N-(4-Bromo­phen­acyl)-4,6-di­methyl-2-oxo-1,2-di­hydro­pyridine-2-carbo­nitrile

The title compound, C₁₆H₁₃BrN₂O₂, was synthesized and characterized by ¹H NMR and X-ray diffraction techniques.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.107
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C31     ..       5.82 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C31    ...       1.44 Ang.

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1998).

N-(4-Bromophenacyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-2-carbonitrile

Crystal data

C16H13BrN2O2	F(000) = 696
Mr = 345.19	Dx = 1.565 Mg m^−3
Monoclinic, P21/c	Melting point: 498 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.5418 Å
a = 9.5667 (16) Å	Cell parameters from 25 reflections
b = 7.3784 (12) Å	θ = 33–35°
c = 20.850 (4) Å	µ = 3.88 mm^−1
β = 95.34 (1)°	T = 293 K
V = 1465.4 (4) Å^3	Prism, orange
Z = 4	0.15 × 0.15 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 74.9°, θmin = 4.3°
Graphite monochromator	h = −11→11
non–profiled ω/2θ scans	k = 0→9
3007 measured reflections	l = 0→26
3007 independent reflections	1 standard reflections every 200 reflections
2444 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.9586P] where P = (Fo^2 + 2Fc^2)/3
3007 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	1.05459 (4)	0.73593 (5)	1.128233 (14)	0.06055 (14)
N1	0.7628 (2)	0.7172 (3)	0.73457 (10)	0.0392 (5)
C2	0.7629 (2)	0.5493 (4)	0.70392 (12)	0.0400 (5)
O2	0.8463 (2)	0.4294 (3)	0.72294 (10)	0.0539 (5)
C3	0.6589 (3)	0.5289 (4)	0.64915 (12)	0.0400 (5)
C31	0.6579 (3)	0.3594 (4)	0.61530 (13)	0.0461 (6)
N31	0.6560 (3)	0.2282 (4)	0.58611 (15)	0.0631 (7)
C4	0.5647 (3)	0.6634 (4)	0.63052 (12)	0.0442 (6)
C41	0.4545 (3)	0.6409 (6)	0.57453 (15)	0.0624 (9)
H41A	0.4889	0.6896	0.5363	0.094*
H41B	0.3708	0.7044	0.5834	0.094*
H41C	0.4337	0.5145	0.5683	0.094*
C5	0.5737 (3)	0.8280 (4)	0.66380 (13)	0.0465 (6)
H5	0.5124	0.9215	0.6507	0.056*
C6	0.6707 (3)	0.8540 (4)	0.71506 (12)	0.0421 (6)
C61	0.6810 (4)	1.0319 (4)	0.74931 (16)	0.0602 (8)
H61A	0.6088	1.1116	0.7308	0.090*
H61B	0.7713	1.0849	0.7451	0.090*
H61C	0.6694	1.0136	0.7941	0.090*
C7	0.8551 (3)	0.7348 (4)	0.79407 (12)	0.0425 (6)
H7A	0.8963	0.8550	0.7966	0.051*
H7B	0.9306	0.6469	0.7944	0.051*
C8	0.7713 (3)	0.7030 (4)	0.85184 (13)	0.0421 (6)
O8	0.6472 (2)	0.6698 (4)	0.84343 (11)	0.0668 (7)
C9	0.8439 (3)	0.7154 (4)	0.91781 (12)	0.0395 (5)
C10	0.9836 (3)	0.7680 (4)	0.92952 (13)	0.0444 (6)
H10	1.0348	0.7986	0.8953	0.053*
C11	1.0469 (3)	0.7751 (4)	0.99224 (14)	0.0495 (7)
H11	1.1401	0.8107	1.0002	0.059*
C12	0.9702 (3)	0.7288 (4)	1.04232 (13)	0.0456 (6)
C13	0.8315 (3)	0.6747 (5)	1.03151 (14)	0.0520 (7)
H13	0.7812	0.6420	1.0658	0.062*
C14	0.7689 (3)	0.6698 (5)	0.96936 (14)	0.0511 (7)
H14	0.6752	0.6356	0.9618	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0690 (2)	0.0720 (2)	0.03908 (19)	0.00808 (17)	−0.00372 (14)	−0.00731 (15)
N1	0.0293 (9)	0.0517 (13)	0.0361 (10)	−0.0026 (9)	0.0006 (8)	−0.0003 (9)
C2	0.0302 (11)	0.0491 (14)	0.0411 (13)	0.0023 (11)	0.0057 (10)	0.0003 (11)
O2	0.0408 (10)	0.0580 (12)	0.0609 (12)	0.0114 (9)	−0.0053 (9)	0.0030 (10)
C3	0.0334 (12)	0.0491 (14)	0.0380 (12)	−0.0011 (11)	0.0055 (10)	−0.0045 (11)
C31	0.0372 (13)	0.0589 (17)	0.0425 (14)	0.0031 (12)	0.0042 (11)	−0.0013 (13)
N31	0.0643 (17)	0.0674 (18)	0.0586 (16)	0.0006 (14)	0.0105 (13)	−0.0151 (14)
C4	0.0351 (13)	0.0615 (16)	0.0357 (13)	0.0035 (12)	0.0017 (10)	−0.0008 (12)
C41	0.0520 (17)	0.085 (2)	0.0465 (16)	0.0129 (17)	−0.0129 (13)	−0.0083 (16)
C5	0.0414 (14)	0.0554 (16)	0.0419 (14)	0.0125 (12)	0.0008 (11)	0.0037 (13)
C6	0.0400 (13)	0.0466 (14)	0.0401 (13)	−0.0003 (11)	0.0055 (11)	0.0014 (11)
C61	0.071 (2)	0.0530 (17)	0.0557 (18)	0.0007 (16)	0.0015 (16)	−0.0048 (15)
C7	0.0278 (11)	0.0599 (16)	0.0393 (13)	−0.0068 (11)	−0.0004 (9)	−0.0001 (12)
C8	0.0316 (12)	0.0515 (15)	0.0428 (14)	−0.0074 (11)	0.0011 (10)	0.0010 (11)
O8	0.0326 (10)	0.113 (2)	0.0537 (12)	−0.0228 (12)	−0.0011 (9)	0.0096 (13)
C9	0.0329 (12)	0.0465 (14)	0.0391 (13)	−0.0009 (10)	0.0037 (10)	−0.0026 (11)
C10	0.0334 (12)	0.0590 (17)	0.0406 (13)	−0.0067 (12)	0.0021 (10)	−0.0004 (12)
C11	0.0363 (13)	0.0660 (19)	0.0450 (15)	−0.0052 (13)	−0.0029 (11)	−0.0052 (13)
C12	0.0476 (14)	0.0510 (16)	0.0377 (13)	0.0066 (12)	0.0020 (11)	−0.0042 (11)
C13	0.0468 (15)	0.0666 (18)	0.0439 (14)	−0.0002 (14)	0.0123 (12)	0.0037 (14)
C14	0.0361 (13)	0.0685 (19)	0.0489 (15)	−0.0062 (13)	0.0051 (11)	0.0011 (14)

Geometric parameters (Å, º)

Br1—C12	1.896 (3)	C61—H61B	0.9600
N1—C6	1.376 (3)	C61—H61C	0.9600
N1—C2	1.394 (3)	C7—C8	1.526 (4)
N1—C7	1.460 (3)	C7—H7A	0.9700
C2—O2	1.232 (3)	C7—H7B	0.9700
C2—C3	1.451 (3)	C8—O8	1.209 (3)
C3—C4	1.372 (4)	C8—C9	1.485 (4)
C3—C31	1.436 (4)	C9—C14	1.388 (4)
C31—N31	1.142 (4)	C9—C10	1.391 (4)
C4—C5	1.397 (4)	C10—C11	1.390 (4)
C4—C41	1.507 (4)	C10—H10	0.9300
C41—H41A	0.9600	C11—C12	1.374 (4)
C41—H41B	0.9600	C11—H11	0.9300
C41—H41C	0.9600	C12—C13	1.384 (4)
C5—C6	1.362 (4)	C13—C14	1.376 (4)
C5—H5	0.9300	C13—H13	0.9300
C6—C61	1.493 (4)	C14—H14	0.9300
C61—H61A	0.9600
C6—N1—C2	123.0 (2)	H61A—C61—H61C	109.5
C6—N1—C7	120.4 (2)	H61B—C61—H61C	109.5
C2—N1—C7	116.2 (2)	N1—C7—C8	109.6 (2)
O2—C2—N1	121.2 (2)	N1—C7—H7A	109.7
O2—C2—C3	123.7 (3)	C8—C7—H7A	109.7
N1—C2—C3	115.1 (2)	N1—C7—H7B	109.7
C4—C3—C31	121.1 (2)	C8—C7—H7B	109.7
C4—C3—C2	122.1 (2)	H7A—C7—H7B	108.2
C31—C3—C2	116.8 (2)	O8—C8—C9	121.0 (2)
N31—C31—C3	177.3 (3)	O8—C8—C7	119.8 (2)
C3—C4—C5	118.7 (2)	C9—C8—C7	119.1 (2)
C3—C4—C41	122.2 (3)	C14—C9—C10	119.3 (3)
C5—C4—C41	119.1 (3)	C14—C9—C8	118.1 (2)
C4—C41—H41A	109.5	C10—C9—C8	122.6 (2)
C4—C41—H41B	109.5	C11—C10—C9	120.1 (3)
H41A—C41—H41B	109.5	C11—C10—H10	119.9
C4—C41—H41C	109.5	C9—C10—H10	119.9
H41A—C41—H41C	109.5	C12—C11—C10	119.3 (3)
H41B—C41—H41C	109.5	C12—C11—H11	120.4
C6—C5—C4	121.2 (3)	C10—C11—H11	120.4
C6—C5—H5	119.4	C11—C12—C13	121.3 (3)
C4—C5—H5	119.4	C11—C12—Br1	120.0 (2)
C5—C6—N1	119.9 (3)	C13—C12—Br1	118.7 (2)
C5—C6—C61	120.6 (3)	C14—C13—C12	119.2 (3)
N1—C6—C61	119.4 (2)	C14—C13—H13	120.4
C6—C61—H61A	109.5	C12—C13—H13	120.4
C6—C61—H61B	109.5	C13—C14—C9	120.8 (3)
H61A—C61—H61B	109.5	C13—C14—H14	119.6
C6—C61—H61C	109.5	C9—C14—H14	119.6