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For the two mol­ecules in the asymmetric unit of the title compound, C8H9NO3, the dihedral angles between the mean planes of the benzene ring and the hydroxamic acid group are 4.50 (16) and 10.10 (11)°. The supra­molecular aggregation is effected by the formation of two-dimensional networks of N—H...O and O—H...O inter­actions in addition to C—H...O and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041614/ob2079sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041614/ob2079Isup2.hkl
Contains datablock I

CCDC reference: 628032

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.060
  • wR factor = 0.156
  • Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H10 .. H22 .. 2.02 Ang.
Alert level C PLAT353_ALERT_3_C Long N-H Bond (0.87A) N20 - H20 ... 1.05 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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 1 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 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

Computing details top

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-methoxybenzohydroxamic acid top
Crystal data top
C8H9NO3F(000) = 704
Mr = 167.16Dx = 1.410 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3187 reflections
a = 11.1348 (4) Åθ = 2.0–26.0°
b = 16.7669 (6) ŵ = 0.11 mm1
c = 8.8110 (3) ÅT = 160 K
β = 106.761 (2)°Prism, orange
V = 1575.09 (10) Å30.25 × 0.20 × 0.15 mm
Z = 8
Data collection top
Nonius KappaCCD area-detector
diffractometer
2461 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed-tube generatorRint = 0.055
Horizontally mounted graphite crystal monochromatorθmax = 26.0°, θmin = 2.4°
Detector resolution: 9 pixels mm-1h = 1313
φ and ω scansk = 200
22727 measured reflectionsl = 010
3093 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060All H-atom parameters refined
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.0749P)2 + 0.4768P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max = 0.001
3092 reflectionsΔρmax = 0.52 e Å3
290 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.116 (9)
Special details top

Experimental. Solvent used: MeOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 1.232 (2) Frames collected: 436 Seconds exposure per frame: 95 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 (Å2) top
xyzUiso*/Ueq
C10.46877 (17)0.67641 (11)0.0589 (2)0.0328 (5)
C20.52475 (18)0.74741 (11)0.0887 (2)0.0357 (5)
C30.6290 (2)0.74394 (15)0.1456 (3)0.0471 (6)
C40.6764 (2)0.67180 (16)0.1742 (3)0.0529 (6)
C50.6213 (2)0.60167 (15)0.1493 (3)0.0493 (6)
C60.5179 (2)0.60461 (13)0.0919 (2)0.0409 (5)
C70.36093 (18)0.67076 (11)0.0098 (2)0.0334 (5)
N80.31835 (16)0.73676 (11)0.0562 (2)0.0407 (5)
O90.31837 (15)0.60465 (8)0.0319 (2)0.0498 (5)
O100.21762 (15)0.73401 (10)0.1197 (2)0.0499 (5)
O110.47187 (14)0.81691 (8)0.06089 (19)0.0446 (4)
C120.5254 (3)0.89086 (15)0.0897 (4)0.0529 (6)
H30.664 (3)0.7882 (16)0.160 (3)0.054 (7)*
H40.751 (3)0.6713 (16)0.214 (3)0.069 (8)*
H50.654 (2)0.5536 (15)0.172 (3)0.057 (7)*
H60.476 (2)0.5547 (13)0.072 (3)0.044 (6)*
H80.332 (2)0.7856 (17)0.027 (3)0.058 (7)*
H100.221 (3)0.6870 (19)0.182 (4)0.078 (9)*
H12A0.523 (3)0.8932 (16)0.197 (4)0.066 (8)*
H12B0.608 (3)0.8954 (15)0.014 (3)0.054 (7)*
H12C0.471 (3)0.9292 (16)0.068 (3)0.059 (7)*
C130.84116 (17)0.99531 (11)0.0469 (2)0.0352 (5)
C140.89664 (17)0.91915 (11)0.0632 (2)0.0359 (5)
C150.9001 (2)0.87640 (13)0.0711 (3)0.0445 (5)
C160.8467 (2)0.90831 (15)0.2205 (3)0.0508 (6)
C170.7883 (2)0.98150 (15)0.2390 (3)0.0498 (6)
C180.7875 (2)1.02484 (14)0.1056 (3)0.0436 (5)
C190.84024 (17)1.05009 (12)0.1806 (2)0.0357 (5)
N200.89328 (16)1.02345 (10)0.3272 (2)0.0408 (5)
O210.79011 (14)1.11748 (9)0.15592 (17)0.0455 (4)
O220.91361 (15)1.07628 (9)0.45575 (17)0.0469 (4)
O230.94344 (13)0.88957 (8)0.21257 (17)0.0421 (4)
C241.0065 (3)0.81425 (14)0.2352 (4)0.0515 (6)
H150.943 (2)0.8233 (14)0.052 (3)0.046 (6)*
H160.850 (3)0.8753 (17)0.310 (4)0.070 (8)*
H170.748 (2)1.0040 (15)0.347 (3)0.057 (7)*
H180.745 (3)1.0815 (17)0.120 (3)0.063 (7)*
H200.944 (3)0.9699 (17)0.348 (3)0.068 (8)*
H220.830 (4)1.091 (2)0.461 (4)0.097 (11)*
H24A1.079 (3)0.8135 (17)0.193 (4)0.074 (8)*
H24B1.030 (2)0.8052 (13)0.343 (3)0.041 (6)*
H24C0.949 (3)0.7721 (17)0.175 (3)0.060 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0280 (10)0.0377 (10)0.0343 (10)0.0022 (7)0.0113 (8)0.0027 (7)
C20.0282 (10)0.0376 (11)0.0410 (11)0.0013 (8)0.0093 (8)0.0017 (8)
C30.0328 (11)0.0584 (15)0.0537 (13)0.0090 (10)0.0179 (10)0.0042 (10)
C40.0336 (12)0.0746 (17)0.0574 (14)0.0047 (11)0.0238 (10)0.0011 (12)
C50.0439 (13)0.0559 (14)0.0539 (13)0.0160 (11)0.0232 (10)0.0029 (11)
C60.0413 (12)0.0408 (12)0.0435 (11)0.0068 (9)0.0172 (9)0.0057 (9)
C70.0318 (10)0.0322 (10)0.0390 (10)0.0019 (8)0.0146 (8)0.0002 (8)
N80.0394 (10)0.0354 (10)0.0576 (11)0.0042 (7)0.0300 (8)0.0035 (8)
O90.0561 (10)0.0337 (8)0.0740 (11)0.0047 (7)0.0417 (8)0.0004 (7)
O100.0488 (9)0.0418 (9)0.0747 (11)0.0029 (7)0.0426 (8)0.0008 (8)
O110.0391 (8)0.0324 (8)0.0672 (10)0.0068 (6)0.0231 (7)0.0009 (6)
C120.0502 (15)0.0417 (13)0.0657 (17)0.0147 (11)0.0149 (13)0.0035 (11)
C130.0257 (9)0.0389 (11)0.0447 (11)0.0057 (8)0.0159 (8)0.0027 (8)
C140.0278 (10)0.0403 (11)0.0445 (11)0.0063 (8)0.0182 (8)0.0011 (8)
C150.0417 (12)0.0424 (12)0.0554 (13)0.0078 (9)0.0237 (10)0.0070 (10)
C160.0522 (14)0.0579 (14)0.0495 (13)0.0169 (11)0.0260 (11)0.0133 (11)
C170.0512 (13)0.0550 (14)0.0456 (13)0.0133 (11)0.0179 (10)0.0004 (10)
C180.0399 (11)0.0459 (12)0.0473 (12)0.0080 (9)0.0162 (9)0.0026 (9)
C190.0258 (9)0.0420 (11)0.0436 (11)0.0020 (8)0.0167 (8)0.0060 (8)
N200.0407 (10)0.0425 (10)0.0424 (10)0.0092 (8)0.0173 (8)0.0020 (7)
O210.0458 (9)0.0420 (8)0.0516 (9)0.0114 (7)0.0189 (7)0.0065 (6)
O220.0486 (9)0.0516 (10)0.0429 (8)0.0186 (7)0.0168 (7)0.0036 (6)
O230.0433 (8)0.0378 (8)0.0501 (9)0.0068 (6)0.0212 (7)0.0009 (6)
C240.0512 (14)0.0402 (13)0.0672 (17)0.0133 (11)0.0236 (13)0.0007 (11)
Geometric parameters (Å, º) top
C1—C61.387 (3)C13—C181.394 (3)
C1—C21.403 (3)C13—C141.408 (3)
C1—C71.496 (3)C13—C191.497 (3)
C2—O111.359 (2)C14—O231.362 (2)
C2—C31.392 (3)C14—C151.393 (3)
C3—C41.372 (3)C15—C161.386 (3)
C3—H30.87 (3)C15—H151.00 (2)
C4—C51.373 (4)C16—C171.377 (4)
C4—H40.98 (3)C16—H160.97 (3)
C5—C61.386 (3)C17—C181.384 (3)
C5—H50.93 (3)C17—H171.00 (3)
C6—H61.00 (2)C18—H181.05 (3)
C7—O91.243 (2)C19—O211.251 (2)
C7—N81.314 (2)C19—N201.333 (3)
N8—O101.391 (2)N20—O221.404 (2)
N8—H80.88 (3)N20—H201.05 (3)
O10—H100.95 (3)O22—H220.98 (4)
O11—C121.430 (3)O23—C241.431 (3)
C12—H12A0.94 (3)C24—H24A0.99 (3)
C12—H12B0.97 (3)C24—H24B0.92 (2)
C12—H12C0.94 (3)C24—H24C1.00 (3)
C6—C1—C2118.27 (18)C18—C13—C14118.27 (19)
C6—C1—C7116.17 (17)C18—C13—C19116.27 (18)
C2—C1—C7125.54 (17)C14—C13—C19125.37 (18)
O11—C2—C3123.38 (18)O23—C14—C15122.46 (18)
O11—C2—C1117.04 (17)O23—C14—C13117.59 (17)
C3—C2—C1119.57 (19)C15—C14—C13119.94 (19)
C4—C3—C2120.6 (2)C16—C15—C14119.9 (2)
C4—C3—H3120.7 (17)C16—C15—H15123.7 (13)
C2—C3—H3118.7 (18)C14—C15—H15116.4 (13)
C3—C4—C5120.8 (2)C17—C16—C15121.0 (2)
C3—C4—H4118.7 (16)C17—C16—H16122.7 (17)
C5—C4—H4120.5 (16)C15—C16—H16116.3 (17)
C4—C5—C6119.0 (2)C16—C17—C18119.1 (2)
C4—C5—H5119.4 (16)C16—C17—H17120.9 (15)
C6—C5—H5121.6 (16)C18—C17—H17119.9 (15)
C5—C6—C1121.8 (2)C17—C18—C13121.7 (2)
C5—C6—H6121.0 (13)C17—C18—H18118.7 (15)
C1—C6—H6117.2 (13)C13—C18—H18119.5 (15)
O9—C7—N8120.95 (17)O21—C19—N20121.47 (18)
O9—C7—C1120.45 (16)O21—C19—C13121.41 (18)
N8—C7—C1118.43 (16)N20—C19—C13117.11 (17)
C7—N8—O10120.13 (16)C19—N20—O22119.58 (16)
C7—N8—H8125.4 (17)C19—N20—H20121.7 (15)
O10—N8—H8112.1 (17)O22—N20—H20116.3 (15)
N8—O10—H10110.6 (19)N20—O22—H22106 (2)
C2—O11—C12119.15 (18)C14—O23—C24119.46 (17)
O11—C12—H12A108.9 (17)O23—C24—H24A112.5 (17)
O11—C12—H12B107.9 (15)O23—C24—H24B105.6 (14)
H12A—C12—H12B116 (2)H24A—C24—H24B112 (2)
O11—C12—H12C103.3 (17)O23—C24—H24C109.5 (16)
H12A—C12—H12C110 (2)H24A—C24—H24C106 (2)
H12B—C12—H12C110 (2)H24B—C24—H24C112 (2)
C6—C1—C2—O11177.62 (17)C18—C13—C14—O23177.02 (16)
C7—C1—C2—O113.9 (3)C19—C13—C14—O236.3 (3)
C6—C1—C2—C31.8 (3)C18—C13—C14—C151.9 (3)
C7—C1—C2—C3176.70 (19)C19—C13—C14—C15174.79 (18)
O11—C2—C3—C4178.7 (2)O23—C14—C15—C16177.54 (18)
C1—C2—C3—C40.7 (3)C13—C14—C15—C161.3 (3)
C2—C3—C4—C50.8 (4)C14—C15—C16—C171.0 (3)
C3—C4—C5—C61.1 (4)C15—C16—C17—C182.5 (3)
C4—C5—C6—C10.1 (3)C16—C17—C18—C131.9 (3)
C2—C1—C6—C51.5 (3)C14—C13—C18—C170.3 (3)
C7—C1—C6—C5177.12 (19)C19—C13—C18—C17176.69 (18)
C6—C1—C7—O91.3 (3)C18—C13—C19—O212.4 (3)
C2—C1—C7—O9179.82 (19)C14—C13—C19—O21179.06 (17)
C6—C1—C7—N8174.04 (18)C18—C13—C19—N20178.73 (17)
C2—C1—C7—N84.5 (3)C14—C13—C19—N202.0 (3)
O9—C7—N8—O105.1 (3)O21—C19—N20—O2211.4 (3)
C1—C7—N8—O10179.56 (17)C13—C19—N20—O22169.65 (16)
C3—C2—O11—C120.5 (3)C15—C14—O23—C244.4 (3)
C1—C2—O11—C12179.91 (19)C13—C14—O23—C24176.75 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O110.88 (3)2.00 (3)2.609 (2)125 (2)
N8—H8···O21i0.88 (3)2.41 (3)3.102 (2)135 (2)
O10—H10···O21ii0.95 (3)1.88 (3)2.798 (2)162 (3)
N20—H20···O22iii1.05 (3)2.12 (3)2.951 (2)134 (2)
N20—H20···O231.05 (3)1.80 (3)2.588 (2)129 (2)
O22—H22···O9iv0.98 (4)1.68 (4)2.659 (2)172 (3)
C17—H17···O9v1.00 (3)2.32 (3)3.251 (3)155 (2)
C24—H24A···O10vi0.99 (3)2.27 (3)3.123 (3)145 (2)
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y1/2, z+1/2; (iii) x+2, y+2, z+1; (iv) x+1, y+1/2, z+1/2; (v) x+1, y+1/2, z1/2; (vi) x+1, y, z.
 

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