The title compound, C
26H
22N
2O
4, crystallizes in an
anti-C=O orientation, with the two N-substituted benzene rings in different conformations relative to the naphthalene ring. These conformations allow two strong N—H
O hydrogen bonds and one C—H
π interaction to generate molecular chains in the cell.
Supporting information
CCDC reference: 621288
Naphthalene-1,4-dicarboxylic acid (2 mmol) and an excess of thionyl chloride in
dioxane (20 ml) were boiled under reflux for 6 h. The solution was distilled
by reduced pressure and a yellow solid was obtained. O-Anisidine (4 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled
under reflux for 1 d. The solution was then cooled to ambient temperature and
filtered to remove the tetrahydrofuran. The precipitate was dissolved in
dimethylsulfoxide and allowed to stand for one month at ambient temperature,
and colourless single crystals of (I) suitable for X-ray diffraction were
obtained.
All H atoms were placed in calculated positions and included in the final cycles
of refinement using a riding model, with N—H = 0.88 Å and C—H = 0.95 or
0.98 Å, and with Uiso(H) = 1.2Ueq(N,C).
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL97.
N,
N'-Bis(2-methoxyphenyl)naphthalene-1,4-dicarboxamide
top
Crystal data top
C26H22N2O4 | F(000) = 896 |
Mr = 426.46 | Dx = 1.352 Mg m−3 |
MonoclinicCc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 9668 reflections |
a = 34.7194 (9) Å | θ = 3.0–27.5° |
b = 6.0462 (1) Å | µ = 0.09 mm−1 |
c = 10.0042 (3) Å | T = 153 K |
β = 93.975 (1)° | Column, colourless |
V = 2095.03 (9) Å3 | 0.35 × 0.21 × 0.14 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2049 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.014 |
Graphite monochromator | θmax = 26.0°, θmin = 3.4° |
ω scans | h = −42→42 |
8696 measured reflections | k = −7→7 |
2074 independent reflections | l = −12→12 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.5976P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2074 reflections | Δρmax = 0.27 e Å−3 |
292 parameters | Δρmin = −0.21 e Å−3 |
2 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0042 (8) |
Crystal data top
C26H22N2O4 | V = 2095.03 (9) Å3 |
Mr = 426.46 | Z = 4 |
MonoclinicCc | Mo Kα radiation |
a = 34.7194 (9) Å | µ = 0.09 mm−1 |
b = 6.0462 (1) Å | T = 153 K |
c = 10.0042 (3) Å | 0.35 × 0.21 × 0.14 mm |
β = 93.975 (1)° | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2049 reflections with I > 2σ(I) |
8696 measured reflections | Rint = 0.014 |
2074 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.029 | 2 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.27 e Å−3 |
2074 reflections | Δρmin = −0.21 e Å−3 |
292 parameters | |
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 | 0.26715 (4) | 0.5097 (3) | 0.23758 (13) | 0.0243 (3) | |
O2 | 0.22530 (4) | 0.1268 (2) | 0.57759 (14) | 0.0255 (3) | |
O3 | 0.44834 (4) | 0.5514 (3) | 0.66101 (14) | 0.0267 (3) | |
O4 | 0.49031 (5) | 0.1080 (3) | 0.33995 (15) | 0.0296 (4) | |
N1 | 0.25272 (5) | 0.4794 (3) | 0.45421 (15) | 0.0177 (3) | |
H1N | 0.2615 | 0.4942 | 0.5384 | 0.021* | |
N2 | 0.46429 (5) | 0.4694 (3) | 0.45087 (16) | 0.0182 (3) | |
H2N | 0.4560 | 0.4692 | 0.3658 | 0.022* | |
C1 | 0.31914 (5) | 0.5484 (3) | 0.40293 (18) | 0.0167 (4) | |
C2 | 0.34382 (5) | 0.3959 (3) | 0.35411 (17) | 0.0190 (4) | |
H2 | 0.3342 | 0.2883 | 0.2911 | 0.023* | |
C3 | 0.38327 (5) | 0.3976 (3) | 0.39666 (17) | 0.0194 (4) | |
H3 | 0.4000 | 0.2891 | 0.3636 | 0.023* | |
C4 | 0.39798 (5) | 0.5550 (3) | 0.48565 (18) | 0.0166 (4) | |
C5 | 0.38814 (5) | 0.9061 (3) | 0.61120 (17) | 0.0190 (4) | |
H5 | 0.4149 | 0.9134 | 0.6377 | 0.023* | |
C6 | 0.36402 (6) | 1.0679 (3) | 0.65184 (18) | 0.0212 (4) | |
H6 | 0.3741 | 1.1852 | 0.7069 | 0.025* | |
C7 | 0.32411 (6) | 1.0615 (3) | 0.61225 (19) | 0.0213 (4) | |
H7 | 0.3075 | 1.1735 | 0.6416 | 0.026* | |
C8 | 0.30945 (5) | 0.8947 (3) | 0.53204 (18) | 0.0197 (4) | |
H8 | 0.2827 | 0.8941 | 0.5045 | 0.024* | |
C9 | 0.33338 (5) | 0.7222 (3) | 0.48894 (17) | 0.0158 (3) | |
C10 | 0.37386 (5) | 0.7271 (3) | 0.53005 (17) | 0.0164 (4) | |
C11 | 0.27725 (5) | 0.5161 (3) | 0.35739 (18) | 0.0155 (4) | |
C12 | 0.21345 (5) | 0.4178 (3) | 0.42651 (18) | 0.0172 (4) | |
C13 | 0.19931 (5) | 0.2342 (3) | 0.49328 (19) | 0.0199 (4) | |
C14 | 0.16084 (6) | 0.1713 (4) | 0.4682 (2) | 0.0274 (4) | |
H14 | 0.1509 | 0.0485 | 0.5141 | 0.033* | |
C15 | 0.13710 (6) | 0.2880 (4) | 0.3764 (2) | 0.0315 (5) | |
H15 | 0.1110 | 0.2438 | 0.3592 | 0.038* | |
C16 | 0.15099 (6) | 0.4683 (4) | 0.3094 (2) | 0.0312 (5) | |
H16 | 0.1346 | 0.5469 | 0.2460 | 0.037* | |
C17 | 0.18924 (6) | 0.5337 (4) | 0.3355 (2) | 0.0231 (4) | |
H17 | 0.1988 | 0.6585 | 0.2905 | 0.028* | |
C18 | 0.21267 (7) | −0.0657 (4) | 0.6459 (2) | 0.0330 (5) | |
H18A | 0.1922 | −0.0244 | 0.7038 | 0.040* | |
H18B | 0.2345 | −0.1289 | 0.7006 | 0.040* | |
H18C | 0.2027 | −0.1753 | 0.5801 | 0.040* | |
C19 | 0.43904 (6) | 0.5291 (3) | 0.54159 (19) | 0.0174 (4) | |
C20 | 0.50327 (5) | 0.4069 (3) | 0.48311 (18) | 0.0192 (4) | |
C21 | 0.51692 (6) | 0.2188 (3) | 0.42038 (19) | 0.0219 (4) | |
C22 | 0.55549 (6) | 0.1559 (4) | 0.4444 (2) | 0.0305 (5) | |
H22 | 0.5652 | 0.0307 | 0.4002 | 0.037* | |
C23 | 0.57946 (6) | 0.2768 (4) | 0.5329 (3) | 0.0347 (5) | |
H23 | 0.6056 | 0.2333 | 0.5498 | 0.042* | |
C24 | 0.56585 (6) | 0.4602 (4) | 0.5971 (2) | 0.0332 (5) | |
H24 | 0.5826 | 0.5413 | 0.6583 | 0.040* | |
C25 | 0.52750 (6) | 0.5263 (4) | 0.5718 (2) | 0.0251 (4) | |
H25 | 0.5181 | 0.6528 | 0.6154 | 0.030* | |
C26 | 0.50263 (8) | −0.0825 (4) | 0.2699 (2) | 0.0354 (5) | |
H26A | 0.5224 | −0.0393 | 0.2095 | 0.042* | |
H26B | 0.4805 | −0.1473 | 0.2177 | 0.042* | |
H26C | 0.5135 | −0.1916 | 0.3345 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0210 (7) | 0.0394 (8) | 0.0125 (7) | −0.0031 (6) | 0.0010 (5) | 0.0006 (6) |
O2 | 0.0259 (7) | 0.0235 (7) | 0.0275 (7) | −0.0002 (6) | 0.0055 (6) | 0.0094 (6) |
O3 | 0.0212 (7) | 0.0430 (8) | 0.0155 (7) | 0.0058 (6) | −0.0010 (5) | −0.0039 (6) |
O4 | 0.0320 (8) | 0.0277 (8) | 0.0287 (8) | 0.0052 (6) | −0.0007 (6) | −0.0096 (7) |
N1 | 0.0158 (7) | 0.0249 (8) | 0.0122 (7) | −0.0021 (6) | −0.0007 (6) | 0.0015 (6) |
N2 | 0.0154 (8) | 0.0261 (8) | 0.0129 (8) | 0.0030 (6) | 0.0003 (6) | −0.0009 (6) |
C1 | 0.0173 (10) | 0.0197 (9) | 0.0131 (8) | −0.0012 (7) | 0.0002 (7) | 0.0033 (7) |
C2 | 0.0206 (8) | 0.0214 (9) | 0.0151 (8) | −0.0026 (7) | 0.0015 (6) | −0.0027 (7) |
C3 | 0.0209 (9) | 0.0214 (9) | 0.0160 (8) | 0.0020 (7) | 0.0035 (7) | −0.0008 (7) |
C4 | 0.0147 (9) | 0.0210 (9) | 0.0141 (8) | 0.0005 (7) | 0.0023 (7) | 0.0012 (7) |
C5 | 0.0188 (8) | 0.0216 (9) | 0.0167 (9) | −0.0035 (7) | 0.0013 (7) | 0.0010 (7) |
C6 | 0.0278 (9) | 0.0178 (8) | 0.0182 (9) | −0.0033 (7) | 0.0024 (7) | −0.0019 (7) |
C7 | 0.0255 (9) | 0.0178 (8) | 0.0209 (9) | 0.0045 (7) | 0.0040 (7) | 0.0013 (7) |
C8 | 0.0206 (8) | 0.0211 (9) | 0.0175 (8) | 0.0015 (7) | 0.0026 (7) | 0.0033 (7) |
C9 | 0.0180 (8) | 0.0174 (8) | 0.0120 (8) | −0.0005 (7) | 0.0018 (6) | 0.0027 (6) |
C10 | 0.0179 (8) | 0.0195 (8) | 0.0121 (8) | 0.0000 (7) | 0.0023 (6) | 0.0026 (6) |
C11 | 0.0161 (9) | 0.0160 (8) | 0.0142 (9) | −0.0018 (7) | −0.0003 (7) | 0.0002 (6) |
C12 | 0.0132 (8) | 0.0220 (9) | 0.0166 (9) | 0.0001 (7) | 0.0028 (7) | −0.0034 (7) |
C13 | 0.0185 (9) | 0.0207 (9) | 0.0212 (10) | 0.0013 (7) | 0.0065 (7) | −0.0040 (7) |
C14 | 0.0224 (10) | 0.0267 (10) | 0.0342 (11) | −0.0058 (8) | 0.0104 (8) | −0.0055 (9) |
C15 | 0.0147 (9) | 0.0388 (13) | 0.0410 (13) | −0.0023 (8) | 0.0017 (8) | −0.0117 (10) |
C16 | 0.0203 (11) | 0.0414 (13) | 0.0311 (12) | 0.0070 (9) | −0.0043 (9) | −0.0026 (10) |
C17 | 0.0210 (10) | 0.0264 (10) | 0.0216 (10) | 0.0028 (8) | 0.0006 (8) | 0.0004 (8) |
C18 | 0.0434 (13) | 0.0205 (10) | 0.0371 (13) | 0.0014 (9) | 0.0169 (11) | 0.0073 (9) |
C19 | 0.0181 (9) | 0.0180 (9) | 0.0162 (9) | 0.0002 (7) | 0.0012 (7) | 0.0000 (7) |
C20 | 0.0162 (9) | 0.0247 (10) | 0.0170 (9) | 0.0008 (7) | 0.0029 (7) | 0.0036 (8) |
C21 | 0.0213 (9) | 0.0253 (10) | 0.0194 (9) | 0.0028 (8) | 0.0036 (7) | 0.0031 (7) |
C22 | 0.0246 (11) | 0.0309 (11) | 0.0371 (12) | 0.0090 (9) | 0.0104 (9) | 0.0064 (10) |
C23 | 0.0158 (9) | 0.0426 (13) | 0.0456 (14) | 0.0047 (9) | 0.0025 (9) | 0.0110 (11) |
C24 | 0.0193 (11) | 0.0396 (13) | 0.0398 (14) | −0.0066 (9) | −0.0054 (9) | 0.0050 (10) |
C25 | 0.0215 (10) | 0.0283 (11) | 0.0253 (10) | −0.0007 (8) | −0.0005 (8) | −0.0010 (8) |
C26 | 0.0511 (15) | 0.0255 (11) | 0.0303 (12) | 0.0061 (10) | 0.0082 (11) | −0.0057 (9) |
Geometric parameters (Å, º) top
O1—C11 | 1.226 (2) | C8—H8 | 0.9500 |
O2—C13 | 1.357 (2) | C9—C10 | 1.437 (2) |
O2—C18 | 1.434 (2) | C12—C17 | 1.386 (3) |
O3—C19 | 1.223 (2) | C12—C13 | 1.402 (3) |
O4—C21 | 1.359 (3) | C13—C14 | 1.395 (3) |
O4—C26 | 1.429 (3) | C14—C15 | 1.384 (3) |
N1—C11 | 1.352 (3) | C14—H14 | 0.9500 |
N1—C12 | 1.422 (2) | C15—C16 | 1.384 (4) |
N1—H1N | 0.8800 | C15—H15 | 0.9500 |
N2—C19 | 1.354 (2) | C16—C17 | 1.393 (3) |
N2—C20 | 1.420 (2) | C16—H16 | 0.9500 |
N2—H2N | 0.8800 | C17—H17 | 0.9500 |
C1—C2 | 1.372 (3) | C18—H18A | 0.9800 |
C1—C9 | 1.425 (3) | C18—H18B | 0.9800 |
C1—C11 | 1.506 (2) | C18—H18C | 0.9800 |
C2—C3 | 1.406 (2) | C20—C25 | 1.383 (3) |
C2—H2 | 0.9500 | C20—C21 | 1.398 (3) |
C3—C4 | 1.377 (3) | C21—C22 | 1.397 (3) |
C3—H3 | 0.9500 | C22—C23 | 1.381 (4) |
C4—C10 | 1.426 (3) | C22—H22 | 0.9500 |
C4—C19 | 1.503 (2) | C23—C24 | 1.381 (4) |
C5—C6 | 1.368 (3) | C23—H23 | 0.9500 |
C5—C10 | 1.421 (3) | C24—C25 | 1.397 (3) |
C5—H5 | 0.9500 | C24—H24 | 0.9500 |
C6—C7 | 1.415 (3) | C25—H25 | 0.9500 |
C6—H6 | 0.9500 | C26—H26A | 0.9800 |
C7—C8 | 1.365 (3) | C26—H26B | 0.9800 |
C7—H7 | 0.9500 | C26—H26C | 0.9800 |
C8—C9 | 1.419 (3) | | |
| | | |
C13—O2—C18 | 118.21 (17) | C14—C13—C12 | 119.50 (18) |
C21—O4—C26 | 118.27 (18) | C15—C14—C13 | 120.0 (2) |
C11—N1—C12 | 123.14 (15) | C15—C14—H14 | 120.0 |
C11—N1—H1N | 118.4 | C13—C14—H14 | 120.0 |
C12—N1—H1N | 118.4 | C14—C15—C16 | 120.77 (19) |
C19—N2—C20 | 124.74 (16) | C14—C15—H15 | 119.6 |
C19—N2—H2N | 117.6 | C16—C15—H15 | 119.6 |
C20—N2—H2N | 117.6 | C15—C16—C17 | 119.5 (2) |
C2—C1—C9 | 120.78 (17) | C15—C16—H16 | 120.3 |
C2—C1—C11 | 114.77 (17) | C17—C16—H16 | 120.3 |
C9—C1—C11 | 124.45 (16) | C12—C17—C16 | 120.4 (2) |
C1—C2—C3 | 120.44 (17) | C12—C17—H17 | 119.8 |
C1—C2—H2 | 119.8 | C16—C17—H17 | 119.8 |
C3—C2—H2 | 119.8 | O2—C18—H18A | 109.5 |
C4—C3—C2 | 120.74 (17) | O2—C18—H18B | 109.5 |
C4—C3—H3 | 119.6 | H18A—C18—H18B | 109.5 |
C2—C3—H3 | 119.6 | O2—C18—H18C | 109.5 |
C3—C4—C10 | 120.41 (17) | H18A—C18—H18C | 109.5 |
C3—C4—C19 | 117.95 (16) | H18B—C18—H18C | 109.5 |
C10—C4—C19 | 121.48 (16) | O3—C19—N2 | 123.01 (18) |
C6—C5—C10 | 121.21 (16) | O3—C19—C4 | 122.11 (17) |
C6—C5—H5 | 119.4 | N2—C19—C4 | 114.82 (16) |
C10—C5—H5 | 119.4 | C25—C20—C21 | 120.19 (18) |
C5—C6—C7 | 120.31 (17) | C25—C20—N2 | 122.31 (18) |
C5—C6—H6 | 119.8 | C21—C20—N2 | 117.49 (17) |
C7—C6—H6 | 119.8 | O4—C21—C22 | 124.9 (2) |
C8—C7—C6 | 120.20 (17) | O4—C21—C20 | 115.44 (17) |
C8—C7—H7 | 119.9 | C22—C21—C20 | 119.7 (2) |
C6—C7—H7 | 119.9 | C23—C22—C21 | 119.6 (2) |
C7—C8—C9 | 121.28 (17) | C23—C22—H22 | 120.2 |
C7—C8—H8 | 119.4 | C21—C22—H22 | 120.2 |
C9—C8—H8 | 119.4 | C24—C23—C22 | 120.8 (2) |
C8—C9—C1 | 122.65 (17) | C24—C23—H23 | 119.6 |
C8—C9—C10 | 118.66 (16) | C22—C23—H23 | 119.6 |
C1—C9—C10 | 118.66 (15) | C23—C24—C25 | 119.9 (2) |
C5—C10—C4 | 123.00 (16) | C23—C24—H24 | 120.1 |
C5—C10—C9 | 118.33 (15) | C25—C24—H24 | 120.1 |
C4—C10—C9 | 118.66 (15) | C20—C25—C24 | 119.8 (2) |
O1—C11—N1 | 122.94 (17) | C20—C25—H25 | 120.1 |
O1—C11—C1 | 120.30 (16) | C24—C25—H25 | 120.1 |
N1—C11—C1 | 116.59 (15) | O4—C26—H26A | 109.5 |
C17—C12—C13 | 119.82 (18) | O4—C26—H26B | 109.5 |
C17—C12—N1 | 121.70 (18) | H26A—C26—H26B | 109.5 |
C13—C12—N1 | 118.48 (17) | O4—C26—H26C | 109.5 |
O2—C13—C14 | 124.66 (19) | H26A—C26—H26C | 109.5 |
O2—C13—C12 | 115.83 (17) | H26B—C26—H26C | 109.5 |
| | | |
C9—C1—C2—C3 | 5.1 (3) | C18—O2—C13—C12 | −178.43 (18) |
C11—C1—C2—C3 | −175.33 (16) | C17—C12—C13—O2 | 178.11 (17) |
C1—C2—C3—C4 | −1.4 (3) | N1—C12—C13—O2 | −1.6 (3) |
C2—C3—C4—C10 | −3.8 (3) | C17—C12—C13—C14 | −0.6 (3) |
C2—C3—C4—C19 | 171.71 (16) | N1—C12—C13—C14 | 179.71 (17) |
C10—C5—C6—C7 | −0.7 (3) | O2—C13—C14—C15 | −177.62 (19) |
C5—C6—C7—C8 | −0.7 (3) | C12—C13—C14—C15 | 1.0 (3) |
C6—C7—C8—C9 | 1.4 (3) | C13—C14—C15—C16 | −0.5 (3) |
C7—C8—C9—C1 | −178.62 (17) | C14—C15—C16—C17 | −0.4 (3) |
C7—C8—C9—C10 | −0.8 (2) | C13—C12—C17—C16 | −0.3 (3) |
C2—C1—C9—C8 | 174.22 (17) | N1—C12—C17—C16 | 179.37 (19) |
C11—C1—C9—C8 | −5.3 (3) | C15—C16—C17—C12 | 0.8 (3) |
C2—C1—C9—C10 | −3.6 (3) | C20—N2—C19—O3 | 5.8 (3) |
C11—C1—C9—C10 | 176.88 (15) | C20—N2—C19—C4 | −171.22 (17) |
C6—C5—C10—C4 | −179.93 (17) | C3—C4—C19—O3 | −134.0 (2) |
C6—C5—C10—C9 | 1.3 (2) | C10—C4—C19—O3 | 41.5 (3) |
C3—C4—C10—C5 | −173.65 (17) | C3—C4—C19—N2 | 43.0 (2) |
C19—C4—C10—C5 | 11.0 (3) | C10—C4—C19—N2 | −141.52 (17) |
C3—C4—C10—C9 | 5.1 (2) | C19—N2—C20—C25 | −46.2 (3) |
C19—C4—C10—C9 | −170.22 (15) | C19—N2—C20—C21 | 134.5 (2) |
C8—C9—C10—C5 | −0.6 (2) | C26—O4—C21—C22 | −2.6 (3) |
C1—C9—C10—C5 | 177.37 (16) | C26—O4—C21—C20 | 178.31 (19) |
C8—C9—C10—C4 | −179.39 (17) | C25—C20—C21—O4 | 177.09 (18) |
C1—C9—C10—C4 | −1.4 (2) | N2—C20—C21—O4 | −3.6 (3) |
C12—N1—C11—O1 | 3.6 (3) | C25—C20—C21—C22 | −2.0 (3) |
C12—N1—C11—C1 | −171.64 (16) | N2—C20—C21—C22 | 177.32 (18) |
C2—C1—C11—O1 | −56.1 (2) | O4—C21—C22—C23 | −177.2 (2) |
C9—C1—C11—O1 | 123.4 (2) | C20—C21—C22—C23 | 1.8 (3) |
C2—C1—C11—N1 | 119.28 (18) | C21—C22—C23—C24 | −0.5 (4) |
C9—C1—C11—N1 | −61.2 (2) | C22—C23—C24—C25 | −0.6 (4) |
C11—N1—C12—C17 | −50.0 (3) | C21—C20—C25—C24 | 1.0 (3) |
C11—N1—C12—C13 | 129.65 (19) | N2—C20—C25—C24 | −178.37 (19) |
C18—O2—C13—C14 | 0.2 (3) | C23—C24—C25—C20 | 0.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.88 | 1.99 | 2.845 (2) | 164 |
N2—H2N···O3ii | 0.88 | 2.05 | 2.917 (2) | 168 |
C2—H2···Cg2ii | 0.95 | 2.55 | 3.353 (2) | 142 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+1, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C26H22N2O4 |
Mr | 426.46 |
Crystal system, space group | MonoclinicCc |
Temperature (K) | 153 |
a, b, c (Å) | 34.7194 (9), 6.0462 (1), 10.0042 (3) |
β (°) | 93.975 (1) |
V (Å3) | 2095.03 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.21 × 0.14 |
|
Data collection |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8696, 2074, 2049 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.080, 1.06 |
No. of reflections | 2074 |
No. of parameters | 292 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.21 |
Selected geometric parameters (Å, º) topN1—C11 | 1.352 (3) | N2—C20 | 1.420 (2) |
N1—C12 | 1.422 (2) | C1—C11 | 1.506 (2) |
N2—C19 | 1.354 (2) | C4—C19 | 1.503 (2) |
| | | |
C11—N1—C12 | 123.14 (15) | C19—N2—C20 | 124.74 (16) |
| | | |
C12—N1—C11—C1 | −171.64 (16) | C20—N2—C19—C4 | −171.22 (17) |
C2—C1—C11—N1 | 119.28 (18) | C3—C4—C19—N2 | 43.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.88 | 1.99 | 2.845 (2) | 164.0 |
N2—H2N···O3ii | 0.88 | 2.05 | 2.917 (2) | 168.0 |
C2—H2···Cg2ii | 0.95 | 2.55 | 3.353 (2) | 142.0 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+1, z−1/2. |
Non-covalent interactions, such as hydrogen bonding, π–π stacking and C—H···π interactions, play a dominant role in supramolecular self-assembly (Casnati et al., 2003; Ghosh & Bharadwaj, 2004; Glidewell et al., 2005; Jennings et al., 2001). Moreover, the conformations of the molecular building blocks have an important influence on the supramolecular structure. In order to further understanding of supramolecular self-assembly through non-covalent interactions, we have designed and synthesized an N-substituted aromatic acylamide, the title compound, (I), a member of the 1,4-naphthalenecarboxamide family. These compounds are used as optical brightening agents (Farbwerke Hoechst, 1965), optical whiteners (Farbwerke Hoechst, 1969), chemotherapeutic agents (Wander, 1965; Cain et al., 1969) and reagents for oligomers and polymers (Masu et al., 2005; Hsiao & Chang, 2004). We report here the structure of (I) (Fig. 1, Table 1).
As in the case of the related compounds N,N'-dimethyl-1,4-naphthalenecarboxamide [Cambridge Structural database (CSD, Version?; Allen 2002) refcode RAPYUC; Lewis et al., 1996], and 8-methoxy-N-phenyl-1-naphthamide and 8-(dimethylamino)-N-phenyl-1-naphthamide (TAWRIT02 and TAWROZ, respectively; O'Leary et al., 2005), the naphthalene ring system of (I), containing two planar benzene rings, C1–C4/C9/C10 and C5–C10, with maximum deviations of 0.031 (2) and -0.007 (3) Å for atoms C4 and C8, respectively, is slightly distorted from planarity, with an interplanar angle of 3.4 (1)°. The corresponding angles for RAPYUC, TAWRIT02 and TAWROZ are 1.72 (7), 4.8 (1) and 4.6 (1)°, respectively. In (I), consistent with intermolecular packing interactions (see below), the substituent groups at atoms C1 and C4 are twisted away from the naphthalene ring system (Table 1). Thus, the planes C12–C17 and C1–C4/C9/C10 form a dihedral angle of 72.5 (1)°, while the planes C20–C25 and C1–C4/C9/C10 are almost parallel, with a dihedral angle of 5.0 (1)°.
The O1/N1/C11/C12 and O3/N2/C19/C20 planes form dihedral angles of 60.4 (1) and 43.8 (1)°, respectively, with the napthalene plane. The other two benzene rings of (I), C12–C17 and C20–C25, are coplanar, with maximum deviations of -0.005 (2) and 0.011 (1) Å for atoms C13 and C21, respectively. These two benzene planes, C12–C17 and C20–C25, have an interplanar angle of 72.0 (1)°, quite different from the crystallographically enforced parallel ring planes (0°) found in the related structures N,N'-diphenylterephthalamide (CSD refcode DPTPAM; Harkema et al., 1979) and 2,4,2',4'-tetranitro-N,N'-diphenylterephthalamide (CSD refcode FENPET; Novozhilova et al., 1986)·The two planes O1/N1/C11/C12 and C12–C17 subtend a dihedral angle of 48.1 (1)°, while the two planes O3/N2/C19/C20 and C20–C25 make a dihedral angle of 42.5 (1)° (Fig. 1). Because of the sp2 hybridization of atoms N1 and N2, partial double-bond character is observed in the identical N1—C11/N2—C19 and N1—C12/N2—C20 linkages [average N—C bond lengths 1.353 (2) and 1.421 (2) Å, respectively].
The observed anti-C═O orientation of (I) (Fig. 1) differs from the reported cis-C═O orientation in the closest related structure, RAPYUC. The packing structure of (I) involves two strong intermolecular N—H···O hydrogen bonds (Steiner, 2002) (Table 2), which link adjacent molecules into a one-dimensional chain, running parallel to the [001] direction, with a graph-set motif of R22(18) (Bernstein et al., 1995) (Fig. 2). A similar hydrogen-bond network is found in N,N'-dimethyl-1,4'-phenylenediacetamide, N,N'-dimethyl-4,4'-biphenyldicarboxamide, N,N'-dimethyl-4,4'-stilbenedicarboxamide and N,N'-dimethyl-4,4'-diphenylacetylenedicarboxamide (CSD refcodes RAPYIQ, ZUKJUK10, ZUKJOE10 and ZUKKAR10, respectively; Lewis et al., 1996). Within the chain between adjacent molecules, there is also a classical intermolecular C—H···π hydrogen bond (Desiraju & Steiner, 1999) (Fig. 2 and Table 2; Cg2 is the centroid of the C5–C10 ring). There are no significant interactions between adjacent chains.