1-[5-(2H-1,3-Benzodioxol-5-yl)-3-(4-methyl-phen-yl)-2-pyrazolin-1-yl]ethanone.

In the title compound, C19H18N2O3, the pyrazoline ring is close to being planar (r.m.s. deviation = 0.035 Å) and subtends dihedral angles of 2.11 (8) and 82.63 (8)° with the p-tolyl and benzene rings, respectively. In the crystal, C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules, forming a three-dimensional network. A weak C-H⋯π inter-action involving the benzene ring is also observed.

Related literature

For background to pyrazoline derivatives, see: Mamolo et al. (2003 ▶); Bansal et al. (2001 ▶); Manna et al. (2005 ▶); Ahn et al. (2004 ▶); Rajendra Prasad et al. (2005 ▶). For a related structure, see: Du (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C19H18N2O3

M = 322.35

Monoclinic,

a = 7.9564 (1) Å

b = 24.1170 (4) Å

c = 8.4660 (1) Å

β = 105.380 (1)°

V = 1566.32 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.984

18850 measured reflections

4828 independent reflections

3778 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.136

S = 1.09

4828 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008817/hb7056sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008817/hb7056Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008817/hb7056Isup3.cml

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

C19H18N2O3	F(000) = 680
Mr = 322.35	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6808 reflections
a = 7.9564 (1) Å	θ = 2.6–30.6°
b = 24.1170 (4) Å	µ = 0.09 mm−1
c = 8.4660 (1) Å	T = 100 K
β = 105.380 (1)°	Block, colourless
V = 1566.32 (4) Å3	0.35 × 0.26 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	4828 independent reflections
Radiation source: fine-focus sealed tube	3778 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 30.7°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→7
Tmin = 0.968, Tmax = 0.984	k = −28→34
18850 measured reflections	l = −12→12

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0389P)2 + 1.3146P] where P = (Fo2 + 2Fc2)/3
4828 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.20199 (17)	0.52198 (5)	0.40364 (15)	0.0242 (3)
O2	0.18293 (16)	0.61783 (5)	0.38140 (14)	0.0204 (3)
O3	0.40078 (16)	0.60685 (5)	−0.20460 (14)	0.0212 (3)
N1	0.54641 (18)	0.67124 (5)	−0.03118 (16)	0.0164 (3)
N2	0.59601 (18)	0.72596 (5)	0.00463 (16)	0.0154 (3)
C1	0.5458 (2)	0.54240 (7)	0.1907 (2)	0.0197 (3)
H1A	0.6263	0.5232	0.1455	0.024*
C2	0.4417 (2)	0.51184 (7)	0.2695 (2)	0.0212 (3)
H2A	0.4504	0.4726	0.2796	0.025*
C3	0.3269 (2)	0.54167 (7)	0.33134 (18)	0.0172 (3)
C4	0.1270 (2)	0.57023 (7)	0.4575 (2)	0.0223 (4)
H4A	0.1669	0.5735	0.5783	0.027*
H4B	−0.0018	0.5676	0.4250	0.027*
C5	0.3156 (2)	0.59905 (6)	0.31861 (18)	0.0157 (3)
C6	0.4180 (2)	0.62926 (6)	0.24358 (18)	0.0156 (3)
H6A	0.4103	0.6685	0.2371	0.019*
C7	0.5353 (2)	0.59965 (6)	0.17627 (18)	0.0163 (3)
C8	0.6489 (2)	0.63082 (7)	0.08798 (19)	0.0172 (3)
H8A	0.7085	0.6040	0.0306	0.021*
C9	0.7850 (2)	0.66945 (7)	0.19965 (19)	0.0178 (3)
H9A	0.7825	0.6660	0.3155	0.021*
H9B	0.9041	0.6611	0.1910	0.021*
C10	0.7271 (2)	0.72633 (7)	0.13314 (18)	0.0156 (3)
C11	0.8090 (2)	0.77833 (7)	0.20273 (18)	0.0157 (3)
C12	0.9503 (2)	0.77802 (7)	0.34314 (19)	0.0181 (3)
H12A	0.9944	0.7438	0.3928	0.022*
C13	1.0259 (2)	0.82764 (7)	0.40982 (19)	0.0197 (3)
H13A	1.1210	0.8268	0.5053	0.024*
C14	0.9654 (2)	0.87859 (7)	0.34000 (19)	0.0185 (3)
C15	0.8254 (2)	0.87857 (7)	0.19888 (19)	0.0184 (3)
H15A	0.7829	0.9128	0.1481	0.022*
C16	0.7481 (2)	0.82948 (7)	0.13228 (18)	0.0174 (3)
H16A	0.6523	0.8305	0.0373	0.021*
C17	0.4283 (2)	0.65621 (7)	−0.17337 (18)	0.0163 (3)
C18	0.3369 (2)	0.70214 (7)	−0.28355 (19)	0.0188 (3)
H18A	0.2313	0.6875	−0.3600	0.028*
H18B	0.4147	0.7172	−0.3453	0.028*
H18C	0.3051	0.7316	−0.2171	0.028*
C19	1.0460 (2)	0.93221 (7)	0.4153 (2)	0.0246 (4)
H19A	1.1729	0.9302	0.4352	0.037*
H19B	1.0166	0.9383	0.5193	0.037*
H19C	1.0008	0.9630	0.3404	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0277 (7)	0.0191 (6)	0.0290 (6)	−0.0026 (5)	0.0129 (5)	0.0007 (5)
O2	0.0195 (6)	0.0193 (6)	0.0251 (6)	0.0014 (5)	0.0105 (5)	−0.0008 (5)
O3	0.0242 (6)	0.0163 (6)	0.0221 (5)	−0.0015 (5)	0.0045 (5)	−0.0032 (4)
N1	0.0187 (7)	0.0131 (6)	0.0164 (6)	−0.0010 (5)	0.0030 (5)	0.0003 (5)
N2	0.0162 (7)	0.0136 (6)	0.0172 (6)	−0.0019 (5)	0.0061 (5)	−0.0016 (5)
C1	0.0212 (8)	0.0160 (7)	0.0217 (7)	0.0044 (6)	0.0055 (6)	−0.0013 (6)
C2	0.0261 (9)	0.0128 (7)	0.0242 (7)	0.0008 (6)	0.0059 (7)	0.0023 (6)
C3	0.0175 (8)	0.0174 (7)	0.0162 (7)	−0.0035 (6)	0.0031 (6)	0.0011 (6)
C4	0.0223 (9)	0.0236 (8)	0.0221 (7)	−0.0027 (7)	0.0078 (7)	−0.0021 (6)
C5	0.0140 (7)	0.0167 (7)	0.0148 (6)	0.0017 (6)	0.0010 (6)	−0.0023 (5)
C6	0.0164 (8)	0.0116 (7)	0.0173 (6)	0.0016 (6)	0.0017 (6)	−0.0012 (5)
C7	0.0170 (8)	0.0157 (7)	0.0146 (6)	−0.0005 (6)	0.0016 (6)	0.0006 (5)
C8	0.0172 (8)	0.0163 (7)	0.0177 (7)	0.0025 (6)	0.0042 (6)	0.0012 (6)
C9	0.0151 (8)	0.0182 (7)	0.0193 (7)	−0.0003 (6)	0.0032 (6)	0.0011 (6)
C10	0.0152 (8)	0.0179 (7)	0.0155 (6)	−0.0006 (6)	0.0072 (6)	0.0000 (6)
C11	0.0139 (7)	0.0191 (7)	0.0156 (6)	−0.0018 (6)	0.0067 (6)	−0.0009 (6)
C12	0.0156 (8)	0.0199 (8)	0.0192 (7)	0.0012 (6)	0.0053 (6)	0.0003 (6)
C13	0.0154 (8)	0.0241 (8)	0.0185 (7)	−0.0011 (6)	0.0023 (6)	−0.0031 (6)
C14	0.0170 (8)	0.0200 (8)	0.0197 (7)	−0.0015 (6)	0.0068 (6)	−0.0041 (6)
C15	0.0190 (8)	0.0178 (8)	0.0190 (7)	0.0019 (6)	0.0060 (6)	−0.0005 (6)
C16	0.0163 (8)	0.0208 (8)	0.0152 (6)	−0.0011 (6)	0.0042 (6)	−0.0005 (6)
C17	0.0169 (8)	0.0175 (7)	0.0165 (6)	−0.0001 (6)	0.0080 (6)	−0.0017 (6)
C18	0.0188 (8)	0.0189 (8)	0.0177 (7)	−0.0010 (6)	0.0028 (6)	0.0003 (6)
C19	0.0242 (9)	0.0218 (8)	0.0263 (8)	−0.0016 (7)	0.0041 (7)	−0.0060 (7)

O1—C3	1.382 (2)	C9—C10	1.508 (2)
O1—C4	1.436 (2)	C9—H9A	0.9900
O2—C5	1.378 (2)	C9—H9B	0.9900
O2—C4	1.443 (2)	C10—C11	1.463 (2)
O3—C17	1.2265 (19)	C11—C16	1.399 (2)
N1—C17	1.3651 (19)	C11—C12	1.403 (2)
N1—N2	1.3877 (18)	C12—C13	1.390 (2)
N1—C8	1.482 (2)	C12—H12A	0.9500
N2—C10	1.292 (2)	C13—C14	1.393 (2)
C1—C7	1.387 (2)	C13—H13A	0.9500
C1—C2	1.403 (2)	C14—C15	1.401 (2)
C1—H1A	0.9500	C14—C19	1.508 (2)
C2—C3	1.371 (2)	C15—C16	1.383 (2)
C2—H2A	0.9500	C15—H15A	0.9500
C3—C5	1.389 (2)	C16—H16A	0.9500
C4—H4A	0.9900	C17—C18	1.506 (2)
C4—H4B	0.9900	C18—H18A	0.9800
C5—C6	1.369 (2)	C18—H18B	0.9800
C6—C7	1.410 (2)	C18—H18C	0.9800
C6—H6A	0.9500	C19—H19A	0.9800
C7—C8	1.516 (2)	C19—H19B	0.9800
C8—C9	1.546 (2)	C19—H19C	0.9800
C8—H8A	1.0000
C3—O1—C4	105.69 (13)	C10—C9—H9B	111.2
C5—O2—C4	105.61 (13)	C8—C9—H9B	111.2
C17—N1—N2	122.31 (13)	H9A—C9—H9B	109.1
C17—N1—C8	123.46 (13)	N2—C10—C11	121.24 (14)
N2—N1—C8	113.80 (12)	N2—C10—C9	113.99 (14)
C10—N2—N1	108.04 (13)	C11—C10—C9	124.76 (13)
C7—C1—C2	122.41 (16)	C16—C11—C12	118.35 (14)
C7—C1—H1A	118.8	C16—C11—C10	121.13 (14)
C2—C1—H1A	118.8	C12—C11—C10	120.52 (14)
C3—C2—C1	116.31 (15)	C13—C12—C11	120.18 (15)
C3—C2—H2A	121.8	C13—C12—H12A	119.9
C1—C2—H2A	121.8	C11—C12—H12A	119.9
C2—C3—O1	128.25 (15)	C12—C13—C14	121.57 (14)
C2—C3—C5	121.95 (16)	C12—C13—H13A	119.2
O1—C3—C5	109.69 (15)	C14—C13—H13A	119.2
O1—C4—O2	107.41 (13)	C13—C14—C15	117.95 (15)
O1—C4—H4A	110.2	C13—C14—C19	121.13 (14)
O2—C4—H4A	110.2	C15—C14—C19	120.92 (15)
O1—C4—H4B	110.2	C16—C15—C14	120.99 (15)
O2—C4—H4B	110.2	C16—C15—H15A	119.5
H4A—C4—H4B	108.5	C14—C15—H15A	119.5
C6—C5—O2	127.96 (14)	C15—C16—C11	120.96 (14)
C6—C5—C3	122.14 (15)	C15—C16—H16A	119.5
O2—C5—C3	109.77 (14)	C11—C16—H16A	119.5
C5—C6—C7	117.22 (14)	O3—C17—N1	119.32 (14)
C5—C6—H6A	121.4	O3—C17—C18	123.45 (14)
C7—C6—H6A	121.4	N1—C17—C18	117.23 (14)
C1—C7—C6	119.95 (15)	C17—C18—H18A	109.5
C1—C7—C8	120.50 (15)	C17—C18—H18B	109.5
C6—C7—C8	119.54 (14)	H18A—C18—H18B	109.5
N1—C8—C7	111.69 (13)	C17—C18—H18C	109.5
N1—C8—C9	100.92 (12)	H18A—C18—H18C	109.5
C7—C8—C9	114.17 (13)	H18B—C18—H18C	109.5
N1—C8—H8A	109.9	C14—C19—H19A	109.5
C7—C8—H8A	109.9	C14—C19—H19B	109.5
C9—C8—H8A	109.9	H19A—C19—H19B	109.5
C10—C9—C8	102.99 (12)	C14—C19—H19C	109.5
C10—C9—H9A	111.2	H19A—C19—H19C	109.5
C8—C9—H9A	111.2	H19B—C19—H19C	109.5
C17—N1—N2—C10	−170.21 (15)	C1—C7—C8—C9	−114.22 (16)
C8—N1—N2—C10	2.53 (18)	C6—C7—C8—C9	66.00 (18)
C7—C1—C2—C3	0.5 (2)	N1—C8—C9—C10	4.62 (16)
C1—C2—C3—O1	175.04 (15)	C7—C8—C9—C10	−115.32 (15)
C1—C2—C3—C5	−0.8 (2)	N1—N2—C10—C11	−179.57 (14)
C4—O1—C3—C2	175.73 (16)	N1—N2—C10—C9	1.01 (19)
C4—O1—C3—C5	−8.00 (17)	C8—C9—C10—N2	−3.82 (19)
C3—O1—C4—O2	13.04 (16)	C8—C9—C10—C11	176.78 (15)
C5—O2—C4—O1	−13.22 (16)	N2—C10—C11—C16	0.0 (2)
C4—O2—C5—C6	−175.69 (15)	C9—C10—C11—C16	179.32 (16)
C4—O2—C5—C3	8.42 (16)	N2—C10—C11—C12	179.46 (16)
C2—C3—C5—C6	0.1 (2)	C9—C10—C11—C12	−1.2 (2)
O1—C3—C5—C6	−176.47 (13)	C16—C11—C12—C13	0.4 (2)
C2—C3—C5—O2	176.25 (14)	C10—C11—C12—C13	−179.11 (15)
O1—C3—C5—O2	−0.30 (17)	C11—C12—C13—C14	−0.4 (3)
O2—C5—C6—C7	−174.44 (14)	C12—C13—C14—C15	−0.3 (3)
C3—C5—C6—C7	1.0 (2)	C12—C13—C14—C19	178.74 (16)
C2—C1—C7—C6	0.6 (2)	C13—C14—C15—C16	0.9 (3)
C2—C1—C7—C8	−179.21 (14)	C19—C14—C15—C16	−178.14 (16)
C5—C6—C7—C1	−1.3 (2)	C14—C15—C16—C11	−0.8 (3)
C5—C6—C7—C8	178.49 (13)	C12—C11—C16—C15	0.2 (2)
C17—N1—C8—C7	−70.29 (19)	C10—C11—C16—C15	179.70 (15)
N2—N1—C8—C7	117.07 (14)	N2—N1—C17—O3	173.77 (15)
C17—N1—C8—C9	168.00 (15)	C8—N1—C17—O3	1.7 (2)
N2—N1—C8—C9	−4.64 (17)	N2—N1—C17—C18	−6.8 (2)
C1—C7—C8—N1	132.07 (15)	C8—N1—C17—C18	−178.84 (15)
C6—C7—C8—N1	−47.70 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3i	0.95	2.42	3.229 (2)	142
C4—H4A···O3ii	0.99	2.38	3.225 (2)	143
C9—H9B···O2iii	0.99	2.59	3.371 (2)	136
C18—H18B···N2iv	0.98	2.56	3.526 (2)	169
C19—H19A···O3v	0.98	2.57	3.377 (2)	139
C19—H19A···Cg1vi	0.98	2.93	3.6013 (18)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C3/C5–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3i	0.95	2.42	3.229 (2)	142
C4—H4A⋯O3ii	0.99	2.38	3.225 (2)	143
C9—H9B⋯O2iii	0.99	2.59	3.371 (2)	136
C18—H18B⋯N2iv	0.98	2.56	3.526 (2)	169
C19—H19A⋯O3v	0.98	2.57	3.377 (2)	139
C19—H19A⋯Cg1vi	0.98	2.93	3.6013 (18)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .