The crystal structure of the title compound, C
19H
17N
1O
2, obtained
via a one-pot synthesis, is stabilized by intramolecular N—H
O and intermolecular O—H
O hydrogen bonds.
Supporting information
CCDC reference: 636646
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.113
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.79 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2
PLAT391_ALERT_3_C Deviating Methyl C1 H-C-H Bond Angle ...... 101.00 Deg.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 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
2 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
Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
N-[(2-Hydroxynaphthalen-1-yl)(phenyl)methyl]acetamide
top
Crystal data top
C19H17NO2 | F(000) = 616 |
Mr = 291.34 | Dx = 1.291 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2000 reflections |
a = 11.835 (3) Å | θ = 1.8–27.9° |
b = 7.3428 (10) Å | µ = 0.08 mm−1 |
c = 18.034 (3) Å | T = 293 K |
β = 106.958 (16)° | Block, colorless |
V = 1499.1 (5) Å3 | 0.50 × 0.35 × 0.25 mm |
Z = 4 | |
Data collection top
Stoe IPDSII diffractometer | 2932 reflections with I > 2σ(I) |
φ? or ω? scans | Rint = 0.023 |
Absorption correction: numerical [shape of crystal determined optically (X-STEP32; Stoe & Cie, 2000)] | θmax = 27.9°, θmin = 1.8° |
Tmin = 0.960, Tmax = 0.980 | h = −15→12 |
9203 measured reflections | k = −9→8 |
3534 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0468P)2 + 0.3551P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max = 0.003 |
S = 1.06 | Δρmax = 0.19 e Å−3 |
3534 reflections | Δρmin = −0.16 e Å−3 |
267 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 | 0.52432 (18) | 0.2288 (3) | −0.13390 (10) | 0.0620 (5) | |
H1A | 0.512 (2) | 0.351 (4) | −0.1484 (13) | 0.100 (7)* | |
H1B | 0.544 (2) | 0.166 (4) | −0.1744 (16) | 0.117 (9)* | |
H1C | 0.456 (3) | 0.163 (4) | −0.1311 (16) | 0.125 (10)* | |
C2 | 0.62103 (12) | 0.20268 (17) | −0.05946 (8) | 0.0429 (3) | |
C3 | 0.74050 (10) | 0.34580 (16) | 0.06139 (7) | 0.0356 (3) | |
H3 | 0.7755 (12) | 0.2240 (19) | 0.0642 (7) | 0.033 (3)* | |
C4 | 0.83801 (11) | 0.48501 (16) | 0.06814 (7) | 0.0356 (3) | |
C5 | 0.81283 (11) | 0.66008 (17) | 0.04035 (7) | 0.0400 (3) | |
C6 | 0.90359 (14) | 0.78625 (19) | 0.04170 (8) | 0.0476 (3) | |
H6 | 0.8797 (16) | 0.904 (3) | 0.0180 (10) | 0.065 (5)* | |
C7 | 1.01820 (14) | 0.7396 (2) | 0.07391 (8) | 0.0503 (3) | |
H7 | 1.0792 (17) | 0.825 (3) | 0.0752 (10) | 0.069 (5)* | |
C8 | 1.04933 (12) | 0.5661 (2) | 0.10748 (7) | 0.0439 (3) | |
C9 | 1.16843 (13) | 0.5177 (3) | 0.14473 (9) | 0.0601 (4) | |
H9 | 1.2248 (19) | 0.612 (3) | 0.1451 (11) | 0.078 (6)* | |
C10 | 1.19735 (14) | 0.3510 (3) | 0.17759 (10) | 0.0672 (5) | |
H10 | 1.279 (2) | 0.322 (3) | 0.2052 (12) | 0.087 (6)* | |
C11 | 1.10896 (14) | 0.2236 (3) | 0.17452 (10) | 0.0614 (4) | |
H11 | 1.1304 (18) | 0.100 (3) | 0.1967 (11) | 0.077 (6)* | |
C12 | 0.99279 (13) | 0.2639 (2) | 0.13940 (8) | 0.0480 (3) | |
H12 | 0.9346 (18) | 0.171 (3) | 0.1393 (10) | 0.072 (5)* | |
C13 | 0.95863 (11) | 0.43653 (18) | 0.10435 (7) | 0.0378 (3) | |
C14 | 0.68195 (10) | 0.35352 (16) | 0.12644 (7) | 0.0367 (3) | |
C15 | 0.73801 (13) | 0.43172 (19) | 0.19787 (8) | 0.0454 (3) | |
H15 | 0.8155 (15) | 0.493 (2) | 0.2062 (9) | 0.053 (4)* | |
C16 | 0.68677 (15) | 0.4250 (2) | 0.25790 (9) | 0.0531 (4) | |
H16 | 0.7279 (17) | 0.478 (3) | 0.3081 (11) | 0.069 (5)* | |
C17 | 0.57928 (14) | 0.3410 (2) | 0.24760 (9) | 0.0531 (4) | |
H17 | 0.5438 (16) | 0.335 (2) | 0.2898 (10) | 0.063 (5)* | |
C18 | 0.52270 (14) | 0.2621 (2) | 0.17713 (10) | 0.0536 (4) | |
H18 | 0.4466 (17) | 0.201 (2) | 0.1689 (10) | 0.067 (5)* | |
C19 | 0.57360 (12) | 0.2681 (2) | 0.11701 (8) | 0.0461 (3) | |
H19 | 0.5335 (16) | 0.212 (2) | 0.0668 (10) | 0.061 (5)* | |
N1 | 0.65267 (10) | 0.34965 (14) | −0.01512 (6) | 0.0391 (2) | |
H1 | 0.6182 (14) | 0.456 (2) | −0.0311 (9) | 0.049 (4)* | |
O1 | 0.66685 (12) | 0.05345 (14) | −0.04059 (7) | 0.0742 (4) | |
O2 | 0.69735 (9) | 0.70907 (14) | 0.01072 (7) | 0.0548 (3) | |
H2 | 0.692 (2) | 0.821 (3) | −0.0051 (13) | 0.089 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0695 (11) | 0.0465 (9) | 0.0519 (9) | −0.0032 (8) | −0.0110 (8) | −0.0018 (7) |
C2 | 0.0447 (7) | 0.0310 (6) | 0.0462 (7) | −0.0023 (5) | 0.0026 (5) | 0.0023 (5) |
C3 | 0.0316 (6) | 0.0291 (5) | 0.0404 (6) | 0.0013 (5) | 0.0015 (5) | 0.0029 (4) |
C4 | 0.0331 (6) | 0.0339 (6) | 0.0374 (6) | −0.0011 (5) | 0.0065 (5) | 0.0010 (5) |
C5 | 0.0402 (7) | 0.0347 (6) | 0.0418 (6) | −0.0015 (5) | 0.0066 (5) | 0.0012 (5) |
C6 | 0.0581 (9) | 0.0370 (7) | 0.0474 (7) | −0.0085 (6) | 0.0152 (6) | 0.0028 (5) |
C7 | 0.0501 (8) | 0.0542 (8) | 0.0496 (7) | −0.0183 (7) | 0.0192 (6) | −0.0032 (6) |
C8 | 0.0358 (6) | 0.0574 (8) | 0.0395 (6) | −0.0073 (6) | 0.0125 (5) | −0.0057 (6) |
C9 | 0.0356 (7) | 0.0857 (12) | 0.0586 (9) | −0.0097 (8) | 0.0130 (6) | −0.0058 (8) |
C10 | 0.0348 (8) | 0.0945 (14) | 0.0652 (10) | 0.0105 (8) | 0.0031 (7) | −0.0019 (9) |
C11 | 0.0454 (8) | 0.0688 (11) | 0.0599 (9) | 0.0144 (8) | −0.0004 (7) | 0.0050 (8) |
C12 | 0.0386 (7) | 0.0498 (8) | 0.0489 (7) | 0.0046 (6) | 0.0023 (6) | 0.0048 (6) |
C13 | 0.0332 (6) | 0.0444 (7) | 0.0342 (6) | 0.0002 (5) | 0.0073 (5) | −0.0017 (5) |
C14 | 0.0338 (6) | 0.0295 (5) | 0.0425 (6) | 0.0014 (5) | 0.0044 (5) | 0.0040 (5) |
C15 | 0.0420 (7) | 0.0424 (7) | 0.0476 (7) | −0.0060 (6) | 0.0066 (6) | −0.0019 (5) |
C16 | 0.0583 (9) | 0.0525 (8) | 0.0452 (7) | −0.0005 (7) | 0.0101 (6) | −0.0034 (6) |
C17 | 0.0589 (9) | 0.0483 (8) | 0.0575 (8) | 0.0065 (7) | 0.0254 (7) | 0.0052 (7) |
C18 | 0.0443 (8) | 0.0499 (8) | 0.0702 (10) | −0.0057 (6) | 0.0226 (7) | −0.0001 (7) |
C19 | 0.0380 (7) | 0.0451 (7) | 0.0522 (8) | −0.0061 (6) | 0.0085 (6) | −0.0042 (6) |
N1 | 0.0394 (6) | 0.0296 (5) | 0.0411 (5) | 0.0022 (4) | 0.0003 (4) | 0.0033 (4) |
O1 | 0.0872 (9) | 0.0308 (5) | 0.0784 (8) | 0.0084 (5) | −0.0169 (6) | −0.0019 (5) |
O2 | 0.0441 (6) | 0.0329 (5) | 0.0771 (7) | 0.0043 (4) | 0.0017 (5) | 0.0105 (5) |
Geometric parameters (Å, º) top
C1—C2 | 1.501 (2) | C9—H9 | 0.96 (2) |
C1—H1A | 0.94 (3) | C10—C11 | 1.392 (3) |
C1—H1B | 0.95 (3) | C10—H10 | 0.98 (2) |
C1—H1C | 0.96 (3) | C11—C12 | 1.368 (2) |
C2—O1 | 1.2260 (16) | C11—H11 | 1.00 (2) |
C2—N1 | 1.3303 (16) | C12—C13 | 1.4214 (19) |
C3—N1 | 1.4657 (15) | C12—H12 | 0.97 (2) |
C3—C4 | 1.5197 (17) | C14—C15 | 1.3895 (18) |
C3—C14 | 1.5277 (18) | C14—C19 | 1.3926 (18) |
C3—H3 | 0.981 (14) | C15—C16 | 1.388 (2) |
C4—C5 | 1.3804 (17) | C15—H15 | 0.991 (17) |
C4—C13 | 1.4309 (17) | C16—C17 | 1.377 (2) |
C5—O2 | 1.3626 (16) | C16—H16 | 0.975 (19) |
C5—C6 | 1.4134 (19) | C17—C18 | 1.380 (2) |
C6—C7 | 1.355 (2) | C17—H17 | 0.972 (17) |
C6—H6 | 0.970 (19) | C18—C19 | 1.386 (2) |
C7—C8 | 1.412 (2) | C18—H18 | 0.98 (2) |
C7—H7 | 0.951 (19) | C19—H19 | 0.981 (18) |
C8—C9 | 1.418 (2) | N1—H1 | 0.889 (17) |
C8—C13 | 1.4233 (18) | O2—H2 | 0.87 (2) |
C9—C10 | 1.360 (3) | | |
| | | |
C2—C1—H1A | 112.8 (14) | C9—C10—H10 | 120.2 (13) |
C2—C1—H1B | 109.3 (16) | C11—C10—H10 | 119.9 (13) |
H1A—C1—H1B | 108 (2) | C12—C11—C10 | 121.00 (17) |
C2—C1—H1C | 109.0 (17) | C12—C11—H11 | 119.2 (12) |
H1A—C1—H1C | 116 (2) | C10—C11—H11 | 119.8 (12) |
H1B—C1—H1C | 102 (2) | C11—C12—C13 | 121.06 (15) |
O1—C2—N1 | 122.27 (12) | C11—C12—H12 | 117.8 (11) |
O1—C2—C1 | 121.52 (13) | C13—C12—H12 | 121.2 (11) |
N1—C2—C1 | 116.20 (12) | C12—C13—C8 | 117.72 (12) |
N1—C3—C4 | 112.08 (10) | C12—C13—C4 | 122.77 (12) |
N1—C3—C14 | 111.48 (10) | C8—C13—C4 | 119.49 (12) |
C4—C3—C14 | 114.68 (10) | C15—C14—C19 | 118.23 (13) |
N1—C3—H3 | 103.8 (7) | C15—C14—C3 | 121.76 (11) |
C4—C3—H3 | 108.0 (8) | C19—C14—C3 | 119.82 (11) |
C14—C3—H3 | 105.9 (8) | C16—C15—C14 | 120.63 (13) |
C5—C4—C13 | 118.58 (11) | C16—C15—H15 | 119.6 (9) |
C5—C4—C3 | 121.26 (11) | C14—C15—H15 | 119.8 (9) |
C13—C4—C3 | 120.16 (11) | C17—C16—C15 | 120.50 (14) |
O2—C5—C4 | 118.28 (11) | C17—C16—H16 | 119.7 (11) |
O2—C5—C6 | 120.27 (12) | C15—C16—H16 | 119.8 (11) |
C4—C5—C6 | 121.45 (12) | C16—C17—C18 | 119.58 (14) |
C7—C6—C5 | 120.17 (13) | C16—C17—H17 | 120.6 (11) |
C7—C6—H6 | 122.8 (11) | C18—C17—H17 | 119.8 (11) |
C5—C6—H6 | 117.0 (11) | C17—C18—C19 | 120.15 (14) |
C6—C7—C8 | 121.02 (13) | C17—C18—H18 | 120.6 (11) |
C6—C7—H7 | 120.1 (11) | C19—C18—H18 | 119.2 (11) |
C8—C7—H7 | 118.8 (11) | C18—C19—C14 | 120.90 (13) |
C7—C8—C9 | 121.87 (14) | C18—C19—H19 | 120.4 (10) |
C7—C8—C13 | 119.11 (12) | C14—C19—H19 | 118.7 (10) |
C9—C8—C13 | 119.01 (14) | C2—N1—C3 | 123.25 (10) |
C10—C9—C8 | 121.40 (16) | C2—N1—H1 | 119.7 (10) |
C10—C9—H9 | 124.1 (12) | C3—N1—H1 | 117.0 (10) |
C8—C9—H9 | 114.5 (12) | C5—O2—H2 | 110.2 (15) |
C9—C10—C11 | 119.79 (15) | | |
| | | |
N1—C3—C4—C5 | 43.62 (16) | C7—C8—C13—C4 | −0.68 (18) |
C14—C3—C4—C5 | −84.79 (14) | C9—C8—C13—C4 | 178.90 (12) |
N1—C3—C4—C13 | −136.88 (11) | C5—C4—C13—C12 | 175.63 (12) |
C14—C3—C4—C13 | 94.72 (13) | C3—C4—C13—C12 | −3.89 (18) |
C13—C4—C5—O2 | −175.59 (11) | C5—C4—C13—C8 | −2.97 (18) |
C3—C4—C5—O2 | 3.92 (18) | C3—C4—C13—C8 | 177.51 (11) |
C13—C4—C5—C6 | 4.87 (19) | N1—C3—C14—C15 | −150.37 (12) |
C3—C4—C5—C6 | −175.62 (12) | C4—C3—C14—C15 | −21.67 (16) |
O2—C5—C6—C7 | 177.43 (13) | N1—C3—C14—C19 | 34.76 (15) |
C4—C5—C6—C7 | −3.0 (2) | C4—C3—C14—C19 | 163.47 (11) |
C5—C6—C7—C8 | −0.8 (2) | C19—C14—C15—C16 | −0.2 (2) |
C6—C7—C8—C9 | −176.96 (14) | C3—C14—C15—C16 | −175.18 (12) |
C6—C7—C8—C13 | 2.6 (2) | C14—C15—C16—C17 | −0.1 (2) |
C7—C8—C9—C10 | 179.31 (15) | C15—C16—C17—C18 | 0.4 (2) |
C13—C8—C9—C10 | −0.3 (2) | C16—C17—C18—C19 | −0.3 (2) |
C8—C9—C10—C11 | 0.4 (3) | C17—C18—C19—C14 | −0.1 (2) |
C9—C10—C11—C12 | −0.5 (3) | C15—C14—C19—C18 | 0.4 (2) |
C10—C11—C12—C13 | 0.5 (3) | C3—C14—C19—C18 | 175.40 (13) |
C11—C12—C13—C8 | −0.4 (2) | O1—C2—N1—C3 | −2.9 (2) |
C11—C12—C13—C4 | −178.98 (14) | C1—C2—N1—C3 | 176.26 (14) |
C7—C8—C13—C12 | −179.36 (12) | C4—C3—N1—C2 | 126.57 (13) |
C9—C8—C13—C12 | 0.23 (18) | C14—C3—N1—C2 | −103.36 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.889 (15) | 2.118 (15) | 2.7052 (16) | 122.8 (13) |
O2—H2···O1i | 0.87 (2) | 1.82 (2) | 2.6807 (16) | 175 (3) |
Symmetry code: (i) x, y+1, z. |