N'-tert-Butyl-5-(4-chloro-phen-yl)furan-2-carbohydrazide.

In the title mol-ecule, C(15)H(17)ClN(2)O(2), the furan and benzene rings form a dihedral angle of 15.35 (8)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains extended in the [010] direction.

Related literature

For general background, see: Wing (1988 ▶); Wing et al. (1988 ▶); Dhadialla et al. (1998 ▶); Heller et al. (1992 ▶); Mao et al. (2004 ▶). For details of some monoacyl­hydrazines and diacyl­hydrazines containing furan, see: Yang et al. (2002 ▶); Li et al. (2006 ▶).

Experimental

Crystal data

C15H17ClN2O2

M = 292.76

Orthorhombic,

a = 9.3770 (7) Å

b = 9.7861 (7) Å

c = 16.0119 (12) Å

V = 1469.32 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 113 (2) K

0.32 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.921, T max = 0.949

13814 measured reflections

3496 independent reflections

2754 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.056

S = 0.96

3496 reflections

192 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1490 Friedel pairs

Flack parameter: 0.00 (4)

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003486/cv2380sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003486/cv2380Isup2.hkl

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

C15H17ClN2O2	Dx = 1.323 Mg m−3
Mr = 292.76	Mo Kα radiation λ = 0.71070 Å
Orthorhombic, P212121	Cell parameters from 3053 reflections
a = 9.3770 (7) Å	θ = 2.5–25.0º
b = 9.7861 (7) Å	µ = 0.26 mm−1
c = 16.0119 (12) Å	T = 113 (2) K
V = 1469.32 (19) Å3	Prism, colourless
Z = 4	0.32 × 0.24 × 0.20 mm
F000 = 616

Rigaku Saturn diffractometer	3496 independent reflections
Radiation source: rotating anode	2754 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.039
Detector resolution: 7.31 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 2.4º
ω scans	h = −12→12
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −12→12
Tmin = 0.921, Tmax = 0.949	l = −21→21
13814 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(Fo2) + (0.0232P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.056	(Δ/σ)max = 0.001
S = 0.96	Δρmax = 0.22 e Å−3
3496 reflections	Δρmin = −0.21 e Å−3
192 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1490 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (4)

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
Cl1	1.32887 (4)	0.17773 (4)	1.09957 (2)	0.02303 (9)
O1	1.13067 (10)	0.70996 (9)	0.86903 (6)	0.0151 (2)
O2	0.98638 (10)	0.97666 (9)	0.74249 (6)	0.0174 (2)
N1	0.91782 (13)	0.75551 (12)	0.76336 (7)	0.0151 (3)
N2	0.80263 (13)	0.76074 (12)	0.70613 (7)	0.0146 (3)
C1	1.30520 (15)	0.33360 (15)	1.04901 (8)	0.0159 (3)
C2	1.17767 (16)	0.35872 (14)	1.00795 (8)	0.0168 (3)
H2	1.1040	0.2921	1.0078	0.020*
C3	1.15907 (16)	0.48241 (13)	0.96720 (8)	0.0159 (3)
H3	1.0720	0.5002	0.9389	0.019*
C4	1.26701 (15)	0.58168 (15)	0.96708 (9)	0.0149 (3)
C5	1.39448 (15)	0.55382 (14)	1.00941 (8)	0.0176 (3)
H5	1.4685	0.6201	1.0100	0.021*
C6	1.41381 (15)	0.43007 (14)	1.05056 (9)	0.0175 (3)
H6	1.5003	0.4117	1.0794	0.021*
C7	1.24400 (15)	0.71056 (14)	0.92346 (8)	0.0153 (3)
C8	1.30641 (15)	0.83596 (15)	0.92271 (8)	0.0175 (3)
H8	1.3868	0.8635	0.9547	0.021*
C9	1.22900 (14)	0.91848 (15)	0.86505 (9)	0.0165 (3)
H9	1.2472	1.0113	0.8515	0.020*
C10	1.12421 (14)	0.83819 (14)	0.83345 (8)	0.0137 (3)
C11	1.00485 (15)	0.86322 (14)	0.77523 (8)	0.0138 (3)
C12	0.66234 (15)	0.78352 (14)	0.74892 (9)	0.0163 (3)
C13	0.65461 (17)	0.92221 (15)	0.79274 (9)	0.0240 (4)
H13A	0.7283	0.9270	0.8360	0.036*
H13B	0.5604	0.9333	0.8184	0.036*
H13C	0.6701	0.9952	0.7518	0.036*
C14	0.55159 (16)	0.77717 (16)	0.67895 (10)	0.0241 (4)
H14A	0.5713	0.8491	0.6380	0.036*
H14B	0.4561	0.7906	0.7025	0.036*
H14C	0.5563	0.6877	0.6516	0.036*
C15	0.63850 (16)	0.66767 (15)	0.81165 (9)	0.0230 (3)
H15A	0.6501	0.5795	0.7834	0.035*
H15B	0.5419	0.6742	0.8347	0.035*
H15C	0.7083	0.6751	0.8570	0.035*
H2A	0.8186 (15)	0.8364 (13)	0.6731 (8)	0.012 (4)*
H1A	0.9484 (16)	0.6722 (16)	0.7743 (9)	0.029 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02355 (19)	0.02007 (19)	0.0255 (2)	0.00437 (17)	−0.00042 (17)	0.00723 (17)
O1	0.0162 (5)	0.0122 (5)	0.0169 (5)	0.0000 (4)	−0.0040 (4)	0.0010 (4)
O2	0.0205 (5)	0.0104 (5)	0.0214 (5)	−0.0001 (4)	−0.0019 (5)	0.0019 (4)
N1	0.0154 (6)	0.0107 (7)	0.0192 (7)	0.0012 (5)	−0.0047 (5)	0.0004 (5)
N2	0.0145 (7)	0.0146 (7)	0.0146 (6)	0.0003 (5)	−0.0032 (5)	0.0022 (5)
C1	0.0218 (8)	0.0154 (7)	0.0105 (7)	0.0048 (7)	0.0022 (6)	0.0016 (6)
C2	0.0168 (7)	0.0180 (8)	0.0157 (7)	−0.0019 (6)	0.0012 (7)	−0.0011 (6)
C3	0.0146 (7)	0.0187 (8)	0.0144 (7)	0.0016 (6)	−0.0031 (6)	−0.0010 (6)
C4	0.0157 (7)	0.0162 (8)	0.0128 (7)	0.0021 (6)	−0.0004 (6)	−0.0034 (6)
C5	0.0180 (8)	0.0172 (8)	0.0177 (8)	−0.0014 (6)	−0.0022 (6)	−0.0043 (6)
C6	0.0157 (8)	0.0225 (8)	0.0144 (8)	0.0045 (7)	−0.0029 (6)	−0.0021 (6)
C7	0.0125 (7)	0.0185 (8)	0.0150 (8)	0.0015 (6)	−0.0024 (6)	−0.0025 (6)
C8	0.0137 (7)	0.0185 (7)	0.0202 (8)	−0.0026 (6)	−0.0021 (6)	−0.0018 (6)
C9	0.0169 (7)	0.0129 (7)	0.0196 (8)	−0.0008 (6)	0.0022 (6)	0.0011 (6)
C10	0.0157 (7)	0.0106 (7)	0.0149 (7)	0.0023 (6)	0.0015 (6)	0.0004 (6)
C11	0.0139 (7)	0.0139 (8)	0.0137 (7)	0.0019 (6)	0.0041 (6)	−0.0023 (6)
C12	0.0134 (7)	0.0168 (7)	0.0187 (8)	0.0007 (6)	−0.0017 (7)	0.0000 (6)
C13	0.0207 (9)	0.0222 (8)	0.0292 (9)	0.0024 (7)	−0.0007 (7)	−0.0052 (7)
C14	0.0209 (8)	0.0245 (9)	0.0270 (9)	0.0008 (7)	−0.0075 (7)	0.0012 (7)
C15	0.0224 (8)	0.0230 (8)	0.0237 (8)	−0.0003 (8)	−0.0005 (7)	0.0029 (7)

Cl1—C1	1.7411 (14)	C6—H6	0.9500
O1—C7	1.3744 (15)	C7—C8	1.360 (2)
O1—C10	1.3795 (16)	C8—C9	1.4252 (19)
O2—C11	1.2398 (15)	C8—H8	0.9500
N1—C11	1.3465 (17)	C9—C10	1.3561 (18)
N1—N2	1.4174 (16)	C9—H9	0.9500
N1—H1A	0.882 (15)	C10—C11	1.4771 (19)
N2—C12	1.4999 (18)	C12—C14	1.5289 (19)
N2—H2A	0.922 (13)	C12—C13	1.5296 (18)
C1—C2	1.3866 (19)	C12—C15	1.5311 (18)
C1—C6	1.3889 (19)	C13—H13A	0.9800
C2—C3	1.3861 (17)	C13—H13B	0.9800
C2—H2	0.9500	C13—H13C	0.9800
C3—C4	1.4029 (19)	C14—H14A	0.9800
C3—H3	0.9500	C14—H14B	0.9800
C4—C5	1.4009 (18)	C14—H14C	0.9800
C4—C7	1.4578 (19)	C15—H15A	0.9800
C5—C6	1.3906 (19)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
C7—O1—C10	106.97 (10)	C10—C9—H9	126.8
C11—N1—N2	121.66 (12)	C8—C9—H9	126.8
C11—N1—H1A	119.9 (10)	C9—C10—O1	109.95 (12)
N2—N1—H1A	114.2 (10)	C9—C10—C11	133.51 (13)
N1—N2—C12	112.24 (10)	O1—C10—C11	116.41 (12)
N1—N2—H2A	106.0 (9)	O2—C11—N1	123.82 (13)
C12—N2—H2A	106.6 (9)	O2—C11—C10	121.41 (13)
C2—C1—C6	121.36 (13)	N1—C11—C10	114.74 (12)
C2—C1—Cl1	119.06 (11)	N2—C12—C14	104.77 (11)
C6—C1—Cl1	119.58 (11)	N2—C12—C13	112.52 (12)
C3—C2—C1	119.11 (13)	C14—C12—C13	109.88 (12)
C3—C2—H2	120.4	N2—C12—C15	108.52 (11)
C1—C2—H2	120.4	C14—C12—C15	110.58 (12)
C2—C3—C4	120.97 (14)	C13—C12—C15	110.44 (12)
C2—C3—H3	119.5	C12—C13—H13A	109.5
C4—C3—H3	119.5	C12—C13—H13B	109.5
C5—C4—C3	118.69 (13)	H13A—C13—H13B	109.5
C5—C4—C7	121.77 (13)	C12—C13—H13C	109.5
C3—C4—C7	119.54 (13)	H13A—C13—H13C	109.5
C6—C5—C4	120.66 (13)	H13B—C13—H13C	109.5
C6—C5—H5	119.7	C12—C14—H14A	109.5
C4—C5—H5	119.7	C12—C14—H14B	109.5
C1—C6—C5	119.20 (13)	H14A—C14—H14B	109.5
C1—C6—H6	120.4	C12—C14—H14C	109.5
C5—C6—H6	120.4	H14A—C14—H14C	109.5
C8—C7—O1	109.33 (12)	H14B—C14—H14C	109.5
C8—C7—C4	136.18 (13)	C12—C15—H15A	109.5
O1—C7—C4	114.49 (12)	C12—C15—H15B	109.5
C7—C8—C9	107.33 (13)	H15A—C15—H15B	109.5
C7—C8—H8	126.3	C12—C15—H15C	109.5
C9—C8—H8	126.3	H15A—C15—H15C	109.5
C10—C9—C8	106.41 (13)	H15B—C15—H15C	109.5
C11—N1—N2—C12	−101.13 (14)	O1—C7—C8—C9	−0.05 (16)
C6—C1—C2—C3	0.5 (2)	C4—C7—C8—C9	−179.46 (15)
Cl1—C1—C2—C3	−179.57 (10)	C7—C8—C9—C10	−0.42 (16)
C1—C2—C3—C4	0.0 (2)	C8—C9—C10—O1	0.73 (16)
C2—C3—C4—C5	−0.3 (2)	C8—C9—C10—C11	176.25 (14)
C2—C3—C4—C7	179.88 (13)	C7—O1—C10—C9	−0.77 (15)
C3—C4—C5—C6	0.2 (2)	C7—O1—C10—C11	−177.14 (11)
C7—C4—C5—C6	180.00 (13)	N2—N1—C11—O2	5.2 (2)
C2—C1—C6—C5	−0.6 (2)	N2—N1—C11—C10	−176.72 (11)
Cl1—C1—C6—C5	179.45 (10)	C9—C10—C11—O2	1.9 (2)
C4—C5—C6—C1	0.3 (2)	O1—C10—C11—O2	177.18 (12)
C10—O1—C7—C8	0.49 (14)	C9—C10—C11—N1	−176.21 (15)
C10—O1—C7—C4	−179.95 (11)	O1—C10—C11—N1	−0.92 (17)
C5—C4—C7—C8	−15.6 (3)	N1—N2—C12—C14	−176.55 (11)
C3—C4—C7—C8	164.26 (16)	N1—N2—C12—C13	64.11 (15)
C5—C4—C7—O1	165.04 (12)	N1—N2—C12—C15	−58.41 (14)
C3—C4—C7—O1	−15.13 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.882 (15)	2.026 (16)	2.8744 (15)	160.9 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.882 (15)	2.026 (16)	2.8744 (15)	160.9 (14)

Symmetry code: (i) .