6-Nitro-1,3-benzodioxole-4-carbaldehyde

The title compound, C₈H₅NO₅, consists of a cyclic diether (1,3-dioxalene) fused to 3-nitro­benzaldehyde. In the crystal structure, symmetry-related mol­ecules are linked by C—H...O hydrogen bonds, forming a sheet-like structure parallel to the ab plane. These sheets are further linked by C—H...O hydrogen bonds, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.118
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.110
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O5     ..  C7      ..       2.99 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

6-Nitro-1,3-benzodioxole-4-carbaldehyde

Crystal data

C8H5NO5	F(000) = 400
Mr = 195.13	Dx = 1.696 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5272 reflections
a = 7.462 (1) Å	θ = 2.6–29.6°
b = 14.166 (2) Å	µ = 0.15 mm^−1
c = 7.3202 (10) Å	T = 173 K
β = 98.975 (11)°	Plate, yellow
V = 764.3 (2) Å^3	0.40 × 0.40 × 0.15 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	1502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.110
Graphite monochromator	θmax = 29.3°, θmin = 2.8°
Detector resolution: 6.67 pixels mm^-1	h = −10→9
φ and ω scans	k = −19→19
7266 measured reflections	l = −10→9
2013 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0518P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2013 reflections	Δρmax = 0.38 e Å^−3
148 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (5)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.74307 (17)	1.05449 (8)	0.12610 (18)	0.0408 (4)
O2	0.70215 (14)	0.65053 (7)	0.27721 (14)	0.0269 (3)
O3	0.87287 (14)	0.76767 (7)	0.16668 (14)	0.0264 (3)
O4	0.1829 (2)	0.95479 (9)	0.3843 (2)	0.0484 (4)
O5	0.16909 (16)	0.81293 (9)	0.48801 (17)	0.0404 (4)
N1	0.24299 (18)	0.87460 (9)	0.40923 (18)	0.0307 (4)
C1	0.67432 (19)	0.90000 (9)	0.21585 (18)	0.0231 (4)
C2	0.5105 (2)	0.92180 (9)	0.27806 (19)	0.0247 (4)
C3	0.41175 (19)	0.85088 (9)	0.34309 (18)	0.0238 (4)
C4	0.4629 (2)	0.75554 (9)	0.35097 (18)	0.0231 (4)
C5	0.62143 (19)	0.73630 (9)	0.29023 (18)	0.0216 (4)
C6	0.72612 (18)	0.80620 (9)	0.22424 (17)	0.0212 (3)
C7	0.8735 (2)	0.66945 (10)	0.2188 (2)	0.0283 (4)
C8	0.7846 (2)	0.97229 (10)	0.1421 (2)	0.0284 (4)
H2	0.466 (3)	0.9874 (14)	0.276 (3)	0.036 (5)*
H4	0.387 (3)	0.7099 (13)	0.396 (3)	0.034 (5)*
H7A	0.976 (3)	0.6597 (13)	0.325 (3)	0.035 (5)*
H7B	0.883 (3)	0.6311 (14)	0.106 (3)	0.040 (5)*
H8	0.892 (3)	0.9531 (15)	0.092 (3)	0.042 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0411 (7)	0.0197 (5)	0.0607 (8)	−0.0024 (4)	0.0048 (6)	0.0064 (5)
O2	0.0266 (6)	0.0173 (4)	0.0390 (5)	0.0031 (4)	0.0122 (4)	0.0013 (4)
O3	0.0245 (6)	0.0199 (5)	0.0368 (5)	0.0024 (4)	0.0114 (4)	0.0030 (4)
O4	0.0396 (7)	0.0339 (6)	0.0753 (9)	0.0142 (5)	0.0207 (7)	0.0026 (6)
O5	0.0324 (7)	0.0393 (6)	0.0538 (7)	−0.0015 (5)	0.0205 (6)	−0.0010 (5)
N1	0.0252 (7)	0.0287 (6)	0.0390 (7)	0.0029 (5)	0.0080 (6)	−0.0050 (5)
C1	0.0227 (7)	0.0184 (6)	0.0274 (6)	−0.0007 (5)	0.0019 (5)	−0.0002 (4)
C2	0.0261 (7)	0.0190 (6)	0.0281 (6)	0.0025 (5)	0.0011 (5)	−0.0028 (5)
C3	0.0200 (7)	0.0244 (6)	0.0272 (6)	0.0018 (5)	0.0047 (5)	−0.0021 (5)
C4	0.0234 (7)	0.0212 (6)	0.0249 (6)	−0.0019 (5)	0.0049 (5)	−0.0003 (5)
C5	0.0236 (7)	0.0159 (6)	0.0254 (6)	0.0007 (5)	0.0039 (5)	−0.0003 (4)
C6	0.0189 (6)	0.0217 (6)	0.0230 (6)	0.0004 (4)	0.0034 (5)	−0.0014 (4)
C7	0.0276 (8)	0.0203 (6)	0.0394 (8)	0.0038 (5)	0.0125 (6)	0.0044 (5)
C8	0.0293 (8)	0.0215 (6)	0.0335 (7)	−0.0048 (5)	0.0023 (6)	0.0009 (5)

Geometric parameters (Å, º)

O1—C8	1.2060 (18)	C1—C8	1.468 (2)
O2—C5	1.3660 (17)	C2—C3	1.3742 (19)
O2—C7	1.4353 (18)	C3—C4	1.4022 (18)
O3—C6	1.3485 (17)	C4—C5	1.355 (2)
O3—C7	1.4426 (17)	C5—C6	1.3935 (19)
O4—N1	1.2244 (18)	C2—H2	0.99 (2)
O5—N1	1.2244 (18)	C4—H4	0.95 (2)
N1—C3	1.457 (2)	C7—H7A	1.01 (2)
C1—C2	1.404 (2)	C7—H7B	1.00 (2)
C1—C6	1.3825 (18)	C8—H8	0.97 (2)
O1···C4^i	3.2531 (18)	C1···O2^vii	3.3277 (17)
O1···C7^ii	3.334 (2)	C2···O1^iii	3.271 (2)
O1···C2^iii	3.271 (2)	C4···O5^vii	3.3150 (19)
O2···O4^iv	3.1841 (17)	C4···O1^iv	3.2531 (18)
O2···C1^v	3.3277 (17)	C4···C5^v	3.2504 (19)
O2···C6^v	3.3066 (17)	C4···C6^v	3.2271 (19)
O2···O3	2.3136 (15)	C5···C4^vii	3.2504 (19)
O2···O3^v	3.1561 (15)	C5···O3^v	3.0829 (17)
O2···C8^v	3.1666 (18)	C5···C6^v	3.2081 (18)
O3···O5^vi	3.0344 (17)	C6···O3^v	3.4172 (17)
O3···C5^vii	3.0829 (17)	C6···O2^vii	3.3066 (17)
O3···O5^viii	2.9668 (17)	C6···C4^vii	3.2271 (19)
O3···O2	2.3136 (15)	C6···C5^vii	3.2081 (18)
O3···C6^vii	3.4172 (17)	C7···O1^xi	3.334 (2)
O3···O2^vii	3.1561 (15)	C7···O4^iv	3.146 (2)
O3···C7^vii	3.3981 (18)	C7···O5^vi	3.395 (2)
O4···O2^i	3.1841 (17)	C7···O5^viii	2.991 (2)
O4···C8^ix	3.224 (2)	C7···O3^v	3.3981 (18)
O4···C7^i	3.146 (2)	C8···O2^vii	3.1666 (18)
O5···C7^ix	3.395 (2)	C8···O4^vi	3.224 (2)
O5···O3^ix	3.0344 (17)	C1···H7B^v	3.06 (2)
O5···C4^v	3.3150 (19)	C6···H7B^v	2.99 (2)
O5···C7^x	2.991 (2)	H2···O1	2.66 (2)
O5···O3^x	2.9668 (17)	H2···O4	2.41 (2)
O1···H2	2.66 (2)	H2···O2^i	2.63 (2)
O1···H7A^ii	2.55 (2)	H4···O5	2.36 (2)
O1···H4^i	2.401 (19)	H4···O1^iv	2.401 (19)
O2···H2^iv	2.63 (2)	H7A···O5^vi	2.77 (2)
O2···H8^v	2.91 (2)	H7A···O1^xi	2.55 (2)
O3···H7A^vii	2.92 (2)	H7A···O3^v	2.92 (2)
O3···H8	2.69 (2)	H7B···O4^iv	2.55 (2)
O4···H8^ix	2.80 (2)	H7B···O5^viii	2.55 (2)
O4···H7B^i	2.55 (2)	H7B···C1^vii	3.06 (2)
O4···H2	2.41 (2)	H7B···C6^vii	2.99 (2)
O5···H4	2.36 (2)	H8···O3	2.69 (2)
O5···H7A^ix	2.77 (2)	H8···O4^vi	2.80 (2)
O5···H7B^x	2.55 (2)	H8···O2^vii	2.91 (2)
C5—O2—C7	106.12 (11)	O3—C6—C1	127.60 (12)
C6—O3—C7	106.08 (11)	O3—C6—C5	110.31 (11)
O4—N1—O5	123.42 (14)	C1—C6—C5	122.03 (13)
O4—N1—C3	118.67 (13)	O2—C7—O3	107.01 (11)
O5—N1—C3	117.91 (12)	O1—C8—C1	123.98 (14)
C2—C1—C6	116.65 (12)	C1—C2—H2	120.7 (13)
C2—C1—C8	122.15 (12)	C3—C2—H2	119.8 (13)
C6—C1—C8	121.19 (13)	C3—C4—H4	119.7 (13)
C1—C2—C3	119.52 (12)	C5—C4—H4	125.1 (13)
N1—C3—C2	118.97 (12)	O2—C7—H7A	110.3 (12)
N1—C3—C4	116.89 (12)	O2—C7—H7B	109.0 (13)
C2—C3—C4	124.14 (13)	O3—C7—H7A	107.8 (11)
C3—C4—C5	115.23 (12)	O3—C7—H7B	107.7 (12)
O2—C5—C4	128.24 (12)	H7A—C7—H7B	114.7 (17)
O2—C5—C6	109.31 (12)	O1—C8—H8	116.7 (13)
C4—C5—C6	122.43 (12)	C1—C8—H8	119.1 (13)
C7—O2—C5—C4	−175.63 (14)	C8—C1—C6—O3	−1.6 (2)
C7—O2—C5—C6	6.14 (14)	C8—C1—C6—C5	−178.66 (13)
C5—O2—C7—O3	−10.25 (14)	C2—C1—C8—O1	−1.3 (2)
C7—O3—C6—C1	175.65 (13)	C6—C1—C8—O1	177.54 (14)
C7—O3—C6—C5	−7.00 (14)	C1—C2—C3—N1	179.31 (12)
C6—O3—C7—O2	10.61 (14)	C1—C2—C3—C4	−0.5 (2)
O4—N1—C3—C2	8.8 (2)	N1—C3—C4—C5	−179.31 (12)
O4—N1—C3—C4	−171.40 (14)	C2—C3—C4—C5	0.5 (2)
O5—N1—C3—C2	−170.89 (13)	C3—C4—C5—O2	−178.15 (13)
O5—N1—C3—C4	8.95 (19)	C3—C4—C5—C6	−0.13 (19)
C6—C1—C2—C3	0.1 (2)	O2—C5—C6—O3	0.58 (15)
C8—C1—C2—C3	179.02 (13)	O2—C5—C6—C1	178.10 (12)
C2—C1—C6—O3	177.32 (13)	C4—C5—C6—O3	−177.77 (12)
C2—C1—C6—C5	0.25 (19)	C4—C5—C6—C1	−0.3 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^iv	0.95 (2)	2.401 (19)	3.2531 (18)	148.8 (17)
C7—H7A···O1^xi	1.01 (2)	2.55 (2)	3.334 (2)	133.9 (15)
C7—H7B···O4^iv	1.00 (2)	2.55 (2)	3.146 (2)	118.1 (15)
C7—H7B···O5^viii	1.00 (2)	2.55 (2)	2.991 (2)	106.4 (14)

Symmetry codes: (iv) −x+1, y−1/2, −z+1/2; (viii) x+1, −y+3/2, z−1/2; (xi) −x+2, y−1/2, −z+1/2.