8-Chloro-6-iodo-2-phenyl­chromeno[4,3-c]pyrazol-4(2H)-one N,N-dimethyl­formamide monosolvate

Lokhande, P.; Hasanzadeh, K.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536811022070

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1692

doi:10.1107/S1600536811022070

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8-Chloro-6-iodo-2-phenylchromeno[4,3-c]pyrazol-4(2H)-one N,N-dimethylformamide monosolvate

Pradeep Lokhande,^a Kamal Hasanzadeh,^a Hamid Khaledi ^b ^* and Hapipah Mohd Ali ^b

^aDepartment of Chemistry, University of Pune, Pune 411007, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 20 May 2011; accepted 7 June 2011; online 18 June 2011)

In the title compound, C₁₆H₈ClIN₂O₂·C₃H₇NO, the fused tricyclic pyrazolocoumarin ring and the N-phenyl ring are almost coplanar, the dihedral angle between them being 1.86 (9)°. In the crystal, these rings stack on top of each other via π–π interactions [centroid–centroid distances = 3.489 (2), 3.637 (2), 3.505 (2) and 3.662 (2) Å], forming infinite chains along the a axis. The chains are connected into layers parallel to ac plane through I⋯O interactions [3.0011 (18) Å] between pairs of symmetry-related molecules. The DMF solvent molecules are C—H⋯O bonded to this network.

Related literature

For related structures, see: Strakova et al. (2003 ); Kanwal et al. (2007 ). For a crystal structure (p-iodobenzaldehyde) having I⋯O interactions, see: Britton & Young (1997). For a background to the I2/DMSO reagent, see: Lokhande et al. (2005 ).

Experimental

Crystal data

C₁₆H₈ClIN₂O₂·C₃H₇NO
M_r = 495.69
Triclinic, $[P \overline 1]$
a = 7.7297 (5) Å
b = 11.5196 (2) Å
c = 12.0326 (3) Å
α = 118.484 (1)°
β = 99.841 (1)°
γ = 90.968 (1)°
V = 921.86 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.91 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.598, T_max = 0.963
7205 measured reflections
3392 independent reflections
3075 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.052
S = 1.10
3392 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3	0.95	2.19	3.122 (3)	167
C16—H16⋯O3	0.95	2.49	3.415 (3)	164

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536811022070/go2013sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022070/go2013Isup2.hkl

checkCIF report

Comment top

The title compound was obtained through a cyclization/iodination reaction, using I₂/DMSO reagent (Lokhande et al., 2005). The crystal structure consists of the heterocyclic molecules, solvated by DMF molecules. The pyrazolocoumarin moiety is essentially planar (r.m.s deviation of the tricyclic ring atoms = 0.018 Å) as is in the similar structures (Strakova et al., 2003; Kanwal et al., 2007). The plane of the tricyclic ring is inclined slightly with respect to the N-phenyl ring, making an angle of 1.86 (9)°. The iodine atom and the carbonyl O atom of the symmetry related molecule at -x, -y + 2, -z + 1 are brought close together with I1···O2 distance of 3.0011 (18) Å which is significantly shorter than the sum of the Van der Waals radii of the relevant atoms (3.50 A°). Similar intermolecular interactions have been reported for the structure of p-iodobenzaldehyde (Britton & Young, 1997) with I···O distances of 3.068 (4) and 3.074 (4)Å and suggested to be an interaction between the Lewis base, –CHO, and the Lewis acid, I. The crystal packing consists of layers parallel to the ac plane formed by the I···O and the π-π interactions [Cg1···Cg1ⁱ = 3.489 (2) Å; Cg1···Cg3ⁱⁱ = 3.637 (2) Å; Cg2···Cg4ⁱ = 3.505 (2) Å; Cg4···Cg4ⁱ = 3.662 (2) Å, where Cg1, Cg2, Cg3 and Cg4 are the centroids of the rings N1/N2/C7/C8/C10, O1/C6—C9, C1—C6 and C11—C16, respectively, for i: -x + 1, -y + 2, -z + 2; ii: -x, -y + 2, -z + 2]. The DMF solvent molecules are hydrogen bonded to the layers (Table 1).

Related literature top

For related structures, see: Strakova et al. (2003); Kanwal et al. (2007). For a crystal structure (p-iodobenzaldehyde) having I···O interactions, see: Britton & Young (1997). For a background to the I2/DMSO reagent, see: Lokhande et al. (2005).

Experimental top

A solution of 5-chloro-2-hydroxyacetophenone (2.4 mmol, 0.41 g) and phenylhydrazine (2.4 mmol, 0.62 g) in methanol (40 ml), was refluxed for 2 hr to give 5-chloro-2-hydroxy acetophenone phenylhydrazone as a yellow solid (91%). To a solution of the obtained hydrazone (2 mmol, 0.52 g) in DMF (15 ml), POCl₃ (6 mmol, 0.918 g) was added dropwise at 0 ^oC. After completion of the addition, the mixture was heated at 60–70 ^oC for 2.5–3 hr, then poured onto crushed ice and neutralized with 10% aqueous NaOH solution. The precipitate was filtered, washed with water and recrystallized from ethanol to give 3-(5-chloro-2-hydroxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (85%). To a solution of this solid (1 mmol, 0.298 g) in DMSO (20 ml), iodine (1.2 equivalent, 0.304 g) and 4–5 drops of concentrated H₂SO₄ was added. The mixture was heated at 120 ^oC for 3 hr, then cooled to room temperature and poured into ice-cooled water. The separated solid was filtered and washed with a cold dilute sodium thiosulfate solution and recrystallized from DMF to give the colorless crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular strucrure of the title compound (50% probability ellipsoids). Hydrogen atoms are drawn as spheres of arbitrary radius.

8-Chloro-6-iodo-2-phenylchromeno[4,3-c]pyrazol-4(2H)-one N,N-dimethylformamide monosolvate top

Crystal data top

C₁₆H₈ClIN₂O₂·C₃H₇NO	Z = 2
M_r = 495.69	F(000) = 488
Triclinic, P1	D_x = 1.786 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7297 (5) Å	Cell parameters from 4487 reflections
b = 11.5196 (2) Å	θ = 2.7–30.3°
c = 12.0326 (3) Å	µ = 1.91 mm⁻¹
α = 118.484 (1)°	T = 100 K
β = 99.841 (1)°	Needle, colorless
γ = 90.968 (1)°	0.30 × 0.10 × 0.02 mm
V = 921.86 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	3392 independent reflections
Radiation source: fine-focus sealed tube	3075 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.598, T_max = 0.963	k = −13→13
7205 measured reflections	l = −13→14

Refinement top

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0269P)²] where P = (F_o² + 2F_c²)/3
3392 reflections	(Δ/σ)_max = 0.003
246 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₆H₈ClIN₂O₂·C₃H₇NO	γ = 90.968 (1)°
M_r = 495.69	V = 921.86 (7) Å³
Triclinic, P1	Z = 2
a = 7.7297 (5) Å	Mo Kα radiation
b = 11.5196 (2) Å	µ = 1.91 mm⁻¹
c = 12.0326 (3) Å	T = 100 K
α = 118.484 (1)°	0.30 × 0.10 × 0.02 mm
β = 99.841 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3392 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3075 reflections with I > 2σ(I)
T_min = 0.598, T_max = 0.963	R_int = 0.021
7205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.10	Δρ_max = 0.58 e Å⁻³
3392 reflections	Δρ_min = −0.56 e Å⁻³
246 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
I1	−0.11384 (2)	1.169294 (17)	0.628935 (17)	0.01600 (7)
Cl1	−0.02765 (10)	1.45032 (7)	1.17754 (7)	0.02134 (15)
O1	0.0778 (2)	0.97585 (17)	0.70964 (18)	0.0149 (4)
O2	0.1906 (3)	0.78881 (18)	0.60164 (18)	0.0198 (4)
N1	0.2949 (3)	0.9833 (2)	1.0488 (2)	0.0135 (5)
N2	0.3677 (3)	0.8654 (2)	0.9952 (2)	0.0123 (5)
C1	0.0571 (3)	1.0858 (2)	0.8236 (2)	0.0127 (5)
C2	−0.0335 (3)	1.1827 (3)	0.8102 (3)	0.0147 (6)
C3	−0.0607 (3)	1.2950 (3)	0.9203 (3)	0.0146 (6)
H3	−0.1242	1.3617	0.9128	0.017*
C4	0.0055 (3)	1.3084 (3)	1.0406 (3)	0.0153 (6)
C5	0.0988 (3)	1.2139 (3)	1.0556 (3)	0.0148 (6)
H5	0.1450	1.2260	1.1393	0.018*
C6	0.1240 (3)	1.1004 (3)	0.9457 (3)	0.0130 (5)
C7	0.2193 (3)	0.9941 (3)	0.9470 (3)	0.0127 (5)
C8	0.2419 (3)	0.8862 (3)	0.8304 (3)	0.0142 (5)
C9	0.1744 (3)	0.8750 (3)	0.7064 (3)	0.0144 (6)
C10	0.3400 (3)	0.8053 (3)	0.8657 (3)	0.0142 (5)
H10	0.3796	0.7239	0.8098	0.017*
C11	0.4601 (3)	0.8195 (3)	1.0783 (3)	0.0139 (5)
C12	0.4788 (3)	0.8972 (3)	1.2102 (3)	0.0163 (6)
H12	0.4323	0.9804	1.2456	0.020*
C13	0.5671 (4)	0.8521 (3)	1.2909 (3)	0.0186 (6)
H13	0.5817	0.9050	1.3820	0.022*
C14	0.6333 (3)	0.7306 (3)	1.2387 (3)	0.0190 (6)
H14	0.6921	0.6996	1.2939	0.023*
C15	0.6140 (4)	0.6541 (3)	1.1063 (3)	0.0187 (6)
H15	0.6606	0.5711	1.0709	0.022*
C16	0.5267 (3)	0.6980 (3)	1.0246 (3)	0.0170 (6)
H16	0.5131	0.6456	0.9336	0.020*
O3	0.5295 (3)	0.5613 (2)	0.70310 (19)	0.0253 (5)
N3	0.3732 (3)	0.3775 (2)	0.5253 (2)	0.0204 (5)
C17	0.5161 (4)	0.4454 (3)	0.6173 (3)	0.0228 (7)
H17	0.6171	0.3993	0.6162	0.027*
C18	0.3726 (4)	0.2405 (3)	0.4280 (3)	0.0292 (7)
H18A	0.4855	0.2090	0.4459	0.044*
H18B	0.3559	0.2342	0.3426	0.044*
H18C	0.2759	0.1854	0.4295	0.044*
C19	0.2124 (4)	0.4393 (3)	0.5173 (3)	0.0274 (7)
H19A	0.2335	0.5340	0.5816	0.041*
H19B	0.1176	0.3961	0.5341	0.041*
H19C	0.1779	0.4295	0.4307	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01706 (10)	0.01850 (10)	0.01258 (10)	0.00408 (7)	0.00108 (7)	0.00823 (8)
Cl1	0.0319 (4)	0.0175 (3)	0.0138 (3)	0.0083 (3)	0.0068 (3)	0.0061 (3)
O1	0.0175 (9)	0.0147 (9)	0.0114 (10)	0.0039 (8)	0.0018 (8)	0.0057 (8)
O2	0.0308 (11)	0.0178 (10)	0.0112 (10)	0.0104 (9)	0.0056 (9)	0.0068 (9)
N1	0.0135 (11)	0.0133 (11)	0.0135 (12)	0.0010 (9)	0.0012 (9)	0.0068 (10)
N2	0.0122 (11)	0.0120 (11)	0.0130 (12)	0.0005 (9)	0.0010 (9)	0.0069 (10)
C1	0.0121 (13)	0.0131 (13)	0.0099 (13)	−0.0015 (10)	0.0019 (11)	0.0035 (11)
C2	0.0121 (13)	0.0180 (14)	0.0150 (15)	0.0005 (11)	0.0017 (11)	0.0093 (12)
C3	0.0130 (13)	0.0156 (14)	0.0168 (15)	0.0031 (11)	0.0037 (11)	0.0090 (12)
C4	0.0169 (13)	0.0127 (13)	0.0145 (14)	0.0010 (11)	0.0051 (12)	0.0047 (12)
C5	0.0177 (14)	0.0163 (13)	0.0102 (14)	−0.0004 (11)	0.0014 (11)	0.0070 (12)
C6	0.0103 (12)	0.0152 (13)	0.0149 (14)	0.0006 (10)	0.0029 (11)	0.0084 (12)
C7	0.0131 (12)	0.0139 (13)	0.0119 (14)	−0.0030 (10)	0.0027 (11)	0.0069 (11)
C8	0.0159 (13)	0.0151 (13)	0.0120 (14)	−0.0002 (11)	0.0014 (11)	0.0074 (11)
C9	0.0132 (13)	0.0165 (14)	0.0146 (15)	0.0006 (11)	0.0009 (11)	0.0092 (12)
C10	0.0168 (13)	0.0134 (13)	0.0123 (14)	0.0002 (11)	0.0034 (11)	0.0060 (11)
C11	0.0095 (12)	0.0173 (14)	0.0177 (15)	−0.0024 (10)	−0.0011 (11)	0.0121 (12)
C12	0.0171 (14)	0.0175 (14)	0.0143 (14)	0.0007 (11)	0.0023 (12)	0.0080 (12)
C13	0.0180 (14)	0.0265 (15)	0.0121 (14)	−0.0012 (12)	−0.0003 (12)	0.0112 (13)
C14	0.0144 (13)	0.0268 (16)	0.0221 (16)	−0.0032 (12)	−0.0029 (12)	0.0191 (14)
C15	0.0155 (13)	0.0162 (14)	0.0256 (17)	−0.0015 (11)	−0.0003 (12)	0.0127 (13)
C16	0.0189 (14)	0.0159 (14)	0.0162 (15)	0.0015 (11)	0.0008 (12)	0.0088 (12)
O3	0.0324 (12)	0.0209 (11)	0.0172 (11)	0.0065 (9)	0.0037 (10)	0.0053 (10)
N3	0.0241 (13)	0.0185 (12)	0.0163 (13)	0.0046 (10)	0.0033 (11)	0.0068 (11)
C17	0.0267 (16)	0.0267 (17)	0.0217 (17)	0.0097 (13)	0.0093 (14)	0.0155 (15)
C18	0.0326 (18)	0.0234 (16)	0.0236 (18)	0.0047 (14)	0.0034 (15)	0.0059 (14)
C19	0.0230 (16)	0.0296 (17)	0.0278 (18)	0.0081 (13)	0.0046 (14)	0.0126 (15)

Geometric parameters (Å, º) top

I1—C2	2.092 (3)	C11—C12	1.380 (4)
Cl1—C4	1.744 (3)	C11—C16	1.384 (4)
O1—C9	1.380 (3)	C12—C13	1.395 (4)
O1—C1	1.391 (3)	C12—H12	0.9500
O2—C9	1.206 (3)	C13—C14	1.383 (4)
N1—C7	1.327 (3)	C13—H13	0.9500
N1—N2	1.375 (3)	C14—C15	1.383 (4)
N2—C10	1.344 (3)	C14—H14	0.9500
N2—C11	1.436 (3)	C15—C16	1.392 (4)
C1—C2	1.387 (4)	C15—H15	0.9500
C1—C6	1.398 (4)	C16—H16	0.9500
C2—C3	1.394 (4)	O3—C17	1.227 (3)
C3—C4	1.383 (4)	N3—C17	1.335 (4)
C3—H3	0.9500	N3—C18	1.449 (4)
C4—C5	1.381 (4)	N3—C19	1.454 (4)
C5—C6	1.394 (4)	C17—H17	0.9500
C5—H5	0.9500	C18—H18A	0.9800
C6—C7	1.445 (4)	C18—H18B	0.9800
C7—C8	1.404 (4)	C18—H18C	0.9800
C8—C10	1.383 (4)	C19—H19A	0.9800
C8—C9	1.437 (4)	C19—H19B	0.9800
C10—H10	0.9500	C19—H19C	0.9800

C9—O1—C1	123.4 (2)	C12—C11—N2	119.0 (2)
C7—N1—N2	103.4 (2)	C16—C11—N2	119.5 (2)
C10—N2—N1	113.3 (2)	C11—C12—C13	119.1 (3)
C10—N2—C11	127.5 (2)	C11—C12—H12	120.5
N1—N2—C11	119.2 (2)	C13—C12—H12	120.5
C2—C1—O1	116.1 (2)	C14—C13—C12	120.1 (3)
C2—C1—C6	121.0 (2)	C14—C13—H13	119.9
O1—C1—C6	122.9 (2)	C12—C13—H13	119.9
C1—C2—C3	119.2 (2)	C15—C14—C13	120.0 (3)
C1—C2—I1	121.04 (19)	C15—C14—H14	120.0
C3—C2—I1	119.61 (19)	C13—C14—H14	120.0
C4—C3—C2	119.4 (2)	C14—C15—C16	120.5 (3)
C4—C3—H3	120.3	C14—C15—H15	119.8
C2—C3—H3	120.3	C16—C15—H15	119.8
C5—C4—C3	122.1 (3)	C11—C16—C15	118.8 (3)
C5—C4—Cl1	119.1 (2)	C11—C16—H16	120.6
C3—C4—Cl1	118.8 (2)	C15—C16—H16	120.6
C4—C5—C6	118.8 (3)	C17—N3—C18	121.6 (2)
C4—C5—H5	120.6	C17—N3—C19	121.2 (2)
C6—C5—H5	120.6	C18—N3—C19	117.2 (3)
C5—C6—C1	119.5 (2)	O3—C17—N3	126.3 (3)
C5—C6—C7	124.8 (2)	O3—C17—H17	116.8
C1—C6—C7	115.7 (2)	N3—C17—H17	116.8
N1—C7—C8	112.2 (2)	N3—C18—H18A	109.5
N1—C7—C6	127.8 (2)	N3—C18—H18B	109.5
C8—C7—C6	120.0 (2)	H18A—C18—H18B	109.5
C10—C8—C7	105.3 (2)	N3—C18—H18C	109.5
C10—C8—C9	131.7 (3)	H18A—C18—H18C	109.5
C7—C8—C9	123.0 (2)	H18B—C18—H18C	109.5
O2—C9—O1	117.0 (2)	N3—C19—H19A	109.5
O2—C9—C8	128.1 (2)	N3—C19—H19B	109.5
O1—C9—C8	114.8 (2)	H19A—C19—H19B	109.5
N2—C10—C8	105.8 (2)	N3—C19—H19C	109.5
N2—C10—H10	127.1	H19A—C19—H19C	109.5
C8—C10—H10	127.1	H19B—C19—H19C	109.5
C12—C11—C16	121.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3	0.95	2.19	3.122 (3)	167
C16—H16···O3	0.95	2.49	3.415 (3)	164

Experimental details

Crystal data
Chemical formula	C₁₆H₈ClIN₂O₂·C₃H₇NO
M_r	495.69
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.7297 (5), 11.5196 (2), 12.0326 (3)
α, β, γ (°)	118.484 (1), 99.841 (1), 90.968 (1)
V (Å³)	921.86 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.91
Crystal size (mm)	0.30 × 0.10 × 0.02

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.598, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	7205, 3392, 3075
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.052, 1.10
No. of reflections	3392
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.56

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3	0.95	2.19	3.122 (3)	167
C16—H16···O3	0.95	2.49	3.415 (3)	164

Acknowledgements

The University of Malaya is acknowledged for providing the X-ray facilities.

References

Barbour, L. J. (2001). J. Supramol. Chem, 1, 189–191. CrossRef CAS Google Scholar
Britton, D. & Young, V. G. (1997). Acta Cryst. C53, 1359–1362. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kanwal, P., Gupta, V. K., Brahmbhatt, D. I. & Patel, M. A. (2007). Anal. Sci. X-Ray Struct. Anal. Online, 23, x237–238. CrossRef CAS Google Scholar
Lokhande, P. D., Sakate, S. S., Taksande, K. N. & Navghare, B. (2005). Tetrahedron Lett. 46, 1573–1574. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Strakova, I., Petrova, M., Belyakov, S. & Strakov, A. (2003). Khim. Get. Soedin. pp. 1827–1836. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1692

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

8-Chloro-6-iodo-2-phenyl­chromeno[4,3-c]pyrazol-4(2H)-one N,N-di­methyl­formamide monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

8-Chloro-6-iodo-2-phenylchromeno[4,3-c]pyrazol-4(2H)-one N,N-dimethylformamide monosolvate