(4-Chloro-phen-yl)[1-(4-methoxy-phen-yl)-3-(5-nitro-2-fur-yl)-1H-pyrazol-4-yl]methanone.

In the title compound, C(21)H(14)ClN(3)O(5), an intra-molecular C-H⋯O hydrogen bond generates an S(7) ring motif and the furan and pyrazole rings are almost coplanar, making a dihedral angle of 1.98 (5)°. The pyrazole ring is inclined at dihedral angles of 47.59 (4) and 7.27 (4)° to the chloro-phenyl and methoxy-phenyl groups, respectively. The nitro group is almost coplanar to its attached furan ring [dihedral angle = 2.03 (12)°]. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. The crystal structure also features short inter-molecular O⋯N [2.8546 (12) Å] and Cl⋯O [3.0844 (9) Å] contacts as well as aromatic π-π stacking inter-actions [centroid-centroid distance = 3.4367 (6) Å].

Related literature

For general background to and applications of the title compound, see: Hedge et al. (2006 ▶); Kalluraya et al. (1994 ▶); Rai & Kalluraya (2006 ▶); Rai et al. (2008 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶). For closely related structures, see: Goh et al. (2009 ▶, 2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H14ClN3O5

M = 423.80

Triclinic,

a = 9.5589 (8) Å

b = 9.6603 (8) Å

c = 10.6401 (9) Å

α = 95.523 (2)°

β = 91.074 (2)°

γ = 107.706 (2)°

V = 930.44 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.35 × 0.30 × 0.15 mm

Data collection

Bruker SMART APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.919, T max = 0.963

31674 measured reflections

8076 independent reflections

7107 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.146

S = 1.13

8076 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.70 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/S1600536810011931/hb5382sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011931/hb5382Isup2.hkl

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

C21H14ClN3O5	Z = 2
Mr = 423.80	F(000) = 436
Triclinic, P1	Dx = 1.513 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5589 (8) Å	Cell parameters from 9944 reflections
b = 9.6603 (8) Å	θ = 2.6–37.6°
c = 10.6401 (9) Å	µ = 0.25 mm−1
α = 95.523 (2)°	T = 100 K
β = 91.074 (2)°	Block, orange
γ = 107.706 (2)°	0.35 × 0.30 × 0.15 mm
V = 930.44 (13) Å3

Bruker SMART APEX DUO CCD diffractometer	8076 independent reflections
Radiation source: fine-focus sealed tube	7107 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 35.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.919, Tmax = 0.963	k = −13→15
31674 measured reflections	l = −17→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.095P)2 + 0.1254P] where P = (Fo2 + 2Fc2)/3
8076 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.87 e Å−3
0 restraints	Δρmin = −0.70 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 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	1.29464 (2)	1.14454 (3)	0.06814 (2)	0.02139 (7)
O1	0.61940 (7)	0.32154 (7)	0.56102 (7)	0.01521 (12)
O2	0.71984 (7)	0.69219 (8)	0.30892 (7)	0.01788 (13)
O3	1.40488 (8)	0.71448 (9)	1.04135 (7)	0.02060 (14)
O4	0.30019 (9)	0.02849 (9)	0.52238 (8)	0.02777 (17)
O5	0.47299 (9)	0.09317 (9)	0.67232 (9)	0.02794 (18)
N1	0.99713 (8)	0.64428 (8)	0.64105 (7)	0.01227 (12)
N2	0.87287 (8)	0.52812 (8)	0.62820 (7)	0.01314 (12)
N3	0.41817 (9)	0.10960 (9)	0.57182 (8)	0.01796 (14)
C1	1.11008 (9)	0.82550 (10)	0.28130 (8)	0.01484 (14)
H1A	1.1386	0.7582	0.3241	0.018*
C2	1.21148 (9)	0.92103 (10)	0.21216 (9)	0.01643 (15)
H2A	1.3069	0.9161	0.2064	0.020*
C3	1.16768 (9)	1.02368 (10)	0.15196 (8)	0.01521 (14)
C4	1.02482 (10)	1.03149 (10)	0.15658 (9)	0.01617 (15)
H4A	0.9977	1.1017	0.1167	0.019*
C5	0.92349 (9)	0.93211 (10)	0.22196 (8)	0.01508 (14)
H5A	0.8266	0.9332	0.2228	0.018*
C6	0.96547 (9)	0.83057 (9)	0.28646 (8)	0.01292 (13)
C7	0.84764 (9)	0.72576 (9)	0.35099 (8)	0.01295 (13)
C8	0.88513 (9)	0.66693 (9)	0.46450 (8)	0.01251 (13)
C9	0.80310 (8)	0.54115 (9)	0.52175 (8)	0.01230 (13)
C10	0.66580 (9)	0.42891 (9)	0.48123 (8)	0.01289 (13)
C11	0.56829 (10)	0.40179 (10)	0.37915 (8)	0.01690 (15)
H11A	0.5753	0.4580	0.3119	0.020*
C12	0.45459 (10)	0.27164 (11)	0.39557 (9)	0.01852 (16)
H12A	0.3722	0.2250	0.3421	0.022*
C13	0.49222 (9)	0.23009 (9)	0.50622 (9)	0.01568 (15)
C14	1.00849 (9)	0.72922 (9)	0.54574 (8)	0.01321 (14)
H14A	1.0848	0.8137	0.5363	0.016*
C15	1.09929 (9)	0.66115 (9)	0.74528 (8)	0.01229 (13)
C16	1.07607 (9)	0.55323 (10)	0.82671 (8)	0.01586 (15)
H16A	0.9930	0.4716	0.8143	0.019*
C17	1.17703 (10)	0.56696 (11)	0.92700 (9)	0.01755 (15)
H17A	1.1624	0.4936	0.9805	0.021*
C18	1.29982 (9)	0.69077 (10)	0.94696 (8)	0.01540 (14)
C19	1.32113 (9)	0.80016 (10)	0.86573 (9)	0.01607 (15)
H19A	1.4019	0.8839	0.8800	0.019*
C20	1.22302 (9)	0.78476 (9)	0.76433 (8)	0.01446 (14)
H20A	1.2393	0.8564	0.7091	0.017*
C21	1.39244 (12)	0.60104 (13)	1.12158 (10)	0.0247 (2)
H21A	1.4770	0.6276	1.1793	0.037*
H21B	1.3867	0.5115	1.0709	0.037*
H21C	1.3053	0.5879	1.1684	0.037*

	U11	U22	U33	U12	U13	U23
Cl1	0.01544 (10)	0.02511 (12)	0.01991 (12)	−0.00141 (8)	0.00097 (7)	0.00950 (8)
O1	0.0108 (2)	0.0127 (3)	0.0197 (3)	−0.0006 (2)	0.0000 (2)	0.0044 (2)
O2	0.0113 (2)	0.0195 (3)	0.0219 (3)	0.0026 (2)	−0.0025 (2)	0.0051 (2)
O3	0.0142 (3)	0.0274 (4)	0.0167 (3)	0.0004 (3)	−0.0036 (2)	0.0065 (3)
O4	0.0233 (3)	0.0221 (3)	0.0248 (4)	−0.0114 (3)	0.0003 (3)	−0.0004 (3)
O5	0.0186 (3)	0.0246 (4)	0.0393 (5)	0.0009 (3)	−0.0044 (3)	0.0172 (3)
N1	0.0098 (3)	0.0114 (3)	0.0141 (3)	0.0005 (2)	−0.0005 (2)	0.0027 (2)
N2	0.0099 (3)	0.0119 (3)	0.0157 (3)	0.0003 (2)	−0.0003 (2)	0.0025 (2)
N3	0.0147 (3)	0.0128 (3)	0.0234 (4)	−0.0004 (2)	0.0030 (3)	0.0023 (3)
C1	0.0117 (3)	0.0165 (3)	0.0162 (3)	0.0037 (3)	−0.0007 (2)	0.0037 (3)
C2	0.0111 (3)	0.0196 (4)	0.0177 (4)	0.0027 (3)	−0.0002 (3)	0.0045 (3)
C3	0.0131 (3)	0.0165 (3)	0.0140 (3)	0.0010 (3)	0.0003 (2)	0.0034 (3)
C4	0.0156 (3)	0.0177 (4)	0.0161 (3)	0.0053 (3)	0.0015 (3)	0.0055 (3)
C5	0.0134 (3)	0.0173 (3)	0.0159 (3)	0.0057 (3)	0.0018 (2)	0.0049 (3)
C6	0.0114 (3)	0.0133 (3)	0.0137 (3)	0.0027 (2)	0.0002 (2)	0.0028 (2)
C7	0.0109 (3)	0.0130 (3)	0.0146 (3)	0.0028 (2)	−0.0001 (2)	0.0026 (2)
C8	0.0102 (3)	0.0123 (3)	0.0140 (3)	0.0017 (2)	−0.0001 (2)	0.0025 (2)
C9	0.0098 (3)	0.0115 (3)	0.0150 (3)	0.0021 (2)	0.0008 (2)	0.0020 (2)
C10	0.0100 (3)	0.0121 (3)	0.0150 (3)	0.0010 (2)	0.0014 (2)	0.0016 (2)
C11	0.0153 (3)	0.0168 (4)	0.0143 (3)	−0.0012 (3)	−0.0006 (3)	0.0011 (3)
C12	0.0159 (3)	0.0183 (4)	0.0154 (4)	−0.0027 (3)	−0.0003 (3)	−0.0009 (3)
C13	0.0123 (3)	0.0127 (3)	0.0185 (4)	−0.0012 (3)	0.0018 (3)	0.0008 (3)
C14	0.0112 (3)	0.0125 (3)	0.0146 (3)	0.0011 (2)	−0.0002 (2)	0.0030 (2)
C15	0.0101 (3)	0.0124 (3)	0.0134 (3)	0.0019 (2)	0.0001 (2)	0.0017 (2)
C16	0.0140 (3)	0.0154 (3)	0.0151 (3)	−0.0008 (3)	−0.0009 (3)	0.0042 (3)
C17	0.0152 (3)	0.0198 (4)	0.0153 (4)	0.0008 (3)	−0.0007 (3)	0.0061 (3)
C18	0.0117 (3)	0.0197 (4)	0.0133 (3)	0.0027 (3)	−0.0002 (2)	0.0021 (3)
C19	0.0116 (3)	0.0159 (3)	0.0186 (4)	0.0011 (3)	−0.0013 (3)	0.0021 (3)
C20	0.0112 (3)	0.0130 (3)	0.0180 (4)	0.0016 (2)	−0.0011 (2)	0.0031 (3)
C21	0.0208 (4)	0.0327 (5)	0.0192 (4)	0.0042 (4)	−0.0033 (3)	0.0096 (4)

Cl1—C3	1.7351 (9)	C7—C8	1.4662 (12)
O1—C13	1.3488 (11)	C8—C14	1.3892 (11)
O1—C10	1.3774 (10)	C8—C9	1.4294 (11)
O2—C7	1.2282 (10)	C9—C10	1.4516 (11)
O3—C18	1.3593 (11)	C10—C11	1.3696 (12)
O3—C21	1.4313 (13)	C11—C12	1.4180 (13)
O4—N3	1.2343 (11)	C11—H11A	0.9300
O5—N3	1.2270 (12)	C12—C13	1.3563 (13)
N1—C14	1.3503 (11)	C12—H12A	0.9300
N1—N2	1.3574 (10)	C14—H14A	0.9300
N1—C15	1.4275 (11)	C15—C16	1.3883 (12)
N2—C9	1.3393 (11)	C15—C20	1.3969 (12)
N3—C13	1.4200 (12)	C16—C17	1.3942 (12)
C1—C2	1.3949 (12)	C16—H16A	0.9300
C1—C6	1.3998 (12)	C17—C18	1.3933 (13)
C1—H1A	0.9300	C17—H17A	0.9300
C2—C3	1.3906 (12)	C18—C19	1.3987 (13)
C2—H2A	0.9300	C19—C20	1.3828 (12)
C3—C4	1.3919 (12)	C19—H19A	0.9300
C4—C5	1.3899 (13)	C20—H20A	0.9300
C4—H4A	0.9300	C21—H21A	0.9600
C5—C6	1.3975 (12)	C21—H21B	0.9600
C5—H5A	0.9300	C21—H21C	0.9600
C6—C7	1.4948 (12)
C13—O1—C10	105.18 (7)	O1—C10—C9	114.95 (7)
C18—O3—C21	117.66 (8)	C10—C11—C12	106.87 (8)
C14—N1—N2	112.41 (7)	C10—C11—H11A	126.6
C14—N1—C15	128.09 (7)	C12—C11—H11A	126.6
N2—N1—C15	119.46 (7)	C13—C12—C11	104.95 (8)
C9—N2—N1	105.18 (7)	C13—C12—H12A	127.5
O5—N3—O4	124.52 (9)	C11—C12—H12A	127.5
O5—N3—C13	119.17 (8)	O1—C13—C12	112.92 (8)
O4—N3—C13	116.31 (9)	O1—C13—N3	116.80 (8)
C2—C1—C6	120.23 (8)	C12—C13—N3	130.27 (8)
C2—C1—H1A	119.9	N1—C14—C8	107.30 (7)
C6—C1—H1A	119.9	N1—C14—H14A	126.3
C3—C2—C1	118.94 (8)	C8—C14—H14A	126.3
C3—C2—H2A	120.5	C16—C15—C20	120.14 (8)
C1—C2—H2A	120.5	C16—C15—N1	119.68 (7)
C2—C3—C4	121.82 (8)	C20—C15—N1	120.17 (7)
C2—C3—Cl1	118.96 (7)	C15—C16—C17	120.14 (8)
C4—C3—Cl1	119.22 (7)	C15—C16—H16A	119.9
C5—C4—C3	118.60 (8)	C17—C16—H16A	119.9
C5—C4—H4A	120.7	C18—C17—C16	119.84 (8)
C3—C4—H4A	120.7	C18—C17—H17A	120.1
C4—C5—C6	120.81 (8)	C16—C17—H17A	120.1
C4—C5—H5A	119.6	O3—C18—C17	124.49 (8)
C6—C5—H5A	119.6	O3—C18—C19	115.85 (8)
C5—C6—C1	119.53 (8)	C17—C18—C19	119.66 (8)
C5—C6—C7	116.77 (7)	C20—C19—C18	120.48 (8)
C1—C6—C7	123.58 (7)	C20—C19—H19A	119.8
O2—C7—C8	120.95 (8)	C18—C19—H19A	119.8
O2—C7—C6	119.13 (8)	C19—C20—C15	119.70 (8)
C8—C7—C6	119.91 (7)	C19—C20—H20A	120.1
C14—C8—C9	104.13 (7)	C15—C20—H20A	120.1
C14—C8—C7	126.36 (8)	O3—C21—H21A	109.5
C9—C8—C7	129.40 (7)	O3—C21—H21B	109.5
N2—C9—C8	110.98 (7)	H21A—C21—H21B	109.5
N2—C9—C10	117.95 (7)	O3—C21—H21C	109.5
C8—C9—C10	131.03 (8)	H21A—C21—H21C	109.5
C11—C10—O1	110.07 (7)	H21B—C21—H21C	109.5
C11—C10—C9	134.98 (8)
C14—N1—N2—C9	−0.53 (9)	O1—C10—C11—C12	0.31 (10)
C15—N1—N2—C9	−178.56 (7)	C9—C10—C11—C12	179.62 (9)
C6—C1—C2—C3	1.91 (13)	C10—C11—C12—C13	−0.05 (10)
C1—C2—C3—C4	−1.44 (14)	C10—O1—C13—C12	0.43 (10)
C1—C2—C3—Cl1	178.93 (7)	C10—O1—C13—N3	−178.49 (7)
C2—C3—C4—C5	−0.89 (14)	C11—C12—C13—O1	−0.24 (11)
Cl1—C3—C4—C5	178.74 (7)	C11—C12—C13—N3	178.50 (9)
C3—C4—C5—C6	2.78 (14)	O5—N3—C13—O1	−1.02 (13)
C4—C5—C6—C1	−2.31 (13)	O4—N3—C13—O1	178.36 (8)
C4—C5—C6—C7	−178.41 (8)	O5—N3—C13—C12	−179.72 (10)
C2—C1—C6—C5	−0.08 (13)	O4—N3—C13—C12	−0.34 (15)
C2—C1—C6—C7	175.74 (8)	N2—N1—C14—C8	0.08 (9)
C5—C6—C7—O2	27.96 (12)	C15—N1—C14—C8	177.90 (7)
C1—C6—C7—O2	−147.96 (9)	C9—C8—C14—N1	0.37 (9)
C5—C6—C7—C8	−150.78 (8)	C7—C8—C14—N1	177.02 (8)
C1—C6—C7—C8	33.30 (12)	C14—N1—C15—C16	−172.85 (8)
O2—C7—C8—C14	−156.41 (9)	N2—N1—C15—C16	4.84 (12)
C6—C7—C8—C14	22.30 (12)	C14—N1—C15—C20	6.33 (13)
O2—C7—C8—C9	19.38 (14)	N2—N1—C15—C20	−175.98 (7)
C6—C7—C8—C9	−161.90 (8)	C20—C15—C16—C17	−0.74 (13)
N1—N2—C9—C8	0.76 (9)	N1—C15—C16—C17	178.45 (8)
N1—N2—C9—C10	178.64 (7)	C15—C16—C17—C18	1.34 (14)
C14—C8—C9—N2	−0.72 (9)	C21—O3—C18—C17	3.45 (14)
C7—C8—C9—N2	−177.23 (8)	C21—O3—C18—C19	−176.00 (9)
C14—C8—C9—C10	−178.24 (8)	C16—C17—C18—O3	−179.70 (8)
C7—C8—C9—C10	5.26 (15)	C16—C17—C18—C19	−0.27 (14)
C13—O1—C10—C11	−0.45 (9)	O3—C18—C19—C20	178.05 (8)
C13—O1—C10—C9	−179.91 (7)	C17—C18—C19—C20	−1.43 (13)
N2—C9—C10—C11	−177.28 (9)	C18—C19—C20—C15	2.03 (13)
C8—C9—C10—C11	0.10 (16)	C16—C15—C20—C19	−0.95 (13)
N2—C9—C10—O1	2.01 (11)	N1—C15—C20—C19	179.87 (8)
C8—C9—C10—O1	179.38 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.93	2.27	2.9153 (12)	126
C2—H2A···O5i	0.93	2.48	3.2820 (13)	145
C14—H14A···O4ii	0.93	2.46	3.3846 (12)	175
C21—H21A···O2iii	0.96	2.55	3.5064 (14)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2	0.93	2.27	2.9153 (12)	126
C2—H2A⋯O5i	0.93	2.48	3.2820 (13)	145
C14—H14A⋯O4ii	0.93	2.46	3.3846 (12)	175
C21—H21A⋯O2iii	0.96	2.55	3.5064 (14)	173

Symmetry codes: (i) ; (ii) ; (iii) .