1-[(4-Bromo-phen-yl)(morpholin-4-yl)meth-yl]naphthalen-2-ol.

The title compound, C(21)H(20)BrNO(2), was obtained from a condensation reaction of 4-bromo-benzaldehyde, 2-naphthol and morpholine. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, closing a six-membered ring. The dihedral angle between the naphthalene ring system and the benzene ring is 76.72 (8)°. In addition to the intra-molecular hydrogen bond, the O-H groups of centrosymmetrically related mol-ecules form short inter-molecular H⋯O contacts of 2.59 Å. These mol-ecules are also linked by pairs of C-H⋯O inter-actions, generating an R(2) (2)(14) motif.

Related literature

For applications of Betti-type reactions, see: Lu et al. (2002 ▶); Xu et al. (2004 ▶); Wang et al. (2005 ▶).

Experimental

Crystal data

C21H20BrNO2

M = 398.29

Monoclinic,

a = 11.024 (2) Å

b = 12.119 (2) Å

c = 13.875 (3) Å

β = 104.55 (3)°

V = 1794.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.31 mm−1

T = 293 K

0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.802, T max = 1.000

18164 measured reflections

4108 independent reflections

3021 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.102

S = 1.08

4108 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear (Rigaku, 2005 ▶); data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002620/gk2449sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002620/gk2449Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002620/gk2449Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H20BrNO2	F(000) = 816
Mr = 398.29	Dx = 1.474 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4108 reflections
a = 11.024 (2) Å	θ = 2.7–27.5°
b = 12.119 (2) Å	µ = 2.31 mm−1
c = 13.875 (3) Å	T = 293 K
β = 104.55 (3)°	Prism, colorless
V = 1794.2 (6) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Rigaku Mercury2 diffractometer	4108 independent reflections
Radiation source: fine-focus sealed tube	3021 reflections with I > 2σ(I)
graphite	Rint = 0.059
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ scan	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.802, Tmax = 1.000	l = −17→18
18164 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0357P)2 + 0.6882P] where P = (Fo2 + 2Fc2)/3
4108 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	1.13818 (3)	0.46528 (3)	0.17657 (3)	0.05695 (13)
O1	0.44848 (19)	0.46722 (16)	0.08452 (13)	0.0495 (5)
H1A	0.4865	0.5249	0.0822	0.074*
N1	0.54544 (19)	0.65629 (17)	0.15761 (14)	0.0339 (5)
C15	0.9785 (2)	0.5011 (2)	0.1973 (2)	0.0387 (6)
C16	0.9716 (2)	0.5484 (2)	0.2853 (2)	0.0430 (7)
H16A	1.0439	0.5604	0.3356	0.052*
O2	0.41804 (19)	0.84827 (16)	0.06130 (14)	0.0529 (5)
C17	0.8560 (2)	0.5779 (2)	0.29851 (19)	0.0383 (6)
H17A	0.8513	0.6114	0.3578	0.046*
C5	0.5138 (3)	0.3376 (2)	0.3700 (2)	0.0465 (7)
C1	0.5505 (2)	0.4867 (2)	0.25927 (18)	0.0343 (6)
C11	0.6207 (2)	0.5910 (2)	0.24246 (17)	0.0328 (5)
H11A	0.6352	0.6364	0.3027	0.039*
C10	0.5719 (2)	0.4394 (2)	0.35761 (19)	0.0373 (6)
C9	0.6502 (3)	0.4891 (3)	0.44318 (19)	0.0462 (7)
H9A	0.6889	0.5560	0.4374	0.055*
C12	0.7474 (2)	0.5589 (2)	0.22564 (17)	0.0320 (5)
C3	0.4124 (3)	0.3329 (2)	0.1943 (2)	0.0472 (7)
H3A	0.3587	0.2986	0.1402	0.057*
C14	0.8724 (3)	0.4807 (3)	0.1230 (2)	0.0508 (8)
H14A	0.8780	0.4486	0.0634	0.061*
C21	0.4301 (2)	0.6992 (2)	0.1799 (2)	0.0422 (6)
H21A	0.4517	0.7497	0.2359	0.051*
H21B	0.3823	0.6388	0.1977	0.051*
C18	0.6141 (3)	0.7518 (2)	0.1316 (2)	0.0447 (7)
H18A	0.6905	0.7268	0.1157	0.054*
H18B	0.6370	0.8018	0.1878	0.054*
C6	0.5383 (3)	0.2888 (3)	0.4655 (3)	0.0652 (10)
H6A	0.5012	0.2216	0.4733	0.078*
C13	0.7575 (3)	0.5088 (3)	0.1383 (2)	0.0518 (8)
H13A	0.6852	0.4937	0.0888	0.062*
C2	0.4726 (2)	0.4315 (2)	0.18050 (19)	0.0379 (6)
C4	0.4320 (3)	0.2876 (2)	0.2861 (3)	0.0540 (8)
H4A	0.3910	0.2225	0.2943	0.065*
C20	0.3525 (3)	0.7583 (3)	0.0899 (2)	0.0537 (8)
H20A	0.3291	0.7067	0.0349	0.064*
H20B	0.2761	0.7853	0.1044	0.064*
C19	0.5324 (3)	0.8112 (3)	0.0430 (2)	0.0530 (8)
H19A	0.5778	0.8740	0.0265	0.064*
H19B	0.5140	0.7619	−0.0139	0.064*
C8	0.6695 (3)	0.4395 (3)	0.5347 (2)	0.0603 (9)
H8A	0.7202	0.4741	0.5902	0.072*
C7	0.6148 (4)	0.3382 (3)	0.5461 (3)	0.0701 (11)
H7A	0.6306	0.3047	0.6083	0.084*

	U11	U22	U33	U12	U13	U23
Br1	0.03958 (18)	0.0596 (2)	0.0768 (3)	0.00364 (14)	0.02412 (15)	−0.00697 (16)
O1	0.0537 (12)	0.0564 (12)	0.0335 (10)	−0.0090 (10)	0.0017 (9)	−0.0046 (9)
N1	0.0327 (11)	0.0389 (12)	0.0301 (11)	0.0051 (9)	0.0080 (9)	0.0044 (9)
C15	0.0317 (14)	0.0391 (14)	0.0461 (16)	0.0020 (11)	0.0116 (12)	0.0033 (12)
C16	0.0303 (14)	0.0544 (17)	0.0416 (15)	−0.0049 (12)	0.0041 (12)	−0.0009 (13)
O2	0.0549 (12)	0.0499 (12)	0.0541 (12)	0.0140 (10)	0.0141 (10)	0.0128 (10)
C17	0.0378 (14)	0.0445 (14)	0.0333 (14)	−0.0052 (12)	0.0099 (12)	−0.0055 (12)
C5	0.0515 (17)	0.0402 (15)	0.0567 (18)	0.0131 (13)	0.0305 (15)	0.0087 (14)
C1	0.0313 (13)	0.0378 (14)	0.0345 (14)	0.0051 (11)	0.0097 (11)	0.0022 (11)
C11	0.0334 (13)	0.0392 (14)	0.0246 (12)	0.0019 (11)	0.0051 (10)	−0.0008 (10)
C10	0.0335 (14)	0.0436 (15)	0.0382 (14)	0.0122 (11)	0.0156 (11)	0.0069 (12)
C9	0.0411 (16)	0.0630 (18)	0.0353 (15)	0.0085 (14)	0.0109 (13)	0.0075 (14)
C12	0.0330 (13)	0.0333 (13)	0.0291 (13)	0.0007 (10)	0.0068 (11)	0.0016 (10)
C3	0.0440 (16)	0.0440 (16)	0.0580 (19)	−0.0035 (13)	0.0212 (14)	−0.0132 (14)
C14	0.0433 (16)	0.070 (2)	0.0392 (16)	0.0070 (15)	0.0105 (13)	−0.0146 (14)
C21	0.0397 (15)	0.0441 (15)	0.0454 (16)	0.0060 (12)	0.0157 (12)	0.0023 (13)
C18	0.0428 (16)	0.0471 (16)	0.0471 (16)	0.0020 (13)	0.0168 (13)	0.0111 (13)
C6	0.082 (2)	0.057 (2)	0.072 (2)	0.0237 (18)	0.049 (2)	0.0276 (18)
C13	0.0338 (15)	0.081 (2)	0.0364 (15)	0.0038 (14)	0.0007 (12)	−0.0137 (15)
C2	0.0356 (14)	0.0398 (14)	0.0391 (15)	0.0037 (11)	0.0107 (12)	−0.0026 (12)
C4	0.0603 (19)	0.0344 (15)	0.080 (2)	−0.0028 (14)	0.0423 (18)	−0.0024 (15)
C20	0.0407 (16)	0.0611 (19)	0.0580 (19)	0.0124 (14)	0.0100 (14)	0.0038 (16)
C19	0.0565 (18)	0.0564 (18)	0.0485 (17)	0.0101 (15)	0.0174 (14)	0.0177 (14)
C8	0.0511 (18)	0.095 (3)	0.0367 (16)	0.0188 (18)	0.0151 (14)	0.0153 (16)
C7	0.080 (2)	0.089 (3)	0.052 (2)	0.036 (2)	0.0372 (19)	0.037 (2)

Br1—C15	1.904 (3)	C9—H9A	0.9300
O1—C2	1.362 (3)	C12—C13	1.386 (4)
O1—H1A	0.8200	C3—C4	1.354 (4)
N1—C18	1.477 (3)	C3—C2	1.402 (4)
N1—C21	1.477 (3)	C3—H3A	0.9300
N1—C11	1.487 (3)	C14—C13	1.378 (4)
C15—C16	1.369 (4)	C14—H14A	0.9300
C15—C14	1.373 (4)	C21—C20	1.506 (4)
C16—C17	1.379 (4)	C21—H21A	0.9700
C16—H16A	0.9300	C21—H21B	0.9700
O2—C20	1.418 (4)	C18—C19	1.512 (4)
O2—C19	1.420 (3)	C18—H18A	0.9700
C17—C12	1.379 (3)	C18—H18B	0.9700
C17—H17A	0.9300	C6—C7	1.359 (5)
C5—C6	1.414 (4)	C6—H6A	0.9300
C5—C4	1.417 (4)	C13—H13A	0.9300
C5—C10	1.421 (4)	C4—H4A	0.9300
C1—C2	1.382 (4)	C20—H20A	0.9700
C1—C10	1.443 (4)	C20—H20B	0.9700
C1—C11	1.530 (4)	C19—H19A	0.9700
C11—C12	1.523 (3)	C19—H19B	0.9700
C11—H11A	0.9800	C8—C7	1.394 (5)
C10—C9	1.414 (4)	C8—H8A	0.9300
C9—C8	1.372 (4)	C7—H7A	0.9300
C2—O1—H1A	109.5	N1—C21—H21A	109.8
C18—N1—C21	107.3 (2)	C20—C21—H21A	109.8
C18—N1—C11	113.12 (19)	N1—C21—H21B	109.8
C21—N1—C11	111.10 (19)	C20—C21—H21B	109.8
C16—C15—C14	121.1 (3)	H21A—C21—H21B	108.2
C16—C15—Br1	119.4 (2)	N1—C18—C19	109.5 (2)
C14—C15—Br1	119.4 (2)	N1—C18—H18A	109.8
C15—C16—C17	119.2 (2)	C19—C18—H18A	109.8
C15—C16—H16A	120.4	N1—C18—H18B	109.8
C17—C16—H16A	120.4	C19—C18—H18B	109.8
C20—O2—C19	110.1 (2)	H18A—C18—H18B	108.2
C16—C17—C12	121.3 (2)	C7—C6—C5	121.3 (3)
C16—C17—H17A	119.3	C7—C6—H6A	119.3
C12—C17—H17A	119.3	C5—C6—H6A	119.3
C6—C5—C4	121.5 (3)	C14—C13—C12	121.4 (3)
C6—C5—C10	119.4 (3)	C14—C13—H13A	119.3
C4—C5—C10	119.1 (3)	C12—C13—H13A	119.3
C2—C1—C10	118.5 (2)	O1—C2—C1	123.3 (2)
C2—C1—C11	121.2 (2)	O1—C2—C3	115.0 (2)
C10—C1—C11	120.2 (2)	C1—C2—C3	121.7 (3)
N1—C11—C12	111.41 (19)	C3—C4—C5	121.1 (3)
N1—C11—C1	110.96 (19)	C3—C4—H4A	119.4
C12—C11—C1	109.3 (2)	C5—C4—H4A	119.4
N1—C11—H11A	108.3	O2—C20—C21	112.0 (2)
C12—C11—H11A	108.3	O2—C20—H20A	109.2
C1—C11—H11A	108.3	C21—C20—H20A	109.2
C9—C10—C5	117.8 (2)	O2—C20—H20B	109.2
C9—C10—C1	123.0 (2)	C21—C20—H20B	109.2
C5—C10—C1	119.2 (2)	H20A—C20—H20B	107.9
C8—C9—C10	120.7 (3)	O2—C19—C18	112.3 (2)
C8—C9—H9A	119.6	O2—C19—H19A	109.1
C10—C9—H9A	119.6	C18—C19—H19A	109.1
C17—C12—C13	118.0 (2)	O2—C19—H19B	109.1
C17—C12—C11	120.4 (2)	C18—C19—H19B	109.1
C13—C12—C11	121.6 (2)	H19A—C19—H19B	107.9
C4—C3—C2	120.4 (3)	C9—C8—C7	121.3 (3)
C4—C3—H3A	119.8	C9—C8—H8A	119.3
C2—C3—H3A	119.8	C7—C8—H8A	119.3
C15—C14—C13	118.9 (3)	C6—C7—C8	119.4 (3)
C15—C14—H14A	120.5	C6—C7—H7A	120.3
C13—C14—H14A	120.5	C8—C7—H7A	120.3
N1—C21—C20	109.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.93	2.622 (3)	142
C13—H13A···O1i	0.93	2.53	3.357 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.93	2.622 (3)	142
C13—H13A⋯O1i	0.93	2.53	3.357 (4)	148

Symmetry code: (i) .