8-(2-Phenyl­ethyl­amino)­quinoline

The structure of the title compound, C₁₇H₁₆N₂, (I), comprises twisted mol­ecules that contain a single intramolecular N—H...N hydrogen-bonding interaction. The dihedral angle between the two ring systems is 65.72 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.126
• Data-to-parameter ratio = 17.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

NO COMMENT

S2. Experimental

Crystals of (I) were obtained from Spa Contract Synthesis.

S3. Refinement

All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 (Ar—H) and 0.99 Å (CH₂), except for the amine H atom, which was located on difference syntheses and both positional and thermal parameters refined.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

8-(2-Phenylethylamino)quinoline

Crystal data

C17H16N2	Dx = 1.262 Mg m^−3
Mr = 248.32	Melting point: 330-331.5 K K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.1202 (3) Å	Cell parameters from 11683 reflections
b = 9.9645 (3) Å	θ = 2.9–38.6°
c = 13.8592 (5) Å	µ = 0.08 mm^−1
β = 110.7743 (11)°	T = 150 K
V = 1306.73 (7) Å^3	Plate, colourless
Z = 4	0.30 × 0.15 × 0.08 mm
F(000) = 528

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	2989 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→12
Tmin = 0.978, Tmax = 0.994	l = −17→18
18654 measured 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0736P)^2] where P = (Fo^2 + 2Fc^2)/3
2989 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.2752 (0.0044) x + 7.4657 (0.0035) y + 2.7323 (0.0067) z = 1.7749 (0.0007)

* 0.0012 (0.0008) N1 * 0.0030 (0.0009) C2 * -0.0029 (0.0010) C3 * -0.0011 (0.0009) C4 * 0.0051 (0.0008) C10 * -0.0053 (0.0008) C9 0.0138 (0.0020) C5 - 0.0204 (0.0023) C6 - 0.0581 (0.0022) C7 - 0.0344 (0.0018) C8

Rms deviation of fitted atoms = 0.0035

- 3.4507 (0.0048) x + 2.9921 (0.0050) y + 13.2196 (0.0022) z = 4.8858 (0.0015)

Angle to previous plane (with approximate e.s.d.) = 65.72 (0.04)

* 0.0025 (0.0009) C14 * -0.0071 (0.0009) C15 * 0.0039 (0.0009) C16 * 0.0039 (0.0009) C17 * -0.0084 (0.0009) C18 * 0.0052 (0.0009) C19

Rms deviation of fitted atoms = 0.0055

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

	x	y	z	Uiso*/Ueq
N1	0.02455 (10)	0.19291 (10)	0.07554 (8)	0.0333 (3)
C2	−0.03832 (15)	0.26763 (14)	−0.00655 (10)	0.0402 (4)
H2	−0.1150	0.3226	−0.0065	0.050*
C3	0.00107 (15)	0.27090 (15)	−0.09371 (11)	0.0434 (4)
H3	−0.0484	0.3262	−0.1510	0.054*
C4	0.11133 (14)	0.19373 (14)	−0.09507 (10)	0.0395 (4)
H4	0.1396	0.1947	−0.1535	0.049*
C5	0.29936 (15)	0.02972 (13)	−0.00452 (11)	0.0366 (3)
H5	0.3344	0.0291	−0.0597	0.046*
C6	0.36030 (14)	−0.04891 (14)	0.08017 (11)	0.0388 (4)
H6	0.4378	−0.1045	0.0830	0.048*
C7	0.31163 (13)	−0.04997 (13)	0.16325 (11)	0.0356 (3)
H7	0.3552	−0.1074	0.2205	0.045*
C8	0.20115 (13)	0.03150 (12)	0.16259 (10)	0.0298 (3)
C9	0.13443 (12)	0.11497 (12)	0.07400 (10)	0.0287 (3)
C10	0.18326 (13)	0.11239 (12)	−0.00945 (9)	0.0313 (3)
N11	0.15190 (12)	0.03852 (11)	0.24255 (8)	0.0351 (3)
H11	0.0637 (17)	0.0787 (14)	0.2254 (11)	0.050 (4)*
C12	0.20238 (14)	−0.04938 (14)	0.33069 (10)	0.0362 (3)
H121	0.3063	−0.0411	0.3630	0.045*
H122	0.1800	−0.1435	0.3079	0.045*
C13	0.13455 (13)	−0.01480 (15)	0.40963 (10)	0.0379 (3)
H131	0.1855	−0.0632	0.4746	0.047*
H132	0.1461	0.0825	0.4245	0.047*
C14	−0.02005 (13)	−0.04922 (12)	0.37568 (9)	0.0297 (3)
C15	−0.06201 (14)	−0.17757 (13)	0.39305 (10)	0.0339 (3)
H15	0.0076	−0.2435	0.4250	0.042*
C16	−0.20329 (14)	−0.20992 (13)	0.36433 (10)	0.0354 (3)
H16	−0.2301	−0.2973	0.3777	0.044*
C17	−0.30593 (14)	−0.11632 (13)	0.31635 (10)	0.0349 (3)
H17	−0.4031	−0.1389	0.2967	0.044*
C18	−0.26632 (14)	0.01069 (13)	0.29701 (10)	0.0336 (3)
H18	−0.3363	0.0752	0.2628	0.042*
C19	−0.12446 (13)	0.04375 (12)	0.32759 (10)	0.0319 (3)
H19	−0.0982	0.1319	0.3153	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0295 (6)	0.0370 (6)	0.0349 (6)	0.0009 (5)	0.0132 (5)	−0.0003 (5)
C2	0.0374 (7)	0.0439 (8)	0.0392 (8)	0.0036 (6)	0.0134 (6)	0.0034 (7)
C3	0.0487 (9)	0.0460 (8)	0.0344 (8)	−0.0007 (7)	0.0132 (7)	0.0068 (6)
C4	0.0484 (8)	0.0421 (8)	0.0334 (8)	−0.0125 (7)	0.0210 (7)	−0.0039 (6)
C5	0.0383 (7)	0.0393 (7)	0.0413 (8)	−0.0096 (6)	0.0253 (7)	−0.0109 (6)
C6	0.0294 (7)	0.0446 (8)	0.0480 (9)	−0.0011 (6)	0.0208 (6)	−0.0098 (6)
C7	0.0296 (7)	0.0416 (8)	0.0372 (8)	0.0015 (6)	0.0136 (6)	−0.0018 (6)
C8	0.0256 (6)	0.0357 (7)	0.0298 (7)	−0.0037 (5)	0.0119 (5)	−0.0061 (5)
C9	0.0255 (6)	0.0310 (6)	0.0314 (7)	−0.0065 (5)	0.0125 (5)	−0.0057 (5)
C10	0.0331 (7)	0.0318 (7)	0.0321 (7)	−0.0116 (5)	0.0155 (6)	−0.0086 (5)
N11	0.0330 (6)	0.0458 (7)	0.0308 (6)	0.0095 (5)	0.0163 (5)	0.0049 (5)
C12	0.0304 (7)	0.0479 (8)	0.0303 (7)	0.0044 (6)	0.0106 (6)	0.0031 (6)
C13	0.0319 (7)	0.0560 (9)	0.0250 (7)	−0.0022 (6)	0.0090 (6)	−0.0007 (6)
C14	0.0327 (7)	0.0388 (7)	0.0189 (6)	0.0015 (6)	0.0108 (5)	−0.0020 (5)
C15	0.0413 (8)	0.0333 (7)	0.0266 (7)	0.0068 (6)	0.0114 (6)	0.0026 (5)
C16	0.0462 (8)	0.0306 (7)	0.0295 (7)	−0.0045 (6)	0.0135 (6)	−0.0006 (5)
C17	0.0332 (7)	0.0420 (7)	0.0299 (7)	−0.0032 (6)	0.0118 (6)	−0.0030 (6)
C18	0.0352 (7)	0.0366 (7)	0.0301 (7)	0.0070 (6)	0.0129 (6)	0.0016 (6)
C19	0.0399 (7)	0.0299 (6)	0.0283 (7)	0.0000 (5)	0.0152 (6)	0.0013 (5)

Geometric parameters (Å, º)

N1—C2	1.3192 (16)	N11—H11	0.929 (15)
N1—C9	1.3626 (16)	C12—C13	1.5231 (18)
C2—C3	1.400 (2)	C12—H121	0.9900
C2—H2	0.9500	C12—H122	0.9900
C3—C4	1.361 (2)	C13—C14	1.5048 (17)
C3—H3	0.9500	C13—H131	0.9900
C4—C10	1.4079 (18)	C13—H132	0.9900
C4—H4	0.9500	C14—C19	1.3854 (18)
C5—C6	1.363 (2)	C14—C15	1.3952 (18)
C5—C10	1.4166 (19)	C15—C16	1.3795 (19)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.4038 (19)	C16—C17	1.3788 (18)
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.3791 (17)	C17—C18	1.3822 (18)
C7—H7	0.9500	C17—H17	0.9500
C8—N11	1.3686 (17)	C18—C19	1.3848 (18)
C8—C9	1.4378 (18)	C18—H18	0.9500
C9—C10	1.4099 (17)	C19—H19	0.9500
N11—C12	1.4413 (16)
C2—N1—C9	117.05 (12)	N11—C12—C13	110.90 (11)
N1—C2—C3	124.01 (13)	N11—C12—H121	109.5
N1—C2—H2	118.0	C13—C12—H121	109.5
C3—C2—H2	118.0	N11—C12—H122	109.5
C4—C3—C2	118.98 (13)	C13—C12—H122	109.5
C4—C3—H3	120.5	H121—C12—H122	108.0
C2—C3—H3	120.5	C14—C13—C12	114.04 (11)
C3—C4—C10	119.68 (13)	C14—C13—H131	108.7
C3—C4—H4	120.2	C12—C13—H131	108.7
C10—C4—H4	120.2	C14—C13—H132	108.7
C6—C5—C10	119.33 (12)	C12—C13—H132	108.7
C6—C5—H5	120.3	H131—C13—H132	107.6
C10—C5—H5	120.3	C19—C14—C15	117.97 (12)
C5—C6—C7	121.83 (12)	C19—C14—C13	121.94 (12)
C5—C6—H6	119.1	C15—C14—C13	120.09 (12)
C7—C6—H6	119.1	C16—C15—C14	120.81 (12)
C8—C7—C6	120.64 (13)	C16—C15—H15	119.6
C8—C7—H7	119.7	C14—C15—H15	119.6
C6—C7—H7	119.7	C17—C16—C15	120.50 (12)
N11—C8—C7	123.50 (12)	C17—C16—H16	119.7
N11—C8—C9	117.79 (11)	C15—C16—H16	119.7
C7—C8—C9	118.70 (12)	C16—C17—C18	119.49 (12)
N1—C9—C10	123.28 (11)	C16—C17—H17	120.3
N1—C9—C8	117.06 (11)	C18—C17—H17	120.3
C10—C9—C8	119.66 (11)	C17—C18—C19	119.93 (12)
C4—C10—C9	117.00 (12)	C17—C18—H18	120.0
C4—C10—C5	123.19 (12)	C19—C18—H18	120.0
C9—C10—C5	119.81 (12)	C18—C19—C14	121.28 (12)
C8—N11—C12	122.26 (11)	C18—C19—H19	119.4
C8—N11—H11	114.1 (10)	C14—C19—H19	119.4
C12—N11—H11	119.9 (10)
C9—N1—C2—C3	0.08 (19)	C8—C9—C10—C5	−1.26 (17)
N1—C2—C3—C4	−0.5 (2)	C6—C5—C10—C4	−178.09 (12)
C2—C3—C4—C10	0.1 (2)	C6—C5—C10—C9	1.56 (18)
C10—C5—C6—C7	−0.29 (19)	C7—C8—N11—C12	−6.45 (19)
C5—C6—C7—C8	−1.3 (2)	C9—C8—N11—C12	174.23 (11)
C6—C7—C8—N11	−177.72 (12)	C8—N11—C12—C13	177.33 (11)
C6—C7—C8—C9	1.58 (18)	N11—C12—C13—C14	70.24 (15)
C2—N1—C9—C10	0.73 (17)	C12—C13—C14—C19	−93.80 (15)
C2—N1—C9—C8	−178.79 (11)	C12—C13—C14—C15	86.71 (14)
N11—C8—C9—N1	−1.42 (16)	C19—C14—C15—C16	−0.86 (18)
C7—C8—C9—N1	179.23 (11)	C13—C14—C15—C16	178.66 (12)
N11—C8—C9—C10	179.04 (11)	C14—C15—C16—C17	1.01 (19)
C7—C8—C9—C10	−0.31 (17)	C15—C16—C17—C18	0.05 (19)
C3—C4—C10—C9	0.65 (18)	C16—C17—C18—C19	−1.22 (19)
C3—C4—C10—C5	−179.69 (12)	C17—C18—C19—C14	1.38 (19)
N1—C9—C10—C4	−1.10 (17)	C15—C14—C19—C18	−0.33 (19)
C8—C9—C10—C4	178.41 (10)	C13—C14—C19—C18	−179.84 (11)
N1—C9—C10—C5	179.23 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···N1	0.929 (15)	2.277 (15)	2.6961 (15)	106.8 (12)