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The 1:1 adduct of 4-amino­benzoic acid (PABA) with 4-am-inobenzonitrile (PABN), C7H7NO2·C7H6N2, consists of a primary centrosymmetric cyclic hydrogen-bonded PABA dimer interaction [O...O 2.640 (3) Å] peripherally linked into chains by weaker hydrogen bonds via a head-to-tail PABN interaction [N...N 3.179 (4) and N...O 3.062 (4) Å], and is linked between the chains by amine-N (PABN) to amine-N (PABA) interactions [N...N 3.233 (5) Å]. No proton transfer occurs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000874X/ta1290sup1.cif
Contains datablocks I, global

sft

Structure factor file (SHELXL table format) https://doi.org/10.1107/S010827010000874X/ta1290Isup2.sft
Supplementary material

CCDC reference: 150860

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR88 (Burla et al., 1989); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C7H7NO2·C7H6N2Dx = 1.260 Mg m3
Mr = 255.28Melting point = 479–481 K
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
a = 4.860 (3) ÅCell parameters from 25 reflections
b = 32.543 (4) Åθ = 10–20°
c = 8.538 (3) ŵ = 0.09 mm1
β = 94.79 (4)°T = 153 K
V = 1345.6 (8) Å3Prismatic, colourless
Z = 40.3 × 0.2 × 0.2 mm
F(000) = 536.00
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.074
Radiation source: 12kW rotating anode X-ray tubeθmax = 25°
Graphite monochromatorh = 05
ω scans with profile analysisk = 038
2723 measured reflectionsl = 1010
2372 independent reflections3 standard reflections every 150 min
1614 reflections with I > 1.5σ(I) intensity decay: 0.0%
Refinement top
Refinement on FH atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: fullWeighting scheme based on measured s.u.'s
R[F2 > 2σ(F2)] = 0.045(Δ/σ)max = 0.002
wR(F2) = 0.043Δρmax = 0.14 e Å3
S = 1.80Δρmin = 0.16 e Å3
1614 reflectionsExtinction correction: Zachariasen_type_2_Gaussian_isotropic
193 parametersExtinction coefficient: 8.001
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3550 (3)0.04485 (4)0.0193 (2)0.0517 (4)
O20.2661 (3)0.01288 (4)0.1487 (2)0.0544 (5)
N10.4703 (4)0.11097 (6)0.5062 (2)0.0595 (7)
N20.0888 (5)0.10283 (7)0.2321 (3)0.0646 (7)
N30.5519 (6)0.29556 (6)0.1002 (3)0.133 (1)
C10.0395 (4)0.04765 (5)0.2181 (2)0.0411 (5)
C20.0082 (4)0.09006 (5)0.2065 (2)0.0502 (6)
C30.1637 (4)0.11087 (5)0.2983 (2)0.0523 (7)
C40.3106 (4)0.08980 (6)0.4072 (2)0.0467 (6)
C50.2797 (4)0.04707 (6)0.4189 (2)0.0503 (6)
C60.1088 (4)0.02650 (5)0.3247 (2)0.0476 (6)
C70.2318 (4)0.02670 (6)0.1203 (2)0.0435 (6)
C110.3737 (5)0.22182 (7)0.1439 (3)0.0695 (8)
C120.1585 (5)0.21454 (7)0.2567 (3)0.0709 (8)
C130.0615 (5)0.17520 (6)0.2841 (2)0.0652 (7)
C140.1776 (4)0.14211 (6)0.2008 (2)0.0526 (6)
C150.3976 (5)0.14955 (6)0.0887 (2)0.0617 (7)
C160.4934 (5)0.18879 (7)0.0609 (2)0.0723 (8)
C170.4746 (6)0.26314 (7)0.1189 (3)0.0935 (10)
H20.10720.10480.13340.060
H020.390 (5)0.0258 (6)0.091 (2)0.097 (9)
H30.18320.13980.28810.063
H50.37740.032190.49240.060
H60.09210.00250.33270.057
H100.500 (4)0.1406 (6)0.481 (2)0.078 (7)
H110.574 (4)0.0953 (6)0.562 (2)0.078 (9)
H120.07720.23680.31580.085
H130.08770.17070.36130.079
H150.48150.12730.03100.074
H160.64330.19340.01590.087
H200.134 (5)0.0803 (6)0.162 (2)0.096 (9)
H210.057 (4)0.0981 (6)0.276 (2)0.056 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0491 (9)0.0533 (8)0.0542 (9)0.0077 (7)0.0128 (7)0.0026 (7)
O20.0514 (10)0.0418 (7)0.071 (1)0.0076 (7)0.0137 (8)0.0036 (7)
N10.056 (1)0.061 (1)0.064 (1)0.003 (1)0.018 (1)0.012 (1)
N20.067 (2)0.056 (1)0.068 (1)0.010 (1)0.007 (1)0.001 (1)
N30.188 (3)0.078 (1)0.135 (2)0.061 (2)0.030 (2)0.018 (1)
C10.036 (1)0.0443 (10)0.042 (1)0.0033 (9)0.0031 (8)0.0062 (9)
C20.051 (1)0.0479 (10)0.052 (1)0.000 (1)0.007 (1)0.0024 (10)
C30.055 (1)0.044 (1)0.058 (1)0.009 (1)0.006 (1)0.0025 (9)
C40.035 (1)0.056 (1)0.048 (1)0.0029 (10)0.0048 (9)0.0105 (9)
C50.044 (1)0.053 (1)0.055 (1)0.006 (1)0.011 (1)0.001 (1)
C60.042 (1)0.045 (1)0.055 (1)0.0016 (10)0.0022 (9)0.0011 (9)
C70.035 (1)0.0448 (10)0.049 (1)0.0047 (9)0.0055 (9)0.0052 (9)
C110.082 (2)0.063 (1)0.067 (2)0.017 (1)0.024 (1)0.012 (1)
C120.080 (2)0.057 (1)0.077 (2)0.002 (1)0.015 (1)0.010 (1)
C130.064 (2)0.062 (1)0.069 (2)0.003 (1)0.002 (1)0.004 (1)
C140.056 (1)0.054 (1)0.049 (1)0.004 (1)0.0130 (9)0.0031 (9)
C150.058 (2)0.067 (1)0.060 (1)0.005 (1)0.002 (1)0.006 (1)
C160.070 (2)0.080 (1)0.067 (2)0.026 (1)0.002 (1)0.003 (1)
C170.119 (3)0.073 (1)0.093 (2)0.034 (2)0.030 (2)0.012 (2)
Geometric parameters (Å, º) top
O1—C71.240 (3)C4—C51.401 (4)
O2—C71.319 (3)C5—C61.378 (4)
N1—C41.379 (4)C11—C121.382 (5)
N2—C141.368 (4)C11—C161.388 (5)
N3—C171.127 (4)C11—C171.441 (4)
C1—C21.391 (4)C12—C131.377 (4)
C1—C61.389 (4)C13—C141.385 (4)
C1—C71.472 (4)C14—C151.395 (4)
C2—C31.371 (4)C15—C161.373 (4)
C3—C41.399 (4)
C2—C1—C6118.6 (3)O2—C7—C1115.1 (3)
C2—C1—C7119.3 (3)C12—C11—C16118.9 (3)
C6—C1—C7122.1 (3)C12—C11—C17119.5 (4)
C1—C2—C3121.2 (3)C16—C11—C17121.6 (4)
C2—C3—C4120.5 (3)C11—C12—C13120.4 (4)
N1—C4—C3120.5 (3)C12—C13—C14121.1 (4)
N1—C4—C5121.0 (3)N2—C14—C13121.2 (3)
C3—C4—C5118.4 (3)N2—C14—C15120.5 (3)
C4—C5—C6120.4 (3)C13—C14—C15118.2 (3)
C1—C6—C5120.9 (3)C14—C15—C16120.6 (3)
O1—C7—O2122.1 (3)C11—C16—C15120.7 (4)
O1—C7—C1122.7 (3)N3—C17—C11179.5 (6)
 

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