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

In the title compound, C(25)H(22)ClN(3)O(5)S, the two N atoms in the pyrazole ring have a pyramidal environment, with the sums of the valence angles around them being 349.3 (2) and 357.5 (2)°. The phenyl ring is twisted by 50.97 (12)° from the pyrazole mean plane. In the crystal, pairs of weak C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers.

Related literature

For general background to the use of Schiff base derivatives in the development of protein and enzyme mimics, see: Santos et al. (2001 ▶). For related structures, see: Zhang et al. (2006 ▶); Han et al. (2008 ▶); Guo et al. (2010 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H22ClN3O5S

M = 511.98

Monoclinic,

a = 11.063 (2) Å

b = 10.153 (2) Å

c = 22.159 (4) Å

β = 98.73 (3)°

V = 2460.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 294 K

0.30 × 0.26 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.907, T max = 0.951

19683 measured reflections

4315 independent reflections

3016 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.154

S = 1.00

4315 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.45 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/S160053681202627X/cv5310sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202627X/cv5310Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202627X/cv5310Isup3.cml

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

C25H22ClN3O5S	F(000) = 1064
Mr = 511.98	Dx = 1.382 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5316 reflections
a = 11.063 (2) Å	θ = 2.7–27.9°
b = 10.153 (2) Å	µ = 0.28 mm−1
c = 22.159 (4) Å	T = 294 K
β = 98.73 (3)°	Block, yellow
V = 2460.1 (8) Å3	0.30 × 0.26 × 0.18 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4315 independent reflections
Radiation source: fine-focus sealed tube	3016 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→13
Tmin = 0.907, Tmax = 0.951	k = −12→11
19683 measured reflections	l = −26→26

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0919P)2] where P = (Fo2 + 2Fc2)/3
4315 reflections	(Δ/σ)max < 0.001
319 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.45 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
Cl1	0.47353 (11)	1.05947 (9)	0.12284 (7)	0.1381 (5)
S1	0.44039 (6)	0.44761 (7)	0.13133 (3)	0.0563 (3)
N1	0.80799 (17)	0.1811 (2)	0.00538 (9)	0.0454 (5)
N2	0.91575 (19)	0.0090 (2)	−0.11867 (10)	0.0515 (6)
N3	0.88868 (18)	−0.09430 (19)	−0.08078 (9)	0.0477 (5)
O1	0.36954 (18)	0.4061 (2)	0.17629 (10)	0.0786 (7)
O2	0.41778 (17)	0.3950 (2)	0.07100 (9)	0.0729 (6)
O3	0.57713 (14)	0.40946 (15)	0.16147 (7)	0.0497 (5)
O4	0.70559 (15)	0.62701 (17)	0.19204 (8)	0.0548 (5)
O5	0.92591 (17)	0.23713 (16)	−0.11241 (9)	0.0617 (5)
C1	0.4426 (2)	0.6207 (3)	0.12761 (12)	0.0516 (7)
C2	0.4230 (3)	0.6931 (3)	0.17786 (15)	0.0699 (8)
H2	0.4046	0.6510	0.2126	0.084*
C3	0.4310 (3)	0.8292 (3)	0.17608 (19)	0.0835 (10)
H3	0.4171	0.8797	0.2094	0.100*
C4	0.4600 (3)	0.8884 (3)	0.1241 (2)	0.0829 (10)
C5	0.4784 (3)	0.8173 (4)	0.07370 (18)	0.0809 (10)
H5	0.4966	0.8596	0.0389	0.097*
C6	0.4693 (2)	0.6812 (3)	0.07553 (14)	0.0651 (8)
H6	0.4812	0.6311	0.0418	0.078*
C7	0.67271 (19)	0.4424 (2)	0.12844 (10)	0.0406 (6)
C8	0.7020 (2)	0.3589 (2)	0.08434 (11)	0.0440 (6)
H8	0.6593	0.2804	0.0761	0.053*
C9	0.7967 (2)	0.3923 (2)	0.05159 (11)	0.0426 (6)
C10	0.8574 (2)	0.5106 (2)	0.06549 (11)	0.0480 (6)
H10	0.9176	0.5362	0.0428	0.058*
C11	0.8311 (2)	0.5919 (2)	0.11203 (11)	0.0462 (6)
H11	0.8754	0.6690	0.1213	0.055*
C12	0.7384 (2)	0.5579 (2)	0.14468 (11)	0.0425 (6)
C13	0.7683 (3)	0.7483 (3)	0.20859 (15)	0.0705 (9)
H13A	0.8534	0.7307	0.2222	0.106*
H13B	0.7334	0.7898	0.2409	0.106*
H13C	0.7602	0.8058	0.1738	0.106*
C14	0.8334 (2)	0.3028 (3)	0.00548 (11)	0.0479 (6)
H14	0.8762	0.3361	−0.0242	0.057*
C15	0.8452 (2)	0.0964 (2)	−0.03798 (11)	0.0426 (6)
C16	0.8973 (2)	0.1298 (2)	−0.09185 (11)	0.0464 (6)
C17	0.8386 (2)	−0.0375 (2)	−0.03448 (11)	0.0454 (6)
C18	0.7882 (3)	−0.1191 (3)	0.01137 (13)	0.0641 (8)
H18A	0.7636	−0.0631	0.0422	0.096*
H18B	0.8497	−0.1794	0.0299	0.096*
H18C	0.7188	−0.1676	−0.0083	0.096*
C19	0.8505 (3)	−0.2198 (3)	−0.10901 (15)	0.0740 (9)
H19A	0.8321	−0.2801	−0.0783	0.111*
H19B	0.9152	−0.2551	−0.1285	0.111*
H19C	0.7790	−0.2070	−0.1389	0.111*
C20	0.9860 (2)	−0.0126 (2)	−0.16676 (11)	0.0464 (6)
C21	1.0877 (2)	−0.0934 (3)	−0.15858 (13)	0.0590 (7)
H21	1.1128	−0.1339	−0.1212	0.071*
C22	1.1517 (3)	−0.1131 (3)	−0.20709 (15)	0.0713 (9)
H22	1.2197	−0.1681	−0.2022	0.086*
C23	1.1156 (3)	−0.0521 (3)	−0.26230 (15)	0.0746 (10)
H23	1.1578	−0.0676	−0.2949	0.090*
C24	1.0169 (3)	0.0320 (3)	−0.26911 (13)	0.0698 (9)
H24	0.9948	0.0764	−0.3058	0.084*
C25	0.9499 (2)	0.0510 (3)	−0.22172 (12)	0.0581 (7)
H25	0.8817	0.1057	−0.2268	0.070*

	U11	U22	U33	U12	U13	U23
Cl1	0.1248 (9)	0.0543 (6)	0.2232 (15)	0.0018 (5)	−0.0119 (9)	0.0116 (7)
S1	0.0484 (4)	0.0558 (5)	0.0687 (5)	−0.0162 (3)	0.0215 (3)	−0.0118 (3)
N1	0.0461 (11)	0.0448 (13)	0.0460 (12)	−0.0022 (10)	0.0092 (9)	−0.0025 (9)
N2	0.0614 (13)	0.0431 (12)	0.0546 (14)	−0.0067 (10)	0.0239 (11)	−0.0020 (10)
N3	0.0568 (12)	0.0386 (12)	0.0500 (12)	−0.0078 (10)	0.0156 (10)	−0.0030 (9)
O1	0.0710 (13)	0.0767 (14)	0.0990 (16)	−0.0271 (11)	0.0480 (12)	−0.0073 (12)
O2	0.0650 (12)	0.0821 (15)	0.0712 (14)	−0.0193 (10)	0.0095 (10)	−0.0306 (11)
O3	0.0537 (10)	0.0459 (10)	0.0535 (11)	−0.0081 (8)	0.0208 (8)	0.0004 (8)
O4	0.0549 (11)	0.0530 (11)	0.0576 (11)	−0.0096 (8)	0.0124 (9)	−0.0172 (8)
O5	0.0811 (13)	0.0442 (11)	0.0669 (13)	−0.0084 (9)	0.0345 (11)	0.0020 (9)
C1	0.0391 (14)	0.0532 (16)	0.0631 (17)	−0.0016 (11)	0.0102 (12)	−0.0045 (13)
C2	0.0656 (18)	0.065 (2)	0.083 (2)	−0.0015 (16)	0.0242 (16)	−0.0099 (17)
C3	0.073 (2)	0.066 (2)	0.111 (3)	0.0068 (17)	0.010 (2)	−0.026 (2)
C4	0.0586 (19)	0.058 (2)	0.126 (3)	0.0053 (16)	−0.006 (2)	0.009 (2)
C5	0.067 (2)	0.073 (2)	0.099 (3)	0.0016 (17)	−0.0010 (19)	0.026 (2)
C6	0.0547 (17)	0.069 (2)	0.069 (2)	0.0006 (14)	−0.0002 (14)	0.0035 (15)
C7	0.0411 (13)	0.0379 (13)	0.0448 (14)	−0.0021 (10)	0.0125 (11)	0.0016 (10)
C8	0.0463 (13)	0.0356 (13)	0.0512 (15)	−0.0052 (11)	0.0111 (11)	0.0004 (11)
C9	0.0453 (13)	0.0372 (13)	0.0469 (14)	−0.0023 (11)	0.0122 (11)	0.0010 (10)
C10	0.0462 (14)	0.0453 (15)	0.0558 (16)	−0.0061 (11)	0.0184 (12)	0.0029 (12)
C11	0.0426 (13)	0.0395 (14)	0.0560 (16)	−0.0081 (11)	0.0061 (11)	−0.0025 (11)
C12	0.0423 (14)	0.0383 (13)	0.0458 (14)	0.0016 (11)	0.0034 (11)	−0.0020 (11)
C13	0.0780 (19)	0.0533 (18)	0.081 (2)	−0.0145 (15)	0.0125 (16)	−0.0280 (15)
C14	0.0472 (14)	0.0502 (16)	0.0491 (15)	−0.0022 (12)	0.0163 (12)	−0.0024 (12)
C15	0.0400 (13)	0.0410 (14)	0.0476 (14)	−0.0054 (11)	0.0095 (11)	−0.0009 (11)
C16	0.0429 (13)	0.0451 (15)	0.0530 (15)	−0.0036 (11)	0.0131 (11)	−0.0041 (12)
C17	0.0429 (14)	0.0480 (15)	0.0462 (15)	−0.0034 (11)	0.0098 (11)	0.0003 (11)
C18	0.080 (2)	0.0533 (17)	0.0636 (19)	−0.0114 (14)	0.0245 (16)	0.0040 (14)
C19	0.094 (2)	0.0513 (18)	0.083 (2)	−0.0229 (16)	0.0352 (19)	−0.0200 (16)
C20	0.0508 (15)	0.0472 (15)	0.0439 (14)	−0.0112 (12)	0.0153 (11)	−0.0061 (11)
C21	0.0636 (17)	0.0621 (18)	0.0544 (17)	0.0006 (14)	0.0187 (14)	−0.0044 (13)
C22	0.072 (2)	0.071 (2)	0.078 (2)	0.0013 (16)	0.0342 (17)	−0.0096 (17)
C23	0.090 (2)	0.080 (2)	0.063 (2)	−0.0271 (19)	0.0385 (18)	−0.0237 (17)
C24	0.089 (2)	0.078 (2)	0.0429 (16)	−0.0328 (19)	0.0130 (15)	−0.0034 (14)
C25	0.0553 (16)	0.0638 (19)	0.0547 (17)	−0.0154 (13)	0.0066 (13)	−0.0030 (14)

Cl1—C4	1.743 (3)	C9—C10	1.388 (3)
S1—O1	1.4218 (18)	C9—C14	1.470 (3)
S1—O2	1.4263 (19)	C10—C11	1.386 (3)
S1—O3	1.6055 (18)	C10—H10	0.9300
S1—C1	1.760 (3)	C11—C12	1.385 (3)
N1—C14	1.267 (3)	C11—H11	0.9300
N1—C15	1.397 (3)	C13—H13A	0.9600
N2—C16	1.391 (3)	C13—H13B	0.9600
N2—N3	1.404 (3)	C13—H13C	0.9600
N2—C20	1.428 (3)	C14—H14	0.9300
N3—C17	1.365 (3)	C15—C17	1.365 (3)
N3—C19	1.453 (3)	C15—C16	1.443 (3)
O3—C7	1.414 (2)	C17—C18	1.484 (3)
O4—C12	1.357 (3)	C18—H18A	0.9600
O4—C13	1.434 (3)	C18—H18B	0.9600
O5—C16	1.241 (3)	C18—H18C	0.9600
C1—C2	1.379 (4)	C19—H19A	0.9600
C1—C6	1.379 (4)	C19—H19B	0.9600
C2—C3	1.386 (4)	C19—H19C	0.9600
C2—H2	0.9300	C20—C21	1.381 (4)
C3—C4	1.379 (5)	C20—C25	1.383 (3)
C3—H3	0.9300	C21—C22	1.389 (3)
C4—C5	1.371 (5)	C21—H21	0.9300
C5—C6	1.386 (5)	C22—C23	1.375 (4)
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.377 (4)
C7—C8	1.370 (3)	C23—H23	0.9300
C7—C12	1.397 (3)	C24—C25	1.388 (4)
C8—C9	1.404 (3)	C24—H24	0.9300
C8—H8	0.9300	C25—H25	0.9300
O1—S1—O2	120.58 (13)	C11—C12—C7	118.2 (2)
O1—S1—O3	102.82 (12)	O4—C13—H13A	109.5
O2—S1—O3	108.64 (11)	O4—C13—H13B	109.5
O1—S1—C1	110.01 (12)	H13A—C13—H13B	109.5
O2—S1—C1	109.40 (14)	O4—C13—H13C	109.5
O3—S1—C1	103.96 (10)	H13A—C13—H13C	109.5
C14—N1—C15	120.9 (2)	H13B—C13—H13C	109.5
C16—N2—N3	110.16 (19)	N1—C14—C9	121.3 (2)
C16—N2—C20	125.9 (2)	N1—C14—H14	119.4
N3—N2—C20	121.39 (19)	C9—C14—H14	119.4
C17—N3—N2	106.35 (19)	C17—C15—N1	123.4 (2)
C17—N3—C19	124.7 (2)	C17—C15—C16	108.2 (2)
N2—N3—C19	118.2 (2)	N1—C15—C16	128.3 (2)
C7—O3—S1	117.31 (14)	O5—C16—N2	123.7 (2)
C12—O4—C13	117.80 (19)	O5—C16—C15	131.8 (2)
C2—C1—C6	121.2 (3)	N2—C16—C15	104.4 (2)
C2—C1—S1	119.3 (2)	C15—C17—N3	110.3 (2)
C6—C1—S1	119.4 (2)	C15—C17—C18	128.6 (2)
C1—C2—C3	119.4 (3)	N3—C17—C18	121.1 (2)
C1—C2—H2	120.3	C17—C18—H18A	109.5
C3—C2—H2	120.3	C17—C18—H18B	109.5
C4—C3—C2	118.9 (3)	H18A—C18—H18B	109.5
C4—C3—H3	120.6	C17—C18—H18C	109.5
C2—C3—H3	120.6	H18A—C18—H18C	109.5
C5—C4—C3	122.2 (3)	H18B—C18—H18C	109.5
C5—C4—Cl1	119.1 (3)	N3—C19—H19A	109.5
C3—C4—Cl1	118.7 (3)	N3—C19—H19B	109.5
C4—C5—C6	118.7 (3)	H19A—C19—H19B	109.5
C4—C5—H5	120.6	N3—C19—H19C	109.5
C6—C5—H5	120.6	H19A—C19—H19C	109.5
C1—C6—C5	119.6 (3)	H19B—C19—H19C	109.5
C1—C6—H6	120.2	C21—C20—C25	120.9 (2)
C5—C6—H6	120.2	C21—C20—N2	121.2 (2)
C8—C7—C12	122.3 (2)	C25—C20—N2	117.9 (2)
C8—C7—O3	119.9 (2)	C20—C21—C22	119.0 (3)
C12—C7—O3	117.74 (19)	C20—C21—H21	120.5
C7—C8—C9	119.7 (2)	C22—C21—H21	120.5
C7—C8—H8	120.2	C23—C22—C21	120.7 (3)
C9—C8—H8	120.2	C23—C22—H22	119.7
C10—C9—C8	117.9 (2)	C21—C22—H22	119.7
C10—C9—C14	121.0 (2)	C22—C23—C24	119.7 (3)
C8—C9—C14	121.1 (2)	C22—C23—H23	120.2
C11—C10—C9	122.1 (2)	C24—C23—H23	120.2
C11—C10—H10	118.9	C23—C24—C25	120.6 (3)
C9—C10—H10	118.9	C23—C24—H24	119.7
C12—C11—C10	119.7 (2)	C25—C24—H24	119.7
C12—C11—H11	120.1	C20—C25—C24	119.0 (3)
C10—C11—H11	120.1	C20—C25—H25	120.5
O4—C12—C11	125.5 (2)	C24—C25—H25	120.5
O4—C12—C7	116.35 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O5i	0.93	2.43	3.199 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O5i	0.93	2.43	3.199 (3)	140

Symmetry code: (i) .