3-(2,5-Dimethyl-furan-3-yl)-1H-pyrazol-5-ol-ethyl 3-(propan-2-yl-idene)carbazate (1/1).

In the title 1:1 adduct, C(6)H(12)N(2)O(2)·C(9)H(10)N(2)O(2), the maximum deviations from the 1H-pyrazole-5-ol and furan rings are 0.014 (1) and 0.003 (1) Å, respectively. The dihedral angle formed between the 1H-pyrazol-5-ol and 2,5-dimethyl-furan rings is 21.07 (5)°. In the crystal, pairs of inter-molecular O-H⋯N hydrogen bonds form inversion dimers of the 3-(2,5-dimethyl-furan-3-yl)-1H-pyrazol-5-ol species, generating R(2) (2)(8) ring motifs. Mol-ecules are further linked by inter-molecular N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds to form ribbons along the [010] direction containing bifurcated R(1) (2)(5) and R(2) (1)(7) ring motifs. Further stablization of the packing is provided by weak π-π [centroid-centroid distance = 3.5686 (15) Å] and C-H⋯π inter-actions.

Related literature

For pyrazole derivatives and their microbial activities, see: Ragavan et al. (2009 ▶, 2010 ▶). For a related structure, see: Shahani et al. (2010 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C6H12N2O2·C9n class="Species">H10N2O2

M = 322.37

Triclinic,

a = 8.6988 (17) Å

b = 9.4830 (19) Å

c = 11.837 (4) Å

α = 107.293 (4)°

β = 100.354 (5)°

γ = 108.346 (3)°

V = 843.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.21 × 0.13 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.964, T max = 0.988

13322 measured reflections

3264 independent reflections

2911 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.099

S = 1.11

3264 reflections

225 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.22 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/S1600536810043886/hb5696sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043886/hb5696Isup2.hkl

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

C6H12N2O2·C9H10N2O2	Z = 2
Mr = 322.37	F(000) = 344
Triclinic, P1	Dx = 1.269 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6988 (17) Å	Cell parameters from 7782 reflections
b = 9.4830 (19) Å	θ = 2.6–31.7°
c = 11.837 (4) Å	µ = 0.09 mm−1
α = 107.293 (4)°	T = 100 K
β = 100.354 (5)°	Block, colourless
γ = 108.346 (3)°	0.40 × 0.21 × 0.13 mm
V = 843.7 (3) Å3

Bruker APEXII DUO CCD diffractometer	3264 independent reflections
Radiation source: fine-focus sealed tube	2911 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.964, Tmax = 0.988	k = −11→11
13322 measured reflections	l = −14→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.045P)2 + 0.2939P] where P = (Fo2 + 2Fc2)/3
3264 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.22 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 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	0.72298 (12)	0.49965 (12)	−0.03577 (8)	0.0272 (2)
O2	1.41202 (12)	1.13027 (10)	0.43430 (9)	0.0232 (2)
N1	1.21447 (13)	0.71967 (13)	0.29969 (10)	0.0197 (2)
N2	1.34466 (13)	0.85605 (12)	0.38574 (9)	0.0190 (2)
C1	1.31074 (15)	0.97528 (15)	0.36573 (11)	0.0185 (3)
C2	1.16205 (16)	0.91874 (15)	0.26795 (12)	0.0211 (3)
H2A	1.1136	0.9791	0.2366	0.025*
C3	1.10286 (15)	0.75316 (15)	0.22806 (11)	0.0185 (3)
C4	0.95185 (16)	0.62751 (15)	0.13126 (11)	0.0201 (3)
C5	0.87164 (16)	0.46384 (15)	0.11997 (12)	0.0222 (3)
H5A	0.9076	0.4169	0.1725	0.027*
C6	0.73478 (17)	0.39202 (16)	0.01874 (12)	0.0252 (3)
C7	0.85745 (16)	0.64286 (16)	0.03429 (12)	0.0240 (3)
C8	0.8742 (2)	0.77483 (18)	−0.01199 (14)	0.0344 (3)
H8A	0.9922	0.8414	0.0089	0.052*
H8B	0.8166	0.8382	0.0257	0.052*
H8C	0.8246	0.7301	−0.1005	0.052*
C9	0.59939 (19)	0.22804 (18)	−0.04258 (14)	0.0342 (3)
H9A	0.6186	0.1632	0.0027	0.051*
H9B	0.6011	0.1810	−0.1260	0.051*
H9C	0.4909	0.2338	−0.0441	0.051*
O3	0.08857 (11)	0.22838 (11)	0.42456 (9)	0.0236 (2)
O4	0.06433 (11)	0.42612 (11)	0.36063 (9)	0.0244 (2)
N3	0.29597 (14)	0.35988 (13)	0.36500 (10)	0.0209 (2)
N4	0.37772 (13)	0.48909 (12)	0.33504 (10)	0.0201 (2)
C10	−0.21443 (18)	0.07821 (18)	0.31978 (15)	0.0346 (3)
H10A	−0.3233	0.0471	0.3338	0.052*
H10B	−0.1904	−0.0153	0.2871	0.052*
H10C	−0.2154	0.1302	0.2615	0.052*
C11	−0.07996 (17)	0.19197 (17)	0.44018 (13)	0.0267 (3)
H11A	−0.0984	0.2905	0.4695	0.032*
H11B	−0.0878	0.1443	0.5021	0.032*
C12	0.14196 (16)	0.34622 (14)	0.38212 (11)	0.0194 (3)
C13	0.52197 (16)	0.50193 (15)	0.31731 (11)	0.0212 (3)
C14	0.60676 (18)	0.38865 (18)	0.32513 (14)	0.0300 (3)
H14A	0.6155	0.3777	0.4039	0.045*
H14B	0.7183	0.4299	0.3169	0.045*
H14C	0.5408	0.2856	0.2596	0.045*
C15	0.61073 (17)	0.64131 (16)	0.28562 (13)	0.0249 (3)
H15A	0.5436	0.7044	0.2843	0.037*
H15B	0.6259	0.6025	0.2054	0.037*
H15C	0.7196	0.7063	0.3468	0.037*
H1N1	1.211 (2)	0.626 (2)	0.3012 (15)	0.033 (4)*
H1N3	0.347 (2)	0.304 (2)	0.3897 (15)	0.031 (4)*
H1O2	1.496 (3)	1.138 (2)	0.500 (2)	0.057 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0228 (5)	0.0284 (5)	0.0227 (5)	0.0062 (4)	0.0009 (4)	0.0068 (4)
O2	0.0222 (5)	0.0154 (4)	0.0274 (5)	0.0068 (4)	−0.0018 (4)	0.0078 (4)
N1	0.0200 (5)	0.0146 (5)	0.0221 (5)	0.0065 (4)	0.0026 (4)	0.0061 (4)
N2	0.0178 (5)	0.0157 (5)	0.0215 (5)	0.0065 (4)	0.0028 (4)	0.0061 (4)
C1	0.0190 (6)	0.0173 (6)	0.0212 (6)	0.0085 (5)	0.0067 (5)	0.0080 (5)
C2	0.0209 (6)	0.0212 (6)	0.0231 (6)	0.0115 (5)	0.0041 (5)	0.0090 (5)
C3	0.0174 (6)	0.0216 (6)	0.0187 (6)	0.0095 (5)	0.0070 (5)	0.0079 (5)
C4	0.0190 (6)	0.0218 (6)	0.0194 (6)	0.0090 (5)	0.0073 (5)	0.0059 (5)
C5	0.0215 (6)	0.0224 (6)	0.0217 (6)	0.0084 (5)	0.0074 (5)	0.0069 (5)
C6	0.0233 (7)	0.0258 (7)	0.0243 (7)	0.0080 (5)	0.0089 (5)	0.0073 (5)
C7	0.0211 (6)	0.0246 (7)	0.0221 (6)	0.0075 (5)	0.0043 (5)	0.0060 (5)
C8	0.0364 (8)	0.0329 (8)	0.0294 (7)	0.0115 (7)	−0.0003 (6)	0.0139 (6)
C9	0.0279 (7)	0.0295 (8)	0.0323 (8)	0.0019 (6)	0.0049 (6)	0.0067 (6)
O3	0.0212 (5)	0.0240 (5)	0.0319 (5)	0.0101 (4)	0.0109 (4)	0.0159 (4)
O4	0.0234 (5)	0.0235 (5)	0.0314 (5)	0.0129 (4)	0.0088 (4)	0.0133 (4)
N3	0.0214 (5)	0.0195 (5)	0.0282 (6)	0.0108 (5)	0.0090 (4)	0.0139 (5)
N4	0.0217 (5)	0.0185 (5)	0.0218 (5)	0.0084 (4)	0.0064 (4)	0.0093 (4)
C10	0.0259 (7)	0.0307 (8)	0.0430 (9)	0.0076 (6)	0.0118 (6)	0.0112 (7)
C11	0.0232 (7)	0.0288 (7)	0.0340 (7)	0.0104 (6)	0.0152 (6)	0.0156 (6)
C12	0.0218 (6)	0.0168 (6)	0.0187 (6)	0.0079 (5)	0.0045 (5)	0.0063 (5)
C13	0.0221 (6)	0.0226 (6)	0.0196 (6)	0.0100 (5)	0.0061 (5)	0.0079 (5)
C14	0.0310 (7)	0.0334 (8)	0.0411 (8)	0.0207 (6)	0.0195 (6)	0.0215 (7)
C15	0.0234 (7)	0.0261 (7)	0.0293 (7)	0.0108 (5)	0.0100 (5)	0.0138 (6)

O1—C7	1.3719 (16)	C9—H9C	0.9600
O1—C6	1.3792 (17)	O3—C12	1.3445 (15)
O2—C1	1.3468 (15)	O3—C11	1.4558 (15)
O2—H1O2	0.93 (2)	O4—C12	1.2124 (15)
N1—C3	1.3493 (16)	N3—C12	1.3625 (17)
N1—N2	1.3685 (14)	N3—N4	1.3905 (15)
N1—H1N1	0.883 (18)	N3—H1N3	0.872 (18)
N2—C1	1.3288 (16)	N4—C13	1.2834 (17)
C1—C2	1.3988 (18)	C10—C11	1.502 (2)
C2—C3	1.3844 (18)	C10—H10A	0.9600
C2—H2A	0.9300	C10—H10B	0.9600
C3—C4	1.4561 (18)	C10—H10C	0.9600
C4—C7	1.3597 (19)	C11—H11A	0.9700
C4—C5	1.4405 (18)	C11—H11B	0.9700
C5—C6	1.3448 (19)	C13—C14	1.4967 (19)
C5—H5A	0.9300	C13—C15	1.4967 (18)
C6—C9	1.4835 (19)	C14—H14A	0.9600
C7—C8	1.486 (2)	C14—H14B	0.9600
C8—H8A	0.9600	C14—H14C	0.9600
C8—H8B	0.9600	C15—H15A	0.9600
C8—H8C	0.9600	C15—H15B	0.9600
C9—H9A	0.9600	C15—H15C	0.9600
C9—H9B	0.9600
C7—O1—C6	107.17 (10)	H9A—C9—H9C	109.5
C1—O2—H1O2	110.5 (13)	H9B—C9—H9C	109.5
C3—N1—N2	111.95 (10)	C12—O3—C11	115.88 (10)
C3—N1—H1N1	129.8 (11)	C12—N3—N4	116.20 (11)
N2—N1—H1N1	118.1 (11)	C12—N3—H1N3	119.0 (11)
C1—N2—N1	104.49 (10)	N4—N3—H1N3	123.2 (11)
N2—C1—O2	121.83 (11)	C13—N4—N3	116.67 (11)
N2—C1—C2	111.95 (11)	C11—C10—H10A	109.5
O2—C1—C2	126.22 (11)	C11—C10—H10B	109.5
C3—C2—C1	104.84 (11)	H10A—C10—H10B	109.5
C3—C2—H2A	127.6	C11—C10—H10C	109.5
C1—C2—H2A	127.6	H10A—C10—H10C	109.5
N1—C3—C2	106.77 (11)	H10B—C10—H10C	109.5
N1—C3—C4	122.08 (11)	O3—C11—C10	110.77 (11)
C2—C3—C4	131.15 (12)	O3—C11—H11A	109.5
C7—C4—C5	106.49 (11)	C10—C11—H11A	109.5
C7—C4—C3	126.43 (12)	O3—C11—H11B	109.5
C5—C4—C3	127.08 (12)	C10—C11—H11B	109.5
C6—C5—C4	106.74 (12)	H11A—C11—H11B	108.1
C6—C5—H5A	126.6	O4—C12—O3	125.45 (12)
C4—C5—H5A	126.6	O4—C12—N3	125.31 (12)
C5—C6—O1	109.97 (12)	O3—C12—N3	109.22 (10)
C5—C6—C9	134.00 (13)	N4—C13—C14	125.22 (12)
O1—C6—C9	116.02 (12)	N4—C13—C15	116.82 (12)
C4—C7—O1	109.62 (12)	C14—C13—C15	117.96 (11)
C4—C7—C8	134.17 (13)	C13—C14—H14A	109.5
O1—C7—C8	116.15 (11)	C13—C14—H14B	109.5
C7—C8—H8A	109.5	H14A—C14—H14B	109.5
C7—C8—H8B	109.5	C13—C14—H14C	109.5
H8A—C8—H8B	109.5	H14A—C14—H14C	109.5
C7—C8—H8C	109.5	H14B—C14—H14C	109.5
H8A—C8—H8C	109.5	C13—C15—H15A	109.5
H8B—C8—H8C	109.5	C13—C15—H15B	109.5
C6—C9—H9A	109.5	H15A—C15—H15B	109.5
C6—C9—H9B	109.5	C13—C15—H15C	109.5
H9A—C9—H9B	109.5	H15A—C15—H15C	109.5
C6—C9—H9C	109.5	H15B—C15—H15C	109.5
C3—N1—N2—C1	0.09 (13)	C7—O1—C6—C5	0.06 (14)
N1—N2—C1—O2	179.58 (11)	C7—O1—C6—C9	179.60 (11)
N1—N2—C1—C2	−0.44 (14)	C5—C4—C7—O1	0.55 (14)
N2—C1—C2—C3	0.62 (14)	C3—C4—C7—O1	−178.68 (11)
O2—C1—C2—C3	−179.40 (11)	C5—C4—C7—C8	−176.26 (16)
N2—N1—C3—C2	0.30 (14)	C3—C4—C7—C8	4.5 (2)
N2—N1—C3—C4	−178.86 (10)	C6—O1—C7—C4	−0.39 (14)
C1—C2—C3—N1	−0.53 (13)	C6—O1—C7—C8	177.06 (12)
C1—C2—C3—C4	178.51 (12)	C12—N3—N4—C13	−179.21 (11)
N1—C3—C4—C7	−161.23 (13)	C12—O3—C11—C10	84.10 (14)
C2—C3—C4—C7	19.8 (2)	C11—O3—C12—O4	2.70 (18)
N1—C3—C4—C5	19.70 (19)	C11—O3—C12—N3	−176.27 (10)
C2—C3—C4—C5	−159.23 (13)	N4—N3—C12—O4	8.26 (18)
C7—C4—C5—C6	−0.50 (14)	N4—N3—C12—O3	−172.77 (10)
C3—C4—C5—C6	178.72 (12)	N3—N4—C13—C14	0.65 (19)
C4—C5—C6—O1	0.27 (14)	N3—N4—C13—C15	−179.72 (11)
C4—C5—C6—C9	−179.15 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4i	0.883 (18)	2.304 (19)	3.0363 (19)	140.1 (16)
N1—H1N1···N4i	0.883 (18)	2.288 (19)	3.043 (2)	143.1 (16)
N3—H1N3···O2ii	0.872 (18)	2.076 (19)	2.9293 (19)	166.7 (18)
O2—H1O2···N2iii	0.93 (2)	1.73 (2)	2.6602 (17)	176 (2)
C5—H5A···O4i	0.93	2.35	3.212 (2)	153
C11—H11B···Cg2iv	0.97	2.71	3.498 (20)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O4i	0.883 (18)	2.304 (19)	3.0363 (19)	140.1 (16)
N1—H1N1⋯N4i	0.883 (18)	2.288 (19)	3.043 (2)	143.1 (16)
N3—H1N3⋯O2ii	0.872 (18)	2.076 (19)	2.9293 (19)	166.7 (18)
O2—H1O2⋯N2iii	0.93 (2)	1.73 (2)	2.6602 (17)	176 (2)
C5—H5A⋯O4i	0.93	2.35	3.212 (2)	153
C11—H11B⋯Cg2iv	0.97	2.71	3.50 (2)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the 1H-pyrazole ring (N1/N2/C1–C3).