Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In 3-methyl­anilinium picrate (3-MAP), C7H10N+·C6H2N3O7-, one of the nitro groups in the picrate ion is rotationally disordered with site occupancy factors of 0.80 and 0.20. The expected proton transfer took place between picric acid and 3-methyl­aniline, and the amine group is hydrogen bonded to two of the phenolate O atoms. The ortho-nitro groups deviate greatly from the benzene plane of the picrate ion, facilitating hydrogen-bond formation. While the cations are stacked as columns along the [001] direction, the anions are stacked in an offset fashion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009189/sg6000sup1.cif
Contains datablocks global, 3MAP

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009189/sg60003MAPsup2.hkl
Contains datablock 3MAP

CCDC reference: 270520

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.170
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found




Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 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 5 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 2 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 0 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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

3-methylanilinium picrate top
Crystal data top
C7H10N+·C6H2N3O7F(000) = 696
Mr = 336.27Dx = 1.483 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.439 (4) Åθ = 15–30°
b = 16.9472 (18) ŵ = 1.06 mm1
c = 7.4504 (8) ÅT = 293 K
β = 106.437 (18)°Needle, red
V = 1506.5 (5) Å30.50 × 0.30 × 0.30 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
2574 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 74.9°, θmin = 3.7°
ω–2θ scansh = 615
Absorption correction: ψ scan
(North et al., 1968)
k = 218
Tmin = 0.671, Tmax = 0.727l = 98
3596 measured reflections2 standard reflections every 100 reflections
3096 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.170 w = 1/[σ2(Fo2) + (0.0957P)2 + 0.4692P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3096 reflectionsΔρmax = 0.42 e Å3
261 parametersΔρmin = 0.34 e Å3
30 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0050 (7)
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
xyzUiso*/UeqOcc. (<1)
O10.84233 (11)0.18218 (8)0.1108 (2)0.0502 (4)
O20.77378 (16)0.04098 (10)0.0698 (2)0.0732 (5)
O30.79351 (18)0.04020 (11)0.1598 (3)0.0846 (6)
O41.19741 (15)0.07305 (10)0.4768 (2)0.0674 (5)
O51.30528 (14)0.02926 (12)0.5075 (3)0.0821 (6)
O61.1440 (2)0.28205 (15)0.2866 (7)0.1122 (13)0.80
O6'1.1256 (7)0.2811 (6)0.4363 (10)0.1122 (13)0.20
O70.97716 (19)0.30139 (14)0.3080 (4)0.0737 (8)0.80
O7'0.9770 (8)0.3009 (6)0.2141 (15)0.0737 (8)0.20
N10.82385 (15)0.01656 (10)0.0861 (3)0.0502 (4)
N21.21302 (16)0.00207 (12)0.4572 (3)0.0563 (5)
N31.05347 (11)0.25763 (11)0.2981 (3)0.0602 (5)
C10.92812 (15)0.14137 (11)0.1887 (2)0.0395 (4)
C20.92723 (15)0.05637 (11)0.1874 (3)0.0412 (4)
C31.01592 (17)0.00937 (12)0.2769 (3)0.0451 (4)
C41.11660 (16)0.04588 (12)0.3677 (3)0.0462 (5)
C51.12783 (16)0.12697 (12)0.3716 (3)0.0486 (5)
C61.03541 (16)0.17259 (11)0.2878 (3)0.0445 (4)
N40.73321 (14)0.30361 (10)0.2358 (3)0.0451 (4)
C70.61968 (15)0.27817 (12)0.2327 (3)0.0437 (4)
C80.5405 (2)0.33429 (18)0.2402 (3)0.0632 (6)
C90.4344 (2)0.3069 (3)0.2410 (4)0.0835 (10)
C100.4115 (2)0.2274 (2)0.2347 (4)0.0803 (9)
C110.49084 (19)0.17229 (18)0.2265 (3)0.0663 (7)
C120.59711 (16)0.19883 (13)0.2272 (3)0.0497 (5)
C130.4659 (3)0.0852 (2)0.2153 (5)0.1036 (12)
H13A0.38790.07700.15290.155*
H13B0.48340.06360.33930.155*
H13C0.51050.05950.14650.155*
H31.008 (2)0.0439 (15)0.271 (3)0.054 (6)*
H51.198 (2)0.1501 (16)0.436 (4)0.068 (7)*
H1N0.772 (2)0.2607 (17)0.199 (4)0.065 (7)*
H2N0.777 (2)0.3168 (16)0.353 (5)0.072 (8)*
H3N0.733 (2)0.3464 (18)0.164 (4)0.069 (8)*
H80.560 (2)0.3883 (17)0.256 (4)0.068 (8)*
H90.383 (3)0.346 (2)0.242 (5)0.106 (12)*
H100.330 (4)0.214 (2)0.225 (6)0.129 (14)*
H120.664 (2)0.1591 (15)0.216 (4)0.062 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0430 (7)0.0471 (7)0.0540 (8)0.0114 (6)0.0033 (6)0.0051 (6)
O20.0779 (12)0.0658 (10)0.0575 (10)0.0148 (8)0.0109 (8)0.0046 (8)
O30.0868 (13)0.0659 (11)0.0860 (13)0.0295 (10)0.0001 (10)0.0154 (9)
O40.0766 (11)0.0552 (9)0.0671 (10)0.0257 (8)0.0152 (8)0.0079 (8)
O50.0439 (9)0.0906 (14)0.1015 (15)0.0145 (9)0.0038 (9)0.0146 (11)
O60.0580 (14)0.0589 (13)0.230 (4)0.0144 (10)0.0585 (19)0.0002 (19)
O6'0.0580 (14)0.0589 (13)0.230 (4)0.0144 (10)0.0585 (19)0.0002 (19)
O70.0570 (11)0.0436 (9)0.123 (2)0.0017 (8)0.0296 (15)0.0158 (15)
O7'0.0570 (11)0.0436 (9)0.123 (2)0.0017 (8)0.0296 (15)0.0158 (15)
N10.0503 (9)0.0420 (9)0.0530 (10)0.0034 (7)0.0057 (7)0.0021 (7)
N20.0531 (11)0.0598 (11)0.0537 (10)0.0190 (8)0.0113 (8)0.0044 (8)
N30.0452 (10)0.0429 (9)0.0850 (14)0.0033 (7)0.0062 (9)0.0014 (9)
C10.0377 (9)0.0401 (9)0.0405 (9)0.0044 (7)0.0107 (7)0.0002 (7)
C20.0402 (9)0.0405 (9)0.0420 (9)0.0005 (7)0.0101 (7)0.0024 (7)
C30.0513 (11)0.0381 (10)0.0463 (10)0.0051 (8)0.0145 (8)0.0016 (7)
C40.0406 (10)0.0484 (10)0.0478 (10)0.0116 (8)0.0094 (8)0.0031 (8)
C50.0379 (10)0.0504 (11)0.0547 (11)0.0020 (8)0.0086 (8)0.0002 (9)
C60.0401 (9)0.0397 (10)0.0520 (11)0.0017 (7)0.0104 (8)0.0004 (8)
N40.0430 (9)0.0410 (8)0.0507 (9)0.0028 (7)0.0126 (7)0.0036 (7)
C70.0357 (9)0.0565 (11)0.0365 (9)0.0035 (7)0.0065 (7)0.0002 (7)
C80.0562 (13)0.0776 (17)0.0534 (12)0.0213 (12)0.0117 (10)0.0011 (11)
C90.0499 (14)0.139 (3)0.0598 (15)0.0358 (17)0.0134 (11)0.0048 (17)
C100.0387 (12)0.141 (3)0.0595 (15)0.0028 (15)0.0111 (10)0.0138 (16)
C110.0444 (12)0.0965 (19)0.0528 (12)0.0209 (11)0.0051 (9)0.0091 (12)
C120.0380 (9)0.0618 (12)0.0458 (10)0.0071 (8)0.0062 (8)0.0019 (9)
C130.080 (2)0.106 (3)0.112 (3)0.0488 (19)0.0073 (18)0.015 (2)
Geometric parameters (Å, º) top
O1—C11.266 (2)C5—H50.96 (3)
O2—N11.224 (2)N4—C71.471 (2)
O3—N11.219 (2)N4—H1N0.95 (3)
O4—N21.234 (3)N4—H2N0.92 (3)
O5—N21.223 (3)N4—H3N0.90 (3)
O6—N31.2259 (17)C7—C121.372 (3)
O6'—N31.2247 (19)C7—C81.381 (3)
O7—N31.2232 (17)C8—C91.402 (4)
O7'—N31.2243 (19)C8—H80.94 (3)
N1—C21.459 (2)C9—C101.375 (5)
N2—C41.446 (2)C9—H90.92 (4)
N3—C61.457 (3)C10—C111.373 (5)
C1—C61.431 (3)C10—H101.02 (4)
C1—C21.440 (3)C11—C121.395 (3)
C2—C31.371 (3)C11—C131.506 (4)
C3—C41.389 (3)C12—H121.09 (3)
C3—H30.91 (3)C13—H13A0.9600
C4—C51.381 (3)C13—H13B0.9600
C5—C61.380 (3)C13—H13C0.9600
O3—N1—O2123.69 (19)C1—C6—N3120.01 (16)
O3—N1—C2118.14 (18)C7—N4—H1N109.3 (16)
O2—N1—C2118.14 (17)C7—N4—H2N113.3 (18)
O5—N2—O4123.54 (19)H1N—N4—H2N104 (2)
O5—N2—C4118.8 (2)C7—N4—H3N112.6 (17)
O4—N2—C4117.69 (19)H1N—N4—H3N111 (2)
O7—N3—O6'98.5 (6)H2N—N4—H3N106 (2)
O7'—N3—O6'120.9 (8)C12—C7—C8122.3 (2)
O7—N3—O6122.9 (2)C12—C7—N4118.37 (17)
O7'—N3—O6111.0 (7)C8—C7—N4119.3 (2)
O7—N3—C6119.48 (18)C7—C8—C9117.1 (3)
O7'—N3—C6118.7 (6)C7—C8—H8121.0 (18)
O6'—N3—C6115.5 (5)C9—C8—H8121.6 (17)
O6—N3—C6117.46 (18)C10—C9—C8120.7 (3)
O1—C1—C6125.19 (17)C10—C9—H9124 (2)
O1—C1—C2122.63 (17)C8—C9—H9115 (2)
C6—C1—C2112.17 (15)C9—C10—C11121.6 (2)
C3—C2—C1125.03 (17)C9—C10—H10114 (2)
C3—C2—N1116.94 (17)C11—C10—H10124 (2)
C1—C2—N1118.02 (16)C10—C11—C12118.2 (3)
C2—C3—C4117.95 (18)C10—C11—C13122.0 (3)
C2—C3—H3119.4 (15)C12—C11—C13119.8 (3)
C4—C3—H3122.6 (15)C7—C12—C11120.1 (2)
C5—C4—C3121.70 (17)C7—C12—H12117.1 (14)
C5—C4—N2118.94 (18)C11—C12—H12122.7 (14)
C3—C4—N2119.36 (19)C11—C13—H13A109.5
C6—C5—C4118.81 (18)C11—C13—H13B109.5
C6—C5—H5121.6 (16)H13A—C13—H13B109.5
C4—C5—H5119.5 (17)C11—C13—H13C109.5
C5—C6—C1124.21 (18)H13A—C13—H13C109.5
C5—C6—N3115.73 (17)H13B—C13—H13C109.5
O1—C1—C2—C3176.65 (18)C2—C1—C6—C50.4 (3)
C6—C1—C2—C32.9 (3)O1—C1—C6—N32.7 (3)
O1—C1—C2—N12.2 (3)C2—C1—C6—N3177.77 (17)
C6—C1—C2—N1178.19 (16)O7—N3—C6—C5147.4 (3)
O3—N1—C2—C342.2 (3)O7'—N3—C6—C5174.5 (7)
O2—N1—C2—C3136.2 (2)O6'—N3—C6—C530.1 (6)
O3—N1—C2—C1136.8 (2)O6—N3—C6—C536.3 (4)
O2—N1—C2—C144.8 (3)O7—N3—C6—C135.1 (3)
C1—C2—C3—C43.7 (3)O7'—N3—C6—C13.1 (7)
N1—C2—C3—C4177.38 (17)O6'—N3—C6—C1152.4 (6)
C2—C3—C4—C51.1 (3)O6—N3—C6—C1141.2 (3)
C2—C3—C4—N2177.56 (18)C12—C7—C8—C90.3 (3)
O5—N2—C4—C511.4 (3)N4—C7—C8—C9178.6 (2)
O4—N2—C4—C5169.32 (19)C7—C8—C9—C100.0 (4)
O5—N2—C4—C3167.2 (2)C8—C9—C10—C110.3 (4)
O4—N2—C4—C312.0 (3)C9—C10—C11—C120.8 (4)
C3—C4—C5—C62.1 (3)C9—C10—C11—C13178.6 (3)
N2—C4—C5—C6179.32 (19)C8—C7—C12—C110.8 (3)
C4—C5—C6—C12.8 (3)N4—C7—C12—C11179.20 (19)
C4—C5—C6—N3179.74 (19)C10—C11—C12—C71.1 (3)
O1—C1—C6—C5179.98 (19)C13—C11—C12—C7178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H1N···O10.95 (3)1.82 (3)2.767 (2)175 (2)
N4—H2N···O1i0.92 (3)1.86 (3)2.750 (2)162 (3)
N4—H3N···O4ii0.90 (3)2.05 (3)2.898 (2)155 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+2, y+1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds