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

The title compound, C₁₆H₁₀N₄O₂, is an organic red pigment utilized for H₂ gas sensors. The asymmetric unit contains two half-molecules, each molecule being centrosymmetric. The two independent centrosymmetric diketopyrrolo­pyrrole moieties are connected by N—H...N hydrogen bonds to form a ribbon structure along [100]. The mol­ecules are stacked in a `hunter's fence' fashion (viz. when viewed from the side, molecles, slipped by about 70° within moleclar stacks, cross each other in a fence-like structure) along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.091
• wR factor = 0.346
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.90

Author Response: A two-dimensional detector (IP) was used for the collection of reflection data in combination with a 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:      0.292     0.835
            Tmin' and Tmax expected:      0.565     0.835
            RR' =      0.516
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.50

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.680
            Test value =      0.600
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           68.25
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               2028
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2242
           Completeness (_total/calc)             90.45%
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.346
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.90
PLAT084_ALERT_2_C High R2 Value ..................................       0.35
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.68 e/A   3
PLAT128_ALERT_4_C Non-standard setting of Space group P2/c    ....    P2/a
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   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.

(I)

Crystal data

C16H10N4O2	F(000) = 600.0
Mr = 290.28	Dx = 1.587 Mg m^−3
Monoclinic, P2/a	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ya	Cell parameters from 9840 reflections
a = 16.097 (2) Å	θ = 2.9–68.4°
b = 3.7144 (5) Å	µ = 0.90 mm^−1
c = 21.725 (2) Å	T = 93 K
β = 110.758 (7)°	Needle, red
V = 1214.6 (3) Å^3	0.60 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	1647 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.079
48 frames, δ ω = 15° scans	θmax = 68.3°
Absorption correction: multi-scan (Higashi, 1995)	h = −19→19
Tmin = 0.292, Tmax = 0.835	k = −3→3
9996 measured reflections	l = −25→25
2028 independent reflections

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.091	w = 1/[σ^2(Fo^2) + {0.149[Max(Fo^2,0) + 2Fc^2]/3}^2]
wR(F^2) = 0.346	(Δ/σ)max = 0.012
S = 1.91	Δρmax = 0.68 e Å^−3
2028 reflections	Δρmin = −0.47 e Å^−3
199 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	0.3542 (2)	1.025 (1)	0.3702 (2)	0.032 (1)
O2	0.4811 (2)	0.424 (1)	0.1304 (1)	0.031 (1)
N1	0.3669 (2)	1.183 (1)	0.4774 (2)	0.026 (1)
N2	0.3305 (3)	1.406 (1)	0.5887 (2)	0.028 (1)
N3	0.3900 (2)	0.305 (1)	0.0223 (2)	0.026 (1)
N4	0.2459 (3)	0.090 (1)	−0.0886 (2)	0.029 (1)
C1	0.4913 (3)	0.955 (1)	0.4665 (2)	0.023 (1)
C2	0.3987 (3)	1.048 (1)	0.4291 (2)	0.025 (1)
C3	0.4324 (3)	1.182 (1)	0.5392 (2)	0.026 (1)
C4	0.4156 (3)	1.325 (1)	0.5963 (2)	0.028 (1)
C5	0.4872 (3)	1.381 (2)	0.6553 (2)	0.031 (1)
C6	0.4700 (3)	1.523 (2)	0.7085 (2)	0.032 (1)
C7	0.3830 (3)	1.599 (2)	0.7016 (2)	0.029 (1)
C8	0.3163 (3)	1.538 (1)	0.6417 (2)	0.027 (1)
C9	0.5245 (3)	0.529 (1)	0.0340 (2)	0.023 (1)
C10	0.4685 (3)	0.422 (2)	0.0713 (2)	0.027 (1)
C11	0.3930 (3)	0.330 (1)	−0.0399 (2)	0.026 (1)
C12	0.3201 (3)	0.210 (1)	−0.0981 (2)	0.027 (1)
C13	0.3273 (3)	0.234 (2)	−0.1603 (2)	0.028 (1)
C14	0.2563 (3)	0.122 (2)	−0.2143 (2)	0.030 (1)
C15	0.1810 (3)	−0.004 (2)	−0.2048 (2)	0.030 (1)
C16	0.1797 (3)	−0.018 (1)	−0.1418 (2)	0.028 (1)
H1	0.3078	1.2646	0.4685	0.0317*
H2	0.3400	0.2166	0.0312	0.0317*
H3	0.5461	1.3231	0.6587	0.0372*
H4	0.5171	1.5674	0.7490	0.0380*
H5	0.3694	1.6907	0.7377	0.0346*
H6	0.2570	1.5937	0.6377	0.0325*
H7	0.3798	0.3253	−0.1652	0.0340*
H8	0.2591	0.1320	−0.2572	0.0363*
H9	0.1310	−0.0803	−0.2412	0.0360*
H10	0.1280	−0.1117	−0.1361	0.0335*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.027 (2)	0.037 (3)	0.028 (2)	0.001 (1)	0.007 (1)	0.000 (1)
O2	0.032 (2)	0.033 (3)	0.028 (2)	−0.004 (2)	0.011 (1)	0.001 (1)
N1	0.026 (2)	0.022 (3)	0.031 (2)	−0.001 (2)	0.010 (2)	0.001 (2)
N2	0.028 (2)	0.021 (3)	0.036 (2)	0.002 (2)	0.013 (2)	0.001 (2)
N3	0.025 (2)	0.020 (3)	0.034 (2)	−0.002 (2)	0.011 (2)	−0.000 (2)
N4	0.031 (2)	0.022 (3)	0.033 (2)	0.003 (2)	0.010 (2)	−0.001 (2)
C1	0.031 (2)	0.013 (3)	0.028 (2)	−0.004 (2)	0.014 (2)	0.002 (2)
C2	0.029 (2)	0.017 (3)	0.033 (2)	−0.000 (2)	0.013 (2)	0.000 (2)
C3	0.030 (2)	0.019 (3)	0.031 (2)	−0.001 (2)	0.011 (2)	0.004 (2)
C4	0.029 (2)	0.020 (4)	0.034 (2)	0.003 (2)	0.012 (2)	0.003 (2)
C5	0.029 (2)	0.032 (4)	0.034 (3)	−0.005 (2)	0.013 (2)	−0.000 (2)
C6	0.031 (3)	0.032 (4)	0.030 (2)	−0.001 (2)	0.008 (2)	−0.001 (2)
C7	0.035 (3)	0.020 (3)	0.036 (2)	−0.003 (2)	0.018 (2)	−0.001 (2)
C8	0.029 (2)	0.021 (3)	0.034 (2)	0.002 (2)	0.014 (2)	0.001 (2)
C9	0.025 (2)	0.016 (3)	0.029 (3)	0.003 (2)	0.010 (2)	−0.002 (2)
C10	0.025 (2)	0.025 (3)	0.031 (2)	0.001 (2)	0.010 (2)	−0.001 (2)
C11	0.031 (3)	0.012 (3)	0.034 (2)	0.005 (2)	0.012 (2)	0.000 (2)
C12	0.027 (2)	0.017 (3)	0.038 (3)	0.005 (2)	0.010 (2)	−0.000 (2)
C13	0.029 (2)	0.022 (3)	0.036 (2)	−0.001 (2)	0.014 (2)	−0.001 (2)
C14	0.031 (3)	0.028 (4)	0.033 (3)	0.002 (2)	0.012 (2)	−0.003 (2)
C15	0.025 (2)	0.028 (4)	0.035 (3)	−0.002 (2)	0.008 (2)	−0.005 (2)
C16	0.026 (2)	0.023 (3)	0.034 (3)	0.001 (2)	0.010 (2)	−0.002 (2)

Geometric parameters (Å, º)

O1—C2	1.228 (6)	C5—H3	0.950
O2—C10	1.226 (6)	C6—C7	1.383 (7)
N1—C2	1.412 (6)	C6—H4	0.950
N1—C3	1.383 (6)	C7—C8	1.382 (7)
N1—H1	0.950	C7—H5	0.950
N2—C4	1.355 (6)	C8—H6	0.950
N2—C8	1.344 (6)	C9—C9^ii	1.422 (8)
N3—C10	1.402 (6)	C9—C10	1.465 (6)
N3—C11	1.373 (6)	C9—C11^ii	1.390 (7)
N3—H2	0.950	C11—C12	1.457 (6)
N4—C12	1.357 (6)	C12—C13	1.399 (7)
N4—C16	1.327 (6)	C13—C14	1.381 (7)
C1—C1^i	1.420 (8)	C13—H7	0.950
C1—C2	1.464 (7)	C14—C15	1.381 (7)
C1—C3^i	1.375 (7)	C14—H8	0.950
C3—C4	1.460 (7)	C15—C16	1.378 (7)
C4—C5	1.402 (6)	C15—H9	0.950
C5—C6	1.385 (7)	C16—H10	0.950
O1···C8^iii	3.219 (6)	N3···C10^ix	3.540 (7)
O1···C14^iv	3.240 (6)	N3···C9^ix	3.557 (6)
O1···C8^v	3.275 (6)	N4···C12^ix	3.510 (7)
O1···C15^iv	3.434 (6)	N4···C16^viii	3.545 (7)
O1···C5^vi	3.562 (6)	N4···C11^ix	3.594 (6)
O2···C16^vii	3.148 (6)	C1···C3^vi	3.451 (7)
O2···C6^i	3.309 (6)	C1···C3^ix	3.562 (7)
O2···C16^iv	3.393 (6)	C1···C4^vi	3.565 (7)
O2···C7^i	3.529 (6)	C3···C4^ix	3.461 (7)
N1···N2^v	3.099 (6)	C5···C6^ix	3.435 (8)
N1···C8^v	3.424 (6)	C9···C11^x	3.442 (7)
N1···C2^viii	3.472 (7)	C11···C12^viii	3.551 (7)
N1···C1^viii	3.553 (6)	C12···C16^viii	3.564 (7)
N2···C8^ix	3.456 (7)	C13···C14^viii	3.551 (8)
N3···N4^vii	3.120 (6)	C13···C15^viii	3.587 (8)
N3···C16^vii	3.392 (6)	C14···C15^viii	3.495 (8)
C2—N1—C3	111.6 (4)	H5—C7—H6	95.8
C2—N1—H1	124.2	N2—C8—C7	123.8 (4)
C3—N1—H1	124.2	N2—C8—H6	118.1
C4—N2—C8	116.6 (4)	C7—C8—H6	118.1
C4—N2—H6	141.7	C9^ii—C9—C10	108.1 (5)
C10—N3—C11	113.0 (4)	C9^ii—C9—C11^ii	108.2 (5)
C10—N3—H2	123.5	C10—C9—C11^ii	143.6 (4)
C11—N3—H2	123.5	O2—C10—N3	124.6 (4)
C12—N4—C16	116.4 (4)	O2—C10—C9	132.2 (4)
C12—N4—H10	141.8	N3—C10—C9	103.2 (4)
C1^i—C1—C2	107.8 (5)	N3—C11—C9^ii	107.5 (4)
C1^i—C1—C3^i	108.8 (5)	N3—C11—C12	122.3 (4)
C2—C1—C3^i	143.4 (4)	C9^ii—C11—C12	130.2 (4)
O1—C2—N1	124.6 (4)	N4—C12—C11	116.7 (4)
O1—C2—C1	131.7 (4)	N4—C12—C13	123.2 (4)
N1—C2—C1	103.7 (4)	C11—C12—C13	120.1 (5)
N1—C3—C1^i	108.1 (4)	C12—C13—C14	118.3 (4)
N1—C3—C4	121.1 (4)	C12—C13—H7	120.9
C1^i—C3—C4	130.7 (4)	C14—C13—H7	120.9
N2—C4—C3	117.4 (4)	C13—C14—C15	118.8 (4)
N2—C4—C5	123.1 (5)	C13—C14—H8	120.6
C3—C4—C5	119.4 (4)	C15—C14—H8	120.6
C4—C5—C6	118.5 (4)	C14—C15—C16	119.0 (4)
C4—C5—H3	120.7	C14—C15—H9	120.5
C6—C5—H3	120.8	C14—C15—H10	143.7
C5—C6—C7	118.7 (4)	C16—C15—H9	120.5
C5—C6—H4	120.6	H9—C15—H10	95.8
C7—C6—H4	120.6	N4—C16—C15	124.3 (5)
C6—C7—C8	119.2 (4)	N4—C16—H10	117.9
C6—C7—H5	120.4	C15—C16—H10	117.8
C6—C7—H6	143.8	N2—H6—C7	74.1
C8—C7—H5	120.4	N4—H10—C15	74.2

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^v	0.95	2.19	3.099 (6)	159
N3—H2···N4^vii	0.95	2.22	3.120 (6)	159

Symmetry codes: (v) −x+1/2, y, −z+1; (vii) −x+1/2, y, −z.