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In the title compound, C17H13NO2, the hydroxamate group adopts a trans conformation. The crystal packing is stabilized by inter­molecular O—H...O hydrogen bonds and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011798/bq2003sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011798/bq2003Isup2.hkl
Contains datablock I

CCDC reference: 642919

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.051
  • wR factor = 0.121
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _diffrn_reflns_theta_full 27.50 From the CIF: _reflns_number_total 2692 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2857 Completeness (_total/calc) 94.22% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT028_ALERT_3_C _diffrn_measured_fraction_theta_max Low ....... 0.94 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.21 Ratio
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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR2002 (Burla et al., 2002); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: CrystalStructure.

N-Hydroxy-N-phenylnaphthalene-2-carboxamide top
Crystal data top
C17H13NO2F(000) = 552.00
Mr = 263.30Dx = 1.405 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 2692 reflections
a = 27.643 (15) Åθ = 3.1–27.5°
b = 5.638 (3) ŵ = 0.09 mm1
c = 8.018 (4) ÅT = 123 K
β = 95.1601 (18)°Prism, silver
V = 1244.6 (11) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection top
Rigaku Saturn CCD
diffractometer
Rint = 0.048
ω scansθmax = 27.5°, θmin = 4.2°
11623 measured reflectionsh = 3535
2692 independent reflectionsk = 76
2423 reflections with I > 2σ(I)l = 107
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.6927P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121(Δ/σ)max < 0.001
S = 1.13Δρmax = 0.28 e Å3
2692 reflectionsΔρmin = 0.23 e Å3
186 parameters
Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.70302 (4)0.2416 (2)0.10352 (16)0.0223 (2)
O20.72152 (4)0.8111 (2)0.04283 (17)0.0267 (3)
N10.69303 (5)0.4406 (2)0.00038 (17)0.0179 (3)
C10.64310 (6)0.4731 (2)0.0571 (2)0.0171 (3)
C20.60908 (6)0.3149 (2)0.0036 (2)0.0206 (3)
C30.56045 (6)0.3380 (3)0.0632 (2)0.0245 (3)
C40.54540 (6)0.5166 (3)0.1743 (2)0.0243 (3)
C50.57958 (6)0.6729 (3)0.2276 (2)0.0234 (3)
C60.62841 (6)0.6523 (2)0.1709 (2)0.0211 (3)
C70.72925 (6)0.6046 (2)0.0020 (2)0.0179 (3)
C80.80907 (5)0.6742 (2)0.15485 (19)0.0155 (3)
C90.77979 (6)0.5226 (2)0.0568 (2)0.0162 (3)
C100.79874 (6)0.3050 (2)0.0010 (2)0.0168 (3)
C110.84592 (6)0.2435 (2)0.04807 (19)0.0155 (3)
C120.87658 (6)0.3946 (2)0.15196 (19)0.0148 (3)
C130.92557 (6)0.3349 (2)0.2030 (2)0.0174 (3)
C140.95426 (6)0.4847 (2)0.3033 (2)0.0195 (3)
C150.93555 (6)0.7027 (2)0.3568 (2)0.0192 (3)
C160.88868 (6)0.7662 (2)0.3081 (2)0.0169 (3)
C170.85793 (5)0.6139 (2)0.20544 (19)0.0146 (3)
H10.7050 (10)0.112 (4)0.027 (3)0.061 (7)*
H20.61900.19200.07310.025*
H30.53730.22950.02710.029*
H40.51210.53210.21360.029*
H50.56950.79580.30390.028*
H60.65160.75910.20920.025*
H70.79640.82120.18910.019*
H80.77870.20220.06900.020*
H90.85830.09750.01060.019*
H100.93860.18950.16720.021*
H110.98690.44210.33720.023*
H120.95570.80530.42680.023*
H130.87660.91380.34350.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0197 (5)0.0174 (5)0.0296 (6)0.0001 (4)0.0008 (4)0.0091 (4)
O20.0214 (6)0.0145 (5)0.0432 (8)0.0005 (4)0.0023 (5)0.0046 (5)
N10.0179 (6)0.0138 (6)0.0219 (7)0.0000 (4)0.0013 (5)0.0046 (5)
C10.0176 (7)0.0156 (7)0.0183 (8)0.0024 (5)0.0023 (5)0.0030 (5)
C20.0204 (7)0.0192 (7)0.0221 (8)0.0005 (5)0.0018 (6)0.0019 (6)
C30.0197 (8)0.0279 (8)0.0258 (9)0.0059 (6)0.0024 (6)0.0004 (6)
C40.0167 (7)0.0292 (9)0.0267 (9)0.0018 (6)0.0004 (6)0.0028 (7)
C50.0223 (8)0.0223 (8)0.0251 (9)0.0034 (6)0.0015 (6)0.0022 (6)
C60.0202 (8)0.0192 (7)0.0242 (8)0.0006 (6)0.0033 (6)0.0022 (6)
C70.0189 (7)0.0148 (7)0.0201 (8)0.0004 (5)0.0019 (6)0.0006 (5)
C80.0189 (7)0.0117 (6)0.0164 (7)0.0005 (5)0.0051 (5)0.0007 (5)
C90.0175 (7)0.0144 (7)0.0172 (7)0.0002 (5)0.0044 (5)0.0029 (5)
C100.0199 (7)0.0142 (7)0.0166 (7)0.0027 (5)0.0031 (6)0.0008 (5)
C110.0201 (7)0.0121 (6)0.0149 (7)0.0001 (5)0.0051 (5)0.0002 (5)
C120.0201 (7)0.0129 (6)0.0118 (7)0.0003 (5)0.0045 (5)0.0031 (5)
C130.0198 (7)0.0158 (7)0.0169 (7)0.0013 (5)0.0033 (6)0.0018 (5)
C140.0161 (7)0.0232 (8)0.0189 (8)0.0000 (5)0.0010 (6)0.0034 (6)
C150.0235 (8)0.0193 (7)0.0148 (7)0.0054 (5)0.0012 (6)0.0002 (6)
C160.0239 (7)0.0127 (7)0.0145 (7)0.0026 (5)0.0033 (5)0.0000 (5)
C170.0188 (7)0.0131 (6)0.0122 (7)0.0010 (5)0.0039 (5)0.0019 (5)
Geometric parameters (Å, º) top
O1—N11.4063 (17)C13—C141.369 (2)
O2—C71.2320 (19)C14—C151.415 (2)
N1—C11.427 (2)C15—C161.367 (2)
N1—C71.362 (2)C16—C171.419 (2)
C1—C21.392 (2)O1—H10.96 (2)
C1—C61.397 (2)C2—H20.950
C2—C31.392 (2)C3—H30.950
C3—C41.384 (2)C4—H40.950
C4—C51.387 (2)C5—H50.950
C5—C61.390 (2)C6—H60.950
C7—C91.499 (2)C8—H70.950
C8—C91.374 (2)C10—H80.950
C8—C171.4163 (19)C11—H90.950
C9—C101.422 (2)C13—H100.950
C10—C111.369 (2)C14—H110.950
C11—C121.418 (2)C15—H120.950
C12—C131.420 (2)C16—H130.950
C12—C171.420 (2)
O1···O2i2.7637 (16)H3···H5i3.472
O1···N1ii3.3787 (18)H3···H5vii3.156
O1···C1ii3.525 (2)H3···H5ii3.533
O2···O1iii2.7637 (16)H3···H5vi3.297
O2···C8iv3.5770 (19)H4···C3ix3.091
O2···C10iii3.5068 (18)H4···C3viii3.207
N1···O1v3.3787 (18)H4···C4vii3.394
C1···O1v3.525 (2)H4···C4ix3.247
C8···O2vi3.5770 (19)H4···C5vii3.245
C8···C11iii3.497 (2)H4···H3ix2.629
C10···O2i3.5068 (18)H4···H3viii2.805
C11···C8i3.497 (2)H4···H3v3.048
C11···C12v3.449 (2)H4···H4vii2.944
C11···C16i3.542 (2)H4···H4ix2.944
C11···C17v3.447 (2)H4···H4viii3.567
C12···C11ii3.449 (2)H4···H5vii2.633
C12···C16iv3.396 (2)H5···C1iv3.272
C13···C16i3.491 (2)H5···C2iv2.983
C16···C11iii3.542 (2)H5···C3iv2.925
C16···C12vi3.396 (2)H5···C4ix3.400
C16···C13iii3.491 (2)H5···C4iv3.166
C16···C17vi3.437 (2)H5···C5iv3.438
C17···C11ii3.447 (2)H5···C6iv3.502
C17···C16iv3.437 (2)H5···H2v3.264
O1···H1ii3.49 (2)H5···H2iv3.381
O1···H6ii3.554H5···H3iii3.472
O1···H6vi3.548H5···H3ix3.156
O1···H7i3.526H5···H3v3.533
O1···H8ii3.222H5···H3iv3.297
O2···H1iii1.85 (2)H5···H4ix2.633
O2···H6vi3.461H6···O1v3.554
O2···H7iv3.203H6···O1iv3.548
O2···H8iii2.731H6···O2iv3.461
N1···H6vi3.175H6···N1iv3.175
C1···H2v3.122H6···C1iv3.162
C1···H5vi3.272H6···C2iv3.496
C1···H6vi3.162H6···C7iv3.385
C2···H2v3.430H6···H1iii3.036
C2···H5vi2.983H6···H1v3.406
C2···H6vi3.496H6···H2iii3.502
C3···H2v3.464H6···H2v3.169
C3···H4vii3.091H7···O1iii3.526
C3···H4viii3.207H7···O2vi3.203
C3···H5vi2.925H7···C7vi3.279
C4···H2v3.219H7···C9vi3.149
C4···H3ix3.377H7···C10iii3.121
C4···H3viii3.247H7···C10vi3.267
C4···H3v3.141H7···C11iii3.017
C4···H4vii3.247H7···H1iii3.189
C4···H4ix3.394H7···H8iii2.993
C4···H5vii3.400H7···H8ii3.589
C4···H5vi3.166H7···H8vi3.376
C5···H2v2.878H7···H9iii2.801
C5···H3v3.432H8···O1v3.222
C5···H4ix3.245H8···O2i2.731
C5···H5vi3.438H8···C8i3.538
C6···H2v2.820H8···C8v3.232
C6···H5vi3.502H8···C9v3.260
C7···H1iii2.95 (2)H8···C10v3.542
C7···H6vi3.385H8···C17v3.458
C7···H7iv3.279H8···H7i2.993
C8···H8iii3.538H8···H7v3.589
C8···H8ii3.232H8···H7iv3.376
C8···H9iii3.028H8···H13iv3.584
C8···H9ii3.411H9···C8i3.028
C8···H13iv3.286H9···C8v3.411
C9···H7iv3.149H9···C12v2.965
C9···H8ii3.260H9···C13v3.243
C9···H13iv3.322H9···C14v3.288
C10···H7i3.121H9···C15v3.070
C10···H7iv3.267H9···C16i3.087
C10···H8ii3.542H9···C16v2.792
C10···H13iv3.037H9···C17i3.143
C11···H7i3.017H9···C17v2.721
C11···H13i3.070H9···H7i2.801
C11···H13iv2.719H9···H13i2.865
C12···H9ii2.965H9···H13v3.238
C12···H12iv3.408H9···H13iv3.125
C12···H13i3.116H10···C14x3.168
C12···H13iv2.699H10···C14v3.145
C13···H9ii3.243H10···C15i3.142
C13···H11x3.317H10···C15x3.503
C13···H12i3.544H10···C15v3.325
C13···H12x3.536H10···C16i3.026
C13···H12iv3.169H10···H11x2.491
C13···H13i3.003H10···H11v3.158
C13···H13iv3.384H10···H12i3.012
C14···H9ii3.288H10···H12x3.153
C14···H10xi3.168H10···H12v3.448
C14···H10ii3.145H10···H12iv3.495
C14···H11xi3.300H10···H13i2.791
C14···H11xii3.206H11···C13xi3.317
C14···H12x3.384H11···C14x3.300
C14···H12xii3.548H11···C14xii3.206
C14···H12iv3.246H11···C15x3.072
C15···H9ii3.070H11···C15xii3.215
C15···H10iii3.142H11···H10xi2.491
C15···H10xi3.503H11···H10ii3.158
C15···H10ii3.325H11···H11x3.257
C15···H11xi3.072H11···H11xi3.257
C15···H11xii3.215H11···H11xii2.725
C15···H12iv3.542H11···H12x2.863
C16···H9iii3.087H11···H12xii2.740
C16···H9ii2.792H12···C12vi3.408
C16···H10iii3.026H12···C13iii3.544
C17···H8ii3.458H12···C13xi3.536
C17···H9iii3.143H12···C13vi3.169
C17···H9ii2.721H12···C14xi3.384
C17···H13iv2.997H12···C14xii3.548
H1···O1v3.49 (2)H12···C14vi3.246
H1···O2i1.85 (2)H12···C15vi3.542
H1···C7i2.95 (2)H12···H10iii3.012
H1···H6i3.036H12···H10xi3.153
H1···H6ii3.406H12···H10ii3.448
H1···H7i3.189H12···H10vi3.495
H2···C1ii3.122H12···H11xi2.863
H2···C2ii3.430H12···H11xii2.740
H2···C3ii3.464H12···H12xiv3.420
H2···C4ii3.219H13···C8vi3.286
H2···C5ii2.878H13···C9vi3.322
H2···C6ii2.820H13···C10vi3.037
H2···H5ii3.264H13···C11iii3.070
H2···H5vi3.381H13···C11vi2.719
H2···H6i3.502H13···C12iii3.116
H2···H6ii3.169H13···C12vi2.699
H3···C4vii3.377H13···C13iii3.003
H3···C4viii3.247H13···C13vi3.384
H3···C4ii3.141H13···C17vi2.997
H3···C5ii3.432H13···H8vi3.584
H3···H3xiii3.360H13···H9iii2.865
H3···H4vii2.629H13···H9ii3.238
H3···H4viii2.805H13···H9vi3.125
H3···H4ii3.048H13···H10iii2.791
O1—N1—C1115.17 (11)C8—C17—C16121.81 (13)
O1—N1—C7115.50 (12)C12—C17—C16119.16 (13)
C1—N1—C7127.22 (12)N1—O1—H1104.5 (17)
N1—C1—C2118.62 (13)C1—C2—H2120.3
N1—C1—C6121.30 (14)C3—C2—H2120.2
C2—C1—C6120.01 (14)C2—C3—H3119.5
C1—C2—C3119.51 (14)C4—C3—H3119.5
C2—C3—C4120.96 (15)C3—C4—H4120.4
C3—C4—C5119.13 (15)C5—C4—H4120.4
C4—C5—C6120.99 (15)C4—C5—H5119.5
C1—C6—C5119.38 (15)C6—C5—H5119.5
O2—C7—N1122.06 (14)C1—C6—H6120.3
O2—C7—C9120.62 (14)C5—C6—H6120.3
N1—C7—C9117.30 (13)C9—C8—H7119.6
C9—C8—C17120.79 (13)C17—C8—H7119.6
C7—C9—C8117.48 (13)C9—C10—H8120.0
C7—C9—C10122.24 (13)C11—C10—H8120.0
C8—C9—C10120.12 (14)C10—C11—H9119.5
C9—C10—C11120.01 (13)C12—C11—H9119.5
C10—C11—C12120.93 (14)C12—C13—H10119.7
C11—C12—C13122.08 (13)C14—C13—H10119.7
C11—C12—C17119.09 (14)C13—C14—H11119.8
C13—C12—C17118.82 (13)C15—C14—H11119.8
C12—C13—C14120.68 (14)C14—C15—H12119.9
C13—C14—C15120.38 (14)C16—C15—H12119.9
C14—C15—C16120.28 (14)C15—C16—H13119.7
C15—C16—C17120.68 (13)C17—C16—H13119.7
C8—C17—C12119.03 (13)
O1—N1—C1—C22.1 (2)C9—C8—C17—C120.6 (2)
O1—N1—C1—C6174.89 (14)C9—C8—C17—C16179.30 (15)
O1—N1—C7—O2159.62 (14)C17—C8—C9—C7177.22 (14)
O1—N1—C7—C921.9 (2)C17—C8—C9—C101.7 (2)
C1—N1—C7—O22.9 (2)C7—C9—C10—C11176.81 (15)
C1—N1—C7—C9175.50 (14)C8—C9—C10—C111.5 (2)
C7—N1—C1—C2160.51 (15)C9—C10—C11—C120.2 (2)
C7—N1—C1—C622.5 (2)C10—C11—C12—C13179.83 (15)
N1—C1—C2—C3177.55 (14)C10—C11—C12—C170.8 (2)
N1—C1—C6—C5177.99 (15)C11—C12—C13—C14179.96 (12)
C2—C1—C6—C51.0 (2)C11—C12—C17—C80.6 (2)
C6—C1—C2—C30.5 (2)C11—C12—C17—C16179.45 (14)
C1—C2—C3—C40.3 (2)C13—C12—C17—C8179.99 (12)
C2—C3—C4—C50.6 (2)C13—C12—C17—C160.1 (2)
C3—C4—C5—C60.1 (2)C17—C12—C13—C140.6 (2)
C4—C5—C6—C10.8 (2)C12—C13—C14—C150.4 (2)
O2—C7—C9—C840.8 (2)C13—C14—C15—C160.3 (2)
O2—C7—C9—C10134.64 (17)C14—C15—C16—C170.8 (2)
N1—C7—C9—C8140.73 (15)C15—C16—C17—C8179.28 (15)
N1—C7—C9—C1043.8 (2)C15—C16—C17—C120.6 (2)
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z+1/2; (iii) x, y+1, z; (iv) x, y+3/2, z1/2; (v) x, y+1/2, z1/2; (vi) x, y+3/2, z+1/2; (vii) x+1, y1/2, z1/2; (viii) x+1, y+1, z; (ix) x+1, y+1/2, z1/2; (x) x+2, y1/2, z+1/2; (xi) x+2, y+1/2, z+1/2; (xii) x+2, y+1, z+1; (xiii) x+1, y, z; (xiv) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.96 (2)1.85 (2)2.7637 (16)157 (2)
C2—H2···Cg1ii0.952.843.618 (2)139
C5—H5···Cg1iv0.952.913.690 (2)141
C11—H9···Cg3v0.952.683.430 (2)137
C16—H13···Cg2vi0.952.673.394 (2)133
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z+1/2; (iv) x, y+3/2, z1/2; (v) x, y+1/2, z1/2; (vi) x, y+3/2, z+1/2.
 

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