N-[(2-Hydroxy­naphthalen-1-yl)(phen­yl)meth­yl]benzamide

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.

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

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

Crystal data

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) Å^3	Needle, colorless
Z = 8	0.6 × 0.1 × 0.05 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	All H-atom parameters refined
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0215P)^2 + 2.1712P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O2^i	0.88 (4)	1.75 (4)	2.629 (3)	173 (4)

Symmetry code: (i) −x+1/2, y+1/2, z.