3-[5-(2,4-Dichloro-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-4-hy-droxy-2H-chromen-2-one.

In the title compound, C(24)H(16)Cl(2)N(2)O(3), the chromene ring system is almost planar, with a maximum deviation of 0.042 (1) Å. It makes dihedral angles of 3.72 (6), 73.37 (5) and 12.00 (5)° with the dihydro-pyrazole, benzene and phenyl rings, respectively. An intra-molecular O-H⋯N hydrogen bond forms an S(6) ring motif. In the crystal, mol-ecules are linked via C-H⋯O inter-actions, forming an infinite chain along the a axis. The crystal packing is further stabilized by a π-π stacking inter-action [centroid-centroid distance = 3.5471 (7) Å] and a Cl⋯Cl short contact [Cl⋯Cl = 3.214 (1) Å].

Related literature

For a related structure, see: Asad et al. (2010 ▶). For the biological activity of pyrazoline derivatives, see: Bernstein et al. (1947 ▶); Chimenti et al. (2004 ▶); Goodell et al. (2006 ▶); Hollis et al. (1984 ▶); Mohammad et al. (2008 ▶); Siddiqui et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C24H16Cl2N2O3

M = 451.29

Triclinic,

a = 6.2583 (2) Å

b = 11.5136 (5) Å

c = 14.2248 (5) Å

α = 87.242 (1)°

β = 88.821 (1)°

γ = 76.181 (1)°

V = 994.11 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 100 K

0.46 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.852, T max = 0.955

22849 measured reflections

5747 independent reflections

5151 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.03

5747 reflections

284 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.11 e Å−3

Δρmin = −0.88 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001590/is2660sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001590/is2660Isup2.hkl

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

C24H16Cl2N2O3	Z = 2
Mr = 451.29	F(000) = 464
Triclinic, P1	Dx = 1.508 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2583 (2) Å	Cell parameters from 9965 reflections
b = 11.5136 (5) Å	θ = 2.3–32.7°
c = 14.2248 (5) Å	µ = 0.36 mm−1
α = 87.242 (1)°	T = 100 K
β = 88.821 (1)°	Block, yellow
γ = 76.181 (1)°	0.46 × 0.15 × 0.13 mm
V = 994.11 (6) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5747 independent reflections
Radiation source: fine-focus sealed tube	5151 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.852, Tmax = 0.955	k = −16→16
22849 measured reflections	l = −20→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.7425P] where P = (Fo2 + 2Fc2)/3
5747 reflections	(Δ/σ)max = 0.001
284 parameters	Δρmax = 1.11 e Å−3
0 restraints	Δρmin = −0.88 e Å−3

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

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.35949 (7)	0.90740 (4)	0.03853 (2)	0.03009 (10)
Cl2	−0.14981 (8)	0.62457 (3)	−0.06976 (3)	0.03714 (11)
O1	0.71612 (15)	0.58755 (9)	0.51861 (7)	0.01973 (19)
O2	0.72747 (16)	0.66920 (10)	0.37635 (7)	0.0251 (2)
O3	0.06651 (15)	0.75993 (9)	0.55672 (7)	0.02046 (19)
N1	0.07093 (17)	0.86134 (9)	0.39234 (7)	0.0162 (2)
N2	−0.00154 (18)	0.92564 (10)	0.31061 (7)	0.0192 (2)
C1	0.6146 (2)	0.66136 (11)	0.44534 (9)	0.0177 (2)
C2	0.6117 (2)	0.57587 (11)	0.60307 (9)	0.0173 (2)
C3	0.7375 (2)	0.50505 (11)	0.67383 (10)	0.0205 (2)
H3A	0.8836	0.4664	0.6630	0.025*
C4	0.6386 (2)	0.49384 (12)	0.76082 (10)	0.0217 (3)
H4A	0.7202	0.4476	0.8091	0.026*
C5	0.4182 (2)	0.55092 (12)	0.77721 (9)	0.0218 (3)
H5A	0.3550	0.5431	0.8362	0.026*
C6	0.2942 (2)	0.61889 (12)	0.70583 (9)	0.0203 (2)
H6A	0.1469	0.6555	0.7164	0.024*
C7	0.3911 (2)	0.63252 (11)	0.61735 (9)	0.0170 (2)
C8	0.2763 (2)	0.70665 (11)	0.54083 (9)	0.0164 (2)
C9	0.38412 (19)	0.72235 (11)	0.45724 (8)	0.0156 (2)
C10	0.2732 (2)	0.80047 (11)	0.38073 (8)	0.0153 (2)
C11	0.3638 (2)	0.82338 (11)	0.28433 (9)	0.0168 (2)
H11A	0.4255	0.7491	0.2538	0.020*
H11B	0.4754	0.8688	0.2875	0.020*
C12	0.1564 (2)	0.89691 (11)	0.23291 (8)	0.0157 (2)
H12A	0.1858	0.9707	0.2043	0.019*
C13	0.07859 (19)	0.82708 (11)	0.15820 (9)	0.0153 (2)
C14	−0.0757 (2)	0.75932 (11)	0.17822 (10)	0.0199 (2)
H14A	−0.1327	0.7566	0.2390	0.024*
C15	−0.1455 (2)	0.69604 (12)	0.10939 (11)	0.0248 (3)
H15A	−0.2486	0.6514	0.1237	0.030*
C16	−0.0596 (2)	0.69996 (12)	0.01883 (10)	0.0244 (3)
C17	0.0968 (2)	0.76382 (12)	−0.00390 (10)	0.0243 (3)
H17A	0.1558	0.7648	−0.0644	0.029*
C18	0.1630 (2)	0.82658 (12)	0.06681 (9)	0.0189 (2)
C19	−0.2083 (2)	1.00293 (10)	0.30513 (8)	0.0154 (2)
C20	−0.3406 (2)	1.03064 (11)	0.38552 (9)	0.0177 (2)
H20A	−0.2880	0.9997	0.4444	0.021*
C21	−0.5506 (2)	1.10448 (12)	0.37687 (9)	0.0201 (2)
H21A	−0.6383	1.1216	0.4304	0.024*
C22	−0.6326 (2)	1.15338 (12)	0.28987 (10)	0.0212 (2)
H22A	−0.7743	1.2018	0.2848	0.025*
C23	−0.4991 (2)	1.12856 (12)	0.21073 (9)	0.0207 (2)
H23A	−0.5509	1.1623	0.1524	0.025*
C24	−0.2890 (2)	1.05397 (11)	0.21745 (9)	0.0186 (2)
H24A	−0.2017	1.0379	0.1637	0.022*
H1O3	0.016 (4)	0.804 (2)	0.5079 (18)	0.048 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0363 (2)	0.0397 (2)	0.01977 (16)	−0.02068 (16)	0.01019 (13)	−0.00255 (13)
Cl2	0.0479 (2)	0.02154 (17)	0.0407 (2)	−0.00267 (15)	−0.02561 (18)	−0.00634 (14)
O1	0.0146 (4)	0.0231 (4)	0.0190 (4)	0.0003 (3)	−0.0009 (3)	−0.0002 (3)
O2	0.0161 (4)	0.0323 (5)	0.0233 (5)	0.0001 (4)	0.0039 (4)	0.0024 (4)
O3	0.0141 (4)	0.0267 (5)	0.0172 (4)	0.0011 (3)	0.0017 (3)	0.0027 (4)
N1	0.0159 (5)	0.0181 (5)	0.0129 (4)	−0.0009 (4)	−0.0002 (4)	0.0001 (4)
N2	0.0168 (5)	0.0244 (5)	0.0121 (5)	0.0032 (4)	0.0022 (4)	0.0013 (4)
C1	0.0146 (5)	0.0193 (5)	0.0181 (5)	−0.0016 (4)	−0.0010 (4)	−0.0018 (4)
C2	0.0175 (5)	0.0167 (5)	0.0172 (5)	−0.0027 (4)	−0.0019 (4)	−0.0023 (4)
C3	0.0196 (6)	0.0174 (5)	0.0229 (6)	−0.0005 (4)	−0.0054 (5)	−0.0025 (4)
C4	0.0268 (6)	0.0166 (5)	0.0206 (6)	−0.0024 (5)	−0.0073 (5)	0.0002 (4)
C5	0.0267 (6)	0.0199 (6)	0.0178 (6)	−0.0039 (5)	−0.0007 (5)	0.0007 (4)
C6	0.0196 (6)	0.0206 (6)	0.0190 (6)	−0.0022 (5)	0.0004 (4)	0.0011 (4)
C7	0.0169 (5)	0.0166 (5)	0.0168 (5)	−0.0024 (4)	−0.0015 (4)	−0.0008 (4)
C8	0.0144 (5)	0.0168 (5)	0.0172 (5)	−0.0019 (4)	−0.0009 (4)	−0.0016 (4)
C9	0.0132 (5)	0.0175 (5)	0.0153 (5)	−0.0019 (4)	−0.0006 (4)	−0.0021 (4)
C10	0.0140 (5)	0.0170 (5)	0.0147 (5)	−0.0033 (4)	0.0003 (4)	−0.0024 (4)
C11	0.0140 (5)	0.0205 (5)	0.0156 (5)	−0.0035 (4)	0.0008 (4)	−0.0015 (4)
C12	0.0149 (5)	0.0176 (5)	0.0139 (5)	−0.0028 (4)	0.0021 (4)	−0.0011 (4)
C13	0.0135 (5)	0.0155 (5)	0.0157 (5)	−0.0013 (4)	0.0001 (4)	−0.0001 (4)
C14	0.0157 (5)	0.0183 (5)	0.0249 (6)	−0.0031 (4)	0.0022 (5)	0.0005 (5)
C15	0.0178 (6)	0.0176 (6)	0.0392 (8)	−0.0047 (5)	−0.0043 (5)	−0.0005 (5)
C16	0.0274 (7)	0.0161 (5)	0.0281 (7)	−0.0003 (5)	−0.0130 (5)	−0.0035 (5)
C17	0.0325 (7)	0.0220 (6)	0.0167 (6)	−0.0026 (5)	−0.0037 (5)	−0.0017 (5)
C18	0.0207 (6)	0.0201 (6)	0.0162 (5)	−0.0055 (5)	0.0006 (4)	0.0003 (4)
C19	0.0154 (5)	0.0144 (5)	0.0156 (5)	−0.0018 (4)	0.0003 (4)	−0.0015 (4)
C20	0.0188 (6)	0.0183 (5)	0.0148 (5)	−0.0020 (4)	0.0012 (4)	−0.0016 (4)
C21	0.0191 (6)	0.0199 (6)	0.0197 (6)	−0.0011 (5)	0.0041 (4)	−0.0029 (4)
C22	0.0176 (6)	0.0195 (6)	0.0240 (6)	0.0010 (4)	0.0001 (5)	−0.0018 (5)
C23	0.0218 (6)	0.0192 (6)	0.0184 (6)	0.0003 (5)	−0.0024 (5)	0.0007 (4)
C24	0.0202 (6)	0.0178 (5)	0.0157 (5)	−0.0005 (4)	0.0013 (4)	−0.0001 (4)

Cl1—C18	1.7408 (14)	C11—C12	1.5464 (17)
Cl2—C16	1.7402 (14)	C11—H11A	0.9700
O1—C2	1.3720 (16)	C11—H11B	0.9700
O1—C1	1.3770 (15)	C12—C13	1.5175 (17)
O2—C1	1.2097 (16)	C12—H12A	0.9800
O3—C8	1.3294 (15)	C13—C18	1.3929 (17)
O3—H1O3	0.86 (3)	C13—C14	1.3958 (17)
N1—C10	1.3037 (16)	C14—C15	1.385 (2)
N1—N2	1.3726 (14)	C14—H14A	0.9300
N2—C19	1.3857 (15)	C15—C16	1.388 (2)
N2—C12	1.4634 (15)	C15—H15A	0.9300
C1—C9	1.4560 (17)	C16—C17	1.383 (2)
C2—C3	1.3944 (17)	C17—C18	1.3911 (18)
C2—C7	1.3946 (17)	C17—H17A	0.9300
C3—C4	1.386 (2)	C19—C20	1.4019 (17)
C3—H3A	0.9300	C19—C24	1.4033 (17)
C4—C5	1.399 (2)	C20—C21	1.3884 (18)
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.3828 (18)	C21—C22	1.3904 (19)
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.4041 (18)	C22—C23	1.3876 (19)
C6—H6A	0.9300	C22—H22A	0.9300
C7—C8	1.4420 (17)	C23—C24	1.3907 (18)
C8—C9	1.3807 (17)	C23—H23A	0.9300
C9—C10	1.4540 (17)	C24—H24A	0.9300
C10—C11	1.5085 (17)
C2—O1—C1	122.30 (10)	N2—C12—C13	112.71 (10)
C8—O3—H1O3	108.6 (17)	N2—C12—C11	102.00 (9)
C10—N1—N2	109.48 (10)	C13—C12—C11	112.55 (10)
N1—N2—C19	121.38 (10)	N2—C12—H12A	109.8
N1—N2—C12	112.49 (10)	C13—C12—H12A	109.8
C19—N2—C12	126.03 (10)	C11—C12—H12A	109.8
O2—C1—O1	116.12 (11)	C18—C13—C14	117.41 (12)
O2—C1—C9	125.99 (12)	C18—C13—C12	120.73 (11)
O1—C1—C9	117.88 (11)	C14—C13—C12	121.85 (11)
O1—C2—C3	116.69 (11)	C15—C14—C13	121.30 (13)
O1—C2—C7	121.53 (11)	C15—C14—H14A	119.4
C3—C2—C7	121.78 (12)	C13—C14—H14A	119.4
C4—C3—C2	118.17 (12)	C14—C15—C16	119.24 (13)
C4—C3—H3A	120.9	C14—C15—H15A	120.4
C2—C3—H3A	120.9	C16—C15—H15A	120.4
C3—C4—C5	121.11 (12)	C17—C16—C15	121.55 (12)
C3—C4—H4A	119.4	C17—C16—Cl2	118.24 (12)
C5—C4—H4A	119.4	C15—C16—Cl2	120.21 (11)
C6—C5—C4	120.11 (13)	C16—C17—C18	117.73 (13)
C6—C5—H5A	119.9	C16—C17—H17A	121.1
C4—C5—H5A	119.9	C18—C17—H17A	121.1
C5—C6—C7	119.86 (12)	C17—C18—C13	122.74 (12)
C5—C6—H6A	120.1	C17—C18—Cl1	117.93 (10)
C7—C6—H6A	120.1	C13—C18—Cl1	119.33 (10)
C2—C7—C6	118.95 (11)	N2—C19—C20	121.34 (11)
C2—C7—C8	117.75 (11)	N2—C19—C24	119.68 (11)
C6—C7—C8	123.25 (11)	C20—C19—C24	118.98 (11)
O3—C8—C9	122.99 (11)	C21—C20—C19	119.77 (12)
O3—C8—C7	116.36 (11)	C21—C20—H20A	120.1
C9—C8—C7	120.63 (11)	C19—C20—H20A	120.1
C8—C9—C10	121.34 (11)	C20—C21—C22	121.39 (12)
C8—C9—C1	119.77 (11)	C20—C21—H21A	119.3
C10—C9—C1	118.88 (11)	C22—C21—H21A	119.3
N1—C10—C9	119.64 (11)	C23—C22—C21	118.75 (12)
N1—C10—C11	112.43 (10)	C23—C22—H22A	120.6
C9—C10—C11	127.92 (11)	C21—C22—H22A	120.6
C10—C11—C12	102.04 (9)	C22—C23—C24	120.94 (12)
C10—C11—H11A	111.4	C22—C23—H23A	119.5
C12—C11—H11A	111.4	C24—C23—H23A	119.5
C10—C11—H11B	111.4	C23—C24—C19	120.14 (12)
C12—C11—H11B	111.4	C23—C24—H24A	119.9
H11A—C11—H11B	109.2	C19—C24—H24A	119.9
C10—N1—N2—C19	−176.79 (11)	C9—C10—C11—C12	171.31 (12)
C10—N1—N2—C12	6.61 (15)	N1—N2—C12—C13	109.17 (12)
C2—O1—C1—O2	176.03 (12)	C19—N2—C12—C13	−67.25 (16)
C2—O1—C1—C9	−4.01 (17)	N1—N2—C12—C11	−11.76 (13)
C1—O1—C2—C3	−175.51 (11)	C19—N2—C12—C11	171.82 (12)
C1—O1—C2—C7	4.23 (18)	C10—C11—C12—N2	11.62 (12)
O1—C2—C3—C4	178.39 (11)	C10—C11—C12—C13	−109.42 (11)
C7—C2—C3—C4	−1.36 (19)	N2—C12—C13—C18	157.95 (11)
C2—C3—C4—C5	0.6 (2)	C11—C12—C13—C18	−87.35 (14)
C3—C4—C5—C6	0.7 (2)	N2—C12—C13—C14	−23.34 (16)
C4—C5—C6—C7	−1.3 (2)	C11—C12—C13—C14	91.36 (14)
O1—C2—C7—C6	−178.93 (12)	C18—C13—C14—C15	−1.30 (19)
C3—C2—C7—C6	0.81 (19)	C12—C13—C14—C15	179.95 (11)
O1—C2—C7—C8	−1.45 (18)	C13—C14—C15—C16	0.2 (2)
C3—C2—C7—C8	178.28 (11)	C14—C15—C16—C17	1.2 (2)
C5—C6—C7—C2	0.53 (19)	C14—C15—C16—Cl2	−178.28 (10)
C5—C6—C7—C8	−176.79 (12)	C15—C16—C17—C18	−1.3 (2)
C2—C7—C8—O3	−179.67 (11)	Cl2—C16—C17—C18	178.16 (10)
C6—C7—C8—O3	−2.31 (18)	C16—C17—C18—C13	0.1 (2)
C2—C7—C8—C9	−1.31 (18)	C16—C17—C18—Cl1	−179.87 (10)
C6—C7—C8—C9	176.04 (12)	C14—C13—C18—C17	1.17 (19)
O3—C8—C9—C10	0.68 (19)	C12—C13—C18—C17	179.93 (12)
C7—C8—C9—C10	−177.57 (11)	C14—C13—C18—Cl1	−178.87 (9)
O3—C8—C9—C1	179.66 (11)	C12—C13—C18—Cl1	−0.10 (16)
C7—C8—C9—C1	1.41 (18)	N1—N2—C19—C20	8.45 (19)
O2—C1—C9—C8	−178.87 (13)	C12—N2—C19—C20	−175.43 (12)
O1—C1—C9—C8	1.18 (18)	N1—N2—C19—C24	−170.94 (11)
O2—C1—C9—C10	0.1 (2)	C12—N2—C19—C24	5.18 (19)
O1—C1—C9—C10	−179.82 (11)	N2—C19—C20—C21	−177.32 (12)
N2—N1—C10—C9	−178.26 (11)	C24—C19—C20—C21	2.08 (18)
N2—N1—C10—C11	2.11 (14)	C19—C20—C21—C22	−0.9 (2)
C8—C9—C10—N1	3.12 (18)	C20—C21—C22—C23	−0.9 (2)
C1—C9—C10—N1	−175.87 (11)	C21—C22—C23—C24	1.5 (2)
C8—C9—C10—C11	−177.31 (12)	C22—C23—C24—C19	−0.3 (2)
C1—C9—C10—C11	3.70 (19)	N2—C19—C24—C23	177.91 (12)
N1—C10—C11—C12	−9.10 (13)	C20—C19—C24—C23	−1.49 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N1	0.86 (2)	1.80 (3)	2.5655 (14)	148 (2)
C14—H14A···O2i	0.93	2.40	3.2747 (17)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N1	0.86 (2)	1.80 (3)	2.5655 (14)	148 (2)
C14—H14A⋯O2i	0.93	2.40	3.2747 (17)	157

Symmetry code: (i) .