Diisopropyl­ethyl­ammonium picrate

The structure of the title compound, C₈H₂₀N^+.C₆H₂N₃O₇^-, consists of discrete diisopropyl­ethyl­ammonium cations and picrate anions. The protonated N atom of the cation forms a hydrogen bond to the phenol O atom of the picrate anion.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.048
• wR factor = 0.121
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.

   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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 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, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

Diisopropylethylammonium picrate

Crystal data

C8H20N^+·C6H2N3O7^−	F(000) = 760
Mr = 358.36	Dx = 1.369 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5036 reflections
a = 7.3769 (10) Å	θ = 3.5–25.6°
b = 11.3828 (13) Å	µ = 0.11 mm^−1
c = 20.715 (3) Å	T = 173 K
β = 91.173 (11)°	Rod, yellow
V = 1739.1 (4) Å^3	0.21 × 0.12 × 0.12 mm
Z = 4

Data collection

Stoe IPDS-II two-circle diffractometer	2188 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Graphite monochromator	θmax = 25.6°, θmin = 3.5°
ω scans	h = −8→8
7320 measured reflections	k = −13→12
3182 independent reflections	l = −20→25

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0655P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
3182 reflections	Δρmax = 0.23 e Å^−3
240 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: 0.013 (2)

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)
O1	0.1273 (2)	0.69647 (13)	0.58508 (8)	0.0298 (4)
C1	0.1751 (2)	0.61258 (17)	0.55087 (10)	0.0206 (4)
C2	0.1887 (3)	0.61498 (17)	0.48098 (10)	0.0217 (4)
C3	0.2541 (3)	0.52365 (18)	0.44404 (11)	0.0253 (5)
H3	0.2610	0.5315	0.3985	0.030*
C4	0.3095 (2)	0.42070 (17)	0.47410 (11)	0.0244 (5)
C5	0.3043 (2)	0.40846 (17)	0.54082 (11)	0.0247 (5)
H5	0.3470	0.3387	0.5612	0.030*
C6	0.2362 (2)	0.49912 (17)	0.57671 (10)	0.0228 (5)
N2	0.1356 (3)	0.72163 (16)	0.44620 (10)	0.0347 (5)
N4	0.3788 (2)	0.32417 (17)	0.43587 (11)	0.0359 (5)
N6	0.2291 (3)	0.48127 (17)	0.64632 (10)	0.0340 (5)
O21	0.2211 (5)	0.7461 (2)	0.39664 (12)	0.0738 (14)	0.880 (8)
O22	0.0159 (4)	0.7831 (2)	0.46710 (13)	0.0438 (7)	0.880 (8)
O21'	0.080 (3)	0.7149 (15)	0.3903 (9)	0.050 (6)*	0.120 (8)
O22'	0.086 (3)	0.8103 (18)	0.4770 (10)	0.043 (6)*	0.120 (8)
O41	0.4372 (2)	0.23618 (15)	0.46467 (11)	0.0485 (5)
O42	0.3782 (3)	0.33486 (17)	0.37682 (10)	0.0511 (5)
O61	0.0946 (3)	0.51625 (17)	0.67440 (9)	0.0522 (5)
O62	0.3568 (3)	0.4301 (2)	0.67330 (10)	0.0626 (6)
N10	0.1512 (2)	0.90487 (15)	0.65963 (9)	0.0201 (4)
H10	0.131 (3)	0.847 (2)	0.6353 (12)	0.020 (6)*
C16	0.3298 (3)	0.95957 (19)	0.63744 (11)	0.0276 (5)
H16	0.4252	0.8974	0.6407	0.033*
C11	−0.0084 (3)	0.98936 (18)	0.65183 (11)	0.0253 (5)
H11A	−0.0624	1.0035	0.6945	0.030*
H11B	0.0356	1.0655	0.6352	0.030*
C15	0.3283 (4)	0.7743 (2)	0.73695 (13)	0.0432 (6)
H15A	0.4374	0.8216	0.7303	0.065*
H15B	0.3244	0.7097	0.7056	0.065*
H15C	0.3311	0.7421	0.7808	0.065*
C13	0.1596 (3)	0.8516 (2)	0.72758 (11)	0.0302 (5)
H13	0.1652	0.9170	0.7598	0.036*
C18	0.3890 (3)	1.0606 (2)	0.68152 (14)	0.0445 (7)
H18A	0.3975	1.0327	0.7262	0.067*
H18B	0.2998	1.1243	0.6783	0.067*
H18C	0.5076	1.0897	0.6683	0.067*
C14	−0.0137 (4)	0.7808 (2)	0.73811 (14)	0.0409 (6)
H14A	−0.1195	0.8319	0.7320	0.061*
H14B	−0.0122	0.7490	0.7821	0.061*
H14C	−0.0202	0.7159	0.7070	0.061*
C12	−0.1519 (3)	0.9409 (2)	0.60593 (14)	0.0413 (6)
H12A	−0.2524	0.9970	0.6020	0.062*
H12B	−0.1970	0.8661	0.6226	0.062*
H12C	−0.0994	0.9283	0.5634	0.062*
C17	0.3119 (3)	0.9947 (2)	0.56713 (12)	0.0340 (5)
H17A	0.2735	0.9265	0.5414	0.051*
H17B	0.4291	1.0230	0.5521	0.051*
H17C	0.2213	1.0573	0.5624	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0391 (8)	0.0205 (8)	0.0301 (9)	0.0020 (6)	0.0053 (7)	−0.0082 (7)
C1	0.0188 (9)	0.0169 (9)	0.0261 (11)	−0.0026 (7)	0.0004 (8)	−0.0037 (8)
C2	0.0240 (9)	0.0173 (10)	0.0236 (11)	−0.0010 (7)	−0.0035 (8)	0.0000 (8)
C3	0.0241 (9)	0.0287 (11)	0.0232 (11)	−0.0054 (8)	0.0015 (8)	−0.0074 (9)
C4	0.0178 (9)	0.0184 (10)	0.0370 (13)	−0.0009 (7)	0.0014 (8)	−0.0095 (9)
C5	0.0174 (9)	0.0176 (9)	0.0390 (13)	−0.0006 (7)	0.0002 (8)	0.0006 (9)
C6	0.0208 (9)	0.0210 (10)	0.0265 (12)	−0.0039 (7)	0.0010 (8)	0.0009 (9)
N2	0.0526 (12)	0.0238 (10)	0.0274 (11)	0.0032 (9)	−0.0076 (9)	0.0029 (8)
N4	0.0265 (9)	0.0293 (11)	0.0520 (15)	−0.0028 (8)	0.0062 (9)	−0.0193 (10)
N6	0.0460 (11)	0.0296 (10)	0.0265 (11)	−0.0052 (9)	0.0027 (9)	0.0066 (9)
O21	0.128 (3)	0.0559 (16)	0.0386 (15)	0.0291 (17)	0.0339 (15)	0.0242 (13)
O22	0.0381 (15)	0.0335 (13)	0.0597 (16)	0.0144 (11)	0.0017 (12)	0.0112 (11)
O41	0.0397 (9)	0.0267 (9)	0.0789 (15)	0.0097 (7)	0.0005 (9)	−0.0176 (9)
O42	0.0574 (11)	0.0490 (11)	0.0479 (13)	−0.0055 (9)	0.0201 (9)	−0.0258 (10)
O61	0.0770 (13)	0.0426 (11)	0.0381 (11)	0.0087 (9)	0.0293 (9)	0.0088 (9)
O62	0.0608 (12)	0.0833 (16)	0.0431 (12)	0.0078 (11)	−0.0117 (10)	0.0290 (12)
N10	0.0218 (8)	0.0189 (9)	0.0196 (9)	0.0005 (6)	0.0002 (7)	−0.0035 (8)
C16	0.0214 (9)	0.0295 (11)	0.0321 (12)	−0.0001 (8)	0.0043 (8)	−0.0034 (10)
C11	0.0236 (10)	0.0224 (10)	0.0299 (12)	0.0053 (8)	0.0031 (8)	−0.0017 (9)
C15	0.0552 (15)	0.0437 (15)	0.0303 (14)	0.0144 (12)	−0.0071 (11)	0.0083 (12)
C13	0.0431 (12)	0.0291 (12)	0.0185 (11)	0.0054 (9)	0.0022 (9)	−0.0013 (9)
C18	0.0336 (12)	0.0457 (15)	0.0540 (17)	−0.0124 (11)	−0.0038 (11)	−0.0112 (13)
C14	0.0565 (15)	0.0280 (12)	0.0388 (15)	0.0039 (11)	0.0182 (12)	0.0059 (11)
C12	0.0276 (11)	0.0436 (14)	0.0521 (17)	0.0061 (10)	−0.0078 (11)	−0.0058 (12)
C17	0.0298 (11)	0.0357 (13)	0.0368 (14)	0.0011 (9)	0.0096 (9)	0.0036 (11)

Geometric parameters (Å, º)

O1—C1	1.244 (2)	C16—C17	1.513 (3)
C1—C2	1.453 (3)	C16—C18	1.527 (3)
C1—C6	1.466 (3)	C16—H16	1.0000
C2—C3	1.384 (3)	C11—C12	1.513 (3)
C2—N2	1.461 (3)	C11—H11A	0.9900
C3—C4	1.385 (3)	C11—H11B	0.9900
C3—H3	0.9500	C15—C13	1.534 (3)
C4—C5	1.390 (3)	C15—H15A	0.9800
C4—N4	1.453 (3)	C15—H15B	0.9800
C5—C6	1.373 (3)	C15—H15C	0.9800
C5—H5	0.9500	C13—C14	1.531 (4)
C6—N6	1.458 (3)	C13—H13	1.0000
N2—O22	1.213 (3)	C18—H18A	0.9800
N2—O21'	1.222 (17)	C18—H18B	0.9800
N2—O21	1.247 (3)	C18—H18C	0.9800
N2—O22'	1.25 (2)	C14—H14A	0.9800
N4—O42	1.229 (3)	C14—H14B	0.9800
N4—O41	1.239 (3)	C14—H14C	0.9800
N6—O61	1.227 (3)	C12—H12A	0.9800
N6—O62	1.232 (3)	C12—H12B	0.9800
N10—C11	1.526 (2)	C12—H12C	0.9800
N10—C13	1.533 (3)	C17—H17A	0.9800
N10—C16	1.536 (3)	C17—H17B	0.9800
N10—H10	0.84 (2)	C17—H17C	0.9800
O1—C1—C2	125.37 (18)	C12—C11—N10	111.43 (17)
O1—C1—C6	123.84 (19)	C12—C11—H11A	109.3
C2—C1—C6	110.69 (17)	N10—C11—H11A	109.3
C3—C2—C1	124.66 (18)	C12—C11—H11B	109.3
C3—C2—N2	116.40 (19)	N10—C11—H11B	109.3
C1—C2—N2	118.91 (18)	H11A—C11—H11B	108.0
C2—C3—C4	119.35 (19)	C13—C15—H15A	109.5
C2—C3—H3	120.3	C13—C15—H15B	109.5
C4—C3—H3	120.3	H15A—C15—H15B	109.5
C3—C4—C5	121.19 (19)	C13—C15—H15C	109.5
C3—C4—N4	119.9 (2)	H15A—C15—H15C	109.5
C5—C4—N4	118.87 (19)	H15B—C15—H15C	109.5
C6—C5—C4	118.73 (19)	C14—C13—N10	108.73 (18)
C6—C5—H5	120.6	C14—C13—C15	110.9 (2)
C4—C5—H5	120.6	N10—C13—C15	111.13 (19)
C5—C6—N6	116.85 (19)	C14—C13—H13	108.7
C5—C6—C1	125.3 (2)	N10—C13—H13	108.7
N6—C6—C1	117.84 (18)	C15—C13—H13	108.7
O22—N2—O21	123.3 (2)	C16—C18—H18A	109.5
O21'—N2—O22'	116.1 (12)	C16—C18—H18B	109.5
O22—N2—C2	119.6 (2)	H18A—C18—H18B	109.5
O21'—N2—C2	119.7 (8)	C16—C18—H18C	109.5
O21—N2—C2	117.1 (2)	H18A—C18—H18C	109.5
O22'—N2—C2	119.7 (9)	H18B—C18—H18C	109.5
O42—N4—O41	123.6 (2)	C13—C14—H14A	109.5
O42—N4—C4	118.2 (2)	C13—C14—H14B	109.5
O41—N4—C4	118.1 (2)	H14A—C14—H14B	109.5
O61—N6—O62	123.8 (2)	C13—C14—H14C	109.5
O61—N6—C6	118.01 (19)	H14A—C14—H14C	109.5
O62—N6—C6	118.2 (2)	H14B—C14—H14C	109.5
C11—N10—C13	111.28 (16)	C11—C12—H12A	109.5
C11—N10—C16	112.16 (16)	C11—C12—H12B	109.5
C13—N10—C16	114.62 (15)	H12A—C12—H12B	109.5
C11—N10—H10	107.7 (14)	C11—C12—H12C	109.5
C13—N10—H10	104.0 (16)	H12A—C12—H12C	109.5
C16—N10—H10	106.4 (16)	H12B—C12—H12C	109.5
C17—C16—C18	113.3 (2)	C16—C17—H17A	109.5
C17—C16—N10	109.68 (16)	C16—C17—H17B	109.5
C18—C16—N10	111.28 (19)	H17A—C17—H17B	109.5
C17—C16—H16	107.4	C16—C17—H17C	109.5
C18—C16—H16	107.4	H17A—C17—H17C	109.5
N10—C16—H16	107.4	H17B—C17—H17C	109.5
O1—C1—C2—C3	175.25 (19)	C1—C2—N2—O21	146.5 (3)
C6—C1—C2—C3	−1.3 (3)	C3—C2—N2—O22'	−175.4 (13)
O1—C1—C2—N2	−2.8 (3)	C1—C2—N2—O22'	2.8 (13)
C6—C1—C2—N2	−179.37 (17)	C3—C4—N4—O42	−3.5 (3)
C1—C2—C3—C4	0.9 (3)	C5—C4—N4—O42	178.09 (19)
N2—C2—C3—C4	179.04 (17)	C3—C4—N4—O41	175.74 (18)
C2—C3—C4—C5	−1.5 (3)	C5—C4—N4—O41	−2.7 (3)
C2—C3—C4—N4	−179.87 (17)	C5—C6—N6—O61	−139.3 (2)
C3—C4—C5—C6	2.5 (3)	C1—C6—N6—O61	42.3 (3)
N4—C4—C5—C6	−179.05 (17)	C5—C6—N6—O62	39.4 (3)
C4—C5—C6—N6	178.47 (17)	C1—C6—N6—O62	−139.0 (2)
C4—C5—C6—C1	−3.2 (3)	C11—N10—C16—C17	−59.1 (2)
O1—C1—C6—C5	−174.15 (19)	C13—N10—C16—C17	172.70 (17)
C2—C1—C6—C5	2.5 (2)	C11—N10—C16—C18	67.0 (2)
O1—C1—C6—N6	4.2 (3)	C13—N10—C16—C18	−61.2 (2)
C2—C1—C6—N6	−179.19 (16)	C13—N10—C11—C12	−111.3 (2)
C3—C2—N2—O22	150.2 (3)	C16—N10—C11—C12	118.8 (2)
C1—C2—N2—O22	−31.6 (3)	C11—N10—C13—C14	62.0 (2)
C3—C2—N2—O21'	29.2 (12)	C16—N10—C13—C14	−169.37 (18)
C1—C2—N2—O21'	−152.5 (11)	C11—N10—C13—C15	−175.58 (18)
C3—C2—N2—O21	−31.7 (3)	C16—N10—C13—C15	−47.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O1	0.84 (2)	2.00 (3)	2.834 (2)	169 (2)