Retracted: 2-Fluoro-3,5-dinitro­benzamide monohydrate

The title complex, C₇H₄FN₃O₅·H₂O, contains one 2-fluoro-3,5-dinitro­benzamide mol­ecule and one water mol­ecule. In the crystal structure, O—H...O, O—H...F and N—H...O hydrogen bonds result in the formation of a supra­molecular network structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.063
• wR factor = 0.204
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    F1     -   C2      ..      13.32 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N3     -   C7      ..      11.38 su
PLAT430_ALERT_2_B Short Inter D...A Contact  O2     ..  O2      ..       2.60 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3B    ...          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  F1     ..  O2      ..       2.89 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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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S1. Comment

In the synthesis of crystal structures by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1995, 1997; Braga et al., 1998). Due to hydrogen-bonding interactions are of critical importance in biological systems, organic materials and coordination chemistry, hydrogen-bonding is currently the best tool in achieving this goal (Zaworotko, 1997; Braga & Grepioni, 2000). Supramolecular architectures are of considerable contemporary interest by virtue of their potential applications in various fields (Moulton & Zaworotko, 2001; Pan et al., 2001; Ma et al., 2001; Prior & Rosseinsky, 2001). We originally attempted to synthesize complexes featuring Pr metal chains by reaction of the praseodymium(III) ion with 3,5-dinitro-2-fluoro- benzamide ligand. Unfortunately, we obtained only the title compound, (I), and we report herein its crystal structure.

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). It contains one (C₇H₄FN₃O₅) molecule and one uncoordinated water molecule.

In the crystal structure, O—H···O, O—H···F and N—H···O hydrogen bonds (Table 1) seem to be effective in the stabilization of the structure, resulting in the formation of a supramolecular network structure.

Related literature

For general background, see: Desiraju (1995, 1997); Braga et al. (1998); Zaworotko (1997); Braga & Grepioni (2000); Moulton & Zaworotko (2001); Pan et al. (2001); Ma et al. (2001); Prior & Rosseinsky (2001). For bond-length data, see: Allen et al. (1987).

S2. Experimental

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Praseodymium (III) nitrate hexahydrate (217.5 mg, 0.5 mmol), 3,5-dinitro-2-fluorobenzamide (229.1 mg, 1 mmol) and distilled water (5 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 443 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

S3. Refinement

H1A, H1B (for OH₂) and H3A, H3B (for NH₂) were located in difference syntheses and refined isotropically [O—H = 0.85 (2) and 0.850 (17) Å, U_iso(H) = 0.097 (16) and 0.090 (14) Ų; N—H = 0.81 (3) and 0.83 (3) Å, U_iso(H) = 0.076 (12) and 0.09 (3) Ų]. The remaining H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2-Fluoro-3,5-dinitrobenzamide monohydrate

Crystal data

C7H4FN3O5·H2O	F(000) = 1008
Mr = 247.15	Dx = 1.763 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1503 reflections
a = 25.529 (2) Å	θ = 3.2–26.9°
b = 6.357 (4) Å	µ = 0.17 mm^−1
c = 12.353 (5) Å	T = 273 K
β = 111.749 (2)°	Prism, colourless
V = 1862.1 (15) Å^3	0.24 × 0.15 × 0.15 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	1816 independent reflections
Radiation source: fine-focus sealed tube	978 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 26.2°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→31
Tmin = 0.961, Tmax = 0.976	k = −7→7
5928 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.1305P)^2 + 0.002P] where P = (Fo^2 + 2Fc^2)/3
1816 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.37 e Å^−3
9 restraints	Δρmin = −0.42 e Å^−3

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.

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
F1	0.40250 (9)	0.2100 (4)	0.7293 (2)	0.0892 (8)
O1	0.63158 (10)	0.2285 (4)	0.0276 (2)	0.0700 (7)
H1A	0.6362 (14)	0.212 (7)	−0.0365 (14)	0.097 (16)*
H1B	0.6666 (3)	0.230 (6)	0.069 (2)	0.090 (14)*
O2	0.50775 (11)	0.2156 (5)	0.8601 (2)	0.0965 (11)
O3	0.29274 (10)	0.1317 (4)	0.63040 (19)	0.0760 (8)
O4	0.24203 (9)	0.3063 (4)	0.7042 (2)	0.0756 (8)
O5	0.30600 (10)	0.3717 (4)	1.1127 (2)	0.0805 (8)
O6	0.39278 (12)	0.2999 (5)	1.2189 (2)	0.0907 (9)
N1	0.28703 (11)	0.2254 (4)	0.7090 (2)	0.0583 (7)
N2	0.35445 (13)	0.3192 (4)	1.1254 (2)	0.0629 (8)
N3	0.53272 (10)	0.2546 (4)	1.0473 (2)	0.0491 (7)
H3A	0.5631 (9)	0.237 (5)	1.042 (3)	0.076 (12)*
H3B	0.5194 (19)	0.140 (4)	1.056 (5)	0.09 (3)*
C1	0.43548 (12)	0.2448 (5)	0.9348 (3)	0.0523 (8)
C2	0.39099 (13)	0.2303 (5)	0.8241 (3)	0.0498 (7)
C3	0.33520 (13)	0.2443 (5)	0.8193 (3)	0.0502 (8)
C4	0.32298 (13)	0.2750 (5)	0.9164 (3)	0.0520 (8)
H5	0.2859	0.2894	0.9113	0.062*
C5	0.36662 (13)	0.2839 (5)	1.0211 (3)	0.0511 (8)
C6	0.42304 (13)	0.2689 (5)	1.0327 (3)	0.0530 (8)
H7	0.4517	0.2752	1.1059	0.064*
C7	0.49530 (14)	0.2381 (5)	0.9437 (3)	0.0625 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0610 (14)	0.134 (2)	0.0738 (15)	0.0015 (11)	0.0260 (12)	−0.0017 (12)
O1	0.0406 (14)	0.0910 (19)	0.0716 (17)	0.0023 (12)	0.0129 (12)	0.0041 (13)
O2	0.0419 (15)	0.195 (3)	0.0562 (16)	0.0037 (15)	0.0225 (12)	0.0020 (15)
O3	0.0557 (15)	0.112 (2)	0.0562 (14)	−0.0072 (13)	0.0161 (12)	−0.0168 (13)
O4	0.0399 (14)	0.114 (2)	0.0692 (16)	0.0105 (12)	0.0152 (12)	0.0075 (13)
O5	0.0601 (17)	0.112 (2)	0.0797 (17)	0.0049 (14)	0.0375 (14)	−0.0085 (14)
O6	0.074 (2)	0.143 (3)	0.0487 (15)	0.0138 (16)	0.0154 (14)	−0.0041 (14)
N1	0.0373 (15)	0.0792 (19)	0.0563 (17)	−0.0029 (12)	0.0148 (13)	0.0075 (14)
N2	0.059 (2)	0.0713 (18)	0.0636 (18)	−0.0019 (14)	0.0295 (16)	−0.0052 (13)
N3	0.0235 (13)	0.0753 (18)	0.0417 (14)	−0.0018 (12)	0.0041 (11)	−0.0009 (11)
C1	0.0354 (17)	0.0652 (19)	0.0558 (19)	0.0002 (13)	0.0162 (15)	0.0027 (14)
C2	0.0397 (17)	0.0690 (19)	0.0432 (16)	0.0009 (13)	0.0183 (14)	−0.0011 (13)
C3	0.0437 (18)	0.0575 (18)	0.0449 (16)	−0.0004 (13)	0.0112 (14)	0.0043 (13)
C4	0.0423 (18)	0.0555 (18)	0.061 (2)	−0.0003 (13)	0.0227 (16)	0.0045 (13)
C5	0.0470 (19)	0.0602 (18)	0.0486 (17)	0.0026 (13)	0.0207 (15)	0.0002 (13)
C6	0.0425 (17)	0.065 (2)	0.0455 (17)	−0.0019 (14)	0.0097 (14)	−0.0010 (13)
C7	0.0441 (19)	0.078 (2)	0.065 (2)	0.0009 (15)	0.0199 (18)	0.0076 (16)

Geometric parameters (Å, º)

F1—C2	1.315 (4)	O1—H1B	0.850 (17)
O2—C7	1.196 (4)	N3—H3A	0.81 (3)
O3—N1	1.193 (3)	N3—H3B	0.83 (3)
O4—N1	1.240 (4)	C1—C6	1.367 (4)
O5—N2	1.233 (3)	C1—C2	1.420 (4)
O6—N2	1.212 (4)	C2—C3	1.406 (4)
N1—C3	1.464 (4)	C3—C4	1.361 (4)
N2—C5	1.450 (4)	C4—C5	1.360 (4)
N3—C7	1.287 (4)	C4—H5	0.9300
C1—C7	1.491 (4)	C5—C6	1.397 (4)
O1—H1A	0.85 (2)	C6—H7	0.9300
F1—C2—C1	120.1 (3)	C2—C1—C7	120.0 (3)
F1—C2—C3	121.7 (3)	C3—C2—C1	118.2 (3)
O2—C7—C1	122.2 (3)	C4—C3—C2	122.1 (3)
O2—C7—N3	122.1 (3)	C4—C3—N1	116.4 (3)
N3—C7—C1	115.7 (3)	C2—C3—N1	121.5 (3)
O3—N1—O4	124.0 (3)	C5—C4—C3	118.0 (3)
O3—N1—C3	119.0 (3)	C5—C4—H5	121.0
O4—N1—C3	117.0 (3)	C3—C4—H5	121.0
O5—N2—O6	124.5 (3)	C4—C5—C6	123.0 (3)
O5—N2—C5	117.6 (3)	C4—C5—N2	118.8 (3)
O6—N2—C5	117.9 (3)	C6—C5—N2	118.2 (3)
H1A—O1—H1B	95 (3)	C1—C6—C5	119.1 (3)
C7—N3—H3A	107 (3)	C1—C6—H7	120.5
C7—N3—H3B	82 (4)	C5—C6—H7	120.5
H3A—N3—H3B	110 (2)	O2—C7—H3B	128.8 (19)
C6—C1—C2	119.6 (3)	C1—C7—H3B	98.3 (15)
C6—C1—C7	120.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O4^i	0.85 (2)	2.04 (1)	2.863 (3)	162 (3)
O1—H1A···O3^ii	0.85 (2)	2.54 (2)	3.273 (4)	145 (3)
O1—H1A···F1^ii	0.85 (2)	2.21 (2)	2.966 (4)	147 (3)
N3—H3A···O1^iii	0.81 (3)	1.82 (2)	2.629 (3)	174 (3)

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