4-Di­methyl­amino-6-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,5-triazine-2-amine di­methyl­form­amide solvate

The title compound, C₁₀H₁₃N₇O₂·C₃H₇NO, consisting of one mol­ecule of 4-di­methyl­amino-6-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,5-triazine-2-amine and one di­methyl­form­amide solvent mol­ecule, is a member of a new series of 4,6-di­amino­triazines. The triazine derivative mol­ecule, containing a pyrrole and a triazine ring, is essentially planar, with all the non-H atoms being in the same plane; π-conjugation is observed. An extensive network of hydrogen bonds (N—H...N and N—H...O) and π–π stacking interactions maintain the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.067
• wR factor = 0.143
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         N8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.

4-Dimethylamino-6-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,5-triazine-2-amine dimethylformamide solvate

Crystal data

C10H13N7O2·C3H7NO	F(000) = 1424
Mr = 336.37	Dx = 1.356 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 18161 reflections
a = 15.810 (3) Å	θ = 2.6–24.5°
b = 7.299 (2) Å	µ = 0.10 mm^−1
c = 28.550 (6) Å	T = 173 K
V = 3294.6 (12) Å^3	Pillar, colourless
Z = 8	0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	2905 independent reflections
Radiation source: fine-focus sealed tube	2217 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −18→18
Tmin = 0.970, Tmax = 0.980	k = −8→4
14666 measured reflections	l = −33→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0562P)^2] where P = (Fo^2 + 2Fc^2)/3
2905 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.62007 (16)	0.1932 (4)	0.31265 (11)	0.0381 (8)
H1A	0.6111	0.1106	0.2861	0.057*
H1B	0.6149	0.3205	0.3021	0.057*
H1C	0.5776	0.1686	0.3368	0.057*
C2	0.78395 (15)	0.1916 (4)	0.31093 (9)	0.0258 (6)
C3	0.84463 (18)	0.1432 (4)	0.34253 (9)	0.0305 (7)
H3	0.9041	0.1487	0.3379	0.037*
C4	0.80301 (18)	0.0843 (4)	0.38281 (9)	0.0318 (7)
C5	0.71725 (18)	0.0978 (4)	0.37558 (10)	0.0336 (7)
H5	0.6742	0.0665	0.3974	0.040*
C6	0.79611 (16)	0.2581 (3)	0.26292 (9)	0.0256 (6)
C7	0.88620 (16)	0.3339 (4)	0.20478 (9)	0.0276 (6)
C8	0.74578 (16)	0.3543 (4)	0.19328 (9)	0.0284 (6)
C9	0.59259 (16)	0.3597 (4)	0.18197 (11)	0.0436 (8)
H9A	0.5835	0.2270	0.1836	0.065*
H9B	0.5523	0.4136	0.1598	0.065*
H9C	0.5841	0.4137	0.2130	0.065*
C10	0.6897 (2)	0.4592 (5)	0.11834 (10)	0.0476 (9)
H10A	0.7450	0.5185	0.1151	0.071*
H10B	0.6450	0.5471	0.1106	0.071*
H10C	0.6865	0.3544	0.0970	0.071*
C11	0.97774 (19)	0.5928 (5)	0.06801 (10)	0.0440 (8)
H11	0.9925	0.7189	0.0674	0.053*
C12	0.8752 (2)	0.6699 (6)	0.00862 (12)	0.0776 (13)
H12A	0.8146	0.6719	0.0159	0.116*
H12B	0.8833	0.6327	−0.0241	0.116*
H12C	0.8991	0.7924	0.0133	0.116*
C13	0.8919 (2)	0.3509 (6)	0.03730 (14)	0.0783 (13)
H13A	0.8897	0.3105	0.0046	0.117*
H13B	0.8358	0.3376	0.0515	0.117*
H13C	0.9327	0.2758	0.0546	0.117*
N1	0.70544 (13)	0.1631 (3)	0.33216 (8)	0.0301 (6)
N2	0.84171 (18)	0.0130 (3)	0.42392 (9)	0.0439 (7)
N3	0.87698 (13)	0.2760 (3)	0.24960 (8)	0.0285 (6)
N4	0.96537 (13)	0.3498 (3)	0.18872 (8)	0.0352 (6)
H4A	0.9744	0.3868	0.1598	0.042*
H4B	1.0084	0.3233	0.2071	0.042*
N5	0.82337 (14)	0.3762 (3)	0.17528 (7)	0.0306 (6)
N6	0.72847 (13)	0.2928 (3)	0.23707 (8)	0.0291 (6)
N7	0.67880 (14)	0.3964 (3)	0.16616 (8)	0.0363 (6)
N8	0.91750 (15)	0.5408 (4)	0.03915 (8)	0.0427 (7)
O1	0.79633 (15)	−0.0292 (3)	0.45756 (8)	0.0619 (7)
O2	0.91967 (15)	−0.0028 (3)	0.42423 (8)	0.0585 (7)
O3	1.01650 (14)	0.4969 (3)	0.09527 (7)	0.0549 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0240 (15)	0.0416 (19)	0.0486 (19)	−0.0024 (14)	0.0048 (14)	−0.0071 (16)
C2	0.0239 (14)	0.0230 (15)	0.0306 (15)	−0.0025 (12)	0.0019 (12)	−0.0042 (13)
C3	0.0313 (16)	0.0280 (16)	0.0322 (15)	−0.0005 (13)	0.0041 (13)	−0.0027 (13)
C4	0.0390 (17)	0.0279 (17)	0.0286 (16)	0.0000 (14)	−0.0007 (13)	−0.0025 (13)
C5	0.0424 (18)	0.0275 (17)	0.0309 (16)	−0.0044 (14)	0.0119 (14)	−0.0010 (14)
C6	0.0265 (15)	0.0177 (14)	0.0326 (16)	−0.0009 (12)	0.0019 (13)	−0.0052 (12)
C7	0.0280 (15)	0.0261 (16)	0.0287 (15)	−0.0028 (13)	0.0034 (12)	−0.0037 (13)
C8	0.0293 (15)	0.0237 (15)	0.0321 (15)	−0.0010 (13)	−0.0033 (13)	−0.0035 (13)
C9	0.0292 (16)	0.045 (2)	0.057 (2)	0.0007 (15)	−0.0130 (15)	0.0009 (17)
C10	0.049 (2)	0.052 (2)	0.0428 (19)	0.0042 (17)	−0.0154 (15)	0.0020 (17)
C11	0.0414 (19)	0.059 (2)	0.0319 (17)	−0.0093 (17)	0.0039 (15)	−0.0020 (17)
C12	0.083 (3)	0.111 (4)	0.040 (2)	0.033 (3)	−0.012 (2)	−0.006 (2)
C13	0.076 (3)	0.082 (3)	0.077 (3)	−0.037 (2)	0.007 (2)	−0.013 (2)
N1	0.0308 (13)	0.0269 (13)	0.0327 (14)	−0.0029 (11)	0.0051 (10)	−0.0053 (11)
N2	0.0554 (18)	0.0352 (16)	0.0410 (16)	0.0006 (14)	−0.0020 (14)	0.0023 (13)
N3	0.0269 (13)	0.0308 (14)	0.0278 (13)	−0.0008 (11)	0.0021 (10)	−0.0021 (11)
N4	0.0292 (13)	0.0455 (16)	0.0308 (13)	−0.0003 (12)	0.0001 (11)	0.0066 (12)
N5	0.0313 (13)	0.0294 (14)	0.0310 (13)	−0.0023 (11)	−0.0027 (11)	−0.0003 (11)
N6	0.0262 (12)	0.0275 (13)	0.0337 (14)	−0.0014 (10)	−0.0006 (10)	−0.0005 (11)
N7	0.0315 (14)	0.0381 (15)	0.0394 (15)	−0.0023 (11)	−0.0091 (11)	0.0034 (12)
N8	0.0384 (15)	0.061 (2)	0.0286 (13)	−0.0056 (14)	−0.0064 (12)	−0.0026 (13)
O1	0.0750 (17)	0.0740 (18)	0.0367 (13)	−0.0099 (14)	0.0072 (12)	0.0170 (13)
O2	0.0563 (16)	0.0642 (17)	0.0549 (15)	0.0149 (14)	−0.0095 (12)	0.0121 (13)
O3	0.0498 (14)	0.0819 (19)	0.0331 (12)	−0.0004 (13)	−0.0078 (10)	0.0095 (13)

Geometric parameters (Å, º)

C1—N1	1.476 (3)	C9—H9A	0.9800
C1—H1A	0.9800	C9—H9B	0.9800
C1—H1B	0.9800	C9—H9C	0.9800
C1—H1C	0.9800	C10—N7	1.451 (4)
C2—C3	1.364 (4)	C10—H10A	0.9800
C2—N1	1.397 (3)	C10—H10B	0.9800
C2—C6	1.467 (4)	C10—H10C	0.9800
C3—C4	1.393 (4)	C11—O3	1.213 (3)
C3—H3	0.9500	C11—N8	1.315 (4)
C4—C5	1.375 (4)	C11—H11	0.9500
C4—N2	1.422 (4)	C12—N8	1.447 (4)
C5—N1	1.341 (3)	C12—H12A	0.9800
C5—H5	0.9500	C12—H12B	0.9800
C6—N6	1.324 (3)	C12—H12C	0.9800
C6—N3	1.340 (3)	C13—N8	1.445 (4)
C7—N4	1.338 (3)	C13—H13A	0.9800
C7—N5	1.338 (3)	C13—H13B	0.9800
C7—N3	1.355 (3)	C13—H13C	0.9800
C8—N5	1.340 (3)	N2—O1	1.238 (3)
C8—N7	1.347 (3)	N2—O2	1.238 (3)
C8—N6	1.356 (3)	N4—H4A	0.8800
C9—N7	1.461 (3)	N4—H4B	0.8800
N1—C1—H1A	109.5	N7—C10—H10C	109.5
N1—C1—H1B	109.5	H10A—C10—H10C	109.5
H1A—C1—H1B	109.5	H10B—C10—H10C	109.5
N1—C1—H1C	109.5	O3—C11—N8	127.0 (3)
H1A—C1—H1C	109.5	O3—C11—H11	116.5
H1B—C1—H1C	109.5	N8—C11—H11	116.5
C3—C2—N1	107.4 (2)	N8—C12—H12A	109.5
C3—C2—C6	127.7 (2)	N8—C12—H12B	109.5
N1—C2—C6	124.8 (2)	H12A—C12—H12B	109.5
C2—C3—C4	107.1 (2)	N8—C12—H12C	109.5
C2—C3—H3	126.5	H12A—C12—H12C	109.5
C4—C3—H3	126.5	H12B—C12—H12C	109.5
C5—C4—C3	108.7 (2)	N8—C13—H13A	109.5
C5—C4—N2	125.0 (3)	N8—C13—H13B	109.5
C3—C4—N2	126.2 (3)	H13A—C13—H13B	109.5
N1—C5—C4	107.5 (2)	N8—C13—H13C	109.5
N1—C5—H5	126.2	H13A—C13—H13C	109.5
C4—C5—H5	126.2	H13B—C13—H13C	109.5
N6—C6—N3	126.4 (2)	C5—N1—C2	109.3 (2)
N6—C6—C2	118.6 (2)	C5—N1—C1	121.9 (2)
N3—C6—C2	115.0 (2)	C2—N1—C1	128.8 (2)
N4—C7—N5	117.3 (2)	O1—N2—O2	123.3 (3)
N4—C7—N3	116.8 (2)	O1—N2—C4	118.8 (3)
N5—C7—N3	125.9 (2)	O2—N2—C4	117.9 (3)
N5—C8—N7	118.2 (2)	C6—N3—C7	113.6 (2)
N5—C8—N6	125.3 (2)	C7—N4—H4A	120.0
N7—C8—N6	116.5 (2)	C7—N4—H4B	120.0
N7—C9—H9A	109.5	H4A—N4—H4B	120.0
N7—C9—H9B	109.5	C7—N5—C8	114.3 (2)
H9A—C9—H9B	109.5	C6—N6—C8	114.5 (2)
N7—C9—H9C	109.5	C8—N7—C10	121.3 (2)
H9A—C9—H9C	109.5	C8—N7—C9	120.9 (2)
H9B—C9—H9C	109.5	C10—N7—C9	117.4 (2)
N7—C10—H10A	109.5	C11—N8—C13	120.2 (3)
N7—C10—H10B	109.5	C11—N8—C12	121.6 (3)
H10A—C10—H10B	109.5	C13—N8—C12	118.2 (3)
N1—C2—C3—C4	0.4 (3)	C3—C4—N2—O2	−1.6 (4)
C6—C2—C3—C4	−178.4 (3)	N6—C6—N3—C7	−0.8 (4)
C2—C3—C4—C5	−0.2 (3)	C2—C6—N3—C7	178.7 (2)
C2—C3—C4—N2	176.8 (3)	N4—C7—N3—C6	−178.2 (2)
C3—C4—C5—N1	0.0 (3)	N5—C7—N3—C6	1.8 (4)
N2—C4—C5—N1	−177.1 (3)	N4—C7—N5—C8	178.9 (2)
C3—C2—C6—N6	177.9 (3)	N3—C7—N5—C8	−1.0 (4)
N1—C2—C6—N6	−0.7 (4)	N7—C8—N5—C7	179.0 (2)
C3—C2—C6—N3	−1.6 (4)	N6—C8—N5—C7	−0.9 (4)
N1—C2—C6—N3	179.9 (2)	N3—C6—N6—C8	−0.8 (4)
C4—C5—N1—C2	0.2 (3)	C2—C6—N6—C8	179.7 (2)
C4—C5—N1—C1	179.5 (2)	N5—C8—N6—C6	1.8 (4)
C3—C2—N1—C5	−0.4 (3)	N7—C8—N6—C6	−178.2 (2)
C6—C2—N1—C5	178.4 (2)	N5—C8—N7—C10	1.6 (4)
C3—C2—N1—C1	−179.5 (2)	N6—C8—N7—C10	−178.5 (3)
C6—C2—N1—C1	−0.7 (4)	N5—C8—N7—C9	174.2 (2)
C5—C4—N2—O1	−5.4 (4)	N6—C8—N7—C9	−5.8 (4)
C3—C4—N2—O1	178.0 (3)	O3—C11—N8—C13	−0.8 (5)
C5—C4—N2—O2	175.0 (3)	O3—C11—N8—C12	179.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O3	0.88	2.12	2.987 (3)	170
N4—H4B···N3^i	0.88	2.22	3.099 (3)	175

Symmetry code: (i) −x+2, y, −z+1/2.