Crystal structure of 4,4-dibutyl-2-phenyl-3,4-di-hydro-quinazoline.

In the title compound, C22H28N2, the dihedral angle between the planes of the phenyl ring and the di-hydro-quinazoline ring system (r.m.s. deviation = 0.030 Å) is 24.95 (7)° and both n-butane chains assume all-trans conformations. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into C(4) chains propagating in the [001] direction.

Related literature

For the synthesis of 4,4-dibutyl-2-phenyl-3,4-di­hydro­quin­azo­line, see: Smith et al. (2005 ▶); Plé et al. (1997 ▶). For the crystal structures of related compounds, see Valkonen et al. (2011 ▶); Derabli et al. (2013 ▶).

Experimental

Crystal data

C22H28N2

M = 320.46

Monoclinic,

a = 19.2953 (8) Å

b = 9.9889 (3) Å

c = 9.6341 (4) Å

β = 96.667 (4)°

V = 1844.31 (12) Å3

Z = 4

Cu Kα radiation

μ = 0.51 mm−1

T = 150 K

0.41 × 0.13 × 0.04 mm

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▶) T min = 0.829, T max = 1.000

12894 measured reflections

3657 independent reflections

2866 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.04

3657 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and CHEMDRAW Ultra (Cambridge Soft, 2001 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814020017/hb7281sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814020017/hb7281Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814020017/hb7281Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814020017/hb7281fig1.tif

The asymmetric ubit of the title compound with 50% probability displacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S1600536814020017/hb7281fig2.tif

Packing in the crystal structure showing N—H⋯N contacts as dotted lines with hydrogen atoms omitted for clarity.

CCDC reference: 1022964

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H28N2	F(000) = 696
Mr = 320.46	Dx = 1.154 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 19.2953 (8) Å	Cell parameters from 3898 reflections
b = 9.9889 (3) Å	θ = 4.6–73.6°
c = 9.6341 (4) Å	µ = 0.51 mm−1
β = 96.667 (4)°	T = 150 K
V = 1844.31 (12) Å3	Plate, colourless
Z = 4	0.41 × 0.13 × 0.04 mm

SuperNova, Dual, Cu at zero, Atlas diffractometer	2866 reflections with I > 2σ(I)
ω scans	Rint = 0.043
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	θmax = 73.6°, θmin = 4.6°
Tmin = 0.829, Tmax = 1.000	h = −23→23
12894 measured reflections	k = −12→12
3657 independent reflections	l = −11→11

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.3637P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3657 reflections	Δρmax = 0.23 e Å−3
219 parameters	Δρmin = −0.17 e Å−3

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
C1	0.28102 (8)	0.40404 (13)	0.14783 (14)	0.0259 (3)
C2	0.18929 (7)	0.30261 (13)	0.27980 (14)	0.0246 (3)
C3	0.26279 (8)	0.45814 (13)	0.39845 (15)	0.0272 (3)
C4	0.29777 (8)	0.48405 (13)	0.28214 (15)	0.0273 (3)
C5	0.28292 (9)	0.52724 (14)	0.52321 (16)	0.0314 (3)
H5	0.2592	0.5103	0.6025	0.038*
C6	0.33672 (9)	0.61972 (15)	0.53300 (17)	0.0356 (4)
H6	0.3500	0.6650	0.6187	0.043*
C7	0.37112 (9)	0.64606 (15)	0.41752 (18)	0.0358 (4)
H7	0.4078	0.7099	0.4232	0.043*
C8	0.35142 (8)	0.57829 (15)	0.29334 (17)	0.0326 (3)
H8	0.3750	0.5966	0.2142	0.039*
C9	0.12820 (8)	0.20985 (13)	0.27592 (14)	0.0259 (3)
C10	0.11781 (8)	0.10256 (14)	0.18380 (16)	0.0293 (3)
H10	0.1501	0.0869	0.1183	0.035*
C11	0.06087 (9)	0.01805 (15)	0.18637 (17)	0.0347 (4)
H11	0.0544	−0.0546	0.1225	0.042*
C12	0.01348 (9)	0.03893 (17)	0.28127 (18)	0.0369 (4)
H12	−0.0251	−0.0198	0.2837	0.044*
C13	0.02269 (9)	0.14620 (18)	0.37290 (18)	0.0399 (4)
H13	−0.0099	0.1616	0.4378	0.048*
C14	0.07937 (9)	0.23099 (16)	0.36999 (17)	0.0346 (4)
H14	0.0851	0.3045	0.4328	0.041*
C15	0.26253 (8)	0.49478 (14)	0.01923 (15)	0.0286 (3)
H15A	0.3044	0.5479	0.0049	0.034*
H15B	0.2520	0.4366	−0.0637	0.034*
C16	0.20181 (9)	0.59109 (15)	0.02432 (16)	0.0322 (3)
H16A	0.2107	0.6483	0.1084	0.039*
H16B	0.1586	0.5394	0.0319	0.039*
C17	0.19140 (8)	0.67945 (14)	−0.10553 (16)	0.0309 (3)
H17A	0.2352	0.7288	−0.1141	0.037*
H17B	0.1817	0.6217	−0.1891	0.037*
C18	0.13220 (9)	0.77946 (17)	−0.10306 (19)	0.0410 (4)
H18A	0.0880	0.7313	−0.1029	0.061*
H18B	0.1300	0.8369	−0.1859	0.061*
H18C	0.1404	0.8347	−0.0187	0.061*
C19	0.34439 (8)	0.31704 (14)	0.12029 (15)	0.0284 (3)
H19A	0.3305	0.2605	0.0373	0.034*
H19B	0.3820	0.3773	0.0966	0.034*
C20	0.37407 (8)	0.22668 (15)	0.23908 (16)	0.0322 (3)
H20A	0.3375	0.1632	0.2613	0.039*
H20B	0.3877	0.2818	0.3233	0.039*
C21	0.43742 (9)	0.14803 (16)	0.20321 (18)	0.0380 (4)
H21A	0.4249	0.0997	0.1141	0.046*
H21B	0.4755	0.2115	0.1894	0.046*
C22	0.46367 (11)	0.0478 (2)	0.3163 (2)	0.0534 (5)
H22A	0.4806	0.0958	0.4023	0.080*
H22B	0.5018	−0.0049	0.2851	0.080*
H22C	0.4255	−0.0121	0.3343	0.080*
N1	0.22079 (6)	0.31594 (12)	0.16295 (12)	0.0269 (3)
H1	0.2042	0.2684	0.0897	0.032*
N2	0.20764 (7)	0.36574 (12)	0.39726 (12)	0.0281 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0316 (8)	0.0222 (6)	0.0253 (7)	−0.0012 (5)	0.0088 (6)	0.0013 (5)
C2	0.0291 (7)	0.0207 (6)	0.0248 (7)	0.0044 (5)	0.0060 (5)	0.0031 (5)
C3	0.0328 (8)	0.0205 (6)	0.0285 (7)	0.0035 (5)	0.0049 (6)	0.0009 (5)
C4	0.0322 (7)	0.0201 (6)	0.0297 (7)	0.0024 (5)	0.0045 (6)	0.0022 (5)
C5	0.0408 (9)	0.0265 (7)	0.0273 (7)	0.0023 (6)	0.0054 (6)	−0.0007 (6)
C6	0.0445 (9)	0.0260 (7)	0.0349 (8)	0.0018 (6)	−0.0013 (7)	−0.0062 (6)
C7	0.0369 (9)	0.0247 (7)	0.0456 (9)	−0.0037 (6)	0.0032 (7)	−0.0020 (6)
C8	0.0376 (8)	0.0256 (7)	0.0357 (8)	−0.0009 (6)	0.0089 (7)	0.0010 (6)
C9	0.0297 (7)	0.0240 (6)	0.0243 (7)	0.0022 (5)	0.0049 (6)	0.0050 (5)
C10	0.0344 (8)	0.0264 (7)	0.0287 (7)	0.0016 (6)	0.0104 (6)	0.0019 (5)
C11	0.0389 (9)	0.0254 (7)	0.0404 (9)	−0.0018 (6)	0.0070 (7)	−0.0001 (6)
C12	0.0320 (8)	0.0353 (8)	0.0440 (9)	−0.0029 (6)	0.0068 (7)	0.0066 (7)
C13	0.0338 (9)	0.0490 (10)	0.0398 (9)	−0.0008 (7)	0.0168 (7)	−0.0003 (7)
C14	0.0366 (9)	0.0372 (8)	0.0313 (8)	0.0006 (6)	0.0101 (6)	−0.0039 (6)
C15	0.0349 (8)	0.0257 (7)	0.0265 (7)	−0.0016 (6)	0.0092 (6)	0.0023 (5)
C16	0.0378 (8)	0.0286 (7)	0.0313 (8)	0.0019 (6)	0.0083 (6)	0.0035 (6)
C17	0.0358 (8)	0.0264 (7)	0.0305 (8)	−0.0011 (6)	0.0036 (6)	0.0011 (6)
C18	0.0396 (9)	0.0356 (8)	0.0477 (10)	0.0043 (7)	0.0053 (7)	0.0087 (7)
C19	0.0334 (8)	0.0265 (7)	0.0267 (7)	−0.0005 (6)	0.0094 (6)	0.0009 (5)
C20	0.0380 (8)	0.0292 (7)	0.0301 (8)	0.0036 (6)	0.0075 (6)	0.0020 (6)
C21	0.0387 (9)	0.0322 (8)	0.0443 (9)	0.0047 (7)	0.0095 (7)	0.0024 (7)
C22	0.0478 (11)	0.0497 (11)	0.0628 (12)	0.0166 (9)	0.0060 (9)	0.0133 (9)
N1	0.0345 (7)	0.0247 (6)	0.0227 (6)	−0.0036 (5)	0.0084 (5)	−0.0009 (4)
N2	0.0352 (7)	0.0253 (6)	0.0248 (6)	−0.0012 (5)	0.0079 (5)	−0.0002 (5)

C1—N1	1.4783 (18)	C13—H13	0.9500
C1—C4	1.523 (2)	C14—H14	0.9500
C1—C15	1.5432 (19)	C15—C16	1.521 (2)
C1—C19	1.5480 (19)	C15—H15A	0.9900
C2—N2	1.3079 (19)	C15—H15B	0.9900
C2—N1	1.3466 (18)	C16—C17	1.525 (2)
C2—C9	1.496 (2)	C16—H16A	0.9900
C3—C4	1.398 (2)	C16—H16B	0.9900
C3—C5	1.401 (2)	C17—C18	1.520 (2)
C3—N2	1.4078 (19)	C17—H17A	0.9900
C4—C8	1.394 (2)	C17—H17B	0.9900
C5—C6	1.385 (2)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.385 (2)	C18—H18C	0.9800
C6—H6	0.9500	C19—C20	1.517 (2)
C7—C8	1.389 (2)	C19—H19A	0.9900
C7—H7	0.9500	C19—H19B	0.9900
C8—H8	0.9500	C20—C21	1.526 (2)
C9—C10	1.391 (2)	C20—H20A	0.9900
C9—C14	1.397 (2)	C20—H20B	0.9900
C10—C11	1.388 (2)	C21—C22	1.523 (2)
C10—H10	0.9500	C21—H21A	0.9900
C11—C12	1.382 (2)	C21—H21B	0.9900
C11—H11	0.9500	C22—H22A	0.9800
C12—C13	1.387 (2)	C22—H22B	0.9800
C12—H12	0.9500	C22—H22C	0.9800
C13—C14	1.386 (2)	N1—H1	0.8800
N1—C1—C4	108.69 (11)	C1—C15—H15B	108.1
N1—C1—C15	108.52 (12)	H15A—C15—H15B	107.3
C4—C1—C15	112.35 (11)	C15—C16—C17	111.60 (12)
N1—C1—C19	109.17 (11)	C15—C16—H16A	109.3
C4—C1—C19	110.25 (12)	C17—C16—H16A	109.3
C15—C1—C19	107.80 (11)	C15—C16—H16B	109.3
N2—C2—N1	124.93 (13)	C17—C16—H16B	109.3
N2—C2—C9	116.96 (12)	H16A—C16—H16B	108.0
N1—C2—C9	118.10 (12)	C18—C17—C16	113.28 (13)
C4—C3—C5	119.01 (14)	C18—C17—H17A	108.9
C4—C3—N2	123.35 (13)	C16—C17—H17A	108.9
C5—C3—N2	117.64 (13)	C18—C17—H17B	108.9
C8—C4—C3	119.10 (14)	C16—C17—H17B	108.9
C8—C4—C1	120.17 (13)	H17A—C17—H17B	107.7
C3—C4—C1	120.61 (13)	C17—C18—H18A	109.5
C6—C5—C3	121.19 (14)	C17—C18—H18B	109.5
C6—C5—H5	119.4	H18A—C18—H18B	109.5
C3—C5—H5	119.4	C17—C18—H18C	109.5
C5—C6—C7	119.83 (15)	H18A—C18—H18C	109.5
C5—C6—H6	120.1	H18B—C18—H18C	109.5
C7—C6—H6	120.1	C20—C19—C1	116.19 (12)
C6—C7—C8	119.38 (15)	C20—C19—H19A	108.2
C6—C7—H7	120.3	C1—C19—H19A	108.2
C8—C7—H7	120.3	C20—C19—H19B	108.2
C7—C8—C4	121.49 (14)	C1—C19—H19B	108.2
C7—C8—H8	119.3	H19A—C19—H19B	107.4
C4—C8—H8	119.3	C19—C20—C21	112.19 (12)
C10—C9—C14	118.18 (14)	C19—C20—H20A	109.2
C10—C9—C2	123.21 (12)	C21—C20—H20A	109.2
C14—C9—C2	118.61 (13)	C19—C20—H20B	109.2
C11—C10—C9	120.86 (13)	C21—C20—H20B	109.2
C11—C10—H10	119.6	H20A—C20—H20B	107.9
C9—C10—H10	119.6	C22—C21—C20	112.66 (14)
C12—C11—C10	120.39 (15)	C22—C21—H21A	109.1
C12—C11—H11	119.8	C20—C21—H21A	109.1
C10—C11—H11	119.8	C22—C21—H21B	109.1
C11—C12—C13	119.48 (15)	C20—C21—H21B	109.1
C11—C12—H12	120.3	H21A—C21—H21B	107.8
C13—C12—H12	120.3	C21—C22—H22A	109.5
C14—C13—C12	120.16 (14)	C21—C22—H22B	109.5
C14—C13—H13	119.9	H22A—C22—H22B	109.5
C12—C13—H13	119.9	C21—C22—H22C	109.5
C13—C14—C9	120.92 (15)	H22A—C22—H22C	109.5
C13—C14—H14	119.5	H22B—C22—H22C	109.5
C9—C14—H14	119.5	C2—N1—C1	125.27 (12)
C16—C15—C1	116.92 (12)	C2—N1—H1	117.4
C16—C15—H15A	108.1	C1—N1—H1	117.4
C1—C15—H15A	108.1	C2—N2—C3	116.84 (12)
C16—C15—H15B	108.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.88	2.29	3.1239 (16)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.88	2.29	3.1239 (16)	157

Symmetry code: (i) .