3-(4-Meth-oxy-benzo-yl)-6-nitro-coumarin.

In the title coumarin derivative (also known as 2H-chromen-2-one or 2H-1-benzopyran-2-one), C17H11NO6, the coumarin ring system is nearly planar, with a dihedral angle of 3.35 (9)° between the pyrone and the benzene rings. The dihedral angle between the planes formed by the coumarin ring system and the benzene substituent is 54.60 (7)°, clearly showing the non-coplanarity of the whole aromatic system. The crystal studied was a non-merohedral twin; the minor component refined to approximately 0.44.

Related literature

For the synthesis of the title compound, see: Raju et al. (2010 ▶). For examples of the biological activity of coumarin derivatives, see: Borges et al. (2009 ▶), Matos et al. (2011a ▶,b ▶,c ▶), Viña et al. (2012a ▶,b ▶); Vazquez-Rodriguez et al. (2013 ▶).

Experimental

Crystal data

C17H11NO6

M = 325.27

Monoclinic,

a = 8.875 (3) Å

b = 17.266 (5) Å

c = 9.174 (3) Å

β = 95.401 (15)°

V = 1399.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.67 × 0.14 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.604, T max = 0.745

30736 measured reflections

2864 independent reflections

2200 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.126

S = 0.91

2864 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002948/go2080sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002948/go2080Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002948/go2080Isup3.cml

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

C17H11NO6	F(000) = 672
Mr = 325.27	Dx = 1.544 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 8.875 (3) Å	Cell parameters from 1848 reflections
b = 17.266 (5) Å	θ = 2.4–26.2°
c = 9.174 (3) Å	µ = 0.12 mm−1
β = 95.401 (15)°	T = 100 K
V = 1399.6 (7) Å3	Prism, colourless
Z = 4	0.67 × 0.14 × 0.03 mm

Bruker APEXII CCD diffractometer	2864 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ω and phi scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.604, Tmax = 0.745	k = 0→21
30736 measured reflections	l = 0→11

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0871P)2 + 0.3903P] where P = (Fo2 + 2Fc2)/3
2864 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. 1H NMR (250 MHz, DMSO-d6) δ p.p.m. 8.29 (d, J = 3.2 Hz, 1H, H-4), 7.75 (dd, J = 9.8, 3.1 Hz, 1H, H-7), 7.69–7.56 (m, 3H, H-5, o-H-2, o-H-6), 7.04 (d, J = 8.3 Hz, 2H, m-H-3, m-H5), 6.08 (d, J = 9.6 Hz, 1H, H-8), 3.83 (s, 3H, –OMe); 13C NMR (63 MHz, DMSO-d6) δ p.p.m. 192.91, 177.98, 166.65, 162.34, 138.75, 131.40, 130.83, 130.47, 129.32, 128.05, 127.28, 121.24, 120.67, 113.84, 55.61; MS EI m/z (%): 326 ([M+1]+, 25), 325 ([M]+, 93), 190 (34), 135 (100), 92 (27), 77 (37); Elem. Anal. Calcd. for C17H11NO6: C, C, 62.77; H, 3.41; Found: C, 62.72; H, 3.32.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C2	0.0307 (2)	0.13803 (12)	0.5978 (2)	0.0137 (4)
C3	−0.0864 (2)	0.16362 (12)	0.6744 (2)	0.0153 (5)
H3	−0.1256	0.2145	0.6595	0.018*
C4	−0.1455 (2)	0.11473 (12)	0.7723 (2)	0.0164 (5)
H4	−0.2265	0.1310	0.8257	0.020*
C5	−0.0842 (2)	0.04053 (13)	0.7918 (2)	0.0156 (5)
C6	0.0352 (2)	0.01480 (13)	0.7193 (2)	0.0147 (5)
H6	0.0751	−0.0358	0.7364	0.018*
C7	0.0969 (2)	0.06452 (12)	0.6200 (2)	0.0131 (4)
C8	0.2244 (2)	0.04597 (12)	0.5416 (2)	0.0135 (4)
H8	0.2701	−0.0036	0.5544	0.016*
C9	0.2809 (2)	0.09697 (11)	0.4506 (2)	0.0131 (4)
C10	0.2034 (2)	0.17126 (12)	0.4186 (2)	0.0149 (5)
C15	0.4152 (2)	0.07478 (12)	0.3707 (2)	0.0146 (5)
C17	0.5336 (2)	0.13255 (12)	0.3473 (2)	0.0147 (5)
C18	0.5631 (2)	0.19667 (12)	0.4378 (2)	0.0144 (5)
H18	0.5055	0.2041	0.5189	0.017*
C19	0.6746 (2)	0.24980 (13)	0.4121 (2)	0.0154 (5)
H19	0.6941	0.2928	0.4756	0.018*
C20	0.7579 (2)	0.23946 (12)	0.2922 (2)	0.0154 (5)
C21	0.7319 (2)	0.17463 (12)	0.2022 (2)	0.0171 (5)
H21	0.7901	0.1671	0.1216	0.021*
C22	0.6222 (2)	0.12166 (12)	0.2302 (2)	0.0146 (5)
H22	0.6064	0.0773	0.1694	0.018*
C24	0.9071 (3)	0.35368 (12)	0.3471 (2)	0.0205 (5)
H24A	0.9528	0.3331	0.4406	0.031*
H24B	0.8180	0.3847	0.3641	0.031*
H24C	0.9809	0.3862	0.3027	0.031*
N11	−0.1513 (2)	−0.01184 (11)	0.89252 (19)	0.0186 (4)
O1	0.08130 (16)	0.18773 (8)	0.49739 (15)	0.0152 (3)
O12	−0.11434 (19)	−0.08064 (9)	0.89156 (18)	0.0273 (4)
O13	−0.24056 (19)	0.01484 (9)	0.97419 (17)	0.0248 (4)
O14	0.23187 (18)	0.21826 (9)	0.32929 (17)	0.0224 (4)
O16	0.42438 (17)	0.00770 (9)	0.32955 (17)	0.0196 (4)
O23	0.86233 (17)	0.29040 (8)	0.24994 (16)	0.0185 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0131 (10)	0.0141 (10)	0.0138 (10)	−0.0044 (9)	0.0010 (8)	0.0002 (8)
C3	0.0147 (11)	0.0139 (11)	0.0172 (11)	0.0022 (9)	0.0008 (9)	−0.0025 (8)
C4	0.0141 (11)	0.0192 (11)	0.0163 (11)	−0.0001 (9)	0.0030 (9)	−0.0046 (9)
C5	0.0140 (10)	0.0202 (11)	0.0127 (10)	−0.0056 (9)	0.0020 (8)	−0.0014 (9)
C6	0.0145 (11)	0.0150 (11)	0.0143 (11)	−0.0009 (9)	0.0004 (9)	−0.0011 (8)
C7	0.0102 (10)	0.0157 (10)	0.0132 (10)	−0.0015 (9)	0.0003 (8)	−0.0033 (8)
C8	0.0139 (10)	0.0110 (10)	0.0154 (10)	0.0009 (9)	−0.0006 (8)	−0.0031 (8)
C9	0.0120 (10)	0.0137 (11)	0.0140 (10)	−0.0018 (9)	0.0023 (8)	−0.0032 (8)
C10	0.0112 (11)	0.0165 (11)	0.0172 (11)	−0.0016 (9)	0.0034 (9)	−0.0018 (9)
C15	0.0134 (11)	0.0176 (12)	0.0130 (10)	0.0009 (9)	0.0017 (8)	0.0011 (8)
C17	0.0132 (11)	0.0170 (12)	0.0143 (10)	0.0037 (9)	0.0038 (8)	0.0031 (8)
C18	0.0120 (11)	0.0180 (12)	0.0136 (10)	0.0028 (9)	0.0037 (8)	0.0011 (8)
C19	0.0155 (11)	0.0161 (10)	0.0145 (11)	0.0022 (9)	0.0014 (8)	−0.0008 (9)
C20	0.0112 (10)	0.0180 (12)	0.0171 (11)	0.0019 (9)	0.0020 (8)	0.0054 (9)
C21	0.0154 (11)	0.0212 (12)	0.0155 (11)	0.0034 (9)	0.0063 (8)	0.0008 (9)
C22	0.0163 (11)	0.0129 (11)	0.0149 (10)	0.0034 (9)	0.0020 (8)	−0.0015 (8)
C24	0.0198 (12)	0.0183 (11)	0.0232 (12)	−0.0040 (10)	0.0013 (9)	0.0031 (9)
N11	0.0188 (10)	0.0222 (11)	0.0151 (10)	−0.0038 (8)	0.0033 (8)	−0.0001 (8)
O1	0.0138 (8)	0.0141 (7)	0.0183 (8)	0.0015 (6)	0.0047 (6)	0.0019 (6)
O12	0.0319 (10)	0.0213 (9)	0.0304 (10)	−0.0009 (7)	0.0119 (7)	0.0048 (7)
O13	0.0268 (9)	0.0303 (9)	0.0195 (8)	−0.0015 (8)	0.0134 (7)	−0.0017 (7)
O14	0.0203 (9)	0.0209 (8)	0.0271 (9)	0.0003 (7)	0.0076 (7)	0.0086 (7)
O16	0.0204 (8)	0.0160 (8)	0.0234 (9)	0.0007 (7)	0.0070 (7)	−0.0037 (6)
O23	0.0174 (8)	0.0188 (8)	0.0200 (8)	−0.0043 (7)	0.0060 (6)	0.0018 (6)

C2—O1	1.365 (2)	C15—C17	1.479 (3)
C2—C3	1.381 (3)	C17—C18	1.394 (3)
C2—C7	1.405 (3)	C17—C22	1.403 (3)
C3—C4	1.372 (3)	C18—C19	1.386 (3)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.397 (3)	C19—C20	1.393 (3)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.377 (3)	C20—O23	1.361 (3)
C5—N11	1.459 (3)	C20—C21	1.397 (3)
C6—C7	1.400 (3)	C21—C22	1.377 (3)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.433 (3)	C22—H22	0.9500
C8—C9	1.343 (3)	C24—O23	1.442 (3)
C8—H8	0.9500	C24—H24A	0.9800
C9—C10	1.472 (3)	C24—H24B	0.9800
C9—C15	1.506 (3)	C24—H24C	0.9800
C10—O14	1.197 (3)	N11—O13	1.230 (2)
C10—O1	1.387 (3)	N11—O12	1.233 (2)
C15—O16	1.223 (3)
O1—C2—C3	116.95 (18)	C18—C17—C22	118.4 (2)
O1—C2—C7	120.40 (19)	C18—C17—C15	123.04 (19)
C3—C2—C7	122.65 (19)	C22—C17—C15	118.55 (19)
C4—C3—C2	119.25 (19)	C19—C18—C17	121.4 (2)
C4—C3—H3	120.4	C19—C18—H18	119.3
C2—C3—H3	120.4	C17—C18—H18	119.3
C3—C4—C5	118.7 (2)	C18—C19—C20	119.3 (2)
C3—C4—H4	120.7	C18—C19—H19	120.3
C5—C4—H4	120.7	C20—C19—H19	120.3
C6—C5—C4	122.8 (2)	O23—C20—C19	124.6 (2)
C6—C5—N11	118.98 (19)	O23—C20—C21	115.35 (19)
C4—C5—N11	118.18 (19)	C19—C20—C21	120.0 (2)
C5—C6—C7	118.8 (2)	C22—C21—C20	120.1 (2)
C5—C6—H6	120.6	C22—C21—H21	119.9
C7—C6—H6	120.6	C20—C21—H21	119.9
C6—C7—C2	117.68 (19)	C21—C22—C17	120.7 (2)
C6—C7—C8	124.40 (19)	C21—C22—H22	119.6
C2—C7—C8	117.91 (19)	C17—C22—H22	119.6
C9—C8—C7	121.61 (19)	O23—C24—H24A	109.5
C9—C8—H8	119.2	O23—C24—H24B	109.5
C7—C8—H8	119.2	H24A—C24—H24B	109.5
C8—C9—C10	120.03 (19)	O23—C24—H24C	109.5
C8—C9—C15	119.64 (18)	H24A—C24—H24C	109.5
C10—C9—C15	120.09 (18)	H24B—C24—H24C	109.5
O14—C10—O1	116.33 (19)	O13—N11—O12	123.53 (18)
O14—C10—C9	127.0 (2)	O13—N11—C5	118.57 (18)
O1—C10—C9	116.64 (18)	O12—N11—C5	117.90 (18)
O16—C15—C17	121.65 (19)	C2—O1—C10	123.03 (16)
O16—C15—C9	118.01 (19)	C20—O23—C24	117.96 (17)
C17—C15—C9	120.31 (18)
O1—C2—C3—C4	177.38 (18)	O16—C15—C17—C18	−152.9 (2)
C7—C2—C3—C4	−2.6 (3)	C9—C15—C17—C18	25.3 (3)
C2—C3—C4—C5	0.4 (3)	O16—C15—C17—C22	25.9 (3)
C3—C4—C5—C6	1.4 (3)	C9—C15—C17—C22	−155.83 (19)
C3—C4—C5—N11	−177.98 (19)	C22—C17—C18—C19	1.4 (3)
C4—C5—C6—C7	−1.0 (3)	C15—C17—C18—C19	−179.72 (19)
N11—C5—C6—C7	178.44 (18)	C17—C18—C19—C20	0.8 (3)
C5—C6—C7—C2	−1.2 (3)	C18—C19—C20—O23	175.13 (19)
C5—C6—C7—C8	177.66 (19)	C18—C19—C20—C21	−2.1 (3)
O1—C2—C7—C6	−176.97 (17)	O23—C20—C21—C22	−176.26 (18)
C3—C2—C7—C6	3.1 (3)	C19—C20—C21—C22	1.2 (3)
O1—C2—C7—C8	4.1 (3)	C20—C21—C22—C17	1.0 (3)
C3—C2—C7—C8	−175.89 (19)	C18—C17—C22—C21	−2.3 (3)
C6—C7—C8—C9	−178.2 (2)	C15—C17—C22—C21	178.75 (19)
C2—C7—C8—C9	0.6 (3)	C6—C5—N11—O13	168.4 (2)
C7—C8—C9—C10	−5.7 (3)	C4—C5—N11—O13	−12.2 (3)
C7—C8—C9—C15	179.94 (18)	C6—C5—N11—O12	−11.2 (3)
C8—C9—C10—O14	−171.9 (2)	C4—C5—N11—O12	168.27 (19)
C15—C9—C10—O14	2.5 (3)	C3—C2—O1—C10	176.38 (18)
C8—C9—C10—O1	6.1 (3)	C7—C2—O1—C10	−3.6 (3)
C15—C9—C10—O1	−179.58 (17)	O14—C10—O1—C2	176.75 (18)
C8—C9—C15—O16	35.9 (3)	C9—C10—O1—C2	−1.4 (3)
C10—C9—C15—O16	−138.5 (2)	C19—C20—O23—C24	9.7 (3)
C8—C9—C15—C17	−142.4 (2)	C21—C20—O23—C24	−172.89 (18)
C10—C9—C15—C17	43.2 (3)