2-[(E)-(5-Amino-2,3-diphenyl-quinoxalin-6-yl)imino-meth-yl]-4-bromo-phenol.

The title compound, C(27)H(19)BrN(4)O, is a mono-anil Schiff base ligand. Three intra-molecular O-H⋯N and N-H⋯N hydrogen bonds involving the hydr-oxy and amino groups generate S(6) and S(5) ring motifs, respectively. In the crystal structure, weak inter-molecular N-H⋯O and C-H⋯O hydrogen bonds together with π-π inter-actions [centroid-centroid distances = 3.628 (3)-3.729 (3) Å] link neighboring mol-ecules.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures see, for example: Corden et al. (1996 ▶); Govindasamy et al. (1999 ▶). For applications and bioactivities see, for example: Blower (1998 ▶); Cohen & Schmidt (1964 ▶); Granovski et al. (1993 ▶); Kia et al. (2004 ▶); Li & Chang (1991 ▶); Shahrokhian et al. (2000 ▶); Uhlenbrock et al. (1996 ▶); Unaleroglu & Hokelek (2002 ▶). For related literature, see: Anderson et al. (1997 ▶); Blower (1998 ▶).

Experimental

Crystal data

C27H19BrN4O

M = 495.37

Monoclinic,

a = 22.923 (5) Å

b = 7.344 (5) Å

c = 12.573 (5) Å

β = 92.070 (5)°

V = 2115.2 (17) Å3

Z = 4

Mo Kα radiation

μ = 1.97 mm−1

T = 100.0 (1) K

0.39 × 0.37 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.510, T max = 0.853

22554 measured reflections

6205 independent reflections

3722 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.142

S = 1.06

6205 reflections

305 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −1.07 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017716/sj2516sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017716/sj2516Isup2.hkl

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

C27H19BrN4O	F000 = 1008
Mr = 495.37	Dx = 1.556 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 4509 reflections
a = 22.923 (5) Å	θ = 2.9–28.3º
b = 7.344 (5) Å	µ = 1.97 mm−1
c = 12.573 (5) Å	T = 100.0 (1) K
β = 92.070 (5)º	Block, yellow
V = 2115.2 (17) Å3	0.39 × 0.37 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6205 independent reflections
Radiation source: fine-focus sealed tube	3722 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.070
T = 100.0(1) K	θmax = 30.1º
φ and ω scans	θmin = 0.9º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −32→32
Tmin = 0.510, Tmax = 0.853	k = −10→8
22554 measured reflections	l = −16→17

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0698P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
6205 reflections	Δρmax = 0.62 e Å−3
305 parameters	Δρmin = −1.07 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br1	0.259515 (13)	0.53134 (5)	0.59180 (3)	0.02170 (12)
N1	0.52495 (11)	0.6363 (4)	0.7764 (2)	0.0171 (6)
N2	0.60814 (13)	0.5339 (4)	0.9285 (2)	0.0186 (6)
N4	0.72399 (11)	0.5294 (4)	0.8819 (2)	0.0154 (6)
N3	0.76064 (11)	0.6677 (4)	0.6873 (2)	0.0169 (6)
O1	0.44969 (9)	0.7345 (3)	0.91363 (18)	0.0206 (5)
H1O1	0.4813	0.7101	0.8877	0.025*
C1	0.40804 (13)	0.6934 (4)	0.8389 (3)	0.0177 (7)
C2	0.34965 (14)	0.7191 (4)	0.8608 (3)	0.0188 (7)
H2	0.3398	0.7694	0.9256	0.023*
C3	0.30643 (13)	0.6715 (5)	0.7882 (3)	0.0205 (8)
H3	0.2675	0.6883	0.8044	0.025*
C4	0.32022 (13)	0.5985 (5)	0.6910 (3)	0.0183 (7)
C5	0.37775 (13)	0.5769 (4)	0.6645 (3)	0.0176 (7)
H5	0.3866	0.5305	0.5982	0.021*
C6	0.42273 (13)	0.6246 (4)	0.7373 (3)	0.0162 (7)
C7	0.48319 (13)	0.6048 (5)	0.7087 (3)	0.0166 (7)
H7	0.4917	0.5688	0.6400	0.010 (8)*
C8	0.58402 (12)	0.6335 (4)	0.7490 (3)	0.0146 (7)
C9	0.60282 (13)	0.6891 (4)	0.6473 (3)	0.0174 (7)
H9	0.5752	0.7203	0.5945	0.021*
C10	0.66057 (13)	0.6973 (4)	0.6258 (3)	0.0170 (7)
H10	0.6721	0.7344	0.5591	0.020*
C11	0.70293 (13)	0.6494 (4)	0.7053 (3)	0.0159 (7)
C14	0.68498 (13)	0.5891 (4)	0.8062 (3)	0.0135 (6)
C15	0.62412 (13)	0.5842 (4)	0.8283 (3)	0.0157 (7)
C12	0.79874 (13)	0.6218 (5)	0.7641 (3)	0.0165 (7)
C13	0.78033 (13)	0.5390 (4)	0.8603 (3)	0.0161 (7)
C16	0.82122 (13)	0.4561 (5)	0.9406 (3)	0.0174 (7)
C17	0.81113 (14)	0.4750 (5)	1.0488 (3)	0.0185 (7)
H17	0.7793	0.5428	1.0702	0.022*
C18	0.84782 (13)	0.3944 (5)	1.1246 (3)	0.0199 (7)
H18	0.8408	0.4086	1.1965	0.024*
C19	0.89531 (14)	0.2918 (5)	1.0935 (3)	0.0223 (8)
H19	0.9205	0.2393	1.1444	0.027*
C20	0.90483 (14)	0.2686 (5)	0.9858 (3)	0.0224 (8)
H20	0.9358	0.1970	0.9645	0.027*
C21	0.86863 (13)	0.3509 (5)	0.9104 (3)	0.0196 (7)
H21	0.8758	0.3364	0.8386	0.024*
C22	0.86036 (13)	0.6776 (4)	0.7467 (3)	0.0166 (7)
C23	0.89337 (13)	0.7640 (5)	0.8263 (3)	0.0198 (7)
H23	0.8786	0.7758	0.8939	0.024*
C24	0.94824 (14)	0.8330 (5)	0.8060 (3)	0.0220 (8)
H24	0.9701	0.8916	0.8595	0.026*
C25	0.97015 (14)	0.8138 (5)	0.7048 (3)	0.0215 (8)
H25	1.0068	0.8603	0.6906	0.026*
C26	0.93829 (14)	0.7271 (5)	0.6262 (3)	0.0215 (8)
H26	0.9535	0.7137	0.5590	0.026*
C27	0.88320 (13)	0.6588 (5)	0.6463 (3)	0.0198 (7)
H27	0.8615	0.6004	0.5925	0.024*
H2N2	0.6362 (17)	0.487 (5)	0.970 (3)	0.024*
H1N2	0.5740 (17)	0.479 (5)	0.925 (3)	0.024*

	U11	U22	U33	U12	U13	U23
Br1	0.01741 (16)	0.02067 (18)	0.0269 (2)	−0.00067 (13)	−0.00060 (13)	0.00133 (17)
N1	0.0177 (13)	0.0150 (15)	0.0187 (16)	0.0014 (10)	0.0023 (11)	0.0015 (12)
N2	0.0185 (13)	0.0240 (15)	0.0134 (15)	−0.0013 (12)	0.0037 (11)	0.0011 (13)
N4	0.0168 (12)	0.0141 (13)	0.0152 (15)	−0.0001 (10)	0.0007 (10)	−0.0019 (12)
N3	0.0178 (13)	0.0166 (15)	0.0163 (15)	−0.0007 (10)	0.0011 (11)	−0.0018 (12)
O1	0.0200 (11)	0.0251 (14)	0.0169 (13)	−0.0002 (9)	0.0033 (10)	−0.0002 (11)
C1	0.0213 (16)	0.0129 (17)	0.0190 (19)	−0.0012 (12)	0.0019 (14)	0.0034 (14)
C2	0.0228 (16)	0.0151 (17)	0.0189 (19)	0.0015 (12)	0.0044 (14)	0.0051 (14)
C3	0.0166 (15)	0.0174 (18)	0.028 (2)	0.0021 (12)	0.0043 (14)	0.0079 (15)
C4	0.0191 (15)	0.0133 (16)	0.022 (2)	−0.0001 (12)	0.0016 (13)	0.0046 (15)
C5	0.0197 (15)	0.0155 (17)	0.0178 (19)	0.0018 (12)	0.0028 (13)	0.0011 (13)
C6	0.0186 (15)	0.0131 (17)	0.0168 (18)	−0.0003 (12)	0.0026 (13)	0.0018 (14)
C7	0.0198 (15)	0.0130 (16)	0.0171 (19)	0.0009 (12)	0.0010 (13)	0.0022 (14)
C8	0.0155 (14)	0.0128 (16)	0.0156 (18)	−0.0012 (11)	0.0012 (12)	−0.0013 (13)
C9	0.0194 (15)	0.0153 (17)	0.0174 (19)	−0.0003 (12)	0.0001 (13)	0.0022 (14)
C10	0.0190 (15)	0.0168 (17)	0.0155 (18)	−0.0007 (12)	0.0027 (13)	0.0025 (14)
C11	0.0179 (15)	0.0135 (16)	0.0163 (18)	−0.0003 (11)	0.0034 (13)	−0.0002 (13)
C14	0.0181 (15)	0.0085 (14)	0.0137 (17)	0.0002 (11)	−0.0012 (12)	−0.0002 (13)
C15	0.0216 (15)	0.0112 (15)	0.0145 (18)	−0.0016 (12)	0.0027 (13)	−0.0036 (13)
C12	0.0154 (14)	0.0182 (17)	0.0161 (18)	0.0002 (12)	0.0028 (13)	−0.0020 (14)
C13	0.0164 (14)	0.0151 (16)	0.0169 (18)	0.0011 (12)	0.0021 (12)	−0.0046 (15)
C16	0.0155 (14)	0.0176 (17)	0.0192 (19)	−0.0021 (12)	0.0018 (12)	0.0008 (15)
C17	0.0195 (15)	0.0181 (16)	0.0180 (19)	−0.0017 (13)	0.0024 (13)	−0.0013 (15)
C18	0.0201 (16)	0.0218 (18)	0.0179 (19)	−0.0010 (13)	0.0003 (13)	0.0030 (15)
C19	0.0174 (16)	0.025 (2)	0.024 (2)	0.0000 (13)	−0.0026 (14)	0.0043 (16)
C20	0.0173 (15)	0.0227 (19)	0.028 (2)	0.0054 (13)	0.0036 (14)	0.0021 (16)
C21	0.0201 (16)	0.0191 (18)	0.0198 (19)	0.0015 (12)	0.0037 (14)	0.0013 (15)
C22	0.0160 (14)	0.0162 (17)	0.0180 (18)	0.0006 (12)	0.0034 (13)	−0.0004 (14)
C23	0.0188 (15)	0.0250 (19)	0.0158 (19)	−0.0009 (13)	0.0034 (13)	−0.0012 (15)
C24	0.0202 (16)	0.0253 (19)	0.020 (2)	−0.0019 (13)	0.0001 (14)	0.0012 (16)
C25	0.0162 (15)	0.027 (2)	0.022 (2)	0.0006 (13)	0.0034 (14)	0.0050 (16)
C26	0.0203 (16)	0.028 (2)	0.0165 (19)	0.0026 (13)	0.0049 (14)	0.0002 (16)
C27	0.0210 (16)	0.0221 (19)	0.0164 (19)	0.0029 (13)	0.0015 (13)	−0.0019 (15)

Br1—C4	1.900 (4)	C10—H10	0.9300
N1—C7	1.279 (4)	C11—C14	1.418 (4)
N1—C8	1.409 (3)	C14—C15	1.433 (4)
N2—C15	1.376 (4)	C12—C13	1.431 (4)
N2—H2N2	0.88 (4)	C12—C22	1.495 (4)
N2—H1N2	0.88 (4)	C13—C16	1.483 (5)
N4—C13	1.331 (4)	C16—C17	1.396 (5)
N4—C14	1.355 (4)	C16—C21	1.397 (4)
N3—C12	1.322 (4)	C17—C18	1.382 (5)
N3—C11	1.357 (4)	C17—H17	0.9300
O1—C1	1.350 (4)	C18—C19	1.391 (4)
O1—H1O1	0.8254	C18—H18	0.9300
C1—C2	1.389 (4)	C19—C20	1.390 (5)
C1—C6	1.425 (5)	C19—H19	0.9300
C2—C3	1.368 (5)	C20—C21	1.377 (5)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.382 (5)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.386 (5)
C4—C5	1.381 (4)	C22—C27	1.391 (4)
C5—C6	1.398 (5)	C23—C24	1.388 (4)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.452 (4)	C24—C25	1.392 (5)
C7—H7	0.9300	C24—H24	0.9300
C8—C15	1.380 (5)	C25—C26	1.365 (5)
C8—C9	1.424 (4)	C25—H25	0.9300
C9—C10	1.362 (4)	C26—C27	1.390 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.413 (5)	C27—H27	0.9300
C7—N1—C8	122.5 (3)	N2—C15—C14	118.5 (3)
C15—N2—H2N2	116 (3)	C8—C15—C14	118.8 (3)
C15—N2—H1N2	110 (3)	N3—C12—C13	121.2 (3)
H2N2—N2—H1N2	118 (4)	N3—C12—C22	115.2 (3)
C13—N4—C14	117.4 (3)	C13—C12—C22	123.3 (3)
C12—N3—C11	118.3 (3)	N4—C13—C12	120.8 (3)
C1—O1—H1O1	106.6	N4—C13—C16	115.7 (3)
O1—C1—C2	119.6 (3)	C12—C13—C16	123.4 (3)
O1—C1—C6	121.3 (3)	C17—C16—C21	118.5 (3)
C2—C1—C6	119.1 (3)	C17—C16—C13	120.0 (3)
C3—C2—C1	120.9 (3)	C21—C16—C13	121.4 (3)
C3—C2—H2	119.6	C18—C17—C16	120.8 (3)
C1—C2—H2	119.6	C18—C17—H17	119.6
C2—C3—C4	120.4 (3)	C16—C17—H17	119.6
C2—C3—H3	119.8	C17—C18—C19	120.0 (3)
C4—C3—H3	119.8	C17—C18—H18	120.0
C5—C4—C3	120.6 (3)	C19—C18—H18	120.0
C5—C4—Br1	119.7 (3)	C20—C19—C18	119.5 (3)
C3—C4—Br1	119.7 (2)	C20—C19—H19	120.2
C4—C5—C6	120.1 (3)	C18—C19—H19	120.2
C4—C5—H5	119.9	C21—C20—C19	120.3 (3)
C6—C5—H5	119.9	C21—C20—H20	119.8
C5—C6—C1	118.9 (3)	C19—C20—H20	119.8
C5—C6—C7	120.0 (3)	C20—C21—C16	120.8 (3)
C1—C6—C7	121.1 (3)	C20—C21—H21	119.6
N1—C7—C6	121.0 (3)	C16—C21—H21	119.6
N1—C7—H7	119.5	C23—C22—C27	119.1 (3)
C6—C7—H7	119.5	C23—C22—C12	121.0 (3)
C15—C8—N1	116.6 (3)	C27—C22—C12	119.6 (3)
C15—C8—C9	120.6 (3)	C22—C23—C24	120.6 (3)
N1—C8—C9	122.7 (3)	C22—C23—H23	119.7
C10—C9—C8	121.2 (3)	C24—C23—H23	119.7
C10—C9—H9	119.4	C23—C24—C25	119.3 (3)
C8—C9—H9	119.4	C23—C24—H24	120.3
C9—C10—C11	119.8 (3)	C25—C24—H24	120.3
C9—C10—H10	120.1	C26—C25—C24	120.5 (3)
C11—C10—H10	120.1	C26—C25—H25	119.7
N3—C11—C10	120.4 (3)	C24—C25—H25	119.7
N3—C11—C14	119.8 (3)	C25—C26—C27	120.2 (3)
C10—C11—C14	119.8 (3)	C25—C26—H26	119.9
N4—C14—C11	121.6 (3)	C27—C26—H26	119.9
N4—C14—C15	118.6 (3)	C26—C27—C22	120.2 (3)
C11—C14—C15	119.8 (3)	C26—C27—H27	119.9
N2—C15—C8	122.7 (3)	C22—C27—H27	119.9
O1—C1—C2—C3	−177.3 (3)	C11—C14—C15—N2	−176.8 (3)
C6—C1—C2—C3	3.1 (5)	N4—C14—C15—C8	−175.8 (3)
C1—C2—C3—C4	−0.7 (5)	C11—C14—C15—C8	2.0 (5)
C2—C3—C4—C5	−1.7 (5)	C11—N3—C12—C13	5.7 (5)
C2—C3—C4—Br1	179.5 (2)	C11—N3—C12—C22	−169.0 (3)
C3—C4—C5—C6	1.6 (5)	C14—N4—C13—C12	4.5 (4)
Br1—C4—C5—C6	−179.5 (2)	C14—N4—C13—C16	−174.3 (3)
C4—C5—C6—C1	0.7 (5)	N3—C12—C13—N4	−9.6 (5)
C4—C5—C6—C7	−178.9 (3)	C22—C12—C13—N4	164.7 (3)
O1—C1—C6—C5	177.3 (3)	N3—C12—C13—C16	169.1 (3)
C2—C1—C6—C5	−3.1 (5)	C22—C12—C13—C16	−16.6 (5)
O1—C1—C6—C7	−3.1 (5)	N4—C13—C16—C17	−39.1 (4)
C2—C1—C6—C7	176.6 (3)	C12—C13—C16—C17	142.2 (3)
C8—N1—C7—C6	−174.5 (3)	N4—C13—C16—C21	137.8 (3)
C5—C6—C7—N1	−175.3 (3)	C12—C13—C16—C21	−40.9 (5)
C1—C6—C7—N1	5.0 (5)	C21—C16—C17—C18	1.2 (5)
C7—N1—C8—C15	−150.5 (3)	C13—C16—C17—C18	178.1 (3)
C7—N1—C8—C9	33.4 (5)	C16—C17—C18—C19	−0.4 (5)
C15—C8—C9—C10	−0.8 (5)	C17—C18—C19—C20	−1.2 (5)
N1—C8—C9—C10	175.2 (3)	C18—C19—C20—C21	2.0 (5)
C8—C9—C10—C11	0.3 (5)	C19—C20—C21—C16	−1.2 (5)
C12—N3—C11—C10	179.8 (3)	C17—C16—C21—C20	−0.4 (5)
C12—N3—C11—C14	2.5 (4)	C13—C16—C21—C20	−177.3 (3)
C9—C10—C11—N3	−175.9 (3)	N3—C12—C22—C23	132.1 (3)
C9—C10—C11—C14	1.4 (5)	C13—C12—C22—C23	−42.5 (5)
C13—N4—C14—C11	3.7 (5)	N3—C12—C22—C27	−41.7 (4)
C13—N4—C14—C15	−178.6 (3)	C13—C12—C22—C27	143.7 (3)
N3—C11—C14—N4	−7.5 (5)	C27—C22—C23—C24	0.8 (5)
C10—C11—C14—N4	175.2 (3)	C12—C22—C23—C24	−173.0 (3)
N3—C11—C14—C15	174.8 (3)	C22—C23—C24—C25	−0.4 (5)
C10—C11—C14—C15	−2.5 (5)	C23—C24—C25—C26	−0.4 (5)
N1—C8—C15—N2	2.1 (5)	C24—C25—C26—C27	0.7 (5)
C9—C8—C15—N2	178.4 (3)	C25—C26—C27—C22	−0.3 (5)
N1—C8—C15—C14	−176.6 (3)	C23—C22—C27—C26	−0.4 (5)
C9—C8—C15—C14	−0.3 (5)	C12—C22—C27—C26	173.4 (3)
N4—C14—C15—N2	5.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.83	1.83	2.586 (4)	151
N2—H2N2···N4	0.88 (4)	2.35 (4)	2.740 (4)	107 (3)
N2—H1N2···N1	0.88 (4)	2.44 (4)	2.756 (4)	102 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.83	1.83	2.586 (4)	151
N2—H2N2⋯N4	0.88 (4)	2.35 (4)	2.740 (4)	107 (3)
N2—H1N2⋯N1	0.88 (4)	2.44 (4)	2.756 (4)	102 (3)