Crystal structure of tetra­methyl­ammonium 1,1,7,7-tetra­cyano­hepta-2,4,6-trienide

In the crystal, C—H...N(nitrile) short contacts and stacking inter­actions combine to link the anions into layers parallel to the (01) plane and separated by columns of tetra­methyl­ammonium cations.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.067
• wR factor = 0.221
• Data-to-parameter ratio = 38.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          3 Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         N5 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -3.611 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          4 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C9       --C10      .        6.0 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C9       --C11      .        5.3 s.u.
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )        60% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         51 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Tetramethylammonium 1,1,7,7-tetracyanohepta-2,4,6-trienide

Crystal data

C4H12N^+·C11H5N4^−	F(000) = 568
Mr = 267.33	Dx = 1.136 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.6043 (5) Å	Cell parameters from 6241 reflections
b = 9.4168 (4) Å	θ = 2.6–25.6°
c = 16.4423 (7) Å	µ = 0.07 mm^−1
β = 107.8856 (17)°	T = 150 K
V = 1562.55 (12) Å^3	Block, light blue
Z = 4	0.35 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	3657 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.097
φ and ω scans	θmax = 35.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −17→17
Tmin = 0.654, Tmax = 0.747	k = −15→15
64536 measured reflections	l = −26→26
6914 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.221	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0941P)^2 + 0.374P] where P = (Fo^2 + 2Fc^2)/3
6914 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.50 e Å^−3
51 restraints	Δρmin = −0.51 e Å^−3

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	Occ. (<1)
N1	0.54341 (16)	0.24960 (18)	0.22446 (9)	0.0608 (4)
N2	0.36705 (18)	0.37537 (19)	−0.04834 (9)	0.0631 (4)
N3	−0.17214 (16)	0.90748 (17)	−0.16118 (8)	0.0548 (4)
N4	−0.29656 (17)	1.11815 (18)	0.04221 (10)	0.0617 (4)
C1	0.46618 (16)	0.31235 (16)	0.17174 (9)	0.0439 (3)
C2	0.37143 (14)	0.39111 (14)	0.10849 (8)	0.0375 (3)
C3	0.37173 (16)	0.37974 (16)	0.02231 (9)	0.0433 (3)
C4	0.28203 (14)	0.48084 (14)	0.12984 (8)	0.0360 (3)
H4	0.286927	0.486600	0.188411	0.043*
C5	0.18676 (15)	0.56214 (15)	0.07251 (8)	0.0391 (3)
H5	0.178726	0.553107	0.013587	0.047*
C6	0.10204 (14)	0.65596 (15)	0.09478 (8)	0.0374 (3)
H6	0.107502	0.663852	0.153364	0.045*
C7	0.00981 (15)	0.73879 (15)	0.03587 (8)	0.0385 (3)
H7	0.001958	0.726481	−0.022824	0.046*
C8	−0.07162 (13)	0.83809 (14)	0.05642 (8)	0.0356 (3)
H8	−0.068286	0.846208	0.114637	0.043*
C9	−0.15824 (14)	0.92700 (15)	−0.00276 (8)	0.0363 (3)
C10	−0.16767 (14)	0.91795 (16)	−0.09079 (9)	0.0400 (3)
C11	−0.23544 (16)	1.03238 (17)	0.02185 (9)	0.0432 (3)
N5	0.93087 (11)	0.33415 (12)	0.26390 (7)	0.0352 (2)
C12	0.90376 (19)	0.17881 (17)	0.25738 (11)	0.0514 (4)
H12A	0.924319	0.138185	0.314851	0.077*
H12B	0.810076	0.162583	0.226183	0.077*
H12C	0.959035	0.133384	0.226798	0.077*
C13	0.8536 (4)	0.4046 (3)	0.18099 (17)	0.0490 (7)*	0.663 (9)
H13A	0.871124	0.507013	0.184931	0.073*	0.663 (9)
H13B	0.881000	0.364754	0.133987	0.073*	0.663 (9)
H13C	0.758711	0.387889	0.170296	0.073*	0.663 (9)
C14	0.8909 (4)	0.4015 (3)	0.3353 (2)	0.0435 (7)*	0.663 (9)
H14A	0.910320	0.503380	0.337393	0.065*	0.663 (9)
H14B	0.795749	0.387336	0.325245	0.065*	0.663 (9)
H14C	0.940554	0.357500	0.389733	0.065*	0.663 (9)
C15	1.0755 (3)	0.3641 (3)	0.2819 (2)	0.0496 (8)*	0.663 (9)
H15A	1.090359	0.466948	0.285821	0.074*	0.663 (9)
H15B	1.125448	0.319406	0.336004	0.074*	0.663 (9)
H15C	1.105413	0.325613	0.235551	0.074*	0.663 (9)
C13A	1.0743 (7)	0.3428 (10)	0.3146 (7)	0.088 (3)*	0.337 (9)
H13D	1.088217	0.297754	0.370414	0.132*	0.337 (9)
H13E	1.127343	0.293692	0.283871	0.132*	0.337 (9)
H13F	1.101335	0.442639	0.322782	0.132*	0.337 (9)
C14A	0.9016 (9)	0.3989 (6)	0.1798 (3)	0.0563 (16)*	0.337 (9)
H14D	0.920339	0.500938	0.186074	0.084*	0.337 (9)
H14E	0.956852	0.355127	0.148616	0.084*	0.337 (9)
H14F	0.807893	0.384326	0.148001	0.084*	0.337 (9)
C15A	0.8467 (7)	0.3965 (5)	0.3131 (4)	0.0457 (14)*	0.337 (9)
H15D	0.868380	0.351102	0.369345	0.069*	0.337 (9)
H15E	0.863637	0.498739	0.320288	0.069*	0.337 (9)
H15F	0.753021	0.380433	0.281860	0.069*	0.337 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0710 (10)	0.0648 (10)	0.0455 (8)	0.0213 (8)	0.0162 (7)	0.0058 (7)
N2	0.0830 (11)	0.0716 (10)	0.0389 (7)	0.0087 (9)	0.0247 (7)	−0.0069 (7)
N3	0.0652 (9)	0.0656 (9)	0.0338 (6)	0.0110 (7)	0.0155 (6)	0.0044 (6)
N4	0.0747 (10)	0.0625 (10)	0.0571 (9)	0.0175 (8)	0.0339 (8)	0.0059 (7)
C1	0.0545 (9)	0.0407 (8)	0.0379 (7)	0.0050 (6)	0.0166 (6)	−0.0010 (6)
C2	0.0480 (7)	0.0346 (6)	0.0301 (6)	−0.0007 (5)	0.0121 (5)	−0.0019 (5)
C3	0.0543 (8)	0.0401 (7)	0.0368 (7)	0.0020 (6)	0.0160 (6)	−0.0050 (6)
C4	0.0469 (7)	0.0354 (6)	0.0264 (5)	−0.0043 (5)	0.0123 (5)	−0.0018 (5)
C5	0.0501 (8)	0.0398 (7)	0.0273 (6)	0.0012 (6)	0.0120 (5)	−0.0001 (5)
C6	0.0453 (7)	0.0372 (7)	0.0303 (6)	−0.0028 (5)	0.0125 (5)	0.0000 (5)
C7	0.0468 (7)	0.0407 (7)	0.0286 (6)	0.0004 (6)	0.0128 (5)	−0.0003 (5)
C8	0.0412 (7)	0.0390 (7)	0.0278 (6)	−0.0043 (5)	0.0125 (5)	0.0010 (5)
C9	0.0402 (7)	0.0416 (7)	0.0292 (6)	−0.0010 (5)	0.0138 (5)	0.0011 (5)
C10	0.0414 (7)	0.0454 (8)	0.0335 (6)	0.0037 (6)	0.0118 (5)	0.0038 (5)
C11	0.0491 (8)	0.0486 (8)	0.0353 (7)	0.0024 (6)	0.0179 (6)	0.0043 (6)
N5	0.0400 (6)	0.0364 (6)	0.0307 (5)	−0.0003 (4)	0.0133 (4)	0.0001 (4)
C12	0.0688 (11)	0.0371 (8)	0.0521 (9)	−0.0016 (7)	0.0243 (8)	0.0000 (6)

Geometric parameters (Å, º)

N1—C1	1.156 (2)	N5—C14A	1.455 (5)
N2—C3	1.1481 (19)	N5—C15A	1.496 (5)
N3—C10	1.1480 (18)	C12—H12A	0.9800
N4—C11	1.148 (2)	C12—H12B	0.9800
C1—C2	1.414 (2)	C12—H12C	0.9800
C2—C3	1.4220 (19)	C13—H13A	0.9800
C2—C4	1.3929 (19)	C13—H13B	0.9800
C4—H4	0.9500	C13—H13C	0.9800
C4—C5	1.382 (2)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C5—C6	1.387 (2)	C14—H14C	0.9800
C6—H6	0.9500	C15—H15A	0.9800
C6—C7	1.386 (2)	C15—H15B	0.9800
C7—H7	0.9500	C15—H15C	0.9800
C7—C8	1.3832 (19)	C13A—H13D	0.9800
C8—H8	0.9500	C13A—H13E	0.9800
C8—C9	1.3938 (19)	C13A—H13F	0.9800
C9—C10	1.4225 (18)	C14A—H14D	0.9800
C9—C11	1.422 (2)	C14A—H14E	0.9800
N5—C12	1.4883 (19)	C14A—H14F	0.9800
N5—C13	1.511 (3)	C15A—H15D	0.9800
N5—C14	1.505 (3)	C15A—H15E	0.9800
N5—C15	1.497 (3)	C15A—H15F	0.9800
N5—C13A	1.495 (7)
N1—C1—C2	178.84 (17)	H12A—C12—H12B	109.5
C1—C2—C3	118.35 (13)	H12A—C12—H12C	109.5
C4—C2—C1	121.18 (12)	H12B—C12—H12C	109.5
C4—C2—C3	120.45 (13)	N5—C13—H13A	109.5
N2—C3—C2	176.64 (18)	N5—C13—H13B	109.5
C2—C4—H4	117.4	N5—C13—H13C	109.5
C5—C4—C2	125.15 (12)	H13A—C13—H13B	109.5
C5—C4—H4	117.4	H13A—C13—H13C	109.5
C4—C5—H5	117.6	H13B—C13—H13C	109.5
C4—C5—C6	124.74 (12)	N5—C14—H14A	109.5
C6—C5—H5	117.6	N5—C14—H14B	109.5
C5—C6—H6	118.3	N5—C14—H14C	109.5
C7—C6—C5	123.32 (12)	H14A—C14—H14B	109.5
C7—C6—H6	118.3	H14A—C14—H14C	109.5
C6—C7—H7	117.7	H14B—C14—H14C	109.5
C8—C7—C6	124.69 (12)	N5—C15—H15A	109.5
C8—C7—H7	117.7	N5—C15—H15B	109.5
C7—C8—H8	117.9	N5—C15—H15C	109.5
C7—C8—C9	124.23 (12)	H15A—C15—H15B	109.5
C9—C8—H8	117.9	H15A—C15—H15C	109.5
C8—C9—C10	119.98 (12)	H15B—C15—H15C	109.5
C8—C9—C11	122.28 (12)	N5—C13A—H13D	109.5
C11—C9—C10	117.69 (13)	N5—C13A—H13E	109.5
N3—C10—C9	177.83 (16)	N5—C13A—H13F	109.5
N4—C11—C9	179.3 (2)	H13D—C13A—H13E	109.5
C12—N5—C13	109.12 (15)	H13D—C13A—H13F	109.5
C12—N5—C14	112.07 (14)	H13E—C13A—H13F	109.5
C12—N5—C15	111.28 (15)	N5—C14A—H14D	109.5
C12—N5—C13A	103.6 (4)	N5—C14A—H14E	109.5
C12—N5—C15A	106.9 (2)	N5—C14A—H14F	109.5
C14—N5—C13	108.31 (17)	H14D—C14A—H14E	109.5
C15—N5—C13	109.50 (18)	H14D—C14A—H14F	109.5
C15—N5—C14	106.48 (17)	H14E—C14A—H14F	109.5
C13A—N5—C15A	110.5 (4)	N5—C15A—H15D	109.5
C14A—N5—C12	111.3 (3)	N5—C15A—H15E	109.5
C14A—N5—C13A	113.0 (4)	N5—C15A—H15F	109.5
C14A—N5—C15A	111.2 (3)	H15D—C15A—H15E	109.5
N5—C12—H12A	109.5	H15D—C15A—H15F	109.5
N5—C12—H12B	109.5	H15E—C15A—H15F	109.5
N5—C12—H12C	109.5
C1—C2—C4—C5	179.67 (14)	C5—C6—C7—C8	−176.78 (14)
C2—C4—C5—C6	−176.99 (14)	C6—C7—C8—C9	175.87 (14)
C3—C2—C4—C5	1.4 (2)	C7—C8—C9—C10	0.6 (2)
C4—C5—C6—C7	178.25 (14)	C7—C8—C9—C11	−176.86 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N3^i	0.95	2.58	3.4819 (18)	159
C12—H12A···N2^ii	0.98	2.51	3.373 (2)	147

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