Methyl 3-(2-furyl-methyl-idene)carbazate.

The asymmetric unit of the title compound, C(7)H(8)N(2)O(3), contains two approximately planar mol-ecules (r.m.s. deviations = 0.058 and 0.070 Å). In the crystal, mol-ecules are linked into [010] chains by way of alternating N-H⋯O and N-H⋯(N,O) hydrogen-bond linkages.

Related literature

For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C7H8N2O3

M = 168.15

Monoclinic,

a = 14.668 (5) Å

b = 7.7356 (15) Å

c = 14.720 (3) Å

β = 104.11 (4)°

V = 1619.8 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.25 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

7823 measured reflections

3695 independent reflections

2600 reflections with I > 2σ(I)

R int = 0.117

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.186

S = 0.89

3695 reflections

217 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051019/hb5763sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051019/hb5763Isup2.hkl

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

C7H8N2O3	F(000) = 704
Mr = 168.15	Dx = 1.379 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 14.668 (5) Å	Cell parameters from 3695 reflections
b = 7.7356 (15) Å	θ = 3.2–27.5°
c = 14.720 (3) Å	µ = 0.11 mm−1
β = 104.11 (4)°	T = 293 K
V = 1619.8 (7) Å3	Block, colorless
Z = 8	0.25 × 0.22 × 0.18 mm

Bruker SMART CCD diffractometer	2600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.117
graphite	θmax = 27.5°, θmin = 3.2°
phi and ω scans	h = −16→18
7823 measured reflections	k = −9→10
3695 independent reflections	l = −19→19

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 0.89	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3695 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

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
O5	0.18498 (16)	0.9708 (3)	0.08083 (14)	0.0286 (5)
N4	0.22925 (19)	0.8558 (3)	0.25908 (17)	0.0242 (5)
N3	0.1797 (2)	0.7585 (3)	0.18594 (17)	0.0281 (6)
H3A	0.1595	0.6572	0.1951	0.034*
O4	0.33569 (18)	1.0262 (3)	0.41175 (15)	0.0358 (6)
O6	0.1200 (2)	0.7115 (3)	0.03597 (15)	0.0397 (7)
C8	0.2972 (2)	0.8690 (4)	0.4211 (2)	0.0276 (7)
C12	0.2438 (2)	0.7836 (4)	0.3391 (2)	0.0260 (7)
H12A	0.2194	0.6741	0.3443	0.031*
C13	0.1635 (2)	0.8259 (4)	0.0994 (2)	0.0261 (7)
C9	0.3199 (3)	0.8194 (5)	0.5124 (2)	0.0376 (9)
H9A	0.3020	0.7180	0.5371	0.045*
C14	0.0973 (4)	0.7748 (5)	−0.0591 (2)	0.0489 (11)
H14A	0.0666	0.6853	−0.1005	0.073*
H14B	0.1539	0.8086	−0.0759	0.073*
H14C	0.0562	0.8728	−0.0640	0.073*
C11	0.3764 (3)	0.9529 (6)	0.5622 (2)	0.0419 (9)
H11A	0.4032	0.9564	0.6263	0.050*
C10	0.3839 (3)	1.0730 (6)	0.4994 (2)	0.0421 (9)
H10A	0.4176	1.1754	0.5137	0.051*
O2	0.04032 (17)	0.4665 (3)	0.19917 (14)	0.0296 (5)
N1	0.1456 (2)	0.2564 (4)	0.18947 (19)	0.0291 (6)
H1A	0.1539	0.1531	0.1715	0.035*
N2	0.22041 (19)	0.3544 (3)	0.23547 (17)	0.0265 (6)
C6	0.0590 (2)	0.3252 (4)	0.1731 (2)	0.0272 (7)
O3	−0.00370 (18)	0.2153 (3)	0.12255 (17)	0.0371 (6)
C5	0.3004 (2)	0.2814 (4)	0.2473 (2)	0.0264 (7)
H5A	0.3037	0.1687	0.2264	0.032*
O1	0.37821 (19)	0.5284 (3)	0.3290 (2)	0.0509 (8)
C1	0.3852 (2)	0.3697 (4)	0.2920 (2)	0.0282 (7)
C2	0.4759 (3)	0.3280 (5)	0.3040 (2)	0.0348 (8)
H2B	0.4995	0.2257	0.2857	0.042*
C7	−0.0995 (3)	0.2726 (6)	0.0996 (3)	0.0501 (10)
H7A	−0.1386	0.1857	0.0629	0.075*
H7B	−0.1046	0.3780	0.0644	0.075*
H7C	−0.1194	0.2924	0.1562	0.075*
C4	0.5291 (3)	0.4693 (6)	0.3499 (3)	0.0463 (10)
H4B	0.5943	0.4781	0.3669	0.056*
C3	0.4682 (3)	0.5862 (6)	0.3638 (3)	0.0587 (13)
H3B	0.4842	0.6924	0.3929	0.070*

	U11	U22	U33	U12	U13	U23
O5	0.0362 (13)	0.0239 (12)	0.0235 (10)	−0.0029 (10)	0.0033 (9)	−0.0002 (8)
N4	0.0261 (13)	0.0244 (14)	0.0213 (12)	0.0009 (11)	0.0044 (9)	−0.0031 (10)
N3	0.0392 (16)	0.0191 (12)	0.0258 (13)	−0.0054 (11)	0.0074 (11)	−0.0036 (10)
O4	0.0394 (15)	0.0431 (15)	0.0218 (11)	−0.0052 (11)	0.0018 (10)	0.0004 (9)
O6	0.0650 (19)	0.0328 (14)	0.0197 (11)	−0.0137 (12)	0.0070 (11)	−0.0089 (9)
C8	0.0252 (17)	0.033 (2)	0.0244 (15)	0.0089 (13)	0.0056 (12)	0.0049 (12)
C12	0.0236 (15)	0.0287 (17)	0.0274 (15)	0.0047 (12)	0.0093 (12)	0.0010 (12)
C13	0.0276 (16)	0.0272 (17)	0.0249 (15)	−0.0004 (13)	0.0090 (12)	−0.0056 (12)
C9	0.040 (2)	0.049 (2)	0.0234 (16)	0.0136 (17)	0.0078 (14)	0.0077 (14)
C14	0.078 (3)	0.046 (2)	0.0189 (16)	−0.018 (2)	0.0044 (17)	−0.0067 (15)
C11	0.038 (2)	0.064 (3)	0.0198 (15)	0.0132 (18)	0.0010 (14)	−0.0020 (16)
C10	0.044 (2)	0.052 (2)	0.0260 (17)	−0.0013 (18)	0.0013 (15)	−0.0107 (16)
O2	0.0335 (12)	0.0265 (12)	0.0247 (11)	0.0025 (10)	−0.0006 (9)	−0.0045 (9)
N1	0.0292 (15)	0.0200 (13)	0.0360 (14)	−0.0038 (11)	0.0039 (11)	−0.0066 (10)
N2	0.0294 (15)	0.0209 (13)	0.0273 (13)	−0.0028 (11)	0.0035 (10)	−0.0039 (10)
C6	0.0319 (18)	0.0264 (16)	0.0206 (14)	−0.0028 (13)	0.0015 (12)	−0.0025 (12)
O3	0.0319 (14)	0.0315 (14)	0.0434 (14)	−0.0036 (10)	0.0006 (11)	−0.0118 (10)
C5	0.0294 (17)	0.0275 (16)	0.0223 (14)	0.0021 (12)	0.0062 (12)	−0.0001 (11)
O1	0.0242 (14)	0.0374 (15)	0.088 (2)	−0.0019 (11)	0.0086 (13)	−0.0304 (14)
C1	0.0311 (18)	0.0256 (17)	0.0284 (16)	0.0014 (13)	0.0082 (13)	−0.0049 (12)
C2	0.0346 (19)	0.0350 (18)	0.0327 (17)	0.0130 (15)	0.0043 (14)	−0.0072 (14)
C7	0.033 (2)	0.051 (2)	0.058 (2)	−0.0012 (18)	−0.0055 (17)	−0.016 (2)
C4	0.0242 (19)	0.055 (2)	0.055 (2)	0.0022 (17)	0.0021 (16)	−0.023 (2)
C3	0.025 (2)	0.054 (3)	0.093 (3)	−0.0031 (18)	0.006 (2)	−0.035 (2)

O5—C13	1.214 (4)	O2—C6	1.211 (4)
N4—C12	1.273 (4)	N1—C6	1.344 (4)
N4—N3	1.368 (3)	N1—N2	1.369 (4)
N3—C13	1.343 (4)	N1—H1A	0.8600
N3—H3A	0.8600	N2—C5	1.275 (4)
O4—C10	1.360 (4)	C6—O3	1.338 (4)
O4—C8	1.361 (4)	O3—C7	1.432 (5)
O6—C13	1.331 (4)	C5—C1	1.431 (4)
O6—C14	1.442 (4)	C5—H5A	0.9300
C8—C9	1.359 (4)	O1—C1	1.357 (4)
C8—C12	1.430 (4)	O1—C3	1.370 (5)
C12—H12A	0.9300	C1—C2	1.339 (5)
C9—C11	1.412 (6)	C2—C4	1.414 (6)
C9—H9A	0.9300	C2—H2B	0.9300
C14—H14A	0.9600	C7—H7A	0.9600
C14—H14B	0.9600	C7—H7B	0.9600
C14—H14C	0.9600	C7—H7C	0.9600
C11—C10	1.334 (6)	C4—C3	1.321 (6)
C11—H11A	0.9300	C4—H4B	0.9300
C10—H10A	0.9300	C3—H3B	0.9300
C12—N4—N3	115.1 (3)	C6—N1—N2	118.5 (3)
C13—N3—N4	118.1 (3)	C6—N1—H1A	120.7
C13—N3—H3A	121.0	N2—N1—H1A	120.7
N4—N3—H3A	121.0	C5—N2—N1	115.0 (3)
C10—O4—C8	105.9 (3)	O2—C6—O3	124.8 (3)
C13—O6—C14	114.4 (3)	O2—C6—N1	125.3 (3)
C9—C8—O4	110.1 (3)	O3—C6—N1	109.9 (3)
C9—C8—C12	131.0 (3)	C6—O3—C7	115.9 (3)
O4—C8—C12	118.9 (3)	N2—C5—C1	121.2 (3)
N4—C12—C8	120.8 (3)	N2—C5—H5A	119.4
N4—C12—H12A	119.6	C1—C5—H5A	119.4
C8—C12—H12A	119.6	C1—O1—C3	106.6 (3)
O5—C13—O6	124.2 (3)	C2—C1—O1	109.6 (3)
O5—C13—N3	125.2 (3)	C2—C1—C5	132.1 (3)
O6—C13—N3	110.6 (3)	O1—C1—C5	118.4 (3)
C8—C9—C11	106.2 (3)	C1—C2—C4	106.9 (3)
C8—C9—H9A	126.9	C1—C2—H2B	126.5
C11—C9—H9A	126.9	C4—C2—H2B	126.5
O6—C14—H14A	109.5	O3—C7—H7A	109.5
O6—C14—H14B	109.5	O3—C7—H7B	109.5
H14A—C14—H14B	109.5	H7A—C7—H7B	109.5
O6—C14—H14C	109.5	O3—C7—H7C	109.5
H14A—C14—H14C	109.5	H7A—C7—H7C	109.5
H14B—C14—H14C	109.5	H7B—C7—H7C	109.5
C10—C11—C9	106.6 (3)	C3—C4—C2	106.8 (3)
C10—C11—H11A	126.7	C3—C4—H4B	126.6
C9—C11—H11A	126.7	C2—C4—H4B	126.6
C11—C10—O4	111.1 (4)	C4—C3—O1	110.2 (4)
C11—C10—H10A	124.4	C4—C3—H3B	124.9
O4—C10—H10A	124.4	O1—C3—H3B	124.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.86	2.07	2.867 (4)	155
N3—H3A···O2	0.86	2.30	3.085 (4)	152
N3—H3A···N2	0.86	2.53	3.232 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.86	2.07	2.867 (4)	155
N3—H3A⋯O2	0.86	2.30	3.085 (4)	152
N3—H3A⋯N2	0.86	2.53	3.232 (3)	140

Symmetry code: (i) .