5-Nitro-2-furaldehyde N-(hydroxy­methyl)semicarbazone

The title compound, C₇H₈N₄O₅, which is a potential anti-Chagas' derivative, was synthesized using a simple hydroxy­methyl­ation method in a basic medium with formaldehyde. The structure reveals two infinite two-dimensional networks in the (02) and (001) planes, stabilized by inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.039
• wR factor = 0.111
• Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        O22

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.25
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      21.60 Deg.
              O12  -N1   -O11     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.80 Deg.
              O21  -N1   -O22     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

5-nitro-2-furaldehyde N-(hydroxymethyl)semicarbazone

Crystal data

C7H8N4O5	F(000) = 944
Mr = 228.17	Dx = 1.596 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 16323 reflections
a = 10.3757 (5) Å	θ = 2.9–27.5°
b = 10.8125 (5) Å	µ = 0.14 mm^−1
c = 16.9455 (8) Å	T = 298 K
β = 92.095 (3)°	Needle, yellow
V = 1899.8 (2) Å^3	0.2 × 0.1 × 0.1 mm
Z = 8

Data collection

Nonius KappaCCD area-detector diffractometer	1367 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Horizonally mounted graphite crystal monochromator	θmax = 25.5°, θmin = 3.6°
Detector resolution: 9 pixels mm^-1	h = −12→12
φ scans, and ω scans with κ offsets	k = −13→13
13352 measured reflections	l = −20→20
1755 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0609P)^2 + 0.6344P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.039	(Δ/σ)max < 0.001
wR(F^2) = 0.111	Δρmax = 0.18 e Å^−3
S = 1.07	Δρmin = −0.17 e Å^−3
1755 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
170 parameters	Extinction coefficient: 0.013 (2)
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.85510 (17)	0.46319 (18)	0.30115 (10)	0.0687 (5)
N2	0.41500 (12)	0.53080 (12)	0.08495 (8)	0.0481 (4)
N3	0.32951 (13)	0.60726 (13)	0.04746 (9)	0.0537 (4)
H3	0.3337	0.6859	0.0545	0.064*
N4	0.24375 (13)	0.43515 (12)	−0.01394 (9)	0.0502 (4)
H4	0.3056	0.3951	0.0096	0.06*
O3	0.68403 (11)	0.53924 (11)	0.21938 (7)	0.0522 (4)
O4	0.15337 (11)	0.62518 (10)	−0.03360 (8)	0.0551 (4)
O5	0.07951 (12)	0.28440 (11)	−0.02165 (8)	0.0587 (4)
O11	0.8972 (16)	0.369 (2)	0.3360 (11)	0.080 (3)	0.5
O12	0.9298 (17)	0.377 (2)	0.3184 (12)	0.087 (3)	0.5
O21	0.8728 (19)	0.5650 (15)	0.3258 (9)	0.073 (2)	0.5
O22	0.896 (2)	0.5726 (18)	0.3076 (10)	0.110 (5)	0.5
C1	0.75064 (17)	0.43960 (17)	0.24722 (10)	0.0535 (5)
C2	0.70584 (19)	0.33386 (18)	0.21729 (11)	0.0634 (5)
H2	0.7369	0.2547	0.2279	0.076*
C3	0.60162 (19)	0.36677 (17)	0.16629 (11)	0.0597 (5)
H3A	0.5499	0.3129	0.1364	0.072*
C4	0.59064 (15)	0.49087 (16)	0.16884 (9)	0.0469 (4)
C5	0.50308 (15)	0.57706 (15)	0.13029 (10)	0.0490 (4)
H5	0.5105	0.6619	0.1381	0.059*
C6	0.23621 (14)	0.55693 (15)	−0.00192 (10)	0.0450 (4)
C7	0.15416 (17)	0.36740 (16)	−0.06393 (11)	0.0530 (5)
H7A	0.0975	0.4252	−0.0919	0.064*
H7B	0.2015	0.322	−0.1029	0.064*
H5A	0.012 (2)	0.325 (2)	−0.0022 (13)	0.093 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0683 (11)	0.0636 (12)	0.0719 (11)	0.0045 (9)	−0.0305 (9)	0.0033 (9)
N2	0.0424 (7)	0.0422 (8)	0.0587 (8)	0.0012 (6)	−0.0109 (6)	0.0039 (6)
N3	0.0464 (8)	0.0372 (7)	0.0759 (10)	0.0016 (6)	−0.0196 (7)	0.0003 (6)
N4	0.0420 (7)	0.0384 (8)	0.0690 (9)	−0.0002 (6)	−0.0145 (6)	0.0042 (6)
O3	0.0506 (7)	0.0455 (7)	0.0591 (7)	−0.0005 (5)	−0.0171 (5)	0.0027 (5)
O4	0.0425 (6)	0.0447 (7)	0.0770 (8)	0.0053 (5)	−0.0155 (6)	0.0044 (6)
O5	0.0472 (7)	0.0388 (7)	0.0898 (10)	−0.0025 (5)	−0.0033 (6)	−0.0002 (6)
O11	0.087 (8)	0.069 (3)	0.082 (6)	0.015 (5)	−0.037 (5)	0.016 (4)
O12	0.076 (6)	0.082 (4)	0.101 (9)	0.014 (4)	−0.035 (4)	0.015 (5)
O21	0.080 (5)	0.054 (4)	0.084 (3)	−0.008 (3)	−0.038 (3)	−0.001 (2)
O22	0.094 (8)	0.076 (4)	0.155 (12)	−0.012 (4)	−0.074 (8)	0.007 (7)
C1	0.0533 (9)	0.0517 (10)	0.0543 (9)	0.0050 (7)	−0.0137 (8)	0.0051 (8)
C2	0.0712 (12)	0.0465 (10)	0.0710 (12)	0.0061 (9)	−0.0197 (10)	0.0021 (9)
C3	0.0633 (11)	0.0472 (10)	0.0671 (11)	−0.0020 (8)	−0.0194 (9)	−0.0007 (8)
C4	0.0430 (9)	0.0503 (10)	0.0468 (9)	−0.0041 (7)	−0.0080 (7)	0.0013 (7)
C5	0.0448 (9)	0.0431 (9)	0.0582 (10)	−0.0023 (7)	−0.0101 (8)	0.0010 (7)
C6	0.0361 (8)	0.0402 (9)	0.0581 (9)	−0.0001 (6)	−0.0053 (7)	0.0050 (7)
C7	0.0514 (10)	0.0451 (9)	0.0617 (10)	−0.0046 (7)	−0.0107 (8)	−0.0010 (7)

Geometric parameters (Å, º)

N1—O21	1.190 (17)	O3—C4	1.373 (2)
N1—O12	1.24 (2)	O4—C6	1.240 (2)
N1—O11	1.24 (2)	O5—C7	1.400 (2)
N1—O22	1.259 (19)	O5—H5A	0.90 (3)
N1—C1	1.415 (2)	C1—C2	1.328 (3)
N2—C5	1.274 (2)	C2—C3	1.405 (2)
N2—N3	1.354 (2)	C2—H2	0.93
N3—C6	1.369 (2)	C3—C4	1.347 (2)
N3—H3	0.86	C3—H3A	0.93
N4—C6	1.335 (2)	C4—C5	1.441 (2)
N4—C7	1.436 (2)	C5—H5	0.93
N4—H4	0.86	C7—H7A	0.97
O3—C1	1.355 (2)	C7—H7B	0.97
O21—N1—O12	121.6 (14)	C1—C2—C3	105.52 (17)
O21—N1—O11	122.7 (13)	C1—C2—H2	127.2
O12—N1—O11	21.6 (12)	C3—C2—H2	127.2
O21—N1—O22	18.8 (14)	C4—C3—C2	107.25 (16)
O12—N1—O22	118.7 (14)	C4—C3—H3A	126.4
O11—N1—O22	127.9 (13)	C2—C3—H3A	126.4
O21—N1—C1	119.9 (9)	C3—C4—O3	109.92 (14)
O12—N1—C1	118.4 (11)	C3—C4—C5	133.01 (16)
O11—N1—C1	114.0 (10)	O3—C4—C5	117.07 (15)
O22—N1—C1	118.1 (9)	N2—C5—C4	116.47 (15)
C5—N2—N3	119.10 (14)	N2—C5—H5	121.8
N2—N3—C6	118.73 (13)	C4—C5—H5	121.8
N2—N3—H3	120.6	O4—C6—N4	124.36 (15)
C6—N3—H3	120.6	O4—C6—N3	119.44 (15)
C6—N4—C7	123.58 (14)	N4—C6—N3	116.18 (14)
C6—N4—H4	118.2	O5—C7—N4	112.6 (1)
C7—N4—H4	118.2	O5—C7—H7A	109.1
C1—O3—C4	104.69 (13)	N4—C7—H7A	109.1
C7—O5—H5A	109 (2)	O5—C7—H7B	109.1
C2—C1—O3	112.61 (15)	N4—C7—H7B	109.1
C2—C1—N1	130.62 (17)	H7A—C7—H7B	107.8
O3—C1—N1	116.76 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O4^i	0.86	2.08	2.909 (2)	162
N4—H4···O5^ii	0.86	2.28	3.047 (2)	148
C2—H2···O21^iii	0.93	2.50	3.10 (2)	122
C2—H2···O22^iii	0.93	2.47	3.04 (2)	120
C3—H3A···O5^ii	0.93	2.55	3.446 (2)	162
C5—H5···O11^iv	0.93	2.48	3.37 (2)	162
C5—H5···O12^iv	0.93	2.51	3.42 (2)	167
O5—H5A···O4^v	0.90 (2)	1.92 (2)	2.799 (2)	166 (2)

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, −y+1/2, −z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x, −y+1, −z.