2,5-Dichloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)­benzene­sulfonamide

In the title compound, C₁₇H₁₅Cl₂N₃O₃S, the dihedral angle between the mean planes of the pyrazole and phenyl rings is 41.5 (2)°. The dichloro­benzene ring and the pyrazole residue form a C—N—S—C torsion angle of 70.3 (3)°. One inter­molecular N—H...O and two inter­molecular C—H...O hydrogen bonds are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.096
• wR factor = 0.270
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.270
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.102
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT084_ALERT_2_C High R2 Value ..................................       0.27
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.15
PLAT318_ALERT_2_C Check Hybridisation of  N1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  N3      ..       3.23 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

4-aminoantipyrine and its complexes are known for their variety of applications in the area of catalysis (Bernardo et al., 1996; Punniyamurthy et al., 1995), clinical applications (Chiaramonte et al., 2003), and pharmacology (Torayama et al., 1997). We have focused our research on investigation of different heterocyclic systems based on sulfonamide pharmacophoric group and metal complexes searching new lead compounds with antiparasitic activity. In the light of this interest, we describe here an crystallographic study of the title compound, (I).

The C7—N1—S1—C1 torsion angle between the pyrazole moiety and the dichlorbenzene ring is 70.3 (3)°. The phenyl ring and the pyrazole residue are twisted to each other by an angle of 41.5 (2)° between the mean planes. The N—H H atom has an intermolecular hydrogen bond to O3 [N—H···O = 2.03 Å]. The two sulfonamide oxygen atoms O1 and O2 are involved in non-classical intermolecular hydrogen bonds with C3 and C11 [C—H···O = 2.51 Å, C—H···O = 2.48 Å, respectively] (Table 1).

Related literature

For related literature, see: Bernardo et al. (1996); Chiaramonte et al. (2003); Punniyamurthy et al. (1995); Torayama et al. (1997); Xue et al. (2000).

S2. Experimental

Compound (I) was prepared according to a literature procedure (Xue et al., 2000). Suitable crystals were obtained by recrystallization from methanol-dichloromethane (1:1).

S3. Refinement

The C—H atoms were positioned with idealized geometry and refined using a riding model with C—H in the range 0.93–0.96 Å. The N—H H atoms were initially located in difference map, which shows that the nitrogen atom is nearly planar. Finally the N—H atoms were positioned with idealized geometry and refined using a riding model with N—H = 0.86 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U_eq of the parent atom). All crystals investigated exhibits very broad reflection profiles and thus were of low crystal quality, which might be the reason for the bad reliability factors.

Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. Molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level.

2,5-DichloroN-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H- pyrazol-4-yl)benzenesulfonamide

Crystal data

C17H15Cl2N3O3S	Z = 2
Mr = 412.28	F(000) = 424
Triclinic, P1	Dx = 1.551 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.009 (2) Å	Cell parameters from 25 reflections
b = 10.697 (3) Å	θ = 5.3–18.7°
c = 11.201 (5) Å	µ = 4.63 mm^−1
α = 102.17 (3)°	T = 299 K
β = 92.23 (2)°	Prism, colorless
γ = 108.69 (3)°	0.45 × 0.38 × 0.13 mm
V = 882.7 (5) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	2692 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.102
Graphite monochromator	θmax = 66.9°, θmin = 4.1°
ω/2θ scans	h = −9→9
Absorption correction: psi-scan (North et al., 1968)	k = −12→12
Tmin = 0.180, Tmax = 0.545	l = −13→2
3679 measured reflections	3 standard reflections every 120 min
3139 independent reflections	intensity decay: 1.0%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.096	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.270	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
3139 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 1.15 e Å^−3
0 restraints	Δρmin = −0.93 e Å^−3

Special details

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2506 (5)	0.6027 (4)	0.3252 (4)	0.0406 (9)
C2	0.4235 (5)	0.6088 (4)	0.3586 (4)	0.0447 (9)
C3	0.5105 (6)	0.5429 (5)	0.2785 (5)	0.0520 (11)
H3	0.6247	0.5465	0.3027	0.062*
C4	0.4290 (6)	0.4715 (5)	0.1624 (5)	0.0525 (11)
H4	0.4874	0.4265	0.1079	0.063*
C5	0.2600 (6)	0.4674 (4)	0.1280 (4)	0.0449 (9)
C6	0.1701 (6)	0.5323 (4)	0.2073 (4)	0.0443 (10)
H6	0.0565	0.5290	0.1821	0.053*
C7	0.2173 (5)	0.9206 (4)	0.3645 (4)	0.0371 (8)
C8	0.0806 (5)	0.9498 (4)	0.3131 (4)	0.0414 (9)
C9	0.3788 (5)	0.9952 (4)	0.3207 (4)	0.0381 (8)
C10	0.4284 (6)	1.1241 (4)	0.1575 (4)	0.0430 (9)
C11	0.6038 (6)	1.2059 (4)	0.1939 (5)	0.0488 (10)
H11	0.6519	1.2274	0.2756	0.059*
C12	0.7050 (7)	1.2546 (5)	0.1065 (5)	0.0589 (12)
H12	0.8241	1.3066	0.1289	0.071*
C13	0.6322 (8)	1.2275 (5)	−0.0142 (5)	0.0616 (13)
H13	0.7017	1.2620	−0.0721	0.074*
C14	0.4574 (8)	1.1494 (5)	−0.0480 (5)	0.0605 (12)
H14	0.4082	1.1317	−0.1289	0.073*
C15	0.3541 (7)	1.0971 (5)	0.0370 (4)	0.0511 (10)
H15	0.2355	1.0441	0.0139	0.061*
C16	−0.1099 (6)	0.9038 (5)	0.3355 (5)	0.0557 (12)
H16A	−0.1217	0.8644	0.4055	0.067*
H16B	−0.1795	0.8374	0.2645	0.067*
H16C	−0.1508	0.9802	0.3510	0.067*
C17	0.0771 (7)	1.1450 (5)	0.2313 (6)	0.0620 (13)
H17C	0.1435	1.1976	0.1785	0.074*
H17B	0.0936	1.2011	0.3128	0.074*
H17A	−0.0466	1.1110	0.2005	0.074*
N1	0.2147 (4)	0.8422 (3)	0.4515 (3)	0.0377 (7)
H1A	0.2656	0.8841	0.5246	0.045*
N2	0.1397 (4)	1.0301 (4)	0.2342 (4)	0.0456 (9)
N3	0.3272 (4)	1.0676 (4)	0.2471 (3)	0.0434 (8)
O1	−0.0439 (4)	0.6444 (3)	0.3520 (3)	0.0525 (8)
O2	0.1325 (4)	0.6469 (3)	0.5388 (3)	0.0546 (8)
O3	0.5322 (3)	0.9969 (3)	0.3430 (3)	0.0441 (7)
Cl1	0.53256 (15)	0.69729 (13)	0.50285 (11)	0.0617 (5)
Cl2	0.15602 (17)	0.37735 (13)	−0.01848 (11)	0.0634 (5)
S1	0.12324 (12)	0.67997 (9)	0.42367 (9)	0.0404 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0293 (19)	0.0222 (17)	0.064 (2)	0.0068 (14)	−0.0029 (16)	0.0015 (15)
C2	0.031 (2)	0.0317 (19)	0.065 (2)	0.0093 (16)	−0.0046 (17)	0.0002 (17)
C3	0.031 (2)	0.039 (2)	0.082 (3)	0.0129 (18)	0.0001 (19)	0.005 (2)
C4	0.040 (2)	0.036 (2)	0.079 (3)	0.0144 (19)	0.008 (2)	0.004 (2)
C5	0.041 (2)	0.0269 (18)	0.060 (2)	0.0090 (16)	−0.0018 (17)	0.0019 (16)
C6	0.032 (2)	0.0279 (18)	0.068 (3)	0.0088 (15)	−0.0054 (17)	0.0036 (17)
C7	0.0240 (18)	0.0249 (17)	0.057 (2)	0.0073 (14)	0.0007 (15)	0.0002 (15)
C8	0.0286 (19)	0.0292 (18)	0.063 (2)	0.0134 (15)	0.0006 (16)	−0.0013 (16)
C9	0.0275 (19)	0.0260 (17)	0.056 (2)	0.0094 (15)	−0.0015 (15)	−0.0007 (15)
C10	0.037 (2)	0.0302 (19)	0.060 (2)	0.0135 (16)	0.0013 (17)	0.0030 (16)
C11	0.044 (2)	0.033 (2)	0.067 (3)	0.0127 (18)	0.0016 (19)	0.0065 (18)
C12	0.050 (3)	0.038 (2)	0.087 (3)	0.010 (2)	0.013 (2)	0.018 (2)
C13	0.072 (3)	0.042 (2)	0.083 (3)	0.028 (2)	0.025 (3)	0.023 (2)
C14	0.078 (4)	0.047 (3)	0.064 (3)	0.033 (3)	0.007 (2)	0.011 (2)
C15	0.050 (3)	0.037 (2)	0.062 (3)	0.0172 (19)	−0.006 (2)	0.0024 (18)
C16	0.026 (2)	0.053 (3)	0.091 (3)	0.0184 (19)	0.005 (2)	0.014 (2)
C17	0.044 (3)	0.046 (3)	0.101 (4)	0.024 (2)	0.000 (2)	0.016 (3)
N1	0.0257 (15)	0.0237 (15)	0.0546 (18)	0.0039 (12)	−0.0041 (12)	−0.0013 (13)
N2	0.0238 (17)	0.0402 (19)	0.072 (2)	0.0145 (15)	−0.0032 (14)	0.0084 (16)
N3	0.0253 (16)	0.0352 (17)	0.067 (2)	0.0090 (14)	−0.0029 (14)	0.0091 (15)
O1	0.0225 (14)	0.0358 (15)	0.084 (2)	0.0042 (12)	−0.0057 (13)	−0.0066 (14)
O2	0.0431 (18)	0.0384 (16)	0.079 (2)	0.0088 (13)	0.0110 (14)	0.0131 (15)
O3	0.0249 (14)	0.0383 (15)	0.0647 (17)	0.0119 (12)	−0.0030 (11)	0.0022 (12)
Cl1	0.0370 (7)	0.0592 (8)	0.0747 (8)	0.0170 (5)	−0.0131 (5)	−0.0118 (6)
Cl2	0.0586 (8)	0.0551 (8)	0.0669 (8)	0.0218 (6)	−0.0068 (6)	−0.0079 (5)
S1	0.0240 (6)	0.0258 (6)	0.0648 (7)	0.0048 (4)	0.0011 (4)	0.0029 (4)

Geometric parameters (Å, º)

C1—C6	1.389 (6)	C11—C12	1.376 (7)
C1—C2	1.397 (5)	C11—H11	0.9300
C1—S1	1.785 (4)	C12—C13	1.385 (8)
C2—C3	1.373 (7)	C12—H12	0.9300
C2—Cl1	1.727 (4)	C13—C14	1.370 (8)
C3—C4	1.377 (7)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.376 (8)
C4—C5	1.378 (6)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.378 (6)	C16—H16A	0.9600
C5—Cl2	1.739 (4)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—C8	1.368 (5)	C17—N2	1.473 (5)
C7—N1	1.410 (5)	C17—H17C	0.9600
C7—C9	1.450 (5)	C17—H17B	0.9600
C8—N2	1.355 (6)	C17—H17A	0.9600
C8—C16	1.495 (6)	N1—S1	1.608 (3)
C9—O3	1.237 (4)	N1—H1A	0.8600
C9—N3	1.377 (5)	N2—N3	1.418 (4)
C10—C15	1.386 (7)	O1—S1	1.429 (3)
C10—C11	1.386 (6)	O2—S1	1.412 (4)
C10—N3	1.427 (6)
C6—C1—C2	118.6 (4)	C14—C13—C12	119.7 (5)
C6—C1—S1	116.8 (3)	C14—C13—H13	120.1
C2—C1—S1	124.6 (3)	C12—C13—H13	120.1
C3—C2—C1	121.0 (4)	C13—C14—C15	120.5 (5)
C3—C2—Cl1	118.1 (3)	C13—C14—H14	119.8
C1—C2—Cl1	120.9 (3)	C15—C14—H14	119.8
C2—C3—C4	120.1 (4)	C14—C15—C10	119.4 (5)
C2—C3—H3	119.9	C14—C15—H15	120.3
C4—C3—H3	119.9	C10—C15—H15	120.3
C3—C4—C5	119.2 (4)	C8—C16—H16A	109.5
C3—C4—H4	120.4	C8—C16—H16B	109.5
C5—C4—H4	120.4	H16A—C16—H16B	109.5
C4—C5—C6	121.5 (4)	C8—C16—H16C	109.5
C4—C5—Cl2	119.5 (4)	H16A—C16—H16C	109.5
C6—C5—Cl2	119.0 (3)	H16B—C16—H16C	109.5
C5—C6—C1	119.5 (4)	N2—C17—H17C	109.5
C5—C6—H6	120.2	N2—C17—H17B	109.5
C1—C6—H6	120.2	H17C—C17—H17B	109.5
C8—C7—N1	129.1 (4)	N2—C17—H17A	109.5
C8—C7—C9	107.5 (4)	H17C—C17—H17A	109.5
N1—C7—C9	123.3 (3)	H17B—C17—H17A	109.5
N2—C8—C7	110.5 (4)	C7—N1—S1	124.6 (3)
N2—C8—C16	121.7 (4)	C7—N1—H1A	117.7
C7—C8—C16	127.8 (4)	S1—N1—H1A	117.7
O3—C9—N3	125.7 (4)	C8—N2—N3	106.6 (3)
O3—C9—C7	129.0 (4)	C8—N2—C17	120.7 (4)
N3—C9—C7	105.2 (3)	N3—N2—C17	113.2 (3)
C15—C10—C11	120.9 (4)	C9—N3—N2	109.5 (3)
C15—C10—N3	121.0 (4)	C9—N3—C10	124.7 (3)
C11—C10—N3	118.1 (4)	N2—N3—C10	120.9 (3)
C12—C11—C10	118.5 (5)	O2—S1—O1	120.7 (2)
C12—C11—H11	120.8	O2—S1—N1	105.36 (19)
C10—C11—H11	120.8	O1—S1—N1	107.72 (18)
C11—C12—C13	121.0 (5)	O2—S1—C1	109.1 (2)
C11—C12—H12	119.5	O1—S1—C1	104.75 (19)
C13—C12—H12	119.5	N1—S1—C1	108.86 (18)
C6—C1—C2—C3	−2.2 (6)	N3—C10—C15—C14	−177.8 (4)
S1—C1—C2—C3	177.9 (3)	C8—C7—N1—S1	70.4 (5)
C6—C1—C2—Cl1	178.8 (3)	C9—C7—N1—S1	−114.7 (4)
S1—C1—C2—Cl1	−1.0 (5)	C7—C8—N2—N3	−7.3 (5)
C1—C2—C3—C4	1.2 (7)	C16—C8—N2—N3	172.7 (4)
Cl1—C2—C3—C4	−179.8 (4)	C7—C8—N2—C17	−138.1 (4)
C2—C3—C4—C5	0.1 (7)	C16—C8—N2—C17	41.8 (6)
C3—C4—C5—C6	−0.5 (7)	O3—C9—N3—N2	174.6 (4)
C3—C4—C5—Cl2	−180.0 (4)	C7—C9—N3—N2	−5.8 (4)
C4—C5—C6—C1	−0.5 (6)	O3—C9—N3—C10	19.4 (6)
Cl2—C5—C6—C1	179.0 (3)	C7—C9—N3—C10	−161.1 (4)
C2—C1—C6—C5	1.8 (6)	C8—N2—N3—C9	8.2 (5)
S1—C1—C6—C5	−178.3 (3)	C17—N2—N3—C9	143.2 (4)
N1—C7—C8—N2	179.3 (4)	C8—N2—N3—C10	164.6 (4)
C9—C7—C8—N2	3.7 (5)	C17—N2—N3—C10	−60.5 (5)
N1—C7—C8—C16	−0.7 (7)	C15—C10—N3—C9	127.2 (4)
C9—C7—C8—C16	−176.3 (4)	C11—C10—N3—C9	−52.3 (6)
C8—C7—C9—O3	−179.0 (4)	C15—C10—N3—N2	−25.4 (6)
N1—C7—C9—O3	5.1 (6)	C11—C10—N3—N2	155.0 (4)
C8—C7—C9—N3	1.4 (4)	C7—N1—S1—O2	−172.8 (3)
N1—C7—C9—N3	−174.4 (3)	C7—N1—S1—O1	−42.8 (4)
C15—C10—C11—C12	−3.1 (6)	C7—N1—S1—C1	70.3 (3)
N3—C10—C11—C12	176.5 (4)	C6—C1—S1—O2	132.0 (3)
C10—C11—C12—C13	2.6 (7)	C2—C1—S1—O2	−48.2 (4)
C11—C12—C13—C14	−0.9 (8)	C6—C1—S1—O1	1.5 (4)
C12—C13—C14—C15	−0.5 (7)	C2—C1—S1—O1	−178.7 (4)
C13—C14—C15—C10	0.0 (7)	C6—C1—S1—N1	−113.5 (3)
C11—C10—C15—C14	1.8 (6)	C2—C1—S1—N1	66.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.86	2.03	2.846 (4)	157
C3—H3···O1^ii	0.93	2.51	3.392 (5)	158
C11—H11···O2^i	0.93	2.48	3.360 (6)	157

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z.