1-[(2,4-Di­chloro­benzoyl)­methyl]-4-(N,N-di­methyl­amino)­pyridinium bromide

In the title compound, C₁₅H₁₅Cl₂N₂O⁺·Br⁻, the angle between the least-squares planes of the di­chloro­phenyl moiety and the pyridine ring is 20.23 (9)°. The molecular packing is mainly influenced by intermolecular C—H...Br hydrogen-bond interactions. The mol­ecules form an extended chain along the b axis, through C—H...Br hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.026
• wR factor = 0.071
• Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br     ..  Cl1     ..       3.56 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8C    ..  CL2     ..       2.94 Ang.

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Version 1.64.02; Farrugia, 1999) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-[(2,4-Dichlorobenzoyl)methyl]-4-(N,N-dimethylamino)pyridinium bromide

Crystal data

C15H15Cl2N2O^+·Br^−	F(000) = 784
Mr = 390.10	Dx = 1.572 Mg m^−3
Monoclinic, P21/n	Melting point: 534 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.6148 (16) Å	Cell parameters from 938 reflections
b = 8.9986 (16) Å	θ = 2.5–29.1°
c = 19.437 (3) Å	µ = 2.82 mm^−1
β = 101.399 (5)°	T = 298 K
V = 1648.5 (5) Å^3	Block, colourless
Z = 4	0.60 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD 1K diffractometer	3638 independent reflections
Radiation source: fine-focus sealed tube	3067 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
ω scans	θmax = 27.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −12→12
Tmin = 0.250, Tmax = 0.430	k = 0→11
3638 measured reflections	l = 0→24

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 0.6372P] where P = (Fo^2 + 2Fc^2)/3
3638 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.46 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
Br	0.61819 (2)	0.66051 (2)	0.153948 (10)	0.04347 (8)
Cl1	−0.04280 (6)	0.82936 (9)	0.20833 (3)	0.0699 (2)
Cl2	0.33622 (6)	0.98638 (8)	0.43701 (3)	0.06127 (17)
O1	0.57267 (17)	0.7485 (2)	0.43658 (8)	0.0650 (5)
N1	0.80308 (16)	0.75552 (19)	0.37129 (8)	0.0392 (4)
N2	1.18425 (18)	0.5563 (2)	0.45792 (9)	0.0472 (4)
C1	0.6691 (2)	0.8268 (2)	0.33874 (11)	0.0439 (5)
H1A	0.6427	0.7948	0.2903	0.053*
H1B	0.6825	0.9337	0.3389	0.053*
C2	0.8486 (2)	0.6349 (2)	0.34106 (11)	0.0449 (5)
H2	0.7933	0.5979	0.2999	0.054*
C3	0.9716 (2)	0.5662 (2)	0.36857 (11)	0.0458 (5)
H3	0.9997	0.4834	0.3462	0.055*
C4	1.0587 (2)	0.6192 (2)	0.43152 (10)	0.0385 (4)
C5	1.0047 (2)	0.7414 (2)	0.46344 (10)	0.0406 (4)
H5	1.0546	0.7776	0.5060	0.049*
C6	0.8808 (2)	0.8064 (2)	0.43267 (11)	0.0413 (4)
H6	0.8482	0.8881	0.4542	0.050*
C7	1.2401 (3)	0.4371 (3)	0.42053 (14)	0.0692 (7)
H7A	1.3304	0.4057	0.4470	0.104*
H7B	1.2512	0.4722	0.3753	0.104*
H7C	1.1753	0.3547	0.4147	0.104*
C8	1.2769 (2)	0.6114 (3)	0.52138 (12)	0.0565 (6)
H8A	1.3612	0.5516	0.5315	0.085*
H8B	1.2282	0.6061	0.5599	0.085*
H8C	1.3022	0.7127	0.5144	0.085*
C9	0.5495 (2)	0.7901 (2)	0.37649 (11)	0.0407 (4)
C10	0.4023 (2)	0.8091 (2)	0.33481 (10)	0.0368 (4)
C11	0.2962 (2)	0.8862 (2)	0.35927 (10)	0.0371 (4)
C12	0.1594 (2)	0.8939 (2)	0.32108 (10)	0.0413 (4)
H12	0.0898	0.9462	0.3380	0.050*
C13	0.1282 (2)	0.8222 (2)	0.25733 (11)	0.0421 (5)
C14	0.2292 (2)	0.7453 (3)	0.23114 (11)	0.0475 (5)
H14	0.2060	0.6973	0.1880	0.057*
C15	0.3667 (2)	0.7401 (3)	0.26988 (11)	0.0462 (5)
H15	0.4362	0.6895	0.2520	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.03958 (12)	0.04815 (13)	0.04116 (12)	−0.00333 (8)	0.00433 (8)	0.00070 (8)
Cl1	0.0350 (3)	0.1116 (6)	0.0562 (4)	−0.0014 (3)	−0.0082 (2)	−0.0039 (3)
Cl2	0.0598 (3)	0.0768 (4)	0.0421 (3)	0.0156 (3)	−0.0025 (2)	−0.0174 (3)
O1	0.0454 (9)	0.1017 (15)	0.0468 (9)	0.0178 (9)	0.0064 (7)	0.0247 (9)
N1	0.0289 (7)	0.0485 (10)	0.0377 (8)	0.0005 (7)	0.0004 (6)	0.0012 (7)
N2	0.0423 (9)	0.0558 (11)	0.0417 (9)	0.0141 (8)	0.0039 (7)	0.0030 (8)
C1	0.0314 (9)	0.0535 (13)	0.0429 (11)	0.0023 (8)	−0.0024 (8)	0.0071 (9)
C2	0.0401 (10)	0.0499 (12)	0.0418 (11)	−0.0048 (9)	0.0011 (9)	−0.0063 (9)
C3	0.0464 (11)	0.0446 (11)	0.0443 (11)	0.0036 (9)	0.0041 (9)	−0.0068 (9)
C4	0.0366 (10)	0.0424 (10)	0.0363 (10)	0.0024 (8)	0.0067 (8)	0.0066 (8)
C5	0.0348 (10)	0.0504 (12)	0.0339 (10)	0.0009 (8)	0.0000 (8)	−0.0024 (8)
C6	0.0379 (10)	0.0446 (11)	0.0397 (10)	0.0026 (8)	0.0034 (8)	−0.0050 (9)
C7	0.0671 (16)	0.0748 (18)	0.0635 (16)	0.0341 (14)	0.0072 (13)	−0.0041 (13)
C8	0.0436 (12)	0.0727 (16)	0.0477 (13)	0.0145 (11)	−0.0041 (10)	0.0073 (11)
C9	0.0355 (10)	0.0426 (10)	0.0415 (11)	0.0056 (8)	0.0019 (8)	0.0037 (9)
C10	0.0323 (9)	0.0384 (10)	0.0384 (10)	0.0020 (7)	0.0040 (8)	0.0033 (8)
C11	0.0371 (10)	0.0402 (10)	0.0328 (9)	0.0025 (8)	0.0039 (8)	0.0010 (8)
C12	0.0332 (9)	0.0494 (11)	0.0412 (11)	0.0060 (8)	0.0072 (8)	0.0028 (9)
C13	0.0298 (9)	0.0517 (12)	0.0420 (11)	−0.0035 (8)	0.0005 (8)	0.0044 (9)
C14	0.0422 (11)	0.0566 (14)	0.0414 (11)	−0.0048 (10)	0.0026 (9)	−0.0104 (10)
C15	0.0377 (10)	0.0539 (13)	0.0472 (12)	0.0057 (9)	0.0090 (9)	−0.0076 (10)

Geometric parameters (Å, º)

Br—Br	0.0000	C5—H5	0.9300
Cl1—C13	1.730 (2)	C6—H6	0.9300
Cl2—C11	1.736 (2)	C7—H7A	0.9600
O1—C9	1.204 (2)	C7—H7B	0.9600
N1—C2	1.347 (3)	C7—H7C	0.9600
N1—C6	1.356 (3)	C8—H8A	0.9600
N1—C1	1.466 (2)	C8—H8B	0.9600
N2—C4	1.340 (3)	C8—H8C	0.9600
N2—C7	1.456 (3)	C9—C10	1.495 (3)
N2—C8	1.458 (3)	C10—C15	1.387 (3)
C1—C9	1.517 (3)	C10—C11	1.393 (3)
C1—H1A	0.9700	C11—C12	1.379 (3)
C1—H1B	0.9700	C12—C13	1.376 (3)
C2—C3	1.348 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.371 (3)
C3—C4	1.422 (3)	C14—C15	1.386 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.411 (3)	C15—H15	0.9300
C5—C6	1.356 (3)
C2—N1—C6	119.07 (17)	N2—C7—H7C	109.5
C2—N1—C1	119.85 (17)	H7A—C7—H7C	109.5
C6—N1—C1	121.06 (17)	H7B—C7—H7C	109.5
C4—N2—C7	120.86 (19)	N2—C8—H8A	109.5
C4—N2—C8	122.25 (19)	N2—C8—H8B	109.5
C7—N2—C8	116.67 (18)	H8A—C8—H8B	109.5
N1—C1—C9	112.41 (17)	N2—C8—H8C	109.5
N1—C1—H1A	109.1	H8A—C8—H8C	109.5
C9—C1—H1A	109.1	H8B—C8—H8C	109.5
N1—C1—H1B	109.1	O1—C9—C10	122.32 (19)
C9—C1—H1B	109.1	O1—C9—C1	121.60 (18)
H1A—C1—H1B	107.9	C10—C9—C1	116.09 (17)
N1—C2—C3	122.10 (19)	C15—C10—C11	117.89 (17)
N1—C2—H2	119.0	C15—C10—C9	118.62 (18)
C3—C2—H2	119.0	C11—C10—C9	123.40 (18)
C2—C3—C4	120.6 (2)	C12—C11—C10	121.76 (18)
C2—C3—H3	119.7	C12—C11—Cl2	117.82 (15)
C4—C3—H3	119.7	C10—C11—Cl2	120.29 (15)
N2—C4—C5	122.87 (18)	C13—C12—C11	118.45 (19)
N2—C4—C3	121.39 (19)	C13—C12—H12	120.8
C5—C4—C3	115.74 (18)	C11—C12—H12	120.8
C6—C5—C4	120.68 (18)	C14—C13—C12	121.78 (18)
C6—C5—H5	119.7	C14—C13—Cl1	118.72 (16)
C4—C5—H5	119.7	C12—C13—Cl1	119.49 (16)
C5—C6—N1	121.69 (19)	C13—C14—C15	119.02 (19)
C5—C6—H6	119.2	C13—C14—H14	120.5
N1—C6—H6	119.2	C15—C14—H14	120.5
N2—C7—H7A	109.5	C14—C15—C10	121.09 (19)
N2—C7—H7B	109.5	C14—C15—H15	119.5
H7A—C7—H7B	109.5	C10—C15—H15	119.5
C2—N1—C1—C9	103.6 (2)	O1—C9—C10—C15	−127.5 (2)
C6—N1—C1—C9	−74.6 (2)	C1—C9—C10—C15	52.6 (3)
C6—N1—C2—C3	−2.4 (3)	O1—C9—C10—C11	49.0 (3)
C1—N1—C2—C3	179.4 (2)	C1—C9—C10—C11	−130.8 (2)
N1—C2—C3—C4	0.2 (3)	C15—C10—C11—C12	0.5 (3)
C7—N2—C4—C5	−175.7 (2)	C9—C10—C11—C12	−176.05 (19)
C8—N2—C4—C5	−1.3 (3)	C15—C10—C11—Cl2	−175.29 (16)
C7—N2—C4—C3	3.9 (3)	C9—C10—C11—Cl2	8.1 (3)
C8—N2—C4—C3	178.4 (2)	C10—C11—C12—C13	0.3 (3)
C2—C3—C4—N2	−177.0 (2)	Cl2—C11—C12—C13	176.23 (16)
C2—C3—C4—C5	2.6 (3)	C11—C12—C13—C14	−0.5 (3)
N2—C4—C5—C6	176.3 (2)	C11—C12—C13—Cl1	179.81 (16)
C3—C4—C5—C6	−3.3 (3)	C12—C13—C14—C15	−0.2 (3)
C4—C5—C6—N1	1.3 (3)	Cl1—C13—C14—C15	179.49 (18)
C2—N1—C6—C5	1.7 (3)	C13—C14—C15—C10	1.1 (3)
C1—N1—C6—C5	179.84 (19)	C11—C10—C15—C14	−1.2 (3)
N1—C1—C9—O1	21.6 (3)	C9—C10—C15—C14	175.5 (2)
N1—C1—C9—C10	−158.59 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Br	0.97	2.88	3.832 (2)	168
C15—H15···Br	0.93	2.84	3.687 (2)	151
C1—H1B···Br^i	0.97	2.78	3.620 (2)	145
C5—H5···Br^ii	0.93	2.87	3.753 (2)	158
C12—H12···Br^iii	0.93	2.80	3.691 (2)	160
C8—H8C···Cl2^iv	0.96	2.94	3.843 (3)	158

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) x+1, y, z.