Crystal structure of 2-meth-oxy-1-nitro-naphthalene.

The asymmetric unit of the title compound, C11H9NO3, contains two mol-ecules, A and B. In mol-ecule A, the dihedral angle between the planes of the naphthalene ring system (r.m.s. deviation = 0.003 Å) and the nitro group is 89.9 (2)°, and the C atom of the meth-oxy group deviates from the naphthyl plane by 0.022 (2) Å. Equivalent data for mol-ecule B are 0.008 Å, 65.9 (2)° and -0.198 (2) Å, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming [100] chains of alternating A and B mol-ecules. Weak aromatic π-π stacking contacts, with a range of centroid-centroid distances from 3.5863 (9) to 3.8048 (9) Å, are also observed.

Related literature

For biological activities of naphthalene derivatives, see: Wright et al. (2000 ▸); Rokade & Sayyed (2009 ▸); Upadhayaya et al. (2010 ▸). For the title compound as an inter­mediate in the synthesis of anti­pyretic drugs, see: Stoylkova et al. (2000 ▸); Govindarajana et al. (2011 ▸); Kirumakki et al. (2004 ▸); Yadav et al. (1998 ▸). For a related structure, see: Wannalerse et al. (2013 ▸).

Experimental

Crystal data

C11H9NO3

M = 203.19

Triclinic,

a = 9.1291 (4) Å

b = 10.2456 (4) Å

c = 10.5215 (4) Å

α = 86.390 (2)°

β = 82.964 (2)°

γ = 85.801 (2)°

V = 972.63 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.39 × 0.32 × 0.24 mm

Data collection

Bruker X8 APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.676, T max = 0.746

34901 measured reflections

5450 independent reflections

3446 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.141

S = 1.04

5450 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015016114/hb7477sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016114/hb7477Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016114/hb7477Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016114/hb7477fig1.tif

A view of the mol­ecule of the title compound, showing displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.

. DOI: 10.1107/S2056989015016114/hb7477fig2.tif

Partial crystal packing for the title compound showing mol­ecules linked by hydrogen bonds as blue dashed lines and π–π contacts between the naphthalene rings (red dashed lines).

CCDC reference: 1421062

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

C11H9NO3	Z = 4
Mr = 203.19	F(000) = 424
Triclinic, P1	Dx = 1.388 Mg m−3
a = 9.1291 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2456 (4) Å	Cell parameters from 3506 reflections
c = 10.5215 (4) Å	θ = 1.7–30.0°
α = 86.390 (2)°	µ = 0.10 mm−1
β = 82.964 (2)°	T = 296 K
γ = 85.801 (2)°	Block, orange
V = 972.63 (7) Å3	0.39 × 0.32 × 0.24 mm

Bruker X8 APEXII CCD diffractometer	5450 independent reflections
Radiation source: fine-focus sealed tube	3446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 29.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.676, Tmax = 0.746	k = −14→14
34901 measured reflections	l = −14→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.2462P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.141	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.20 e Å−3
5450 reflections	Δρmin = −0.15 e Å−3
272 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.011 (2)

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	0.82138 (17)	0.83303 (15)	0.59386 (15)	0.0445 (3)
C2	0.76837 (19)	0.92960 (16)	0.67524 (16)	0.0512 (4)
C3	0.8714 (2)	0.99956 (17)	0.72711 (17)	0.0582 (4)
H3	0.8389	1.0650	0.7832	0.070*
C4	1.0189 (2)	0.97177 (17)	0.69542 (16)	0.0562 (4)
H4	1.0854	1.0201	0.7298	0.067*
C5	1.07461 (18)	0.87266 (15)	0.61254 (15)	0.0464 (4)
C6	0.97310 (17)	0.79982 (14)	0.55904 (14)	0.0416 (3)
C7	1.02802 (19)	0.70018 (16)	0.47545 (16)	0.0515 (4)
H7	0.9625	0.6519	0.4398	0.062*
C8	1.1760 (2)	0.67452 (19)	0.44694 (18)	0.0605 (5)
H8	1.2107	0.6085	0.3920	0.073*
C9	1.2771 (2)	0.7456 (2)	0.49869 (19)	0.0633 (5)
H9	1.3782	0.7266	0.4781	0.076*
C10	1.2280 (2)	0.84240 (19)	0.57914 (18)	0.0580 (5)
H10	1.2961	0.8895	0.6128	0.070*
C11	0.5602 (3)	1.0473 (2)	0.7849 (2)	0.0859 (7)
H11A	0.4542	1.0518	0.7914	0.129*
H11B	0.5951	1.1311	0.7543	0.129*
H11C	0.5912	1.0242	0.8678	0.129*
C12	0.12086 (16)	0.31177 (13)	0.90308 (14)	0.0391 (3)
C13	0.19472 (16)	0.40531 (14)	0.82703 (14)	0.0411 (3)
C14	0.11092 (19)	0.51331 (15)	0.77661 (15)	0.0477 (4)
H14	0.1581	0.5779	0.7242	0.057*
C15	−0.03834 (18)	0.52299 (15)	0.80456 (15)	0.0483 (4)
H15	−0.0915	0.5959	0.7721	0.058*
C16	−0.11572 (17)	0.42663 (14)	0.88090 (14)	0.0424 (3)
C17	−0.03443 (16)	0.31586 (14)	0.93202 (14)	0.0391 (3)
C18	−0.11305 (19)	0.22006 (16)	1.00938 (17)	0.0515 (4)
H18	−0.0618	0.1475	1.0446	0.062*
C19	−0.2632 (2)	0.23339 (18)	1.0326 (2)	0.0612 (5)
H19	−0.3135	0.1690	1.0827	0.073*
C20	−0.34344 (19)	0.34223 (19)	0.9822 (2)	0.0618 (5)
H20	−0.4460	0.3497	0.9990	0.074*
C21	−0.27129 (18)	0.43676 (17)	0.90895 (18)	0.0532 (4)
H21	−0.3251	0.5093	0.8767	0.064*
C22	0.4201 (2)	0.47481 (19)	0.71352 (18)	0.0615 (5)
H22A	0.5244	0.4516	0.7073	0.092*
H22B	0.4010	0.5629	0.7403	0.092*
H22C	0.3862	0.4688	0.6314	0.092*
N1	0.20980 (15)	0.20198 (13)	0.95773 (14)	0.0483 (3)
N2	0.71338 (16)	0.76148 (15)	0.53852 (16)	0.0571 (4)
O1	0.6734 (2)	0.8025 (2)	0.43824 (19)	0.1118 (7)
O2	0.6708 (2)	0.66298 (17)	0.5941 (2)	0.1043 (6)
O3	0.61970 (14)	0.95078 (14)	0.69777 (14)	0.0703 (4)
O4	0.29054 (17)	0.22522 (13)	1.03577 (15)	0.0785 (4)
O5	0.19774 (17)	0.09259 (12)	0.92409 (16)	0.0767 (4)
O6	0.34371 (12)	0.38730 (11)	0.80514 (11)	0.0537 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0446 (8)	0.0428 (8)	0.0464 (8)	−0.0077 (6)	−0.0072 (7)	0.0025 (6)
C2	0.0539 (10)	0.0513 (9)	0.0462 (9)	−0.0005 (7)	−0.0013 (7)	0.0027 (7)
C3	0.0772 (13)	0.0527 (9)	0.0447 (9)	−0.0034 (9)	−0.0046 (9)	−0.0084 (7)
C4	0.0708 (12)	0.0557 (10)	0.0465 (9)	−0.0177 (8)	−0.0179 (8)	−0.0006 (7)
C5	0.0510 (9)	0.0486 (8)	0.0410 (8)	−0.0110 (7)	−0.0117 (7)	0.0069 (7)
C6	0.0441 (8)	0.0415 (7)	0.0393 (8)	−0.0064 (6)	−0.0076 (6)	0.0052 (6)
C7	0.0527 (10)	0.0499 (9)	0.0526 (10)	−0.0041 (7)	−0.0081 (8)	−0.0046 (7)
C8	0.0582 (11)	0.0624 (11)	0.0580 (11)	0.0062 (8)	−0.0016 (8)	−0.0027 (8)
C9	0.0455 (10)	0.0768 (13)	0.0640 (12)	0.0008 (9)	−0.0028 (8)	0.0118 (10)
C10	0.0499 (10)	0.0688 (11)	0.0578 (11)	−0.0170 (8)	−0.0169 (8)	0.0122 (9)
C11	0.0839 (16)	0.0823 (15)	0.0800 (15)	0.0233 (12)	0.0198 (12)	−0.0064 (12)
C12	0.0404 (8)	0.0360 (7)	0.0417 (8)	−0.0007 (6)	−0.0080 (6)	−0.0039 (6)
C13	0.0390 (8)	0.0445 (8)	0.0403 (8)	−0.0033 (6)	−0.0047 (6)	−0.0046 (6)
C14	0.0524 (9)	0.0456 (8)	0.0442 (8)	−0.0048 (7)	−0.0055 (7)	0.0049 (6)
C15	0.0522 (9)	0.0444 (8)	0.0483 (9)	0.0032 (7)	−0.0121 (7)	0.0036 (7)
C16	0.0413 (8)	0.0445 (8)	0.0431 (8)	−0.0009 (6)	−0.0099 (6)	−0.0089 (6)
C17	0.0392 (8)	0.0386 (7)	0.0409 (8)	−0.0042 (6)	−0.0070 (6)	−0.0069 (6)
C18	0.0493 (9)	0.0441 (8)	0.0611 (10)	−0.0087 (7)	−0.0048 (8)	0.0001 (7)
C19	0.0505 (10)	0.0582 (10)	0.0746 (12)	−0.0188 (8)	0.0041 (9)	−0.0067 (9)
C20	0.0370 (9)	0.0710 (12)	0.0785 (13)	−0.0071 (8)	−0.0011 (8)	−0.0203 (10)
C21	0.0411 (9)	0.0570 (10)	0.0636 (11)	0.0021 (7)	−0.0125 (8)	−0.0125 (8)
C22	0.0487 (10)	0.0745 (12)	0.0592 (11)	−0.0146 (9)	0.0053 (8)	0.0020 (9)
N1	0.0435 (7)	0.0412 (7)	0.0595 (8)	−0.0011 (5)	−0.0071 (6)	0.0016 (6)
N2	0.0450 (8)	0.0572 (9)	0.0709 (10)	−0.0085 (6)	−0.0111 (7)	−0.0039 (7)
O1	0.1262 (16)	0.1253 (15)	0.1010 (13)	−0.0526 (12)	−0.0681 (12)	0.0190 (11)
O2	0.1055 (13)	0.0811 (11)	0.1351 (16)	−0.0523 (10)	−0.0365 (11)	0.0232 (10)
O3	0.0542 (8)	0.0768 (9)	0.0753 (9)	0.0099 (6)	0.0049 (6)	−0.0104 (7)
O4	0.0826 (10)	0.0663 (8)	0.0944 (11)	−0.0031 (7)	−0.0500 (9)	0.0107 (7)
O5	0.0839 (10)	0.0403 (7)	0.1082 (12)	0.0091 (6)	−0.0230 (8)	−0.0139 (7)
O6	0.0394 (6)	0.0609 (7)	0.0585 (7)	−0.0050 (5)	−0.0002 (5)	0.0050 (5)

C1—C2	1.372 (2)	C12—N1	1.4678 (19)
C1—C6	1.411 (2)	C13—O6	1.3524 (18)
C1—N2	1.466 (2)	C13—C14	1.412 (2)
C2—O3	1.353 (2)	C14—C15	1.356 (2)
C2—C3	1.404 (3)	C14—H14	0.9300
C3—C4	1.360 (3)	C15—C16	1.408 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.406 (2)	C16—C21	1.412 (2)
C4—H4	0.9300	C16—C17	1.423 (2)
C5—C10	1.418 (2)	C17—C18	1.414 (2)
C5—C6	1.419 (2)	C18—C19	1.361 (2)
C6—C7	1.413 (2)	C18—H18	0.9300
C7—C8	1.358 (2)	C19—C20	1.400 (3)
C7—H7	0.9300	C19—H19	0.9300
C8—C9	1.396 (3)	C20—C21	1.357 (3)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.360 (3)	C21—H21	0.9300
C9—H9	0.9300	C22—O6	1.427 (2)
C10—H10	0.9300	C22—H22A	0.9600
C11—O3	1.424 (2)	C22—H22B	0.9600
C11—H11A	0.9600	C22—H22C	0.9600
C11—H11B	0.9600	N1—O5	1.2129 (17)
C11—H11C	0.9600	N1—O4	1.2136 (18)
C12—C13	1.371 (2)	N2—O1	1.200 (2)
C12—C17	1.411 (2)	N2—O2	1.200 (2)
C2—C1—C6	124.01 (15)	O6—C13—C14	124.40 (14)
C2—C1—N2	117.77 (15)	C12—C13—C14	118.16 (14)
C6—C1—N2	118.21 (14)	C15—C14—C13	120.05 (14)
O3—C2—C1	116.87 (16)	C15—C14—H14	120.0
O3—C2—C3	125.16 (16)	C13—C14—H14	120.0
C1—C2—C3	117.96 (16)	C14—C15—C16	122.34 (14)
C4—C3—C2	120.12 (16)	C14—C15—H15	118.8
C4—C3—H3	119.9	C16—C15—H15	118.8
C2—C3—H3	119.9	C15—C16—C21	122.11 (14)
C3—C4—C5	122.44 (16)	C15—C16—C17	118.92 (14)
C3—C4—H4	118.8	C21—C16—C17	118.97 (14)
C5—C4—H4	118.8	C12—C17—C18	124.80 (14)
C4—C5—C10	123.00 (16)	C12—C17—C16	116.68 (13)
C4—C5—C6	118.74 (15)	C18—C17—C16	118.51 (14)
C10—C5—C6	118.27 (16)	C19—C18—C17	120.38 (16)
C1—C6—C7	124.13 (14)	C19—C18—H18	119.8
C1—C6—C5	116.72 (14)	C17—C18—H18	119.8
C7—C6—C5	119.15 (15)	C18—C19—C20	121.21 (17)
C8—C7—C6	120.33 (16)	C18—C19—H19	119.4
C8—C7—H7	119.8	C20—C19—H19	119.4
C6—C7—H7	119.8	C21—C20—C19	119.91 (16)
C7—C8—C9	121.14 (18)	C21—C20—H20	120.0
C7—C8—H8	119.4	C19—C20—H20	120.0
C9—C8—H8	119.4	C20—C21—C16	121.01 (16)
C10—C9—C8	120.03 (18)	C20—C21—H21	119.5
C10—C9—H9	120.0	C16—C21—H21	119.5
C8—C9—H9	120.0	O6—C22—H22A	109.5
C9—C10—C5	121.09 (17)	O6—C22—H22B	109.5
C9—C10—H10	119.5	H22A—C22—H22B	109.5
C5—C10—H10	119.5	O6—C22—H22C	109.5
O3—C11—H11A	109.5	H22A—C22—H22C	109.5
O3—C11—H11B	109.5	H22B—C22—H22C	109.5
H11A—C11—H11B	109.5	O5—N1—O4	123.26 (14)
O3—C11—H11C	109.5	O5—N1—C12	118.58 (14)
H11A—C11—H11C	109.5	O4—N1—C12	118.15 (13)
H11B—C11—H11C	109.5	O1—N2—O2	122.74 (17)
C13—C12—C17	123.81 (13)	O1—N2—C1	118.59 (15)
C13—C12—N1	117.52 (13)	O2—N2—C1	118.65 (16)
C17—C12—N1	118.66 (13)	C2—O3—C11	118.58 (17)
O6—C13—C12	117.43 (13)	C13—O6—C22	117.88 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5i	0.93	2.57	3.409 (2)	150
C11—H11A···O5ii	0.96	2.60	3.462 (3)	150

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C4H4O5i	0.93	2.57	3.409(2)	150
C11H11AO5ii	0.96	2.60	3.462(3)	150

Symmetry codes: (i) ; (ii) .