Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
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, C24H19NO2.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046526/xu2150sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046526/xu2150Isup2.hkl
Contains datablock I

CCDC reference: 630516

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Computing details top

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
C24H19NO2F(000) = 1488
Mr = 353.40Dx = 1.255 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2000 reflections
a = 9.8517 (17) Åθ = 2.4–27.1°
b = 11.3516 (18) ŵ = 0.08 mm1
c = 33.451 (8) ÅT = 298 K
V = 3740.9 (12) Å3Needle, colorless
Z = 80.6 × 0.1 × 0.05 mm
Data collection top
Stoe IPDS-II
diffractometer
2906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.147
Graphite monochromatorθmax = 27.1°, θmin = 2.4°
φ? ω? scansh = 1212
27152 measured reflectionsk = 1314
4002 independent reflectionsl = 4242
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150All 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 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
C10.1004 (3)0.2573 (2)0.39184 (7)0.0458 (6)
C20.0342 (3)0.2792 (3)0.40515 (9)0.0589 (8)
H20.050 (3)0.355 (3)0.4192 (9)0.067 (9)*
C30.1346 (3)0.2020 (3)0.39715 (9)0.0636 (8)
H30.228 (3)0.219 (3)0.4041 (8)0.073 (9)*
C40.1092 (3)0.0986 (3)0.37490 (8)0.0516 (7)
C50.2150 (3)0.0198 (4)0.36434 (9)0.0681 (9)
H50.308 (3)0.043 (3)0.3729 (9)0.074 (9)*
C60.1900 (3)0.0775 (3)0.34197 (9)0.0687 (9)
H60.262 (3)0.129 (3)0.3353 (8)0.062 (9)*
C70.0579 (3)0.1017 (3)0.32939 (8)0.0578 (8)
H70.037 (3)0.171 (3)0.3140 (8)0.064 (9)*
C80.0474 (3)0.0293 (2)0.33948 (7)0.0466 (6)
H80.141 (3)0.043 (2)0.3295 (7)0.046 (7)*
C90.0256 (3)0.0741 (2)0.36260 (7)0.0423 (6)
C100.1329 (3)0.1542 (2)0.37262 (6)0.0389 (5)
C110.2779 (3)0.1223 (2)0.36075 (7)0.0401 (6)
H110.285 (2)0.035 (2)0.3655 (6)0.039 (6)*
C120.4256 (2)0.1333 (2)0.42038 (7)0.0391 (5)
C130.5145 (2)0.2098 (2)0.44553 (6)0.0406 (6)
C140.5928 (3)0.1554 (3)0.47480 (8)0.0587 (8)
H140.588 (3)0.071 (3)0.4774 (9)0.073 (10)*
C150.6771 (4)0.2226 (4)0.49877 (10)0.0791 (11)
H150.730 (4)0.181 (4)0.5152 (11)0.110 (14)*
C160.6845 (4)0.3423 (4)0.49395 (10)0.0833 (12)
H160.741 (4)0.391 (3)0.5103 (10)0.097 (12)*
C170.6063 (4)0.3967 (3)0.46538 (9)0.0707 (9)
H170.607 (3)0.479 (3)0.4607 (9)0.069 (9)*
C180.5215 (3)0.3301 (3)0.44119 (8)0.0528 (7)
H180.467 (3)0.372 (3)0.4226 (9)0.066 (9)*
C190.3126 (3)0.1487 (2)0.31732 (7)0.0464 (6)
C200.2482 (3)0.2367 (3)0.29638 (8)0.0623 (8)
H190.170 (4)0.285 (3)0.3090 (9)0.080 (10)*
C210.2853 (4)0.2607 (5)0.25682 (9)0.0939 (14)
H200.228 (5)0.326 (4)0.2434 (12)0.122 (15)*
C220.3836 (5)0.1944 (6)0.23874 (11)0.1089 (18)
H210.413 (5)0.211 (4)0.2117 (13)0.129 (15)*
C230.4475 (6)0.1083 (5)0.25901 (14)0.1044 (17)
H220.517 (5)0.060 (4)0.2491 (14)0.132 (17)*
C240.4132 (4)0.0839 (3)0.29857 (11)0.0733 (10)
H230.453 (4)0.018 (3)0.3140 (9)0.080 (11)*
N10.3825 (2)0.1768 (2)0.38602 (6)0.0447 (5)
H1B0.401 (3)0.253 (3)0.3809 (8)0.054 (8)*
O10.1977 (2)0.34062 (18)0.39802 (6)0.0597 (6)
H1A0.160 (4)0.404 (4)0.4086 (11)0.105 (14)*
O20.3937 (2)0.03363 (16)0.43208 (5)0.0647 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0539 (16)0.0419 (14)0.0417 (13)0.0003 (13)0.0074 (12)0.0037 (10)
C20.061 (2)0.0554 (17)0.0600 (17)0.0077 (16)0.0171 (14)0.0019 (14)
C30.0495 (18)0.073 (2)0.0680 (19)0.0080 (17)0.0169 (15)0.0027 (16)
C40.0426 (15)0.0657 (18)0.0464 (14)0.0010 (14)0.0028 (12)0.0086 (13)
C50.0420 (17)0.098 (3)0.0640 (19)0.0090 (18)0.0031 (14)0.0033 (18)
C60.0549 (19)0.089 (2)0.0623 (18)0.0267 (19)0.0085 (15)0.0022 (18)
C70.0601 (19)0.0640 (19)0.0493 (16)0.0125 (17)0.0113 (14)0.0021 (14)
C80.0448 (15)0.0499 (15)0.0453 (13)0.0016 (13)0.0069 (12)0.0011 (11)
C90.0439 (14)0.0487 (14)0.0343 (12)0.0003 (12)0.0025 (10)0.0077 (10)
C100.0413 (13)0.0416 (13)0.0337 (11)0.0029 (11)0.0002 (10)0.0043 (10)
C110.0405 (14)0.0398 (13)0.0401 (12)0.0022 (12)0.0047 (10)0.0026 (10)
C120.0404 (13)0.0389 (12)0.0378 (12)0.0047 (11)0.0016 (10)0.0034 (10)
C130.0383 (13)0.0503 (14)0.0333 (11)0.0008 (12)0.0029 (10)0.0027 (10)
C140.0580 (19)0.068 (2)0.0505 (15)0.0033 (16)0.0094 (13)0.0066 (14)
C150.078 (2)0.104 (3)0.0550 (18)0.019 (2)0.0271 (17)0.014 (2)
C160.090 (3)0.104 (3)0.0556 (18)0.033 (2)0.0229 (18)0.0078 (19)
C170.089 (3)0.064 (2)0.0584 (18)0.023 (2)0.0110 (17)0.0080 (16)
C180.0639 (19)0.0516 (16)0.0429 (14)0.0045 (15)0.0086 (13)0.0042 (12)
C190.0378 (13)0.0604 (17)0.0410 (12)0.0080 (13)0.0001 (11)0.0141 (12)
C200.0479 (16)0.098 (2)0.0403 (13)0.0026 (18)0.0022 (13)0.0079 (15)
C210.070 (3)0.167 (4)0.0443 (17)0.010 (3)0.0050 (17)0.021 (2)
C220.096 (3)0.187 (6)0.0437 (19)0.028 (4)0.012 (2)0.014 (3)
C230.095 (3)0.133 (4)0.085 (3)0.013 (3)0.044 (3)0.049 (3)
C240.070 (2)0.078 (2)0.073 (2)0.001 (2)0.0159 (18)0.0222 (19)
N10.0481 (13)0.0415 (12)0.0445 (11)0.0072 (11)0.0124 (9)0.0026 (9)
O10.0665 (14)0.0407 (10)0.0719 (13)0.0043 (11)0.0168 (10)0.0097 (9)
O20.0962 (17)0.0447 (11)0.0533 (11)0.0100 (11)0.0191 (11)0.0027 (9)
Geometric parameters (Å, º) top
C1—O11.362 (3)C13—C181.375 (4)
C1—C101.374 (3)C13—C141.391 (4)
C1—C21.420 (4)C14—C151.383 (5)
C2—C31.348 (5)C14—H140.96 (3)
C2—H20.99 (3)C15—C161.371 (5)
C3—C41.412 (4)C15—H150.89 (4)
C3—H30.97 (3)C16—C171.374 (5)
C4—C51.418 (4)C16—H160.95 (4)
C4—C91.418 (4)C17—C181.387 (4)
C5—C61.357 (5)C17—H170.95 (3)
C5—H51.00 (3)C18—H180.95 (3)
C6—C71.396 (5)C19—C201.375 (4)
C6—H60.95 (3)C19—C241.384 (4)
C7—C81.365 (4)C20—C211.399 (4)
C7—H70.96 (3)C20—H191.04 (3)
C8—C91.422 (4)C21—C221.366 (7)
C8—H80.99 (3)C21—H201.03 (4)
C9—C101.434 (4)C22—C231.346 (7)
C10—C111.526 (3)C22—H210.97 (4)
C11—N11.470 (3)C23—C241.393 (6)
C11—C191.523 (3)C23—H220.94 (5)
C11—H111.01 (2)C24—H230.99 (3)
C12—O21.238 (3)N1—H1B0.89 (3)
C12—N11.321 (3)O1—H1A0.89 (4)
C12—C131.493 (3)
O1—C1—C10119.9 (2)C18—C13—C12123.2 (2)
O1—C1—C2119.2 (2)C14—C13—C12117.6 (2)
C10—C1—C2120.9 (3)C15—C14—C13119.7 (3)
C3—C2—C1120.6 (3)C15—C14—H14121.9 (19)
C3—C2—H2122.6 (19)C13—C14—H14118.4 (19)
C1—C2—H2116.7 (19)C16—C15—C14120.7 (3)
C2—C3—C4121.0 (3)C16—C15—H15124 (3)
C2—C3—H3121 (2)C14—C15—H15115 (3)
C4—C3—H3118 (2)C15—C16—C17119.9 (3)
C3—C4—C5121.7 (3)C15—C16—H16122 (2)
C3—C4—C9118.8 (3)C17—C16—H16118 (2)
C5—C4—C9119.5 (3)C16—C17—C18119.9 (3)
C6—C5—C4121.2 (3)C16—C17—H17124 (2)
C6—C5—H5122.5 (19)C18—C17—H17117 (2)
C4—C5—H5116.3 (19)C13—C18—C17120.7 (3)
C5—C6—C7119.8 (3)C13—C18—H18122.5 (18)
C5—C6—H6119.6 (18)C17—C18—H18116.8 (18)
C7—C6—H6120.6 (18)C20—C19—C24119.0 (3)
C8—C7—C6121.0 (3)C20—C19—C11121.7 (2)
C8—C7—H7118 (2)C24—C19—C11119.2 (3)
C6—C7—H7121.2 (19)C19—C20—C21120.2 (3)
C7—C8—C9121.1 (3)C19—C20—H19121.2 (18)
C7—C8—H8121.9 (15)C21—C20—H19118.6 (18)
C9—C8—H8116.8 (15)C22—C21—C20119.8 (4)
C4—C9—C8117.4 (2)C22—C21—H20126 (2)
C4—C9—C10119.9 (2)C20—C21—H20114 (2)
C8—C9—C10122.7 (2)C23—C22—C21120.5 (4)
C1—C10—C9118.5 (2)C23—C22—H21118 (3)
C1—C10—C11122.9 (2)C21—C22—H21121 (3)
C9—C10—C11118.6 (2)C22—C23—C24120.6 (4)
N1—C11—C19108.0 (2)C22—C23—H22126 (3)
N1—C11—C10114.0 (2)C24—C23—H22113 (3)
C19—C11—C10114.3 (2)C19—C24—C23119.9 (4)
N1—C11—H11105.8 (14)C19—C24—H23117 (2)
C19—C11—H11109.2 (13)C23—C24—H23123 (2)
C10—C11—H11105.2 (14)C12—N1—C11124.6 (2)
O2—C12—N1122.4 (2)C12—N1—H1B117.6 (18)
O2—C12—C13120.2 (2)C11—N1—H1B115.6 (18)
N1—C12—C13117.5 (2)C1—O1—H1A109 (3)
C18—C13—C14119.2 (3)
O1—C1—C2—C3175.6 (3)O2—C12—C13—C18159.7 (3)
C10—C1—C2—C33.8 (4)N1—C12—C13—C1819.5 (4)
C1—C2—C3—C41.0 (5)O2—C12—C13—C1419.9 (4)
C2—C3—C4—C5176.5 (3)N1—C12—C13—C14160.9 (2)
C2—C3—C4—C93.0 (4)C18—C13—C14—C150.6 (5)
C3—C4—C5—C6178.1 (3)C12—C13—C14—C15179.8 (3)
C9—C4—C5—C61.4 (4)C13—C14—C15—C160.1 (6)
C4—C5—C6—C70.7 (5)C14—C15—C16—C170.8 (6)
C5—C6—C7—C80.5 (5)C15—C16—C17—C180.8 (6)
C6—C7—C8—C91.0 (4)C14—C13—C18—C170.5 (4)
C3—C4—C9—C8178.6 (2)C12—C13—C18—C17179.9 (3)
C5—C4—C9—C80.8 (4)C16—C17—C18—C130.2 (5)
C3—C4—C9—C100.4 (4)N1—C11—C19—C20100.5 (3)
C5—C4—C9—C10179.1 (2)C10—C11—C19—C2027.4 (3)
C7—C8—C9—C40.3 (4)N1—C11—C19—C2478.3 (3)
C7—C8—C9—C10177.9 (2)C10—C11—C19—C24153.7 (3)
O1—C1—C10—C9173.2 (2)C24—C19—C20—C210.6 (5)
C2—C1—C10—C96.3 (3)C11—C19—C20—C21178.3 (3)
O1—C1—C10—C115.6 (4)C19—C20—C21—C221.5 (6)
C2—C1—C10—C11174.9 (2)C20—C21—C22—C231.7 (7)
C4—C9—C10—C14.2 (3)C21—C22—C23—C241.0 (8)
C8—C9—C10—C1174.0 (2)C20—C19—C24—C230.2 (5)
C4—C9—C10—C11177.0 (2)C11—C19—C24—C23179.0 (3)
C8—C9—C10—C114.8 (3)C22—C23—C24—C190.0 (7)
C1—C10—C11—N126.8 (3)O2—C12—N1—C119.5 (4)
C9—C10—C11—N1154.5 (2)C13—C12—N1—C11169.7 (2)
C1—C10—C11—C1998.1 (3)C19—C11—N1—C12147.0 (2)
C9—C10—C11—C1980.7 (3)C10—C11—N1—C1284.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O10.90 (3)2.31 (3)2.633 (3)101 (2)
O1—H1A···O2i0.88 (4)1.75 (4)2.629 (3)173 (4)
Symmetry code: (i) x+1/2, y+1/2, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds