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

In the title compound, C(25)H(22)BrN(3)O(5)S, the central benzene ring makes dihedral angles of 4.41 (10), 67.09 (9) and 62.05 (10)°, respectively, with the pyrazolone, bromo-benzene 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 mol-ecules into inversion dimers. A weak intra-molecular 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 = 556.43

Triclinic,

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[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.059

S = 0.95

4225 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.40 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 datablock(s) I, global. DOI: 10.1107/S1600536812010057/is5089sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812010057/is5089Isup3.cml

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

C25H22BrN3O5S	Z = 2
Mr = 556.43	F(000) = 568
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0229P)2] where P = (Fo2 + 2Fc2)/3
4225 reflections	(Δ/σ)max = 0.001
319 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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	0.01790 (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*

	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)

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

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

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) .