4-Di­methyl­amino-4'-nitro­benzo­phenone

In the crystal structure of the title compound, C₁₅H₁₄N₂O₃, the two halves of the mol­ecule, except for the central CO group, are nearly planar and the dihedral angle between the least-squares planes through the C atoms of the six-membered rings is 51.41 (6)°. The central O atom is displaced by -0.7389 (15) and 0.5439 (15) Å from these least-squares planes.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.089
• Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

(I)

Crystal data

C15H14N2O3	F(000) = 568
Mr = 270.28	Dx = 1.358 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.1527 (3) Å	Cell parameters from 8954 reflections
b = 28.9053 (15) Å	θ = 3.1–25.4°
c = 7.4404 (4) Å	µ = 0.10 mm^−1
β = 92.036 (2)°	T = 291 K
V = 1322.41 (12) Å^3	Plate, yellow
Z = 4	0.50 × 0.20 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer	1021 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 25.4°, θmin = 3.1°
Detector resolution: 10 vertical, 18 horizontal pixels mm^-1	h = −7→7
375 frames via ω–rotation (Δω=1°) with three sets at different κ–angles and two times 70 s per frame scans	k = −34→34
8954 measured reflections	l = −8→8
2365 independent 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.025P)^2] where P = (Fo^2 + 2Fc^2)/3
2365 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.16 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
O1	0.4930 (3)	0.04323 (6)	0.1647 (3)	0.1152 (7)
O2	0.7623 (3)	0.07143 (6)	0.3120 (3)	0.1258 (8)
O3	−0.0488 (2)	0.24747 (5)	0.2686 (2)	0.0733 (5)
N1	0.5822 (4)	0.07523 (7)	0.2424 (3)	0.0756 (7)
N2	0.5282 (3)	0.42852 (6)	0.2350 (2)	0.0650 (6)
C1	0.4748 (4)	0.12028 (7)	0.2442 (3)	0.0512 (6)
C2	0.2708 (4)	0.12473 (8)	0.1620 (3)	0.0585 (6)
H2	0.2026	0.0996	0.1058	0.070*
C3	0.1716 (3)	0.16737 (8)	0.1658 (3)	0.0556 (6)
H3	0.0336	0.1709	0.1126	0.067*
C4	0.2728 (3)	0.20510 (7)	0.2471 (3)	0.0449 (6)
C5	0.4788 (3)	0.19933 (7)	0.3275 (3)	0.0505 (6)
H5	0.5491	0.2244	0.3821	0.061*
C6	0.5792 (3)	0.15682 (8)	0.3267 (3)	0.0540 (6)
H6	0.7163	0.1529	0.3815	0.065*
C7	0.1501 (4)	0.24968 (7)	0.2581 (2)	0.0502 (6)
C8	0.2611 (3)	0.29487 (7)	0.2586 (3)	0.0456 (6)
C9	0.1526 (3)	0.33340 (8)	0.3222 (3)	0.0545 (6)
H9	0.0166	0.3294	0.3707	0.065*
C10	0.2386 (4)	0.37673 (8)	0.3160 (3)	0.0571 (6)
H10	0.1615	0.4015	0.3621	0.069*
C11	0.4424 (4)	0.38489 (8)	0.2408 (3)	0.0506 (6)
C12	0.5506 (3)	0.34610 (8)	0.1762 (3)	0.0520 (6)
H12	0.6849	0.3500	0.1246	0.062*
C13	0.4642 (3)	0.30262 (7)	0.1867 (3)	0.0490 (6)
H13	0.5429	0.2776	0.1448	0.059*
C14	0.3969 (4)	0.46812 (8)	0.2798 (3)	0.0973 (9)
H14A	0.2728	0.4699	0.1982	0.146*
H14B	0.4819	0.4958	0.2705	0.146*
H14C	0.3490	0.4650	0.4006	0.146*
C15	0.7210 (4)	0.43779 (8)	0.1359 (4)	0.0925 (9)
H15A	0.8321	0.4158	0.1698	0.139*
H15B	0.7719	0.4685	0.1626	0.139*
H15C	0.6873	0.4352	0.0093	0.139*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1163 (16)	0.0603 (13)	0.169 (2)	−0.0082 (11)	−0.0007 (14)	−0.0205 (13)
O2	0.1129 (17)	0.0873 (16)	0.174 (2)	0.0381 (12)	−0.0447 (15)	−0.0227 (13)
O3	0.0397 (9)	0.0741 (12)	0.1064 (13)	−0.0007 (8)	0.0084 (9)	0.0080 (9)
N1	0.0784 (18)	0.0601 (17)	0.0885 (18)	0.0047 (14)	0.0068 (14)	−0.0010 (13)
N2	0.0671 (14)	0.0508 (14)	0.0772 (15)	−0.0019 (12)	0.0045 (12)	−0.0035 (11)
C1	0.0541 (16)	0.0462 (15)	0.0538 (16)	−0.0009 (13)	0.0077 (13)	0.0031 (12)
C2	0.0573 (17)	0.0578 (17)	0.0603 (16)	−0.0155 (13)	0.0025 (13)	−0.0045 (13)
C3	0.0452 (14)	0.0644 (17)	0.0569 (16)	−0.0073 (13)	−0.0002 (11)	0.0024 (13)
C4	0.0396 (14)	0.0542 (16)	0.0410 (15)	−0.0032 (12)	0.0048 (11)	0.0033 (11)
C5	0.0470 (15)	0.0531 (17)	0.0513 (16)	−0.0004 (12)	−0.0023 (12)	−0.0028 (11)
C6	0.0468 (15)	0.0563 (16)	0.0585 (16)	−0.0008 (13)	−0.0027 (12)	0.0042 (12)
C7	0.0435 (15)	0.0638 (17)	0.0432 (14)	0.0034 (14)	0.0026 (12)	0.0061 (12)
C8	0.0389 (15)	0.0544 (16)	0.0434 (16)	0.0009 (13)	0.0007 (11)	0.0017 (11)
C9	0.0435 (15)	0.0663 (17)	0.0542 (15)	0.0073 (14)	0.0080 (12)	−0.0018 (13)
C10	0.0578 (17)	0.0557 (17)	0.0581 (16)	0.0098 (13)	0.0050 (13)	−0.0074 (13)
C11	0.0540 (17)	0.0526 (16)	0.0448 (15)	0.0035 (13)	−0.0053 (12)	0.0002 (12)
C12	0.0436 (14)	0.0565 (17)	0.0560 (16)	0.0000 (13)	0.0046 (11)	−0.0013 (12)
C13	0.0440 (15)	0.0519 (16)	0.0512 (15)	0.0068 (12)	0.0013 (12)	−0.0006 (12)
C14	0.116 (2)	0.059 (2)	0.118 (2)	0.0028 (16)	0.0220 (18)	−0.0128 (16)
C15	0.075 (2)	0.071 (2)	0.133 (3)	−0.0127 (14)	0.0178 (18)	0.0040 (17)

Geometric parameters (Å, º)

O1—N1	1.212 (2)	C7—C8	1.474 (3)
O2—N1	1.211 (2)	C8—C9	1.390 (3)
O3—C7	1.2306 (19)	C8—C13	1.395 (2)
N1—C1	1.461 (3)	C9—C10	1.361 (3)
N2—C11	1.368 (3)	C9—H9	0.9300
N2—C15	1.444 (2)	C10—C11	1.411 (2)
N2—C14	1.447 (2)	C10—H10	0.9300
C1—C6	1.370 (2)	C11—C12	1.398 (3)
C1—C2	1.382 (2)	C12—C13	1.368 (2)
C2—C3	1.376 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.384 (2)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.392 (2)	C14—H14C	0.9600
C4—C7	1.497 (3)	C15—H15A	0.9600
C5—C6	1.375 (2)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300
O2—N1—O1	121.8 (2)	C13—C8—C7	124.2 (2)
O2—N1—C1	119.0 (2)	C10—C9—C8	122.2 (2)
O1—N1—C1	119.2 (2)	C10—C9—H9	118.9
C11—N2—C15	120.8 (2)	C8—C9—H9	118.9
C11—N2—C14	120.2 (2)	C9—C10—C11	121.3 (2)
C15—N2—C14	116.52 (19)	C9—C10—H10	119.3
C6—C1—C2	122.0 (2)	C11—C10—H10	119.3
C6—C1—N1	119.1 (2)	N2—C11—C12	122.7 (2)
C2—C1—N1	118.9 (2)	N2—C11—C10	121.1 (2)
C3—C2—C1	118.06 (19)	C12—C11—C10	116.3 (2)
C3—C2—H2	121.0	C13—C12—C11	121.8 (2)
C1—C2—H2	121.0	C13—C12—H12	119.1
C2—C3—C4	121.46 (19)	C11—C12—H12	119.1
C2—C3—H3	119.3	C12—C13—C8	121.6 (2)
C4—C3—H3	119.3	C12—C13—H13	119.2
C3—C4—C5	118.8 (2)	C8—C13—H13	119.2
C3—C4—C7	118.83 (19)	N2—C14—H14A	109.5
C5—C4—C7	122.19 (19)	N2—C14—H14B	109.5
C6—C5—C4	120.48 (19)	H14A—C14—H14B	109.5
C6—C5—H5	119.8	N2—C14—H14C	109.5
C4—C5—H5	119.8	H14A—C14—H14C	109.5
C1—C6—C5	119.1 (2)	H14B—C14—H14C	109.5
C1—C6—H6	120.4	N2—C15—H15A	109.5
C5—C6—H6	120.4	N2—C15—H15B	109.5
O3—C7—C8	120.5 (2)	H15A—C15—H15B	109.5
O3—C7—C4	117.6 (2)	N2—C15—H15C	109.5
C8—C7—C4	121.91 (19)	H15A—C15—H15C	109.5
C9—C8—C13	116.7 (2)	H15B—C15—H15C	109.5
C9—C8—C7	118.9 (2)
O2—N1—C1—C6	−0.9 (3)	O3—C7—C8—C9	18.5 (3)
O1—N1—C1—C6	−177.7 (2)	C4—C7—C8—C9	−160.83 (17)
O2—N1—C1—C2	178.9 (2)	O3—C7—C8—C13	−156.55 (18)
O1—N1—C1—C2	2.1 (3)	C4—C7—C8—C13	24.2 (3)
C6—C1—C2—C3	−0.5 (3)	C13—C8—C9—C10	−0.2 (3)
N1—C1—C2—C3	179.69 (19)	C7—C8—C9—C10	−175.58 (18)
C1—C2—C3—C4	0.8 (3)	C8—C9—C10—C11	1.2 (3)
C2—C3—C4—C5	−0.4 (3)	C15—N2—C11—C12	9.7 (3)
C2—C3—C4—C7	−175.75 (19)	C14—N2—C11—C12	171.18 (19)
C3—C4—C5—C6	−0.3 (3)	C15—N2—C11—C10	−171.19 (18)
C7—C4—C5—C6	174.82 (18)	C14—N2—C11—C10	−9.7 (3)
C2—C1—C6—C5	−0.2 (3)	C9—C10—C11—N2	−179.98 (19)
N1—C1—C6—C5	179.58 (18)	C9—C10—C11—C12	−0.8 (3)
C4—C5—C6—C1	0.6 (3)	N2—C11—C12—C13	178.61 (18)
C3—C4—C7—O3	30.5 (3)	C10—C11—C12—C13	−0.6 (3)
C5—C4—C7—O3	−144.68 (19)	C11—C12—C13—C8	1.6 (3)
C3—C4—C7—C8	−150.25 (18)	C9—C8—C13—C12	−1.2 (3)
C5—C4—C7—C8	34.6 (3)	C7—C8—C13—C12	173.94 (18)