3,3′-(1,4-Dioxopyrrolo[3,4-c]pyrrole-3,6-diyl)dibenzonitrile dimethyl­acetamide disolvate

Mizuguchi, J.; Arai, A.

doi:10.1107/S1600536806035677

3,3′-(1,4-Dioxopyrrolo[3,4-c]pyrrole-3,6-diyl)dibenzonitrile dimethylacetamide disolvate

The title compound, C₂₀H₁₀N₄O₂·2C₄H₉NO, is a solvated centrosymmetric pigment molecule (m-CN DPP) with the two dimethylacetamide (DMA) molecules connected via N—H

O hydrogen bonds. One m-CN DPP molecule is surrounded by six DMA molecules in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035677/ob2060sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035677/ob2060Isup2.hkl Contains datablock I

CCDC reference: 624946

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Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.010 Å
R factor = 0.109
wR factor = 0.347
Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         22 Perc.

Author Response: This is primarily caused by poor crystallinity of our tiny solvated crystals. Secondarily, the crystallinity was further decreased gradually due to mobile solvent molecules during the measurements carried out at room temperature.


Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      0.850
            Test value =      0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       0.85 e/A   

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.109
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.347
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT082_ALERT_2_C High R1 Value ..................................       0.11
PLAT084_ALERT_2_C High R2 Value ..................................       0.35
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.30
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C11
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C10    ...       1.46 Ang.

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Rigaku/MSC, 2000); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

3,3'-(1,4-dioxopyrrolo[3,4-c]pyrrole-3,6-diyl)dibenzonitrile dimethylacetamide disolvate top

Crystal data top

C₂₀H₁₀N₄O₂·2C₄H₉NO	F(000) = 540.00
M_r = 512.56	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.129 (5) Å	θ = 10.5–13.2°
b = 4.020 (5) Å	µ = 0.09 mm⁻¹
c = 20.676 (6) Å	T = 296 K
β = 105.18 (2)°	Platelet, orange
V = 1293.8 (17) Å³	0.40 × 0.10 × 0.03 mm
Z = 2

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.082
ω/2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→20
T_min = 0.968, T_max = 0.997	k = −5→0
3078 measured reflections	l = −26→25
2975 independent reflections	3 standard reflections every 0 reflections
665 reflections with F² > 2σ(F²)	intensity decay: 22.0%

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.109	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.347	(Δ/σ)_max < 0.001
S = 1.14	Δρ_max = 0.85 e Å⁻³
2975 reflections	Δρ_min = −0.37 e Å⁻³
143 parameters

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Following bonds and angles of DMA were restrained: bond distances of C11—C12, C11—O2, C11—N3, N3—C13 and N3—C14, and bond angles of C11/N3/C13 and C13/N3/C14. The highest residual density peak of 0.85 e Å^-3 was located 1.00 Å from atom N3.

Refinement using reflections with F² > 2 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2 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	U_iso*/U_eq
O1	0.5981 (3)	0.3044 (16)	0.6276 (2)	0.0608 (18)
O2	0.7780 (3)	0.6305 (17)	0.5472 (3)	0.0781 (19)
N1	0.6219 (3)	0.2455 (16)	0.5222 (2)	0.0434 (18)
N2	0.8766 (4)	0.525 (2)	0.3587 (4)	0.091 (3)
N3	0.8872 (6)	0.884 (2)	0.6079 (4)	0.117 (3)
C1	0.6180 (4)	0.127 (2)	0.4033 (3)	0.039 (2)
C2	0.6974 (4)	0.259 (2)	0.4072 (3)	0.046 (2)
C3	0.7264 (4)	0.274 (2)	0.3508 (3)	0.044 (2)
C4	0.6792 (5)	0.159 (2)	0.2897 (4)	0.058 (2)
C5	0.6010 (5)	0.020 (2)	0.2856 (3)	0.055 (2)
C6	0.5666 (4)	0.003 (2)	0.3410 (3)	0.045 (2)
C7	0.5779 (4)	0.109 (2)	0.4604 (3)	0.0365 (19)
C8	0.5028 (4)	−0.0263 (19)	0.4668 (2)	0.0328 (18)
C9	0.5737 (4)	0.204 (2)	0.5695 (3)	0.041 (2)
C10	0.8114 (6)	0.409 (2)	0.3552 (4)	0.064 (2)
C11	0.8172 (8)	0.764 (3)	0.6047 (6)	0.123 (5)
C12	0.7842 (5)	0.787 (2)	0.6674 (4)	0.081 (2)
C13	0.9418 (5)	1.030 (2)	0.6689 (4)	0.079 (3)
C14	0.9180 (5)	0.879 (2)	0.5419 (4)	0.090 (3)
H1N	0.6712	0.3412	0.5302	0.052*
H2	0.7313	0.3378	0.4478	0.055*
H4	0.7002	0.1759	0.2520	0.070*
H5	0.5695	−0.0669	0.2448	0.066*
H6	0.5123	−0.0849	0.3373	0.054*
H12A	0.8082	0.9790	0.6902	0.097*
H12B	0.7250	0.7920	0.6536	0.097*
H12C	0.8048	0.5937	0.6930	0.097*
H13A	0.9301	1.2642	0.6698	0.098*
H13B	1.0011	0.9980	0.6697	0.098*
H13C	0.9302	0.9250	0.7073	0.098*
H14A	0.9482	0.6755	0.5396	0.100*
H14B	0.9555	1.0644	0.5419	0.100*
H14C	0.8690	0.8944	0.5038	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.054 (3)	0.089 (5)	0.037 (3)	−0.022 (3)	0.009 (2)	−0.014 (3)
O2	0.07 (17)	0.074 (6)	0.074 (4)	0.000 (4)	0.000 (3)	0.000 (4)
N1	0.033 (3)	0.065 (5)	0.027 (3)	−0.006 (3)	−0.001 (2)	−0.010 (3)
N2	0.053 (4)	0.121 (8)	0.104 (6)	−0.032 (5)	0.030 (4)	0.000 (6)
N3	0.1 (3)	0.112 (6)	0.112 (13)	0.000 (5)	0.000 (7)	0.000 (8)
C1	0.037 (4)	0.049 (5)	0.031 (3)	0.006 (4)	0.010 (3)	0.011 (3)
C2	0.039 (4)	0.058 (6)	0.046 (4)	0.006 (4)	0.019 (3)	0.007 (4)
C3	0.032 (3)	0.058 (6)	0.043 (4)	−0.001 (4)	0.014 (3)	0.004 (4)
C4	0.066 (5)	0.071 (7)	0.048 (5)	−0.006 (5)	0.033 (4)	0.005 (5)
C5	0.057 (5)	0.064 (6)	0.045 (4)	−0.012 (5)	0.016 (3)	0.003 (5)
C6	0.043 (4)	0.052 (5)	0.037 (4)	0.000 (4)	0.004 (3)	0.000 (4)
C7	0.031 (3)	0.049 (5)	0.030 (3)	−0.004 (4)	0.010 (3)	0.000 (3)
C8	0.034 (3)	0.041 (5)	0.026 (3)	−0.012 (4)	0.012 (3)	−0.006 (3)
C9	0.040 (4)	0.053 (6)	0.028 (3)	−0.002 (4)	0.008 (3)	0.004 (4)
C10	0.068 (5)	0.075 (7)	0.058 (5)	0.000 (6)	0.032 (4)	0.009 (5)
C11	0.1 (4)	0.118 (8)	0.118 (17)	0.000 (7)	0.000 (9)	0.000 (9)
C12	0.1 (2)	0.077 (8)	0.077 (7)	0.000 (6)	0.000 (6)	0.000 (6)
C13	0.1 (2)	0.076 (7)	0.076 (7)	0.000 (5)	0.000 (4)	0.000 (6)
C14	0.1 (2)	0.086 (10)	0.086 (7)	0.000 (7)	0.000 (6)	0.000 (8)

Geometric parameters (Å, º) top

O1—C9	1.230 (8)	C4—C5	1.363 (12)
O2—C11	1.307 (14)	C4—H4	0.930
N1—C7	1.400 (8)	C5—C6	1.398 (12)
N1—C9	1.410 (10)	C5—H5	0.930
N1—H1N	0.860	C6—H6	0.930
N2—C10	1.136 (13)	C7—C8	1.365 (10)
N3—C11	1.213 (17)	C8—C8ⁱ	1.417 (9)
N3—C13	1.460 (12)	C8—C9ⁱ	1.452 (9)
N3—C14	1.568 (15)	C11—C12	1.528 (18)
C1—C2	1.370 (10)	C13—H13A	0.960
C1—C6	1.426 (9)	C13—H13B	0.960
C1—C7	1.490 (10)	C13—H13C	0.960
C2—C3	1.365 (12)	C14—H14A	0.960
C2—H2	0.930	C14—H14B	0.960
C3—C4	1.373 (10)	C14—H14C	0.960
C3—C10	1.456 (13)

O1···H4ⁱⁱ	2.667	H12A···H12C	1.5514
O1···H5ⁱⁱ	2.790	H12A···H12C^viii	2.4727
O1···H12B	2.783	H12A···H13A	2.406
O2···H1N	2.030	H12A···H13C	1.919
O2···H2	2.316	H12B···O1	2.783
O2···H12B	2.642	H12B···O2	2.642
N3···H12A	2.409	H12B···C11	2.010
N3···H12C	2.730	H12B···C12	0.923
C11···H12A	2.007	H12B···H12A	1.5514
C11···H12B	2.010	H12B···H12C	1.5514
C11···H12C	2.009	H12C···N3	2.730
C12···H12A	0.934	H12C···C11	2.009
C12···H12B	0.923	H12C···C12	0.950
C12···H12C	0.950	H12C···H4ⁱⁱ	2.567
C13···H12A	2.319	H12C···H12A^ix	2.4727
H1N···O2	2.030	H12C···H12A	1.5514
H2···O2	2.316	H12C···H12B	1.5514
H4···O1ⁱⁱⁱ	2.667	H12C···H13A^ix	2.563
H4···H12A^iv	2.785	H12C···H13C	2.375
H4···H12Cⁱⁱⁱ	2.567	H13A···H12A	2.406
H5···O1ⁱⁱⁱ	2.790	H13A···H12C^viii	2.563
H5···H6^v	2.790	H13A···H13C^viii	2.767
H5···H6^vi	2.684	H13C···H12A	1.919
H6···H5^v	2.684	H13C···H12C	2.375
H6···H5^vi	2.790	H13C···H13A^ix	2.767
H12A···N3	2.409	H14A···H14B^ix	2.459
H12A···C11	2.007	H14A···H14B^x	2.779
H12A···C12	0.934	H14B···H14A^viii	2.459
H12A···C13	2.319	H14B···H14A^x	2.779
H12A···H4^vii	2.785	H14B···H14B^x	2.575
H12A···H12B	1.5514

C7—N1—C9	110.3 (5)	C7—C8—C9ⁱ	143.3 (6)
C7—N1—H1N	124.9	C8ⁱ—C8—C9ⁱ	108.2 (6)
C9—N1—H1N	124.9	O1—C9—N1	123.0 (6)
C11—N3—C13	123.3 (11)	O1—C9—C8ⁱ	132.6 (7)
C11—N3—C14	116.7 (9)	N1—C9—C8ⁱ	104.4 (5)
C13—N3—C14	120.0 (8)	N2—C10—C3	177.6 (11)
C2—C1—C6	120.1 (7)	O2—C11—N3	115.8 (12)
C2—C1—C7	124.4 (6)	O2—C11—C12	127.0 (11)
C6—C1—C7	115.5 (6)	N3—C11—C12	117.1 (10)
C1—C2—C3	119.4 (6)	C11—C12—H12A	106.7
C1—C2—H2	120.3	C11—C12—H12B	107.6
C3—C2—H2	120.3	C11—C12—H12C	106.0
C2—C3—C4	122.7 (7)	H12A—C12—H12B	113.3
C2—C3—C10	119.3 (6)	H12A—C12—H12C	110.9
C4—C3—C10	118.0 (7)	H12B—C12—H12C	111.9
C3—C4—C5	118.5 (8)	N3—C13—H13A	109.5
C3—C4—H4	120.8	N3—C13—H13B	109.5
C5—C4—H4	120.8	N3—C13—H13C	109.5
C4—C5—C6	121.8 (7)	H13A—C13—H13B	109.5
C4—C5—H5	119.1	H13A—C13—H13C	109.5
C6—C5—H5	119.1	H13B—C13—H13C	109.5
C1—C6—C5	117.6 (6)	N3—C14—H14A	109.5
C1—C6—H6	121.2	N3—C14—H14B	109.5
C5—C6—H6	121.2	N3—C14—H14C	109.5
N1—C7—C1	118.9 (5)	H14A—C14—H14B	109.5
N1—C7—C8	108.6 (6)	H14A—C14—H14C	109.5
C1—C7—C8	132.5 (6)	H14B—C14—H14C	109.5
C7—C8—C8ⁱ	108.5 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	2.03	2.884 (8)	172

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3,3′-(1,4-Dioxopyrrolo[3,4-c]pyrrole-3,6-diyl)dibenzonitrile dimethyl­acetamide disolvate

Supporting information

Key indicators

checkCIF/PLATON results

3,3′-(1,4-Dioxopyrrolo[3,4-c]pyrrole-3,6-diyl)dibenzonitrile dimethylacetamide disolvate