7,8-Dimethyl-11H-indeno­[1,2-b]quinoxalin-11-one

In the title compound, C₁₇H₁₂N₂O, the mean planes of the indene ring and quinoxaline system (r.m.s. deviations = 0.0131 and 0.0082 Å) are approximately parallel to one another, making a dihedral angle of 1.2 (5)°. This means that the indeno­[1,2-b]quinoxaline ring is almost in the same plane (r.m.s. deviation = 0.0181 Å).

Key indicators

• Single-crystal X-ray study
• T = 282 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.060
• wR factor = 0.153
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.935 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         16 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         10 Note
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         43 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

7,8-Dimethyl-11H-indeno[1,2-b]quinoxalin-11-one

Crystal data

C17H12N2O	F(000) = 544
Mr = 260.29	Dx = 1.349 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4548 (9) Å	Cell parameters from 5967 reflections
b = 22.976 (3) Å	θ = 2.7–28.4°
c = 8.3149 (10) Å	µ = 0.09 mm^−1
β = 115.866 (3)°	T = 282 K
V = 1281.5 (3) Å^3	Block, colorless
Z = 4	0.45 × 0.3 × 0.22 mm

Data collection

Bruker SMART CCD 6000 area detector diffractometer	3134 independent reflections
Radiation source: sealed X-ray tube	2437 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 5.6 pixels mm^-1	θmax = 28.4°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −30→30
Tmin = 0.606, Tmax = 0.746	l = −11→5
10114 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.7679P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3134 reflections	Δρmax = 0.27 e Å^−3
183 parameters	Δρmin = −0.22 e Å^−3
0 restraints

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	0.1899 (2)	0.67104 (6)	0.38760 (19)	0.0613 (4)
N1	0.1135 (2)	0.54175 (6)	0.3195 (2)	0.0400 (4)
N2	0.3665 (2)	0.48258 (6)	0.6458 (2)	0.0417 (4)
C1	0.3614 (2)	0.53906 (7)	0.6270 (2)	0.0348 (4)
C2	0.4780 (2)	0.58312 (7)	0.7599 (2)	0.0366 (4)
C3	0.6183 (3)	0.57743 (9)	0.9349 (3)	0.0483 (5)
H3	0.6505	0.5411	0.9892	0.058*
C4	0.7104 (3)	0.62748 (10)	1.0279 (3)	0.0542 (5)
H4	0.8068	0.6244	1.1455	0.065*
C5	0.6616 (3)	0.68157 (9)	0.9493 (3)	0.0517 (5)
H5	0.7257	0.7144	1.0146	0.062*
C6	0.5187 (3)	0.68793 (8)	0.7744 (3)	0.0463 (5)
H6	0.4851	0.7245	0.7217	0.056*
C7	0.4275 (3)	0.63822 (8)	0.6807 (2)	0.0381 (4)
C8	0.2716 (3)	0.63268 (7)	0.4928 (2)	0.0400 (4)
C9	0.2358 (2)	0.56799 (7)	0.4648 (2)	0.0362 (4)
C10	0.1132 (3)	0.48201 (7)	0.3342 (2)	0.0381 (4)
C11	−0.0140 (3)	0.44895 (8)	0.1861 (3)	0.0448 (4)
H11	−0.0943	0.4680	0.0802	0.054*
C12	−0.0229 (3)	0.38935 (8)	0.1933 (3)	0.0490 (5)
C13	0.1007 (3)	0.36040 (8)	0.3545 (3)	0.0528 (5)
C14	0.2283 (3)	0.39190 (8)	0.4996 (3)	0.0500 (5)
H14	0.3106	0.3723	0.6037	0.060*
C15	0.2382 (3)	0.45313 (7)	0.4951 (2)	0.0389 (4)
C16	0.0931 (4)	0.29501 (9)	0.3674 (4)	0.0773 (8)
H16A	0.1901	0.2825	0.4830	0.116*
H16B	0.1219	0.2775	0.2765	0.116*
H16C	−0.0375	0.2834	0.3511	0.116*
C17	−0.1623 (4)	0.35635 (10)	0.0302 (4)	0.0665 (7)
H17A	−0.2286	0.3831	−0.0665	0.100*
H17B	−0.2595	0.3362	0.0560	0.100*
H17C	−0.0878	0.3287	−0.0030	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0802 (11)	0.0335 (7)	0.0499 (8)	0.0066 (7)	0.0095 (7)	0.0056 (6)
N1	0.0444 (8)	0.0322 (7)	0.0406 (8)	0.0024 (6)	0.0159 (7)	0.0001 (6)
N2	0.0491 (9)	0.0341 (7)	0.0459 (9)	0.0071 (6)	0.0245 (7)	0.0067 (6)
C1	0.0365 (8)	0.0343 (8)	0.0375 (9)	0.0055 (6)	0.0197 (7)	0.0032 (7)
C2	0.0345 (8)	0.0395 (9)	0.0381 (9)	0.0041 (7)	0.0179 (7)	−0.0004 (7)
C3	0.0451 (10)	0.0541 (11)	0.0408 (10)	0.0099 (8)	0.0143 (8)	0.0063 (8)
C4	0.0406 (10)	0.0733 (14)	0.0405 (10)	0.0042 (9)	0.0102 (8)	−0.0085 (10)
C5	0.0409 (10)	0.0557 (12)	0.0533 (12)	−0.0030 (8)	0.0157 (9)	−0.0163 (9)
C6	0.0435 (10)	0.0409 (10)	0.0517 (11)	0.0003 (8)	0.0182 (9)	−0.0077 (8)
C7	0.0371 (9)	0.0388 (9)	0.0399 (9)	0.0026 (7)	0.0181 (8)	−0.0024 (7)
C8	0.0463 (10)	0.0313 (8)	0.0395 (9)	0.0029 (7)	0.0161 (8)	−0.0019 (7)
C9	0.0386 (8)	0.0317 (8)	0.0389 (9)	0.0030 (6)	0.0175 (7)	0.0015 (7)
C10	0.0419 (9)	0.0337 (8)	0.0457 (10)	−0.0001 (7)	0.0257 (8)	−0.0023 (7)
C11	0.0485 (10)	0.0413 (10)	0.0499 (11)	−0.0045 (8)	0.0264 (9)	−0.0078 (8)
C12	0.0565 (11)	0.0417 (10)	0.0663 (13)	−0.0115 (8)	0.0429 (11)	−0.0148 (9)
C13	0.0715 (13)	0.0330 (9)	0.0784 (15)	−0.0068 (9)	0.0554 (12)	−0.0073 (9)
C14	0.0690 (13)	0.0325 (9)	0.0617 (12)	0.0054 (8)	0.0408 (11)	0.0060 (8)
C15	0.0467 (9)	0.0320 (8)	0.0488 (10)	0.0026 (7)	0.0308 (8)	0.0015 (7)
C16	0.114 (2)	0.0324 (10)	0.112 (2)	−0.0109 (12)	0.0750 (19)	−0.0078 (12)
C17	0.0766 (15)	0.0572 (13)	0.0820 (17)	−0.0262 (11)	0.0497 (14)	−0.0305 (12)

Geometric parameters (Å, º)

O1—C8	1.203 (2)	C8—C9	1.510 (2)
N1—C9	1.301 (2)	C10—C11	1.405 (2)
N1—C10	1.378 (2)	C10—C15	1.418 (3)
N2—C1	1.306 (2)	C11—H11	0.9300
N2—C15	1.377 (2)	C11—C12	1.374 (3)
C1—C2	1.471 (2)	C12—C13	1.418 (3)
C1—C9	1.427 (2)	C12—C17	1.505 (3)
C2—C3	1.378 (3)	C13—C14	1.372 (3)
C2—C7	1.401 (2)	C13—C16	1.509 (3)
C3—H3	0.9300	C14—H14	0.9300
C3—C4	1.389 (3)	C14—C15	1.410 (2)
C4—H4	0.9300	C16—H16A	0.9600
C4—C5	1.377 (3)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C5—C6	1.385 (3)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C6—C7	1.382 (2)	C17—H17C	0.9600
C7—C8	1.491 (2)
C9—N1—C10	114.01 (15)	N1—C10—C15	121.59 (16)
C1—N2—C15	114.02 (15)	C11—C10—C15	119.23 (16)
N2—C1—C2	128.14 (16)	C10—C11—H11	119.1
N2—C1—C9	123.29 (16)	C12—C11—C10	121.88 (19)
C9—C1—C2	108.57 (14)	C12—C11—H11	119.1
C3—C2—C1	130.93 (17)	C11—C12—C13	118.99 (18)
C3—C2—C7	120.44 (17)	C11—C12—C17	119.4 (2)
C7—C2—C1	108.62 (15)	C13—C12—C17	121.62 (19)
C2—C3—H3	120.9	C12—C13—C16	120.3 (2)
C2—C3—C4	118.18 (19)	C14—C13—C12	119.94 (17)
C4—C3—H3	120.9	C14—C13—C16	119.7 (2)
C3—C4—H4	119.4	C13—C14—H14	119.1
C5—C4—C3	121.26 (19)	C13—C14—C15	121.82 (19)
C5—C4—H4	119.4	C15—C14—H14	119.1
C4—C5—H5	119.5	N2—C15—C10	122.55 (15)
C4—C5—C6	121.09 (19)	N2—C15—C14	119.32 (17)
C6—C5—H5	119.5	C14—C15—C10	118.13 (17)
C5—C6—H6	121.0	C13—C16—H16A	109.5
C7—C6—C5	117.92 (18)	C13—C16—H16B	109.5
C7—C6—H6	121.0	C13—C16—H16C	109.5
C2—C7—C8	110.02 (15)	H16A—C16—H16B	109.5
C6—C7—C2	121.10 (17)	H16A—C16—H16C	109.5
C6—C7—C8	128.89 (17)	H16B—C16—H16C	109.5
O1—C8—C7	127.95 (16)	C12—C17—H17A	109.5
O1—C8—C9	127.57 (17)	C12—C17—H17B	109.5
C7—C8—C9	104.47 (14)	C12—C17—H17C	109.5
N1—C9—C1	124.53 (15)	H17A—C17—H17B	109.5
N1—C9—C8	127.17 (15)	H17A—C17—H17C	109.5
C1—C9—C8	108.30 (14)	H17B—C17—H17C	109.5
N1—C10—C11	119.18 (16)
O1—C8—C9—N1	2.1 (3)	C6—C7—C8—C9	178.41 (18)
O1—C8—C9—C1	−178.2 (2)	C7—C2—C3—C4	−1.4 (3)
N1—C10—C11—C12	−179.08 (17)	C7—C8—C9—N1	−179.01 (17)
N1—C10—C15—N2	0.1 (3)	C7—C8—C9—C1	0.66 (18)
N1—C10—C15—C14	179.67 (16)	C9—N1—C10—C11	179.60 (16)
N2—C1—C2—C3	−0.6 (3)	C9—N1—C10—C15	−0.4 (2)
N2—C1—C2—C7	178.74 (17)	C9—C1—C2—C3	179.88 (18)
N2—C1—C9—N1	0.2 (3)	C9—C1—C2—C7	−0.79 (19)
N2—C1—C9—C8	−179.51 (16)	C10—N1—C9—C1	0.3 (2)
C1—N2—C15—C10	0.3 (2)	C10—N1—C9—C8	179.93 (16)
C1—N2—C15—C14	−179.21 (16)	C10—C11—C12—C13	−0.4 (3)
C1—C2—C3—C4	177.84 (18)	C10—C11—C12—C17	179.93 (17)
C1—C2—C7—C6	−178.38 (16)	C11—C10—C15—N2	−179.92 (16)
C1—C2—C7—C8	1.22 (19)	C11—C10—C15—C14	−0.4 (2)
C2—C1—C9—N1	179.72 (16)	C11—C12—C13—C14	−0.7 (3)
C2—C1—C9—C8	0.04 (18)	C11—C12—C13—C16	179.44 (19)
C2—C3—C4—C5	0.9 (3)	C12—C13—C14—C15	1.3 (3)
C2—C7—C8—O1	177.7 (2)	C13—C14—C15—N2	178.80 (17)
C2—C7—C8—C9	−1.16 (19)	C13—C14—C15—C10	−0.8 (3)
C3—C2—C7—C6	1.0 (3)	C15—N2—C1—C2	−179.95 (15)
C3—C2—C7—C8	−179.36 (16)	C15—N2—C1—C9	−0.5 (2)
C3—C4—C5—C6	0.0 (3)	C15—C10—C11—C12	1.0 (3)
C4—C5—C6—C7	−0.5 (3)	C16—C13—C14—C15	−178.83 (19)
C5—C6—C7—C2	−0.1 (3)	C17—C12—C13—C14	178.92 (18)
C5—C6—C7—C8	−179.59 (18)	C17—C12—C13—C16	−0.9 (3)
C6—C7—C8—O1	−2.7 (3)