(E)-2-Bromo-4-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino-meth-yl]-6-meth-oxy-phenyl 4-methyl-benzene-sulfonate.

In the title compound, C(26)H(24)BrN(3)O(5)S, the central benzene ring makes dihedral angles of 6.27 (6), 33.63 (6) and 69.31 (5)°, respectively, with the pyrazolone ring, the bromo-benzene ring and the terminal phenyl ring. An intra-molecular C-H⋯O hydrogen bond occurs. The crystal packing features weak non-classical C-Br⋯O inter-actions [Br⋯O = 3.222 (2) Å] that form inversion-related 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 closely related crystal structures, see: Chen & Yu (2006 ▶); Han et al. (2008 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H24BrN3O5S

M = 570.45

Monoclinic,

a = 10.210 (2) Å

b = 20.364 (5) Å

c = 12.171 (3) Å

β = 90.906 (4)°

V = 2530.2 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.75 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 = 0.653, T max = 0.797

21416 measured reflections

4462 independent reflections

3998 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.071

S = 1.02

4462 reflections

329 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.36 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/S160053681201447X/ds2184sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201447X/ds2184Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201447X/ds2184Isup3.cml

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

C26H24BrN3O5S	F(000) = 1168
Mr = 570.45	Dx = 1.497 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8917 reflections
a = 10.210 (2) Å	θ = 1.9–27.9°
b = 20.364 (5) Å	µ = 1.75 mm−1
c = 12.171 (3) Å	T = 294 K
β = 90.906 (4)°	Block, yellow
V = 2530.2 (10) Å3	0.25 × 0.20 × 0.13 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4462 independent reflections
Radiation source: fine-focus sealed tube	3998 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→10
Tmin = 0.653, Tmax = 0.797	k = −24→24
21416 measured reflections	l = −14→14

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0428P)2] where P = (Fo2 + 2Fc2)/3
4462 reflections	(Δ/σ)max < 0.001
329 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.36 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	0.19479 (2)	0.007075 (10)	0.092923 (16)	0.03095 (9)
S1	−0.07113 (5)	−0.09236 (2)	0.21545 (4)	0.02290 (13)
N1	0.42286 (15)	0.06686 (7)	0.58171 (12)	0.0162 (3)
N2	0.58362 (15)	0.16776 (7)	0.78091 (12)	0.0189 (4)
N3	0.63838 (16)	0.19415 (7)	0.68517 (12)	0.0196 (4)
O1	−0.08922 (15)	−0.10227 (8)	0.10047 (11)	0.0384 (4)
O2	−0.10940 (13)	−0.03239 (7)	0.26545 (12)	0.0316 (4)
O3	0.08380 (12)	−0.10214 (6)	0.23741 (10)	0.0187 (3)
O4	0.09160 (13)	−0.11147 (6)	0.45433 (10)	0.0223 (3)
O5	0.60059 (14)	0.18166 (6)	0.49768 (10)	0.0251 (3)
C1	−0.1563 (2)	−0.21849 (10)	0.23038 (16)	0.0311 (5)
H1	−0.1283	−0.2236	0.1586	0.037*
C2	−0.2158 (2)	−0.26989 (10)	0.28479 (17)	0.0335 (5)
H2	−0.2259	−0.3101	0.2494	0.040*
C3	−0.26054 (19)	−0.26255 (10)	0.39108 (16)	0.0241 (5)
C4	−0.24054 (19)	−0.20296 (10)	0.44337 (16)	0.0235 (4)
H4	−0.2684	−0.1976	0.5152	0.028*
C5	−0.17980 (18)	−0.15113 (9)	0.39069 (16)	0.0220 (4)
H5	−0.1667	−0.1113	0.4267	0.026*
C6	−0.13930 (18)	−0.15935 (9)	0.28468 (15)	0.0201 (4)
C7	−0.3296 (2)	−0.31719 (10)	0.45012 (18)	0.0317 (5)
H7A	−0.2661	−0.3448	0.4863	0.048*
H7B	−0.3795	−0.3427	0.3981	0.048*
H7C	−0.3872	−0.2989	0.5036	0.048*
C8	0.15558 (18)	−0.05559 (9)	0.29815 (14)	0.0163 (4)
C9	0.22147 (19)	−0.00618 (9)	0.24505 (16)	0.0191 (4)
C10	0.30593 (18)	0.03464 (9)	0.30430 (15)	0.0181 (4)
H10	0.3524	0.0673	0.2685	0.022*
C11	0.32058 (18)	0.02652 (9)	0.41681 (14)	0.0165 (4)
C12	0.24861 (18)	−0.02151 (9)	0.47152 (15)	0.0184 (4)
H12	0.2561	−0.0257	0.5474	0.022*
C13	0.16597 (18)	−0.06287 (9)	0.41222 (14)	0.0164 (4)
C14	0.41265 (18)	0.06955 (9)	0.47673 (15)	0.0183 (4)
H14	0.4640	0.0990	0.4380	0.022*
C15	0.0978 (2)	−0.12144 (11)	0.57034 (16)	0.0302 (5)
H15A	0.1852	−0.1338	0.5918	0.045*
H15B	0.0380	−0.1557	0.5901	0.045*
H15C	0.0743	−0.0815	0.6071	0.045*
C16	0.50319 (18)	0.11137 (9)	0.63731 (15)	0.0163 (4)
C17	0.58248 (19)	0.16334 (9)	0.59291 (15)	0.0191 (4)
C18	0.51022 (18)	0.11514 (9)	0.74984 (14)	0.0166 (4)
C19	0.4502 (2)	0.07000 (9)	0.83058 (15)	0.0231 (4)
H19A	0.5178	0.0461	0.8689	0.035*
H19B	0.3932	0.0397	0.7927	0.035*
H19C	0.4006	0.0950	0.8823	0.035*
C20	0.65966 (19)	0.17428 (9)	0.88324 (14)	0.0213 (4)
H20A	0.6175	0.1501	0.9405	0.032*
H20B	0.6651	0.2198	0.9034	0.032*
H20C	0.7462	0.1572	0.8729	0.032*
C21	0.6892 (2)	0.25949 (9)	0.68276 (14)	0.0208 (4)
C22	0.6206 (2)	0.31109 (9)	0.72901 (15)	0.0262 (5)
H22	0.5433	0.3034	0.7664	0.031*
C23	0.6693 (2)	0.37415 (10)	0.71839 (17)	0.0349 (6)
H23	0.6244	0.4091	0.7493	0.042*
C24	0.7828 (3)	0.38575 (10)	0.66286 (17)	0.0366 (6)
H24	0.8134	0.4285	0.6551	0.044*
C25	0.8518 (2)	0.33407 (11)	0.61842 (17)	0.0343 (6)
H25	0.9294	0.3419	0.5816	0.041*
C26	0.8049 (2)	0.27019 (10)	0.62896 (16)	0.0272 (5)
H26	0.8513	0.2351	0.5999	0.033*

	U11	U22	U33	U12	U13	U23
Br1	0.04143 (16)	0.03531 (15)	0.01582 (12)	−0.01554 (10)	−0.00859 (9)	0.00683 (8)
S1	0.0207 (3)	0.0236 (3)	0.0241 (3)	−0.0062 (2)	−0.0083 (2)	0.0086 (2)
N1	0.0166 (9)	0.0142 (8)	0.0177 (8)	0.0016 (6)	−0.0030 (6)	−0.0042 (6)
N2	0.0256 (9)	0.0164 (8)	0.0145 (8)	−0.0026 (7)	−0.0030 (7)	−0.0006 (6)
N3	0.0268 (10)	0.0168 (9)	0.0149 (8)	−0.0060 (7)	−0.0029 (7)	−0.0001 (6)
O1	0.0418 (10)	0.0504 (10)	0.0225 (8)	−0.0242 (8)	−0.0163 (7)	0.0149 (7)
O2	0.0237 (8)	0.0179 (8)	0.0530 (10)	0.0017 (6)	−0.0022 (7)	0.0094 (7)
O3	0.0180 (7)	0.0191 (7)	0.0187 (7)	−0.0038 (6)	−0.0035 (5)	−0.0043 (5)
O4	0.0255 (8)	0.0257 (8)	0.0158 (7)	−0.0082 (6)	−0.0026 (6)	0.0015 (5)
O5	0.0362 (9)	0.0230 (8)	0.0159 (7)	−0.0093 (6)	−0.0046 (6)	0.0012 (5)
C1	0.0416 (14)	0.0297 (12)	0.0219 (11)	−0.0106 (10)	−0.0008 (9)	−0.0004 (9)
C2	0.0466 (15)	0.0223 (12)	0.0314 (13)	−0.0115 (10)	−0.0026 (10)	−0.0028 (9)
C3	0.0176 (11)	0.0222 (11)	0.0322 (12)	0.0007 (9)	−0.0053 (9)	0.0089 (8)
C4	0.0204 (11)	0.0242 (11)	0.0261 (11)	0.0023 (9)	0.0034 (8)	0.0054 (8)
C5	0.0195 (11)	0.0162 (11)	0.0301 (11)	0.0005 (8)	−0.0016 (9)	−0.0010 (8)
C6	0.0171 (11)	0.0203 (11)	0.0228 (10)	−0.0027 (8)	−0.0054 (8)	0.0057 (8)
C7	0.0298 (13)	0.0256 (12)	0.0395 (13)	−0.0042 (10)	−0.0038 (10)	0.0120 (9)
C8	0.0155 (10)	0.0157 (10)	0.0175 (9)	0.0010 (8)	−0.0043 (7)	−0.0044 (7)
C9	0.0217 (11)	0.0202 (10)	0.0152 (10)	0.0004 (8)	−0.0028 (8)	−0.0001 (7)
C10	0.0195 (11)	0.0144 (10)	0.0202 (10)	−0.0016 (8)	−0.0017 (8)	0.0012 (7)
C11	0.0167 (10)	0.0144 (10)	0.0184 (10)	0.0021 (8)	−0.0014 (8)	−0.0035 (7)
C12	0.0203 (11)	0.0210 (10)	0.0138 (10)	0.0022 (8)	−0.0004 (8)	−0.0022 (7)
C13	0.0158 (10)	0.0171 (10)	0.0163 (10)	0.0000 (8)	0.0001 (7)	0.0013 (7)
C14	0.0195 (11)	0.0138 (10)	0.0216 (10)	0.0015 (8)	0.0001 (8)	−0.0017 (7)
C15	0.0368 (13)	0.0337 (12)	0.0203 (11)	−0.0113 (10)	0.0039 (9)	0.0076 (9)
C16	0.0171 (10)	0.0128 (9)	0.0189 (10)	0.0007 (8)	−0.0022 (8)	−0.0018 (7)
C17	0.0219 (11)	0.0164 (10)	0.0187 (10)	0.0002 (8)	−0.0049 (8)	−0.0012 (7)
C18	0.0170 (10)	0.0142 (10)	0.0186 (10)	0.0025 (8)	−0.0015 (7)	−0.0030 (7)
C19	0.0256 (12)	0.0225 (11)	0.0214 (10)	−0.0031 (9)	0.0030 (8)	−0.0037 (8)
C20	0.0254 (11)	0.0235 (11)	0.0149 (10)	0.0001 (9)	−0.0048 (8)	−0.0030 (8)
C21	0.0314 (12)	0.0153 (10)	0.0153 (10)	−0.0036 (8)	−0.0102 (8)	0.0011 (7)
C22	0.0348 (13)	0.0202 (11)	0.0231 (11)	0.0002 (9)	−0.0104 (9)	0.0002 (8)
C23	0.0557 (16)	0.0216 (12)	0.0270 (12)	0.0010 (11)	−0.0142 (11)	−0.0011 (9)
C24	0.0644 (18)	0.0197 (12)	0.0251 (12)	−0.0170 (11)	−0.0199 (12)	0.0042 (9)
C25	0.0426 (14)	0.0348 (13)	0.0253 (12)	−0.0190 (11)	−0.0063 (10)	0.0033 (9)
C26	0.0346 (13)	0.0234 (11)	0.0235 (11)	−0.0056 (9)	−0.0036 (9)	−0.0003 (8)

Br1—C9	1.8866 (19)	C9—C10	1.391 (3)
S1—O2	1.4220 (15)	C10—C11	1.385 (2)
S1—O1	1.4230 (15)	C10—H10	0.9300
S1—O3	1.6125 (13)	C11—C12	1.398 (3)
S1—C6	1.7533 (19)	C11—C14	1.470 (3)
N1—C14	1.281 (2)	C12—C13	1.387 (2)
N1—C16	1.391 (2)	C12—H12	0.9300
N2—C18	1.358 (2)	C14—H14	0.9300
N2—N3	1.407 (2)	C15—H15A	0.9600
N2—C20	1.463 (2)	C15—H15B	0.9600
N3—C17	1.400 (2)	C15—H15C	0.9600
N3—C21	1.429 (2)	C16—C18	1.373 (2)
O3—C8	1.402 (2)	C16—C17	1.443 (3)
O4—C13	1.353 (2)	C18—C19	1.485 (3)
O4—C15	1.427 (2)	C19—H19A	0.9600
O5—C17	1.234 (2)	C19—H19B	0.9600
C1—C6	1.383 (3)	C19—H19C	0.9600
C1—C2	1.384 (3)	C20—H20A	0.9600
C1—H1	0.9300	C20—H20B	0.9600
C2—C3	1.387 (3)	C20—H20C	0.9600
C2—H2	0.9300	C21—C26	1.377 (3)
C3—C4	1.384 (3)	C21—C22	1.387 (3)
C3—C7	1.506 (3)	C22—C23	1.384 (3)
C4—C5	1.387 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.372 (3)
C5—C6	1.371 (3)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.381 (3)
C7—H7A	0.9600	C24—H24	0.9300
C7—H7B	0.9600	C25—C26	1.393 (3)
C7—H7C	0.9600	C25—H25	0.9300
C8—C9	1.377 (3)	C26—H26	0.9300
C8—C13	1.399 (2)
O2—S1—O1	120.69 (9)	C11—C12—H12	120.1
O2—S1—O3	108.10 (7)	O4—C13—C12	125.98 (16)
O1—S1—O3	104.91 (8)	O4—C13—C8	114.79 (15)
O2—S1—C6	110.41 (9)	C12—C13—C8	119.23 (17)
O1—S1—C6	108.42 (9)	N1—C14—C11	120.69 (17)
O3—S1—C6	102.71 (8)	N1—C14—H14	119.7
C14—N1—C16	119.69 (16)	C11—C14—H14	119.7
C18—N2—N3	107.19 (14)	O4—C15—H15A	109.5
C18—N2—C20	126.28 (15)	O4—C15—H15B	109.5
N3—N2—C20	117.24 (15)	H15A—C15—H15B	109.5
C17—N3—N2	109.32 (15)	O4—C15—H15C	109.5
C17—N3—C21	122.99 (15)	H15A—C15—H15C	109.5
N2—N3—C21	121.46 (15)	H15B—C15—H15C	109.5
C8—O3—S1	120.47 (11)	C18—C16—N1	122.89 (17)
C13—O4—C15	117.56 (14)	C18—C16—C17	108.18 (15)
C6—C1—C2	118.85 (19)	N1—C16—C17	128.75 (16)
C6—C1—H1	120.6	O5—C17—N3	123.54 (17)
C2—C1—H1	120.6	O5—C17—C16	131.82 (16)
C1—C2—C3	121.21 (19)	N3—C17—C16	104.61 (15)
C1—C2—H2	119.4	N2—C18—C16	110.00 (16)
C3—C2—H2	119.4	N2—C18—C19	122.41 (16)
C4—C3—C2	118.37 (18)	C16—C18—C19	127.59 (16)
C4—C3—C7	119.69 (19)	C18—C19—H19A	109.5
C2—C3—C7	121.94 (18)	C18—C19—H19B	109.5
C3—C4—C5	121.24 (19)	H19A—C19—H19B	109.5
C3—C4—H4	119.4	C18—C19—H19C	109.5
C5—C4—H4	119.4	H19A—C19—H19C	109.5
C6—C5—C4	119.06 (18)	H19B—C19—H19C	109.5
C6—C5—H5	120.5	N2—C20—H20A	109.5
C4—C5—H5	120.5	N2—C20—H20B	109.5
C5—C6—C1	121.23 (18)	H20A—C20—H20B	109.5
C5—C6—S1	119.01 (15)	N2—C20—H20C	109.5
C1—C6—S1	119.70 (15)	H20A—C20—H20C	109.5
C3—C7—H7A	109.5	H20B—C20—H20C	109.5
C3—C7—H7B	109.5	C26—C21—C22	121.04 (19)
H7A—C7—H7B	109.5	C26—C21—N3	118.16 (18)
C3—C7—H7C	109.5	C22—C21—N3	120.72 (19)
H7A—C7—H7C	109.5	C23—C22—C21	118.7 (2)
H7B—C7—H7C	109.5	C23—C22—H22	120.6
C9—C8—C13	120.89 (16)	C21—C22—H22	120.6
C9—C8—O3	120.12 (16)	C24—C23—C22	120.9 (2)
C13—C8—O3	118.86 (16)	C24—C23—H23	119.5
C8—C9—C10	119.79 (17)	C22—C23—H23	119.5
C8—C9—Br1	120.08 (14)	C23—C24—C25	120.1 (2)
C10—C9—Br1	120.13 (14)	C23—C24—H24	119.9
C11—C10—C9	119.84 (18)	C25—C24—H24	119.9
C11—C10—H10	120.1	C24—C25—C26	119.8 (2)
C9—C10—H10	120.1	C24—C25—H25	120.1
C10—C11—C12	120.33 (16)	C26—C25—H25	120.1
C10—C11—C14	118.52 (17)	C21—C26—C25	119.4 (2)
C12—C11—C14	121.15 (16)	C21—C26—H26	120.3
C13—C12—C11	119.80 (16)	C25—C26—H26	120.3
C13—C12—H12	120.1

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O5	0.93	2.30	2.991 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O5	0.93	2.30	2.991 (2)	131