Methyl 3-(2-furyl­methyl­idene)carbazate

Li, Y.-F.

doi:10.1107/S1600536810051019

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o64

https://doi.org/10.1107/S1600536810051019

Open

access

Methyl 3-(2-furylmethylidene)carbazate

Yu-Feng Li ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 5 December 2010; accepted 6 December 2010; online 11 December 2010)

The asymmetric unit of the title compound, C₇H₈N₂O₃, contains two approximately planar molecules (r.m.s. deviations = 0.058 and 0.070 Å). In the crystal, molecules 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_r = 168.15
Monoclinic, C 2
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[F² > 2σ(F²)] = 0.072
wR(F²) = 0.186
S = 0.89
3695 reflections
217 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) x, y-1, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051019/hb5763Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

A mixture of methyl carbazate (0.1 mol), and furfural (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.085 mol, yield 85%). Colourless blocks of the title compound were obtained by recrystallization from ethanol at room temperature.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids.

Methyl 3-(2-furylmethylidene)carbazate top

Crystal data top

C₇H₈N₂O₃	F(000) = 704
M_r = 168.15	D_x = 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

Data collection top

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

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3695 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₇H₈N₂O₃	V = 1619.8 (7) Å³
M_r = 168.15	Z = 8
Monoclinic, C2	Mo Kα radiation
a = 14.668 (5) Å	µ = 0.11 mm⁻¹
b = 7.7356 (15) Å	T = 293 K
c = 14.720 (3) Å	0.25 × 0.22 × 0.18 mm
β = 104.11 (4)°

Data collection top

Bruker SMART CCD diffractometer	2600 reflections with I > 2σ(I)
7823 measured reflections	R_int = 0.117
3695 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	1 restraint
wR(F²) = 0.186	H-atom parameters constrained
S = 0.89	Δρ_max = 0.37 e Å⁻³
3695 reflections	Δρ_min = −0.28 e Å⁻³
217 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₇H₈N₂O₃
M_r	168.15
Crystal system, space group	Monoclinic, C2
Temperature (K)	293
a, b, c (Å)	14.668 (5), 7.7356 (15), 14.720 (3)
β (°)	104.11 (4)
V (Å³)	1619.8 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7823, 3695, 2600
R_int	0.117
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.186, 0.89
No. of reflections	3695
No. of parameters	217
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1720. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o64

https://doi.org/10.1107/S1600536810051019

Open

access