Tetra­methyl­ammonium hydrogen 4,5-dichloro­phthalate

In the title compound, C₄H₁₂⁺·C₈H₃Cl₂O₄⁻, the hydrogen 4,5-dichloro­phthalate ions are linked to the tetra­methyl­ammonium ions through C—H...O hydrogen bonds, generating two edge-fused motifs, viz. R₂¹(6) and S(7)R₁²(7). The cation and all atoms of the anion lie on a mirror plane.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.095
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.66 mm
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C7     ...       1.53 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C2     -   C8     ...       1.53 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O1      ..       3.21 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A   ..  O3      ..       2.82 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A   ..  O4      ..       2.75 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B    ..  O1      ..       2.76 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C4 H12 N

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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 (Farrugia, 1999).

Tetramethylammonium hydrogen 4,5-dichlorophthalate

Crystal data

C4H12N^+·C8H3Cl2O4^−	F(000) = 640
Mr = 308.15	Dx = 1.512 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 18405 reflections
a = 10.2800 (6) Å	θ = 2.1–27.6°
b = 6.9120 (3) Å	µ = 0.49 mm^−1
c = 19.0486 (10) Å	T = 296 K
V = 1353.51 (12) Å^3	Rod, colourless
Z = 4	0.66 × 0.35 × 0.17 mm

Data collection

Stoe IPDS-2 diffractometer	1449 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1239 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.065
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
Tmin = 0.783, Tmax = 0.931	l = −23→23
18362 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + 1 + 0.2573P + (0.0562P)^2] where P = 0.33Fo^2 + 0.67Fc^2
S = 1.03	(Δ/σ)max < 0.001
1449 reflections	Δρmax = 0.27 e Å^−3
116 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (4)

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	Occ. (<1)
C1	0.4066 (2)	0.2500	0.44167 (12)	0.0454 (5)
C2	0.4771 (2)	0.2500	0.50518 (11)	0.0450 (5)
C3	0.6127 (2)	0.2500	0.50158 (11)	0.0480 (5)
H3	0.6600	0.2500	0.5432	0.058*
C4	0.6796 (2)	0.2500	0.43883 (12)	0.0479 (5)
C5	0.6096 (2)	0.2500	0.37654 (11)	0.0472 (5)
C6	0.4759 (2)	0.2500	0.37902 (12)	0.0498 (5)
H6	0.4299	0.2500	0.3370	0.060*
C7	0.2594 (3)	0.2500	0.43061 (14)	0.0600 (6)
C8	0.4259 (3)	0.2500	0.58052 (13)	0.0542 (6)
C9	0.47041 (19)	−0.0750 (3)	0.20137 (11)	0.0650 (5)
H9A	0.3859	−0.0740	0.1799	0.097*
H9B	0.5176	0.0385	0.1874	0.097*
H9C	0.4611	−0.0764	0.2515	0.097*
C10	0.6754 (2)	−0.2500	0.21052 (15)	0.0675 (8)
H10A	0.6680	−0.2500	0.2608	0.101*
H10B	0.7218	−0.1366	0.1957	0.101*	0.50
H10C	0.7218	−0.3634	0.1957	0.101*	0.50
C11	0.5555 (3)	−0.2500	0.10057 (13)	0.0692 (8)
H11A	0.4706	−0.2500	0.0796	0.104*
H11B	0.6022	−0.3634	0.0860	0.104*	0.50
H11C	0.6022	−0.1366	0.0860	0.104*	0.50
N1	0.54249 (17)	−0.2500	0.17855 (10)	0.0487 (5)
O1	0.2171 (2)	0.2500	0.37122 (12)	0.0946 (8)
O2	0.1854 (2)	0.2500	0.48320 (13)	0.1022 (9)
O3	0.3031 (2)	0.2500	0.59080 (11)	0.0791 (6)
O4	0.5034 (2)	0.2500	0.62873 (9)	0.0729 (6)
Cl1	0.84719 (6)	0.2500	0.43804 (3)	0.0661 (3)
Cl2	0.68740 (6)	0.2500	0.29635 (3)	0.0611 (2)
H3A	0.242 (5)	0.2500	0.538 (3)	0.129 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0445 (12)	0.0447 (11)	0.0469 (12)	0.000	−0.0013 (9)	0.000
C2	0.0503 (12)	0.0434 (11)	0.0414 (11)	0.000	0.0022 (9)	0.000
C3	0.0484 (12)	0.0561 (13)	0.0394 (11)	0.000	−0.0044 (9)	0.000
C4	0.0455 (12)	0.0566 (13)	0.0416 (11)	0.000	−0.0020 (9)	0.000
C5	0.0491 (12)	0.0525 (13)	0.0399 (11)	0.000	−0.0002 (9)	0.000
C6	0.0501 (12)	0.0566 (14)	0.0425 (11)	0.000	−0.0045 (10)	0.000
C7	0.0470 (13)	0.0705 (17)	0.0626 (15)	0.000	0.0000 (12)	0.000
C8	0.0616 (15)	0.0556 (14)	0.0454 (12)	0.000	0.0078 (11)	0.000
C9	0.0577 (10)	0.0730 (12)	0.0643 (10)	0.0082 (9)	0.0015 (8)	−0.0009 (10)
C10	0.0385 (12)	0.101 (2)	0.0633 (16)	0.000	−0.0120 (11)	0.000
C11	0.0581 (15)	0.108 (2)	0.0413 (13)	0.000	−0.0002 (11)	0.000
N1	0.0348 (9)	0.0706 (13)	0.0406 (10)	0.000	−0.0011 (7)	0.000
O1	0.0528 (11)	0.168 (3)	0.0633 (13)	0.000	−0.0128 (10)	0.000
O2	0.0483 (11)	0.189 (3)	0.0694 (14)	0.000	0.0080 (10)	0.000
O3	0.0602 (11)	0.1206 (18)	0.0566 (12)	0.000	0.0159 (9)	0.000
O4	0.0784 (13)	0.0997 (15)	0.0405 (9)	0.000	0.0027 (9)	0.000
Cl1	0.0449 (3)	0.1033 (6)	0.0501 (4)	0.000	−0.0013 (2)	0.000
Cl2	0.0567 (4)	0.0860 (5)	0.0405 (3)	0.000	0.0038 (2)	0.000

Geometric parameters (Å, º)

C1—C6	1.390 (3)	C9—N1	1.483 (2)
C1—C2	1.410 (3)	C9—H9A	0.9600
C1—C7	1.528 (3)	C9—H9B	0.9600
C2—C3	1.396 (3)	C9—H9C	0.9600
C2—C8	1.529 (3)	C10—N1	1.496 (3)
C3—C4	1.379 (3)	C10—H10A	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.388 (3)	C10—H10C	0.9600
C4—Cl1	1.722 (2)	C11—N1	1.491 (3)
C5—C6	1.375 (3)	C11—H11A	0.9600
C5—Cl2	1.724 (2)	C11—H11B	0.9600
C6—H6	0.9300	C11—H11C	0.9600
C7—O1	1.212 (3)	N1—C9^i	1.483 (2)
C7—O2	1.258 (3)	O2—H3A	1.20 (5)
C8—O4	1.215 (3)	O3—H3A	1.18 (5)
C8—O3	1.278 (3)
C6—C1—C2	118.2 (2)	N1—C9—H9B	109.5
C6—C1—C7	112.9 (2)	H9A—C9—H9B	109.5
C2—C1—C7	128.9 (2)	N1—C9—H9C	109.5
C3—C2—C1	118.1 (2)	H9A—C9—H9C	109.5
C3—C2—C8	113.0 (2)	H9B—C9—H9C	109.5
C1—C2—C8	128.9 (2)	N1—C10—H10A	109.5
C4—C3—C2	122.7 (2)	N1—C10—H10B	109.5
C4—C3—H3	118.6	H10A—C10—H10B	109.5
C2—C3—H3	118.6	N1—C10—H10C	109.5
C3—C4—C5	118.8 (2)	H10A—C10—H10C	109.5
C3—C4—Cl1	120.41 (17)	H10B—C10—H10C	109.5
C5—C4—Cl1	120.75 (18)	N1—C11—H11A	109.5
C6—C5—C4	119.3 (2)	N1—C11—H11B	109.5
C6—C5—Cl2	119.61 (17)	H11A—C11—H11B	109.5
C4—C5—Cl2	121.11 (18)	N1—C11—H11C	109.5
C5—C6—C1	122.8 (2)	H11A—C11—H11C	109.5
C5—C6—H6	118.6	H11B—C11—H11C	109.5
C1—C6—H6	118.6	C9^i—N1—C9	109.2 (2)
O1—C7—O2	121.7 (3)	C9^i—N1—C11	109.68 (13)
O1—C7—C1	119.0 (2)	C9—N1—C11	109.68 (13)
O2—C7—C1	119.3 (2)	C9^i—N1—C10	109.69 (13)
O4—C8—O3	122.1 (2)	C9—N1—C10	109.69 (13)
O4—C8—C2	118.9 (2)	C11—N1—C10	108.86 (19)
O3—C8—C2	119.0 (2)	C7—O2—H3A	114 (2)
N1—C9—H9A	109.5	C8—O3—H3A	113 (2)
C6—C1—C2—C3	0.0	C4—C5—C6—C1	0.0
C7—C1—C2—C3	180.0	Cl2—C5—C6—C1	180.0
C6—C1—C2—C8	180.0	C2—C1—C6—C5	0.0
C7—C1—C2—C8	0.0	C7—C1—C6—C5	180.0
C1—C2—C3—C4	0.0	C6—C1—C7—O1	0.0
C8—C2—C3—C4	180.0	C2—C1—C7—O1	180.0
C2—C3—C4—C5	0.0	C6—C1—C7—O2	180.0
C2—C3—C4—Cl1	180.0	C2—C1—C7—O2	0.0
C3—C4—C5—C6	0.0	C3—C2—C8—O4	0.0
Cl1—C4—C5—C6	180.0	C1—C2—C8—O4	180.0
C3—C4—C5—Cl2	180.0	C3—C2—C8—O3	180.0
Cl1—C4—C5—Cl2	0.0	C1—C2—C8—O3	0.0

Symmetry code: (i) x, −y−1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H3A···O3	1.18 (5)	1.20 (5)	2.380 (3)	177 (4)
C11—H11A···O2^ii	0.96	2.44	3.337 (3)	156
C11—H11A···O3^ii	0.96	2.82	3.691 (3)	151
C10—H10A···O4^iii	0.96	2.75	3.571 (4)	145
C9—H9C···O4^iii	0.96	2.60	3.466 (3)	150
C9—H9B···O1^iv	0.96	2.76	3.659 (3)	157

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