3,6-Di-4-pyridyl­pyrrolo­[3,4-c]­pyrrole-1,4(2H,5H)-dione

The centrosymmetric title compound, C₁₆H₁₀N₄O₂, is an organic red pigment utilized for H₂ gas sensors. The centrosymmetric diketo­pyrrolo­pyrrole moieties are connected by bifurcated N...H...O hydrogen bonds to form a ribbon structure along [110] and [10] alternately. The mol­ecules are stacked in a `hunter's fence' (viz. when viewed from the side, molecules, slipped by 45° within molecular stacks, cross each other in a fence-like structure) fashion along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.241
• wR factor = 0.565
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSTM02_ALERT_3_A  The ratio of expected to reported Tmax/Tmin(RR') is < 0.50
            Tmin and Tmax reported:      0.009     0.982
            Tmin' and Tmax expected:      0.825     0.982
            RR' =      0.011
            Please check that your absorption correction is appropriate.

Author Response: The single crystal used for measurements was extremely small and thin (0.2x0.1x0.02 mm^3).

RFACG01_ALERT_3_A  The value of the R factor is > 0.20
            R factor given   0.241

Author Response: The single crystal used for the analysis was extremely small and and thin (0.2x0.1x0.02 mm^3). In addition, the crystal was slightly curved and the crystallinity was rather poor. Nevertheless, this was the maximum which we could do.

RFACR01_ALERT_3_A  The value of the weighted R factor is > 0.45
            Weighted R factor given   0.565

Author Response: The single crystal used for the analysis was extremely small and and thin (0.2x0.1x0.02 mm^3). In addition, the crystal was slightly curved and the crystallinity was rather poor. Nevertheless, this was the maximum which we could do.

RINTA01_ALERT_3_A  The value of Rint is greater than 0.20
            Rint given   0.246

Author Response: The single crystal used for the analysis was extremely small and and thin (0.2x0.1x0.02 mm^3). In addition, the crystal was slightly curved and the crystallinity was rather poor. Nevertheless, this was the maximum which we could do.

PLAT020_ALERT_3_A The value of Rint is greater than 0.10 .........       0.25

Author Response: The single crystal used for the analysis was extremely small and and thin (0.2x0.1x0.02 mm^3). In addition, the crystal was slightly curved and the crystallinity was rather poor. Nevertheless, this was the maximum which we could do.

PLAT061_ALERT_3_A Tmax/Tmin Range Test RR' too Large .............       0.01

Author Response: The single crystal used for measurements was extremely small and thin (0.2x0.1x0.02 mm^3).

PLAT082_ALERT_2_A High R1 Value ..................................       0.24

Author Response: The single crystal used for the analysis was extremely small and and thin (0.2x0.1x0.02 mm^3). In addition, the crystal was slightly curved and the crystallinity was rather poor. Nevertheless, this was the maximum which we could do.

PLAT084_ALERT_2_A High R2 Value ..................................       0.56

Author Response: The single crystal used for the analysis was extremely small and and thin (0.2x0.1x0.02 mm^3). In addition, the crystal was slightly curved and the crystallinity was rather poor. Nevertheless, this was the maximum which we could do.

Alert level B
DIFMN02_ALERT_2_B  The minimum difference density is < -0.1*ZMAX*1.00
            _refine_diff_density_min given =     -1.400
            Test value =     -0.800
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      1.600
            Test value =      0.800
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       1.60 e/A   3
PLAT098_ALERT_2_B Minimum (Negative) Residual Density ............      -1.40 e/A   3

Alert level C
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
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...     616.00 Ang-3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.85
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

   8 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
   6 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   8 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

C16H10N4O2	F(000) = 300.0
Mr = 290.28	Dx = 1.565 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5419 Å
Hall symbol: -P 2yn	Cell parameters from 4967 reflections
a = 3.722 (1) Å	θ = 3.3–68.3°
b = 6.263 (3) Å	µ = 0.89 mm^−1
c = 26.506 (9) Å	T = 93 K
β = 94.41 (2)°	Platelet, red
V = 616.0 (4) Å^3	0.20 × 0.10 × 0.02 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	711 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.246
48 frames, δ ω = 15° scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→4
Tmin = 0.009, Tmax = 0.982	k = 0→6
6710 measured reflections	l = −31→31
1089 independent reflections

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.241	w = 1/[σ^2(Fo^2) + {0.187[Max(Fo^2,0) + 2Fc^2]/3}^2]
wR(F^2) = 0.565	(Δ/σ)max < 0.001
S = 1.78	Δρmax = 1.60 e Å^−3
1089 reflections	Δρmin = −1.40 e Å^−3
100 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 > 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	0.858 (2)	0.8404 (9)	0.4440 (2)	0.0509
N1	0.503 (2)	0.707 (1)	0.7167 (3)	0.0541
N2	0.727 (2)	0.7912 (10)	0.5273 (2)	0.0442
C1	0.541 (2)	0.667 (1)	0.6115 (3)	0.0465
C2	0.647 (2)	0.855 (1)	0.6375 (3)	0.0491
C3	0.630 (2)	0.865 (1)	0.6875 (3)	0.0481
C4	0.398 (2)	0.526 (1)	0.6921 (3)	0.0481
C5	0.405 (2)	0.499 (1)	0.6413 (3)	0.0466
C6	0.560 (2)	0.640 (1)	0.5577 (3)	0.0479
C7	0.455 (2)	0.477 (1)	0.5251 (3)	0.0461
C8	0.730 (2)	0.733 (1)	0.4776 (3)	0.0430
H1	0.8279	0.9212	0.5402	0.0531*
H2	0.7307	0.9745	0.6195	0.0589*
H3	0.7125	0.9926	0.7041	0.0577*
H4	0.3136	0.4113	0.7114	0.0577*
H5	0.3216	0.3699	0.6258	0.0559*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0624	0.0262	0.0633	−0.0000	−0.0005	−0.0004
N1	0.0570	0.0282	0.0763	−0.0013	−0.0014	−0.0015
N2	0.0466	0.0181	0.0675	−0.0012	0.0015	−0.0050
C1	0.0448	0.0193	0.0756	0.0026	0.0069	0.0028
C2	0.0452	0.0260	0.0754	0.0051	0.0002	0.0036
C3	0.0446	0.0292	0.0697	0.0029	−0.0001	0.0082
C4	0.0390	0.0310	0.0733	0.0071	−0.0022	−0.0007
C5	0.0415	0.0256	0.0727	−0.0031	0.0051	−0.0010
C6	0.0542	0.0284	0.0598	−0.0044	−0.0053	0.0009
C7	0.0552	0.0136	0.0686	0.0028	−0.0023	0.0001
C8	0.0404	0.0274	0.0612	0.0013	0.0041	0.0016

Geometric parameters (Å, º)

O1—C8	1.240 (10)	C2—C3	1.33 (1)
N1—C3	1.36 (1)	C2—H2	0.950
N1—C4	1.35 (1)	C3—H3	0.950
N2—C6	1.42 (1)	C4—C5	1.36 (1)
N2—C8	1.367 (10)	C4—H4	0.950
N2—H1	0.950	C5—H5	0.950
C1—C2	1.40 (1)	C6—C7	1.37 (1)
C1—C5	1.43 (1)	C7—C7^i	1.43 (2)
C1—C6	1.45 (1)	C7—C8^i	1.48 (1)
O1···N2^ii	2.847 (8)	N2···C6^iv	3.28 (1)
O1···C7^iii	3.29 (1)
C3—N1—C4	115.7 (7)	N1—C4—H4	118.1
C6—N2—C8	113.8 (6)	C5—C4—H4	118.1
C6—N2—H1	123.1	C1—C5—C4	119.3 (8)
C8—N2—H1	123.1	C1—C5—H5	120.4
C2—C1—C5	116.4 (8)	C4—C5—H5	120.4
C2—C1—C6	123.5 (8)	N2—C6—C1	122.4 (7)
C5—C1—C6	120.1 (7)	N2—C6—C7	104.8 (7)
C1—C2—C3	119.5 (8)	C1—C6—C7	132.7 (8)
C1—C2—H2	120.2	C6—C7—C7^i	111.3 (9)
C3—C2—H2	120.2	C6—C7—C8^i	142.8 (8)
N1—C3—C2	125.2 (8)	C7^i—C7—C8^i	105.9 (8)
N1—C3—H3	117.4	O1—C8—N2	125.4 (7)
C2—C3—H3	117.4	O1—C8—C7^i	130.4 (7)
N1—C4—C5	123.8 (8)	N2—C8—C7^i	104.2 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1^ii	0.95	1.92	2.847 (8)	164

Symmetry code: (ii) −x+2, −y+2, −z+1.