N,N'-Di-4-pyridyl­peryl­ene-3,4:9,10-bis­(dicarbox­imide)

The title compound, C₃₄H₁₆N₄O₄, is a peryl­ene-imide pigment utilized for H₂ gas sensors. The mol­ecule has C_i symmetry. The angle between each of the pyridyl rings and the perylene-imide skeleton is 74.5 (2)°. The mol­ecules are stacked along the c axis with a tilt angle of about 31.5° between adjacent molecules.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.074
• wR factor = 0.147
• Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.92

Author Response: A two-dimensional detector was used in combination with Cu as radiation.

Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.554     0.958
            Tmin' and Tmax expected:      0.803     0.958
            RR' =      0.690
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.69
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   C13     ..       7.62 su
PLAT734_ALERT_1_B Contact Calc    3.481(8), Rep  3.4810(10) ......       8.00 su-Rat
              C1   -C1      1.555   8.565
PLAT734_ALERT_1_B Contact Calc    3.481(8), Rep  3.4810(10) ......       8.00 su-Rat
              C1   -C1      1.555   8.564
PLAT734_ALERT_1_B Contact Calc    3.490(8), Rep  3.4900(10) ......       8.00 su-Rat
              C2   -C2      1.555   8.565
PLAT734_ALERT_1_B Contact Calc    3.490(8), Rep  3.4900(10) ......       8.00 su-Rat
              C2   -C2      1.555   8.564

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               1965
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2141
           Completeness (_total/calc)             91.78%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.92
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C5     -C7_a          1.44 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   1 ALERT level A = In general: serious problem
   7 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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.

(I)

Crystal data

C34H16N4O4	F(000) = 1120
Mr = 544.51	Dx = 1.547 Mg m^−3
Orthorhombic, Pccn	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 8331 reflections
a = 21.232 (2) Å	θ = 3.5–68.2°
b = 15.890 (2) Å	µ = 0.85 mm^−1
c = 6.9311 (8) Å	T = 93 K
V = 2338.4 (5) Å^3	Needle, red
Z = 4	0.25 × 0.05 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	839 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.077
48 frames, δ ω = 15° scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −24→23
Tmin = 0.554, Tmax = 0.958	k = −18→18
18572 measured reflections	l = −7→6
1965 independent reflections

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.074	w = 1/[σ^2(Fo^2)]
wR(F^2) = 0.148	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.36 e Å^−3
1965 reflections	Δρmin = −0.33 e Å^−3
190 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4639 (1)	0.7904 (2)	0.2065 (5)	0.035 (1)
O2	0.5207 (1)	0.5145 (2)	0.2382 (5)	0.034 (1)
N1	0.4921 (2)	0.6528 (2)	0.2221 (7)	0.027 (1)
N2	0.2958 (2)	0.6067 (3)	0.2477 (7)	0.030 (1)
C1	0.5064 (2)	0.7397 (3)	0.2136 (8)	0.026 (1)
C2	0.5729 (2)	0.7630 (3)	0.2187 (8)	0.023 (1)
C3	0.5889 (2)	0.8476 (3)	0.2215 (8)	0.026 (1)
C4	0.6515 (2)	0.8713 (3)	0.2222 (8)	0.025 (1)
C5	0.7009 (2)	0.8131 (3)	0.2206 (8)	0.024 (1)
C6	0.6850 (2)	0.7257 (3)	0.2194 (7)	0.021 (1)
C7	0.7325 (2)	0.6625 (3)	0.2179 (7)	0.022 (1)
C8	0.7137 (2)	0.5780 (3)	0.2159 (7)	0.026 (1)
C9	0.6503 (2)	0.5548 (3)	0.2189 (8)	0.025 (1)
C10	0.6039 (2)	0.6150 (3)	0.2220 (8)	0.027 (2)
C11	0.5373 (2)	0.5885 (3)	0.2274 (8)	0.026 (1)
C12	0.6204 (2)	0.7007 (3)	0.2174 (7)	0.022 (1)
C13	0.3255 (3)	0.6284 (4)	0.0835 (9)	0.042 (2)
C14	0.3881 (3)	0.6419 (4)	0.0658 (8)	0.039 (2)
C15	0.4258 (2)	0.6313 (3)	0.2268 (9)	0.026 (2)
C16	0.3980 (2)	0.6058 (3)	0.3984 (8)	0.032 (2)
C17	0.3330 (2)	0.5960 (4)	0.4005 (8)	0.037 (2)
H1	0.5568	0.8892	0.2230	0.0313*
H2	0.6614	0.9296	0.2238	0.0306*
H3	0.7450	0.5353	0.2122	0.0311*
H4	0.6392	0.4969	0.2189	0.0299*
H5	0.3004	0.6348	−0.0290	0.0505*
H6	0.4058	0.6583	−0.0543	0.0470*
H7	0.4226	0.5954	0.5104	0.0381*
H8	0.3138	0.5805	0.5191	0.0443*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.023 (2)	0.035 (2)	0.046 (2)	0.002 (2)	−0.001 (2)	−0.004 (2)
O2	0.024 (2)	0.025 (2)	0.054 (2)	−0.003 (2)	−0.003 (2)	−0.003 (2)
N1	0.019 (2)	0.020 (2)	0.041 (3)	−0.001 (2)	0.004 (2)	0.001 (2)
N2	0.024 (2)	0.033 (2)	0.033 (3)	−0.007 (2)	0.007 (2)	0.008 (3)
C1	0.024 (3)	0.026 (3)	0.028 (3)	0.002 (2)	0.000 (3)	−0.002 (3)
C2	0.017 (2)	0.024 (3)	0.027 (3)	−0.001 (2)	0.003 (3)	0.000 (3)
C3	0.021 (3)	0.027 (3)	0.031 (3)	0.006 (2)	−0.002 (3)	−0.003 (3)
C4	0.023 (3)	0.026 (3)	0.027 (3)	0.002 (2)	0.005 (3)	0.003 (3)
C5	0.021 (3)	0.019 (3)	0.032 (3)	−0.004 (2)	−0.003 (3)	−0.006 (3)
C6	0.023 (2)	0.019 (3)	0.021 (3)	0.002 (2)	0.005 (3)	−0.003 (2)
C7	0.016 (3)	0.023 (3)	0.028 (3)	−0.004 (2)	0.002 (3)	0.001 (3)
C8	0.025 (3)	0.023 (3)	0.030 (3)	0.001 (2)	−0.005 (3)	−0.004 (3)
C9	0.024 (3)	0.024 (3)	0.027 (3)	−0.007 (2)	−0.001 (3)	0.004 (3)
C10	0.016 (3)	0.030 (3)	0.034 (3)	0.000 (2)	−0.002 (3)	−0.001 (3)
C11	0.026 (3)	0.023 (3)	0.031 (3)	−0.002 (2)	−0.001 (3)	−0.003 (3)
C12	0.021 (3)	0.023 (3)	0.021 (3)	0.000 (2)	0.002 (2)	−0.001 (3)
C13	0.025 (3)	0.050 (4)	0.050 (4)	−0.011 (3)	−0.012 (3)	−0.004 (3)
C14	0.029 (4)	0.052 (4)	0.036 (4)	−0.011 (3)	−0.001 (3)	−0.002 (3)
C15	0.015 (3)	0.023 (3)	0.040 (4)	−0.002 (2)	0.002 (3)	−0.006 (3)
C16	0.023 (3)	0.037 (3)	0.035 (4)	−0.004 (3)	−0.000 (3)	0.007 (3)
C17	0.026 (3)	0.045 (4)	0.040 (4)	−0.005 (3)	−0.005 (3)	0.007 (3)

Geometric parameters (Å, º)

O1—C1	1.211 (5)	C6—C12	1.426 (6)
O2—C11	1.231 (5)	C7—C8	1.401 (6)
N1—C1	1.415 (6)	C8—C9	1.397 (6)
N1—C11	1.402 (5)	C8—H3	0.951
N1—C15	1.449 (5)	C9—C10	1.373 (6)
N2—C13	1.346 (6)	C9—H4	0.950
N2—C17	1.332 (6)	C10—C11	1.476 (6)
C1—C2	1.459 (6)	C10—C12	1.408 (6)
C2—C3	1.386 (6)	C13—C14	1.353 (7)
C2—C12	1.415 (6)	C13—H5	0.950
C3—C4	1.380 (6)	C14—C15	1.383 (7)
C3—H1	0.951	C14—H6	0.952
C4—C5	1.399 (6)	C15—C16	1.388 (7)
C4—H2	0.951	C16—C17	1.389 (7)
C5—C6	1.429 (6)	C16—H7	0.951
C5—C7^i	1.466 (6)	C17—H8	0.951
C6—C7	1.424 (5)
O1···C16^ii	3.039 (6)	C1···C1^iii	3.481 (1)
O1···C14^iii	3.154 (7)	C1···C1^ii	3.481 (1)
O2···O2^iv	3.448 (7)	C2···C2^iii	3.490 (1)
N2···C8^v	3.422 (6)	C2···C2^ii	3.490 (1)
N2···C13^vi	3.488 (6)
C1—N1—C11	124.4 (4)	C8—C9—C10	120.5 (4)
C1—N1—C15	116.1 (4)	C8—C9—H4	119.8
C11—N1—C15	119.5 (4)	C10—C9—H4	119.7
C13—N2—C17	115.3 (4)	C9—C10—C11	119.3 (4)
O1—C1—N1	119.4 (4)	C9—C10—C12	119.7 (4)
O1—C1—C2	123.5 (5)	C11—C10—C12	121.0 (4)
N1—C1—C2	117.1 (4)	O2—C11—N1	120.2 (4)
C1—C2—C3	119.0 (4)	O2—C11—C10	123.2 (4)
C1—C2—C12	120.8 (4)	N1—C11—C10	116.6 (4)
C3—C2—C12	120.2 (4)	C2—C12—C6	119.4 (4)
C2—C3—C4	120.1 (4)	C2—C12—C10	120.0 (4)
C2—C3—H1	120.0	C6—C12—C10	120.6 (4)
C4—C3—H1	119.9	N2—C13—C14	125.3 (5)
C3—C4—C5	122.7 (4)	N2—C13—H5	117.4
C3—C4—H2	118.6	C14—C13—H5	117.3
C5—C4—H2	118.7	C13—C14—C15	118.4 (5)
C4—C5—C6	117.7 (4)	C13—C14—H6	120.8
C4—C5—C7^i	123.2 (4)	C15—C14—H6	120.8
C6—C5—C7^i	119.0 (4)	N1—C15—C14	121.0 (5)
C5—C6—C7	121.2 (4)	N1—C15—C16	120.0 (5)
C5—C6—C12	119.8 (4)	C14—C15—C16	118.8 (4)
C7—C6—C12	119.0 (4)	C15—C16—C17	117.6 (5)
C5^i—C7—C6	119.8 (4)	C15—C16—H7	121.2
C5^i—C7—C8	121.9 (4)	C17—C16—H7	121.2
C6—C7—C8	118.3 (4)	N2—C17—C16	124.5 (5)
C7—C8—C9	121.9 (4)	N2—C17—H8	117.8
C7—C8—H3	119.1	C16—C17—H8	117.7
C9—C8—H3	119.0

Symmetry codes: (i) −x+3/2, −y+3/2, z; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z; (v) x−1/2, −y+1, −z+1/2; (vi) −x+1/2, y, z+1/2.