The title compound, C38H24N4O4·2C7H8O, is a 1:2 complex of a pyridylethylperylene derivative, EPY, with m-cresol. The EPY molecule has a centre of symmetry and the pyridylethyl groups are attached to the perylene-imide skeleton in a trans fashion. The EPY molecules are stacked along the a axis with a slip angle of about 47°.
Supporting information
CCDC reference: 269837
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.008 Å
- R factor = 0.100
- wR factor = 0.118
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: A two-dimentional detector (IP) was used in combinaiton with Cu as
radiation.
|
Alert level B
DIFMN02_ALERT_2_B The minimum difference density is < -0.1*ZMAX*1.00
_refine_diff_density_min given = -0.900
Test value = -0.800
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 1.080
Test value = 0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 1.08 e/A 3
PLAT098_ALERT_2_B Minimum (Negative) Residual Density ............ -0.90 e/A 3
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.618 0.930
Tmin' and Tmax expected: 0.739 0.930
RR' = 0.836
Please check that your absorption correction is appropriate.
DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75
The relevant atom site should be identified.
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range
for the supplied radiation type. Expected range 1.54175-1.54180
Wavelength given = 1.54190
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 68.20
From the CIF: _diffrn_reflns_theta_full 68.20
From the CIF: _reflns_number_total 3363
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3613
Completeness (_total/calc) 93.08%
RFACG01_ALERT_3_C The value of the R factor is > 0.10
R factor given 0.100
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.147
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C10 -C12_a 1.45 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C7 H8 O
1 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
10 ALERT type 3 Indicator that the structure quality may be low
1 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: SYSTEM90 (Hou et al., 1994); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.
Crystal data top
C38H24N4O4·2C7H8O | F(000) = 856.0 |
Mr = 816.88 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5419 Å |
Hall symbol: -P 2ybc | Cell parameters from 4038 reflections |
a = 4.903 (6) Å | θ = 3.0–65.6° |
b = 29.26 (4) Å | µ = 0.73 mm−1 |
c = 13.96 (2) Å | T = 93 K |
β = 97.65 (6)° | Needle, red |
V = 1985 (4) Å3 | 0.40 × 0.10 × 0.10 mm |
Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID imaging plate diffractometer | 1335 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.147 |
24 frames, δ ω = 30° scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = 0→5 |
Tmin = 0.618, Tmax = 0.930 | k = 0→35 |
3443 measured reflections | l = −16→16 |
3363 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.100 | w = 1/[σ2(Fo2) + {0.025[Max(Fo2,0) + 2Fc2]/3}2] |
wR(F2) = 0.118 | (Δ/σ)max = 0.0002 |
S = 1.00 | Δρmax = 1.08 e Å−3 |
3363 reflections | Δρmin = −0.90 e Å−3 |
280 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > -3.0 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 | −0.2431 (7) | 0.6434 (1) | 0.7752 (3) | 0.036 (1) | |
O2 | −0.5191 (7) | 0.4996 (1) | 0.6876 (3) | 0.036 (1) | |
O3 | −1.5941 (7) | 0.6440 (1) | 0.1952 (2) | 0.037 (1) | |
N1 | −1.1697 (9) | 0.6368 (2) | 0.3457 (3) | 0.033 (2) | |
N2 | −0.3847 (9) | 0.5714 (1) | 0.7349 (3) | 0.024 (2) | |
C1 | −0.992 (1) | 0.6661 (2) | 0.3919 (4) | 0.037 (2) | |
C2 | −0.777 (1) | 0.6536 (2) | 0.4621 (4) | 0.033 (2) | |
C3 | −0.730 (1) | 0.6081 (2) | 0.4846 (4) | 0.027 (2) | |
C4 | −0.501 (1) | 0.5930 (2) | 0.5611 (4) | 0.038 (2) | |
C5 | −0.607 (1) | 0.5898 (2) | 0.6613 (4) | 0.032 (2) | |
C6 | −0.205 (1) | 0.6024 (2) | 0.7880 (4) | 0.032 (2) | |
C7 | 0.019 (1) | 0.5836 (2) | 0.8572 (4) | 0.023 (2) | |
C8 | 0.199 (1) | 0.6124 (2) | 0.9109 (4) | 0.024 (2) | |
C9 | 0.4173 (10) | 0.5956 (2) | 0.9777 (4) | 0.021 (2) | |
C10 | 0.459 (1) | 0.5491 (2) | 0.9903 (4) | 0.023 (2) | |
C11 | 0.275 (1) | 0.5185 (2) | 0.9328 (4) | 0.020 (2) | |
C12 | 0.312 (1) | 0.4701 (2) | 0.9415 (4) | 0.022 (2) | |
C13 | 0.128 (1) | 0.4422 (2) | 0.8824 (4) | 0.022 (2) | |
C14 | −0.090 (1) | 0.4598 (2) | 0.8189 (4) | 0.027 (2) | |
C15 | −0.127 (1) | 0.5067 (2) | 0.8100 (4) | 0.025 (2) | |
C16 | −0.355 (1) | 0.5235 (2) | 0.7405 (4) | 0.032 (2) | |
C17 | −0.914 (1) | 0.5772 (2) | 0.4345 (4) | 0.028 (2) | |
C18 | −1.128 (1) | 0.5928 (2) | 0.3672 (4) | 0.032 (2) | |
C19 | 0.054 (1) | 0.5360 (2) | 0.8662 (4) | 0.023 (2) | |
C20 | −1.721 (1) | 0.6858 (2) | 0.1791 (4) | 0.025 (2) | |
C21 | −1.944 (1) | 0.6882 (2) | 0.1046 (4) | 0.025 (2) | |
C22 | −2.082 (1) | 0.7288 (2) | 0.0829 (4) | 0.026 (2) | |
C23 | −2.002 (1) | 0.7670 (2) | 0.1378 (4) | 0.035 (2) | |
C24 | −1.778 (1) | 0.7645 (2) | 0.2119 (4) | 0.038 (2) | |
C25 | −1.637 (1) | 0.7241 (2) | 0.2320 (4) | 0.041 (2) | |
C26 | −2.321 (1) | 0.7306 (2) | 0.0014 (4) | 0.041 (2) | |
H1 | −1.4375 | 0.6487 | 0.2475 | 0.0395* | |
H2 | −1.0141 | 0.6975 | 0.3762 | 0.0449* | |
H3 | −0.6623 | 0.6765 | 0.4949 | 0.0396* | |
H4 | −0.4366 | 0.5640 | 0.5440 | 0.0453* | |
H5 | −0.3560 | 0.6147 | 0.5645 | 0.0453* | |
H6 | −0.7616 | 0.5700 | 0.6564 | 0.0384* | |
H7 | −0.6585 | 0.6194 | 0.6804 | 0.0384* | |
H8 | 0.1754 | 0.6444 | 0.9035 | 0.0281* | |
H9 | 0.5384 | 0.6165 | 1.0141 | 0.0260* | |
H10 | 0.1522 | 0.4100 | 0.8858 | 0.0267* | |
H11 | −0.2142 | 0.4396 | 0.7818 | 0.0314* | |
H12 | −0.8942 | 0.5454 | 0.4472 | 0.0335* | |
H13 | −1.2494 | 0.5708 | 0.3345 | 0.0379* | |
H14 | −2.0019 | 0.6614 | 0.0692 | 0.0301* | |
H15 | −2.0974 | 0.7950 | 0.1251 | 0.0419* | |
H16 | −1.7229 | 0.7911 | 0.2486 | 0.0449* | |
H17 | −1.4842 | 0.7228 | 0.2815 | 0.0498* | |
H18 | −2.3522 | 0.7614 | −0.0182 | 0.0485* | |
H19 | −2.2751 | 0.7131 | −0.0517 | 0.0485* | |
H20 | −2.4799 | 0.7184 | 0.0232 | 0.0485* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.042 (3) | 0.030 (3) | 0.034 (3) | 0.006 (2) | −0.004 (2) | 0.003 (2) |
O2 | 0.030 (3) | 0.035 (3) | 0.038 (3) | −0.000 (2) | −0.006 (2) | 0.003 (2) |
O3 | 0.045 (3) | 0.034 (3) | 0.028 (3) | 0.007 (2) | −0.013 (2) | 0.003 (2) |
N1 | 0.033 (4) | 0.039 (3) | 0.025 (3) | 0.010 (3) | −0.002 (3) | 0.002 (3) |
N2 | 0.020 (3) | 0.026 (3) | 0.025 (3) | 0.007 (3) | −0.001 (2) | 0.002 (3) |
C1 | 0.049 (5) | 0.020 (4) | 0.043 (4) | 0.004 (3) | 0.010 (4) | 0.003 (3) |
C2 | 0.036 (4) | 0.026 (4) | 0.036 (4) | −0.003 (3) | −0.000 (3) | 0.005 (3) |
C3 | 0.019 (4) | 0.042 (4) | 0.020 (4) | 0.004 (3) | 0.005 (3) | 0.007 (3) |
C4 | 0.034 (4) | 0.051 (4) | 0.028 (4) | 0.001 (3) | 0.006 (3) | 0.008 (3) |
C5 | 0.029 (4) | 0.037 (4) | 0.031 (4) | 0.004 (3) | 0.007 (3) | 0.007 (3) |
C6 | 0.036 (5) | 0.023 (4) | 0.037 (5) | 0.008 (3) | 0.009 (4) | 0.009 (3) |
C7 | 0.028 (4) | 0.017 (4) | 0.025 (4) | −0.005 (3) | 0.004 (3) | 0.006 (3) |
C8 | 0.022 (4) | 0.020 (4) | 0.029 (4) | 0.007 (3) | 0.006 (3) | 0.003 (3) |
C9 | 0.016 (4) | 0.023 (4) | 0.025 (4) | −0.006 (3) | 0.004 (3) | −0.002 (3) |
C10 | 0.022 (4) | 0.026 (4) | 0.022 (4) | −0.003 (3) | 0.007 (3) | 0.007 (3) |
C11 | 0.016 (4) | 0.026 (4) | 0.019 (4) | 0.003 (3) | 0.010 (3) | −0.000 (3) |
C12 | 0.020 (4) | 0.024 (4) | 0.023 (4) | 0.003 (3) | 0.004 (3) | 0.003 (3) |
C13 | 0.028 (4) | 0.017 (3) | 0.023 (4) | −0.001 (3) | 0.005 (3) | 0.000 (3) |
C14 | 0.023 (4) | 0.034 (4) | 0.022 (4) | −0.005 (3) | 0.004 (3) | −0.003 (3) |
C15 | 0.030 (4) | 0.032 (4) | 0.013 (3) | 0.004 (3) | 0.001 (3) | 0.004 (3) |
C16 | 0.034 (5) | 0.037 (4) | 0.028 (4) | −0.006 (4) | 0.017 (3) | −0.002 (4) |
C17 | 0.028 (4) | 0.028 (4) | 0.028 (4) | 0.004 (3) | 0.005 (3) | −0.003 (3) |
C18 | 0.038 (5) | 0.033 (4) | 0.028 (4) | 0.004 (3) | 0.010 (3) | −0.003 (3) |
C19 | 0.022 (4) | 0.027 (4) | 0.019 (4) | −0.001 (3) | −0.000 (3) | −0.002 (3) |
C20 | 0.019 (4) | 0.031 (4) | 0.023 (4) | 0.003 (3) | −0.003 (3) | 0.005 (3) |
C21 | 0.028 (4) | 0.022 (3) | 0.024 (4) | −0.004 (3) | 0.004 (3) | −0.007 (3) |
C22 | 0.029 (4) | 0.024 (4) | 0.025 (4) | 0.005 (3) | 0.002 (3) | 0.003 (3) |
C23 | 0.042 (4) | 0.027 (4) | 0.036 (4) | 0.020 (4) | 0.002 (3) | 0.006 (3) |
C24 | 0.048 (5) | 0.029 (4) | 0.035 (4) | −0.003 (4) | −0.001 (3) | −0.009 (3) |
C25 | 0.057 (5) | 0.044 (4) | 0.020 (4) | −0.003 (4) | −0.006 (3) | −0.006 (3) |
C26 | 0.040 (4) | 0.039 (4) | 0.044 (4) | −0.001 (3) | 0.005 (3) | 0.009 (4) |
Geometric parameters (Å, º) top
O1—C6 | 1.223 (7) | C10—C12i | 1.485 (7) |
O2—C16 | 1.233 (7) | C11—C12 | 1.429 (8) |
O3—C20 | 1.378 (6) | C11—C19 | 1.425 (7) |
O3—H1 | 0.996 | C12—C13 | 1.402 (7) |
N1—C1 | 1.327 (7) | C13—C14 | 1.393 (7) |
N1—C18 | 1.333 (7) | C13—H10 | 0.951 |
N2—C5 | 1.493 (7) | C14—C15 | 1.387 (8) |
N2—C6 | 1.405 (7) | C14—H11 | 0.949 |
N2—C16 | 1.412 (7) | C15—C16 | 1.465 (8) |
C1—C2 | 1.390 (8) | C15—C19 | 1.399 (8) |
C1—H2 | 0.949 | C17—C18 | 1.387 (7) |
C2—C3 | 1.382 (8) | C17—H12 | 0.950 |
C2—H3 | 0.951 | C18—H13 | 0.950 |
C3—C4 | 1.507 (7) | C20—C21 | 1.404 (7) |
C3—C17 | 1.399 (7) | C20—C25 | 1.377 (8) |
C4—C5 | 1.558 (8) | C21—C22 | 1.380 (8) |
C4—H4 | 0.948 | C21—H14 | 0.950 |
C4—H5 | 0.950 | C22—C23 | 1.382 (8) |
C5—H6 | 0.950 | C22—C26 | 1.523 (7) |
C5—H7 | 0.951 | C23—C24 | 1.407 (7) |
C6—C7 | 1.469 (8) | C23—H15 | 0.950 |
C7—C8 | 1.370 (7) | C24—C25 | 1.379 (8) |
C7—C19 | 1.406 (8) | C24—H16 | 0.950 |
C8—C9 | 1.410 (7) | C25—H17 | 0.950 |
C8—H8 | 0.949 | C26—H18 | 0.949 |
C9—C10 | 1.384 (7) | C26—H19 | 0.952 |
C9—H9 | 0.950 | C26—H20 | 0.944 |
C10—C11 | 1.437 (7) | | |
| | | |
O1···C23ii | 3.543 (7) | C5···C7v | 3.496 (8) |
O2···C18iii | 3.246 (7) | C6···C9v | 3.434 (8) |
O3···N1 | 2.761 (5) | C6···C8v | 3.592 (9) |
O3···C9iv | 3.356 (6) | C10···C14vii | 3.420 (8) |
O3···C14iii | 3.401 (6) | C10···C13vii | 3.585 (9) |
O3···C18 | 3.431 (6) | C11···C16vi | 3.438 (9) |
N2···C7v | 3.595 (8) | C11···C12vii | 3.581 (9) |
C1···C25vi | 3.454 (9) | C12···C19vii | 3.428 (8) |
C1···C20vi | 3.460 (8) | C12···C14vi | 3.597 (9) |
C3···C18vi | 3.589 (9) | C14···C18viii | 3.318 (8) |
C4···C18vi | 3.463 (8) | | |
| | | |
C20—O3—H1 | 106.6 | C11—C12—C13 | 117.5 (4) |
C1—N1—C18 | 116.4 (4) | C12—C13—C14 | 122.7 (5) |
C5—N2—C6 | 118.6 (4) | C12—C13—H10 | 118.7 |
C5—N2—C16 | 117.1 (4) | C14—C13—H10 | 118.6 |
C6—N2—C16 | 124.0 (4) | C13—C14—C15 | 120.0 (5) |
N1—C1—C2 | 124.2 (5) | C13—C14—H11 | 120.0 |
N1—C1—H2 | 117.8 | C15—C14—H11 | 120.0 |
C2—C1—H2 | 118.0 | C14—C15—C16 | 118.0 (5) |
C1—C2—C3 | 120.1 (5) | C14—C15—C19 | 119.5 (5) |
C1—C2—H3 | 120.0 | C16—C15—C19 | 122.5 (5) |
C3—C2—H3 | 119.9 | O2—C16—N2 | 118.3 (5) |
C2—C3—C4 | 121.9 (5) | O2—C16—C15 | 125.9 (5) |
C2—C3—C17 | 115.6 (5) | N2—C16—C15 | 115.8 (5) |
C4—C3—C17 | 122.5 (5) | C3—C17—C18 | 120.5 (5) |
C3—C4—C5 | 110.5 (4) | C3—C17—H12 | 119.6 |
C3—C4—H4 | 109.0 | C18—C17—H12 | 119.9 |
C3—C4—H5 | 108.8 | N1—C18—C17 | 123.3 (5) |
C5—C4—H4 | 109.5 | N1—C18—H13 | 118.5 |
C5—C4—H5 | 109.4 | C17—C18—H13 | 118.2 |
H4—C4—H5 | 109.7 | C7—C19—C11 | 119.3 (5) |
N2—C5—C4 | 110.0 (4) | C7—C19—C15 | 119.7 (5) |
N2—C5—H6 | 109.5 | C11—C19—C15 | 121.0 (5) |
N2—C5—H7 | 109.4 | O3—C20—C21 | 117.1 (5) |
C4—C5—H6 | 109.3 | O3—C20—C25 | 122.6 (4) |
C4—C5—H7 | 109.3 | C21—C20—C25 | 120.3 (5) |
H6—C5—H7 | 109.4 | C20—C21—C22 | 121.0 (5) |
O1—C6—N2 | 118.9 (5) | C20—C21—H14 | 119.6 |
O1—C6—C7 | 123.4 (5) | C22—C21—H14 | 119.4 |
N2—C6—C7 | 117.7 (5) | C21—C22—C23 | 118.7 (5) |
C6—C7—C8 | 120.0 (5) | C21—C22—C26 | 120.0 (5) |
C6—C7—C19 | 120.2 (5) | C23—C22—C26 | 121.3 (5) |
C8—C7—C19 | 119.7 (5) | C22—C23—C24 | 120.1 (5) |
C7—C8—C9 | 121.8 (5) | C22—C23—H15 | 119.9 |
C7—C8—H8 | 119.1 | C24—C23—H15 | 120.0 |
C9—C8—H8 | 119.1 | C23—C24—C25 | 120.9 (5) |
C8—C9—C10 | 120.7 (4) | C23—C24—H16 | 119.4 |
C8—C9—H9 | 119.7 | C25—C24—H16 | 119.6 |
C10—C9—H9 | 119.6 | C20—C25—C24 | 118.9 (5) |
C9—C10—C11 | 118.2 (5) | C20—C25—H17 | 120.6 |
C9—C10—C12i | 122.6 (5) | C24—C25—H17 | 120.5 |
C11—C10—C12i | 119.1 (5) | C22—C26—H18 | 109.2 |
C10—C11—C12 | 120.4 (5) | C22—C26—H19 | 109.0 |
C10—C11—C19 | 120.3 (5) | C22—C26—H20 | 109.4 |
C12—C11—C19 | 119.3 (5) | H18—C26—H19 | 109.4 |
C10i—C12—C11 | 120.4 (4) | H18—C26—H20 | 110.1 |
C10i—C12—C13 | 122.1 (5) | H19—C26—H20 | 109.8 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+2, −y+3/2, z+1/2; (iii) −x−2, −y+1, −z+1; (iv) x−2, y, z−1; (v) x−1, y, z; (vi) x+1, y, z; (vii) −x, −y+1, −z+2; (viii) −x−1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H1···N1 | 1.00 | 1.80 | 2.761 (5) | 161 |