The title compound, C34H16N4O4, is a perylene-imide pigment utilized for H2 gas sensors. The molecule has Ci symmetry with one half-molecule in the asymmetric unit. The angle between each of the pyridyl rings and the perylene-imide skeleton is 54.88 (10)°. The molecules are stacked in a `hunter's fence' fashion (viz. when viewed from the side, molecules, slipped by 45° within molecular stacks, cross each other in a fence-like structure) along the b axis.
Supporting information
CCDC reference: 264075
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.073
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
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 0.00
From the CIF: _reflns_number_total 1922
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2038
Completeness (_total/calc) 94.31%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C5 -C7_a 1.44 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 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
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.
Crystal data top
C34H16N4O4 | F(000) = 560.0 |
Mr = 544.51 | Dx = 1.633 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2yn | Cell parameters from 6312 reflections |
a = 15.422 (2) Å | θ = 3.2–65.5° |
b = 3.8275 (6) Å | µ = 0.90 mm−1 |
c = 19.282 (3) Å | T = 93 K |
β = 103.29 (1)° | Platelet, red |
V = 1107.7 (3) Å3 | 0.50 × 0.07 × 0.03 mm |
Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID Imaging Plate diffractometer | 1009 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.048 |
48 frames, δ ω = 15° scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −18→18 |
Tmin = 0.973, Tmax = 0.973 | k = −4→4 |
10013 measured reflections | l = −23→23 |
1922 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + {0.025[Max(Fo2,0) + 2Fc2]/3}2] |
wR(F2) = 0.073 | (Δ/σ)max = 0.0004 |
S = 0.94 | Δρmax = 0.23 e Å−3 |
1922 reflections | Δρmin = −0.25 e Å−3 |
190 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > -10.0 σ(F2). 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 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.8306 (1) | −0.1188 (5) | 0.19907 (9) | 0.0227 (6) | |
O2 | 0.8985 (1) | 0.4268 (5) | 0.00748 (8) | 0.0207 (6) | |
N1 | 0.8666 (1) | 0.1795 (6) | 0.1066 (1) | 0.0162 (6) | |
N2 | 1.0717 (1) | 0.2756 (6) | 0.2480 (1) | 0.0231 (7) | |
C1 | 0.8051 (2) | 0.0532 (8) | 0.1448 (1) | 0.0184 (8) | |
C2 | 0.7105 (2) | 0.1410 (8) | 0.1162 (1) | 0.0160 (8) | |
C3 | 0.6489 (2) | 0.0433 (8) | 0.1544 (1) | 0.0181 (8) | |
C4 | 0.5593 (2) | 0.1306 (7) | 0.1293 (1) | 0.0178 (8) | |
C5 | 0.5292 (2) | 0.3160 (7) | 0.0669 (1) | 0.0160 (7) | |
C6 | 0.5920 (2) | 0.4077 (8) | 0.0256 (1) | 0.0155 (7) | |
C7 | 0.5650 (2) | 0.5867 (7) | −0.0411 (1) | 0.0142 (8) | |
C8 | 0.6289 (2) | 0.6650 (8) | −0.0794 (1) | 0.0176 (7) | |
C9 | 0.7182 (2) | 0.5800 (7) | −0.0530 (1) | 0.0175 (8) | |
C10 | 0.7463 (2) | 0.4150 (7) | 0.0118 (1) | 0.0153 (8) | |
C11 | 0.8422 (2) | 0.3444 (8) | 0.0395 (1) | 0.0170 (8) | |
C12 | 0.6832 (2) | 0.3230 (8) | 0.0515 (1) | 0.0146 (8) | |
C13 | 1.1304 (2) | 0.1119 (7) | 0.2173 (1) | 0.0227 (8) | |
C14 | 1.1093 (2) | −0.0284 (8) | 0.1494 (1) | 0.0199 (8) | |
C15 | 1.0214 (2) | −0.0139 (8) | 0.1102 (1) | 0.0194 (8) | |
C16 | 0.9602 (2) | 0.1500 (8) | 0.1412 (1) | 0.0174 (8) | |
C17 | 0.9882 (2) | 0.2935 (8) | 0.2090 (1) | 0.0198 (8) | |
H1 | 0.6675 | −0.0830 | 0.1977 | 0.0217* | |
H2 | 0.5176 | 0.0603 | 0.1560 | 0.0214* | |
H3 | 0.6113 | 0.7783 | −0.1243 | 0.0211* | |
H4 | 0.7605 | 0.6366 | −0.0802 | 0.0210* | |
H5 | 1.1902 | 0.0915 | 0.2439 | 0.0272* | |
H6 | 1.1542 | −0.1332 | 0.1298 | 0.0239* | |
H7 | 1.0043 | −0.1131 | 0.0639 | 0.0233* | |
H8 | 0.9453 | 0.4115 | 0.2287 | 0.0237* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.019 (1) | 0.032 (1) | 0.0174 (10) | 0.006 (1) | 0.0052 (8) | 0.008 (1) |
O2 | 0.017 (1) | 0.029 (1) | 0.0170 (10) | −0.0000 (9) | 0.0055 (8) | 0.002 (1) |
N1 | 0.013 (1) | 0.022 (1) | 0.013 (1) | 0.003 (1) | 0.0018 (9) | −0.000 (1) |
N2 | 0.019 (1) | 0.030 (2) | 0.019 (1) | −0.000 (1) | 0.002 (1) | −0.000 (1) |
C1 | 0.021 (2) | 0.022 (2) | 0.013 (1) | 0.002 (1) | 0.005 (1) | −0.002 (1) |
C2 | 0.016 (1) | 0.018 (2) | 0.014 (1) | 0.001 (1) | 0.004 (1) | −0.004 (1) |
C3 | 0.024 (2) | 0.019 (2) | 0.011 (1) | 0.003 (1) | 0.004 (1) | −0.001 (1) |
C4 | 0.020 (2) | 0.021 (2) | 0.013 (1) | −0.001 (1) | 0.006 (1) | −0.001 (1) |
C5 | 0.014 (1) | 0.021 (2) | 0.013 (1) | −0.001 (1) | 0.003 (1) | −0.005 (1) |
C6 | 0.018 (1) | 0.017 (2) | 0.012 (1) | −0.001 (1) | 0.003 (1) | −0.002 (1) |
C7 | 0.014 (1) | 0.015 (2) | 0.012 (1) | −0.000 (1) | 0.002 (1) | −0.004 (1) |
C8 | 0.019 (1) | 0.020 (2) | 0.014 (1) | 0.000 (1) | 0.003 (1) | −0.001 (1) |
C9 | 0.019 (1) | 0.019 (2) | 0.015 (1) | −0.002 (1) | 0.005 (1) | −0.003 (1) |
C10 | 0.015 (1) | 0.018 (2) | 0.012 (1) | −0.002 (1) | 0.002 (1) | −0.005 (1) |
C11 | 0.019 (1) | 0.016 (2) | 0.015 (1) | 0.002 (1) | 0.003 (1) | −0.001 (1) |
C12 | 0.016 (1) | 0.016 (2) | 0.011 (1) | −0.002 (1) | 0.002 (1) | −0.005 (1) |
C13 | 0.017 (2) | 0.025 (2) | 0.026 (2) | 0.000 (1) | 0.003 (1) | 0.006 (1) |
C14 | 0.018 (2) | 0.022 (2) | 0.022 (1) | 0.002 (1) | 0.010 (1) | 0.003 (1) |
C15 | 0.020 (2) | 0.022 (2) | 0.017 (1) | −0.001 (1) | 0.005 (1) | 0.002 (1) |
C16 | 0.018 (2) | 0.021 (2) | 0.012 (1) | −0.003 (1) | 0.002 (1) | 0.002 (1) |
C17 | 0.021 (2) | 0.021 (2) | 0.020 (1) | 0.003 (1) | 0.009 (1) | −0.000 (1) |
Geometric parameters (Å, º) top
O1—C1 | 1.222 (3) | C6—C12 | 1.418 (3) |
O2—C11 | 1.218 (3) | C7—C8 | 1.394 (3) |
N1—C1 | 1.414 (3) | C8—C9 | 1.393 (3) |
N1—C11 | 1.411 (3) | C8—H3 | 0.95 |
N1—C16 | 1.448 (3) | C9—C10 | 1.379 (3) |
N2—C13 | 1.346 (3) | C9—H4 | 0.95 |
N2—C17 | 1.335 (3) | C10—C11 | 1.477 (3) |
C1—C2 | 1.475 (3) | C10—C12 | 1.413 (3) |
C2—C3 | 1.381 (3) | C13—C14 | 1.383 (3) |
C2—C12 | 1.407 (3) | C13—H5 | 0.95 |
C3—C4 | 1.396 (3) | C14—C15 | 1.393 (3) |
C3—H1 | 0.95 | C14—H6 | 0.95 |
C4—C5 | 1.383 (3) | C15—C16 | 1.379 (3) |
C4—H2 | 0.95 | C15—H7 | 0.95 |
C5—C6 | 1.433 (3) | C16—C17 | 1.392 (3) |
C5—C7i | 1.470 (3) | C17—H8 | 0.95 |
C6—C7 | 1.431 (3) | | |
| | | |
O1···C3ii | 3.057 (3) | C2···C6iii | 3.578 (4) |
O1···C17iii | 3.284 (3) | C3···C6iii | 3.444 (4) |
O1···C1iii | 3.332 (4) | C3···C12iii | 3.508 (4) |
O1···N1iii | 3.340 (3) | C3···C5iii | 3.546 (4) |
O1···C4ii | 3.488 (3) | C4···C5iii | 3.336 (4) |
O1···C2iii | 3.557 (3) | C4···C6iii | 3.518 (4) |
O2···C15iv | 3.221 (3) | C4···C7vii | 3.551 (4) |
O2···C15v | 3.234 (3) | C5···C5vii | 3.500 (5) |
O2···O2vi | 3.258 (3) | C5···C6vii | 3.579 (4) |
O2···C14v | 3.365 (3) | C6···C7iii | 3.384 (4) |
O2···N1iv | 3.554 (3) | C7···C12iv | 3.599 (4) |
N1···C11iii | 3.436 (4) | C8···C12iv | 3.527 (4) |
N1···C1iv | 3.598 (4) | C9···C10iv | 3.423 (4) |
N2···C14iv | 3.400 (4) | C9···C12iv | 3.597 (4) |
N2···C13iv | 3.415 (4) | C13···C14iv | 3.529 (4) |
C1···C10iii | 3.507 (4) | C14···C17iii | 3.540 (4) |
C1···C11iii | 3.513 (4) | C15···C17iii | 3.372 (4) |
C2···C12iii | 3.361 (4) | C15···C16iii | 3.428 (4) |
C2···C10iii | 3.548 (4) | C16···C17iii | 3.519 (4) |
| | | |
C1—N1—C11 | 124.1 (2) | C8—C9—C10 | 121.1 (2) |
C1—N1—C16 | 116.8 (2) | C8—C9—H4 | 119.1 |
C11—N1—C16 | 119.0 (2) | C10—C9—H4 | 119.8 |
C13—N2—C17 | 115.8 (2) | C9—C10—C11 | 119.4 (2) |
O1—C1—N1 | 120.5 (2) | C9—C10—C12 | 119.5 (2) |
O1—C1—C2 | 122.6 (2) | C11—C10—C12 | 121.0 (2) |
N1—C1—C2 | 116.9 (2) | O2—C11—N1 | 120.6 (2) |
C1—C2—C3 | 118.7 (2) | O2—C11—C10 | 122.7 (3) |
C1—C2—C12 | 120.9 (2) | N1—C11—C10 | 116.6 (2) |
C3—C2—C12 | 120.4 (2) | C2—C12—C6 | 119.8 (2) |
C2—C3—C4 | 119.9 (2) | C2—C12—C10 | 120.0 (3) |
C2—C3—H1 | 120.0 | C6—C12—C10 | 120.2 (2) |
C4—C3—H1 | 120.1 | N2—C13—C14 | 124.2 (2) |
C3—C4—C5 | 122.2 (2) | N2—C13—H5 | 117.9 |
C3—C4—H2 | 119.2 | C14—C13—H5 | 117.9 |
C5—C4—H2 | 118.6 | C13—C14—C15 | 119.1 (2) |
C4—C5—C6 | 118.4 (3) | C13—C14—H6 | 120.2 |
C4—C5—C7i | 122.2 (2) | C15—C14—H6 | 120.7 |
C6—C5—C7i | 119.4 (2) | C14—C15—C16 | 117.4 (2) |
C5—C6—C7 | 121.5 (2) | C14—C15—H7 | 121.7 |
C5—C6—C12 | 119.4 (3) | C16—C15—H7 | 120.9 |
C7—C6—C12 | 119.1 (2) | N1—C16—C15 | 123.0 (2) |
C5i—C7—C6 | 119.1 (2) | N1—C16—C17 | 117.6 (2) |
C5i—C7—C8 | 122.0 (2) | C15—C16—C17 | 119.4 (2) |
C6—C7—C8 | 118.9 (2) | N2—C17—C16 | 124.1 (2) |
C7—C8—C9 | 121.1 (2) | N2—C17—H8 | 117.4 |
C7—C8—H3 | 119.6 | C16—C17—H8 | 118.5 |
C9—C8—H3 | 119.3 | | |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x, y−1, z; (iv) x, y+1, z; (v) −x+2, −y, −z; (vi) −x+2, −y+1, −z; (vii) −x+1, −y, −z. |