Intermolecular O—H
O bonding and intramolecular N—H
O hydrogen bonding are effective in the stabilization of the crystal structure of the title compound, C
24H
19NO
2.
Supporting information
CCDC reference: 630516
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.080
- wR factor = 0.150
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.147
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.80 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.38 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT415_ALERT_2_C Short Inter D-H..H-X H1A .. H11 .. 2.14 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 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-AREA; 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]benzamide
top
Crystal data top
C24H19NO2 | F(000) = 1488 |
Mr = 353.40 | Dx = 1.255 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2000 reflections |
a = 9.8517 (17) Å | θ = 2.4–27.1° |
b = 11.3516 (18) Å | µ = 0.08 mm−1 |
c = 33.451 (8) Å | T = 298 K |
V = 3740.9 (12) Å3 | Needle, colorless |
Z = 8 | 0.6 × 0.1 × 0.05 mm |
Data collection top
Stoe IPDS-II diffractometer | 2906 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.147 |
Graphite monochromator | θmax = 27.1°, θmin = 2.4° |
φ? ω? scans | h = −12→12 |
27152 measured reflections | k = −13→14 |
4002 independent reflections | l = −42→42 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | All H-atom parameters refined |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0215P)2 + 2.1712P] where P = (Fo2 + 2Fc2)/3 |
4002 reflections | (Δ/σ)max = 0.002 |
320 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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. |
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.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1004 (3) | 0.2573 (2) | 0.39184 (7) | 0.0458 (6) | |
C2 | −0.0342 (3) | 0.2792 (3) | 0.40515 (9) | 0.0589 (8) | |
H2 | −0.050 (3) | 0.355 (3) | 0.4192 (9) | 0.067 (9)* | |
C3 | −0.1346 (3) | 0.2020 (3) | 0.39715 (9) | 0.0636 (8) | |
H3 | −0.228 (3) | 0.219 (3) | 0.4041 (8) | 0.073 (9)* | |
C4 | −0.1092 (3) | 0.0986 (3) | 0.37490 (8) | 0.0516 (7) | |
C5 | −0.2150 (3) | 0.0198 (4) | 0.36434 (9) | 0.0681 (9) | |
H5 | −0.308 (3) | 0.043 (3) | 0.3729 (9) | 0.074 (9)* | |
C6 | −0.1900 (3) | −0.0775 (3) | 0.34197 (9) | 0.0687 (9) | |
H6 | −0.262 (3) | −0.129 (3) | 0.3353 (8) | 0.062 (9)* | |
C7 | −0.0579 (3) | −0.1017 (3) | 0.32939 (8) | 0.0578 (8) | |
H7 | −0.037 (3) | −0.171 (3) | 0.3140 (8) | 0.064 (9)* | |
C8 | 0.0474 (3) | −0.0293 (2) | 0.33948 (7) | 0.0466 (6) | |
H8 | 0.141 (3) | −0.043 (2) | 0.3295 (7) | 0.046 (7)* | |
C9 | 0.0256 (3) | 0.0741 (2) | 0.36260 (7) | 0.0423 (6) | |
C10 | 0.1329 (3) | 0.1542 (2) | 0.37262 (6) | 0.0389 (5) | |
C11 | 0.2779 (3) | 0.1223 (2) | 0.36075 (7) | 0.0401 (6) | |
H11 | 0.285 (2) | 0.035 (2) | 0.3655 (6) | 0.039 (6)* | |
C12 | 0.4256 (2) | 0.1333 (2) | 0.42038 (7) | 0.0391 (5) | |
C13 | 0.5145 (2) | 0.2098 (2) | 0.44553 (6) | 0.0406 (6) | |
C14 | 0.5928 (3) | 0.1554 (3) | 0.47480 (8) | 0.0587 (8) | |
H14 | 0.588 (3) | 0.071 (3) | 0.4774 (9) | 0.073 (10)* | |
C15 | 0.6771 (4) | 0.2226 (4) | 0.49877 (10) | 0.0791 (11) | |
H15 | 0.730 (4) | 0.181 (4) | 0.5152 (11) | 0.110 (14)* | |
C16 | 0.6845 (4) | 0.3423 (4) | 0.49395 (10) | 0.0833 (12) | |
H16 | 0.741 (4) | 0.391 (3) | 0.5103 (10) | 0.097 (12)* | |
C17 | 0.6063 (4) | 0.3967 (3) | 0.46538 (9) | 0.0707 (9) | |
H17 | 0.607 (3) | 0.479 (3) | 0.4607 (9) | 0.069 (9)* | |
C18 | 0.5215 (3) | 0.3301 (3) | 0.44119 (8) | 0.0528 (7) | |
H18 | 0.467 (3) | 0.372 (3) | 0.4226 (9) | 0.066 (9)* | |
C19 | 0.3126 (3) | 0.1487 (2) | 0.31732 (7) | 0.0464 (6) | |
C20 | 0.2482 (3) | 0.2367 (3) | 0.29638 (8) | 0.0623 (8) | |
H19 | 0.170 (4) | 0.285 (3) | 0.3090 (9) | 0.080 (10)* | |
C21 | 0.2853 (4) | 0.2607 (5) | 0.25682 (9) | 0.0939 (14) | |
H20 | 0.228 (5) | 0.326 (4) | 0.2434 (12) | 0.122 (15)* | |
C22 | 0.3836 (5) | 0.1944 (6) | 0.23874 (11) | 0.1089 (18) | |
H21 | 0.413 (5) | 0.211 (4) | 0.2117 (13) | 0.129 (15)* | |
C23 | 0.4475 (6) | 0.1083 (5) | 0.25901 (14) | 0.1044 (17) | |
H22 | 0.517 (5) | 0.060 (4) | 0.2491 (14) | 0.132 (17)* | |
C24 | 0.4132 (4) | 0.0839 (3) | 0.29857 (11) | 0.0733 (10) | |
H23 | 0.453 (4) | 0.018 (3) | 0.3140 (9) | 0.080 (11)* | |
N1 | 0.3825 (2) | 0.1768 (2) | 0.38602 (6) | 0.0447 (5) | |
H1B | 0.401 (3) | 0.253 (3) | 0.3809 (8) | 0.054 (8)* | |
O1 | 0.1977 (2) | 0.34062 (18) | 0.39802 (6) | 0.0597 (6) | |
H1A | 0.160 (4) | 0.404 (4) | 0.4086 (11) | 0.105 (14)* | |
O2 | 0.3937 (2) | 0.03363 (16) | 0.43208 (5) | 0.0647 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0539 (16) | 0.0419 (14) | 0.0417 (13) | 0.0003 (13) | 0.0074 (12) | 0.0037 (10) |
C2 | 0.061 (2) | 0.0554 (17) | 0.0600 (17) | 0.0077 (16) | 0.0171 (14) | −0.0019 (14) |
C3 | 0.0495 (18) | 0.073 (2) | 0.0680 (19) | 0.0080 (17) | 0.0169 (15) | 0.0027 (16) |
C4 | 0.0426 (15) | 0.0657 (18) | 0.0464 (14) | 0.0010 (14) | 0.0028 (12) | 0.0086 (13) |
C5 | 0.0420 (17) | 0.098 (3) | 0.0640 (19) | −0.0090 (18) | 0.0031 (14) | 0.0033 (18) |
C6 | 0.0549 (19) | 0.089 (2) | 0.0623 (18) | −0.0267 (19) | −0.0085 (15) | −0.0022 (18) |
C7 | 0.0601 (19) | 0.0640 (19) | 0.0493 (16) | −0.0125 (17) | −0.0113 (14) | −0.0021 (14) |
C8 | 0.0448 (15) | 0.0499 (15) | 0.0453 (13) | −0.0016 (13) | −0.0069 (12) | 0.0011 (11) |
C9 | 0.0439 (14) | 0.0487 (14) | 0.0343 (12) | 0.0003 (12) | −0.0025 (10) | 0.0077 (10) |
C10 | 0.0413 (13) | 0.0416 (13) | 0.0337 (11) | 0.0029 (11) | −0.0002 (10) | 0.0043 (10) |
C11 | 0.0405 (14) | 0.0398 (13) | 0.0401 (12) | −0.0022 (12) | −0.0047 (10) | −0.0026 (10) |
C12 | 0.0404 (13) | 0.0389 (12) | 0.0378 (12) | 0.0047 (11) | 0.0016 (10) | −0.0034 (10) |
C13 | 0.0383 (13) | 0.0503 (14) | 0.0333 (11) | −0.0008 (12) | 0.0029 (10) | −0.0027 (10) |
C14 | 0.0580 (19) | 0.068 (2) | 0.0505 (15) | −0.0033 (16) | −0.0094 (13) | 0.0066 (14) |
C15 | 0.078 (2) | 0.104 (3) | 0.0550 (18) | −0.019 (2) | −0.0271 (17) | 0.014 (2) |
C16 | 0.090 (3) | 0.104 (3) | 0.0556 (18) | −0.033 (2) | −0.0229 (18) | −0.0078 (19) |
C17 | 0.089 (3) | 0.064 (2) | 0.0584 (18) | −0.023 (2) | −0.0110 (17) | −0.0080 (16) |
C18 | 0.0639 (19) | 0.0516 (16) | 0.0429 (14) | −0.0045 (15) | −0.0086 (13) | −0.0042 (12) |
C19 | 0.0378 (13) | 0.0604 (17) | 0.0410 (12) | −0.0080 (13) | 0.0001 (11) | −0.0141 (12) |
C20 | 0.0479 (16) | 0.098 (2) | 0.0403 (13) | −0.0026 (18) | −0.0022 (13) | 0.0079 (15) |
C21 | 0.070 (3) | 0.167 (4) | 0.0443 (17) | −0.010 (3) | −0.0050 (17) | 0.021 (2) |
C22 | 0.096 (3) | 0.187 (6) | 0.0437 (19) | −0.028 (4) | 0.012 (2) | −0.014 (3) |
C23 | 0.095 (3) | 0.133 (4) | 0.085 (3) | −0.013 (3) | 0.044 (3) | −0.049 (3) |
C24 | 0.070 (2) | 0.078 (2) | 0.073 (2) | 0.001 (2) | 0.0159 (18) | −0.0222 (19) |
N1 | 0.0481 (13) | 0.0415 (12) | 0.0445 (11) | −0.0072 (11) | −0.0124 (9) | 0.0026 (9) |
O1 | 0.0665 (14) | 0.0407 (10) | 0.0719 (13) | −0.0043 (11) | 0.0168 (10) | −0.0097 (9) |
O2 | 0.0962 (17) | 0.0447 (11) | 0.0533 (11) | −0.0100 (11) | −0.0191 (11) | 0.0027 (9) |
Geometric parameters (Å, º) top
C1—O1 | 1.362 (3) | C13—C18 | 1.375 (4) |
C1—C10 | 1.374 (3) | C13—C14 | 1.391 (4) |
C1—C2 | 1.420 (4) | C14—C15 | 1.383 (5) |
C2—C3 | 1.348 (5) | C14—H14 | 0.96 (3) |
C2—H2 | 0.99 (3) | C15—C16 | 1.371 (5) |
C3—C4 | 1.412 (4) | C15—H15 | 0.89 (4) |
C3—H3 | 0.97 (3) | C16—C17 | 1.374 (5) |
C4—C5 | 1.418 (4) | C16—H16 | 0.95 (4) |
C4—C9 | 1.418 (4) | C17—C18 | 1.387 (4) |
C5—C6 | 1.357 (5) | C17—H17 | 0.95 (3) |
C5—H5 | 1.00 (3) | C18—H18 | 0.95 (3) |
C6—C7 | 1.396 (5) | C19—C20 | 1.375 (4) |
C6—H6 | 0.95 (3) | C19—C24 | 1.384 (4) |
C7—C8 | 1.365 (4) | C20—C21 | 1.399 (4) |
C7—H7 | 0.96 (3) | C20—H19 | 1.04 (3) |
C8—C9 | 1.422 (4) | C21—C22 | 1.366 (7) |
C8—H8 | 0.99 (3) | C21—H20 | 1.03 (4) |
C9—C10 | 1.434 (4) | C22—C23 | 1.346 (7) |
C10—C11 | 1.526 (3) | C22—H21 | 0.97 (4) |
C11—N1 | 1.470 (3) | C23—C24 | 1.393 (6) |
C11—C19 | 1.523 (3) | C23—H22 | 0.94 (5) |
C11—H11 | 1.01 (2) | C24—H23 | 0.99 (3) |
C12—O2 | 1.238 (3) | N1—H1B | 0.89 (3) |
C12—N1 | 1.321 (3) | O1—H1A | 0.89 (4) |
C12—C13 | 1.493 (3) | | |
| | | |
O1—C1—C10 | 119.9 (2) | C18—C13—C12 | 123.2 (2) |
O1—C1—C2 | 119.2 (2) | C14—C13—C12 | 117.6 (2) |
C10—C1—C2 | 120.9 (3) | C15—C14—C13 | 119.7 (3) |
C3—C2—C1 | 120.6 (3) | C15—C14—H14 | 121.9 (19) |
C3—C2—H2 | 122.6 (19) | C13—C14—H14 | 118.4 (19) |
C1—C2—H2 | 116.7 (19) | C16—C15—C14 | 120.7 (3) |
C2—C3—C4 | 121.0 (3) | C16—C15—H15 | 124 (3) |
C2—C3—H3 | 121 (2) | C14—C15—H15 | 115 (3) |
C4—C3—H3 | 118 (2) | C15—C16—C17 | 119.9 (3) |
C3—C4—C5 | 121.7 (3) | C15—C16—H16 | 122 (2) |
C3—C4—C9 | 118.8 (3) | C17—C16—H16 | 118 (2) |
C5—C4—C9 | 119.5 (3) | C16—C17—C18 | 119.9 (3) |
C6—C5—C4 | 121.2 (3) | C16—C17—H17 | 124 (2) |
C6—C5—H5 | 122.5 (19) | C18—C17—H17 | 117 (2) |
C4—C5—H5 | 116.3 (19) | C13—C18—C17 | 120.7 (3) |
C5—C6—C7 | 119.8 (3) | C13—C18—H18 | 122.5 (18) |
C5—C6—H6 | 119.6 (18) | C17—C18—H18 | 116.8 (18) |
C7—C6—H6 | 120.6 (18) | C20—C19—C24 | 119.0 (3) |
C8—C7—C6 | 121.0 (3) | C20—C19—C11 | 121.7 (2) |
C8—C7—H7 | 118 (2) | C24—C19—C11 | 119.2 (3) |
C6—C7—H7 | 121.2 (19) | C19—C20—C21 | 120.2 (3) |
C7—C8—C9 | 121.1 (3) | C19—C20—H19 | 121.2 (18) |
C7—C8—H8 | 121.9 (15) | C21—C20—H19 | 118.6 (18) |
C9—C8—H8 | 116.8 (15) | C22—C21—C20 | 119.8 (4) |
C4—C9—C8 | 117.4 (2) | C22—C21—H20 | 126 (2) |
C4—C9—C10 | 119.9 (2) | C20—C21—H20 | 114 (2) |
C8—C9—C10 | 122.7 (2) | C23—C22—C21 | 120.5 (4) |
C1—C10—C9 | 118.5 (2) | C23—C22—H21 | 118 (3) |
C1—C10—C11 | 122.9 (2) | C21—C22—H21 | 121 (3) |
C9—C10—C11 | 118.6 (2) | C22—C23—C24 | 120.6 (4) |
N1—C11—C19 | 108.0 (2) | C22—C23—H22 | 126 (3) |
N1—C11—C10 | 114.0 (2) | C24—C23—H22 | 113 (3) |
C19—C11—C10 | 114.3 (2) | C19—C24—C23 | 119.9 (4) |
N1—C11—H11 | 105.8 (14) | C19—C24—H23 | 117 (2) |
C19—C11—H11 | 109.2 (13) | C23—C24—H23 | 123 (2) |
C10—C11—H11 | 105.2 (14) | C12—N1—C11 | 124.6 (2) |
O2—C12—N1 | 122.4 (2) | C12—N1—H1B | 117.6 (18) |
O2—C12—C13 | 120.2 (2) | C11—N1—H1B | 115.6 (18) |
N1—C12—C13 | 117.5 (2) | C1—O1—H1A | 109 (3) |
C18—C13—C14 | 119.2 (3) | | |
| | | |
O1—C1—C2—C3 | 175.6 (3) | O2—C12—C13—C18 | −159.7 (3) |
C10—C1—C2—C3 | −3.8 (4) | N1—C12—C13—C18 | 19.5 (4) |
C1—C2—C3—C4 | −1.0 (5) | O2—C12—C13—C14 | 19.9 (4) |
C2—C3—C4—C5 | −176.5 (3) | N1—C12—C13—C14 | −160.9 (2) |
C2—C3—C4—C9 | 3.0 (4) | C18—C13—C14—C15 | −0.6 (5) |
C3—C4—C5—C6 | 178.1 (3) | C12—C13—C14—C15 | 179.8 (3) |
C9—C4—C5—C6 | −1.4 (4) | C13—C14—C15—C16 | −0.1 (6) |
C4—C5—C6—C7 | 0.7 (5) | C14—C15—C16—C17 | 0.8 (6) |
C5—C6—C7—C8 | 0.5 (5) | C15—C16—C17—C18 | −0.8 (6) |
C6—C7—C8—C9 | −1.0 (4) | C14—C13—C18—C17 | 0.5 (4) |
C3—C4—C9—C8 | −178.6 (2) | C12—C13—C18—C17 | −179.9 (3) |
C5—C4—C9—C8 | 0.8 (4) | C16—C17—C18—C13 | 0.2 (5) |
C3—C4—C9—C10 | −0.4 (4) | N1—C11—C19—C20 | −100.5 (3) |
C5—C4—C9—C10 | 179.1 (2) | C10—C11—C19—C20 | 27.4 (3) |
C7—C8—C9—C4 | 0.3 (4) | N1—C11—C19—C24 | 78.3 (3) |
C7—C8—C9—C10 | −177.9 (2) | C10—C11—C19—C24 | −153.7 (3) |
O1—C1—C10—C9 | −173.2 (2) | C24—C19—C20—C21 | −0.6 (5) |
C2—C1—C10—C9 | 6.3 (3) | C11—C19—C20—C21 | 178.3 (3) |
O1—C1—C10—C11 | 5.6 (4) | C19—C20—C21—C22 | 1.5 (6) |
C2—C1—C10—C11 | −174.9 (2) | C20—C21—C22—C23 | −1.7 (7) |
C4—C9—C10—C1 | −4.2 (3) | C21—C22—C23—C24 | 1.0 (8) |
C8—C9—C10—C1 | 174.0 (2) | C20—C19—C24—C23 | −0.2 (5) |
C4—C9—C10—C11 | 177.0 (2) | C11—C19—C24—C23 | −179.0 (3) |
C8—C9—C10—C11 | −4.8 (3) | C22—C23—C24—C19 | 0.0 (7) |
C1—C10—C11—N1 | 26.8 (3) | O2—C12—N1—C11 | 9.5 (4) |
C9—C10—C11—N1 | −154.5 (2) | C13—C12—N1—C11 | −169.7 (2) |
C1—C10—C11—C19 | −98.1 (3) | C19—C11—N1—C12 | −147.0 (2) |
C9—C10—C11—C19 | 80.7 (3) | C10—C11—N1—C12 | 84.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1 | 0.90 (3) | 2.31 (3) | 2.633 (3) | 101 (2) |
O1—H1A···O2i | 0.88 (4) | 1.75 (4) | 2.629 (3) | 173 (4) |
Symmetry code: (i) −x+1/2, y+1/2, z. |