Dibenzimidazo­[2,1-a:2',1'-a']­anthra­[2,1,9-def:6,5,10-d'e'f']­diiso­quinoline-10,21-dione: trans form (I)

The title compound, C₃₆H₁₆N₄O₂, is the trans form of a benz­imidazole peryl­ene derivative used as a black pigment. The mol­ecule is entirely planar and possesses a center of symmetry. The mol­ecules are oriented in the same direction and are stacked with a considerable overlap of the peryl­ene imide skeleton along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.102
• wR factor = 0.222
• Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         28 Perc.

Author Response: The single crystal of the needle was slightly curved and the crystallinity was rather poor.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Author Response: A two-dimensional detector(IP) was used together with Cu target 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:      0.490     0.960
            Tmin' and Tmax expected:      0.716     0.960
            RR' =      0.684
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.68
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         12

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           68.20
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               1831
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2034
           Completeness (_total/calc)             90.02%
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.102
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.106
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.90
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.49
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C5     -C7_a          1.43 Ang.

   2 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   8 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
  11 ALERT type 3 Indicator that the structure quality may be low
   1 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

Dibenzimidazo[2,1 - a:2',1'-a']anthra[2,1,9-def:6,5,10 - d'e'f']diisoquinoline- 10,21-dione

Crystal data

C36H16N4O2	Z = 1
Mr = 536.53	F(000) = 276.00
Triclinic, P1	Dx = 1.602 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 4.729 (2) Å	Cell parameters from 3329 reflections
b = 8.282 (2) Å	θ = 3.0–68.2°
c = 14.693 (4) Å	µ = 0.82 mm^−1
α = 89.35 (2)°	T = 93 K
β = 91.15 (3)°	Needle, black
γ = 104.83 (3)°	0.40 × 0.05 × 0.05 mm
V = 556.2 (3) Å^3

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	505 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.106
48 frames, δ ω = 15° scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −4→4
Tmin = 0.490, Tmax = 0.960	k = −9→9
5005 measured reflections	l = −17→17
1831 independent reflections

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.102	w = 1/[σ^2(Fo^2) + {0.042[max(Fo^2,0) + 2Fc^2]/3)^2}
wR(F^2) = 0.222	(Δ/σ)max < 0.001
S = 0.93	Δρmax = 0.41 e Å^−3
1804 reflections	Δρmin = −0.41 e Å^−3
190 parameters

Special details

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 > 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	0.777 (1)	0.5903 (7)	0.3464 (4)	0.052 (2)
N1	0.756 (2)	0.3442 (10)	0.2746 (5)	0.043 (3)
N2	0.756 (2)	0.1001 (9)	0.2127 (5)	0.049 (3)
C1	0.672 (2)	0.495 (1)	0.2836 (6)	0.048 (3)
C2	0.479 (2)	0.531 (1)	0.2123 (5)	0.040 (3)
C3	0.382 (2)	0.674 (1)	0.2136 (6)	0.046 (3)
C4	0.202 (2)	0.715 (1)	0.1513 (6)	0.041 (3)
C5	0.094 (2)	0.610 (1)	0.0749 (6)	0.043 (3)
C6	0.187 (2)	0.456 (1)	0.0687 (7)	0.048 (3)
C7	0.097 (2)	0.350 (1)	−0.0062 (5)	0.041 (3)
C8	0.194 (2)	0.206 (1)	−0.0101 (5)	0.041 (3)
C9	0.366 (2)	0.165 (1)	0.0608 (6)	0.051 (3)
C10	0.469 (2)	0.268 (1)	0.1351 (6)	0.045 (3)
C11	0.649 (2)	0.229 (1)	0.2037 (6)	0.045 (3)
C12	0.377 (2)	0.421 (1)	0.1390 (6)	0.042 (3)
C13	0.923 (2)	0.119 (1)	0.2945 (6)	0.043 (3)
C14	1.074 (2)	0.016 (1)	0.3319 (6)	0.049 (3)
C15	1.236 (2)	0.075 (1)	0.4103 (6)	0.052 (4)
C16	1.248 (2)	0.229 (1)	0.4509 (6)	0.047 (3)
C17	1.090 (2)	0.325 (1)	0.4121 (6)	0.046 (3)
C18	0.935 (2)	0.276 (1)	0.3311 (6)	0.042 (3)
H1	0.4468	0.7492	0.2625	0.0554*
H2	0.1447	0.8160	0.1578	0.0487*
H3	0.1438	0.1349	−0.0613	0.0486*
H4	0.4157	0.0606	0.0580	0.0609*
H5	1.0697	−0.0892	0.3065	0.0586*
H6	1.3450	0.0059	0.4383	0.0626*
H7	1.3649	0.2642	0.5039	0.0569*
H8	1.0836	0.4272	0.4399	0.0548*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.086 (6)	0.032 (4)	0.033 (3)	0.005 (4)	−0.003 (3)	−0.002 (3)
N1	0.048 (6)	0.050 (5)	0.032 (4)	0.015 (4)	−0.008 (4)	−0.012 (4)
N2	0.060 (6)	0.041 (5)	0.046 (5)	0.008 (4)	0.018 (4)	0.003 (4)
C1	0.056 (8)	0.037 (6)	0.041 (6)	−0.008 (5)	0.010 (5)	0.013 (5)
C2	0.048 (7)	0.043 (6)	0.026 (5)	0.005 (5)	0.007 (5)	−0.005 (4)
C3	0.045 (7)	0.065 (7)	0.030 (5)	0.016 (5)	0.001 (5)	−0.023 (5)
C4	0.049 (7)	0.034 (5)	0.037 (5)	0.006 (5)	−0.001 (5)	0.000 (4)
C5	0.052 (7)	0.043 (6)	0.029 (5)	0.002 (5)	0.012 (5)	−0.006 (4)
C6	0.060 (8)	0.039 (6)	0.049 (6)	0.014 (5)	0.027 (5)	0.005 (5)
C7	0.038 (7)	0.070 (7)	0.018 (4)	0.021 (5)	0.012 (4)	0.011 (5)
C8	0.053 (7)	0.050 (6)	0.020 (5)	0.016 (5)	−0.001 (4)	−0.015 (4)
C9	0.059 (8)	0.046 (6)	0.044 (6)	0.007 (5)	0.000 (5)	−0.018 (5)
C10	0.037 (7)	0.045 (6)	0.044 (6)	−0.006 (5)	−0.012 (5)	−0.009 (5)
C11	0.051 (7)	0.046 (7)	0.035 (5)	0.009 (5)	0.007 (5)	0.004 (5)
C12	0.045 (7)	0.050 (6)	0.036 (5)	0.022 (5)	0.004 (5)	−0.002 (5)
C13	0.062 (7)	0.050 (6)	0.019 (4)	0.018 (5)	0.006 (4)	0.001 (4)
C14	0.057 (7)	0.058 (7)	0.030 (5)	0.012 (5)	0.000 (5)	−0.006 (5)
C15	0.067 (8)	0.059 (7)	0.033 (6)	0.021 (6)	0.012 (6)	−0.001 (5)
C16	0.055 (7)	0.058 (7)	0.031 (5)	0.017 (6)	0.011 (5)	0.006 (5)
C17	0.050 (7)	0.041 (6)	0.046 (6)	0.012 (5)	0.003 (5)	−0.006 (5)
C18	0.036 (7)	0.040 (6)	0.051 (6)	0.013 (5)	0.001 (5)	−0.003 (5)

Geometric parameters (Å, º)

O1—C1	1.233 (10)	C7—C8	1.38 (1)
N1—C1	1.41 (1)	C8—C9	1.40 (1)
N1—C11	1.41 (1)	C8—H3	0.950
N1—C18	1.39 (1)	C9—C10	1.40 (1)
N2—C11	1.30 (1)	C9—H4	0.950
N2—C13	1.42 (1)	C10—C11	1.39 (1)
C1—C2	1.45 (1)	C10—C12	1.45 (1)
C2—C3	1.38 (1)	C13—C14	1.35 (1)
C2—C12	1.41 (1)	C13—C18	1.41 (1)
C3—C4	1.34 (1)	C14—C15	1.39 (1)
C3—H1	0.946	C14—H5	0.950
C4—C5	1.43 (1)	C15—C16	1.40 (1)
C4—H2	0.951	C15—H6	0.952
C5—C6	1.46 (1)	C16—C17	1.34 (1)
C5—C7^i	1.43 (1)	C16—H7	0.952
C6—C7	1.41 (1)	C17—C18	1.39 (1)
C6—C12	1.43 (1)	C17—H8	0.951
O1···C16^ii	3.37 (1)	C4···C8^vii	3.48 (1)
O1···C3^iii	3.41 (1)	C5···C9^vii	3.41 (1)
O1···C14^iv	3.45 (1)	C5···C8^vii	3.47 (1)
O1···C4^iii	3.53 (1)	C5···C12^v	3.49 (1)
O1···C17^v	3.57 (1)	C6···C11^v	3.41 (1)
N1···C12^iii	3.50 (1)	C6···C7^vii	3.49 (1)
N1···C2^iii	3.51 (1)	C6···C10^v	3.51 (2)
N1···C15^v	3.51 (1)	C6···C6^vii	3.53 (2)
N1···C16^v	3.52 (1)	C7···C12^vii	3.36 (1)
N1···C3^iii	3.59 (1)	C7···C9^v	3.56 (1)
N2···C10^iii	3.51 (1)	C7···C10^v	3.57 (1)
N2···C3^vi	3.52 (1)	C8···C8^viii	3.45 (2)
N2···C12^iii	3.60 (1)	C8···C9^viii	3.58 (1)
C1···C4^iii	3.34 (1)	C10···C13^v	3.49 (1)
C1···C17^v	3.36 (1)	C11···C14^v	3.43 (1)
C1···C3^iii	3.47 (1)	C11···C12^iii	3.55 (1)
C1···C16^v	3.57 (1)	C11···C13^v	3.60 (1)
C1···C18^v	3.57 (1)	C12···C18^v	3.56 (1)
C2···C18^v	3.38 (1)	C15···C15^ix	3.49 (2)
C2···C5^iii	3.49 (1)	C15···C18^iii	3.52 (1)
C2···C4^iii	3.50 (1)	C15···C16^ix	3.59 (1)
C1—N1—C11	122.7 (8)	C8—C9—H4	118.4
C1—N1—C18	129.4 (8)	C10—C9—H4	118.0
C11—N1—C18	107.7 (8)	C9—C10—C11	123.7 (10)
C11—N2—C13	107.8 (7)	C9—C10—C12	116.5 (9)
O1—C1—N1	119.2 (9)	C11—C10—C12	119.8 (8)
O1—C1—C2	124.7 (9)	N1—C11—N2	110.3 (9)
N1—C1—C2	116.0 (8)	N1—C11—C10	120.3 (9)
C1—C2—C3	121.2 (8)	N2—C11—C10	129.3 (9)
C1—C2—C12	122.6 (9)	C2—C12—C6	122.9 (9)
C3—C2—C12	116.2 (9)	C2—C12—C10	118.5 (9)
C2—C3—C4	124.6 (8)	C6—C12—C10	118.6 (8)
C2—C3—H1	117.6	N2—C13—C14	129.4 (8)
C4—C3—H1	117.8	N2—C13—C18	108.5 (8)
C3—C4—C5	121.8 (9)	C14—C13—C18	122.0 (9)
C3—C4—H2	119.0	C13—C14—C15	115.8 (9)
C5—C4—H2	119.2	C13—C14—H5	122.0
C4—C5—C6	116.9 (9)	C15—C14—H5	122.2
C4—C5—C7^i	123.3 (9)	C14—C15—C16	124.5 (10)
C6—C5—C7^i	119.9 (8)	C14—C15—H6	117.9
C5—C6—C7	119.7 (10)	C16—C15—H6	117.5
C5—C6—C12	117.6 (9)	C15—C16—C17	117.6 (9)
C7—C6—C12	122.6 (9)	C15—C16—H7	121.2
C5^i—C7—C6	120.4 (9)	C17—C16—H7	121.2
C5^i—C7—C8	121.9 (8)	C16—C17—C18	120.3 (8)
C6—C7—C8	117.7 (9)	C16—C17—H8	119.9
C7—C8—C9	120.8 (7)	C18—C17—H8	119.8
C7—C8—H3	119.6	N1—C18—C13	105.4 (8)
C9—C8—H3	119.6	N1—C18—C17	134.7 (9)
C8—C9—C10	123.6 (9)	C13—C18—C17	119.7 (8)
C4—C5—C7^i—C8^i	0 (1)

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