In the title molecule, C
11H
9NO, 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
CCDC reference: 636233
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
C11H9NO | F(000) = 360 |
Mr = 171.19 | Dx = 1.357 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5655 reflections |
a = 4.4639 (2) Å | θ = 3.1–27.8° |
b = 11.8463 (3) Å | µ = 0.09 mm−1 |
c = 15.8514 (4) Å | T = 173 K |
V = 838.23 (5) Å3 | Needle, purple |
Z = 4 | 0.6 × 0.09 × 0.09 mm |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 1097 reflections with I > 2σ(I) |
ω scans | Rint = 0.034 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.4°, θmin = 2.2° |
Tmin = 0.930, Tmax = 0.992 | h = −5→5 |
14873 measured reflections | k = −15→15 |
1236 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.06 | Δρmax = 0.16 e Å−3 |
1236 reflections | Δρmin = −0.16 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2271 (4) | 0.32418 (12) | 0.63872 (9) | 0.0230 (3) | |
C2 | 0.0277 (4) | 0.24761 (12) | 0.60755 (9) | 0.0272 (3) | |
H2 | −0.0341 | 0.2521 | 0.5503 | 0.033* | |
C3 | −0.0869 (4) | 0.16189 (13) | 0.66003 (10) | 0.0310 (4) | |
H3 | −0.229 | 0.1098 | 0.6383 | 0.037* | |
C4 | 0.0046 (4) | 0.15331 (12) | 0.74145 (10) | 0.0294 (4) | |
H4 | −0.0719 | 0.0943 | 0.7759 | 0.035* | |
C5 | 0.2120 (4) | 0.23099 (12) | 0.77569 (9) | 0.0252 (3) | |
C6 | 0.3098 (4) | 0.22428 (13) | 0.86061 (9) | 0.0308 (4) | |
H6 | 0.2397 | 0.1646 | 0.8955 | 0.037* | |
C7 | 0.5021 (5) | 0.30177 (14) | 0.89284 (9) | 0.0348 (4) | |
H7 | 0.5657 | 0.2957 | 0.9499 | 0.042* | |
C8 | 0.6082 (4) | 0.39120 (14) | 0.84247 (9) | 0.0322 (4) | |
H8 | 0.7403 | 0.4457 | 0.8659 | 0.039* | |
C9 | 0.5218 (4) | 0.39981 (12) | 0.76004 (9) | 0.0263 (3) | |
H9 | 0.5958 | 0.4601 | 0.7264 | 0.032* | |
C10 | 0.3235 (4) | 0.32010 (12) | 0.72418 (9) | 0.0222 (3) | |
C11 | 0.1890 (4) | 0.48037 (13) | 0.53816 (10) | 0.0264 (3) | |
H11 | 0.2969 | 0.5321 | 0.5039 | 0.032* | |
N1 | 0.3503 (3) | 0.40951 (11) | 0.58537 (8) | 0.0255 (3) | |
O1 | −0.0838 (3) | 0.48498 (10) | 0.53477 (8) | 0.0359 (3) | |
H1 | 0.540 (6) | 0.4194 (16) | 0.5820 (11) | 0.037 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0195 (7) | 0.0236 (6) | 0.0259 (7) | 0.0023 (6) | 0.0034 (6) | −0.0003 (5) |
C2 | 0.0249 (8) | 0.0287 (7) | 0.0280 (7) | 0.0021 (7) | 0.0002 (7) | −0.0039 (6) |
C3 | 0.0264 (9) | 0.0248 (7) | 0.0418 (8) | −0.0040 (7) | 0.0004 (7) | −0.0054 (6) |
C4 | 0.0270 (9) | 0.0225 (7) | 0.0386 (8) | 0.0003 (7) | 0.0072 (7) | 0.0029 (6) |
C5 | 0.0229 (8) | 0.0238 (7) | 0.0287 (7) | 0.0046 (6) | 0.0051 (7) | −0.0009 (6) |
C6 | 0.0317 (9) | 0.0324 (8) | 0.0284 (7) | 0.0060 (7) | 0.0057 (7) | 0.0046 (6) |
C7 | 0.0382 (10) | 0.0415 (9) | 0.0246 (7) | 0.0071 (8) | −0.0013 (7) | −0.0017 (7) |
C8 | 0.0305 (9) | 0.0335 (8) | 0.0326 (7) | 0.0006 (7) | −0.0039 (7) | −0.0062 (6) |
C9 | 0.0233 (8) | 0.0252 (7) | 0.0303 (7) | 0.0000 (6) | 0.0009 (6) | −0.0029 (6) |
C10 | 0.0183 (7) | 0.0234 (6) | 0.0248 (7) | 0.0042 (6) | 0.0027 (6) | −0.0018 (5) |
C11 | 0.0247 (8) | 0.0296 (7) | 0.0250 (7) | −0.0020 (6) | 0.0044 (6) | 0.0020 (6) |
N1 | 0.0183 (7) | 0.0314 (6) | 0.0269 (6) | −0.0020 (5) | 0.0031 (5) | 0.0030 (5) |
O1 | 0.0218 (6) | 0.0406 (6) | 0.0452 (7) | 0.0009 (5) | 0.0021 (5) | 0.0141 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.363 (2) | C6—H6 | 0.95 |
C1—C10 | 1.422 (2) | C7—C8 | 1.409 (2) |
C1—N1 | 1.4281 (19) | C7—H7 | 0.95 |
C2—C3 | 1.409 (2) | C8—C9 | 1.366 (2) |
C2—H2 | 0.95 | C8—H8 | 0.95 |
C3—C4 | 1.357 (2) | C9—C10 | 1.414 (2) |
C3—H3 | 0.95 | C9—H9 | 0.95 |
C4—C5 | 1.414 (2) | C11—O1 | 1.220 (2) |
C4—H4 | 0.95 | C11—N1 | 1.335 (2) |
C5—C6 | 1.417 (2) | C11—H11 | 0.95 |
C5—C10 | 1.424 (2) | N1—H1 | 0.85 (3) |
C6—C7 | 1.357 (2) | | |
| | | |
C2—C1—C10 | 121.34 (13) | C6—C7—C8 | 120.54 (14) |
C2—C1—N1 | 120.52 (13) | C6—C7—H7 | 119.7 |
C10—C1—N1 | 118.13 (13) | C8—C7—H7 | 119.7 |
C1—C2—C3 | 120.17 (14) | C9—C8—C7 | 120.23 (16) |
C1—C2—H2 | 119.9 | C9—C8—H8 | 119.9 |
C3—C2—H2 | 119.9 | C7—C8—H8 | 119.9 |
C4—C3—C2 | 120.41 (15) | C8—C9—C10 | 120.76 (14) |
C4—C3—H3 | 119.8 | C8—C9—H9 | 119.6 |
C2—C3—H3 | 119.8 | C10—C9—H9 | 119.6 |
C3—C4—C5 | 120.88 (14) | C9—C10—C1 | 123.36 (13) |
C3—C4—H4 | 119.6 | C9—C10—C5 | 118.91 (13) |
C5—C4—H4 | 119.6 | C1—C10—C5 | 117.73 (13) |
C4—C5—C6 | 122.00 (14) | O1—C11—N1 | 126.23 (16) |
C4—C5—C10 | 119.42 (14) | O1—C11—H11 | 116.9 |
C6—C5—C10 | 118.57 (14) | N1—C11—H11 | 116.9 |
C7—C6—C5 | 120.98 (14) | C11—N1—C1 | 124.68 (14) |
C7—C6—H6 | 119.5 | C11—N1—H1 | 114.3 (13) |
C5—C6—H6 | 119.5 | C1—N1—H1 | 121.0 (13) |
| | | |
C10—C1—C2—C3 | −0.2 (2) | C8—C9—C10—C5 | 0.7 (2) |
N1—C1—C2—C3 | 178.35 (15) | C2—C1—C10—C9 | −177.80 (14) |
C1—C2—C3—C4 | −1.4 (2) | N1—C1—C10—C9 | 3.6 (2) |
C2—C3—C4—C5 | 1.1 (3) | C2—C1—C10—C5 | 1.9 (2) |
C3—C4—C5—C6 | 179.65 (16) | N1—C1—C10—C5 | −176.64 (13) |
C3—C4—C5—C10 | 0.7 (2) | C4—C5—C10—C9 | 177.57 (14) |
C4—C5—C6—C7 | −177.99 (15) | C6—C5—C10—C9 | −1.4 (2) |
C10—C5—C6—C7 | 1.0 (2) | C4—C5—C10—C1 | −2.2 (2) |
C5—C6—C7—C8 | 0.2 (3) | C6—C5—C10—C1 | 178.85 (14) |
C6—C7—C8—C9 | −1.0 (3) | O1—C11—N1—C1 | 1.8 (3) |
C7—C8—C9—C10 | 0.5 (3) | C2—C1—N1—C11 | 53.1 (2) |
C8—C9—C10—C1 | −179.59 (15) | C10—C1—N1—C11 | −128.36 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.85 (3) | 2.00 (2) | 2.7971 (19) | 155.3 (18) |
C6—H6···O1ii | 0.95 | 2.50 | 3.436 (2) | 170 |
Symmetry codes: (i) x+1, y, z; (ii) −x, y−1/2, −z+3/2. |