Ethyl­aminium picrate

Muthamizhchelvan, C.; Saminathan, K.; SethuSankar, K.; Fraanje, J.; Peschar, R.; Sivakumar, K.

doi:10.1107/S1600536805013644

Ethylaminium picrate

C. Muthamizhchelvan, K. Saminathan, K. SethuSankar, J. Fraanje, R. Peschar and K. Sivakumar

In the title salt, C₂H₈N⁺·C₆H₂N₃O₇⁻, there is complete transfer of the OH proton from picric acid to the amine. The picrate anions lie almost parallel to the monoclinic (101) plane and are connected by O

O short contacts. The ethylaminium and picrate ions are linked through N—H

O and C—H

O hydrogen bonds along the crystallographic b axis. In the picrate anion, tilting of the para-nitro group is a consequence of C—H

O hydrogen bonding between the ions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013644/sg6006sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013644/sg6006Isup2.hkl Contains datablock I

CCDC reference: 274623

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.079
wR factor = 0.226
Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.404     0.671
            Tmin' and Tmax expected:      0.451     0.669
            RR' =      0.892
            Please check that your absorption correction is appropriate.
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.680
            Test value =      0.600
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.68 e/A   3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8C    ..  O6      ..       2.68 Ang.

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Ethylaminium picrate top

Crystal data top

C₂H₈N⁺·C₆H₂N₃O₇⁻	F(000) = 568
M_r = 274.20	D_x = 1.615 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.616 (1) Å	θ = 25–45°
b = 8.663 (1) Å	µ = 1.26 mm⁻¹
c = 12.046 (1) Å	T = 293 K
β = 111.52 (1)°	Block, red
V = 1127.70 (19) Å³	0.58 × 0.38 × 0.32 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2006 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.063
Graphite monochromator	θ_max = 75.0°, θ_min = 4.5°
ω–2θ scans	h = −14→13
Absorption correction: ψ scan (North et al. 1968)	k = −10→4
T_min = 0.404, T_max = 0.671	l = −6→15
2646 measured reflections	2 standard reflections every 100 reflections
2325 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.079	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.226	w = 1/[σ²(F_o²) + (0.1181P)² + 1.0073P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2325 reflections	Δρ_max = 0.68 e Å⁻³
194 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (3)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.84337 (18)	0.4117 (2)	0.5369 (2)	0.0535 (6)
O2	0.8477 (2)	0.1269 (3)	0.4444 (2)	0.0646 (7)
O3	0.8365 (3)	−0.0447 (3)	0.5685 (3)	0.0723 (8)
O4	0.4755 (3)	0.0019 (3)	0.6724 (3)	0.0889 (10)
O5	0.4626 (2)	0.2159 (4)	0.7596 (3)	0.0753 (8)
O6	0.6176 (3)	0.6787 (3)	0.6456 (2)	0.0747 (8)
O7	0.6987 (3)	0.6645 (3)	0.5132 (3)	0.0826 (9)
N1	0.8118 (2)	0.0838 (3)	0.5226 (2)	0.0492 (6)
N2	0.5025 (2)	0.1373 (4)	0.6968 (2)	0.0593 (7)
N3	0.6655 (2)	0.6047 (3)	0.5888 (2)	0.0509 (6)
C1	0.7587 (2)	0.3517 (3)	0.5631 (2)	0.0431 (6)
C2	0.7388 (2)	0.1871 (3)	0.5641 (2)	0.0441 (6)
C3	0.6568 (3)	0.1175 (4)	0.6060 (3)	0.0481 (7)
C4	0.5870 (2)	0.2099 (4)	0.6498 (2)	0.0484 (7)
C5	0.5952 (3)	0.3691 (4)	0.6485 (3)	0.0484 (7)
C6	0.6732 (2)	0.4371 (3)	0.6013 (2)	0.0438 (6)
N4	0.9193 (2)	0.6892 (3)	0.4605 (2)	0.0508 (6)
C7	0.8437 (3)	0.7032 (5)	0.3328 (3)	0.0639 (9)
H7A	0.7596	0.7299	0.3234	0.077*
H7B	0.8417	0.6046	0.2940	0.077*
C8	0.8944 (4)	0.8245 (5)	0.2737 (3)	0.0663 (9)
H8A	0.9021	0.9205	0.3156	0.099*
H8B	0.8392	0.8375	0.1924	0.099*
H8C	0.9742	0.7928	0.2754	0.099*
H3	0.648 (3)	0.009 (5)	0.611 (3)	0.062 (10)*
H5	0.546 (4)	0.436 (4)	0.667 (3)	0.065 (10)*
H1N	0.887 (5)	0.599 (6)	0.488 (4)	0.096 (15)*
H2N	0.919 (3)	0.781 (4)	0.495 (3)	0.057 (9)*
H3N	0.996 (4)	0.672 (5)	0.484 (4)	0.066 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0427 (10)	0.0480 (11)	0.0754 (14)	0.0010 (8)	0.0284 (10)	0.0049 (9)
O2	0.0706 (15)	0.0639 (14)	0.0740 (15)	0.0014 (11)	0.0441 (13)	−0.0049 (11)
O3	0.0868 (18)	0.0455 (12)	0.0972 (19)	0.0107 (11)	0.0487 (16)	0.0030 (12)
O4	0.098 (2)	0.0706 (18)	0.122 (2)	−0.0198 (15)	0.068 (2)	0.0009 (16)
O5	0.0630 (15)	0.098 (2)	0.0788 (17)	−0.0023 (13)	0.0422 (14)	−0.0043 (14)
O6	0.0890 (18)	0.0630 (15)	0.0822 (17)	0.0186 (13)	0.0431 (15)	−0.0080 (12)
O7	0.0853 (18)	0.0546 (14)	0.137 (3)	0.0086 (12)	0.0750 (19)	0.0164 (15)
N1	0.0453 (12)	0.0442 (13)	0.0607 (14)	−0.0017 (9)	0.0226 (11)	−0.0055 (10)
N2	0.0478 (14)	0.0710 (18)	0.0626 (15)	−0.0022 (12)	0.0243 (12)	0.0058 (13)
N3	0.0368 (12)	0.0506 (14)	0.0640 (15)	0.0000 (9)	0.0169 (11)	−0.0062 (11)
C1	0.0327 (12)	0.0464 (14)	0.0462 (13)	0.0004 (10)	0.0096 (10)	0.0001 (11)
C2	0.0385 (12)	0.0451 (14)	0.0483 (13)	0.0025 (10)	0.0154 (11)	−0.0027 (11)
C3	0.0441 (14)	0.0473 (15)	0.0507 (15)	−0.0029 (11)	0.0147 (12)	0.0009 (12)
C4	0.0375 (13)	0.0584 (17)	0.0506 (15)	−0.0015 (11)	0.0178 (12)	0.0030 (12)
C5	0.0367 (13)	0.0573 (17)	0.0492 (14)	0.0021 (11)	0.0132 (11)	−0.0030 (12)
C6	0.0359 (12)	0.0449 (14)	0.0476 (13)	0.0006 (10)	0.0118 (10)	−0.0021 (11)
N4	0.0430 (13)	0.0456 (14)	0.0662 (16)	0.0027 (10)	0.0227 (12)	0.0023 (12)
C7	0.0480 (16)	0.078 (2)	0.0658 (19)	−0.0103 (15)	0.0216 (15)	−0.0103 (17)
C8	0.074 (2)	0.067 (2)	0.0571 (18)	0.0024 (17)	0.0234 (16)	0.0008 (15)

Geometric parameters (Å, º) top

O1—C1	1.251 (3)	C3—H3	0.95 (4)
O2—N1	1.221 (3)	C4—C5	1.383 (4)
O3—N1	1.229 (3)	C5—C6	1.368 (4)
O4—N2	1.222 (4)	C5—H5	0.90 (4)
O5—N2	1.228 (4)	N4—C7	1.470 (4)
O6—N3	1.212 (3)	N4—H1N	0.97 (5)
O7—N3	1.226 (4)	N4—H2N	0.90 (4)
N1—C2	1.442 (3)	N4—H3N	0.85 (5)
N2—C4	1.445 (4)	C7—C8	1.504 (5)
N3—C6	1.459 (4)	C7—H7A	0.9700
C1—C6	1.442 (4)	C7—H7B	0.9700
C1—C2	1.445 (4)	C8—H8A	0.9600
C2—C3	1.371 (4)	C8—H8B	0.9600
C3—C4	1.375 (4)	C8—H8C	0.9600

O2—N1—O3	122.3 (3)	C4—C5—H5	126 (2)
O2—N1—C2	119.3 (2)	C5—C6—C1	123.4 (3)
O3—N1—C2	118.4 (2)	C5—C6—N3	116.5 (2)
O4—N2—O5	124.0 (3)	C1—C6—N3	120.1 (2)
O4—N2—C4	118.4 (3)	C7—N4—H1N	105 (3)
O5—N2—C4	117.7 (3)	C7—N4—H2N	108 (2)
O6—N3—O7	122.0 (3)	H1N—N4—H2N	119 (4)
O6—N3—C6	119.5 (3)	C7—N4—H3N	121 (3)
O7—N3—C6	118.3 (2)	H1N—N4—H3N	103 (4)
O1—C1—C6	124.4 (3)	H2N—N4—H3N	101 (4)
O1—C1—C2	123.7 (2)	N4—C7—C8	111.4 (3)
C6—C1—C2	111.9 (2)	N4—C7—H7A	109.3
C3—C2—N1	115.5 (3)	C8—C7—H7A	109.3
C3—C2—C1	124.8 (3)	N4—C7—H7B	109.3
N1—C2—C1	119.6 (2)	C8—C7—H7B	109.3
C2—C3—C4	118.2 (3)	H7A—C7—H7B	108.0
C2—C3—H3	124 (2)	C7—C8—H8A	109.5
C4—C3—H3	117 (2)	C7—C8—H8B	109.5
C3—C4—C5	121.6 (3)	H8A—C8—H8B	109.5
C3—C4—N2	118.5 (3)	C7—C8—H8C	109.5
C5—C4—N2	119.9 (3)	H8A—C8—H8C	109.5
C6—C5—C4	119.5 (3)	H8B—C8—H8C	109.5
C6—C5—H5	114 (2)

O2—N1—C2—C3	151.0 (3)	O4—N2—C4—C5	163.2 (3)
O3—N1—C2—C3	−29.6 (4)	O5—N2—C4—C5	−17.1 (4)
O2—N1—C2—C1	−31.1 (4)	C3—C4—C5—C6	0.8 (4)
O3—N1—C2—C1	148.3 (3)	N2—C4—C5—C6	−178.5 (2)
O1—C1—C2—C3	171.7 (3)	C4—C5—C6—C1	−6.7 (4)
C6—C1—C2—C3	−5.5 (4)	C4—C5—C6—N3	172.4 (3)
O1—C1—C2—N1	−5.9 (4)	O1—C1—C6—C5	−168.6 (3)
C6—C1—C2—N1	176.8 (2)	C2—C1—C6—C5	8.6 (4)
N1—C2—C3—C4	178.3 (2)	O1—C1—C6—N3	12.3 (4)
C1—C2—C3—C4	0.5 (4)	C2—C1—C6—N3	−170.4 (2)
C2—C3—C4—C5	2.2 (4)	O6—N3—C6—C5	18.6 (4)
C2—C3—C4—N2	−178.5 (3)	O7—N3—C6—C5	−155.3 (3)
O4—N2—C4—C3	−16.1 (4)	O6—N3—C6—C1	−162.3 (3)
O5—N2—C4—C3	163.6 (3)	O7—N3—C6—C1	23.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N···O1	0.97 (5)	1.86 (5)	2.828 (3)	173 (4)
N4—H1N···O7	0.97 (5)	2.39 (5)	2.866 (4)	109 (3)
N4—H3N···O1ⁱ	0.85 (5)	2.10 (5)	2.881 (3)	153 (4)
N4—H3N···O2ⁱ	0.85 (5)	2.43 (4)	2.984 (4)	123 (3)
N4—H2N···O3ⁱⁱ	0.90 (4)	2.14 (4)	2.975 (4)	154 (3)
C7—H7A···O5ⁱⁱⁱ	0.97	2.45	3.389 (4)	164
C8—H8C···O6^iv	0.96	2.68	3.470 (5)	140

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

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Ethyl­aminium picrate

Supporting information

Key indicators

checkCIF/PLATON results

Ethylaminium picrate