0.5684	0.024*
C5	0.4742 (3)	0.18364 (16)	0.51432 (14)	0.0180 (5)
H5	0.5318	0.1252	0.4724	0.022*
C6	0.5533 (3)	0.27149 (16)	0.51911 (13)	0.0149 (5)
C7	0.7089 (3)	0.33446 (15)	0.27618 (13)	0.0153 (5)
C8	0.5194 (3)	0.40007 (16)	0.27035 (14)	0.0158 (5)
C9	0.4833 (3)	0.48370 (15)	0.20023 (14)	0.0153 (5)
H9	0.3591	0.5293	0.1957	0.018*
C10	0.6326 (3)	0.49966 (15)	0.13639 (13)	0.0151 (5)
C11	0.8185 (3)	0.43252 (15)	0.14330 (14)	0.0169 (5)
H11	0.9176	0.4434	0.1007	0.020*
C12	0.8570 (3)	0.34868 (16)	0.21394 (14)	0.0155 (5)
H12	0.9812	0.3032	0.2187	0.019*
C13	0.5975 (3)	0.58684 (16)	0.06028 (14)	0.0171 (5)
H13	0.6991	0.5935	0.0172	0.021*
C14	0.1955 (3)	0.44338 (17)	0.33966 (16)	0.0255 (5)
H14A	0.1930	0.5162	0.3586	0.038*
H14B	0.1177	0.4141	0.3868	0.038*
H14C	0.1461	0.4463	0.2760	0.038*
C15	0.4041 (3)	0.73576 (16)	−0.02068 (14)	0.0147 (5)
C16	0.5449 (3)	0.76256 (15)	−0.09004 (14)	0.0155 (5)
C17	0.2292 (3)	0.80994 (16)	−0.03330 (13)	0.0157 (5)
C18	0.0376 (3)	0.81078 (17)	0.01264 (15)	0.0215 (5)
H18A	−0.0359	0.7898	−0.0350	0.032*
H18B	−0.0281	0.8834	0.0359	0.032*
H18C	0.0528	0.7596	0.0669	0.032*
C19	0.1022 (3)	0.94218 (16)	−0.16870 (14)	0.0205 (5)
H19A	0.1055	0.8928	−0.2213	0.031*
H19B	0.1265	1.0085	−0.1952	0.031*
H19C	−0.0221	0.9598	−0.1338	0.031*
C20	0.5247 (3)	0.93260 (16)	−0.19093 (14)	0.0158 (5)
C21	0.6437 (3)	0.89948 (16)	−0.27480 (14)	0.0185 (5)
H21	0.6640	0.8291	−0.2994	0.022*
C22	0.7329 (3)	0.97310 (17)	−0.32194 (15)	0.0224 (5)
H22	0.8145	0.9516	−0.3780	0.027*
C23	0.7003 (3)	1.07778 (17)	−0.28548 (15)	0.0237 (5)
H23	0.7597	1.1267	−0.3173	0.028*
C24	0.5799 (3)	1.11040 (17)	−0.20180 (16)	0.0250 (5)
H24	0.5580	1.1812	−0.1779	0.030*
C25	0.4917 (3)	1.03730 (16)	−0.15343 (15)	0.0213 (5)
H25	0.4118	1.0584	−0.0968	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02550 (15)	0.03136 (14)	0.02661 (14)	−0.01081 (11)	0.00783 (10)	0.00295 (10)
S1	0.0170 (3)	0.0235 (3)	0.0133 (3)	−0.0052 (3)	−0.0002 (2)	0.0012 (2)
N1	0.0179 (11)	0.0164 (9)	0.0142 (9)	−0.0067 (8)	−0.0029 (8)	0.0001 (7)
N2	0.0134 (10)	0.0186 (9)	0.0175 (9)	−0.0038 (8)	0.0007 (8)	0.0001 (7)
N3	0.0138 (10)	0.0156 (9)	0.0207 (9)	−0.0029 (8)	0.0010 (8)	0.0033 (7)
O1	0.0178 (9)	0.0331 (9)	0.0210 (8)	0.0042 (8)	−0.0011 (7)	0.0077 (7)
O2	0.0263 (9)	0.0306 (9)	0.0179 (8)	−0.0170 (7)	0.0012 (7)	−0.0030 (7)
O3	0.0241 (9)	0.0141 (7)	0.0113 (7)	−0.0032 (7)	0.0004 (6)	0.0013 (6)
O4	0.0146 (8)	0.0236 (8)	0.0197 (8)	−0.0038 (7)	0.0027 (6)	0.0060 (6)
O5	0.0126 (9)	0.0197 (8)	0.0254 (8)	−0.0033 (7)	−0.0017 (7)	0.0050 (6)
C1	0.0214 (13)	0.0184 (11)	0.0202 (11)	−0.0095 (10)	0.0006 (10)	−0.0022 (9)
C2	0.0236 (14)	0.0204 (12)	0.0199 (11)	−0.0049 (11)	0.0036 (10)	−0.0058 (9)
C3	0.0157 (12)	0.0235 (12)	0.0139 (11)	−0.0055 (10)	−0.0005 (9)	0.0054 (9)
C4	0.0235 (13)	0.0158 (11)	0.0220 (12)	−0.0082 (10)	−0.0038 (10)	−0.0004 (9)
C5	0.0204 (13)	0.0163 (11)	0.0170 (11)	−0.0041 (10)	−0.0016 (9)	−0.0028 (9)
C6	0.0144 (12)	0.0184 (11)	0.0110 (10)	−0.0033 (9)	−0.0013 (9)	0.0024 (8)
C7	0.0214 (13)	0.0127 (10)	0.0115 (11)	−0.0042 (10)	−0.0024 (9)	0.0008 (8)
C8	0.0172 (13)	0.0179 (11)	0.0136 (11)	−0.0074 (10)	0.0012 (9)	−0.0031 (9)
C9	0.0154 (12)	0.0151 (11)	0.0145 (10)	−0.0018 (9)	−0.0027 (9)	−0.0024 (8)
C10	0.0191 (13)	0.0143 (11)	0.0130 (11)	−0.0064 (10)	−0.0017 (9)	−0.0028 (8)
C11	0.0180 (13)	0.0201 (11)	0.0144 (11)	−0.0092 (10)	0.0030 (9)	−0.0021 (9)
C12	0.0141 (12)	0.0152 (11)	0.0154 (11)	−0.0007 (9)	−0.0013 (9)	−0.0043 (9)
C13	0.0218 (13)	0.0178 (11)	0.0145 (11)	−0.0103 (10)	0.0002 (9)	−0.0015 (9)
C14	0.0161 (13)	0.0300 (13)	0.0303 (13)	−0.0078 (11)	0.0033 (10)	0.0007 (10)
C15	0.0159 (12)	0.0142 (10)	0.0145 (11)	−0.0052 (9)	−0.0003 (9)	−0.0023 (8)
C16	0.0196 (13)	0.0132 (11)	0.0147 (11)	−0.0054 (10)	−0.0051 (9)	0.0002 (8)
C17	0.0192 (13)	0.0181 (11)	0.0106 (10)	−0.0068 (10)	0.0001 (9)	−0.0036 (9)
C18	0.0190 (13)	0.0255 (12)	0.0190 (11)	−0.0056 (10)	0.0028 (10)	−0.0023 (9)
C19	0.0191 (13)	0.0190 (11)	0.0208 (12)	−0.0006 (10)	−0.0032 (10)	−0.0018 (9)
C20	0.0152 (12)	0.0157 (11)	0.0173 (11)	−0.0051 (9)	−0.0046 (9)	0.0045 (9)
C21	0.0196 (13)	0.0156 (11)	0.0190 (11)	−0.0021 (10)	−0.0039 (10)	0.0005 (9)
C22	0.0187 (13)	0.0296 (13)	0.0184 (12)	−0.0067 (11)	−0.0023 (10)	0.0068 (10)
C23	0.0235 (14)	0.0255 (13)	0.0267 (13)	−0.0133 (11)	−0.0113 (11)	0.0117 (10)
C24	0.0335 (15)	0.0163 (12)	0.0276 (13)	−0.0084 (11)	−0.0120 (11)	0.0019 (10)
C25	0.0247 (14)	0.0195 (12)	0.0183 (11)	−0.0033 (10)	−0.0043 (10)	−0.0007 (9)

Geometric parameters (Å, º) top

Br1—C3	1.893 (2)	C9—H9	0.9300
S1—O2	1.4255 (15)	C10—C11	1.387 (3)
S1—O1	1.4266 (14)	C10—C13	1.474 (3)
S1—O3	1.6045 (15)	C11—C12	1.394 (3)
S1—C6	1.751 (2)	C11—H11	0.9300
N1—C13	1.282 (2)	C12—H12	0.9300
N1—C15	1.399 (2)	C13—H13	0.9300
N2—C17	1.374 (2)	C14—H14A	0.9600
N2—N3	1.406 (2)	C14—H14B	0.9600
N2—C19	1.473 (2)	C14—H14C	0.9600
N3—C16	1.403 (2)	C15—C17	1.370 (3)
N3—C20	1.431 (2)	C15—C16	1.446 (3)
O3—C7	1.416 (2)	C17—C18	1.481 (3)
O4—C8	1.355 (2)	C18—H18A	0.9600
O4—C14	1.431 (2)	C18—H18B	0.9600
O5—C16	1.235 (2)	C18—H18C	0.9600
C1—C6	1.382 (3)	C19—H19A	0.9600
C1—C2	1.393 (3)	C19—H19B	0.9600
C1—H1	0.9300	C19—H19C	0.9600
C2—C3	1.381 (3)	C20—C21	1.382 (3)
C2—H2	0.9300	C20—C25	1.385 (3)
C3—C4	1.384 (3)	C21—C22	1.394 (3)
C4—C5	1.375 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.380 (3)
C5—C6	1.394 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.384 (3)
C7—C12	1.369 (3)	C23—H23	0.9300
C7—C8	1.401 (3)	C24—C25	1.392 (3)
C8—C9	1.387 (3)	C24—H24	0.9300
C9—C10	1.396 (3)	C25—H25	0.9300

O2—S1—O1	120.80 (10)	C11—C12—H12	120.5
O2—S1—O3	109.18 (8)	N1—C13—C10	121.44 (19)
O1—S1—O3	103.54 (8)	N1—C13—H13	119.3
O2—S1—C6	109.56 (9)	C10—C13—H13	119.3
O1—S1—C6	107.69 (9)	O4—C14—H14A	109.5
O3—S1—C6	104.84 (9)	O4—C14—H14B	109.5
C13—N1—C15	119.41 (18)	H14A—C14—H14B	109.5
C17—N2—N3	106.70 (15)	O4—C14—H14C	109.5
C17—N2—C19	123.01 (18)	H14A—C14—H14C	109.5
N3—N2—C19	116.10 (15)	H14B—C14—H14C	109.5
C16—N3—N2	109.69 (16)	C17—C15—N1	122.44 (19)
C16—N3—C20	123.24 (17)	C17—C15—C16	108.33 (17)
N2—N3—C20	119.48 (16)	N1—C15—C16	129.17 (18)
C7—O3—S1	120.03 (12)	O5—C16—N3	123.13 (18)
C8—O4—C14	118.06 (15)	O5—C16—C15	132.29 (18)
C6—C1—C2	119.3 (2)	N3—C16—C15	104.55 (17)
C6—C1—H1	120.3	C15—C17—N2	109.88 (19)
C2—C1—H1	120.3	C15—C17—C18	128.98 (19)
C3—C2—C1	118.8 (2)	N2—C17—C18	121.13 (18)
C3—C2—H2	120.6	C17—C18—H18A	109.5
C1—C2—H2	120.6	C17—C18—H18B	109.5
C2—C3—C4	122.1 (2)	H18A—C18—H18B	109.5
C2—C3—Br1	118.73 (16)	C17—C18—H18C	109.5
C4—C3—Br1	119.14 (16)	H18A—C18—H18C	109.5
C5—C4—C3	118.9 (2)	H18B—C18—H18C	109.5
C5—C4—H4	120.5	N2—C19—H19A	109.5
C3—C4—H4	120.5	N2—C19—H19B	109.5
C4—C5—C6	119.7 (2)	H19A—C19—H19B	109.5
C4—C5—H5	120.2	N2—C19—H19C	109.5
C6—C5—H5	120.2	H19A—C19—H19C	109.5
C1—C6—C5	121.1 (2)	H19B—C19—H19C	109.5
C1—C6—S1	119.14 (16)	C21—C20—C25	121.3 (2)
C5—C6—S1	119.56 (16)	C21—C20—N3	117.67 (18)
C12—C7—C8	122.31 (17)	C25—C20—N3	120.96 (19)
C12—C7—O3	119.05 (17)	C20—C21—C22	119.0 (2)
C8—C7—O3	118.43 (18)	C20—C21—H21	120.5
O4—C8—C9	126.79 (18)	C22—C21—H21	120.5
O4—C8—C7	115.05 (16)	C23—C22—C21	120.1 (2)
C9—C8—C7	118.16 (19)	C23—C22—H22	120.0
C8—C9—C10	120.31 (19)	C21—C22—H22	120.0
C8—C9—H9	119.8	C22—C23—C24	120.4 (2)
C10—C9—H9	119.8	C22—C23—H23	119.8
C11—C10—C9	120.14 (18)	C24—C23—H23	119.8
C11—C10—C13	118.52 (19)	C23—C24—C25	120.0 (2)
C9—C10—C13	121.34 (18)	C23—C24—H24	120.0
C10—C11—C12	120.16 (19)	C25—C24—H24	120.0
C10—C11—H11	119.9	C20—C25—C24	119.0 (2)
C12—C11—H11	119.9	C20—C25—H25	120.5
C7—C12—C11	118.90 (19)	C24—C25—H25	120.5
C7—C12—H12	120.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O5	0.93	2.32	3.020 (3)	132
C22—H22···O1ⁱ	0.93	2.51	3.394 (3)	158
C12—H12···O5ⁱ	0.93	2.52	3.212 (3)	131

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂BrN₃O₅S
M_r	556.43
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.271 (2), 12.654 (4), 13.645 (5)
α, β, γ (°)	88.252 (15), 85.695 (14), 73.623 (12)
V (Å³)	1201.0 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.84
Crystal size (mm)	0.25 × 0.20 × 0.13

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.628, 0.787
No. of measured, independent and observed [I > 2σ(I)] reflections	10073, 4225, 3239
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.059, 0.95
No. of reflections	4225
No. of parameters	319
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.40

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···O5	0.93	2.32	3.020 (3)	132
C22—H22···O1ⁱ	0.93	2.51	3.394 (3)	158
C12—H12···O5ⁱ	0.93	2.52	3.212 (3)	131

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

The project was supported by the Hebei Provincial Natural Science Foundation of China (project grant No. B2010000039).

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. CSD CrossRef Web of Science Google Scholar
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, M.-J., Chen, X. & Yao, J.-X. (2010). Acta Cryst. E66, o1360. Web of Science CSD CrossRef IUCr Journals Google Scholar
Han, J.-R., Tian, X., Zhen, X.-L., Li, Z.-C. & Liu, S.-X. (2008). Acta Cryst. E64, o2244. Web of Science CrossRef IUCr Journals 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]-2-meth­­oxy­phenyl 4-bromo­benzene­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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