3-{[4-(4-Methyl­phenyl­sulfonamido)benzo­yl]methyl­idene}-3,4-dihydro­quinoxalin-2(1H)-one

The title compound, C₂₃H₁₉N₃O₄S, a quinoxalone derivative, is the product of the condensation reaction of 4-[4-(4-methyl­phenyl­sulfonamido)phen­yl]-2,4-dioxobutanoic acid with o-phenyl­enediamine. Inter­molecular N—H...O hydrogen bonds and π–π stacking inter­actions stabilize the solid structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.127
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.590     0.969
            Tmin(prime) and Tmax expected:      0.945     0.969
            RR(prime) =      0.624
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.62

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O2      ..       5.33 su
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

3-{[(4-(4-Methylphenylsulfonamido)benzoyl]methylidene}- 3,4-dihydroquinoxalin-2(1H)-one

Crystal data

C23H19N3O4S	F(000) = 452
Mr = 433.47	Dx = 1.427 Mg m^−3
Triclinic, P1	Melting point: 545 K
a = 7.485 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.509 (4) Å	Cell parameters from 1347 reflections
c = 16.377 (7) Å	θ = 2.6–25.2°
α = 82.938 (6)°	µ = 0.20 mm^−1
β = 78.218 (6)°	T = 293 K
γ = 83.095 (6)°	Block, pale-red
V = 1008.5 (8) Å^3	0.28 × 0.22 × 0.16 mm
Z = 2

Data collection

Bruker APEX-II CCD area-detector diffractometer	3431 independent reflections
Radiation source: fine-focus sealed tube	2356 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 0 pixels mm^-1	θmax = 25.0°, θmin = 2.6°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→6
Tmin = 0.590, Tmax = 0.969	l = −19→19
5245 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0658P)^2 + 0.1035P] where P = (Fo^2 + 2Fc^2)/3
3431 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.25930 (9)	−0.22301 (8)	0.32858 (4)	0.0546 (2)
O1	0.2367 (3)	−0.3663 (2)	0.38316 (12)	0.0753 (6)
O2	0.1433 (2)	−0.1774 (2)	0.26924 (12)	0.0681 (5)
O3	0.7890 (2)	0.2080 (2)	−0.04142 (10)	0.0568 (5)
O4	1.3256 (2)	0.3760 (2)	0.05185 (10)	0.0560 (5)
N1	0.4700 (3)	−0.2443 (2)	0.27916 (12)	0.0519 (5)
H1A	0.5335	−0.3322	0.2909	0.062*
N2	1.3689 (3)	0.4902 (2)	−0.08234 (12)	0.0464 (5)
H2B	1.4691	0.5237	−0.0766	0.056*
N3	1.0614 (2)	0.3775 (2)	−0.10551 (11)	0.0438 (5)
H3C	0.9644	0.3416	−0.1135	0.053*
C1	1.1548 (3)	0.4740 (3)	−0.17013 (14)	0.0425 (6)
C2	1.0937 (4)	0.5128 (3)	−0.24552 (15)	0.0551 (7)
H2	0.9872	0.4754	−0.2533	0.066*
C3	1.1936 (4)	0.6073 (3)	−0.30842 (16)	0.0616 (7)
H3	1.1547	0.6326	−0.3593	0.074*
C4	1.3500 (4)	0.6650 (3)	−0.29736 (16)	0.0587 (7)
H4	1.4145	0.7302	−0.3403	0.070*
C5	1.4119 (3)	0.6269 (3)	−0.22302 (15)	0.0515 (6)
H5	1.5186	0.6648	−0.2159	0.062*
C6	1.3129 (3)	0.5312 (3)	−0.15878 (14)	0.0422 (6)
C7	1.2769 (3)	0.4014 (3)	−0.01650 (15)	0.0430 (6)
C8	1.1115 (3)	0.3357 (3)	−0.03061 (14)	0.0411 (5)
C9	1.0169 (3)	0.2388 (3)	0.03228 (14)	0.0421 (6)
H9	1.0602	0.2132	0.0821	0.051*
C10	0.8546 (3)	0.1762 (3)	0.02393 (14)	0.0425 (6)
C11	0.7548 (3)	0.0727 (3)	0.09418 (13)	0.0396 (5)
C12	0.8303 (3)	0.0026 (3)	0.16258 (14)	0.0453 (6)
H12	0.9474	0.0227	0.1667	0.054*
C13	0.7324 (3)	−0.0965 (3)	0.22424 (14)	0.0466 (6)
H13	0.7826	−0.1404	0.2704	0.056*
C14	0.5602 (3)	−0.1310 (3)	0.21792 (14)	0.0424 (5)
C15	0.4825 (3)	−0.0614 (3)	0.15072 (14)	0.0508 (6)
H15	0.3662	−0.0830	0.1462	0.061*
C16	0.5796 (3)	0.0400 (3)	0.09083 (14)	0.0470 (6)
H16	0.5259	0.0884	0.0465	0.056*
C17	0.2445 (3)	−0.0650 (3)	0.38962 (15)	0.0482 (6)
C18	0.2169 (3)	0.0910 (3)	0.35440 (16)	0.0550 (7)
H18	0.2004	0.1122	0.2992	0.066*
C19	0.2145 (3)	0.2139 (3)	0.40227 (16)	0.0570 (7)
H19	0.1980	0.3182	0.3783	0.068*
C20	0.2357 (3)	0.1866 (3)	0.48476 (16)	0.0564 (7)
C21	0.2580 (4)	0.0297 (4)	0.51843 (17)	0.0683 (8)
H21	0.2695	0.0083	0.5743	0.082*
C22	0.2635 (4)	−0.0949 (3)	0.47217 (16)	0.0622 (7)
H22	0.2800	−0.1990	0.4963	0.075*
C23	0.2355 (4)	0.3229 (4)	0.53532 (18)	0.0783 (9)
H23A	0.1748	0.2967	0.5921	0.117*
H23B	0.1721	0.4166	0.5115	0.117*
H23C	0.3596	0.3422	0.5346	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0486 (4)	0.0495 (4)	0.0646 (4)	−0.0219 (3)	−0.0057 (3)	0.0063 (3)
O1	0.0817 (14)	0.0529 (12)	0.0848 (13)	−0.0315 (10)	−0.0007 (11)	0.0177 (10)
O2	0.0516 (11)	0.0818 (15)	0.0767 (12)	−0.0225 (10)	−0.0210 (9)	0.0000 (10)
O3	0.0616 (11)	0.0656 (12)	0.0491 (10)	−0.0298 (9)	−0.0169 (8)	0.0046 (9)
O4	0.0532 (10)	0.0616 (12)	0.0583 (11)	−0.0223 (9)	−0.0214 (9)	0.0085 (9)
N1	0.0492 (12)	0.0397 (12)	0.0626 (13)	−0.0072 (9)	−0.0050 (10)	0.0048 (10)
N2	0.0409 (11)	0.0487 (12)	0.0532 (12)	−0.0168 (9)	−0.0121 (9)	−0.0013 (10)
N3	0.0449 (11)	0.0440 (12)	0.0465 (11)	−0.0167 (9)	−0.0108 (9)	−0.0048 (9)
C1	0.0476 (14)	0.0370 (13)	0.0435 (13)	−0.0120 (11)	−0.0051 (11)	−0.0046 (11)
C2	0.0588 (16)	0.0583 (18)	0.0518 (15)	−0.0190 (13)	−0.0153 (12)	0.0007 (13)
C3	0.0718 (18)	0.0658 (19)	0.0493 (15)	−0.0192 (15)	−0.0151 (13)	0.0042 (13)
C4	0.0654 (17)	0.0535 (17)	0.0539 (16)	−0.0167 (14)	−0.0037 (13)	0.0053 (13)
C5	0.0513 (15)	0.0460 (15)	0.0570 (15)	−0.0179 (12)	−0.0037 (12)	−0.0033 (12)
C6	0.0450 (13)	0.0360 (13)	0.0464 (14)	−0.0074 (11)	−0.0067 (11)	−0.0071 (11)
C7	0.0421 (13)	0.0398 (14)	0.0488 (14)	−0.0104 (11)	−0.0096 (11)	−0.0036 (11)
C8	0.0424 (13)	0.0370 (13)	0.0458 (13)	−0.0080 (10)	−0.0075 (10)	−0.0097 (11)
C9	0.0434 (13)	0.0410 (14)	0.0444 (13)	−0.0110 (11)	−0.0090 (10)	−0.0062 (11)
C10	0.0486 (14)	0.0406 (14)	0.0400 (13)	−0.0101 (11)	−0.0079 (11)	−0.0067 (11)
C11	0.0448 (13)	0.0328 (13)	0.0432 (13)	−0.0106 (10)	−0.0068 (10)	−0.0074 (10)
C12	0.0412 (13)	0.0470 (15)	0.0508 (14)	−0.0121 (11)	−0.0130 (11)	−0.0029 (11)
C13	0.0497 (14)	0.0466 (15)	0.0451 (13)	−0.0089 (11)	−0.0144 (11)	0.0026 (11)
C14	0.0461 (13)	0.0352 (13)	0.0454 (13)	−0.0089 (10)	−0.0059 (10)	−0.0027 (10)
C15	0.0451 (14)	0.0549 (16)	0.0558 (15)	−0.0177 (12)	−0.0139 (12)	0.0011 (12)
C16	0.0512 (14)	0.0498 (15)	0.0442 (13)	−0.0145 (12)	−0.0159 (11)	−0.0002 (11)
C17	0.0370 (13)	0.0494 (16)	0.0531 (15)	−0.0085 (11)	−0.0021 (10)	0.0085 (12)
C18	0.0560 (16)	0.0588 (18)	0.0496 (15)	−0.0128 (13)	−0.0126 (12)	0.0080 (13)
C19	0.0571 (16)	0.0469 (16)	0.0636 (17)	−0.0085 (12)	−0.0108 (13)	0.0092 (13)
C20	0.0492 (15)	0.0635 (19)	0.0523 (16)	−0.0081 (13)	−0.0020 (12)	−0.0003 (14)
C21	0.080 (2)	0.073 (2)	0.0465 (15)	−0.0055 (16)	−0.0112 (14)	0.0076 (15)
C22	0.0700 (18)	0.0550 (18)	0.0550 (17)	−0.0068 (14)	−0.0076 (13)	0.0136 (14)
C23	0.089 (2)	0.076 (2)	0.0697 (19)	−0.0067 (18)	−0.0136 (16)	−0.0136 (17)

Geometric parameters (Å, º)

S1—O2	1.4210 (19)	C9—H9	0.9300
S1—O1	1.4259 (19)	C10—C11	1.488 (3)
S1—N1	1.619 (2)	C11—C16	1.386 (3)
S1—C17	1.752 (3)	C11—C12	1.394 (3)
O3—C10	1.254 (3)	C12—C13	1.380 (3)
O4—C7	1.233 (3)	C12—H12	0.9300
N1—C14	1.426 (3)	C13—C14	1.382 (3)
N1—H1A	0.8600	C13—H13	0.9300
N2—C6	1.392 (3)	C14—C15	1.385 (3)
N2—C7	1.352 (3)	C15—C16	1.374 (3)
N2—H2B	0.8600	C15—H15	0.9300
N3—C1	1.381 (3)	C16—H16	0.9300
N3—C8	1.349 (3)	C17—C22	1.378 (3)
N3—H3C	0.8600	C17—C18	1.390 (3)
C1—C6	1.386 (3)	C18—C19	1.378 (4)
C1—C2	1.391 (3)	C18—H18	0.9300
C2—C3	1.376 (3)	C19—C20	1.381 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.375 (4)	C20—C21	1.384 (4)
C3—H3	0.9300	C20—C23	1.505 (4)
C4—C5	1.378 (3)	C21—C22	1.369 (4)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.391 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—H23A	0.9600
C7—C8	1.488 (3)	C23—H23B	0.9600
C8—C9	1.369 (3)	C23—H23C	0.9600
C9—C10	1.421 (3)
O2—S1—O1	119.98 (12)	C9—C10—C11	120.4 (2)
O2—S1—N1	108.94 (11)	C16—C11—C12	117.8 (2)
O1—S1—N1	104.54 (12)	C16—C11—C10	118.8 (2)
O2—S1—C17	107.94 (12)	C12—C11—C10	123.4 (2)
O1—S1—C17	108.54 (12)	C13—C12—C11	120.4 (2)
N1—S1—C17	106.09 (11)	C13—C12—H12	119.8
C14—N1—S1	126.14 (17)	C11—C12—H12	119.8
C14—N1—H1A	116.9	C12—C13—C14	120.5 (2)
S1—N1—H1A	116.9	C12—C13—H13	119.8
C7—N2—C6	124.63 (19)	C14—C13—H13	119.8
C7—N2—H2B	117.7	C13—C14—C15	119.8 (2)
C6—N2—H2B	117.7	C13—C14—N1	118.8 (2)
C8—N3—C1	124.57 (19)	C15—C14—N1	121.3 (2)
C8—N3—H3C	117.7	C16—C15—C14	119.1 (2)
C1—N3—H3C	117.7	C16—C15—H15	120.5
N3—C1—C2	121.2 (2)	C14—C15—H15	120.5
N3—C1—C6	118.5 (2)	C15—C16—C11	122.3 (2)
C6—C1—C2	120.2 (2)	C15—C16—H16	118.8
C3—C2—C1	118.9 (2)	C11—C16—H16	118.8
C3—C2—H2	120.6	C22—C17—C18	119.8 (3)
C1—C2—H2	120.6	C22—C17—S1	120.1 (2)
C4—C3—C2	121.1 (2)	C18—C17—S1	120.0 (2)
C4—C3—H3	119.4	C19—C18—C17	119.2 (2)
C2—C3—H3	119.4	C19—C18—H18	120.4
C3—C4—C5	120.4 (2)	C17—C18—H18	120.4
C3—C4—H4	119.8	C18—C19—C20	121.9 (3)
C5—C4—H4	119.8	C18—C19—H19	119.1
C4—C5—C6	119.3 (2)	C20—C19—H19	119.1
C4—C5—H5	120.4	C19—C20—C21	117.3 (3)
C6—C5—H5	120.4	C19—C20—C23	120.9 (3)
C1—C6—C5	120.1 (2)	C21—C20—C23	121.8 (3)
C1—C6—N2	118.4 (2)	C22—C21—C20	122.1 (3)
C5—C6—N2	121.5 (2)	C22—C21—H21	118.9
O4—C7—N2	122.5 (2)	C20—C21—H21	118.9
O4—C7—C8	121.2 (2)	C21—C22—C17	119.6 (3)
N2—C7—C8	116.3 (2)	C21—C22—H22	120.2
N3—C8—C7	117.4 (2)	C17—C22—H22	120.2
N3—C8—C9	123.4 (2)	C20—C23—H23A	109.5
C9—C8—C7	119.3 (2)	C20—C23—H23B	109.5
C8—C9—C10	122.1 (2)	H23A—C23—H23B	109.5
C8—C9—H9	118.9	C20—C23—H23C	109.5
C10—C9—H9	118.9	H23A—C23—H23C	109.5
O3—C10—C9	121.7 (2)	H23B—C23—H23C	109.5
O3—C10—C11	117.91 (19)
O2—S1—N1—C14	51.5 (2)	C9—C10—C11—C16	167.2 (2)
O1—S1—N1—C14	−179.05 (19)	O3—C10—C11—C12	166.6 (2)
C17—S1—N1—C14	−64.4 (2)	C9—C10—C11—C12	−14.7 (3)
C8—N3—C1—C6	0.9 (3)	C16—C11—C12—C13	0.3 (3)
C8—N3—C1—C2	−179.6 (2)	C10—C11—C12—C13	−177.8 (2)
N3—C1—C2—C3	−179.0 (2)	C11—C12—C13—C14	1.7 (4)
C6—C1—C2—C3	0.5 (4)	C12—C13—C14—C15	−2.2 (4)
C1—C2—C3—C4	−0.9 (4)	C12—C13—C14—N1	174.7 (2)
C2—C3—C4—C5	1.1 (4)	S1—N1—C14—C13	132.8 (2)
C3—C4—C5—C6	−0.9 (4)	S1—N1—C14—C15	−50.3 (3)
N3—C1—C6—C5	179.1 (2)	C13—C14—C15—C16	0.6 (4)
C2—C1—C6—C5	−0.4 (3)	N1—C14—C15—C16	−176.2 (2)
N3—C1—C6—N2	−0.7 (3)	C14—C15—C16—C11	1.5 (4)
C2—C1—C6—N2	179.7 (2)	C12—C11—C16—C15	−1.9 (3)
C4—C5—C6—C1	0.6 (4)	C10—C11—C16—C15	176.3 (2)
C4—C5—C6—N2	−179.6 (2)	O2—S1—C17—C22	148.5 (2)
C7—N2—C6—C1	−2.0 (3)	O1—S1—C17—C22	17.0 (2)
C7—N2—C6—C5	178.1 (2)	N1—S1—C17—C22	−94.9 (2)
C6—N2—C7—O4	−175.5 (2)	O2—S1—C17—C18	−32.7 (2)
C6—N2—C7—C8	4.3 (3)	O1—S1—C17—C18	−164.22 (19)
C1—N3—C8—C9	−179.5 (2)	N1—S1—C17—C18	83.9 (2)
C1—N3—C8—C7	1.4 (3)	C22—C17—C18—C19	1.9 (4)
O4—C7—C8—N3	175.9 (2)	S1—C17—C18—C19	−176.92 (18)
N2—C7—C8—N3	−3.8 (3)	C17—C18—C19—C20	−1.0 (4)
O4—C7—C8—C9	−3.2 (3)	C18—C19—C20—C21	−0.6 (4)
N2—C7—C8—C9	177.1 (2)	C18—C19—C20—C23	179.0 (2)
N3—C8—C9—C10	−1.1 (4)	C19—C20—C21—C22	1.5 (4)
C7—C8—C9—C10	177.9 (2)	C23—C20—C21—C22	−178.1 (3)
C8—C9—C10—O3	−0.7 (4)	C20—C21—C22—C17	−0.7 (4)
C8—C9—C10—C11	−179.3 (2)	C18—C17—C22—C21	−1.0 (4)
O3—C10—C11—C16	−11.5 (3)	S1—C17—C22—C21	177.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O4^i	0.86	1.98	2.830 (3)	171
N3—H3C···O3	0.86	1.95	2.608 (3)	132

Symmetry code: (i) −x+3, −y+1, −z.