Dibenzimidazo­[2,1-a:1',2'-b']­anthra­[2,1,9-def:6,5,10-d'e'f']­diiso­quinoline-6,11-dione: cis form (II)

The title compound, C₃₆H₁₆N₄O₂, is the cis form of a benz­imidazole peryl­ene derivative used as a black pigment. The mol­ecule is planar and stacked along the a axis. Because of an orientational disorder, a crystallographic center of symmetry appears at the site of the mol­ecule, although the mol­ecule does not have a center of symmetry.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.083
• wR factor = 0.196
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.94

Author Response: A two-dimentional detector (IP) was used together with Cu radiation for the collection of reflection data. Therefore, the completeness is rather low.

Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C19
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C5

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               1969
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2107
           Completeness (_total/calc)             93.45%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.94
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.31 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.09
PLAT301_ALERT_3_C Main Residue  Disorder .........................      25.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   1 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  13 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
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 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: 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	F(000) = 552.00
Mr = 536.55	Dx = 1.551 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 8833 reflections
a = 4.7501 (6) Å	θ = 3.2–71.6°
b = 28.079 (3) Å	µ = 0.79 mm^−1
c = 8.728 (1) Å	T = 93 K
β = 99.21 (1)°	Needle, black
V = 1149.1 (2) Å^3	0.50 × 0.05 × 0.02 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	791 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.08
48 frames, δ ω = 15° scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −4→4
Tmin = 0.727, Tmax = 0.984	k = −33→33
12407 measured reflections	l = −10→10
1969 independent reflections

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.083	w = 1/[σ^2(Fo^2) + {0.05[Max(Fo^2,0) + 2Fc^2]/3}^2]
wR(F^2) = 0.196	(Δ/σ)max = 0.009
S = 1.14	Δρmax = 0.30 e Å^−3
1963 reflections	Δρmin = −0.25 e Å^−3
188 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	Occ. (<1)
O1	−0.227 (1)	0.6828 (2)	1.0028 (7)	0.044 (2)*	0.50
O2	−0.530 (2)	0.5723 (3)	0.5387 (9)	0.055 (3)	0.50
N1	−0.3786 (9)	0.6299 (2)	0.7684 (7)	0.072 (2)
N2	−0.536 (3)	0.5931 (3)	0.577 (1)	0.046 (3)*	0.50
N3	−0.283 (2)	0.6782 (3)	0.933 (1)	0.047 (2)*	0.50
C1	−0.698 (2)	0.6327 (3)	0.5746 (9)	0.032 (2)*	0.50
C2	−0.930 (2)	0.6506 (3)	0.468 (1)	0.042 (2)*	0.50
C3	−1.037 (2)	0.6902 (4)	0.492 (1)	0.055 (3)*	0.50
C4	−0.941 (2)	0.7181 (4)	0.628 (1)	0.036 (3)*	0.50
C5	−0.716 (2)	0.7018 (3)	0.731 (1)	0.039 (2)*	0.50
C6	−0.5947 (9)	0.6593 (2)	0.7009 (6)	0.046 (2)
C7	−0.199 (1)	0.6428 (2)	0.9021 (8)	0.073 (2)
C8	0.0314 (10)	0.6095 (2)	0.9615 (6)	0.048 (2)
C9	0.2159 (10)	0.6192 (2)	1.0904 (6)	0.051 (2)
C10	0.4313 (9)	0.5880 (2)	1.1498 (5)	0.046 (2)
C11	0.4689 (9)	0.5451 (2)	1.0776 (5)	0.041 (1)
C12	0.2802 (9)	0.5328 (2)	0.9408 (5)	0.039 (1)
C13	0.0573 (9)	0.5656 (2)	0.8811 (5)	0.045 (2)
C14	0.6951 (9)	0.5111 (2)	1.1404 (5)	0.041 (1)
C15	0.8896 (9)	0.5209 (2)	1.2709 (5)	0.049 (2)
C16	1.1082 (9)	0.4887 (2)	1.3278 (5)	0.053 (2)
C17	1.1336 (9)	0.4455 (2)	1.2539 (6)	0.050 (2)
C18	−0.3559 (10)	0.5884 (2)	0.6834 (7)	0.068 (2)
C19	−0.801 (3)	0.6624 (4)	0.577 (1)	0.081 (4)*	0.50
C20	−0.988 (3)	0.7054 (5)	0.566 (2)	0.062 (4)*	0.50
C21	−0.886 (3)	0.7350 (5)	0.695 (2)	0.090 (5)*	0.50
C22	−0.679 (3)	0.7286 (5)	0.803 (2)	0.106 (5)*	0.50
C23	−0.518 (3)	0.6906 (4)	0.816 (1)	0.075 (3)*	0.50
H1	0.1984	0.6485	1.1428	0.0614*
H2	0.5562	0.5961	1.2423	0.0552*
H3	0.8761	0.5502	1.3239	0.0592*
H4	1.2400	0.4966	1.4180	0.0637*
H5	−0.9995	0.6288	0.3728	0.0447*	0.50
H6	−1.2123	0.7046	0.4144	0.0599*	0.50
H7	−1.0279	0.7483	0.6473	0.0386*	0.50
H8	−0.6472	0.7225	0.8226	0.0483*	0.50
H9	−0.8528	0.6373	0.4869	0.1029*	0.50
H10	−1.1488	0.7099	0.4764	0.0720*	0.50
H11	−1.0329	0.7675	0.6877	0.0969*	0.50
H12	−0.6422	0.7520	0.8999	0.0831*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.027 (4)	0.073 (6)	0.064 (5)	0.000 (4)	0.003 (4)	0.018 (5)
N1	0.031 (3)	0.076 (4)	0.114 (5)	0.013 (3)	0.025 (3)	0.052 (3)
C6	0.028 (3)	0.047 (3)	0.065 (3)	−0.003 (2)	0.012 (2)	0.021 (3)
C7	0.032 (4)	0.071 (4)	0.122 (6)	0.007 (3)	0.029 (3)	0.054 (4)
C8	0.036 (3)	0.046 (3)	0.066 (4)	0.003 (2)	0.018 (3)	0.017 (3)
C9	0.033 (3)	0.049 (3)	0.073 (4)	0.002 (2)	0.014 (3)	0.011 (3)
C10	0.037 (3)	0.048 (3)	0.056 (3)	−0.009 (2)	0.015 (2)	−0.001 (2)
C11	0.031 (3)	0.047 (3)	0.045 (3)	−0.009 (2)	0.011 (2)	0.006 (2)
C12	0.029 (3)	0.043 (3)	0.048 (3)	0.001 (2)	0.013 (2)	0.015 (2)
C13	0.031 (3)	0.057 (3)	0.048 (3)	−0.001 (2)	0.013 (2)	0.018 (3)
C14	0.030 (3)	0.045 (3)	0.049 (3)	−0.005 (2)	0.007 (2)	0.015 (2)
C15	0.037 (3)	0.058 (3)	0.054 (3)	−0.004 (2)	0.011 (2)	0.012 (3)
C16	0.034 (3)	0.080 (4)	0.046 (3)	−0.005 (3)	0.006 (2)	0.021 (3)
C17	0.038 (3)	0.059 (4)	0.058 (3)	−0.004 (3)	0.018 (3)	0.018 (3)
C18	0.021 (3)	0.100 (5)	0.083 (5)	0.009 (3)	0.011 (3)	0.058 (4)

Geometric parameters (Å, º)

O1—C7	1.444 (9)	C9—C10	1.385 (6)
O2—C18	1.467 (10)	C9—H1	0.950
N1—C6	1.374 (6)	C10—C11	1.382 (5)
N1—C7	1.378 (6)	C10—H2	0.950
N1—C18	1.395 (7)	C11—C12	1.416 (5)
N2—C1	1.35 (1)	C11—C14	1.476 (5)
N2—C18	1.16 (1)	C12—C13	1.437 (5)
N3—C7	1.119 (9)	C12—C14^i	1.436 (5)
N3—C23	1.43 (1)	C13—C17^i	1.402 (6)
C1—C2	1.41 (1)	C14—C15	1.375 (5)
C1—C6	1.355 (9)	C15—C16	1.407 (5)
C2—C3	1.25 (1)	C15—H3	0.950
C2—H5	1.044	C16—C17	1.388 (6)
C3—C4	1.43 (1)	C16—H4	0.950
C3—H6	1.069	C17—C18^i	1.461 (6)
C4—C5	1.36 (1)	C19—C20	1.49 (2)
C4—H7	0.969	C19—H9	1.052
C5—C6	1.370 (10)	C20—C21	1.42 (2)
C5—H8	1.000	C20—H10	1.010
C6—C23	1.34 (1)	C21—C22	1.26 (2)
C7—C8	1.472 (6)	C21—H11	1.143
C8—C9	1.340 (6)	C22—C23	1.31 (2)
C8—C13	1.432 (6)	C22—H12	1.064
O1···C21^ii	3.15 (2)	C4···C23^iii	3.50 (2)
O1···C4^ii	3.21 (1)	C4···C7^iii	3.56 (1)
O1···C20^ii	3.35 (1)	C5···C7^iii	3.368 (9)
O1···C9^iii	3.379 (8)	C6···C8^iii	3.403 (6)
O1···C10^iii	3.469 (7)	C6···C20^iv	3.53 (1)
O1···C22^iv	3.60 (1)	C7···C10^iii	3.367 (6)
O2···C16^v	3.292 (9)	C7···C9^iii	3.509 (6)
O2···C10^vi	3.398 (9)	C8···C23^iv	3.50 (1)
O2···C16^vii	3.585 (8)	C8···C11^iii	3.506 (6)
N1···C20^iv	3.48 (1)	C8···C10^iii	3.562 (6)
N1···C13^iii	3.500 (6)	C9···C23^iv	3.51 (1)
N1···C8^iii	3.541 (6)	C10···C15^iii	3.486 (6)
N1···C3^iv	3.54 (1)	C11···C16^iii	3.379 (5)
N1···C19^iv	3.55 (1)	C11···C15^iii	3.517 (5)
N1···C4^iv	3.58 (1)	C11···C13^iv	3.552 (6)
N2···C2^iv	3.56 (1)	C12···C18^iv	3.422 (6)
N2···C17^vii	3.57 (1)	C12···C12^vii	3.525 (8)
N3···C9^iii	3.367 (9)	C12···C17^ix	3.539 (6)
N3···C21^iv	3.42 (1)	C12···C14^iii	3.561 (5)
N3···C5^iv	3.51 (1)	C13···C14^iii	3.416 (5)
N3···C4^iv	3.52 (1)	C13···C18^iv	3.563 (6)
N3···C22^iv	3.55 (1)	C14···C16^iii	3.508 (6)
N3···C10^iii	3.558 (9)	C14···C17^iii	3.512 (6)
C1···C17^vii	3.514 (8)	C15···C16^x	3.511 (6)
C2···C18^iii	3.450 (9)	C16···C16^x	3.388 (9)
C2···C9^vi	3.585 (10)	C18···C19^iv	3.59 (1)
C3···C22^viii	3.42 (2)	C20···C22^viii	3.46 (2)
C3···C21^viii	3.50 (2)	C21···C23^iii	3.57 (2)
C3···C6^iii	3.55 (1)
C6—N1—C7	121.5 (6)	C11—C12—C13	118.6 (4)
C6—N1—C18	113.0 (5)	C11—C12—C14^i	122.4 (4)
C7—N1—C18	125.5 (5)	C13—C12—C14^i	119.0 (4)
C1—N2—C18	116.7 (9)	C8—C13—C12	119.3 (4)
N2—C1—C2	133.2 (9)	C8—C13—C17^i	120.5 (5)
N2—C1—C6	108.0 (8)	C12—C13—C17^i	120.2 (5)
C2—C1—C6	118.7 (8)	C11—C14—C12^i	118.9 (4)
C1—C2—C3	119.9 (9)	C11—C14—C15	122.1 (4)
C1—C2—H5	115.5	C12^i—C14—C15	119.0 (4)
C3—C2—H5	124.7	C14—C15—C16	121.6 (5)
C2—C3—C4	122.8 (9)	C14—C15—H3	119.2
C2—C3—H6	121.6	C16—C15—H3	119.2
C4—C3—H6	115.6	C15—C16—C17	120.8 (4)
C3—C4—C5	118.3 (10)	C15—C16—H4	119.6
C3—C4—H7	122.2	C17—C16—H4	119.6
C5—C4—H7	119.6	C13^i—C17—C16	119.5 (5)
C4—C5—C6	118.5 (9)	C13^i—C17—C18^i	120.1 (5)
C4—C5—H8	117.0	C16—C17—C18^i	120.4 (5)
C6—C5—H8	124.4	O2—C18—N1	129.3 (6)
N1—C6—C1	99.6 (6)	O2—C18—C17^i	113.4 (6)
N1—C6—C5	138.6 (7)	N1—C18—N2	102.7 (7)
C1—C6—C5	121.8 (6)	N1—C18—C17^i	117.2 (5)
O1—C7—N1	128.1 (6)	N2—C18—C17^i	140.1 (9)
O1—C7—C8	114.5 (6)	C6—C19—H9	127.6
N1—C7—C8	117.0 (6)	C20—C19—H9	115.5
C7—C8—C9	121.0 (5)	C19—C20—C21	107 (1)
C7—C8—C13	119.5 (5)	C19—C20—H10	121.1
C9—C8—C13	119.5 (4)	C21—C20—H10	131.3
C8—C9—H1	119.1	C20—C21—C22	129 (1)
C10—C9—H1	119.0	C20—C21—H11	107.2
C9—C10—C11	121.5 (5)	C22—C21—H11	123.5
C9—C10—H2	119.2	C21—C22—C23	124 (1)
C11—C10—H2	119.2	C21—C22—H12	121.1
C10—C11—C12	119.1 (4)	C23—C22—H12	114.3
C10—C11—C14	122.2 (4)	N3—C23—C22	129 (1)
C12—C11—C14	118.7 (4)	N3—C23—H12	101.1
C10—C11—C14—C15	−2.8 (6)	C11—C14—C15—C16	−178.6 (4)

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