Literature DB >> 21587877

(3-Pyrid-yl)methanaminium 4-nitro-phenolate 4-nitro-phenol solvate.

Abstract

In the crystal structure of the title compound, C(6)H(9)N(2) (+)·C(6)H(4)NO(3) (-)·C(6)H(5)NO(3), ions and mol-ecules are connected via inter-molecular N-H⋯O, N-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds into a three-dimensional network.

Entities: Chemical Disease Species

Year: 2010 PMID： 21587877 PMCID： PMC3006836 DOI： 10.1107/S1600536810021902

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to the development of ferroelectric pure organic or inorganic compounds, see: Haertling et al. (1999 ▶); Homes et al. (2001 ▶). For our recent reports on the synthesis of a variety of compounds which have potential piezoelectric and ferroelectric properties, see: Fu et al. (2009 ▶); Hang et al. (2009 ▶).

Experimental

Crystal data

C6H9N2 +·C6H4NO3 −·C6H5NO3 M = 386.36 Triclinic, a = 6.3666 (13) Å b = 7.4451 (15) Å c = 21.262 (4) Å α = 92.41 (3)° β = 95.56 (3)° γ = 113.99 (3)° V = 912.8 (3) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 293 K 0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.825, T max = 1.000 9547 measured reflections 4182 independent reflections 2896 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.140 S = 1.05 4182 reflections 253 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.25 e Å−3 Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021902/jh2162sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021902/jh2162Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₆H₉N₂⁺·C₆H₄NO₃⁻·C₆H₅nO₃	Z = 2
M_r = 386.36	F(000) = 404
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3666 (13) Å	Cell parameters from 4182 reflections
b = 7.4451 (15) Å	θ = 2.6–27.5°
c = 21.262 (4) Å	µ = 0.11 mm⁻¹
α = 92.41 (3)°	T = 293 K
β = 95.56 (3)°	Prism, colorless
γ = 113.99 (3)°	0.20 × 0.20 × 0.20 mm
V = 912.8 (3) Å³

Rigaku Mercury2 diffractometer	4182 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
graphite	R_int = 0.034
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD_Profile_fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
T_min = 0.825, T_max = 1.000	l = −27→27
9547 measured reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0576P)² + 0.2125P] where P = (F_o² + 2F_c²)/3
4182 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
O3	0.3538 (2)	0.0490 (2)	0.19323 (6)	0.0471 (3)
O4	0.7520 (2)	0.0641 (2)	0.23068 (6)	0.0490 (4)
H4A	0.6012	0.0634	0.2194	0.074*
C10	0.2665 (3)	0.2431 (3)	0.01944 (8)	0.0389 (4)
N3	0.2243 (3)	0.2980 (2)	−0.04283 (8)	0.0481 (4)
C7	0.3307 (3)	0.1152 (3)	0.13814 (8)	0.0369 (4)
O2	0.3528 (3)	0.2970 (2)	−0.08282 (7)	0.0609 (4)
O1	0.0584 (3)	0.3409 (3)	−0.05577 (7)	0.0687 (5)
C9	0.1125 (3)	0.2297 (3)	0.06264 (9)	0.0442 (5)
H9A	−0.0114	0.2633	0.0522	0.053*
C8	0.1442 (3)	0.1664 (3)	0.12100 (9)	0.0438 (4)
H10A	0.0403	0.1572	0.1499	0.053*
C13	0.8177 (3)	0.1128 (3)	0.29326 (8)	0.0388 (4)
C12	0.4868 (3)	0.1361 (3)	0.09345 (9)	0.0445 (5)
H12A	0.6144	0.1074	0.1040	0.053*
C11	0.4552 (3)	0.1978 (3)	0.03479 (9)	0.0445 (5)
H11A	0.5589	0.2091	0.0057	0.053*
C18	0.6884 (3)	0.1667 (3)	0.33310 (9)	0.0488 (5)
H18A	0.5513	0.1731	0.3165	0.059*
C16	0.9669 (4)	0.2016 (3)	0.42097 (9)	0.0523 (5)
C14	1.0262 (3)	0.1105 (3)	0.31834 (9)	0.0476 (5)
H14A	1.1167	0.0798	0.2917	0.057*
C15	1.0994 (4)	0.1534 (3)	0.38222 (10)	0.0530 (5)
H15A	1.2379	0.1497	0.3991	0.064*
C17	0.7627 (4)	0.2106 (3)	0.39719 (10)	0.0570 (6)
H17A	0.6761	0.2459	0.4240	0.068*
O5	1.2363 (4)	0.2523 (5)	0.50752 (9)	0.1289 (10)
O6	0.9263 (4)	0.2807 (4)	0.52407 (9)	0.1112 (8)
N4	1.0492 (5)	0.2488 (4)	0.48875 (10)	0.0792 (7)
N1	−0.0537 (3)	0.7260 (2)	0.20070 (7)	0.0414 (4)
H1A	−0.1686	0.7006	0.1696	0.062*
H1B	0.0690	0.8325	0.1935	0.062*
H1C	−0.0989	0.7476	0.2375	0.062*
N2	0.5902 (3)	0.6209 (3)	0.28249 (8)	0.0502 (4)
C1	0.5678 (4)	0.6498 (3)	0.34345 (9)	0.0485 (5)
H1D	0.6919	0.6693	0.3739	0.058*
C4	0.2013 (3)	0.5896 (3)	0.25514 (9)	0.0398 (4)
C5	0.4074 (3)	0.5913 (3)	0.24015 (9)	0.0466 (5)
H5A	0.4205	0.5703	0.1975	0.056*
C3	0.1849 (3)	0.6229 (3)	0.31859 (9)	0.0469 (5)
H3A	0.0499	0.6254	0.3309	0.056*
C6	0.0087 (4)	0.5549 (3)	0.20322 (10)	0.0491 (5)
H6A	0.0559	0.5305	0.1628	0.059*
H6C	−0.1262	0.4384	0.2101	0.059*
C2	0.3695 (3)	0.6522 (3)	0.36331 (9)	0.0490 (5)
H2A	0.3605	0.6733	0.4062	0.059*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0441 (8)	0.0624 (9)	0.0358 (7)	0.0228 (7)	0.0022 (6)	0.0128 (6)
O4	0.0430 (8)	0.0695 (9)	0.0332 (7)	0.0231 (7)	−0.0002 (6)	0.0017 (6)
C10	0.0433 (10)	0.0396 (10)	0.0295 (9)	0.0146 (8)	−0.0031 (7)	0.0008 (7)
N3	0.0561 (11)	0.0485 (10)	0.0345 (9)	0.0185 (8)	−0.0034 (8)	0.0026 (7)
C7	0.0358 (9)	0.0402 (10)	0.0305 (9)	0.0128 (8)	−0.0018 (7)	0.0015 (7)
O2	0.0672 (10)	0.0792 (11)	0.0352 (8)	0.0280 (8)	0.0083 (7)	0.0124 (7)
O1	0.0807 (12)	0.0936 (12)	0.0480 (9)	0.0546 (10)	−0.0054 (8)	0.0147 (8)
C9	0.0437 (11)	0.0536 (11)	0.0404 (10)	0.0265 (9)	−0.0004 (8)	0.0038 (9)
C8	0.0433 (11)	0.0561 (12)	0.0370 (10)	0.0249 (9)	0.0074 (8)	0.0044 (9)
C13	0.0389 (10)	0.0422 (10)	0.0324 (9)	0.0143 (8)	0.0020 (7)	0.0050 (8)
C12	0.0398 (10)	0.0605 (12)	0.0386 (10)	0.0267 (9)	0.0014 (8)	0.0068 (9)
C11	0.0412 (10)	0.0563 (12)	0.0360 (10)	0.0198 (9)	0.0059 (8)	0.0037 (8)
C18	0.0410 (11)	0.0651 (13)	0.0432 (11)	0.0253 (10)	0.0035 (8)	0.0031 (9)
C16	0.0573 (13)	0.0654 (13)	0.0322 (10)	0.0250 (11)	−0.0012 (9)	0.0009 (9)
C14	0.0441 (11)	0.0602 (12)	0.0420 (11)	0.0264 (10)	0.0024 (8)	−0.0029 (9)
C15	0.0458 (12)	0.0689 (14)	0.0451 (12)	0.0283 (11)	−0.0090 (9)	−0.0022 (10)
C17	0.0527 (13)	0.0778 (15)	0.0436 (12)	0.0291 (12)	0.0128 (9)	−0.0005 (11)
O5	0.1125 (19)	0.228 (3)	0.0508 (12)	0.088 (2)	−0.0332 (12)	−0.0189 (14)
O6	0.1272 (19)	0.172 (2)	0.0420 (10)	0.0706 (18)	0.0152 (11)	−0.0083 (12)
N4	0.0898 (17)	0.1082 (18)	0.0373 (11)	0.0416 (14)	−0.0021 (11)	−0.0018 (11)
N1	0.0396 (9)	0.0564 (10)	0.0309 (8)	0.0226 (8)	0.0024 (6)	0.0071 (7)
N2	0.0444 (10)	0.0676 (11)	0.0412 (9)	0.0260 (9)	0.0038 (7)	0.0050 (8)
C1	0.0471 (11)	0.0589 (12)	0.0383 (11)	0.0217 (10)	−0.0015 (8)	0.0085 (9)
C4	0.0421 (10)	0.0377 (10)	0.0379 (10)	0.0159 (8)	−0.0004 (8)	0.0047 (8)
C5	0.0499 (12)	0.0566 (12)	0.0343 (10)	0.0232 (10)	0.0043 (8)	0.0016 (9)
C3	0.0431 (11)	0.0576 (12)	0.0430 (11)	0.0232 (10)	0.0075 (8)	0.0076 (9)
C6	0.0529 (12)	0.0454 (11)	0.0462 (12)	0.0212 (10)	−0.0091 (9)	−0.0012 (9)
C2	0.0507 (12)	0.0643 (13)	0.0329 (10)	0.0235 (10)	0.0088 (8)	0.0081 (9)

O3—C7	1.308 (2)	C14—C15	1.373 (3)
O4—C13	1.344 (2)	C14—H14A	0.9300
O4—H4A	0.9646	C15—H15A	0.9300
C10—C9	1.385 (3)	C17—H17A	0.9300
C10—C11	1.387 (3)	O5—N4	1.209 (3)
C10—N3	1.435 (2)	O6—N4	1.218 (3)
N3—O1	1.232 (2)	N1—C6	1.482 (2)
N3—O2	1.238 (2)	N1—H1A	0.8900
C7—C8	1.409 (3)	N1—H1B	0.8900
C7—C12	1.409 (3)	N1—H1C	0.8900
C9—C8	1.371 (3)	N2—C1	1.336 (3)
C9—H9A	0.9300	N2—C5	1.336 (3)
C8—H10A	0.9300	C1—C2	1.376 (3)
C13—C14	1.389 (3)	C1—H1D	0.9300
C13—C18	1.389 (3)	C4—C5	1.375 (3)
C12—C11	1.372 (3)	C4—C3	1.383 (3)
C12—H12A	0.9300	C4—C6	1.498 (3)
C11—H11A	0.9300	C5—H5A	0.9300
C18—C17	1.378 (3)	C3—C2	1.375 (3)
C18—H18A	0.9300	C3—H3A	0.9300
C16—C15	1.370 (3)	C6—H6A	0.9700
C16—C17	1.377 (3)	C6—H6C	0.9700
C16—N4	1.462 (3)	C2—H2A	0.9300

C13—O4—H4A	110.0	C14—C15—H15A	120.3
C9—C10—C11	121.06 (17)	C16—C17—C18	119.14 (19)
C9—C10—N3	119.04 (17)	C16—C17—H17A	120.4
C11—C10—N3	119.86 (18)	C18—C17—H17A	120.4
O1—N3—O2	121.47 (17)	O5—N4—O6	122.7 (2)
O1—N3—C10	119.44 (17)	O5—N4—C16	118.4 (2)
O2—N3—C10	119.07 (17)	O6—N4—C16	119.0 (2)
O3—C7—C8	120.54 (17)	C6—N1—H1A	109.5
O3—C7—C12	122.14 (16)	C6—N1—H1B	109.5
C8—C7—C12	117.31 (16)	H1A—N1—H1B	109.5
C8—C9—C10	119.43 (17)	C6—N1—H1C	109.5
C8—C9—H9A	120.3	H1A—N1—H1C	109.5
C10—C9—H9A	120.3	H1B—N1—H1C	109.5
C9—C8—C7	121.42 (18)	C1—N2—C5	116.81 (18)
C9—C8—H10A	119.3	N2—C1—C2	123.07 (19)
C7—C8—H10A	119.3	N2—C1—H1D	118.5
O4—C13—C14	117.63 (17)	C2—C1—H1D	118.5
O4—C13—C18	123.06 (17)	C5—C4—C3	117.13 (18)
C14—C13—C18	119.31 (17)	C5—C4—C6	119.56 (18)
C11—C12—C7	121.54 (17)	C3—C4—C6	123.31 (18)
C11—C12—H12A	119.2	N2—C5—C4	124.60 (18)
C7—C12—H12A	119.2	N2—C5—H5A	117.7
C12—C11—C10	119.20 (18)	C4—C5—H5A	117.7
C12—C11—H11A	120.4	C2—C3—C4	119.60 (19)
C10—C11—H11A	120.4	C2—C3—H3A	120.2
C17—C18—C13	120.22 (19)	C4—C3—H3A	120.2
C17—C18—H18A	119.9	N1—C6—C4	111.67 (16)
C13—C18—H18A	119.9	N1—C6—H6A	109.3
C15—C16—C17	121.48 (19)	C4—C6—H6A	109.3
C15—C16—N4	118.6 (2)	N1—C6—H6C	109.3
C17—C16—N4	119.9 (2)	C4—C6—H6C	109.3
C15—C14—C13	120.36 (19)	H6A—C6—H6C	107.9
C15—C14—H14A	119.8	C3—C2—C1	118.79 (19)
C13—C14—H14A	119.8	C3—C2—H2A	120.6
C16—C15—C14	119.43 (19)	C1—C2—H2A	120.6
C16—C15—H15A	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.89	2.09	2.952 (2)	162
N1—H1B···O3ⁱⁱ	0.89	1.87	2.753 (2)	169
N1—H1C···N2ⁱⁱⁱ	0.89	2.16	2.866 (2)	136
O4—H4A···O3	0.96	1.58	2.5385 (19)	173
C1—H1D···O5^iv	0.93	2.52	3.229 (3)	133
C2—H2A···O6^v	0.93	2.58	3.327 (3)	138
C8—H10A···O4ⁱⁱⁱ	0.93	2.54	3.462 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.89	2.09	2.952 (2)	162
N1—H1B⋯O3ⁱⁱ	0.89	1.87	2.753 (2)	169
N1—H1C⋯N2ⁱⁱⁱ	0.89	2.16	2.866 (2)	136
O4—H4A⋯O3	0.96	1.58	2.5385 (19)	173
C1—H1D⋯O5^iv	0.93	2.52	3.229 (3)	133
C2—H2A⋯O6^v	0.93	2.58	3.327 (3)	138
C8—H10A⋯O4ⁱⁱⁱ	0.93	2.54	3.462 (3)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

2 in total

1. Optical response of high-dielectric-constant perovskite-related oxide.

Authors: C C Homes; T Vogt; S M Shapiro; S Wakimoto; A P Ramirez
Journal: Science Date: 2001-07-27 Impact factor: 47.728

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2 in total