2-Amino-5-iodo­benzohydroxamic acid: supra­molecular aggregation through two-dimensional networks of N—H...O, O—H...N and C—H...O inter­actions

In the title compound, C₇H₇IN₂O₂, the dihedral angle between the mean planes of the benzene ring and the hydroxamic acid group is 39.12 (14)°. The mol­ecules are linked via N—H...O, O—H...N and C—H...O inter­actions, forming two-dimensional layers parallel to (100) in the crystal structure. There is an I...I inter­molecular van der Waals contact.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.091
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H9A    ..  H11     ..       2.05 Ang.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          3
PLAT420_ALERT_2_C D-H Without Acceptor       N9     -   H9B    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B    ..  I       ..       3.09 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Role played by each named author is given below. Nagarajan Vembu - Crystallization, Structure solution & refinement, Paper writing Anthony Linden - Data collection and suggestions for improving the quality of the manuscript with special reference to the H-bonding discussion in the comment section Jean Lee - Synthesis of the compound John G. Kelly, Kevin B. Nolan and Marc Devocelle - Planned and advised on synthetic methodology

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); 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.

2-amino-5-iodobenzohydroxamic acid

Crystal data

C7H7IN2O2	F(000) = 528
Mr = 278.05	Dx = 2.190 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 67557 reflections
a = 13.5332 (4) Å	θ = 2.0–30.0°
b = 4.8500 (2) Å	µ = 3.76 mm^−1
c = 13.2820 (4) Å	T = 160 K
β = 104.6614 (19)°	Prism, colourless
V = 843.39 (5) Å^3	0.18 × 0.18 × 0.08 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	2458 independent reflections
Radiation source: Nonius FR590 sealed tube generator	2084 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.057
Detector resolution: 9 pixels mm^-1	θmax = 30.0°, θmin = 3.1°
φ and ω scans	h = −19→19
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −6→6
Tmin = 0.512, Tmax = 0.773	l = −18→18
22968 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	All H-atom parameters refined
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.3155P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max = 0.001
2458 reflections	Δρmax = 2.18 e Å^−3
138 parameters	Δρmin = −1.18 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0189 (12)

Special details

Experimental. Solvent used: EtOAc / acetone Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 1.461 (2) Frames collected: 765 Seconds exposure per frame: 16 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 30.0

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.

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

	x	y	z	Uiso*/Ueq
C1	0.3334 (2)	0.6155 (6)	0.3337 (2)	0.0205 (5)
C2	0.2717 (2)	0.7521 (7)	0.3890 (2)	0.0223 (5)
C3	0.1660 (2)	0.7087 (7)	0.3591 (3)	0.0256 (6)
C4	0.1216 (2)	0.5382 (7)	0.2753 (2)	0.0255 (6)
C5	0.1838 (2)	0.4073 (7)	0.2215 (2)	0.0227 (6)
C6	0.2887 (2)	0.4446 (6)	0.2502 (2)	0.0215 (6)
C7	0.4463 (2)	0.6624 (6)	0.3619 (2)	0.0197 (6)
N8	0.50113 (18)	0.4420 (6)	0.3552 (2)	0.0237 (5)
N9	0.3137 (2)	0.9087 (6)	0.4775 (2)	0.0259 (5)
O10	0.48448 (17)	0.8926 (5)	0.38795 (19)	0.0265 (5)
O11	0.60607 (16)	0.4718 (5)	0.3671 (2)	0.0296 (5)
I	0.119249 (15)	0.16606 (5)	0.090077 (15)	0.02907 (12)
H3	0.127 (3)	0.805 (8)	0.393 (4)	0.028 (11)*
H4	0.046 (3)	0.511 (7)	0.254 (3)	0.015 (8)*
H6	0.329 (3)	0.369 (7)	0.212 (3)	0.016 (8)*
H8	0.482 (4)	0.263 (11)	0.350 (4)	0.039 (12)*
H9A	0.370 (3)	0.974 (8)	0.478 (3)	0.022 (9)*
H9B	0.273 (4)	1.031 (10)	0.492 (4)	0.043 (12)*
H11	0.629 (3)	0.349 (8)	0.422 (4)	0.034 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0192 (12)	0.0211 (14)	0.0209 (13)	−0.0013 (10)	0.0042 (10)	−0.0005 (11)
C2	0.0245 (14)	0.0223 (13)	0.0202 (13)	0.0008 (12)	0.0058 (11)	0.0001 (12)
C3	0.0221 (14)	0.0319 (17)	0.0249 (15)	0.0012 (12)	0.0099 (12)	−0.0005 (13)
C4	0.0207 (13)	0.0313 (17)	0.0249 (14)	−0.0004 (12)	0.0065 (11)	0.0004 (13)
C5	0.0229 (13)	0.0246 (13)	0.0191 (13)	−0.0033 (11)	0.0026 (10)	0.0000 (11)
C6	0.0211 (12)	0.0223 (15)	0.0224 (13)	−0.0017 (11)	0.0079 (10)	−0.0016 (11)
C7	0.0222 (14)	0.0198 (14)	0.0179 (12)	−0.0020 (10)	0.0065 (11)	0.0002 (10)
N8	0.0176 (11)	0.0222 (14)	0.0319 (13)	−0.0017 (10)	0.0074 (10)	−0.0011 (11)
N9	0.0249 (13)	0.0276 (13)	0.0257 (13)	0.0016 (12)	0.0074 (11)	−0.0062 (11)
O10	0.0250 (11)	0.0216 (10)	0.0307 (12)	−0.0037 (9)	0.0028 (9)	−0.0037 (9)
O11	0.0181 (10)	0.0316 (13)	0.0403 (13)	0.0003 (9)	0.0093 (9)	0.0080 (10)
I	0.02542 (15)	0.03572 (17)	0.02536 (15)	−0.00795 (7)	0.00510 (9)	−0.00667 (7)

Geometric parameters (Å, º)

C1—C6	1.394 (4)	C5—I	2.100 (3)
C1—C2	1.410 (4)	C6—H6	0.91 (4)
C1—C7	1.496 (4)	C7—O10	1.242 (4)
C2—N9	1.394 (4)	C7—N8	1.317 (4)
C2—C3	1.399 (4)	N8—O11	1.396 (3)
C3—C4	1.395 (5)	N8—H8	0.91 (5)
C3—H3	0.90 (5)	N9—H9A	0.82 (4)
C4—C5	1.388 (4)	N9—H9B	0.87 (5)
C4—H4	1.00 (3)	O11—H11	0.93 (4)
C5—C6	1.386 (4)
C6—C1—C2	119.9 (3)	C4—C5—I	120.3 (2)
C6—C1—C7	120.0 (3)	C5—C6—C1	120.3 (3)
C2—C1—C7	120.0 (3)	C5—C6—H6	120 (2)
N9—C2—C3	119.4 (3)	C1—C6—H6	119 (2)
N9—C2—C1	121.7 (3)	O10—C7—N8	123.2 (3)
C3—C2—C1	118.6 (3)	O10—C7—C1	122.2 (3)
C4—C3—C2	121.3 (3)	N8—C7—C1	114.6 (2)
C4—C3—H3	121 (3)	C7—N8—O11	118.9 (3)
C2—C3—H3	118 (3)	C7—N8—H8	129 (3)
C5—C4—C3	119.1 (3)	O11—N8—H8	112 (3)
C5—C4—H4	120.2 (19)	C2—N9—H9A	113 (3)
C3—C4—H4	120.7 (19)	C2—N9—H9B	114 (3)
C6—C5—C4	120.8 (3)	H9A—N9—H9B	112 (4)
C6—C5—I	118.9 (2)	N8—O11—H11	99 (3)
C6—C1—C2—N9	175.3 (3)	I—C5—C6—C1	176.6 (2)
C7—C1—C2—N9	−7.1 (5)	C2—C1—C6—C5	−0.3 (5)
C6—C1—C2—C3	0.9 (5)	C7—C1—C6—C5	−177.9 (3)
C7—C1—C2—C3	178.5 (3)	C6—C1—C7—O10	139.3 (3)
N9—C2—C3—C4	−175.6 (3)	C2—C1—C7—O10	−38.3 (4)
C1—C2—C3—C4	−1.1 (5)	C6—C1—C7—N8	−39.6 (4)
C2—C3—C4—C5	0.6 (5)	C2—C1—C7—N8	142.8 (3)
C3—C4—C5—C6	0.0 (5)	O10—C7—N8—O11	−6.9 (4)
C3—C4—C5—I	−176.7 (2)	C1—C7—N8—O11	172.0 (2)
C4—C5—C6—C1	−0.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O10^i	0.91 (5)	1.86 (5)	2.718 (4)	157 (4)
N9—H9A···O10	0.82 (4)	2.22 (4)	2.855 (4)	135 (3)
N9—H9A···O10^ii	0.82 (4)	2.39 (4)	3.018 (4)	134 (3)
N9—H9B···I^iii	0.87 (5)	3.09 (5)	3.925 (3)	163 (4)
O11—H11···N9^iv	0.93 (4)	1.85 (5)	2.777 (4)	173 (4)
C6—H6···O11^v	0.91 (4)	2.46 (4)	3.292 (4)	152 (3)

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