N,N′-Bis­(pyridin-4-ylmethyl)succinamide–terephthalic acid (1/1)

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, C₁₆H₁₈N₄O₂·C₈H₆O₄. 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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](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

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Computing details

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)

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0704P)^2 + 0.3562P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C4A^i	1.403 (2)
C5B—C6B	1.386 (2)	C4A—C2A^i	1.403 (2)
C5B—H11	0.9500	C4A—H10	0.9500
C2B—C3B	1.384 (2)	C10B—C10B^ii	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—C11B^ii	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—C4A^i	120.28 (13)
C3B—C2B—C1B	119.78 (15)	C3A—C2A—C1A	118.75 (14)
C3B—C2B—H12	120.1	C4A^i—C2A—C1A	120.97 (14)
C1B—C2B—H12	120.1	C3A—C4A—C2A^i	118.89 (13)
N4B—C3B—C2B	122.75 (15)	C3A—C4A—H10	120.6
N4B—C3B—H13	118.6	C2A^i—C4A—H10	120.6
C2B—C3B—H13	118.6	C10B^ii—C10B—C9B	113.25 (14)
O9B—C9B—N8B	122.42 (15)	C10B^ii—C10B—H10A	108.9
O9B—C9B—C10B	121.97 (14)	C9B—C10B—H10A	108.9
N8B—C9B—C10B	115.46 (13)	C10B^ii—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—C11B^ii	101.2 (16)
C5B—C6B—H15	120.5	C9B—C11B—H11A	111.5
C1B—C6B—H15	120.5	C11B^ii—C11B—H11A	111.5
N8B—C7B—C1B	111.26 (12)	C9B—C11B—H11B	111.5
N8B—C7B—H16A	109.4	C11B^ii—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—C4A^i	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—C4A^i	−172.45 (15)
C7B—N8B—C9B—O9B	3.0 (3)	O1A—C1A—C2A—C4A^i	7.3 (2)
C7B—N8B—C9B—C10B	178.62 (14)	C2A—C3A—C4A—C2A^i	−0.1 (2)
C7B—N8B—C9B—C11B	−150.8 (8)	O9B—C9B—C10B—C10B^ii	−29.7 (2)
N4B—C5B—C6B—C1B	1.3 (3)	N8B—C9B—C10B—C10B^ii	154.72 (16)
C2B—C1B—C6B—C5B	−0.7 (2)	C11B—C9B—C10B—C10B^ii	59.0 (14)
C7B—C1B—C6B—C5B	179.20 (15)	O9B—C9B—C11B—C11B^ii	58.8 (19)
C9B—N8B—C7B—C1B	−164.72 (15)	N8B—C9B—C11B—C11B^ii	−145.9 (13)
C2B—C1B—C7B—N8B	−111.52 (17)	C10B—C9B—C11B—C11B^ii	−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)

D—H···A	D—H	H···A	D···A	D—H···A
N8B—H5···O9B^iii	0.88	2.01	2.875 (2)	166
O1A—H3···N4B^iv	0.84	1.82	2.654 (2)	175

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