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The title compound, C10H9N7O3, crystallizes with two independent mol­ecules in the asymmetric unit. The bond lengths and angles in both mol­ecules are within normal ranges. The dihedral angles between the mean planes of the pyridino[2,3-d]triazole and 1,3,5-triazine ring systems in the two mol­ecules are 75.2 (6) and 82.3 (6)°. The crystal packing is stabilized by π–π stacking inter­actions and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002996/cv6640sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002996/cv6640Isup2.hkl
Contains datablock I

CCDC reference: 298423

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.139
  • Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C18 .. 3.01 Ang.
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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-(4,6-Dimethoxy-1,3,5-triazin-2-yloxy)-1H-pyridino[2,3-d]triazole top
Crystal data top
C10H9N7O3Z = 4
Mr = 275.24F(000) = 568
Triclinic, P1Dx = 1.487 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7412 (19) ÅCell parameters from 1528 reflections
b = 10.530 (2) Åθ = 2.4–22.4°
c = 13.881 (3) ŵ = 0.12 mm1
α = 81.964 (3)°T = 298 K
β = 89.058 (3)°Block, colourless
γ = 76.467 (3)°0.40 × 0.38 × 0.28 mm
V = 1229.8 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4273 independent reflections
Radiation source: fine-focus sealed tube3416 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 109
Tmin = 0.955, Tmax = 0.968k = 128
6260 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0643P)2 + 0.1542P]
where P = (Fo2 + 2Fc2)/3
4273 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.37799 (19)0.44865 (16)0.84885 (13)0.0587 (5)
O20.1215 (2)0.85965 (16)0.87452 (14)0.0627 (5)
O30.6580 (2)0.74972 (19)0.89096 (15)0.0704 (5)
O40.30287 (19)0.27619 (15)0.56331 (12)0.0539 (4)
O50.0171 (2)0.64580 (16)0.63154 (15)0.0685 (5)
O60.1006 (2)0.28786 (17)0.86618 (13)0.0668 (5)
N10.5668 (3)0.4539 (2)0.66567 (16)0.0600 (6)
N20.7100 (3)0.1992 (2)0.85962 (16)0.0665 (6)
N30.5847 (3)0.2667 (2)0.89786 (16)0.0657 (6)
N40.5192 (2)0.36691 (18)0.83064 (15)0.0522 (5)
N50.2498 (2)0.65297 (19)0.86509 (15)0.0522 (5)
N60.3900 (2)0.81687 (19)0.87963 (13)0.0484 (5)
N70.5296 (2)0.5956 (2)0.87216 (15)0.0525 (5)
N80.1776 (2)0.0294 (2)0.57196 (16)0.0589 (6)
N90.5751 (2)0.0074 (2)0.64232 (16)0.0591 (6)
N100.5279 (2)0.1203 (2)0.62374 (16)0.0564 (6)
N110.3771 (2)0.14781 (18)0.59594 (14)0.0457 (5)
N120.1463 (2)0.46196 (18)0.59808 (15)0.0510 (5)
N130.0302 (2)0.47130 (18)0.75356 (16)0.0503 (5)
N140.2062 (2)0.27395 (17)0.71977 (14)0.0467 (5)
C10.7230 (3)0.2597 (2)0.76616 (18)0.0487 (6)
C20.8311 (3)0.2323 (3)0.6931 (2)0.0598 (7)
H2B0.91620.15950.70090.072*
C30.8043 (3)0.3188 (3)0.6094 (2)0.0637 (7)
H3B0.87440.30670.55850.076*
C40.6740 (3)0.4251 (3)0.5985 (2)0.0685 (8)
H4A0.66100.48040.53930.082*
C50.5993 (3)0.3682 (2)0.74659 (17)0.0440 (5)
C60.3898 (3)0.5737 (2)0.86318 (17)0.0472 (6)
C70.2598 (3)0.7752 (2)0.87333 (16)0.0477 (6)
C80.5198 (3)0.7221 (3)0.88086 (17)0.0499 (6)
C90.1225 (3)0.9943 (2)0.8837 (2)0.0758 (9)
H9B0.01621.04580.88390.114*
H9C0.17711.03000.82990.114*
H9D0.17480.99650.94350.114*
C100.6603 (4)0.8833 (3)0.9030 (3)0.0873 (10)
H10B0.76720.89010.90890.131*
H10C0.60430.90610.96050.131*
H10D0.61080.94260.84740.131*
C110.4507 (3)0.0615 (2)0.62583 (16)0.0435 (5)
C120.4345 (3)0.1907 (2)0.63291 (17)0.0552 (7)
H12B0.51750.26250.65260.066*
C130.2913 (3)0.2056 (3)0.60960 (19)0.0624 (7)
H13B0.27390.29000.61300.075*
C140.1685 (3)0.0958 (3)0.5803 (2)0.0685 (8)
H14B0.07200.11190.56540.082*
C150.3213 (3)0.0383 (2)0.59527 (15)0.0414 (5)
C160.2131 (3)0.3396 (2)0.63354 (17)0.0434 (5)
C170.0543 (3)0.5229 (2)0.6633 (2)0.0502 (6)
C180.1115 (3)0.3483 (2)0.77727 (18)0.0476 (6)
C190.1174 (3)0.7185 (3)0.6996 (3)0.0889 (11)
H19A0.16360.80610.66830.133*
H19B0.05570.72310.75500.133*
H19C0.19910.67430.72030.133*
C200.0084 (4)0.3641 (3)0.9347 (2)0.0903 (11)
H20A0.01000.30970.99640.135*
H20B0.09810.39570.91090.135*
H20C0.05220.43780.94240.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0530 (10)0.0490 (10)0.0779 (12)0.0137 (8)0.0164 (9)0.0206 (9)
O20.0565 (11)0.0479 (10)0.0800 (13)0.0046 (8)0.0030 (9)0.0092 (9)
O30.0569 (11)0.0819 (14)0.0868 (14)0.0307 (10)0.0089 (10)0.0369 (11)
O40.0644 (11)0.0397 (9)0.0540 (10)0.0053 (8)0.0170 (8)0.0083 (8)
O50.0575 (11)0.0415 (10)0.0975 (15)0.0038 (8)0.0051 (10)0.0057 (9)
O60.0964 (14)0.0523 (11)0.0552 (11)0.0213 (9)0.0284 (10)0.0167 (9)
N10.0681 (14)0.0519 (13)0.0554 (13)0.0108 (10)0.0010 (11)0.0034 (11)
N20.0712 (15)0.0567 (14)0.0605 (15)0.0004 (11)0.0063 (12)0.0044 (11)
N30.0787 (16)0.0608 (15)0.0509 (13)0.0101 (12)0.0026 (12)0.0043 (11)
N40.0587 (13)0.0419 (12)0.0521 (12)0.0044 (9)0.0076 (10)0.0068 (10)
N50.0473 (12)0.0475 (12)0.0636 (14)0.0126 (9)0.0086 (10)0.0119 (10)
N60.0565 (12)0.0512 (12)0.0404 (11)0.0175 (10)0.0048 (9)0.0089 (9)
N70.0493 (12)0.0563 (13)0.0559 (13)0.0148 (10)0.0085 (10)0.0183 (10)
N80.0472 (12)0.0581 (14)0.0722 (15)0.0139 (10)0.0025 (10)0.0091 (11)
N90.0471 (12)0.0578 (14)0.0707 (15)0.0060 (10)0.0077 (11)0.0125 (11)
N100.0456 (12)0.0586 (14)0.0686 (14)0.0140 (10)0.0030 (10)0.0182 (11)
N110.0427 (11)0.0389 (11)0.0554 (12)0.0058 (8)0.0076 (9)0.0131 (9)
N120.0473 (11)0.0384 (11)0.0636 (13)0.0054 (9)0.0091 (10)0.0031 (10)
N130.0449 (11)0.0412 (12)0.0692 (14)0.0124 (9)0.0132 (10)0.0201 (10)
N140.0549 (12)0.0364 (10)0.0508 (12)0.0125 (9)0.0129 (9)0.0112 (9)
C10.0502 (14)0.0448 (14)0.0519 (15)0.0116 (11)0.0042 (11)0.0083 (11)
C20.0470 (15)0.0618 (17)0.0740 (19)0.0104 (12)0.0009 (13)0.0250 (15)
C30.0610 (17)0.084 (2)0.0565 (17)0.0309 (15)0.0131 (13)0.0239 (15)
C40.078 (2)0.078 (2)0.0509 (16)0.0278 (16)0.0046 (15)0.0010 (14)
C50.0508 (13)0.0379 (13)0.0452 (13)0.0130 (10)0.0007 (11)0.0079 (10)
C60.0552 (15)0.0458 (14)0.0444 (13)0.0163 (11)0.0096 (11)0.0121 (11)
C70.0522 (15)0.0479 (14)0.0416 (13)0.0102 (11)0.0026 (11)0.0048 (11)
C80.0535 (15)0.0633 (17)0.0402 (13)0.0234 (13)0.0071 (11)0.0170 (12)
C90.081 (2)0.0472 (16)0.093 (2)0.0006 (14)0.0019 (17)0.0126 (15)
C100.086 (2)0.091 (2)0.107 (3)0.0486 (18)0.0055 (19)0.042 (2)
C110.0475 (13)0.0435 (13)0.0377 (12)0.0047 (10)0.0004 (10)0.0097 (10)
C120.0704 (17)0.0450 (14)0.0450 (14)0.0045 (12)0.0016 (12)0.0043 (11)
C130.084 (2)0.0470 (15)0.0602 (17)0.0251 (14)0.0031 (15)0.0060 (13)
C140.0645 (18)0.0680 (19)0.081 (2)0.0314 (15)0.0083 (15)0.0078 (15)
C150.0457 (13)0.0414 (13)0.0383 (12)0.0101 (10)0.0091 (10)0.0110 (10)
C160.0418 (12)0.0376 (13)0.0537 (14)0.0127 (10)0.0095 (10)0.0111 (11)
C170.0374 (13)0.0380 (13)0.0764 (18)0.0107 (10)0.0032 (12)0.0091 (12)
C180.0522 (14)0.0410 (14)0.0558 (15)0.0192 (11)0.0122 (11)0.0146 (11)
C190.0633 (19)0.0596 (19)0.132 (3)0.0157 (14)0.0124 (19)0.0268 (19)
C200.124 (3)0.084 (2)0.072 (2)0.029 (2)0.047 (2)0.0386 (18)
Geometric parameters (Å, º) top
O1—N41.372 (2)N12—C171.332 (3)
O1—C61.386 (3)N13—C181.322 (3)
O2—C71.324 (3)N13—C171.328 (3)
O2—C91.443 (3)N14—C161.304 (3)
O3—C81.321 (3)N14—C181.336 (3)
O3—C101.444 (3)C1—C51.375 (3)
O4—N111.372 (2)C1—C21.389 (3)
O4—C161.387 (3)C2—C31.359 (4)
O5—C171.315 (3)C2—H2B0.9300
O5—C191.451 (3)C3—C41.391 (4)
O6—C181.320 (3)C3—H3B0.9300
O6—C201.444 (3)C4—H4A0.9300
N1—C41.325 (3)C9—H9B0.9600
N1—C51.328 (3)C9—H9C0.9600
N2—N31.307 (3)C9—H9D0.9600
N2—C11.379 (3)C10—H10B0.9600
N3—N41.331 (3)C10—H10C0.9600
N4—C51.351 (3)C10—H10D0.9600
N5—C61.312 (3)C11—C151.378 (3)
N5—C71.331 (3)C11—C121.390 (3)
N6—C71.321 (3)C12—C131.347 (4)
N6—C81.322 (3)C12—H12B0.9300
N7—C61.307 (3)C13—C141.399 (4)
N7—C81.337 (3)C13—H13B0.9300
N8—C141.329 (3)C14—H14B0.9300
N8—C151.330 (3)C19—H19A0.9600
N9—N101.301 (3)C19—H19B0.9600
N9—C111.377 (3)C19—H19C0.9600
N10—N111.333 (3)C20—H20A0.9600
N11—C151.354 (3)C20—H20B0.9600
N12—C161.313 (3)C20—H20C0.9600
N4—O1—C6113.69 (18)O2—C9—H9B109.5
C7—O2—C9117.1 (2)O2—C9—H9C109.5
C8—O3—C10117.9 (2)H9B—C9—H9C109.5
N11—O4—C16113.48 (16)O2—C9—H9D109.5
C17—O5—C19116.9 (2)H9B—C9—H9D109.5
C18—O6—C20117.4 (2)H9C—C9—H9D109.5
C4—N1—C5111.4 (2)O3—C10—H10B109.5
N3—N2—C1108.1 (2)O3—C10—H10C109.5
N2—N3—N4107.2 (2)H10B—C10—H10C109.5
N3—N4—C5112.89 (19)O3—C10—H10D109.5
N3—N4—O1119.56 (19)H10B—C10—H10D109.5
C5—N4—O1127.33 (19)H10C—C10—H10D109.5
C6—N5—C7111.3 (2)N9—C11—C15109.2 (2)
C7—N6—C8113.5 (2)N9—C11—C12133.0 (2)
C6—N7—C8110.9 (2)C15—C11—C12117.8 (2)
C14—N8—C15110.9 (2)C13—C12—C11116.0 (2)
N10—N9—C11108.31 (19)C13—C12—H12B122.0
N9—N10—N11107.28 (19)C11—C12—H12B122.0
N10—N11—C15112.81 (18)C12—C13—C14120.8 (2)
N10—N11—O4118.89 (18)C12—C13—H13B119.6
C15—N11—O4127.96 (19)C14—C13—H13B119.6
C16—N12—C17111.4 (2)N8—C14—C13125.7 (3)
C18—N13—C17113.5 (2)N8—C14—H14B117.1
C16—N14—C18111.0 (2)C13—C14—H14B117.1
C5—C1—N2109.0 (2)N8—C15—N11128.8 (2)
C5—C1—C2117.7 (2)N8—C15—C11128.8 (2)
N2—C1—C2133.3 (2)N11—C15—C11102.4 (2)
C3—C2—C1115.6 (2)N14—C16—N12130.7 (2)
C3—C2—H2B122.2N14—C16—O4118.8 (2)
C1—C2—H2B122.2N12—C16—O4110.5 (2)
C2—C3—C4121.2 (3)O5—C17—N13119.5 (2)
C2—C3—H3B119.4O5—C17—N12114.1 (2)
C4—C3—H3B119.4N13—C17—N12126.4 (2)
N1—C4—C3125.2 (3)O6—C18—N13119.0 (2)
N1—C4—H4A117.4O6—C18—N14114.0 (2)
C3—C4—H4A117.4N13—C18—N14127.0 (2)
N1—C5—N4128.4 (2)O5—C19—H19A109.5
N1—C5—C1128.9 (2)O5—C19—H19B109.5
N4—C5—C1102.76 (19)H19A—C19—H19B109.5
N7—C6—N5130.5 (2)O5—C19—H19C109.5
N7—C6—O1118.7 (2)H19A—C19—H19C109.5
N5—C6—O1110.8 (2)H19B—C19—H19C109.5
N6—C7—O2119.5 (2)O6—C20—H20A109.5
N6—C7—N5126.7 (2)O6—C20—H20B109.5
O2—C7—N5113.8 (2)H20A—C20—H20B109.5
O3—C8—N6119.5 (2)O6—C20—H20C109.5
O3—C8—N7113.5 (2)H20A—C20—H20C109.5
N6—C8—N7127.0 (2)H20B—C20—H20C109.5
C1—N2—N3—N40.3 (3)C10—O3—C8—N7178.8 (2)
N2—N3—N4—C50.0 (3)C7—N6—C8—O3177.3 (2)
N2—N3—N4—O1175.0 (2)C7—N6—C8—N73.2 (3)
C6—O1—N4—N3109.2 (2)C6—N7—C8—O3179.5 (2)
C6—O1—N4—C576.6 (3)C6—N7—C8—N60.9 (3)
C11—N9—N10—N110.0 (3)N10—N9—C11—C150.3 (3)
N9—N10—N11—C150.2 (3)N10—N9—C11—C12179.3 (2)
N9—N10—N11—O4173.99 (18)N9—C11—C12—C13179.5 (3)
C16—O4—N11—N1098.7 (2)C15—C11—C12—C130.5 (3)
C16—O4—N11—C1588.6 (3)C11—C12—C13—C140.0 (4)
N3—N2—C1—C50.5 (3)C15—N8—C14—C130.1 (4)
N3—N2—C1—C2179.7 (3)C12—C13—C14—N80.3 (5)
C5—C1—C2—C31.4 (3)C14—N8—C15—N11180.0 (2)
N2—C1—C2—C3178.9 (3)C14—N8—C15—C110.8 (4)
C1—C2—C3—C41.6 (4)N10—N11—C15—N8179.7 (2)
C5—N1—C4—C30.4 (4)O4—N11—C15—N87.2 (4)
C2—C3—C4—N10.8 (5)N10—N11—C15—C110.3 (2)
C4—N1—C5—N4178.7 (2)O4—N11—C15—C11173.44 (19)
C4—N1—C5—C10.6 (4)N9—C11—C15—N8179.7 (2)
N3—N4—C5—N1179.7 (2)C12—C11—C15—N81.0 (4)
O1—N4—C5—N15.7 (4)N9—C11—C15—N110.3 (2)
N3—N4—C5—C10.3 (3)C12—C11—C15—N11179.6 (2)
O1—N4—C5—C1174.8 (2)C18—N14—C16—N121.4 (4)
N2—C1—C5—N1179.9 (2)C18—N14—C16—O4178.2 (2)
C2—C1—C5—N10.3 (4)C17—N12—C16—N142.2 (4)
N2—C1—C5—N40.5 (3)C17—N12—C16—O4177.40 (19)
C2—C1—C5—N4179.7 (2)N11—O4—C16—N140.8 (3)
C8—N7—C6—N52.7 (4)N11—O4—C16—N12179.54 (18)
C8—N7—C6—O1177.1 (2)C19—O5—C17—N131.0 (3)
C7—N5—C6—N73.3 (4)C19—O5—C17—N12179.1 (2)
C7—N5—C6—O1176.49 (19)C18—N13—C17—O5178.5 (2)
N4—O1—C6—N79.7 (3)C18—N13—C17—N121.6 (4)
N4—O1—C6—N5170.17 (18)C16—N12—C17—O5179.4 (2)
C8—N6—C7—O2177.9 (2)C16—N12—C17—N130.5 (4)
C8—N6—C7—N52.5 (3)C20—O6—C18—N134.5 (4)
C9—O2—C7—N60.6 (3)C20—O6—C18—N14176.1 (2)
C9—O2—C7—N5179.7 (2)C17—N13—C18—O6178.1 (2)
C6—N5—C7—N60.4 (3)C17—N13—C18—N142.6 (3)
C6—N5—C7—O2179.3 (2)C16—N14—C18—O6179.4 (2)
C10—O3—C8—N61.7 (4)C16—N14—C18—N131.3 (3)
 

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