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In the title mol­ecule, C11H9NO, all bond lengths and angles are normal. The crystal structure is stabilized by inter­molecular N—H...O and C—H...O hydrogen bonds and π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000943/cv2175sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000943/cv2175Isup2.hkl
Contains datablock I

CCDC reference: 636233

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.080
  • Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.43 From the CIF: _reflns_number_total 1236 Count of symmetry unique reflns 1244 Completeness (_total/calc) 99.36% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(1-Naphthyl)formamide top
Crystal data top
C11H9NOF(000) = 360
Mr = 171.19Dx = 1.357 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5655 reflections
a = 4.4639 (2) Åθ = 3.1–27.8°
b = 11.8463 (3) ŵ = 0.09 mm1
c = 15.8514 (4) ÅT = 173 K
V = 838.23 (5) Å3Needle, purple
Z = 40.6 × 0.09 × 0.09 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1097 reflections with I > 2σ(I)
ω scansRint = 0.034
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 28.4°, θmin = 2.2°
Tmin = 0.930, Tmax = 0.992h = 55
14873 measured reflectionsk = 1515
1236 independent reflectionsl = 2121
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.1116P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080(Δ/σ)max = 0.006
S = 1.06Δρmax = 0.16 e Å3
1236 reflectionsΔρmin = 0.16 e Å3
122 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2271 (4)0.32418 (12)0.63872 (9)0.0230 (3)
C20.0277 (4)0.24761 (12)0.60755 (9)0.0272 (3)
H20.03410.25210.55030.033*
C30.0869 (4)0.16189 (13)0.66003 (10)0.0310 (4)
H30.2290.10980.63830.037*
C40.0046 (4)0.15331 (12)0.74145 (10)0.0294 (4)
H40.07190.09430.77590.035*
C50.2120 (4)0.23099 (12)0.77569 (9)0.0252 (3)
C60.3098 (4)0.22428 (13)0.86061 (9)0.0308 (4)
H60.23970.16460.89550.037*
C70.5021 (5)0.30177 (14)0.89284 (9)0.0348 (4)
H70.56570.29570.94990.042*
C80.6082 (4)0.39120 (14)0.84247 (9)0.0322 (4)
H80.74030.44570.86590.039*
C90.5218 (4)0.39981 (12)0.76004 (9)0.0263 (3)
H90.59580.46010.72640.032*
C100.3235 (4)0.32010 (12)0.72418 (9)0.0222 (3)
C110.1890 (4)0.48037 (13)0.53816 (10)0.0264 (3)
H110.29690.53210.50390.032*
N10.3503 (3)0.40951 (11)0.58537 (8)0.0255 (3)
O10.0838 (3)0.48498 (10)0.53477 (8)0.0359 (3)
H10.540 (6)0.4194 (16)0.5820 (11)0.037 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0195 (7)0.0236 (6)0.0259 (7)0.0023 (6)0.0034 (6)0.0003 (5)
C20.0249 (8)0.0287 (7)0.0280 (7)0.0021 (7)0.0002 (7)0.0039 (6)
C30.0264 (9)0.0248 (7)0.0418 (8)0.0040 (7)0.0004 (7)0.0054 (6)
C40.0270 (9)0.0225 (7)0.0386 (8)0.0003 (7)0.0072 (7)0.0029 (6)
C50.0229 (8)0.0238 (7)0.0287 (7)0.0046 (6)0.0051 (7)0.0009 (6)
C60.0317 (9)0.0324 (8)0.0284 (7)0.0060 (7)0.0057 (7)0.0046 (6)
C70.0382 (10)0.0415 (9)0.0246 (7)0.0071 (8)0.0013 (7)0.0017 (7)
C80.0305 (9)0.0335 (8)0.0326 (7)0.0006 (7)0.0039 (7)0.0062 (6)
C90.0233 (8)0.0252 (7)0.0303 (7)0.0000 (6)0.0009 (6)0.0029 (6)
C100.0183 (7)0.0234 (6)0.0248 (7)0.0042 (6)0.0027 (6)0.0018 (5)
C110.0247 (8)0.0296 (7)0.0250 (7)0.0020 (6)0.0044 (6)0.0020 (6)
N10.0183 (7)0.0314 (6)0.0269 (6)0.0020 (5)0.0031 (5)0.0030 (5)
O10.0218 (6)0.0406 (6)0.0452 (7)0.0009 (5)0.0021 (5)0.0141 (6)
Geometric parameters (Å, º) top
C1—C21.363 (2)C6—H60.95
C1—C101.422 (2)C7—C81.409 (2)
C1—N11.4281 (19)C7—H70.95
C2—C31.409 (2)C8—C91.366 (2)
C2—H20.95C8—H80.95
C3—C41.357 (2)C9—C101.414 (2)
C3—H30.95C9—H90.95
C4—C51.414 (2)C11—O11.220 (2)
C4—H40.95C11—N11.335 (2)
C5—C61.417 (2)C11—H110.95
C5—C101.424 (2)N1—H10.85 (3)
C6—C71.357 (2)
C2—C1—C10121.34 (13)C6—C7—C8120.54 (14)
C2—C1—N1120.52 (13)C6—C7—H7119.7
C10—C1—N1118.13 (13)C8—C7—H7119.7
C1—C2—C3120.17 (14)C9—C8—C7120.23 (16)
C1—C2—H2119.9C9—C8—H8119.9
C3—C2—H2119.9C7—C8—H8119.9
C4—C3—C2120.41 (15)C8—C9—C10120.76 (14)
C4—C3—H3119.8C8—C9—H9119.6
C2—C3—H3119.8C10—C9—H9119.6
C3—C4—C5120.88 (14)C9—C10—C1123.36 (13)
C3—C4—H4119.6C9—C10—C5118.91 (13)
C5—C4—H4119.6C1—C10—C5117.73 (13)
C4—C5—C6122.00 (14)O1—C11—N1126.23 (16)
C4—C5—C10119.42 (14)O1—C11—H11116.9
C6—C5—C10118.57 (14)N1—C11—H11116.9
C7—C6—C5120.98 (14)C11—N1—C1124.68 (14)
C7—C6—H6119.5C11—N1—H1114.3 (13)
C5—C6—H6119.5C1—N1—H1121.0 (13)
C10—C1—C2—C30.2 (2)C8—C9—C10—C50.7 (2)
N1—C1—C2—C3178.35 (15)C2—C1—C10—C9177.80 (14)
C1—C2—C3—C41.4 (2)N1—C1—C10—C93.6 (2)
C2—C3—C4—C51.1 (3)C2—C1—C10—C51.9 (2)
C3—C4—C5—C6179.65 (16)N1—C1—C10—C5176.64 (13)
C3—C4—C5—C100.7 (2)C4—C5—C10—C9177.57 (14)
C4—C5—C6—C7177.99 (15)C6—C5—C10—C91.4 (2)
C10—C5—C6—C71.0 (2)C4—C5—C10—C12.2 (2)
C5—C6—C7—C80.2 (3)C6—C5—C10—C1178.85 (14)
C6—C7—C8—C91.0 (3)O1—C11—N1—C11.8 (3)
C7—C8—C9—C100.5 (3)C2—C1—N1—C1153.1 (2)
C8—C9—C10—C1179.59 (15)C10—C1—N1—C11128.36 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.85 (3)2.00 (2)2.7971 (19)155.3 (18)
C6—H6···O1ii0.952.503.436 (2)170
Symmetry codes: (i) x+1, y, z; (ii) x, y1/2, z+3/2.
 

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