2-Cyclo-pentyl-idenehydrazine-carboxamide.

The asymmetric unit of the title compound, C(6)H(11)N(3)O, consists of two independent mol-ecules in which the cyclo-pentane rings adopt envelope conformations with CH(2) grouping as the flap and the semicarbazone groups are essentially planar, with maximums deviation of 0.0311 (12) and 0.0285 (12) Å. In the crystal, N-H⋯O, N-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules to form sheets lying parallel to the ab plane.

Related literature

For background to the biological activity of semicarbazones, see: Dogan et al. (1999 ▶); Pandeya & Dimmock (1993 ▶); Pandeya et al. (1998 ▶); Yogeeswari et al. (2004 ▶); Sriram et al. (2004 ▶); Fun et al. (2011 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶). For further synthetic details, see: Furniss et al. (1978 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C6H11N3O

M = 141.18

Monoclinic,

a = 8.9507 (1) Å

b = 10.7929 (2) Å

c = 15.0204 (2) Å

β = 95.126 (1)°

V = 1445.23 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.964, T max = 0.995

14322 measured reflections

4231 independent reflections

3120 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.114

S = 1.00

4231 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.30 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 datablock(s) global, I. DOI: 10.1107/S1600536812034599/hb6915sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034599/hb6915Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034599/hb6915Isup3.cml

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

C6H11N3O	F(000) = 608
Mr = 141.18	Dx = 1.298 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3109 reflections
a = 8.9507 (1) Å	θ = 2.7–29.3°
b = 10.7929 (2) Å	µ = 0.09 mm−1
c = 15.0204 (2) Å	T = 100 K
β = 95.126 (1)°	Plate, colourless
V = 1445.23 (4) Å3	0.40 × 0.20 × 0.05 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	4231 independent reflections
Radiation source: fine-focus sealed tube	3120 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 30.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.964, Tmax = 0.995	k = −12→15
14322 measured reflections	l = −18→21

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.6439P] where P = (Fo2 + 2Fc2)/3
4231 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.30 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 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
O1B	0.14864 (10)	0.11961 (9)	0.00969 (7)	0.0163 (2)
N1B	−0.03324 (12)	0.35060 (10)	0.12404 (8)	0.0142 (2)
N2B	0.07174 (12)	0.29357 (11)	0.07505 (8)	0.0148 (2)
N3B	−0.07584 (13)	0.11717 (12)	0.06934 (9)	0.0180 (3)
C1B	−0.11403 (15)	0.53548 (13)	0.19876 (10)	0.0179 (3)
H1BA	−0.0892	0.5196	0.2633	0.021*
H1BB	−0.2200	0.5125	0.1824	0.021*
C2B	−0.08570 (15)	0.67107 (13)	0.17588 (10)	0.0196 (3)
H2BA	−0.1079	0.7264	0.2256	0.024*
H2BB	−0.1479	0.6964	0.1211	0.024*
C3B	0.08159 (15)	0.67431 (13)	0.16132 (10)	0.0187 (3)
H3BA	0.1436	0.6815	0.2190	0.022*
H3BB	0.1043	0.7450	0.1227	0.022*
C4B	0.11103 (14)	0.55001 (12)	0.11528 (9)	0.0154 (3)
H4BA	0.1036	0.5597	0.0495	0.018*
H4BB	0.2117	0.5175	0.1357	0.018*
C5B	−0.01062 (14)	0.46502 (12)	0.14338 (9)	0.0140 (3)
C6B	0.05040 (14)	0.17321 (12)	0.04950 (9)	0.0132 (3)
O1A	0.35640 (10)	0.37841 (9)	0.00812 (7)	0.0169 (2)
N1A	0.57800 (12)	0.13301 (11)	0.09989 (8)	0.0145 (2)
N2A	0.45488 (12)	0.19836 (11)	0.06156 (8)	0.0153 (3)
N3A	0.60763 (13)	0.36934 (12)	0.04762 (9)	0.0194 (3)
C1A	0.67282 (15)	−0.05543 (13)	0.17484 (10)	0.0173 (3)
H1AA	0.7522	−0.0047	0.2072	0.021*
H1AB	0.7184	−0.1093	0.1313	0.021*
C2A	0.58742 (15)	−0.13169 (14)	0.23954 (10)	0.0202 (3)
H2AA	0.5718	−0.0837	0.2941	0.024*
H2AB	0.6417	−0.2091	0.2569	0.024*
C3A	0.43811 (16)	−0.15927 (14)	0.18545 (10)	0.0208 (3)
H3AA	0.3591	−0.1788	0.2254	0.025*
H3AB	0.4482	−0.2299	0.1444	0.025*
C4A	0.40070 (15)	−0.03906 (13)	0.13277 (10)	0.0176 (3)
H4AA	0.3551	−0.0577	0.0718	0.021*
H4AB	0.3307	0.0133	0.1637	0.021*
C5A	0.55099 (14)	0.02476 (12)	0.12953 (9)	0.0137 (3)
C6A	0.47038 (14)	0.31899 (12)	0.03773 (9)	0.0138 (3)
H1N2	0.3656 (19)	0.1655 (16)	0.0516 (12)	0.028 (5)*
H1N3	0.682 (2)	0.3267 (17)	0.0710 (12)	0.030 (5)*
H2N3	0.6182 (19)	0.4510 (18)	0.0303 (12)	0.028 (5)*
H2N2	0.1582 (19)	0.3309 (16)	0.0600 (12)	0.027 (5)*
H3N3	−0.0968 (19)	0.0420 (18)	0.0474 (12)	0.028 (5)*
H4N3	−0.1441 (19)	0.1587 (16)	0.0927 (12)	0.026 (5)*

	U11	U22	U33	U12	U13	U23
O1B	0.0139 (4)	0.0136 (5)	0.0217 (5)	0.0001 (3)	0.0040 (4)	−0.0029 (4)
N1B	0.0147 (5)	0.0156 (6)	0.0128 (5)	0.0013 (4)	0.0032 (4)	−0.0006 (4)
N2B	0.0128 (5)	0.0126 (6)	0.0197 (6)	−0.0009 (4)	0.0059 (4)	−0.0018 (5)
N3B	0.0165 (5)	0.0131 (6)	0.0255 (7)	−0.0022 (5)	0.0082 (5)	−0.0039 (5)
C1B	0.0174 (6)	0.0177 (7)	0.0189 (7)	−0.0005 (5)	0.0038 (5)	−0.0045 (6)
C2B	0.0204 (6)	0.0168 (7)	0.0214 (7)	0.0043 (5)	0.0000 (5)	−0.0050 (6)
C3B	0.0205 (6)	0.0138 (7)	0.0216 (7)	−0.0006 (5)	−0.0001 (6)	−0.0026 (6)
C4B	0.0153 (6)	0.0150 (6)	0.0158 (7)	0.0005 (5)	0.0015 (5)	−0.0005 (5)
C5B	0.0141 (6)	0.0143 (6)	0.0136 (6)	0.0001 (5)	0.0002 (5)	0.0007 (5)
C6B	0.0138 (6)	0.0127 (6)	0.0128 (6)	0.0006 (5)	−0.0006 (5)	0.0009 (5)
O1A	0.0136 (4)	0.0144 (5)	0.0226 (5)	0.0005 (4)	0.0006 (4)	0.0020 (4)
N1A	0.0127 (5)	0.0149 (6)	0.0161 (6)	0.0025 (4)	0.0026 (4)	0.0001 (5)
N2A	0.0113 (5)	0.0129 (6)	0.0216 (6)	−0.0004 (4)	0.0007 (4)	0.0031 (5)
N3A	0.0132 (5)	0.0153 (6)	0.0293 (7)	−0.0007 (4)	0.0001 (5)	0.0057 (5)
C1A	0.0156 (6)	0.0190 (7)	0.0175 (7)	0.0021 (5)	0.0034 (5)	0.0042 (6)
C2A	0.0193 (7)	0.0233 (8)	0.0181 (7)	−0.0014 (6)	0.0032 (5)	0.0063 (6)
C3A	0.0213 (7)	0.0185 (7)	0.0225 (7)	−0.0054 (5)	0.0013 (6)	0.0064 (6)
C4A	0.0159 (6)	0.0174 (7)	0.0195 (7)	−0.0022 (5)	0.0019 (5)	0.0022 (6)
C5A	0.0149 (6)	0.0149 (7)	0.0118 (6)	0.0005 (5)	0.0036 (5)	−0.0012 (5)
C6A	0.0145 (6)	0.0143 (7)	0.0131 (6)	0.0001 (5)	0.0039 (5)	−0.0019 (5)

O1B—C6B	1.2488 (16)	O1A—C6A	1.2526 (15)
N1B—C5B	1.2806 (17)	N1A—C5A	1.2811 (18)
N1B—N2B	1.3882 (16)	N1A—N2A	1.3892 (14)
N2B—C6B	1.3631 (17)	N2A—C6A	1.3605 (17)
N2B—H2N2	0.919 (17)	N2A—H1N2	0.875 (17)
N3B—C6B	1.3385 (17)	N3A—C6A	1.3394 (17)
N3B—H3N3	0.889 (19)	N3A—H1N3	0.860 (18)
N3B—H4N3	0.858 (18)	N3A—H2N3	0.926 (19)
C1B—C5B	1.5049 (19)	C1A—C5A	1.5062 (17)
C1B—C2B	1.530 (2)	C1A—C2A	1.529 (2)
C1B—H1BA	0.9900	C1A—H1AA	0.9900
C1B—H1BB	0.9900	C1A—H1AB	0.9900
C2B—C3B	1.533 (2)	C2A—C3A	1.5300 (18)
C2B—H2BA	0.9900	C2A—H2AA	0.9900
C2B—H2BB	0.9900	C2A—H2AB	0.9900
C3B—C4B	1.5427 (19)	C3A—C4A	1.541 (2)
C3B—H3BA	0.9900	C3A—H3AA	0.9900
C3B—H3BB	0.9900	C3A—H3AB	0.9900
C4B—C5B	1.5124 (19)	C4A—C5A	1.5159 (18)
C4B—H4BA	0.9900	C4A—H4AA	0.9900
C4B—H4BB	0.9900	C4A—H4AB	0.9900
C5B—N1B—N2B	116.56 (11)	C5A—N1A—N2A	116.09 (11)
C6B—N2B—N1B	119.17 (11)	C6A—N2A—N1A	119.94 (11)
C6B—N2B—H2N2	116.7 (11)	C6A—N2A—H1N2	117.2 (12)
N1B—N2B—H2N2	124.1 (11)	N1A—N2A—H1N2	122.9 (12)
C6B—N3B—H3N3	118.9 (12)	C6A—N3A—H1N3	119.9 (12)
C6B—N3B—H4N3	120.1 (12)	C6A—N3A—H2N3	118.1 (10)
H3N3—N3B—H4N3	119.6 (16)	H1N3—N3A—H2N3	121.9 (16)
C5B—C1B—C2B	103.70 (12)	C5A—C1A—C2A	102.33 (11)
C5B—C1B—H1BA	111.0	C5A—C1A—H1AA	111.3
C2B—C1B—H1BA	111.0	C2A—C1A—H1AA	111.3
C5B—C1B—H1BB	111.0	C5A—C1A—H1AB	111.3
C2B—C1B—H1BB	111.0	C2A—C1A—H1AB	111.3
H1BA—C1B—H1BB	109.0	H1AA—C1A—H1AB	109.2
C1B—C2B—C3B	103.74 (11)	C1A—C2A—C3A	103.28 (11)
C1B—C2B—H2BA	111.0	C1A—C2A—H2AA	111.1
C3B—C2B—H2BA	111.0	C3A—C2A—H2AA	111.1
C1B—C2B—H2BB	111.0	C1A—C2A—H2AB	111.1
C3B—C2B—H2BB	111.0	C3A—C2A—H2AB	111.1
H2BA—C2B—H2BB	109.0	H2AA—C2A—H2AB	109.1
C2B—C3B—C4B	104.61 (11)	C2A—C3A—C4A	104.38 (11)
C2B—C3B—H3BA	110.8	C2A—C3A—H3AA	110.9
C4B—C3B—H3BA	110.8	C4A—C3A—H3AA	110.9
C2B—C3B—H3BB	110.8	C2A—C3A—H3AB	110.9
C4B—C3B—H3BB	110.8	C4A—C3A—H3AB	110.9
H3BA—C3B—H3BB	108.9	H3AA—C3A—H3AB	108.9
C5B—C4B—C3B	104.26 (11)	C5A—C4A—C3A	104.26 (10)
C5B—C4B—H4BA	110.9	C5A—C4A—H4AA	110.9
C3B—C4B—H4BA	110.9	C3A—C4A—H4AA	110.9
C5B—C4B—H4BB	110.9	C5A—C4A—H4AB	110.9
C3B—C4B—H4BB	110.9	C3A—C4A—H4AB	110.9
H4BA—C4B—H4BB	108.9	H4AA—C4A—H4AB	108.9
N1B—C5B—C1B	121.34 (12)	N1A—C5A—C1A	121.98 (11)
N1B—C5B—C4B	128.67 (13)	N1A—C5A—C4A	128.40 (12)
C1B—C5B—C4B	109.97 (11)	C1A—C5A—C4A	109.46 (11)
O1B—C6B—N3B	122.81 (12)	O1A—C6A—N3A	122.79 (13)
O1B—C6B—N2B	119.30 (12)	O1A—C6A—N2A	118.98 (11)
N3B—C6B—N2B	117.89 (12)	N3A—C6A—N2A	118.24 (12)
C5B—N1B—N2B—C6B	−177.45 (11)	C5A—N1A—N2A—C6A	172.46 (13)
C5B—C1B—C2B—C3B	−34.21 (13)	C5A—C1A—C2A—C3A	38.89 (14)
C1B—C2B—C3B—C4B	36.78 (14)	C1A—C2A—C3A—C4A	−38.43 (15)
C2B—C3B—C4B—C5B	−24.62 (14)	C2A—C3A—C4A—C5A	22.39 (15)
N2B—N1B—C5B—C1B	−177.98 (11)	N2A—N1A—C5A—C1A	−178.43 (12)
N2B—N1B—C5B—C4B	4.09 (19)	N2A—N1A—C5A—C4A	−3.6 (2)
C2B—C1B—C5B—N1B	−158.97 (12)	C2A—C1A—C5A—N1A	150.21 (13)
C2B—C1B—C5B—C4B	19.31 (13)	C2A—C1A—C5A—C4A	−25.50 (15)
C3B—C4B—C5B—N1B	−178.62 (13)	C3A—C4A—C5A—N1A	−173.30 (14)
C3B—C4B—C5B—C1B	3.26 (13)	C3A—C4A—C5A—C1A	2.06 (15)
N1B—N2B—C6B—O1B	−176.11 (11)	N1A—N2A—C6A—O1A	−175.88 (12)
N1B—N2B—C6B—N3B	3.25 (18)	N1A—N2A—C6A—N3A	3.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1N2···O1B	0.875 (17)	2.048 (17)	2.9088 (14)	167.7 (17)
N3A—H1N3···N1Bi	0.858 (18)	2.614 (18)	3.3214 (16)	140.5 (16)
N3A—H2N3···O1Aii	0.926 (19)	1.949 (19)	2.8749 (16)	178.7 (15)
N2B—H2N2···O1A	0.919 (17)	2.065 (17)	2.9663 (14)	166.6 (16)
N3B—H3N3···O1Biii	0.889 (19)	1.980 (19)	2.8682 (16)	175.9 (18)
N3B—H4N3···N1Aiv	0.858 (17)	2.515 (17)	3.1771 (16)	134.7 (15)
C1A—H1AB···O1Bv	0.99	2.52	3.3923 (18)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1N2⋯O1B	0.875 (17)	2.048 (17)	2.9088 (14)	167.7 (17)
N3A—H1N3⋯N1B i	0.858 (18)	2.614 (18)	3.3214 (16)	140.5 (16)
N3A—H2N3⋯O1A ii	0.926 (19)	1.949 (19)	2.8749 (16)	178.7 (15)
N2B—H2N2⋯O1A	0.919 (17)	2.065 (17)	2.9663 (14)	166.6 (16)
N3B—H3N3⋯O1B iii	0.889 (19)	1.980 (19)	2.8682 (16)	175.9 (18)
N3B—H4N3⋯N1A iv	0.858 (17)	2.515 (17)	3.1771 (16)	134.7 (15)
C1A—H1AB⋯O1B v	0.99	2.52	3.3923 (18)	146

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