Alternate molecules of
N,
N′-bis(pyridin-4-ylmethyl)succinamide and terephthalic acid, each of which is located about a centre of inversion, are linked by strong O—H
N hydrogen bonds to form strands in the title compound, C
16H
18N
4O
2·C
8H
6O
4. In addition, strong N—H
O hydrogen bonds between the
N,
N′-bis(pyridin-4-ylmethyl)succinamide molecules of adjacent strands link the latter to form sheets.
Supporting information
CCDC reference: 282681
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.054
- wR factor = 0.146
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 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
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Atwood & Barbour, 2003).
N,
N'-bis(pyridin-4-ylmethyl)succinamide–terephthalic acid (1/1)
top
Crystal data top
C16H18N4O2·C8H6O4 | Z = 1 |
Mr = 464.47 | F(000) = 244 |
Triclinic, P1 | Dx = 1.460 Mg m−3 |
Hall symbol: -P1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.8721 (13) Å | Cell parameters from 2080 reflections |
b = 9.550 (3) Å | θ = 2.6–28.3° |
c = 11.547 (3) Å | µ = 0.11 mm−1 |
α = 96.582 (4)° | T = 100 K |
β = 95.944 (4)° | Plates, colourless |
γ = 94.753 (4)° | 0.30 × 0.30 × 0.10 mm |
V = 528.4 (3) Å3 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 2330 independent reflections |
Radiation source: fine-focus sealed tube | 2156 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 28.2°, θmin = 1.8° |
Absorption correction: multi-scan (Blessing, 1995) | h = −6→6 |
Tmin = 0.973, Tmax = 0.989 | k = −12→11 |
3480 measured reflections | l = −15→11 |
Refinement top
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) = 0.146 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0704P)2 + 0.3562P] where P = (Fo2 + 2Fc2)/3 |
2330 reflections | (Δ/σ)max < 0.001 |
155 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−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 | Uiso*/Ueq | Occ. (<1) |
O9B | 0.2812 (2) | 0.67174 (13) | 0.39791 (11) | 0.0206 (3) | |
N4B | −0.6616 (3) | 1.14377 (14) | 0.23942 (12) | 0.0171 (3) | |
N8B | −0.1477 (3) | 0.74241 (14) | 0.36740 (12) | 0.0159 (3) | |
H5 | −0.3203 | 0.7349 | 0.3838 | 0.019* | |
C1B | −0.2717 (3) | 0.94885 (17) | 0.27306 (14) | 0.0154 (3) | |
C5B | −0.5089 (3) | 1.14620 (18) | 0.34315 (15) | 0.0192 (4) | |
H11 | −0.5347 | 1.2166 | 0.4052 | 0.023* | |
C2B | −0.4285 (3) | 0.94767 (17) | 0.16569 (14) | 0.0169 (3) | |
H12 | −0.4041 | 0.8802 | 0.1014 | 0.020* | |
C3B | −0.6207 (3) | 1.04521 (17) | 0.15246 (14) | 0.0178 (3) | |
H13 | −0.7282 | 1.0420 | 0.0785 | 0.021* | |
C9B | 0.0341 (3) | 0.66138 (17) | 0.41422 (15) | 0.0178 (3) | |
C6B | −0.3153 (3) | 1.05104 (18) | 0.36435 (15) | 0.0189 (4) | |
H15 | −0.2139 | 1.0552 | 0.4397 | 0.023* | |
C7B | −0.0619 (3) | 0.84318 (17) | 0.28929 (15) | 0.0181 (4) | |
H16A | −0.0393 | 0.7914 | 0.2121 | 0.022* | |
H16B | 0.1197 | 0.8940 | 0.3224 | 0.022* | |
O1B | 0.0119 (3) | 0.77301 (13) | −0.00313 (11) | 0.0215 (3) | |
O1A | 0.0453 (2) | 0.68403 (12) | −0.18870 (10) | 0.0192 (3) | |
H3 | −0.0690 | 0.7425 | −0.2038 | 0.023* | |
C1A | 0.1078 (3) | 0.69211 (16) | −0.07418 (14) | 0.0155 (3) | |
C3A | 0.3680 (3) | 0.57972 (17) | 0.08183 (14) | 0.0166 (3) | |
H8 | 0.2768 | 0.6345 | 0.1374 | 0.020* | |
C2A | 0.3118 (3) | 0.59200 (16) | −0.03722 (14) | 0.0147 (3) | |
C4A | 0.5558 (2) | 0.48835 (14) | 0.12034 (12) | 0.0161 (3) | |
H10 | 0.5938 | 0.4805 | 0.2016 | 0.019* | |
C10B | −0.0778 (2) | 0.56377 (14) | 0.49584 (12) | 0.0227 (7) | 0.858 (7) |
H10A | −0.0698 | 0.6170 | 0.5751 | 0.027* | 0.858 (7) |
H10B | −0.2748 | 0.5325 | 0.4681 | 0.027* | 0.858 (7) |
C11B | −0.098 (4) | 0.511 (2) | 0.4419 (17) | 0.040* | 0.142 (7) |
H11A | −0.0852 | 0.4348 | 0.3771 | 0.048* | 0.142 (7) |
H11B | −0.2934 | 0.5137 | 0.4570 | 0.048* | 0.142 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O9B | 0.0124 (5) | 0.0242 (6) | 0.0284 (7) | 0.0055 (4) | 0.0044 (5) | 0.0118 (5) |
N4B | 0.0154 (6) | 0.0163 (7) | 0.0208 (7) | 0.0038 (5) | 0.0030 (5) | 0.0052 (5) |
N8B | 0.0109 (6) | 0.0178 (7) | 0.0210 (7) | 0.0036 (5) | 0.0035 (5) | 0.0077 (5) |
C1B | 0.0134 (7) | 0.0156 (7) | 0.0191 (8) | 0.0035 (6) | 0.0046 (6) | 0.0069 (6) |
C5B | 0.0194 (8) | 0.0186 (8) | 0.0196 (8) | 0.0054 (6) | 0.0012 (6) | 0.0005 (6) |
C2B | 0.0179 (7) | 0.0169 (8) | 0.0168 (8) | 0.0039 (6) | 0.0034 (6) | 0.0027 (6) |
C3B | 0.0168 (7) | 0.0194 (8) | 0.0177 (8) | 0.0021 (6) | 0.0005 (6) | 0.0048 (6) |
C9B | 0.0138 (7) | 0.0191 (8) | 0.0220 (8) | 0.0031 (6) | 0.0020 (6) | 0.0079 (6) |
C6B | 0.0179 (8) | 0.0219 (8) | 0.0173 (8) | 0.0053 (6) | −0.0001 (6) | 0.0035 (6) |
C7B | 0.0162 (7) | 0.0204 (8) | 0.0212 (8) | 0.0067 (6) | 0.0067 (6) | 0.0094 (6) |
O1B | 0.0231 (6) | 0.0207 (6) | 0.0214 (6) | 0.0120 (5) | 0.0000 (5) | 0.0006 (5) |
O1A | 0.0192 (6) | 0.0215 (6) | 0.0186 (6) | 0.0110 (5) | 0.0001 (5) | 0.0050 (5) |
C1A | 0.0134 (7) | 0.0142 (7) | 0.0191 (8) | 0.0025 (5) | 0.0006 (6) | 0.0034 (6) |
C3A | 0.0161 (7) | 0.0157 (7) | 0.0186 (8) | 0.0050 (6) | 0.0027 (6) | 0.0012 (6) |
C2A | 0.0117 (7) | 0.0127 (7) | 0.0199 (8) | 0.0026 (5) | 0.0009 (6) | 0.0032 (6) |
C4A | 0.0165 (7) | 0.0165 (7) | 0.0156 (7) | 0.0043 (6) | 0.0003 (6) | 0.0027 (6) |
C10B | 0.0161 (9) | 0.0238 (12) | 0.0352 (15) | 0.0101 (8) | 0.0114 (9) | 0.0196 (11) |
Geometric parameters (Å, º) top
O9B—C9B | 1.235 (2) | C7B—H16B | 0.9900 |
N4B—C3B | 1.338 (2) | O1B—C1A | 1.217 (2) |
N4B—C5B | 1.340 (2) | O1A—C1A | 1.318 (2) |
N8B—C9B | 1.337 (2) | O1A—H3 | 0.8400 |
N8B—C7B | 1.458 (2) | C1A—C2A | 1.499 (2) |
N8B—H5 | 0.8800 | C3A—C4A | 1.391 (2) |
C1B—C2B | 1.386 (2) | C3A—C2A | 1.394 (2) |
C1B—C6B | 1.398 (2) | C3A—H8 | 0.9500 |
C1B—C7B | 1.508 (2) | C2A—C4Ai | 1.403 (2) |
C5B—C6B | 1.386 (2) | C4A—C2Ai | 1.403 (2) |
C5B—H11 | 0.9500 | C4A—H10 | 0.9500 |
C2B—C3B | 1.384 (2) | C10B—C10Bii | 1.494 (2) |
C2B—H12 | 0.9500 | C10B—H10A | 0.9900 |
C3B—H13 | 0.9500 | C10B—H10B | 0.9900 |
C9B—C10B | 1.509 (2) | C11B—C11Bii | 1.60 (4) |
C9B—C11B | 1.607 (18) | C11B—H11A | 0.9900 |
C6B—H15 | 0.9500 | C11B—H11B | 0.9900 |
C7B—H16A | 0.9900 | | |
| | | |
C3B—N4B—C5B | 117.75 (14) | C1B—C7B—H16B | 109.4 |
C9B—N8B—C7B | 120.40 (13) | H16A—C7B—H16B | 108.0 |
C9B—N8B—H5 | 119.8 | C1A—O1A—H3 | 109.5 |
C7B—N8B—H5 | 119.8 | O1B—C1A—O1A | 124.10 (14) |
C2B—C1B—C6B | 117.61 (14) | O1B—C1A—C2A | 121.93 (15) |
C2B—C1B—C7B | 120.55 (14) | O1A—C1A—C2A | 113.97 (13) |
C6B—C1B—C7B | 121.84 (15) | C4A—C3A—C2A | 120.83 (14) |
N4B—C5B—C6B | 123.18 (15) | C4A—C3A—H8 | 119.6 |
N4B—C5B—H11 | 118.4 | C2A—C3A—H8 | 119.6 |
C6B—C5B—H11 | 118.4 | C3A—C2A—C4Ai | 120.28 (13) |
C3B—C2B—C1B | 119.78 (15) | C3A—C2A—C1A | 118.75 (14) |
C3B—C2B—H12 | 120.1 | C4Ai—C2A—C1A | 120.97 (14) |
C1B—C2B—H12 | 120.1 | C3A—C4A—C2Ai | 118.89 (13) |
N4B—C3B—C2B | 122.75 (15) | C3A—C4A—H10 | 120.6 |
N4B—C3B—H13 | 118.6 | C2Ai—C4A—H10 | 120.6 |
C2B—C3B—H13 | 118.6 | C10Bii—C10B—C9B | 113.25 (14) |
O9B—C9B—N8B | 122.42 (15) | C10Bii—C10B—H10A | 108.9 |
O9B—C9B—C10B | 121.97 (14) | C9B—C10B—H10A | 108.9 |
N8B—C9B—C10B | 115.46 (13) | C10Bii—C10B—H10B | 108.9 |
O9B—C9B—C11B | 117.4 (7) | C9B—C10B—H10B | 108.9 |
N8B—C9B—C11B | 115.0 (7) | H10A—C10B—H10B | 107.7 |
C5B—C6B—C1B | 118.92 (15) | C9B—C11B—C11Bii | 101.2 (16) |
C5B—C6B—H15 | 120.5 | C9B—C11B—H11A | 111.5 |
C1B—C6B—H15 | 120.5 | C11Bii—C11B—H11A | 111.5 |
N8B—C7B—C1B | 111.26 (12) | C9B—C11B—H11B | 111.5 |
N8B—C7B—H16A | 109.4 | C11Bii—C11B—H11B | 111.5 |
C1B—C7B—H16A | 109.4 | H11A—C11B—H11B | 109.3 |
N8B—C7B—H16B | 109.4 | | |
| | | |
C3B—N4B—C5B—C6B | −0.8 (2) | C4A—C3A—C2A—C4Ai | 0.1 (2) |
C6B—C1B—C2B—C3B | −0.3 (2) | C4A—C3A—C2A—C1A | −179.95 (13) |
C7B—C1B—C2B—C3B | 179.81 (14) | O1B—C1A—C2A—C3A | 7.6 (2) |
C5B—N4B—C3B—C2B | −0.3 (2) | O1A—C1A—C2A—C3A | −172.59 (14) |
C1B—C2B—C3B—N4B | 0.8 (2) | O1B—C1A—C2A—C4Ai | −172.45 (15) |
C7B—N8B—C9B—O9B | 3.0 (3) | O1A—C1A—C2A—C4Ai | 7.3 (2) |
C7B—N8B—C9B—C10B | 178.62 (14) | C2A—C3A—C4A—C2Ai | −0.1 (2) |
C7B—N8B—C9B—C11B | −150.8 (8) | O9B—C9B—C10B—C10Bii | −29.7 (2) |
N4B—C5B—C6B—C1B | 1.3 (3) | N8B—C9B—C10B—C10Bii | 154.72 (16) |
C2B—C1B—C6B—C5B | −0.7 (2) | C11B—C9B—C10B—C10Bii | 59.0 (14) |
C7B—C1B—C6B—C5B | 179.20 (15) | O9B—C9B—C11B—C11Bii | 58.8 (19) |
C9B—N8B—C7B—C1B | −164.72 (15) | N8B—C9B—C11B—C11Bii | −145.9 (13) |
C2B—C1B—C7B—N8B | −111.52 (17) | C10B—C9B—C11B—C11Bii | −48.4 (13) |
C6B—C1B—C7B—N8B | 68.62 (19) | | |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N8B—H5···O9Biii | 0.88 | 2.01 | 2.875 (2) | 166 |
O1A—H3···N4Biv | 0.84 | 1.82 | 2.654 (2) | 175 |
Symmetry codes: (iii) x−1, y, z; (iv) −x−1, −y+2, −z. |