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In the title structure, C24H32N2O2, the molecule lies on a crystallographic inversion centre at the mid-point of the central C-C bond. The planar OCN-(CH2)n-NCO segment is in an all-trans configuration. The NH group of the amide group is involved in a single hydrogen bond to the O atom of a symmetry-related molecule to form one-dimensional ribbons parallel to the b direction.
Supporting information
CCDC reference: 608456
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.166
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.30
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (Maris, 2004).
N,
N'-Octamethylenebis(4-methylbenzamide)
top
Crystal data top
C24H32N2O2 | F(000) = 412 |
Mr = 380.52 | Dx = 1.219 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2yn | Cell parameters from 1367 reflections |
a = 7.1190 (2) Å | θ = 3.1–67.8° |
b = 5.1609 (2) Å | µ = 0.60 mm−1 |
c = 28.4022 (10) Å | T = 100 K |
β = 96.679 (2)° | Platelet, colourless |
V = 1036.43 (6) Å3 | 0.19 × 0.14 × 0.10 mm |
Z = 2 | |
Data collection top
Bruker SMART 6000 diffractometer | 1885 independent reflections |
Radiation source: Sealed Tube | 1340 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
Detector resolution: 5.5 pixels mm-1 | θmax = 68.8°, θmin = 3.1° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −5→5 |
Tmin = 0.901, Tmax = 0.943 | l = −34→33 |
14187 measured reflections | |
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) = 0.166 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0755P)2 + 0.2277P] where P = (Fo2 + 2Fc2)/3 |
1885 reflections | (Δ/σ)max = 0.001 |
128 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.26 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 | |
O1 | 0.2024 (2) | −0.1802 (3) | 0.89590 (6) | 0.0236 (4) | |
N1 | 0.2799 (2) | 0.2438 (3) | 0.90403 (6) | 0.0181 (5) | |
H1 | 0.2530 | 0.4049 | 0.8957 | 0.022* | |
C1 | 0.9171 (3) | 0.5392 (4) | 0.98198 (7) | 0.0176 (5) | |
H1A | 0.8589 | 0.6988 | 0.9931 | 0.021* | |
H1B | 0.9648 | 0.5794 | 0.9514 | 0.021* | |
C2 | 0.7663 (3) | 0.3291 (4) | 0.97398 (8) | 0.0188 (5) | |
H2A | 0.8244 | 0.1718 | 0.9620 | 0.023* | |
H2B | 0.7228 | 0.2848 | 1.0049 | 0.023* | |
C3 | 0.5950 (3) | 0.4032 (4) | 0.93945 (7) | 0.0179 (5) | |
H3A | 0.5378 | 0.5639 | 0.9504 | 0.021* | |
H3B | 0.6351 | 0.4368 | 0.9078 | 0.021* | |
C4 | 0.4503 (3) | 0.1870 (4) | 0.93599 (8) | 0.0179 (5) | |
H4A | 0.5092 | 0.0277 | 0.9250 | 0.021* | |
H4B | 0.4142 | 0.1520 | 0.9680 | 0.021* | |
C5 | 0.1638 (3) | 0.0517 (4) | 0.88733 (7) | 0.0168 (5) | |
C6 | −0.0168 (3) | 0.1257 (4) | 0.85837 (7) | 0.0165 (5) | |
C7 | −0.0354 (3) | 0.3451 (4) | 0.82964 (8) | 0.0197 (5) | |
H7 | 0.0696 | 0.4573 | 0.8282 | 0.024* | |
C8 | −0.2072 (3) | 0.4006 (4) | 0.80303 (8) | 0.0215 (5) | |
H8 | −0.2172 | 0.5492 | 0.7832 | 0.026* | |
C9 | −0.3648 (3) | 0.2433 (4) | 0.80485 (8) | 0.0217 (5) | |
C10 | −0.3457 (3) | 0.0248 (4) | 0.83371 (8) | 0.0224 (5) | |
H10 | −0.4518 | −0.0847 | 0.8357 | 0.027* | |
C11 | −0.1737 (3) | −0.0355 (4) | 0.85971 (8) | 0.0195 (5) | |
H11 | −0.1627 | −0.1879 | 0.8786 | 0.023* | |
C12 | −0.5508 (3) | 0.3123 (5) | 0.77696 (9) | 0.0297 (6) | |
H12A | −0.6332 | 0.1596 | 0.7743 | 0.044* | |
H12B | −0.5290 | 0.3709 | 0.7452 | 0.044* | |
H12C | −0.6113 | 0.4513 | 0.7932 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0232 (8) | 0.0090 (8) | 0.0369 (9) | −0.0004 (6) | −0.0033 (7) | 0.0018 (7) |
N1 | 0.0187 (10) | 0.0085 (10) | 0.0257 (10) | −0.0002 (6) | −0.0030 (7) | 0.0030 (7) |
C1 | 0.0190 (11) | 0.0081 (11) | 0.0253 (12) | 0.0010 (8) | 0.0009 (9) | 0.0021 (8) |
C2 | 0.0202 (11) | 0.0088 (11) | 0.0270 (12) | −0.0007 (8) | 0.0014 (9) | 0.0010 (8) |
C3 | 0.0198 (11) | 0.0087 (11) | 0.0248 (12) | 0.0002 (8) | 0.0011 (9) | −0.0001 (8) |
C4 | 0.0158 (11) | 0.0115 (11) | 0.0257 (11) | −0.0001 (8) | −0.0007 (8) | 0.0027 (8) |
C5 | 0.0188 (11) | 0.0075 (11) | 0.0241 (12) | −0.0013 (8) | 0.0027 (9) | 0.0003 (8) |
C6 | 0.0190 (11) | 0.0069 (11) | 0.0235 (11) | 0.0015 (8) | 0.0018 (8) | −0.0032 (8) |
C7 | 0.0221 (11) | 0.0116 (11) | 0.0254 (12) | −0.0005 (8) | 0.0033 (9) | 0.0003 (8) |
C8 | 0.0248 (12) | 0.0154 (11) | 0.0233 (12) | 0.0030 (9) | −0.0013 (9) | 0.0007 (8) |
C9 | 0.0216 (12) | 0.0186 (13) | 0.0243 (12) | 0.0036 (9) | 0.0000 (9) | −0.0051 (9) |
C10 | 0.0196 (11) | 0.0178 (13) | 0.0299 (13) | −0.0024 (8) | 0.0029 (9) | −0.0045 (9) |
C11 | 0.0204 (11) | 0.0101 (11) | 0.0275 (12) | −0.0032 (8) | 0.0008 (9) | 0.0014 (8) |
C12 | 0.0235 (12) | 0.0292 (14) | 0.0347 (14) | 0.0045 (10) | −0.0031 (10) | −0.0030 (10) |
Geometric parameters (Å, º) top
O1—C5 | 1.246 (3) | C5—C6 | 1.493 (3) |
N1—C5 | 1.341 (3) | C6—C7 | 1.393 (3) |
N1—C4 | 1.458 (3) | C6—C11 | 1.397 (3) |
N1—H1 | 0.8800 | C7—C8 | 1.391 (3) |
C1—C2 | 1.524 (3) | C7—H7 | 0.9500 |
C1—C1i | 1.525 (4) | C8—C9 | 1.390 (3) |
C1—H1A | 0.9900 | C8—H8 | 0.9500 |
C1—H1B | 0.9900 | C9—C10 | 1.392 (3) |
C2—C3 | 1.522 (3) | C9—C12 | 1.504 (3) |
C2—H2A | 0.9900 | C10—C11 | 1.390 (3) |
C2—H2B | 0.9900 | C10—H10 | 0.9500 |
C3—C4 | 1.514 (3) | C11—H11 | 0.9500 |
C3—H3A | 0.9900 | C12—H12A | 0.9800 |
C3—H3B | 0.9900 | C12—H12B | 0.9800 |
C4—H4A | 0.9900 | C12—H12C | 0.9800 |
C4—H4B | 0.9900 | | |
| | | |
C5—N1—C4 | 120.37 (17) | O1—C5—N1 | 121.88 (19) |
C5—N1—H1 | 119.8 | O1—C5—C6 | 120.65 (18) |
C4—N1—H1 | 119.8 | N1—C5—C6 | 117.47 (18) |
C2—C1—C1i | 112.8 (2) | C7—C6—C11 | 118.6 (2) |
C2—C1—H1A | 109.0 | C7—C6—C5 | 123.22 (19) |
C1i—C1—H1A | 109.0 | C11—C6—C5 | 118.20 (18) |
C2—C1—H1B | 109.0 | C8—C7—C6 | 120.2 (2) |
C1i—C1—H1B | 109.0 | C8—C7—H7 | 119.9 |
H1A—C1—H1B | 107.8 | C6—C7—H7 | 119.9 |
C3—C2—C1 | 114.50 (18) | C9—C8—C7 | 121.5 (2) |
C3—C2—H2A | 108.6 | C9—C8—H8 | 119.3 |
C1—C2—H2A | 108.6 | C7—C8—H8 | 119.3 |
C3—C2—H2B | 108.6 | C8—C9—C10 | 118.1 (2) |
C1—C2—H2B | 108.6 | C8—C9—C12 | 120.5 (2) |
H2A—C2—H2B | 107.6 | C10—C9—C12 | 121.4 (2) |
C4—C3—C2 | 110.16 (17) | C11—C10—C9 | 120.9 (2) |
C4—C3—H3A | 109.6 | C11—C10—H10 | 119.5 |
C2—C3—H3A | 109.6 | C9—C10—H10 | 119.5 |
C4—C3—H3B | 109.6 | C10—C11—C6 | 120.7 (2) |
C2—C3—H3B | 109.6 | C10—C11—H11 | 119.7 |
H3A—C3—H3B | 108.1 | C6—C11—H11 | 119.7 |
N1—C4—C3 | 113.77 (17) | C9—C12—H12A | 109.5 |
N1—C4—H4A | 108.8 | C9—C12—H12B | 109.5 |
C3—C4—H4A | 108.8 | H12A—C12—H12B | 109.5 |
N1—C4—H4B | 108.8 | C9—C12—H12C | 109.5 |
C3—C4—H4B | 108.8 | H12A—C12—H12C | 109.5 |
H4A—C4—H4B | 107.7 | H12B—C12—H12C | 109.5 |
| | | |
C1i—C1—C2—C3 | 178.1 (2) | C11—C6—C7—C8 | 0.0 (3) |
C1—C2—C3—C4 | −177.17 (18) | C5—C6—C7—C8 | 179.04 (19) |
C5—N1—C4—C3 | 161.85 (19) | C6—C7—C8—C9 | 1.1 (3) |
C2—C3—C4—N1 | 179.17 (17) | C7—C8—C9—C10 | −0.9 (3) |
C4—N1—C5—O1 | −4.5 (3) | C7—C8—C9—C12 | 178.0 (2) |
C4—N1—C5—C6 | 174.55 (17) | C8—C9—C10—C11 | −0.5 (3) |
O1—C5—C6—C7 | −149.5 (2) | C12—C9—C10—C11 | −179.3 (2) |
N1—C5—C6—C7 | 31.4 (3) | C9—C10—C11—C6 | 1.6 (3) |
O1—C5—C6—C11 | 29.5 (3) | C7—C6—C11—C10 | −1.3 (3) |
N1—C5—C6—C11 | −149.6 (2) | C5—C6—C11—C10 | 179.58 (19) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.88 | 2.17 | 3.027 (2) | 164 |
Symmetry code: (ii) x, y+1, z. |
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