Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040767/kp2131sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040767/kp2131Isup2.hkl |
CCDC reference: 660335
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.123
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.22 From the CIF: _diffrn_reflns_theta_full 68.22 From the CIF: _reflns_number_total 1909 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2011 Completeness (_total/calc) 94.93% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95
0 ALERT level A = In general: serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Three related structural studies of the peryleneimide moiety have been reported: the solvent-free compound (Tojo & Mizuguchi, 2002), the phenol-solvated compound (Mizuguchi & Hino, 2005) and the cresol-solvated compound (Hino & Mizuguchi, 2005). For related literature, see: Herbst & Hunger (1993); Mizuguchi et al. (2006).
PyENI was synthesized by reaction of naphthalenetracarboxylic dianhydride with 1,2-(4-pyridyl)diamine in dimethylnaphthalene at 453 K for 7 h according to the method reported (Herbst & Hunger, 1993). Single crystals of PyENI were grown by recrystallization from solution in dimethylsulfoxide. After 36 h platelet crystals suitable for X-ray analysis were obtained.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.95 and 0.99 A, and Uiso (H) = 1.2 Ueq (C).
The title compound (PyENI) is an organic pigment which belongs to the category of perylene and perinone pigments (Herbst & Hunger, 1993). The perylene and perinone pigments differ in the central skeleton being perylene or naphthalene, respectively. We were previously involved in the study of the crystal and electronic structures of pyridylethylnaphthaleneimide (PyEPI) (Mizuguchi et al., 2006). In PyEPI there are two structural isomers in the solid state: the cis form (two pyridylethylgroups are on the same side as characterized by vivid red color; Tojo & Mizuguchi, 2002) and the trans form (across the perylene skeleton as characterized by black color; Mizuguchi & Hino, 2005; Hino & Mizuguchi, 2005). Surprising to say, the trans form (black) is found to be easily transformed into the cis one (red) by heating above 373 K for several s. This phase transformation has prompted us to investigate the crystal structure of PyENI in order to study whether the similar phenomenon occurrs at the shorter wavelengths.
The title molecule is centrosymmetric (Fig. 1) and an asymmetric unit comprises a half of the molecule. Therefore, pyridylethyl groups are arranged in a trans fashion across the naphthaleneimide skeleton. The pyridyl rings and naphthaleneimide skeleton are twisted by 9.45 (5)°. The crystal packing of (I) (Fig. 2) is dominated by van der Waals interactions. The present molecular arrangement of PyENI contrasts remarkably with that of PyEPI where the molecules are involved in π ···π interactions with separation distance of about 3.3 - 3.5 Å.
Three related structural studies of the peryleneimide moiety have been reported: the solvent-free compound (Tojo & Mizuguchi, 2002), the phenol-solvated compound (Mizuguchi & Hino, 2005) and the cresol-solvated compound (Hino & Mizuguchi, 2005). For related literature, see: Herbst & Hunger (1993); Mizuguchi et al. (2006).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).
C28H20N4O4 | F(000) = 496.00 |
Mr = 476.48 | Dx = 1.438 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2yn | Cell parameters from 8499 reflections |
a = 10.0900 (16) Å | θ = 3.6–68.2° |
b = 8.8239 (15) Å | µ = 0.81 mm−1 |
c = 12.846 (2) Å | T = 93 K |
β = 105.811 (10)° | Platelet, light brown |
V = 1100.5 (3) Å3 | 0.50 × 0.14 × 0.13 mm |
Z = 2 |
Rigaku R-AXIS RAPID diffractometer | 1751 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.021 |
ω scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −12→12 |
Tmin = 0.881, Tmax = 0.900 | k = −9→9 |
9001 measured reflections | l = −14→14 |
1909 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.2956P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.123 | (Δ/σ)max < 0.001 |
S = 0.94 | Δρmax = 0.20 e Å−3 |
1909 reflections | Δρmin = −0.28 e Å−3 |
164 parameters |
C28H20N4O4 | V = 1100.5 (3) Å3 |
Mr = 476.48 | Z = 2 |
Monoclinic, P21/n | Cu Kα radiation |
a = 10.0900 (16) Å | µ = 0.81 mm−1 |
b = 8.8239 (15) Å | T = 93 K |
c = 12.846 (2) Å | 0.50 × 0.14 × 0.13 mm |
β = 105.811 (10)° |
Rigaku R-AXIS RAPID diffractometer | 1909 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1751 reflections with F2 > 2σ(F2) |
Tmin = 0.881, Tmax = 0.900 | Rint = 0.021 |
9001 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 164 parameters |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.20 e Å−3 |
1909 reflections | Δρmin = −0.28 e Å−3 |
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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.63037 (9) | −0.03698 (11) | 0.08849 (7) | 0.0236 (2) | |
O2 | 0.82986 (10) | 0.41491 (11) | 0.05932 (8) | 0.0277 (2) | |
N1 | 0.72158 (10) | 0.18910 (13) | 0.05892 (8) | 0.0202 (3) | |
N2 | 0.33163 (12) | 0.66405 (15) | 0.21169 (9) | 0.0314 (3) | |
C1 | 0.72033 (12) | 0.03121 (16) | 0.06131 (9) | 0.0197 (3) | |
C2 | 0.83357 (12) | −0.04762 (16) | 0.02935 (9) | 0.0192 (3) | |
C3 | 0.83190 (13) | −0.20294 (15) | 0.01844 (10) | 0.0213 (3) | |
C4 | 0.94482 (12) | 0.03810 (16) | 0.01277 (9) | 0.0184 (3) | |
C5 | 0.94845 (13) | 0.19711 (16) | 0.02271 (9) | 0.0203 (3) | |
C6 | 1.05903 (13) | 0.27826 (16) | 0.00833 (10) | 0.0222 (3) | |
C7 | 0.83207 (13) | 0.27835 (16) | 0.04804 (10) | 0.0212 (3) | |
C8 | 0.60316 (13) | 0.27091 (16) | 0.07764 (10) | 0.0221 (3) | |
C9 | 0.62031 (13) | 0.30750 (16) | 0.19715 (10) | 0.0243 (3) | |
C10 | 0.51955 (13) | 0.43001 (15) | 0.20583 (9) | 0.0204 (3) | |
C11 | 0.39203 (14) | 0.39920 (16) | 0.22266 (11) | 0.0261 (3) | |
C12 | 0.30364 (14) | 0.51844 (18) | 0.22457 (11) | 0.0304 (3) | |
C13 | 0.45555 (14) | 0.69295 (16) | 0.19616 (10) | 0.0274 (3) | |
C14 | 0.55050 (13) | 0.58128 (16) | 0.19223 (10) | 0.0240 (3) | |
H3 | 0.7566 | −0.2596 | 0.0291 | 0.026* | |
H6 | 1.0615 | 0.3853 | 0.0165 | 0.027* | |
H8a | 0.5192 | 0.2088 | 0.0503 | 0.027* | |
H8b | 0.5900 | 0.3667 | 0.0359 | 0.027* | |
H9a | 0.6032 | 0.2154 | 0.2356 | 0.029* | |
H9b | 0.7156 | 0.3421 | 0.2312 | 0.029* | |
H11 | 0.3659 | 0.2980 | 0.2327 | 0.031* | |
H12 | 0.2167 | 0.4950 | 0.2359 | 0.037* | |
H13 | 0.4793 | 0.7954 | 0.1874 | 0.033* | |
H14 | 0.6364 | 0.6078 | 0.1803 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0208 (4) | 0.0240 (5) | 0.0273 (5) | −0.0029 (3) | 0.0088 (3) | 0.0010 (3) |
O2 | 0.0318 (5) | 0.0175 (6) | 0.0382 (5) | 0.0008 (3) | 0.0170 (4) | −0.0012 (3) |
N1 | 0.0212 (5) | 0.0191 (7) | 0.0210 (5) | 0.0009 (4) | 0.0073 (4) | −0.0010 (4) |
N2 | 0.0288 (6) | 0.0363 (8) | 0.0291 (6) | 0.0069 (5) | 0.0079 (4) | −0.0041 (5) |
C1 | 0.0202 (6) | 0.0213 (8) | 0.0166 (6) | −0.0007 (4) | 0.0032 (4) | 0.0001 (4) |
C2 | 0.0219 (6) | 0.0184 (7) | 0.0174 (6) | −0.0002 (4) | 0.0053 (4) | 0.0012 (4) |
C3 | 0.0218 (6) | 0.0207 (7) | 0.0225 (6) | −0.0027 (4) | 0.0079 (4) | 0.0014 (5) |
C4 | 0.0227 (6) | 0.0172 (7) | 0.0156 (6) | −0.0009 (4) | 0.0055 (4) | 0.0010 (4) |
C5 | 0.0237 (6) | 0.0190 (8) | 0.0187 (6) | 0.0003 (4) | 0.0067 (5) | 0.0007 (4) |
C6 | 0.0267 (6) | 0.0158 (7) | 0.0249 (6) | −0.0011 (4) | 0.0086 (5) | −0.0002 (5) |
C7 | 0.0267 (7) | 0.0173 (8) | 0.0205 (6) | 0.0004 (4) | 0.0078 (5) | 0.0007 (4) |
C8 | 0.0212 (6) | 0.0217 (7) | 0.0240 (6) | 0.0021 (4) | 0.0071 (4) | −0.0008 (5) |
C9 | 0.0250 (6) | 0.0249 (8) | 0.0232 (6) | 0.0026 (5) | 0.0070 (5) | −0.0006 (5) |
C10 | 0.0220 (6) | 0.0245 (7) | 0.0149 (5) | 0.0011 (4) | 0.0055 (4) | −0.0025 (4) |
C11 | 0.0261 (7) | 0.0286 (8) | 0.0252 (6) | −0.0043 (5) | 0.0097 (5) | −0.0034 (5) |
C12 | 0.0222 (6) | 0.0407 (9) | 0.0300 (7) | −0.0016 (5) | 0.0096 (5) | −0.0053 (6) |
C13 | 0.0337 (7) | 0.0253 (8) | 0.0230 (6) | 0.0001 (5) | 0.0074 (5) | −0.0025 (5) |
C14 | 0.0226 (6) | 0.0298 (8) | 0.0204 (6) | −0.0024 (5) | 0.0070 (5) | −0.0026 (5) |
O1—C1 | 1.2168 (16) | C6—H6 | 0.950 |
O2—C7 | 1.2146 (17) | C8—H8a | 0.990 |
N1—C1 | 1.3937 (18) | C8—H8b | 0.990 |
N1—C7 | 1.4027 (17) | C9—C10 | 1.5088 (19) |
N2—C12 | 1.335 (2) | C9—H9a | 0.990 |
N2—C13 | 1.3432 (19) | C9—H9b | 0.990 |
C1—C2 | 1.4878 (18) | C10—C11 | 1.388 (2) |
C2—C3 | 1.3773 (19) | C10—C14 | 1.3926 (19) |
C2—C4 | 1.4170 (18) | C11—C12 | 1.384 (2) |
C3—C6i | 1.406 (2) | C11—H11 | 0.950 |
C3—H3 | 0.950 | C12—H12 | 0.950 |
C4—C4i | 1.4138 (18) | C13—C14 | 1.385 (2) |
C4—C5 | 1.4085 (19) | C13—H13 | 0.950 |
C5—C6 | 1.3799 (19) | C14—H14 | 0.950 |
C5—C7 | 1.4856 (19) | ||
O1···O1ii | 3.0425 (11) | C14···C1viii | 3.4024 (15) |
O1···C1ii | 3.5379 (13) | C14···H8av | 3.526 |
O1···C8ii | 3.4099 (14) | C14···H8bv | 2.923 |
O1···C9iii | 3.4669 (14) | C14···H9aviii | 3.564 |
O1···C13iv | 3.4688 (17) | C14···H9bviii | 3.251 |
O1···H8aii | 2.507 | H3···O2iv | 2.965 |
O1···H9biii | 2.637 | H3···C8ii | 3.515 |
O1···H13iv | 2.680 | H3···C9iii | 3.447 |
O1···H14iv | 3.344 | H3···C11ii | 3.403 |
O1···H14iii | 3.490 | H3···H8aii | 2.727 |
O2···N2v | 3.4884 (14) | H3···H8bii | 3.497 |
O2···C3vi | 3.4136 (16) | H3···H9aiii | 2.977 |
O2···C6vii | 3.1422 (17) | H3···H9biii | 3.146 |
O2···C12v | 3.5753 (16) | H3···H11ii | 3.269 |
O2···H3vi | 2.965 | H3···H14iv | 2.810 |
O2···H6vii | 2.417 | H6···O2vii | 2.417 |
O2···H13iii | 3.463 | H6···C6vii | 3.191 |
N1···C13v | 3.4385 (15) | H6···C7vii | 3.337 |
N1···C14iii | 3.5223 (14) | H6···C12xi | 3.307 |
N1···H13v | 3.263 | H6···H6vii | 2.352 |
N1···H14iii | 3.343 | H6···H12xi | 2.987 |
N2···O2v | 3.4884 (14) | H8a···O1ii | 2.507 |
N2···C5viii | 3.5389 (14) | H8a···C1ii | 3.239 |
N2···C7v | 3.3340 (15) | H8a···C3ii | 3.410 |
N2···C11ix | 3.339 (2) | H8a···C13v | 3.358 |
N2···C12ix | 3.595 (2) | H8a···C14v | 3.526 |
N2···H8bv | 3.490 | H8a···H3ii | 2.727 |
N2···H11ix | 2.580 | H8a···H13v | 3.057 |
N2···H12ix | 3.066 | H8a···H14v | 3.365 |
C1···O1ii | 3.5379 (13) | H8b···N2v | 3.490 |
C1···C10iii | 3.5150 (14) | H8b···C10v | 3.495 |
C1···C14iii | 3.4024 (15) | H8b···C13v | 2.937 |
C1···H8aii | 3.239 | H8b···C14v | 2.923 |
C1···H9biii | 3.060 | H8b···H3ii | 3.497 |
C1···H14iii | 3.309 | H8b···H8bv | 2.963 |
C2···C10iii | 3.3257 (15) | H8b···H13v | 3.110 |
C2···H9aiii | 3.585 | H8b···H14v | 3.087 |
C2···H9biii | 3.389 | H9a···C2viii | 3.585 |
C3···O2iv | 3.4136 (16) | H9a···C3viii | 3.132 |
C3···C9iii | 3.5537 (18) | H9a···C14iii | 3.564 |
C3···H8aii | 3.410 | H9a···H3viii | 2.977 |
C3···H9aiii | 3.132 | H9a···H14iii | 2.725 |
C3···H9biii | 3.401 | H9b···O1viii | 2.637 |
C3···H11ii | 3.404 | H9b···C1viii | 3.060 |
C4···C11iii | 3.5657 (17) | H9b···C2viii | 3.389 |
C5···N2iii | 3.5389 (14) | H9b···C3viii | 3.401 |
C5···C13iii | 3.4749 (16) | H9b···C13iii | 3.453 |
C5···H11x | 3.589 | H9b···C14iii | 3.251 |
C6···O2vii | 3.1422 (17) | H9b···H3viii | 3.146 |
C6···H6vii | 3.191 | H9b···H13iii | 2.997 |
C6···H12xi | 3.492 | H9b···H14iii | 2.622 |
C7···N2v | 3.3340 (15) | H11···N2xii | 2.580 |
C7···C13iii | 3.4814 (16) | H11···C3ii | 3.404 |
C7···H6vii | 3.337 | H11···C5xiv | 3.589 |
C7···H13iii | 3.416 | H11···C12xii | 3.134 |
C8···O1ii | 3.4099 (14) | H11···H3ii | 3.269 |
C8···C13v | 3.4187 (18) | H11···H12xii | 2.862 |
C8···H3ii | 3.515 | H12···N2xii | 3.066 |
C8···H13v | 3.329 | H12···C6xiii | 3.492 |
C9···O1viii | 3.4669 (14) | H12···C13xii | 3.423 |
C9···C3viii | 3.5537 (18) | H12···H6xiii | 2.987 |
C9···H3viii | 3.447 | H12···H11ix | 2.862 |
C9···H14iii | 3.083 | H12···H13xii | 3.008 |
C10···C1viii | 3.5150 (14) | H13···O1vi | 2.680 |
C10···C2viii | 3.3257 (15) | H13···O2viii | 3.463 |
C10···H8bv | 3.495 | H13···N1v | 3.263 |
C11···N2xii | 3.339 (2) | H13···C7viii | 3.416 |
C11···C4viii | 3.5657 (17) | H13···C8v | 3.329 |
C11···H3ii | 3.403 | H13···H8av | 3.057 |
C12···O2v | 3.5753 (16) | H13···H8bv | 3.110 |
C12···N2xii | 3.595 (2) | H13···H9bviii | 2.997 |
C12···H6xiii | 3.307 | H13···H12ix | 3.008 |
C12···H11ix | 3.134 | H14···O1vi | 3.344 |
C13···O1vi | 3.4688 (17) | H14···O1viii | 3.490 |
C13···N1v | 3.4385 (15) | H14···N1viii | 3.343 |
C13···C5viii | 3.4749 (16) | H14···C1viii | 3.309 |
C13···C7viii | 3.4814 (16) | H14···C9viii | 3.083 |
C13···C8v | 3.4187 (18) | H14···H3vi | 2.810 |
C13···H8av | 3.358 | H14···H8av | 3.365 |
C13···H8bv | 2.937 | H14···H8bv | 3.087 |
C13···H9bviii | 3.453 | H14···H9aviii | 2.725 |
C13···H12ix | 3.423 | H14···H9bviii | 2.622 |
C14···N1viii | 3.5223 (14) | ||
C1—N1—C7 | 125.15 (11) | N1—C8—H8a | 109.0 |
C1—N1—C8 | 118.32 (10) | N1—C8—H8b | 109.0 |
C7—N1—C8 | 116.35 (11) | C9—C8—H8a | 109.0 |
C12—N2—C13 | 115.97 (12) | C9—C8—H8b | 109.0 |
O1—C1—N1 | 120.84 (12) | H8a—C8—H8b | 107.8 |
O1—C1—C2 | 122.48 (12) | C8—C9—C10 | 109.31 (9) |
N1—C1—C2 | 116.68 (11) | C8—C9—H9a | 109.8 |
C1—C2—C3 | 120.28 (12) | C8—C9—H9b | 109.8 |
C1—C2—C4 | 119.43 (12) | C10—C9—H9a | 109.8 |
C3—C2—C4 | 120.27 (12) | C10—C9—H9b | 109.8 |
C2—C3—C6i | 120.43 (12) | H9a—C9—H9b | 108.3 |
C2—C3—H3 | 119.8 | C9—C10—C11 | 122.88 (12) |
C6i—C3—H3 | 119.8 | C9—C10—C14 | 119.92 (12) |
C2—C4—C4i | 119.16 (12) | C11—C10—C14 | 117.14 (12) |
C2—C4—C5 | 121.35 (12) | C10—C11—C12 | 118.88 (13) |
C4i—C4—C5 | 119.48 (12) | C10—C11—H11 | 120.6 |
C4—C5—C6 | 120.45 (12) | C12—C11—H11 | 120.6 |
C4—C5—C7 | 119.87 (12) | N2—C12—C11 | 124.77 (14) |
C6—C5—C7 | 119.68 (12) | N2—C12—H12 | 117.6 |
C3i—C6—C5 | 120.18 (12) | C11—C12—H12 | 117.6 |
C3i—C6—H6 | 119.9 | N2—C13—C14 | 123.48 (13) |
C5—C6—H6 | 119.9 | N2—C13—H13 | 118.3 |
O2—C7—N1 | 120.28 (12) | C14—C13—H13 | 118.3 |
O2—C7—C5 | 123.10 (12) | C10—C14—C13 | 119.76 (12) |
N1—C7—C5 | 116.62 (11) | C10—C14—H14 | 120.1 |
N1—C8—C9 | 113.10 (9) | C13—C14—H14 | 120.1 |
C1—N1—C7—O2 | −171.45 (10) | C2—C3—C6i—C5i | 0.74 (17) |
C1—N1—C7—C5 | 8.47 (16) | C2—C4—C4i—C5i | 0.88 (15) |
C7—N1—C1—O1 | 167.88 (10) | C2—C4—C5—C6 | 178.72 (10) |
C7—N1—C1—C2 | −12.06 (15) | C2—C4—C5—C7 | −1.74 (15) |
C1—N1—C8—C9 | 90.12 (12) | C4i—C4—C5—C6 | −0.38 (15) |
C8—N1—C1—O1 | −7.03 (15) | C4i—C4—C5—C7 | 179.16 (9) |
C8—N1—C1—C2 | 173.03 (9) | C5—C4—C4i—C2i | −0.88 (15) |
C7—N1—C8—C9 | −85.24 (13) | C4—C5—C6—C3i | 1.20 (16) |
C8—N1—C7—O2 | 3.55 (16) | C4—C5—C7—O2 | 178.82 (11) |
C8—N1—C7—C5 | −176.52 (9) | C4—C5—C7—N1 | −1.10 (15) |
C12—N2—C13—C14 | 0.61 (17) | C6—C5—C7—O2 | −1.63 (17) |
C13—N2—C12—C11 | −0.15 (19) | C6—C5—C7—N1 | 178.44 (10) |
O1—C1—C2—C3 | 6.97 (16) | C7—C5—C6—C3i | −178.35 (10) |
O1—C1—C2—C4 | −171.52 (10) | N1—C8—C9—C10 | 162.48 (11) |
N1—C1—C2—C3 | −173.10 (9) | C8—C9—C10—C11 | 95.71 (14) |
N1—C1—C2—C4 | 8.41 (14) | C8—C9—C10—C14 | −81.51 (13) |
C1—C2—C3—C6i | −177.93 (10) | C9—C10—C11—C12 | −177.04 (11) |
C1—C2—C4—C5 | −1.96 (15) | C9—C10—C14—C13 | 177.55 (10) |
C1—C2—C4—C4i | 177.15 (9) | C11—C10—C14—C13 | 0.17 (16) |
C3—C2—C4—C5 | 179.55 (10) | C14—C10—C11—C12 | 0.25 (17) |
C3—C2—C4—C4i | −1.34 (15) | C10—C11—C12—N2 | −0.3 (2) |
C4—C2—C3—C6i | 0.54 (16) | N2—C13—C14—C10 | −0.64 (18) |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x, y−1, z; (v) −x+1, −y+1, −z; (vi) x, y+1, z; (vii) −x+2, −y+1, −z; (viii) −x+3/2, y+1/2, −z+1/2; (ix) −x+1/2, y+1/2, −z+1/2; (x) x+1/2, −y+1/2, z−1/2; (xi) x+1, y, z; (xii) −x+1/2, y−1/2, −z+1/2; (xiii) x−1, y, z; (xiv) x−1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C28H20N4O4 |
Mr | 476.48 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 93 |
a, b, c (Å) | 10.0900 (16), 8.8239 (15), 12.846 (2) |
β (°) | 105.811 (10) |
V (Å3) | 1100.5 (3) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.81 |
Crystal size (mm) | 0.50 × 0.14 × 0.13 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.881, 0.900 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 9001, 1909, 1751 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.123, 0.94 |
No. of reflections | 1909 |
No. of parameters | 164 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.28 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2006), SIR2004 (Burla et al., 2003), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996).
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The title compound (PyENI) is an organic pigment which belongs to the category of perylene and perinone pigments (Herbst & Hunger, 1993). The perylene and perinone pigments differ in the central skeleton being perylene or naphthalene, respectively. We were previously involved in the study of the crystal and electronic structures of pyridylethylnaphthaleneimide (PyEPI) (Mizuguchi et al., 2006). In PyEPI there are two structural isomers in the solid state: the cis form (two pyridylethylgroups are on the same side as characterized by vivid red color; Tojo & Mizuguchi, 2002) and the trans form (across the perylene skeleton as characterized by black color; Mizuguchi & Hino, 2005; Hino & Mizuguchi, 2005). Surprising to say, the trans form (black) is found to be easily transformed into the cis one (red) by heating above 373 K for several s. This phase transformation has prompted us to investigate the crystal structure of PyENI in order to study whether the similar phenomenon occurrs at the shorter wavelengths.
The title molecule is centrosymmetric (Fig. 1) and an asymmetric unit comprises a half of the molecule. Therefore, pyridylethyl groups are arranged in a trans fashion across the naphthaleneimide skeleton. The pyridyl rings and naphthaleneimide skeleton are twisted by 9.45 (5)°. The crystal packing of (I) (Fig. 2) is dominated by van der Waals interactions. The present molecular arrangement of PyENI contrasts remarkably with that of PyEPI where the molecules are involved in π ···π interactions with separation distance of about 3.3 - 3.5 Å.