2-Chloro-3-[(2-oxo-2H-chromen-6-yl)amino]-naphthalene-1,4-dione.

In the title compound, C19H10ClNO4, the dihedral angle between the naphtho-quinone and coumarin rings is 48.99 (6)°. In the crystal, mol-ecules are linked by strong N-H⋯O hydrogen bonds into chains with graph-set motif C(6) along [101]. The packing also features π-π stacking inter-actions between naphtho-quinone and coumarin rings [centroid-to-centroid distances = 3.7679 (12) and 3.6180 (13) Å].

Related literature

For related compounds see: Rózsa et al. (1989 ▶); Ito et al. (1993 ▶); Ishikawa et al. (1995 ▶); Padwal et al. (2011 ▶). For reference structural data, see: Ibis & Deniz (2012 ▶); Resende & Gomez (2012 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H10ClNO4

M = 351.73

Monoclinic,

a = 10.9371 (5) Å

b = 10.4462 (5) Å

c = 13.5104 (7) Å

β = 108.533 (5)°

V = 1463.53 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 150 K

0.23 × 0.13 × 0.07 mm

Data collection

Oxford Xcalibur Gemini Ultra diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.947, T max = 1

15281 measured reflections

3527 independent reflections

2714 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.065

S = 0.91

3527 reflections

226 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1217 Friedel pairs

Absolute structure parameter: −0.07 (5)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019922/bx2446sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019922/bx2446Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019922/bx2446Isup3.cml

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

C19H10ClNO4	F(000) = 720
Mr = 351.73	Dx = 1.596 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5237 reflections
a = 10.9371 (5) Å	θ = 2.0–29.5°
b = 10.4462 (5) Å	µ = 0.29 mm−1
c = 13.5104 (7) Å	T = 150 K
β = 108.533 (5)°	Prism, violet
V = 1463.53 (12) Å3	0.23 × 0.13 × 0.07 mm
Z = 4

Oxford Xcalibur Gemini Ultra diffractometer with Atlas detector	3527 independent reflections
Graphite monochromator	2714 reflections with I > 2σ(I)
Detector resolution: 10.4186 pixels mm-1	Rint = 0.055
ω scans	θmax = 28.5°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −14→14
Tmin = 0.947, Tmax = 1	k = −13→13
15281 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.029P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max < 0.001
3527 reflections	Δρmax = 0.23 e Å−3
226 parameters	Δρmin = −0.21 e Å−3
2 restraints	Absolute structure: Flack (1983), 1217 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.07 (5)

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) 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.

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
Cl	0.31971 (5)	0.30204 (5)	0.61162 (4)	0.02411 (12)
O4	0.57743 (16)	−0.02583 (15)	0.22630 (13)	0.0366 (4)
O3	0.39509 (13)	0.03816 (14)	0.24617 (11)	0.0246 (4)
O1	−0.11020 (14)	0.09274 (14)	0.55900 (12)	0.0292 (4)
O2	0.31861 (14)	0.29316 (15)	0.82346 (11)	0.0279 (4)
N1	0.07529 (16)	0.14446 (17)	0.48249 (13)	0.0208 (4)
H1	−0.0048	0.1431	0.4453	0.025*
C2	0.20172 (19)	0.23128 (19)	0.65296 (15)	0.0182 (5)
C3	0.09915 (19)	0.17092 (18)	0.58553 (15)	0.0179 (5)
C14	0.3192 (2)	0.0628 (2)	0.30908 (16)	0.0197 (5)
C9	0.11248 (18)	0.2050 (2)	0.80240 (15)	0.0182 (4)
C1	0.2201 (2)	0.2472 (2)	0.76414 (17)	0.0187 (4)
C11	0.16331 (19)	0.11893 (19)	0.42803 (15)	0.0183 (4)
C10	−0.00065 (19)	0.1522 (2)	0.73331 (16)	0.0192 (5)
C13	0.2008 (2)	0.1182 (2)	0.26179 (16)	0.0214 (5)
H13	0.173	0.1363	0.1891	0.026*
C4	−0.0132 (2)	0.13481 (18)	0.62218 (16)	0.0191 (5)
C12	0.1236 (2)	0.14658 (19)	0.32122 (16)	0.0211 (5)
H12	0.042	0.1856	0.2895	0.025*
C15	0.36188 (19)	0.03463 (19)	0.41469 (17)	0.0195 (5)
C16	0.28168 (19)	0.06194 (19)	0.47438 (16)	0.0202 (5)
H16	0.3085	0.0414	0.5466	0.024*
C19	0.5182 (2)	−0.0122 (2)	0.28635 (19)	0.0269 (5)
C18	0.5609 (2)	−0.0425 (2)	0.39665 (18)	0.0258 (5)
H18	0.6438	−0.0795	0.4265	0.031*
C8	0.1236 (2)	0.2211 (2)	0.90669 (17)	0.0240 (5)
H8	0.1993	0.258	0.9536	0.029*
C5	−0.1001 (2)	0.1138 (2)	0.76989 (17)	0.0243 (5)
H5	−0.1765	0.0775	0.7235	0.029*
C6	−0.0869 (2)	0.1289 (2)	0.87452 (18)	0.0265 (5)
H6	−0.1543	0.1017	0.9	0.032*
C7	0.0230 (2)	0.1829 (2)	0.94223 (17)	0.0264 (5)
H7	0.0301	0.1942	1.0136	0.032*
C17	0.4889 (2)	−0.0209 (2)	0.45813 (18)	0.0249 (5)
H17	0.5209	−0.0419	0.5302	0.03*

	U11	U22	U33	U12	U13	U23
Cl	0.0214 (2)	0.0303 (3)	0.0225 (2)	−0.0092 (3)	0.0095 (2)	−0.0010 (3)
O4	0.0313 (10)	0.0461 (11)	0.0399 (10)	0.0050 (8)	0.0221 (8)	−0.0034 (8)
O3	0.0222 (8)	0.0287 (9)	0.0246 (9)	0.0013 (7)	0.0101 (7)	−0.0018 (6)
O1	0.0234 (9)	0.0360 (10)	0.0286 (9)	−0.0082 (7)	0.0091 (7)	−0.0020 (7)
O2	0.0187 (8)	0.0391 (10)	0.0252 (8)	−0.0062 (7)	0.0060 (7)	−0.0032 (7)
N1	0.0147 (9)	0.0263 (10)	0.0214 (10)	−0.0009 (7)	0.0055 (8)	−0.0011 (7)
C2	0.0175 (11)	0.0185 (12)	0.0225 (12)	−0.0010 (8)	0.0120 (9)	0.0029 (8)
C3	0.0188 (11)	0.0156 (11)	0.0196 (11)	0.0036 (9)	0.0065 (9)	0.0045 (8)
C14	0.0191 (11)	0.0205 (11)	0.0206 (11)	−0.0041 (9)	0.0079 (9)	−0.0025 (9)
C9	0.0186 (11)	0.0159 (10)	0.0226 (11)	0.0040 (9)	0.0099 (9)	0.0033 (9)
C1	0.0152 (10)	0.0172 (11)	0.0231 (11)	0.0033 (8)	0.0053 (9)	0.0011 (8)
C11	0.0190 (10)	0.0176 (11)	0.0199 (11)	−0.0042 (9)	0.0085 (9)	−0.0047 (9)
C10	0.0170 (11)	0.0149 (11)	0.0279 (12)	0.0057 (8)	0.0103 (9)	0.0041 (9)
C13	0.0230 (11)	0.0235 (12)	0.0165 (11)	−0.0028 (9)	0.0045 (9)	−0.0022 (9)
C4	0.0177 (11)	0.0140 (11)	0.0253 (12)	0.0014 (9)	0.0066 (10)	0.0015 (9)
C12	0.0166 (10)	0.0204 (12)	0.0235 (12)	−0.0001 (9)	0.0027 (9)	−0.0007 (9)
C15	0.0160 (11)	0.0161 (11)	0.0261 (12)	−0.0014 (8)	0.0065 (9)	−0.0005 (8)
C16	0.0210 (11)	0.0207 (12)	0.0186 (11)	0.0007 (9)	0.0060 (9)	−0.0004 (8)
C19	0.0231 (12)	0.0208 (12)	0.0390 (14)	0.0007 (10)	0.0127 (11)	−0.0014 (10)
C18	0.0183 (12)	0.0252 (13)	0.0328 (13)	0.0053 (9)	0.0067 (10)	0.0037 (10)
C8	0.0224 (12)	0.0268 (13)	0.0231 (12)	0.0055 (9)	0.0076 (10)	0.0029 (9)
C5	0.0201 (11)	0.0201 (12)	0.0360 (14)	0.0017 (9)	0.0135 (10)	0.0020 (10)
C6	0.0232 (12)	0.0298 (14)	0.0338 (14)	0.0067 (10)	0.0194 (11)	0.0070 (10)
C7	0.0270 (12)	0.0339 (15)	0.0230 (12)	0.0098 (11)	0.0146 (10)	0.0059 (10)
C17	0.0245 (13)	0.0222 (12)	0.0262 (12)	0.0014 (10)	0.0054 (11)	0.0028 (10)

Cl—C2	1.7268 (19)	C10—C5	1.389 (3)
O4—C19	1.197 (2)	C10—C4	1.475 (3)
O3—C19	1.385 (3)	C13—C12	1.370 (3)
O3—C14	1.387 (2)	C13—H13	0.95
O1—C4	1.213 (2)	C12—H12	0.95
O2—C1	1.219 (3)	C15—C16	1.397 (3)
N1—C3	1.361 (2)	C15—C17	1.446 (3)
N1—C11	1.411 (2)	C16—H16	0.95
N1—H1	0.86	C19—C18	1.448 (3)
C2—C3	1.355 (3)	C18—C17	1.333 (3)
C2—C1	1.460 (3)	C18—H18	0.95
C3—C4	1.511 (3)	C8—C7	1.391 (3)
C14—C13	1.376 (3)	C8—H8	0.95
C14—C15	1.385 (3)	C5—C6	1.384 (3)
C9—C8	1.386 (3)	C5—H5	0.95
C9—C10	1.404 (3)	C6—C7	1.379 (3)
C9—C1	1.494 (3)	C6—H6	0.95
C11—C16	1.381 (3)	C7—H7	0.95
C11—C12	1.399 (3)	C17—H17	0.95
C19—O3—C14	121.75 (17)	C13—C12—C11	120.85 (19)
C3—N1—C11	129.15 (18)	C13—C12—H12	119.6
C3—N1—H1	115.4	C11—C12—H12	119.6
C11—N1—H1	115.4	C14—C15—C16	118.94 (18)
C3—C2—C1	123.94 (18)	C14—C15—C17	117.96 (18)
C3—C2—Cl	121.72 (15)	C16—C15—C17	123.1 (2)
C1—C2—Cl	114.29 (15)	C11—C16—C15	119.77 (19)
C2—C3—N1	129.12 (18)	C11—C16—H16	120.1
C2—C3—C4	118.78 (17)	C15—C16—H16	120.1
N1—C3—C4	111.90 (17)	O4—C19—O3	116.6 (2)
C13—C14—C15	121.78 (18)	O4—C19—C18	127.2 (2)
C13—C14—O3	116.84 (18)	O3—C19—C18	116.22 (18)
C15—C14—O3	121.37 (18)	C17—C18—C19	122.9 (2)
C8—C9—C10	119.83 (18)	C17—C18—H18	118.6
C8—C9—C1	119.46 (18)	C19—C18—H18	118.6
C10—C9—C1	120.69 (17)	C9—C8—C7	119.5 (2)
O2—C1—C2	121.67 (19)	C9—C8—H8	120.2
O2—C1—C9	121.19 (19)	C7—C8—H8	120.2
C2—C1—C9	117.14 (18)	C6—C5—C10	119.4 (2)
C16—C11—C12	119.73 (18)	C6—C5—H5	120.3
C16—C11—N1	122.81 (18)	C10—C5—H5	120.3
C12—C11—N1	117.36 (18)	C7—C6—C5	120.7 (2)
C5—C10—C9	120.07 (19)	C7—C6—H6	119.7
C5—C10—C4	119.79 (19)	C5—C6—H6	119.7
C9—C10—C4	120.13 (18)	C6—C7—C8	120.4 (2)
C12—C13—C14	118.92 (19)	C6—C7—H7	119.8
C12—C13—H13	120.5	C8—C7—H7	119.8
C14—C13—H13	120.5	C18—C17—C15	119.8 (2)
O1—C4—C10	122.55 (18)	C18—C17—H17	120.1
O1—C4—C3	118.71 (18)	C15—C17—H17	120.1
C10—C4—C3	118.74 (18)
C1—C2—C3—N1	−176.13 (19)	N1—C3—C4—O1	−2.7 (3)
Cl—C2—C3—N1	6.5 (3)	C2—C3—C4—C10	−7.3 (3)
C1—C2—C3—C4	9.5 (3)	N1—C3—C4—C10	177.40 (17)
Cl—C2—C3—C4	−167.80 (14)	C14—C13—C12—C11	−0.6 (3)
C11—N1—C3—C2	30.9 (3)	C16—C11—C12—C13	−0.2 (3)
C11—N1—C3—C4	−154.41 (19)	N1—C11—C12—C13	−176.49 (18)
C19—O3—C14—C13	177.18 (19)	C13—C14—C15—C16	0.7 (3)
C19—O3—C14—C15	−1.9 (3)	O3—C14—C15—C16	179.77 (18)
C3—C2—C1—O2	174.1 (2)	C13—C14—C15—C17	−178.7 (2)
Cl—C2—C1—O2	−8.4 (3)	O3—C14—C15—C17	0.4 (3)
C3—C2—C1—C9	−6.0 (3)	C12—C11—C16—C15	1.2 (3)
Cl—C2—C1—C9	171.51 (14)	N1—C11—C16—C15	177.35 (18)
C8—C9—C1—O2	1.6 (3)	C14—C15—C16—C11	−1.5 (3)
C10—C9—C1—O2	179.98 (19)	C17—C15—C16—C11	177.8 (2)
C8—C9—C1—C2	−178.30 (18)	C14—O3—C19—O4	−177.49 (19)
C10—C9—C1—C2	0.1 (3)	C14—O3—C19—C18	2.5 (3)
C3—N1—C11—C16	29.8 (3)	O4—C19—C18—C17	178.2 (2)
C3—N1—C11—C12	−154.0 (2)	O3—C19—C18—C17	−1.8 (3)
C8—C9—C10—C5	−1.4 (3)	C10—C9—C8—C7	1.0 (3)
C1—C9—C10—C5	−179.75 (18)	C1—C9—C8—C7	179.39 (19)
C8—C9—C10—C4	179.97 (18)	C9—C10—C5—C6	0.5 (3)
C1—C9—C10—C4	1.6 (3)	C4—C10—C5—C6	179.15 (19)
C15—C14—C13—C12	0.4 (3)	C10—C5—C6—C7	0.8 (3)
O3—C14—C13—C12	−178.74 (18)	C5—C6—C7—C8	−1.2 (3)
C5—C10—C4—O1	3.3 (3)	C9—C8—C7—C6	0.3 (3)
C9—C10—C4—O1	−178.1 (2)	C19—C18—C17—C15	0.4 (3)
C5—C10—C4—C3	−176.81 (17)	C14—C15—C17—C18	0.4 (3)
C9—C10—C4—C3	1.9 (3)	C16—C15—C17—C18	−179.0 (2)
C2—C3—C4—O1	172.59 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.21	3.015 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.21	3.015 (2)	157

Symmetry code: (i) .