(Phen-yl)(3-phenyl-sulfonyl-1,2-dihydro-pyrrolo-[1,2-a]quinoxalin-1-yl)methanone.

In the title mol-ecule, C(24)H(18)N(2)O(3)S, the 13-atom ring system comprising the quinoxaline and fused five-membered ring exhibits an r.m.s. deviation from coplanarity of 0.039 Å, with a maximum deviation of 0.0710 (10) Å for the PhCO-bearing C atom of the five-membered ring. The 10-membered C(8)N(2) quinoxaline ring system has an r.m.s. deviation from coplanarity of 0.022 Å, with a maximum deviation of 0.0403 (9) Å for the C atom involved in the C=C bond in the five-membered ring. The three atoms of the five-membered ring fused to the quinoxaline ring system show deviations of up to 0.118 (2) Å for the PhCO-bearing C atom. C-N bond distances in the quinoxaline ring system of the title mol-ecule deviate from those in unsubstituted quinoxaline. In particular, the two C-N distances to the N atom involved in the five-membered ring are essentially equal, with values of 1.3786 (17) and 1.3773 (16) Å, unlike the difference of nearly 0.06 Å in quinoxaline.

Related literature

For the transformation of benzimidazoles into pyrrolo­quinoxalines, see: Ager et al. (1988 ▶); Methcohn (1975 ▶). For the synthesis of condensed pyrazines, see: Cheeseman & Cookson (1979 ▶). For the biological activity of quinoxalines, see: Porter (1984 ▶); He et al. (2003 ▶); Kim et al. (2004 ▶). For cyclization reactions of quinoxaline derivatives, see: Taylor & Hand (1962 ▶, 1963 ▶); Yadav et al. (2008 ▶). For the structure of an analogous compound with COOMe at C9 and C10, see: Hirano et al. (2002 ▶). For polymorphs of quinoxaline, see: Ranganathan et al. (2010 ▶); Anthony et al. (1998 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C24H18N2O3S

M = 414.46

Monoclinic,

a = 19.0915 (9) Å

b = 9.9636 (5) Å

c = 10.4203 (5) Å

β = 104.6190 (13)°

V = 1917.98 (16) Å3

Z = 4

Cu Kα radiation

μ = 1.75 mm−1

T = 90 K

0.30 × 0.27 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.622, T max = 0.804

31213 measured reflections

3621 independent reflections

3543 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.04

3621 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040335/nk2116sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040335/nk2116Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040335/nk2116Isup3.cml

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

C24H18N2O3S	F(000) = 864
Mr = 414.46	Dx = 1.435 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9862 reflections
a = 19.0915 (9) Å	θ = 4.4–70.1°
b = 9.9636 (5) Å	µ = 1.75 mm−1
c = 10.4203 (5) Å	T = 90 K
β = 104.6190 (13)°	Rectangular prism, orange
V = 1917.98 (16) Å3	0.30 × 0.27 × 0.13 mm
Z = 4

Bruker APEXII CCD diffractometer	3621 independent reflections
Radiation source: fine-focus sealed tube	3543 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 70.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −23→23
Tmin = 0.622, Tmax = 0.804	k = −10→12
31213 measured reflections	l = −12→12

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0349P)2 + 1.1954P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3621 reflections	Δρmax = 0.41 e Å−3
272 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00108 (12)

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
S1	0.347686 (15)	0.61731 (3)	0.66691 (3)	0.01450 (10)
O1	0.36497 (5)	0.53406 (10)	0.56612 (9)	0.0205 (2)
O2	0.31216 (5)	0.74476 (9)	0.63034 (9)	0.0200 (2)
O3	0.11000 (5)	0.43117 (9)	0.71433 (9)	0.0190 (2)
N1	0.29905 (6)	0.15898 (11)	0.69500 (10)	0.0166 (2)
N2	0.24574 (6)	0.35506 (11)	0.83452 (10)	0.0146 (2)
C1	0.25306 (7)	0.12578 (13)	0.77577 (12)	0.0155 (3)
C2	0.23431 (7)	−0.00846 (13)	0.78555 (13)	0.0182 (3)
H2	0.2537	−0.0755	0.7395	0.022*
C3	0.18766 (7)	−0.04454 (13)	0.86193 (13)	0.0198 (3)
H3	0.1741	−0.1358	0.8665	0.024*
C4	0.16049 (7)	0.05308 (13)	0.93218 (13)	0.0181 (3)
H4	0.1290	0.0275	0.9854	0.022*
C5	0.17878 (7)	0.18683 (13)	0.92537 (12)	0.0162 (3)
H5	0.1602	0.2527	0.9739	0.019*
C6	0.22492 (6)	0.22410 (13)	0.84637 (12)	0.0142 (3)
C7	0.31442 (7)	0.28371 (13)	0.68290 (12)	0.0159 (3)
H7	0.3450	0.3057	0.6268	0.019*
C8	0.28749 (6)	0.39240 (13)	0.75032 (12)	0.0142 (3)
C9	0.29573 (6)	0.52749 (13)	0.74933 (12)	0.0150 (3)
C10	0.25941 (7)	0.59237 (13)	0.84700 (13)	0.0170 (3)
H10A	0.2265	0.6655	0.8048	0.020*
H10B	0.2955	0.6285	0.9247	0.020*
C11	0.21643 (7)	0.47295 (12)	0.88718 (12)	0.0145 (3)
H11	0.2249	0.4671	0.9857	0.017*
C12	0.13534 (7)	0.48735 (12)	0.81931 (12)	0.0139 (3)
C13	0.09098 (7)	0.57500 (12)	0.88358 (12)	0.0144 (3)
C14	0.12184 (7)	0.65545 (13)	0.99308 (12)	0.0163 (3)
H14	0.1727	0.6549	1.0296	0.020*
C15	0.07783 (7)	0.73617 (14)	1.04836 (13)	0.0210 (3)
H15	0.0987	0.7912	1.1226	0.025*
C16	0.00346 (8)	0.73669 (14)	0.99538 (15)	0.0231 (3)
H16	−0.0264	0.7924	1.0333	0.028*
C17	−0.02763 (7)	0.65613 (15)	0.88708 (14)	0.0223 (3)
H17	−0.0786	0.6563	0.8515	0.027*
C18	0.01584 (7)	0.57577 (14)	0.83122 (13)	0.0181 (3)
H18	−0.0054	0.5209	0.7570	0.022*
C19	0.42916 (7)	0.64997 (14)	0.78853 (12)	0.0168 (3)
C20	0.48648 (7)	0.56023 (15)	0.80223 (14)	0.0223 (3)
H20	0.4825	0.4844	0.7456	0.027*
C21	0.54965 (8)	0.58369 (18)	0.90036 (15)	0.0304 (4)
H21	0.5896	0.5242	0.9109	0.037*
C22	0.55422 (8)	0.69423 (19)	0.98282 (14)	0.0326 (4)
H22	0.5975	0.7099	1.0497	0.039*
C23	0.49673 (8)	0.78208 (17)	0.96936 (14)	0.0292 (3)
H23	0.5006	0.8570	1.0272	0.035*
C24	0.43328 (7)	0.76078 (15)	0.87121 (13)	0.0218 (3)
H24	0.3936	0.8207	0.8608	0.026*

	U11	U22	U33	U12	U13	U23
S1	0.01365 (16)	0.01546 (17)	0.01436 (16)	−0.00031 (11)	0.00346 (11)	0.00024 (11)
O1	0.0224 (5)	0.0226 (5)	0.0183 (5)	−0.0015 (4)	0.0087 (4)	−0.0023 (4)
O2	0.0200 (5)	0.0191 (5)	0.0203 (5)	0.0021 (4)	0.0039 (4)	0.0038 (4)
O3	0.0197 (5)	0.0201 (5)	0.0166 (4)	0.0001 (4)	0.0035 (4)	−0.0032 (4)
N1	0.0158 (5)	0.0174 (6)	0.0162 (5)	0.0023 (4)	0.0034 (4)	−0.0019 (4)
N2	0.0142 (5)	0.0138 (5)	0.0169 (5)	0.0011 (4)	0.0060 (4)	−0.0022 (4)
C1	0.0137 (6)	0.0174 (7)	0.0142 (6)	0.0026 (5)	0.0014 (5)	−0.0007 (5)
C2	0.0204 (6)	0.0151 (6)	0.0179 (6)	0.0039 (5)	0.0025 (5)	−0.0022 (5)
C3	0.0235 (7)	0.0136 (6)	0.0210 (7)	0.0000 (5)	0.0034 (5)	0.0012 (5)
C4	0.0172 (6)	0.0191 (7)	0.0175 (6)	−0.0001 (5)	0.0033 (5)	0.0024 (5)
C5	0.0151 (6)	0.0167 (6)	0.0166 (6)	0.0022 (5)	0.0037 (5)	−0.0008 (5)
C6	0.0125 (6)	0.0143 (6)	0.0141 (6)	0.0012 (5)	−0.0002 (5)	−0.0005 (5)
C7	0.0139 (6)	0.0185 (7)	0.0156 (6)	0.0018 (5)	0.0043 (5)	−0.0024 (5)
C8	0.0103 (5)	0.0180 (6)	0.0134 (6)	0.0004 (5)	0.0015 (4)	−0.0010 (5)
C9	0.0124 (6)	0.0166 (6)	0.0158 (6)	−0.0003 (5)	0.0033 (5)	−0.0016 (5)
C10	0.0164 (6)	0.0144 (6)	0.0218 (6)	−0.0009 (5)	0.0077 (5)	−0.0034 (5)
C11	0.0158 (6)	0.0125 (6)	0.0159 (6)	0.0016 (5)	0.0051 (5)	−0.0024 (5)
C12	0.0165 (6)	0.0113 (6)	0.0146 (6)	−0.0010 (5)	0.0052 (5)	0.0024 (5)
C13	0.0162 (6)	0.0126 (6)	0.0155 (6)	0.0013 (5)	0.0060 (5)	0.0033 (5)
C14	0.0155 (6)	0.0153 (6)	0.0185 (6)	0.0003 (5)	0.0047 (5)	0.0008 (5)
C15	0.0233 (7)	0.0187 (7)	0.0212 (6)	0.0012 (5)	0.0062 (5)	−0.0047 (5)
C16	0.0223 (7)	0.0220 (7)	0.0274 (7)	0.0077 (5)	0.0110 (6)	−0.0004 (6)
C17	0.0148 (6)	0.0264 (7)	0.0254 (7)	0.0045 (5)	0.0044 (5)	0.0023 (6)
C18	0.0176 (6)	0.0188 (7)	0.0170 (6)	0.0004 (5)	0.0028 (5)	0.0012 (5)
C19	0.0138 (6)	0.0215 (7)	0.0158 (6)	−0.0034 (5)	0.0049 (5)	0.0039 (5)
C20	0.0181 (6)	0.0270 (7)	0.0240 (7)	0.0009 (5)	0.0094 (5)	0.0079 (6)
C21	0.0140 (6)	0.0467 (10)	0.0311 (8)	0.0020 (6)	0.0065 (6)	0.0193 (7)
C22	0.0188 (7)	0.0560 (11)	0.0203 (7)	−0.0147 (7)	−0.0002 (5)	0.0121 (7)
C23	0.0287 (8)	0.0396 (9)	0.0196 (7)	−0.0167 (7)	0.0063 (6)	−0.0021 (6)
C24	0.0205 (7)	0.0253 (7)	0.0206 (6)	−0.0059 (5)	0.0070 (5)	−0.0001 (5)

S1—O1	1.4404 (9)	C10—H10B	0.9900
S1—O2	1.4448 (10)	C11—C12	1.5377 (17)
S1—C9	1.7183 (13)	C11—H11	1.0000
S1—C19	1.7710 (13)	C12—C13	1.4882 (17)
O3—C12	1.2152 (16)	C13—C14	1.3972 (18)
N1—C7	1.2904 (18)	C13—C18	1.4003 (18)
N1—C1	1.4007 (17)	C14—C15	1.3889 (18)
N2—C8	1.3773 (16)	C14—H14	0.9500
N2—C6	1.3786 (17)	C15—C16	1.387 (2)
N2—C11	1.4660 (15)	C15—H15	0.9500
C1—C2	1.3950 (19)	C16—C17	1.390 (2)
C1—C6	1.4103 (17)	C16—H16	0.9500
C2—C3	1.3833 (19)	C17—C18	1.3829 (19)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.3937 (19)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.3924 (19)
C4—C5	1.3840 (19)	C19—C24	1.390 (2)
C4—H4	0.9500	C20—C21	1.390 (2)
C5—C6	1.3991 (18)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.386 (3)
C7—C8	1.4536 (17)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.383 (2)
C8—C9	1.3555 (18)	C22—H22	0.9500
C9—C10	1.5135 (17)	C23—C24	1.390 (2)
C10—C11	1.5613 (17)	C23—H23	0.9500
C10—H10A	0.9900	C24—H24	0.9500
O1—S1—O2	119.51 (6)	N2—C11—C10	103.55 (9)
O1—S1—C9	109.38 (6)	C12—C11—C10	109.99 (10)
O2—S1—C9	107.32 (6)	N2—C11—H11	111.1
O1—S1—C19	107.83 (6)	C12—C11—H11	111.1
O2—S1—C19	107.24 (6)	C10—C11—H11	111.1
C9—S1—C19	104.57 (6)	O3—C12—C13	122.20 (11)
C7—N1—C1	118.60 (11)	O3—C12—C11	119.79 (11)
C8—N2—C6	122.62 (11)	C13—C12—C11	117.97 (10)
C8—N2—C11	111.04 (10)	C14—C13—C18	119.63 (12)
C6—N2—C11	125.38 (10)	C14—C13—C12	122.25 (11)
C2—C1—N1	118.80 (11)	C18—C13—C12	118.12 (11)
C2—C1—C6	119.30 (12)	C15—C14—C13	119.77 (12)
N1—C1—C6	121.90 (12)	C15—C14—H14	120.1
C3—C2—C1	120.36 (12)	C13—C14—H14	120.1
C3—C2—H2	119.8	C14—C15—C16	120.17 (13)
C1—C2—H2	119.8	C14—C15—H15	119.9
C2—C3—C4	119.99 (12)	C16—C15—H15	119.9
C2—C3—H3	120.0	C17—C16—C15	120.35 (12)
C4—C3—H3	120.0	C17—C16—H16	119.8
C5—C4—C3	120.85 (12)	C15—C16—H16	119.8
C5—C4—H4	119.6	C18—C17—C16	119.83 (12)
C3—C4—H4	119.6	C18—C17—H17	120.1
C4—C5—C6	119.35 (12)	C16—C17—H17	120.1
C4—C5—H5	120.3	C17—C18—C13	120.25 (12)
C6—C5—H5	120.3	C17—C18—H18	119.9
N2—C6—C5	122.85 (11)	C13—C18—H18	119.9
N2—C6—C1	117.02 (11)	C20—C19—C24	121.75 (13)
C5—C6—C1	120.12 (12)	C20—C19—S1	118.75 (11)
N1—C7—C8	123.60 (12)	C24—C19—S1	119.44 (10)
N1—C7—H7	118.2	C21—C20—C19	118.75 (14)
C8—C7—H7	118.2	C21—C20—H20	120.6
C9—C8—N2	111.10 (11)	C19—C20—H20	120.6
C9—C8—C7	132.87 (12)	C22—C21—C20	119.79 (14)
N2—C8—C7	116.03 (11)	C22—C21—H21	120.1
C8—C9—C10	110.20 (11)	C20—C21—H21	120.1
C8—C9—S1	127.13 (10)	C23—C22—C21	121.06 (13)
C10—C9—S1	122.27 (9)	C23—C22—H22	119.5
C9—C10—C11	102.46 (10)	C21—C22—H22	119.5
C9—C10—H10A	111.3	C22—C23—C24	119.98 (15)
C11—C10—H10A	111.3	C22—C23—H23	120.0
C9—C10—H10B	111.3	C24—C23—H23	120.0
C11—C10—H10B	111.3	C23—C24—C19	118.67 (14)
H10A—C10—H10B	109.2	C23—C24—H24	120.7
N2—C11—C12	109.74 (10)	C19—C24—H24	120.7
C7—N1—C1—C2	177.83 (12)	C8—N2—C11—C12	105.72 (11)
C7—N1—C1—C6	−1.70 (18)	C6—N2—C11—C12	−63.24 (15)
N1—C1—C2—C3	−178.48 (11)	C8—N2—C11—C10	−11.67 (13)
C6—C1—C2—C3	1.06 (19)	C6—N2—C11—C10	179.38 (11)
C1—C2—C3—C4	−1.5 (2)	C9—C10—C11—N2	12.32 (12)
C2—C3—C4—C5	0.9 (2)	C9—C10—C11—C12	−104.89 (11)
C3—C4—C5—C6	0.27 (19)	N2—C11—C12—O3	−19.31 (16)
C8—N2—C6—C5	−175.85 (11)	C10—C11—C12—O3	93.98 (13)
C11—N2—C6—C5	−8.11 (19)	N2—C11—C12—C13	162.91 (10)
C8—N2—C6—C1	4.95 (17)	C10—C11—C12—C13	−83.80 (13)
C11—N2—C6—C1	172.69 (11)	O3—C12—C13—C14	−170.10 (12)
C4—C5—C6—N2	−179.91 (11)	C11—C12—C13—C14	7.62 (17)
C4—C5—C6—C1	−0.74 (18)	O3—C12—C13—C18	9.85 (18)
C2—C1—C6—N2	179.30 (11)	C11—C12—C13—C18	−172.43 (11)
N1—C1—C6—N2	−1.17 (17)	C18—C13—C14—C15	−0.50 (19)
C2—C1—C6—C5	0.08 (18)	C12—C13—C14—C15	179.45 (12)
N1—C1—C6—C5	179.61 (11)	C13—C14—C15—C16	0.2 (2)
C1—N1—C7—C8	1.00 (18)	C14—C15—C16—C17	0.3 (2)
C6—N2—C8—C9	175.24 (11)	C15—C16—C17—C18	−0.5 (2)
C11—N2—C8—C9	5.93 (14)	C16—C17—C18—C13	0.2 (2)
C6—N2—C8—C7	−5.56 (17)	C14—C13—C18—C17	0.30 (19)
C11—N2—C8—C7	−174.87 (10)	C12—C13—C18—C17	−179.65 (12)
N1—C7—C8—C9	−178.52 (13)	O1—S1—C19—C20	−24.23 (12)
N1—C7—C8—N2	2.50 (18)	O2—S1—C19—C20	−154.13 (10)
N2—C8—C9—C10	2.97 (15)	C9—S1—C19—C20	92.12 (11)
C7—C8—C9—C10	−176.05 (13)	O1—S1—C19—C24	158.43 (10)
N2—C8—C9—S1	175.80 (9)	O2—S1—C19—C24	28.53 (12)
C7—C8—C9—S1	−3.2 (2)	C9—S1—C19—C24	−85.22 (11)
O1—S1—C9—C8	17.24 (14)	C24—C19—C20—C21	−0.8 (2)
O2—S1—C9—C8	148.29 (12)	S1—C19—C20—C21	−178.08 (10)
C19—S1—C9—C8	−98.03 (12)	C19—C20—C21—C22	0.6 (2)
O1—S1—C9—C10	−170.72 (10)	C20—C21—C22—C23	0.1 (2)
O2—S1—C9—C10	−39.67 (11)	C21—C22—C23—C24	−0.5 (2)
C19—S1—C9—C10	74.02 (11)	C22—C23—C24—C19	0.3 (2)
C8—C9—C10—C11	−9.76 (13)	C20—C19—C24—C23	0.4 (2)
S1—C9—C10—C11	176.99 (9)	S1—C19—C24—C23	177.63 (10)