N-(2-Hydroxy­phen­yl)-N′-phenethyl­succinamide

Mol­ecules of the title compound, C₁₈H₂₀N₂O₃, adopt a rod-like shape, probably influenced by N—H...O and O—H...O inter­molecular hydrogen bonds, which also determine the formation of polymeric chains along the glide direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.094
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    -   C16     ..       5.34 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C10     ..       2.96 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: All authors made significant contribution in this work. The idea of synthesis belongs to Lipson. The synthesis, purification and crystallization was performed by Gubarevich, Kustova and Boiko. X-ray diffraction experiment was performed by Konovalova. The analysis of diffraction data was performed by Shishkina and Shishkin.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: XP (Siemens, 1998); software used to prepare material for publication: SHELXTL.

N-(2-Hydroxyphenyl)-N'-phenethylsuccinamide

Crystal data

C18H20N2O3	F(000) = 664
Mr = 312.36	Dx = 1.308 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.630 (4) Å	Cell parameters from 2438 reflections
b = 5.1128 (8) Å	θ = 15–35°
c = 17.326 (4) Å	µ = 0.09 mm^−1
β = 114.17 (2)°	T = 293 K
V = 1586.5 (6) Å^3	Plate, colourless
Z = 4	0.30 × 0.20 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur-3 diffractometer	1954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.0°, θmin = 3.2°
Detector resolution: 16.1827 pixels mm^-1	h = −23→23
ω scans	k = −4→6
9600 measured reflections	l = −20→20
2755 independent reflections

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0589P)^2] where P = (Fo^2 + 2Fc^2)/3
2755 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.14 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.62494 (7)	0.4387 (2)	0.74982 (8)	0.0377 (3)
H1N	0.6018 (8)	0.448 (3)	0.7795 (9)	0.036 (4)*
N2	0.35372 (7)	0.8939 (3)	0.47553 (8)	0.0470 (4)
H2N	0.3588 (8)	0.778 (3)	0.4444 (9)	0.042 (4)*
O1	0.63265 (6)	0.0313 (2)	0.84800 (7)	0.0467 (3)
H1O	0.6332 (11)	−0.109 (5)	0.8729 (12)	0.084 (7)*
O2	0.61856 (6)	0.5334 (2)	0.62020 (6)	0.0522 (3)
O3	0.40800 (6)	1.0848 (2)	0.60360 (6)	0.0451 (3)
C1	0.69068 (8)	0.2853 (3)	0.78053 (8)	0.0355 (3)
C2	0.75168 (8)	0.3432 (3)	0.76358 (9)	0.0463 (4)
H2	0.7496	0.4839	0.7287	0.056*
C3	0.81556 (9)	0.1954 (4)	0.79772 (10)	0.0560 (5)
H3	0.8564	0.2356	0.7858	0.067*
C4	0.81890 (9)	−0.0115 (4)	0.84943 (11)	0.0585 (5)
H4	0.8621	−0.1119	0.8725	0.070*
C5	0.75868 (9)	−0.0714 (3)	0.86738 (10)	0.0491 (4)
H5	0.7614	−0.2112	0.9029	0.059*
C6	0.69417 (8)	0.0752 (3)	0.83289 (8)	0.0359 (3)
C7	0.59387 (7)	0.5581 (3)	0.67425 (8)	0.0355 (3)
C8	0.52791 (8)	0.7285 (3)	0.66093 (9)	0.0425 (4)
H8B	0.5027	0.6626	0.6948	0.051*
H8A	0.5451	0.9043	0.6801	0.051*
C9	0.47368 (8)	0.7381 (3)	0.57006 (8)	0.0412 (4)
H9A	0.4546	0.5630	0.5524	0.049*
H9B	0.5003	0.7912	0.5362	0.049*
C10	0.40872 (8)	0.9192 (3)	0.55142 (9)	0.0364 (3)
C11	0.28660 (8)	1.0523 (3)	0.44343 (10)	0.0505 (4)
H11B	0.2777	1.1125	0.3870	0.061*
H11A	0.2943	1.2051	0.4792	0.061*
C12	0.21921 (9)	0.9092 (3)	0.44003 (11)	0.0567 (4)
H12B	0.2298	0.8371	0.4956	0.068*
H12A	0.2095	0.7639	0.4009	0.068*
C13	0.15013 (9)	1.0748 (3)	0.41318 (10)	0.0485 (4)
C14	0.10585 (10)	1.0701 (4)	0.45743 (12)	0.0654 (5)
H14	0.1178	0.9581	0.5034	0.078*
C15	0.04364 (11)	1.2296 (5)	0.43445 (15)	0.0807 (7)
H15	0.0142	1.2231	0.4649	0.097*
C16	0.02518 (10)	1.3964 (4)	0.36739 (15)	0.0753 (6)
H16	−0.0159	1.5063	0.3530	0.090*
C17	0.06727 (10)	1.4002 (4)	0.32209 (14)	0.0723 (6)
H17	0.0545	1.5110	0.2757	0.087*
C18	0.12902 (9)	1.2402 (3)	0.34440 (12)	0.0609 (5)
H18	0.1571	1.2440	0.3123	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0369 (7)	0.0431 (8)	0.0396 (7)	0.0070 (6)	0.0222 (6)	0.0078 (6)
N2	0.0452 (8)	0.0511 (9)	0.0430 (8)	0.0169 (7)	0.0165 (7)	−0.0008 (7)
O1	0.0482 (7)	0.0380 (7)	0.0641 (7)	0.0026 (5)	0.0332 (6)	0.0111 (5)
O2	0.0487 (6)	0.0742 (8)	0.0394 (6)	0.0201 (6)	0.0237 (5)	0.0058 (5)
O3	0.0517 (6)	0.0389 (6)	0.0493 (6)	0.0110 (5)	0.0253 (5)	−0.0018 (5)
C1	0.0335 (8)	0.0367 (8)	0.0365 (7)	0.0017 (6)	0.0145 (6)	−0.0009 (6)
C2	0.0402 (9)	0.0513 (10)	0.0509 (9)	0.0017 (8)	0.0220 (7)	0.0109 (8)
C3	0.0375 (9)	0.0676 (12)	0.0669 (11)	0.0063 (9)	0.0255 (8)	0.0125 (9)
C4	0.0400 (9)	0.0653 (12)	0.0687 (11)	0.0181 (9)	0.0207 (8)	0.0171 (9)
C5	0.0497 (10)	0.0436 (10)	0.0550 (9)	0.0100 (8)	0.0225 (8)	0.0132 (7)
C6	0.0376 (8)	0.0328 (8)	0.0396 (8)	−0.0019 (7)	0.0181 (6)	−0.0023 (6)
C7	0.0335 (8)	0.0395 (8)	0.0353 (8)	0.0020 (6)	0.0159 (6)	−0.0021 (6)
C8	0.0400 (8)	0.0478 (10)	0.0408 (8)	0.0096 (7)	0.0177 (7)	−0.0015 (7)
C9	0.0425 (9)	0.0466 (9)	0.0375 (8)	0.0117 (7)	0.0194 (7)	0.0026 (7)
C10	0.0420 (8)	0.0366 (8)	0.0382 (8)	0.0059 (7)	0.0241 (7)	0.0057 (7)
C11	0.0414 (9)	0.0519 (10)	0.0555 (10)	0.0145 (8)	0.0171 (8)	0.0078 (8)
C12	0.0507 (10)	0.0509 (11)	0.0668 (11)	0.0061 (8)	0.0223 (8)	0.0087 (8)
C13	0.0371 (8)	0.0466 (10)	0.0574 (10)	−0.0037 (7)	0.0147 (7)	−0.0049 (8)
C14	0.0522 (11)	0.0810 (14)	0.0643 (11)	−0.0062 (10)	0.0252 (9)	0.0000 (10)
C15	0.0510 (12)	0.1075 (19)	0.0925 (16)	−0.0046 (12)	0.0384 (11)	−0.0221 (14)
C16	0.0387 (10)	0.0717 (14)	0.1044 (17)	0.0033 (10)	0.0180 (11)	−0.0133 (13)
C17	0.0452 (10)	0.0678 (13)	0.0921 (14)	0.0071 (10)	0.0159 (10)	0.0150 (11)
C18	0.0471 (10)	0.0600 (12)	0.0768 (12)	0.0066 (9)	0.0265 (9)	0.0118 (10)

Geometric parameters (Å, º)

N1—C7	1.3435 (18)	C8—H8B	0.9700
N1—C1	1.4148 (18)	C8—H8A	0.9700
N1—H1N	0.816 (15)	C9—C10	1.500 (2)
N2—C10	1.3224 (19)	C9—H9A	0.9700
N2—C11	1.4495 (19)	C9—H9B	0.9700
N2—H2N	0.836 (16)	C11—C12	1.492 (2)
O1—C6	1.3551 (17)	C11—H11B	0.9700
O1—H1O	0.84 (2)	C11—H11A	0.9700
O2—C7	1.2246 (15)	C12—C13	1.502 (2)
O3—C10	1.2428 (16)	C12—H12B	0.9700
C1—C2	1.377 (2)	C12—H12A	0.9700
C1—C6	1.3893 (19)	C13—C14	1.375 (2)
C2—C3	1.373 (2)	C13—C18	1.379 (2)
C2—H2	0.9300	C14—C15	1.385 (3)
C3—C4	1.370 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.365 (3)
C4—C5	1.374 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.353 (3)
C5—C6	1.379 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.380 (2)
C7—C8	1.498 (2)	C17—H17	0.9300
C8—C9	1.497 (2)	C18—H18	0.9300
C7—N1—C1	126.78 (12)	C8—C9—H9B	108.5
C7—N1—H1N	116.1 (10)	C10—C9—H9B	108.5
C1—N1—H1N	116.9 (10)	H9A—C9—H9B	107.5
C10—N2—C11	124.79 (14)	O3—C10—N2	122.83 (14)
C10—N2—H2N	116.6 (10)	O3—C10—C9	121.71 (13)
C11—N2—H2N	118.6 (11)	N2—C10—C9	115.44 (12)
C6—O1—H1O	114.7 (14)	N2—C11—C12	113.16 (14)
C2—C1—C6	119.40 (13)	N2—C11—H11B	108.9
C2—C1—N1	122.64 (13)	C12—C11—H11B	108.9
C6—C1—N1	117.89 (12)	N2—C11—H11A	108.9
C3—C2—C1	120.68 (15)	C12—C11—H11A	108.9
C3—C2—H2	119.7	H11B—C11—H11A	107.8
C1—C2—H2	119.7	C11—C12—C13	114.16 (14)
C4—C3—C2	119.81 (15)	C11—C12—H12B	108.7
C4—C3—H3	120.1	C13—C12—H12B	108.7
C2—C3—H3	120.1	C11—C12—H12A	108.7
C3—C4—C5	120.30 (15)	C13—C12—H12A	108.7
C3—C4—H4	119.9	H12B—C12—H12A	107.6
C5—C4—H4	119.9	C14—C13—C18	117.24 (16)
C4—C5—C6	120.20 (15)	C14—C13—C12	120.94 (16)
C4—C5—H5	119.9	C18—C13—C12	121.81 (15)
C6—C5—H5	119.9	C13—C14—C15	120.92 (19)
O1—C6—C5	123.99 (13)	C13—C14—H14	119.5
O1—C6—C1	116.39 (13)	C15—C14—H14	119.5
C5—C6—C1	119.61 (13)	C16—C15—C14	120.55 (19)
O2—C7—N1	122.31 (13)	C16—C15—H15	119.7
O2—C7—C8	122.01 (13)	C14—C15—H15	119.7
N1—C7—C8	115.67 (12)	C17—C16—C15	119.37 (19)
C9—C8—C7	112.24 (11)	C17—C16—H16	120.3
C9—C8—H8B	109.2	C15—C16—H16	120.3
C7—C8—H8B	109.2	C16—C17—C18	120.3 (2)
C9—C8—H8A	109.2	C16—C17—H17	119.9
C7—C8—H8A	109.2	C18—C17—H17	119.9
H8B—C8—H8A	107.9	C13—C18—C17	121.61 (17)
C8—C9—C10	114.98 (11)	C13—C18—H18	119.2
C8—C9—H9A	108.5	C17—C18—H18	119.2
C10—C9—H9A	108.5
C7—N1—C1—C2	36.6 (2)	C7—C8—C9—C10	−176.20 (13)
C7—N1—C1—C6	−146.28 (14)	C11—N2—C10—O3	0.1 (2)
C6—C1—C2—C3	0.1 (2)	C11—N2—C10—C9	−178.44 (14)
N1—C1—C2—C3	177.17 (15)	C8—C9—C10—O3	13.6 (2)
C1—C2—C3—C4	−0.2 (3)	C8—C9—C10—N2	−167.90 (14)
C2—C3—C4—C5	−0.1 (3)	C10—N2—C11—C12	−106.36 (18)
C3—C4—C5—C6	0.5 (3)	N2—C11—C12—C13	175.64 (14)
C4—C5—C6—O1	−179.27 (15)	C11—C12—C13—C14	−132.56 (17)
C4—C5—C6—C1	−0.6 (2)	C11—C12—C13—C18	46.4 (2)
C2—C1—C6—O1	179.04 (13)	C18—C13—C14—C15	−1.3 (3)
N1—C1—C6—O1	1.87 (19)	C12—C13—C14—C15	177.70 (18)
C2—C1—C6—C5	0.3 (2)	C13—C14—C15—C16	−0.3 (3)
N1—C1—C6—C5	−176.90 (13)	C14—C15—C16—C17	1.6 (3)
C1—N1—C7—O2	4.0 (2)	C15—C16—C17—C18	−1.1 (3)
C1—N1—C7—C8	−174.70 (13)	C14—C13—C18—C17	1.8 (3)
O2—C7—C8—C9	31.7 (2)	C12—C13—C18—C17	−177.23 (17)
N1—C7—C8—C9	−149.57 (13)	C16—C17—C18—C13	−0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^i	0.816 (15)	2.224 (15)	2.9615 (17)	150.6 (13)
O1—H1O···O3^ii	0.84 (2)	1.88 (2)	2.6648 (15)	156 (2)
N2—H2N···O2^iii	0.836 (16)	2.094 (17)	2.9254 (18)	173.0 (15)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y−3/2, −z+3/2; (iii) −x+1, −y+1, −z+1.