2,2'-(Quinoxaline-2,3-di-yl)diphenol dimethyl-formamide solvate.

In the title compound, C(20)H(14)N(2)O(2)·C(3)H(7)NO, the quinoxaline ring forms dihedral angles of 64.9 (2) and 30.9 (2)° with the two substituted benzene rings, which are themselves inclined at 58.4 (2)°. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds.

Related literature

For details of cyanide-catalysed cyclizations via aldimine coupling, see: Reich et al. (2004 ▶).

Experimental

Crystal data

C20H14N2O2·C3H7NO

M = 387.43

Orthorhombic,

a = 9.759 (2) Å

b = 10.672 (2) Å

c = 19.049 (4) Å

V = 1983.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.980, T max = 0.983

11593 measured reflections

4322 independent reflections

3434 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.102

S = 1.05

4322 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054385/sj2713sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054385/sj2713Isup2.hkl

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

C20H14N2O2·C3H7NO	F(000) = 816
Mr = 387.43	Dx = 1.297 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4283 reflections
a = 9.759 (2) Å	θ = 2.2–25.9°
b = 10.672 (2) Å	µ = 0.09 mm−1
c = 19.049 (4) Å	T = 298 K
V = 1983.9 (7) Å3	Block, yellow
Z = 4	0.23 × 0.21 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	4322 independent reflections
Radiation source: fine-focus sealed tube	3434 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.980, Tmax = 0.983	k = −13→10
11593 measured reflections	l = −24→19

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) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.0554P] where P = (Fo2 + 2Fc2)/3
4322 reflections	(Δ/σ)max = 0.001
266 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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 > 2sigma(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
N1	0.87527 (15)	0.67113 (14)	0.14671 (8)	0.0496 (3)
N2	0.61529 (14)	0.78228 (13)	0.14710 (8)	0.0494 (4)
N3	0.22105 (17)	0.28969 (17)	0.15246 (8)	0.0639 (4)
O1	1.13645 (14)	0.73589 (16)	0.15603 (8)	0.0771 (4)
H1	1.0673	0.6979	0.1681	0.116*
O2	0.83600 (16)	1.05141 (12)	0.16631 (7)	0.0695 (4)
H2	0.8792	1.1162	0.1731	0.104*
O3	0.00473 (16)	0.23971 (15)	0.18290 (9)	0.0795 (5)
C1	0.76781 (19)	0.61476 (16)	0.18052 (9)	0.0483 (4)
C2	0.63779 (19)	0.66962 (16)	0.18002 (9)	0.0486 (4)
C3	0.5287 (2)	0.61110 (19)	0.21599 (11)	0.0639 (5)
H3	0.4419	0.6472	0.2163	0.077*
C4	0.5521 (3)	0.5016 (2)	0.25004 (11)	0.0711 (6)
H4	0.4808	0.4635	0.2744	0.085*
C5	0.6807 (2)	0.4452 (2)	0.24920 (11)	0.0721 (6)
H5	0.6935	0.3691	0.2721	0.087*
C6	0.7878 (2)	0.49954 (18)	0.21537 (11)	0.0641 (5)
H6	0.8735	0.4613	0.2152	0.077*
C7	0.85364 (16)	0.77757 (15)	0.11304 (8)	0.0430 (4)
C8	0.71927 (17)	0.83557 (15)	0.11509 (8)	0.0433 (4)
C9	0.68921 (17)	0.96032 (16)	0.08390 (9)	0.0464 (4)
C10	0.75162 (19)	1.06703 (16)	0.11096 (9)	0.0528 (5)
C11	0.7215 (2)	1.18364 (17)	0.08143 (11)	0.0638 (5)
H11	0.7619	1.2557	0.0994	0.077*
C12	0.6323 (2)	1.1920 (2)	0.02580 (12)	0.0684 (6)
H12	0.6153	1.2697	0.0055	0.082*
C13	0.5678 (2)	1.0874 (2)	−0.00042 (12)	0.0676 (5)
H13	0.5062	1.0943	−0.0375	0.081*
C14	0.59580 (18)	0.97191 (18)	0.02901 (11)	0.0550 (5)
H14	0.5517	0.9009	0.0119	0.066*
C15	0.97327 (16)	0.83049 (16)	0.07577 (9)	0.0453 (4)
C16	1.10760 (18)	0.80861 (18)	0.09958 (9)	0.0529 (4)
C17	1.2185 (2)	0.8622 (2)	0.06566 (11)	0.0625 (5)
H17	1.3065	0.8496	0.0830	0.075*
C18	1.1996 (2)	0.9338 (2)	0.00648 (10)	0.0633 (5)
H18	1.2746	0.9701	−0.0157	0.076*
C19	1.0700 (2)	0.95219 (19)	−0.02002 (10)	0.0615 (5)
H19	1.0576	0.9991	−0.0607	0.074*
C20	0.95835 (19)	0.90080 (18)	0.01386 (9)	0.0523 (4)
H20	0.8712	0.9130	−0.0047	0.063*
C21	0.2074 (3)	0.4182 (2)	0.17613 (15)	0.0940 (8)
H21A	0.2527	0.4731	0.1436	0.141*
H21B	0.2483	0.4268	0.2217	0.141*
H21C	0.1120	0.4399	0.1787	0.141*
C22	0.3494 (2)	0.2530 (3)	0.11988 (14)	0.0951 (8)
H22A	0.3473	0.1649	0.1095	0.143*
H22B	0.4238	0.2704	0.1514	0.143*
H22C	0.3619	0.2993	0.0772	0.143*
C23	0.1181 (2)	0.2123 (2)	0.15743 (10)	0.0660 (5)
H23	0.1303	0.1311	0.1408	0.079*

	U11	U22	U33	U12	U13	U23
N1	0.0505 (8)	0.0416 (8)	0.0568 (8)	−0.0064 (7)	−0.0007 (7)	0.0007 (7)
N2	0.0512 (8)	0.0368 (8)	0.0601 (8)	−0.0058 (6)	0.0123 (7)	−0.0042 (6)
N3	0.0591 (10)	0.0707 (11)	0.0620 (9)	0.0009 (9)	0.0025 (8)	−0.0038 (8)
O1	0.0513 (8)	0.0915 (11)	0.0886 (10)	−0.0128 (8)	−0.0080 (7)	0.0264 (9)
O2	0.0955 (11)	0.0479 (8)	0.0652 (8)	−0.0194 (7)	−0.0054 (7)	−0.0031 (6)
O3	0.0707 (10)	0.0683 (10)	0.0996 (11)	−0.0145 (8)	0.0137 (9)	−0.0173 (8)
C1	0.0572 (10)	0.0390 (8)	0.0486 (9)	−0.0130 (8)	0.0007 (8)	−0.0009 (7)
C2	0.0576 (10)	0.0378 (9)	0.0504 (9)	−0.0130 (9)	0.0080 (8)	−0.0041 (7)
C3	0.0657 (12)	0.0562 (12)	0.0697 (12)	−0.0169 (10)	0.0190 (10)	0.0010 (9)
C4	0.0841 (16)	0.0620 (13)	0.0673 (13)	−0.0310 (12)	0.0107 (12)	0.0086 (10)
C5	0.0904 (17)	0.0550 (13)	0.0709 (12)	−0.0213 (12)	−0.0100 (12)	0.0199 (10)
C6	0.0700 (12)	0.0502 (11)	0.0721 (12)	−0.0085 (10)	−0.0075 (11)	0.0112 (10)
C7	0.0475 (9)	0.0362 (8)	0.0454 (8)	−0.0051 (7)	0.0043 (7)	−0.0075 (7)
C8	0.0478 (8)	0.0343 (8)	0.0478 (8)	−0.0065 (7)	0.0088 (8)	−0.0061 (7)
C9	0.0470 (9)	0.0364 (8)	0.0559 (9)	−0.0021 (7)	0.0157 (8)	−0.0025 (7)
C10	0.0645 (11)	0.0408 (9)	0.0530 (10)	−0.0061 (8)	0.0175 (9)	−0.0023 (8)
C11	0.0821 (13)	0.0348 (9)	0.0747 (13)	−0.0040 (10)	0.0253 (11)	−0.0012 (9)
C12	0.0776 (14)	0.0490 (12)	0.0786 (14)	0.0106 (11)	0.0244 (12)	0.0142 (10)
C13	0.0598 (12)	0.0668 (14)	0.0762 (13)	0.0110 (11)	0.0068 (10)	0.0094 (11)
C14	0.0470 (10)	0.0502 (11)	0.0679 (11)	0.0005 (8)	0.0102 (9)	−0.0015 (9)
C15	0.0478 (9)	0.0362 (9)	0.0519 (9)	−0.0041 (7)	0.0088 (8)	−0.0068 (7)
C16	0.0544 (10)	0.0481 (10)	0.0564 (10)	−0.0085 (8)	0.0057 (8)	−0.0063 (8)
C17	0.0482 (10)	0.0697 (13)	0.0696 (12)	−0.0101 (10)	0.0085 (10)	−0.0117 (10)
C18	0.0584 (12)	0.0635 (13)	0.0681 (12)	−0.0121 (10)	0.0250 (10)	−0.0117 (10)
C19	0.0715 (13)	0.0592 (12)	0.0539 (10)	−0.0016 (10)	0.0217 (9)	−0.0018 (9)
C20	0.0548 (10)	0.0509 (10)	0.0513 (10)	0.0036 (9)	0.0120 (8)	−0.0033 (8)
C21	0.0760 (15)	0.0876 (18)	0.119 (2)	−0.0221 (15)	0.0046 (15)	−0.0334 (16)
C22	0.0715 (15)	0.128 (2)	0.0853 (16)	0.0205 (16)	0.0133 (12)	0.0106 (16)
C23	0.0809 (15)	0.0573 (13)	0.0598 (12)	0.0019 (11)	0.0001 (11)	−0.0042 (9)

N1—C7	1.321 (2)	C9—C14	1.393 (3)
N1—C1	1.370 (2)	C10—C11	1.397 (3)
N2—C8	1.313 (2)	C11—C12	1.374 (3)
N2—C2	1.374 (2)	C11—H11	0.9300
N3—C23	1.304 (3)	C12—C13	1.376 (3)
N3—C21	1.450 (3)	C12—H12	0.9300
N3—C22	1.452 (3)	C13—C14	1.381 (3)
O1—C16	1.356 (2)	C13—H13	0.9300
O1—H1	0.8200	C14—H14	0.9300
O2—C10	1.348 (2)	C15—C20	1.405 (2)
O2—H2	0.8200	C15—C16	1.407 (3)
O3—C23	1.243 (2)	C16—C17	1.384 (3)
C1—C2	1.398 (3)	C17—C18	1.375 (3)
C1—C6	1.411 (3)	C17—H17	0.9300
C2—C3	1.412 (2)	C18—C19	1.376 (3)
C3—C4	1.356 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.380 (3)
C4—C5	1.393 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.358 (3)	C21—H21A	0.9600
C5—H5	0.9300	C21—H21B	0.9600
C6—H6	0.9300	C21—H21C	0.9600
C7—C8	1.451 (2)	C22—H22A	0.9600
C7—C15	1.479 (2)	C22—H22B	0.9600
C8—C9	1.487 (2)	C22—H22C	0.9600
C9—C10	1.391 (2)	C23—H23	0.9300
C7—N1—C1	118.91 (15)	C11—C12—H12	119.4
C8—N2—C2	117.87 (15)	C13—C12—H12	119.4
C23—N3—C21	120.37 (19)	C12—C13—C14	119.1 (2)
C23—N3—C22	121.7 (2)	C12—C13—H13	120.5
C21—N3—C22	117.9 (2)	C14—C13—H13	120.5
C16—O1—H1	109.5	C13—C14—C9	120.89 (19)
C10—O2—H2	109.5	C13—C14—H14	119.6
N1—C1—C2	120.52 (15)	C9—C14—H14	119.6
N1—C1—C6	119.86 (18)	C20—C15—C16	117.11 (15)
C2—C1—C6	119.61 (17)	C20—C15—C7	121.67 (15)
N2—C2—C1	120.99 (15)	C16—C15—C7	121.18 (15)
N2—C2—C3	119.22 (18)	O1—C16—C17	116.38 (17)
C1—C2—C3	119.74 (17)	O1—C16—C15	122.97 (16)
C4—C3—C2	119.1 (2)	C17—C16—C15	120.65 (17)
C4—C3—H3	120.4	C18—C17—C16	120.49 (19)
C2—C3—H3	120.4	C18—C17—H17	119.8
C3—C4—C5	121.28 (19)	C16—C17—H17	119.8
C3—C4—H4	119.4	C17—C18—C19	120.25 (18)
C5—C4—H4	119.4	C17—C18—H18	119.9
C6—C5—C4	121.0 (2)	C19—C18—H18	119.9
C6—C5—H5	119.5	C18—C19—C20	119.84 (19)
C4—C5—H5	119.5	C18—C19—H19	120.1
C5—C6—C1	119.3 (2)	C20—C19—H19	120.1
C5—C6—H6	120.4	C19—C20—C15	121.53 (18)
C1—C6—H6	120.4	C19—C20—H20	119.2
N1—C7—C8	119.88 (14)	C15—C20—H20	119.2
N1—C7—C15	115.80 (15)	N3—C21—H21A	109.5
C8—C7—C15	124.31 (15)	N3—C21—H21B	109.5
N2—C8—C7	121.74 (15)	H21A—C21—H21B	109.5
N2—C8—C9	114.88 (15)	N3—C21—H21C	109.5
C7—C8—C9	123.34 (14)	H21A—C21—H21C	109.5
C10—C9—C14	119.49 (17)	H21B—C21—H21C	109.5
C10—C9—C8	119.91 (16)	N3—C22—H22A	109.5
C14—C9—C8	120.57 (15)	N3—C22—H22B	109.5
O2—C10—C9	117.14 (15)	H22A—C22—H22B	109.5
O2—C10—C11	123.62 (17)	N3—C22—H22C	109.5
C9—C10—C11	119.22 (18)	H22A—C22—H22C	109.5
C12—C11—C10	120.10 (19)	H22B—C22—H22C	109.5
C12—C11—H11	120.0	O3—C23—N3	124.4 (2)
C10—C11—H11	120.0	O3—C23—H23	117.8
C11—C12—C13	121.16 (19)	N3—C23—H23	117.8

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.82	1.81	2.6172 (19)	168
O1—H1···N1	0.82	1.94	2.647 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.82	1.81	2.6172 (19)	168
O1—H1⋯N1	0.82	1.94	2.647 (2)	144

Symmetry code: (i) .