6-Bromo-3-hydr-oxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid dimethyl-formamide disolvate.

In the title compound, C(16)H(9)BrO(5)·2C(3)H(7)NO, the chromene ring system is essentially planar. The two dimethyl-formamide solvent mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds to the 6-bromo-3-hydr-oxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid molecules.

Related literature

For related literature, see: Gills et al. (1980 ▶); Liu et al. (2007 ▶); Jin & Xiao (2005 ▶); Kagechika et al. (1989 ▶); Valenti et al. (1998 ▶); Walenta et al. (1991 ▶); Zwaagstra et al. (1996 ▶, 1998a ▶,b ▶).

Experimental

Crystal data

C16H9BrO5·2C3H7NO

M = 507.33

Monoclinic,

a = 10.489 (2) Å

b = 11.470 (2) Å

c = 18.803 (4) Å

β = 92.127 (3)°

V = 2260.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.86 mm−1

T = 294 (2) K

0.49 × 0.38 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.462, T max = 0.742

14295 measured reflections

4203 independent reflections

2889 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 0.99

4203 reflections

294 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson,1996 ▶); ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019454/dn2358sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019454/dn2358Isup2.hkl

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

C16H9BrO5·2C3H7NO	F000 = 1040
Mr = 507.33	Dx = 1.491 Mg m−3
Monoclinic, P2(1)/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3645 reflections
a = 10.489 (2) Å	θ = 2.6–23.5º
b = 11.470 (2) Å	µ = 1.86 mm−1
c = 18.803 (4) Å	T = 294 (2) K
β = 92.127 (3)º	Block, yellow
V = 2260.6 (8) Å3	0.49 × 0.38 × 0.17 mm
Z = 4

Bruker SMART CCD diffractometer	4203 independent reflections
Radiation source: fine-focus sealed tube	2889 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 294(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.462, Tmax = 0.742	k = −13→13
14295 measured reflections	l = −22→22

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) = 0.098	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.6824P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.017
4203 reflections	Δρmax = 0.32 e Å−3
294 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.06013 (3)	0.88028 (2)	0.582768 (19)	0.07113 (15)
O1	−0.0368 (2)	0.44074 (18)	0.65009 (12)	0.0911 (8)
O2	0.06856 (17)	0.31912 (16)	0.58290 (9)	0.0577 (5)
H2A	0.0279	0.2704	0.6046	0.087*
O3	0.24560 (16)	0.40314 (13)	0.50359 (9)	0.0460 (4)
O4	0.41242 (18)	0.68075 (16)	0.41187 (10)	0.0652 (6)
O5	0.49923 (18)	0.46087 (15)	0.38343 (11)	0.0610 (5)
H5	0.5303	0.5237	0.3727	0.091*
C1	0.1082 (2)	0.5216 (2)	0.57023 (13)	0.0439 (6)
C2	0.0684 (2)	0.6327 (2)	0.58763 (14)	0.0517 (7)
H2	0.0041	0.6416	0.6199	0.062*
C3	0.1222 (2)	0.7312 (2)	0.55796 (14)	0.0495 (7)
C4	0.2183 (2)	0.7207 (2)	0.51073 (14)	0.0485 (6)
H4	0.2544	0.7869	0.4912	0.058*
C5	0.2615 (2)	0.6101 (2)	0.49221 (13)	0.0422 (6)
C6	0.2067 (2)	0.5112 (2)	0.52147 (12)	0.0411 (6)
C7	0.3634 (2)	0.5972 (2)	0.44191 (14)	0.0456 (6)
C8	0.4030 (2)	0.4787 (2)	0.42805 (13)	0.0443 (6)
C9	0.3421 (2)	0.3864 (2)	0.45729 (13)	0.0429 (6)
C10	0.0406 (3)	0.4222 (2)	0.60528 (14)	0.0518 (7)
C11	0.3633 (2)	0.2608 (2)	0.44578 (13)	0.0442 (6)
C12	0.4628 (3)	0.2186 (3)	0.40674 (19)	0.0821 (11)
H12	0.5188	0.2708	0.3865	0.099*
C13	0.4800 (4)	0.1012 (3)	0.3976 (2)	0.0944 (13)
H13	0.5482	0.0752	0.3716	0.113*
C14	0.3998 (3)	0.0217 (2)	0.42550 (17)	0.0686 (9)
H14	0.4114	−0.0578	0.4184	0.082*
C15	0.3021 (3)	0.0619 (2)	0.46419 (18)	0.0736 (9)
H15	0.2464	0.0089	0.4839	0.088*
C16	0.2840 (3)	0.1793 (2)	0.47476 (16)	0.0629 (8)
H16	0.2169	0.2041	0.5020	0.075*
N1	−0.2166 (3)	0.1136 (2)	0.71663 (13)	0.0631 (7)
O6	−0.0563 (2)	0.15290 (18)	0.64329 (11)	0.0722 (6)
C17	−0.1516 (3)	0.1828 (3)	0.67549 (16)	0.0626 (8)
H17	−0.1792	0.2595	0.6703	0.075*
C18	−0.3276 (4)	0.1567 (3)	0.7524 (2)	0.0983 (13)
H18A	−0.3072	0.1649	0.8024	0.147*
H18B	−0.3968	0.1026	0.7456	0.147*
H18C	−0.3521	0.2311	0.7329	0.147*
C19	−0.1781 (3)	−0.0070 (3)	0.72818 (18)	0.0840 (10)
H19A	−0.2251	−0.0565	0.6955	0.126*
H19B	−0.1953	−0.0294	0.7761	0.126*
H19C	−0.0885	−0.0147	0.7206	0.126*
N2	0.7254 (2)	0.78411 (18)	0.28823 (12)	0.0554 (6)
O7	0.6435 (2)	0.60874 (17)	0.31631 (12)	0.0773 (7)
C20	0.6539 (3)	0.7141 (3)	0.32545 (16)	0.0642 (8)
H20	0.6076	0.7473	0.3615	0.077*
C21	0.7365 (4)	0.9061 (3)	0.3036 (3)	0.1108 (15)
H21A	0.6909	0.9239	0.3456	0.166*
H21B	0.7012	0.9503	0.2642	0.166*
H21C	0.8248	0.9260	0.3113	0.166*
C22	0.8037 (3)	0.7385 (3)	0.23293 (16)	0.0746 (9)
H22A	0.8853	0.7160	0.2532	0.112*
H22B	0.8151	0.7974	0.1975	0.112*
H22C	0.7626	0.6718	0.2114	0.112*

	U11	U22	U33	U12	U13	U23
Br1	0.0723 (2)	0.04462 (18)	0.0983 (3)	0.00670 (14)	0.02689 (18)	−0.00929 (15)
O1	0.1120 (19)	0.0564 (13)	0.1106 (18)	−0.0065 (12)	0.0794 (16)	−0.0021 (12)
O2	0.0641 (13)	0.0440 (11)	0.0672 (12)	−0.0095 (9)	0.0321 (10)	0.0013 (9)
O3	0.0491 (10)	0.0358 (9)	0.0546 (10)	−0.0028 (7)	0.0219 (8)	0.0004 (7)
O4	0.0696 (14)	0.0428 (11)	0.0860 (14)	−0.0029 (9)	0.0389 (11)	0.0106 (10)
O5	0.0621 (13)	0.0421 (10)	0.0814 (13)	−0.0017 (9)	0.0392 (10)	0.0058 (9)
C1	0.0440 (15)	0.0429 (14)	0.0454 (14)	−0.0045 (11)	0.0098 (12)	0.0000 (11)
C2	0.0483 (16)	0.0522 (16)	0.0557 (16)	−0.0010 (12)	0.0179 (13)	−0.0043 (12)
C3	0.0501 (16)	0.0402 (14)	0.0587 (17)	0.0007 (12)	0.0073 (13)	−0.0050 (12)
C4	0.0486 (16)	0.0375 (13)	0.0600 (17)	−0.0043 (11)	0.0085 (13)	0.0032 (12)
C5	0.0411 (14)	0.0389 (13)	0.0472 (14)	−0.0012 (11)	0.0078 (11)	0.0025 (11)
C6	0.0411 (14)	0.0372 (13)	0.0455 (14)	−0.0011 (11)	0.0080 (11)	−0.0015 (11)
C7	0.0425 (15)	0.0412 (14)	0.0540 (15)	−0.0033 (11)	0.0125 (12)	0.0060 (11)
C8	0.0413 (15)	0.0429 (14)	0.0494 (14)	−0.0025 (11)	0.0131 (12)	0.0040 (11)
C9	0.0401 (14)	0.0432 (13)	0.0460 (14)	−0.0022 (11)	0.0116 (11)	0.0022 (11)
C10	0.0528 (17)	0.0501 (15)	0.0537 (16)	−0.0041 (13)	0.0197 (14)	−0.0009 (12)
C11	0.0448 (15)	0.0383 (13)	0.0500 (15)	−0.0009 (11)	0.0102 (12)	−0.0001 (11)
C12	0.083 (2)	0.0446 (16)	0.123 (3)	−0.0012 (15)	0.061 (2)	0.0002 (17)
C13	0.099 (3)	0.0519 (19)	0.137 (3)	0.0085 (18)	0.070 (3)	−0.0067 (19)
C14	0.079 (2)	0.0396 (16)	0.089 (2)	0.0024 (15)	0.0210 (18)	−0.0071 (15)
C15	0.085 (2)	0.0397 (15)	0.099 (2)	−0.0087 (16)	0.0338 (19)	0.0043 (16)
C16	0.069 (2)	0.0440 (15)	0.078 (2)	−0.0023 (14)	0.0344 (16)	−0.0023 (14)
N1	0.0694 (17)	0.0582 (15)	0.0630 (15)	−0.0122 (12)	0.0213 (13)	0.0075 (11)
O6	0.0710 (15)	0.0588 (12)	0.0889 (15)	−0.0066 (10)	0.0320 (12)	0.0131 (11)
C17	0.064 (2)	0.0532 (17)	0.072 (2)	−0.0080 (15)	0.0209 (16)	0.0106 (15)
C18	0.096 (3)	0.088 (3)	0.114 (3)	−0.014 (2)	0.057 (2)	0.004 (2)
C19	0.104 (3)	0.064 (2)	0.084 (2)	−0.0043 (19)	0.016 (2)	0.0247 (18)
N2	0.0544 (14)	0.0404 (12)	0.0727 (15)	−0.0045 (10)	0.0200 (12)	0.0015 (11)
O7	0.0906 (17)	0.0485 (13)	0.0959 (16)	−0.0178 (10)	0.0453 (13)	−0.0037 (10)
C20	0.065 (2)	0.0550 (18)	0.075 (2)	−0.0054 (15)	0.0276 (16)	−0.0033 (15)
C21	0.114 (3)	0.0420 (18)	0.180 (4)	−0.0070 (19)	0.056 (3)	−0.007 (2)
C22	0.087 (2)	0.072 (2)	0.067 (2)	−0.0156 (17)	0.0320 (18)	−0.0041 (16)

Br1—C3	1.894 (2)	C14—C15	1.359 (4)
O1—C10	1.210 (3)	C14—H14	0.9300
O2—C10	1.293 (3)	C15—C16	1.376 (4)
O2—H2A	0.8200	C15—H15	0.9300
O3—C6	1.351 (3)	C16—H16	0.9300
O3—C9	1.372 (3)	N1—C17	1.316 (3)
O4—C7	1.235 (3)	N1—C18	1.453 (4)
O5—C8	1.352 (3)	N1—C19	1.455 (4)
O5—H5	0.8200	O6—C17	1.236 (3)
C1—C2	1.384 (3)	C17—H17	0.9300
C1—C6	1.412 (3)	C18—H18A	0.9600
C1—C10	1.507 (3)	C18—H18B	0.9600
C2—C3	1.389 (4)	C18—H18C	0.9600
C2—H2	0.9300	C19—H19A	0.9600
C3—C4	1.373 (3)	C19—H19B	0.9600
C4—C5	1.396 (3)	C19—H19C	0.9600
C4—H4	0.9300	N2—C20	1.318 (3)
C5—C6	1.394 (3)	N2—C21	1.433 (4)
C5—C7	1.460 (3)	N2—C22	1.447 (3)
C7—C8	1.447 (3)	O7—C20	1.225 (3)
C8—C9	1.363 (3)	C20—H20	0.9300
C9—C11	1.475 (3)	C21—H21A	0.9600
C11—C16	1.377 (3)	C21—H21B	0.9600
C11—C12	1.386 (4)	C21—H21C	0.9600
C12—C13	1.371 (4)	C22—H22A	0.9600
C12—H12	0.9300	C22—H22B	0.9600
C13—C14	1.359 (4)	C22—H22C	0.9600
C13—H13	0.9300
C10—O2—H2A	109.5	C13—C14—H14	121.0
C6—O3—C9	121.48 (18)	C14—C15—C16	121.4 (3)
C8—O5—H5	109.5	C14—C15—H15	119.3
C2—C1—C6	117.8 (2)	C16—C15—H15	119.3
C2—C1—C10	116.2 (2)	C15—C16—C11	121.2 (3)
C6—C1—C10	126.0 (2)	C15—C16—H16	119.4
C1—C2—C3	121.6 (2)	C11—C16—H16	119.4
C1—C2—H2	119.2	C17—N1—C18	120.6 (3)
C3—C2—H2	119.2	C17—N1—C19	120.9 (3)
C4—C3—C2	120.5 (2)	C18—N1—C19	118.5 (3)
C4—C3—Br1	120.38 (19)	O6—C17—N1	124.5 (3)
C2—C3—Br1	119.14 (19)	O6—C17—H17	117.7
C3—C4—C5	119.6 (2)	N1—C17—H17	117.7
C3—C4—H4	120.2	N1—C18—H18A	109.5
C5—C4—H4	120.2	N1—C18—H18B	109.5
C6—C5—C4	119.9 (2)	H18A—C18—H18B	109.5
C6—C5—C7	119.7 (2)	N1—C18—H18C	109.5
C4—C5—C7	120.4 (2)	H18A—C18—H18C	109.5
O3—C6—C5	121.0 (2)	H18B—C18—H18C	109.5
O3—C6—C1	118.3 (2)	N1—C19—H19A	109.5
C5—C6—C1	120.6 (2)	N1—C19—H19B	109.5
O4—C7—C8	121.3 (2)	H19A—C19—H19B	109.5
O4—C7—C5	123.0 (2)	N1—C19—H19C	109.5
C8—C7—C5	115.7 (2)	H19A—C19—H19C	109.5
O5—C8—C9	120.3 (2)	H19B—C19—H19C	109.5
O5—C8—C7	118.7 (2)	C20—N2—C21	122.1 (3)
C9—C8—C7	120.9 (2)	C20—N2—C22	120.7 (2)
C8—C9—O3	121.0 (2)	C21—N2—C22	117.0 (2)
C8—C9—C11	128.6 (2)	O7—C20—N2	125.2 (3)
O3—C9—C11	110.38 (19)	O7—C20—H20	117.4
O1—C10—O2	123.6 (2)	N2—C20—H20	117.4
O1—C10—C1	120.7 (2)	N2—C21—H21A	109.5
O2—C10—C1	115.7 (2)	N2—C21—H21B	109.5
C16—C11—C12	116.8 (2)	H21A—C21—H21B	109.5
C16—C11—C9	120.6 (2)	N2—C21—H21C	109.5
C12—C11—C9	122.7 (2)	H21A—C21—H21C	109.5
C13—C12—C11	121.0 (3)	H21B—C21—H21C	109.5
C13—C12—H12	119.5	N2—C22—H22A	109.5
C11—C12—H12	119.5	N2—C22—H22B	109.5
C14—C13—C12	121.6 (3)	H22A—C22—H22B	109.5
C14—C13—H13	119.2	N2—C22—H22C	109.5
C12—C13—H13	119.2	H22A—C22—H22C	109.5
C15—C14—C13	118.0 (3)	H22B—C22—H22C	109.5
C15—C14—H14	121.0

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O6	0.82	1.78	2.598 (2)	173
O5—H5···O7	0.82	1.89	2.627 (2)	149
O5—H5···O4	0.82	2.32	2.741 (3)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O6	0.82	1.78	2.598 (2)	173
O5—H5⋯O7	0.82	1.89	2.627 (2)	149
O5—H5⋯O4	0.82	2.32	2.741 (3)	113