4-(5-Oxo-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzene-sulfonamide.

With respect to the aliphatic planar five-membered ring (r.m.s. deviation = 0.011 Å) of the title compound, C(15)H(13)N(3)O(2)S, the phenyl ring is aligned at 6.9 (1)° and the phenyl-ene ring at 2.4 (1)°, so that the three rings are nearly coplanar. The amino group has the N atom in a pyramidal geometry; the group is a hydrogen-bond donor to the sulfonyl O atom of one mol-ecule and to the ketonic O atom of another mol-ecule, resulting in the formation of a layer parallel to the bc plane.

Related literature

For the synthesis, see: Casoni (1956 ▶); Itano (1955 ▶).

Experimental

Crystal data

C15H13N3O3S

M = 315.34

Monoclinic,

a = 13.6794 (4) Å

b = 13.4304 (4) Å

c = 7.3678 (2) Å

β = 91.055 (3)°

V = 1353.38 (7) Å3

Z = 4

Cu Kα radiation

μ = 2.29 mm−1

T = 100 K

0.30 × 0.05 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.546, T max = 0.894

10404 measured reflections

2731 independent reflections

2444 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.06

2731 reflections

207 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032879/bt5611sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032879/bt5611Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032879/bt5611Isup3.cml

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

C15H13N3O3S	F(000) = 656
Mr = 315.34	Dx = 1.548 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4563 reflections
a = 13.6794 (4) Å	θ = 3.2–74.4°
b = 13.4304 (4) Å	µ = 2.29 mm−1
c = 7.3678 (2) Å	T = 100 K
β = 91.055 (3)°	Prism, brown orange
V = 1353.38 (7) Å3	0.30 × 0.05 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2731 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2444 reflections with I > 2σ(I)
Mirror	Rint = 0.041
Detector resolution: 10.4041 pixels mm-1	θmax = 74.5°, θmin = 3.2°
ω scan	h = −17→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −16→16
Tmin = 0.546, Tmax = 0.894	l = −5→9
10404 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0759P)2 + 0.5321P] where P = (Fo2 + 2Fc2)/3
2731 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.73 e Å−3
2 restraints	Δρmin = −0.51 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.

	x	y	z	Uiso*/Ueq
S1	0.91654 (3)	0.64477 (3)	0.49527 (6)	0.01653 (16)
O1	0.52785 (10)	0.32661 (11)	0.6467 (2)	0.0319 (4)
O2	0.90632 (9)	0.74972 (10)	0.46298 (18)	0.0220 (3)
O3	0.95114 (9)	0.58212 (10)	0.35168 (17)	0.0209 (3)
N2	0.46514 (11)	0.56244 (12)	0.8066 (2)	0.0203 (3)
N3	0.99249 (12)	0.63163 (12)	0.6642 (2)	0.0197 (3)
H1	1.0122 (17)	0.5704 (9)	0.682 (3)	0.028 (6)*
H2	0.9740 (16)	0.6620 (16)	0.763 (2)	0.023 (6)*
N1	0.52929 (11)	0.49471 (11)	0.7246 (2)	0.0197 (3)
C1	0.49011 (14)	0.39912 (14)	0.7147 (3)	0.0227 (4)
C2	0.39264 (14)	0.40640 (14)	0.8033 (3)	0.0224 (4)
H2A	0.3390	0.3864	0.7189	0.027*
H2B	0.3903	0.3645	0.9138	0.027*
C3	0.38673 (13)	0.51403 (14)	0.8491 (2)	0.0198 (4)
C4	0.30272 (13)	0.56293 (14)	0.9324 (2)	0.0205 (4)
C5	0.30792 (15)	0.66235 (15)	0.9877 (3)	0.0261 (4)
H5	0.3663	0.6993	0.9713	0.031*
C6	0.22764 (16)	0.70694 (16)	1.0664 (3)	0.0312 (5)
H6	0.2311	0.7745	1.1040	0.037*
C7	0.14192 (15)	0.65297 (16)	1.0905 (3)	0.0294 (5)
H7	0.0870	0.6837	1.1441	0.035*
C8	0.13695 (14)	0.55477 (17)	1.0363 (3)	0.0281 (5)
H8	0.0784	0.5181	1.0528	0.034*
C9	0.21695 (13)	0.50911 (15)	0.9577 (3)	0.0235 (4)
H9	0.2132	0.4413	0.9213	0.028*
C10	0.62051 (12)	0.52987 (13)	0.6675 (2)	0.0178 (4)
C11	0.68801 (13)	0.46447 (14)	0.5912 (2)	0.0197 (4)
H11	0.6720	0.3961	0.5759	0.024*
C12	0.77831 (13)	0.49990 (13)	0.5381 (2)	0.0184 (4)
H12	0.8246	0.4557	0.4875	0.022*
C13	0.80101 (13)	0.60030 (13)	0.5590 (2)	0.0175 (4)
C14	0.73339 (14)	0.66554 (14)	0.6338 (3)	0.0201 (4)
H14	0.7495	0.7339	0.6481	0.024*
C15	0.64299 (14)	0.63125 (14)	0.6873 (3)	0.0200 (4)
H15	0.5967	0.6759	0.7369	0.024*

	U11	U22	U33	U12	U13	U23
S1	0.0140 (2)	0.0175 (3)	0.0182 (3)	−0.00041 (14)	0.00381 (17)	0.00075 (14)
O1	0.0230 (7)	0.0225 (7)	0.0506 (9)	−0.0015 (6)	0.0103 (7)	−0.0049 (6)
O2	0.0202 (6)	0.0184 (7)	0.0276 (7)	−0.0010 (5)	0.0052 (5)	0.0040 (5)
O3	0.0194 (6)	0.0241 (7)	0.0194 (6)	−0.0005 (5)	0.0061 (5)	−0.0021 (5)
N2	0.0148 (7)	0.0241 (8)	0.0221 (8)	0.0014 (6)	0.0047 (6)	−0.0003 (6)
N3	0.0180 (8)	0.0205 (8)	0.0208 (8)	0.0015 (6)	0.0012 (6)	−0.0009 (6)
N1	0.0161 (7)	0.0206 (8)	0.0226 (8)	−0.0004 (6)	0.0050 (6)	−0.0023 (6)
C1	0.0194 (9)	0.0227 (10)	0.0259 (9)	−0.0017 (7)	0.0013 (7)	0.0021 (7)
C2	0.0179 (9)	0.0251 (10)	0.0242 (9)	−0.0018 (7)	0.0024 (7)	0.0015 (7)
C3	0.0168 (9)	0.0248 (9)	0.0178 (8)	−0.0014 (7)	0.0008 (7)	0.0022 (7)
C4	0.0162 (9)	0.0274 (9)	0.0179 (8)	0.0009 (7)	0.0022 (7)	0.0049 (7)
C5	0.0236 (10)	0.0259 (10)	0.0290 (10)	0.0004 (8)	0.0083 (8)	0.0056 (8)
C6	0.0326 (11)	0.0261 (10)	0.0353 (11)	0.0068 (8)	0.0120 (9)	0.0078 (8)
C7	0.0220 (10)	0.0400 (12)	0.0266 (10)	0.0123 (8)	0.0080 (8)	0.0114 (8)
C8	0.0153 (9)	0.0450 (12)	0.0241 (10)	−0.0017 (8)	0.0019 (7)	0.0068 (8)
C9	0.0180 (9)	0.0329 (10)	0.0195 (9)	−0.0034 (8)	0.0007 (7)	0.0007 (7)
C10	0.0146 (8)	0.0220 (9)	0.0170 (8)	−0.0006 (7)	0.0012 (6)	0.0019 (7)
C11	0.0190 (9)	0.0203 (9)	0.0200 (8)	−0.0009 (7)	0.0019 (7)	−0.0004 (7)
C12	0.0161 (8)	0.0193 (8)	0.0199 (9)	0.0024 (7)	0.0029 (7)	0.0004 (6)
C13	0.0141 (8)	0.0208 (9)	0.0178 (8)	−0.0012 (7)	0.0015 (6)	0.0019 (6)
C14	0.0195 (9)	0.0171 (8)	0.0240 (9)	−0.0002 (7)	0.0033 (7)	0.0000 (7)
C15	0.0177 (9)	0.0211 (9)	0.0213 (9)	0.0017 (7)	0.0029 (7)	−0.0007 (7)

S1—O2	1.4358 (13)	C5—H5	0.9500
S1—O3	1.4386 (13)	C6—C7	1.393 (3)
S1—N3	1.6160 (17)	C6—H6	0.9500
S1—C13	1.7611 (18)	C7—C8	1.379 (3)
O1—C1	1.215 (2)	C7—H7	0.9500
N2—C3	1.298 (2)	C8—C9	1.390 (3)
N2—N1	1.408 (2)	C8—H8	0.9500
N3—H1	0.875 (10)	C9—H9	0.9500
N3—H2	0.873 (10)	C10—C11	1.400 (2)
N1—C1	1.393 (2)	C10—C15	1.403 (3)
N1—C10	1.406 (2)	C11—C12	1.387 (3)
C1—C2	1.499 (3)	C11—H11	0.9500
C2—C3	1.487 (3)	C12—C13	1.392 (2)
C2—H2A	0.9900	C12—H12	0.9500
C2—H2B	0.9900	C13—C14	1.395 (2)
C3—C4	1.468 (2)	C14—C15	1.384 (3)
C4—C9	1.393 (3)	C14—H14	0.9500
C4—C5	1.397 (3)	C15—H15	0.9500
C5—C6	1.387 (3)
O2—S1—O3	119.00 (8)	C5—C6—C7	120.2 (2)
O2—S1—N3	107.10 (8)	C5—C6—H6	119.9
O3—S1—N3	106.67 (8)	C7—C6—H6	119.9
O2—S1—C13	106.97 (8)	C8—C7—C6	119.86 (19)
O3—S1—C13	107.85 (8)	C8—C7—H7	120.1
N3—S1—C13	108.97 (8)	C6—C7—H7	120.1
C3—N2—N1	107.72 (15)	C7—C8—C9	120.49 (19)
S1—N3—H1	114.1 (16)	C7—C8—H8	119.8
S1—N3—H2	113.3 (16)	C9—C8—H8	119.8
H1—N3—H2	114 (2)	C8—C9—C4	119.88 (19)
C1—N1—C10	129.54 (15)	C8—C9—H9	120.1
C1—N1—N2	112.08 (14)	C4—C9—H9	120.1
C10—N1—N2	118.38 (14)	C11—C10—N1	120.35 (16)
O1—C1—N1	126.49 (17)	C11—C10—C15	120.39 (16)
O1—C1—C2	128.35 (18)	N1—C10—C15	119.26 (16)
N1—C1—C2	105.17 (16)	C12—C11—C10	119.71 (17)
C3—C2—C1	102.40 (15)	C12—C11—H11	120.1
C3—C2—H2A	111.3	C10—C11—H11	120.1
C1—C2—H2A	111.3	C11—C12—C13	119.97 (16)
C3—C2—H2B	111.3	C11—C12—H12	120.0
C1—C2—H2B	111.3	C13—C12—H12	120.0
H2A—C2—H2B	109.2	C12—C13—C14	120.26 (16)
N2—C3—C4	122.26 (17)	C12—C13—S1	119.91 (13)
N2—C3—C2	112.57 (16)	C14—C13—S1	119.81 (14)
C4—C3—C2	125.17 (16)	C15—C14—C13	120.41 (17)
C9—C4—C5	119.68 (17)	C15—C14—H14	119.8
C9—C4—C3	119.44 (17)	C13—C14—H14	119.8
C5—C4—C3	120.88 (17)	C14—C15—C10	119.25 (17)
C6—C5—C4	119.85 (19)	C14—C15—H15	120.4
C6—C5—H5	120.1	C10—C15—H15	120.4
C4—C5—H5	120.1
C3—N2—N1—C1	−0.1 (2)	C5—C4—C9—C8	0.5 (3)
C3—N2—N1—C10	−179.52 (16)	C3—C4—C9—C8	−179.92 (17)
C10—N1—C1—O1	−2.7 (3)	C1—N1—C10—C11	−1.6 (3)
N2—N1—C1—O1	177.9 (2)	N2—N1—C10—C11	177.72 (15)
C10—N1—C1—C2	177.83 (17)	C1—N1—C10—C15	178.21 (18)
N2—N1—C1—C2	−1.6 (2)	N2—N1—C10—C15	−2.4 (2)
O1—C1—C2—C3	−177.1 (2)	N1—C10—C11—C12	−178.97 (16)
N1—C1—C2—C3	2.34 (19)	C15—C10—C11—C12	1.2 (3)
N1—N2—C3—C4	−178.03 (16)	C10—C11—C12—C13	−0.7 (3)
N1—N2—C3—C2	1.7 (2)	C11—C12—C13—C14	0.2 (3)
C1—C2—C3—N2	−2.6 (2)	C11—C12—C13—S1	178.85 (14)
C1—C2—C3—C4	177.17 (17)	O2—S1—C13—C12	157.60 (15)
N2—C3—C4—C9	173.44 (17)	O3—S1—C13—C12	28.50 (17)
C2—C3—C4—C9	−6.3 (3)	N3—S1—C13—C12	−86.93 (16)
N2—C3—C4—C5	−7.0 (3)	O2—S1—C13—C14	−23.78 (17)
C2—C3—C4—C5	173.27 (18)	O3—S1—C13—C14	−152.88 (15)
C9—C4—C5—C6	−0.3 (3)	N3—S1—C13—C14	91.69 (16)
C3—C4—C5—C6	−179.88 (18)	C12—C13—C14—C15	−0.3 (3)
C4—C5—C6—C7	0.0 (3)	S1—C13—C14—C15	−178.89 (14)
C5—C6—C7—C8	0.2 (3)	C13—C14—C15—C10	0.8 (3)
C6—C7—C8—C9	0.0 (3)	C11—C10—C15—C14	−1.2 (3)
C7—C8—C9—C4	−0.4 (3)	N1—C10—C15—C14	178.94 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O3i	0.88 (1)	2.12 (1)	2.975 (2)	164 (2)
N3—H2···O2ii	0.87 (1)	2.12 (1)	2.978 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O3i	0.88 (1)	2.12 (1)	2.975 (2)	164 (2)
N3—H2⋯O2ii	0.87 (1)	2.12 (1)	2.978 (2)	168 (2)

Symmetry codes: (i) ; (ii) .