N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide–naphthalene-2,3-diol (1/1)

Asiri, A.M.; Khan, S.A.; Tan, K.W.; Ng, S.W.

doi:10.1107/S1600536810024438

organic compounds

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Volume 66| Part 7| July 2010| Page o1850

doi:10.1107/S1600536810024438

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N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide–naphthalene-2,3-diol (1/1)

Abdullah M. Asiri,^a Salman A. Khan,^a Kong Wai Tan ^b and Seik Weng Ng ^b ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 16 June 2010; accepted 23 June 2010; online 26 June 2010)

In the reaction of naphthalene-2,3-diol and 4-aminoantipyrine in the presence of acetic acid, the amine function is acetylated and the resulting acetamide co-crystallizes with the diol in the title compound, C₁₃H₁₅N₃O₂·C₁₀H₈O₂, with 1:1 molar stoichiometry. The two components are linked by two O–H⋯O=C hydrogen bonds. One of the hydroxy groups interacts with the pyrazolone carbonyl O atom and the other hydroxy group interacts with the amide O atom of another component, generating a chain motif. Adjacent chains are linked into a layer motif via N—H⋯O interactions involving only the heterocyclic acetamide component.

Related literature

For the crystal structure of 4-acetamido-2,3-dimethyl-1-phenyl-5-pyrazol-3-one, see: Kuznetsov et al. (1999 ). For co-crystals of naphthalene-2,3-diol, see: Fritchie & Johnston (1975 ); Herbert & Truter (1980 ); Kuo et al. (1974 ); Nakamatsu et al. (2003 ); Wang et al. (2008 ); Wells et al. (1974 ).

Experimental

Crystal data

C₁₃H₁₅N₃O₂·C₁₀H₈O₂
M_r = 405.44
Monoclinic, P 2₁ /c
a = 12.426 (1) Å
b = 14.304 (2) Å
c = 12.959 (1) Å
β = 117.845 (1)°
V = 2036.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
19263 measured reflections
4683 independent reflections
3189 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.131
S = 1.02
4683 reflections
286 parameters
27 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.87 (1)	2.07 (1)	2.924 (2)	169 (2)
O3—H3⋯O2	0.85 (3)	1.81 (3)	2.639 (2)	163 (3)
O4—H4⋯O1ⁱⁱ	0.85 (3)	1.81 (3)	2.646 (2)	168 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024438/im2213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024438/im2213Isup2.hkl

checkCIF report

Comment top

Naphthalene-2,3-diol forms co-crystals with a number of neutral organic compounds (Fritchie & Johnston, 1975; Herbert & Truter, 1980; Kuo et al., 1974; Nakamatsu et al., 2003; Wang et al., 2008; Wells et al., 1974). The attempt to co-crystallize it with the drug 4-aminoantipyrine was sussessful when the reaction was carried out in the presence of acetic acid, but the acetic acid converted the amino group to an acetamido group instead. In the co-crystal (Scheme I, Fig. 1), the acetamide and the diol are linked by two O–H···O═C hydrogen bonds. One of the hydroxy groups interacts with the pyrazolyl carbonyl O-atom and the other hydroxy group interacts with the amido O-atom of another component to generate a chain motif. Adjacent chains are linked into a layer motif via N–H···O interactions that involves the acetamide component only.

Related literature top

For the crystal structure of 4-acetamido-2,3-dimethyl-1-phenyl-5-pyrazol-3-one, see: Kuznetsov et al. (1999). For co-crystals of naphthalene-2,3-diol, see: Fritchie & Johnston (1975); Herbert & Truter (1980); Kuo et al. (1974); Nakamatsu et al. (2003); Wang et al. (2008); Wells et al. (1974).

Experimental top

Naphthalene-2,3-diol (0.35 g, 2.2 mol) and 4-aminoantipyrine (0.45 g, 2.2 mmol) were heated in methanol (15 ml) for 5 h; three drops of acetic acid were added. Crystals separated from the cool solution when it was set aside for a day.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the (C₁₃H₁₅N₃O₂)(C₁₀H₈O₂) co-crystal at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4- yl)acetamide–naphthalene-2,3-diol (1/1) top

Crystal data top

C₁₃H₁₅N₃O₂·C₁₀H₈O₂	F(000) = 856
M_r = 405.44	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2505 reflections
a = 12.426 (1) Å	θ = 2.3–27.9°
b = 14.304 (2) Å	µ = 0.09 mm⁻¹
c = 12.959 (1) Å	T = 100 K
β = 117.845 (1)°	Prism, colorless
V = 2036.7 (4) Å³	0.25 × 0.25 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.061
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −16→16
19263 measured reflections	k = −18→18
4683 independent reflections	l = −16→16

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0544P)² + 0.6929P] where P = (F_o² + 2F_c²)/3
4683 reflections	(Δ/σ)_max = 0.001
286 parameters	Δρ_max = 0.31 e Å⁻³
27 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₃H₁₅N₃O₂·C₁₀H₈O₂	V = 2036.7 (4) Å³
M_r = 405.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.426 (1) Å	µ = 0.09 mm⁻¹
b = 14.304 (2) Å	T = 100 K
c = 12.959 (1) Å	0.25 × 0.25 × 0.10 mm
β = 117.845 (1)°

Data collection top

Bruker SMART APEX diffractometer	3189 reflections with I > 2σ(I)
19263 measured reflections	R_int = 0.061
4683 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	27 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.31 e Å⁻³
4683 reflections	Δρ_min = −0.36 e Å⁻³
286 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.33173 (12)	0.73209 (10)	0.32885 (12)	0.0290 (3)
O2	0.65387 (11)	0.56345 (9)	0.48381 (11)	0.0232 (3)
O3	0.56600 (12)	0.65279 (10)	0.60626 (11)	0.0253 (3)
O4	0.44923 (12)	0.70985 (10)	0.71521 (12)	0.0279 (3)
N1	0.37471 (14)	0.57790 (11)	0.36783 (14)	0.0224 (4)
N2	0.51486 (14)	0.55398 (11)	0.18066 (13)	0.0233 (4)
N3	0.61709 (14)	0.55929 (11)	0.29124 (13)	0.0219 (4)
C1	0.25557 (17)	0.65611 (14)	0.44515 (17)	0.0255 (4)
H1A	0.1879	0.7007	0.4123	0.038*
H1B	0.3105	0.6728	0.5264	0.038*
H1C	0.2237	0.5929	0.4422	0.038*
C2	0.32386 (16)	0.65897 (14)	0.37571 (16)	0.0219 (4)
C3	0.58105 (17)	0.56524 (12)	0.37598 (16)	0.0199 (4)
C4	0.45083 (17)	0.57041 (13)	0.31423 (16)	0.0218 (4)
C5	0.41487 (17)	0.56533 (13)	0.19785 (16)	0.0240 (4)
C6	0.29135 (19)	0.57192 (16)	0.09672 (18)	0.0326 (5)
H6A	0.2302	0.5591	0.1226	0.049*
H6B	0.2835	0.5261	0.0374	0.049*
H6C	0.2788	0.6350	0.0634	0.049*
C7	0.52538 (19)	0.60264 (14)	0.08616 (17)	0.0284 (5)
H7A	0.4540	0.5885	0.0116	0.043*
H7B	0.5992	0.5817	0.0836	0.043*
H7C	0.5300	0.6702	0.1002	0.043*
C8	0.73390 (18)	0.53349 (14)	0.30516 (17)	0.0266 (4)
C9	0.7468 (2)	0.45251 (15)	0.25275 (18)	0.0326 (5)
H9	0.6785	0.4135	0.2091	0.039*
C10	0.8600 (2)	0.4293 (2)	0.2648 (2)	0.0501 (7)
H10	0.8696	0.3745	0.2285	0.060*
C11	0.9594 (2)	0.4857 (2)	0.3296 (3)	0.0681 (10)
H11	1.0371	0.4698	0.3375	0.082*
C12	0.9456 (2)	0.5654 (2)	0.3830 (3)	0.0676 (10)
H12	1.0144	0.6035	0.4284	0.081*
C13	0.8323 (2)	0.59026 (18)	0.3707 (2)	0.0428 (6)
H13	0.8226	0.6452	0.4067	0.051*
C14	0.63471 (17)	0.66192 (13)	0.72372 (15)	0.0202 (4)
C15	0.75639 (18)	0.64515 (14)	0.78429 (17)	0.0266 (4)
H15	0.7987	0.6232	0.7440	0.032*
C16	0.82114 (19)	0.65991 (16)	0.90656 (18)	0.0339 (5)
C17	0.9490 (2)	0.6515 (2)	0.9714 (2)	0.0634 (9)
H17	0.9945	0.6316	0.9335	0.076*
C18	1.0082 (3)	0.6715 (3)	1.0883 (2)	0.0872 (13)
H18	1.0944	0.6674	1.1299	0.105*
C19	0.9427 (2)	0.6980 (3)	1.1467 (2)	0.0719 (10)
H19	0.9845	0.7104	1.2281	0.086*
C20	0.8197 (2)	0.70618 (18)	1.08762 (19)	0.0406 (6)
H20	0.7761	0.7235	1.1285	0.049*
C21	0.75571 (18)	0.68925 (14)	0.96659 (17)	0.0274 (4)
C22	0.62919 (17)	0.70463 (13)	0.90182 (16)	0.0211 (4)
H22	0.5848	0.7235	0.9413	0.025*
C23	0.56923 (16)	0.69285 (12)	0.78342 (16)	0.0198 (4)
H1	0.373 (2)	0.5318 (11)	0.4107 (17)	0.036 (6)*
H3	0.608 (2)	0.6281 (17)	0.577 (2)	0.054 (8)*
H4	0.419 (2)	0.7345 (19)	0.755 (2)	0.067 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0304 (8)	0.0313 (8)	0.0338 (8)	0.0020 (6)	0.0222 (7)	0.0056 (6)
O2	0.0239 (7)	0.0308 (7)	0.0178 (7)	−0.0018 (6)	0.0121 (6)	−0.0039 (5)
O3	0.0269 (7)	0.0340 (8)	0.0172 (7)	0.0026 (6)	0.0121 (6)	−0.0035 (6)
O4	0.0215 (7)	0.0423 (9)	0.0207 (7)	0.0040 (6)	0.0106 (6)	−0.0036 (6)
N1	0.0230 (8)	0.0287 (9)	0.0210 (9)	−0.0039 (7)	0.0147 (7)	0.0004 (7)
N2	0.0266 (9)	0.0303 (9)	0.0165 (8)	−0.0067 (7)	0.0131 (7)	−0.0030 (7)
N3	0.0238 (8)	0.0281 (9)	0.0175 (8)	−0.0064 (7)	0.0127 (7)	−0.0067 (7)
C1	0.0186 (9)	0.0374 (11)	0.0224 (10)	0.0005 (8)	0.0111 (8)	0.0010 (8)
C2	0.0169 (9)	0.0310 (10)	0.0170 (9)	−0.0037 (8)	0.0073 (8)	−0.0025 (8)
C3	0.0263 (10)	0.0194 (9)	0.0196 (10)	−0.0040 (7)	0.0155 (8)	−0.0036 (7)
C4	0.0246 (10)	0.0240 (10)	0.0214 (10)	−0.0042 (8)	0.0147 (8)	−0.0025 (8)
C5	0.0273 (10)	0.0275 (10)	0.0203 (10)	−0.0063 (8)	0.0137 (8)	−0.0024 (8)
C6	0.0285 (11)	0.0463 (13)	0.0221 (11)	−0.0047 (10)	0.0110 (9)	−0.0027 (9)
C7	0.0387 (12)	0.0323 (11)	0.0211 (10)	−0.0084 (9)	0.0198 (10)	−0.0035 (8)
C8	0.0275 (10)	0.0352 (11)	0.0251 (11)	−0.0061 (8)	0.0191 (9)	−0.0079 (8)
C9	0.0346 (12)	0.0400 (12)	0.0291 (12)	−0.0036 (10)	0.0198 (10)	−0.0093 (9)
C10	0.0452 (15)	0.0678 (18)	0.0458 (15)	0.0041 (13)	0.0284 (13)	−0.0223 (13)
C11	0.0308 (14)	0.117 (3)	0.0654 (19)	−0.0044 (15)	0.0300 (14)	−0.0417 (18)
C12	0.0341 (14)	0.110 (3)	0.071 (2)	−0.0277 (15)	0.0349 (14)	−0.0542 (19)
C13	0.0349 (13)	0.0565 (15)	0.0477 (15)	−0.0169 (11)	0.0282 (12)	−0.0290 (12)
C14	0.0257 (10)	0.0207 (9)	0.0159 (9)	−0.0005 (8)	0.0111 (8)	−0.0022 (7)
C15	0.0262 (10)	0.0348 (11)	0.0247 (11)	0.0040 (8)	0.0169 (9)	−0.0030 (8)
C16	0.0252 (11)	0.0538 (14)	0.0230 (11)	0.0065 (10)	0.0115 (9)	−0.0049 (10)
C17	0.0274 (13)	0.125 (3)	0.0358 (14)	0.0178 (14)	0.0129 (11)	−0.0205 (15)
C18	0.0297 (15)	0.180 (4)	0.0390 (16)	0.0292 (19)	0.0051 (13)	−0.025 (2)
C19	0.0341 (14)	0.142 (3)	0.0275 (14)	0.0191 (16)	0.0041 (11)	−0.0231 (16)
C20	0.0315 (12)	0.0672 (17)	0.0221 (11)	0.0076 (11)	0.0117 (10)	−0.0076 (11)
C21	0.0251 (10)	0.0361 (11)	0.0215 (10)	0.0012 (9)	0.0115 (9)	−0.0030 (8)
C22	0.0259 (10)	0.0235 (9)	0.0186 (9)	−0.0005 (8)	0.0145 (8)	−0.0003 (7)
C23	0.0201 (9)	0.0205 (9)	0.0197 (10)	0.0000 (7)	0.0101 (8)	−0.0004 (7)

Geometric parameters (Å, º) top

O1—C2	1.236 (2)	C8—C9	1.389 (3)
O2—C3	1.261 (2)	C9—C10	1.381 (3)
O3—C14	1.360 (2)	C9—H9	0.9500
O3—H3	0.85 (3)	C10—C11	1.383 (4)
O4—C23	1.354 (2)	C10—H10	0.9500
O4—H4	0.85 (3)	C11—C12	1.385 (4)
N1—C2	1.347 (2)	C11—H11	0.9500
N1—C4	1.415 (2)	C12—C13	1.388 (3)
N1—H1	0.868 (10)	C12—H12	0.9500
N2—C5	1.371 (2)	C13—H13	0.9500
N2—N3	1.404 (2)	C14—C15	1.361 (3)
N2—C7	1.466 (2)	C14—C23	1.430 (2)
N3—C3	1.369 (2)	C15—C16	1.418 (3)
N3—C8	1.425 (2)	C15—H15	0.9500
C1—C2	1.498 (2)	C16—C17	1.413 (3)
C1—H1A	0.9800	C16—C21	1.426 (3)
C1—H1B	0.9800	C17—C18	1.369 (4)
C1—H1C	0.9800	C17—H17	0.9500
C3—C4	1.433 (3)	C18—C19	1.398 (4)
C4—C5	1.360 (3)	C18—H18	0.9500
C5—C6	1.484 (3)	C19—C20	1.358 (3)
C6—H6A	0.9800	C19—H19	0.9500
C6—H6B	0.9800	C20—C21	1.409 (3)
C6—H6C	0.9800	C20—H20	0.9500
C7—H7A	0.9800	C21—C22	1.411 (3)
C7—H7B	0.9800	C22—C23	1.367 (3)
C7—H7C	0.9800	C22—H22	0.9500
C8—C13	1.380 (3)

C14—O3—H3	109.9 (18)	C10—C9—H9	120.4
C23—O4—H4	110.2 (19)	C8—C9—H9	120.4
C2—N1—C4	123.16 (16)	C9—C10—C11	120.1 (2)
C2—N1—H1	117.1 (15)	C9—C10—H10	119.9
C4—N1—H1	118.4 (15)	C11—C10—H10	119.9
C5—N2—N3	106.52 (14)	C10—C11—C12	120.0 (2)
C5—N2—C7	121.38 (17)	C10—C11—H11	120.0
N3—N2—C7	115.82 (15)	C12—C11—H11	120.0
C3—N3—N2	110.07 (14)	C11—C12—C13	120.6 (2)
C3—N3—C8	127.60 (16)	C11—C12—H12	119.7
N2—N3—C8	119.84 (14)	C13—C12—H12	119.7
C2—C1—H1A	109.5	C8—C13—C12	118.7 (2)
C2—C1—H1B	109.5	C8—C13—H13	120.7
H1A—C1—H1B	109.5	C12—C13—H13	120.7
C2—C1—H1C	109.5	O3—C14—C15	125.21 (16)
H1A—C1—H1C	109.5	O3—C14—C23	114.64 (16)
H1B—C1—H1C	109.5	C15—C14—C23	120.15 (17)
O1—C2—N1	122.93 (17)	C14—C15—C16	121.07 (17)
O1—C2—C1	121.01 (17)	C14—C15—H15	119.5
N1—C2—C1	116.05 (17)	C16—C15—H15	119.5
O2—C3—N3	123.60 (17)	C17—C16—C15	123.06 (19)
O2—C3—C4	131.17 (16)	C17—C16—C21	117.99 (19)
N3—C3—C4	105.21 (15)	C15—C16—C21	118.87 (18)
C5—C4—N1	126.85 (17)	C18—C17—C16	121.0 (2)
C5—C4—C3	108.47 (16)	C18—C17—H17	119.5
N1—C4—C3	124.68 (16)	C16—C17—H17	119.5
C4—C5—N2	109.47 (17)	C17—C18—C19	120.5 (2)
C4—C5—C6	130.11 (18)	C17—C18—H18	119.8
N2—C5—C6	120.40 (17)	C19—C18—H18	119.8
C5—C6—H6A	109.5	C20—C19—C18	120.3 (2)
C5—C6—H6B	109.5	C20—C19—H19	119.8
H6A—C6—H6B	109.5	C18—C19—H19	119.8
C5—C6—H6C	109.5	C19—C20—C21	120.9 (2)
H6A—C6—H6C	109.5	C19—C20—H20	119.5
H6B—C6—H6C	109.5	C21—C20—H20	119.5
N2—C7—H7A	109.5	C20—C21—C22	121.83 (18)
N2—C7—H7B	109.5	C20—C21—C16	119.28 (19)
H7A—C7—H7B	109.5	C22—C21—C16	118.82 (18)
N2—C7—H7C	109.5	C23—C22—C21	121.33 (17)
H7A—C7—H7C	109.5	C23—C22—H22	119.3
H7B—C7—H7C	109.5	C21—C22—H22	119.3
C13—C8—C9	121.35 (19)	O4—C23—C22	124.57 (16)
C13—C8—N3	118.83 (18)	O4—C23—C14	115.71 (16)
C9—C8—N3	119.81 (18)	C22—C23—C14	119.71 (17)
C10—C9—C8	119.3 (2)

C5—N2—N3—C3	5.4 (2)	C8—C9—C10—C11	0.8 (4)
C7—N2—N3—C3	143.68 (16)	C9—C10—C11—C12	0.3 (5)
C5—N2—N3—C8	168.77 (16)	C10—C11—C12—C13	−1.0 (5)
C7—N2—N3—C8	−52.9 (2)	C9—C8—C13—C12	0.5 (4)
C4—N1—C2—O1	5.8 (3)	N3—C8—C13—C12	−179.3 (2)
C4—N1—C2—C1	−174.38 (16)	C11—C12—C13—C8	0.6 (5)
N2—N3—C3—O2	174.23 (16)	O3—C14—C15—C16	177.70 (19)
C8—N3—C3—O2	12.4 (3)	C23—C14—C15—C16	−1.5 (3)
N2—N3—C3—C4	−4.09 (19)	C14—C15—C16—C17	−174.2 (2)
C8—N3—C3—C4	−165.87 (17)	C14—C15—C16—C21	2.5 (3)
C2—N1—C4—C5	−79.6 (3)	C15—C16—C17—C18	176.3 (3)
C2—N1—C4—C3	101.6 (2)	C21—C16—C17—C18	−0.4 (5)
O2—C3—C4—C5	−176.82 (19)	C16—C17—C18—C19	2.0 (6)
N3—C3—C4—C5	1.3 (2)	C17—C18—C19—C20	−1.5 (6)
O2—C3—C4—N1	2.2 (3)	C18—C19—C20—C21	−0.7 (5)
N3—C3—C4—N1	−179.66 (17)	C19—C20—C21—C22	−174.8 (3)
N1—C4—C5—N2	−176.99 (17)	C19—C20—C21—C16	2.3 (4)
C3—C4—C5—N2	2.0 (2)	C17—C16—C21—C20	−1.7 (3)
N1—C4—C5—C6	4.2 (3)	C15—C16—C21—C20	−178.5 (2)
C3—C4—C5—C6	−176.78 (19)	C17—C16—C21—C22	175.4 (2)
N3—N2—C5—C4	−4.4 (2)	C15—C16—C21—C22	−1.4 (3)
C7—N2—C5—C4	−139.91 (18)	C20—C21—C22—C23	176.4 (2)
N3—N2—C5—C6	174.48 (17)	C16—C21—C22—C23	−0.7 (3)
C7—N2—C5—C6	39.0 (3)	C21—C22—C23—O4	−177.26 (18)
C3—N3—C8—C13	−64.6 (3)	C21—C22—C23—C14	1.7 (3)
N2—N3—C8—C13	135.2 (2)	O3—C14—C23—O4	−0.8 (2)
C3—N3—C8—C9	115.5 (2)	C15—C14—C23—O4	178.42 (17)
N2—N3—C8—C9	−44.7 (3)	O3—C14—C23—C22	−179.90 (16)
C13—C8—C9—C10	−1.2 (3)	C15—C14—C23—C22	−0.6 (3)
N3—C8—C9—C10	178.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.87 (1)	2.07 (1)	2.924 (2)	169 (2)
O3—H3···O2	0.85 (3)	1.81 (3)	2.639 (2)	163 (3)
O4—H4···O1ⁱⁱ	0.85 (3)	1.81 (3)	2.646 (2)	168 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅N₃O₂·C₁₀H₈O₂
M_r	405.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.426 (1), 14.304 (2), 12.959 (1)
β (°)	117.845 (1)
V (Å³)	2036.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19263, 4683, 3189
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.131, 1.02
No. of reflections	4683
No. of parameters	286
No. of restraints	27
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.36

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.87 (1)	2.07 (1)	2.924 (2)	169 (2)
O3—H3···O2	0.85 (3)	1.81 (3)	2.639 (2)	163 (3)
O4—H4···O1ⁱⁱ	0.85 (3)	1.81 (3)	2.646 (2)	168 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2.

Acknowledgements

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fritchie, C. J. & Johnston, R. M. (1975). Acta Cryst. B31, 454–461. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Herbert, J. A. & Truter, M. R. (1980). J. Chem. Soc. Perkin Trans. 2, pp. 1253–1258. CrossRef Google Scholar
Kuo, M. C., Dunn, J. B. R. & Fritchie, C. J. (1974). Acta Cryst. B30, 1766–1771. CSD CrossRef IUCr Journals Web of Science Google Scholar
Kuznetsov, M. L., Bel'skii, V. K., Dement'ev, A. I., Zaitsev, B. E., Lokshin, B. V. & Zhornik, V. G. (1999). Russ. Chem. Bull. 48, 1274–1280. Web of Science CrossRef CAS Google Scholar
Nakamatsu, S., Yoshizawa, K., Toyota, S., Toda, F. & Matijasic, I. (2003). Org. Biomol. Chem. 1, 2231–2234. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y.-T., Tang, G.-M. & Wan, W.-Z. (2008). Acta Cryst. E64, o1754. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wells, J. L., Trus, B. L., Johnston, R. M., Marsh, R. E. & Fritchie, C. J. (1974). Acta Cryst. B30, 1127–1134. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar

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Volume 66| Part 7| July 2010| Page o1850

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

N-(1,5-Di­methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)acetamide–naphthalene-2,3-diol (1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide–naphthalene-2,3-diol (1/1)