Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601172X/sj2034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680601172X/sj2034Isup2.hkl |
CCDC reference: 608493
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.105
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C18 - C19 .. 8.80 su PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C7 .. 8.35 su
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.836 0.994 Tmin(prime) and Tmax expected: 0.972 0.994 RR(prime) = 0.860 Please check that your absorption correction is appropriate. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C14 .. 5.53 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 .. 6.40 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 5.57 su PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. O1 .. 2.61 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H14 N4 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C7 H9 N3 O
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 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 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: TEXSAN (Molecular Structure Corporation, 1998); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.
C13H14N4O·C7H9N3O | F(000) = 832 |
Mr = 393.45 | Dx = 1.308 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4516 reflections |
a = 14.0097 (9) Å | θ = 1.7–27.5° |
b = 5.8841 (3) Å | µ = 0.09 mm−1 |
c = 24.3124 (19) Å | T = 293 K |
β = 94.273 (3)° | Plate, colorless |
V = 1998.6 (2) Å3 | 0.32 × 0.17 × 0.07 mm |
Z = 4 |
Rigaku Weissenberg IP diffractometer | 4516 independent reflections |
Radiation source: fine-focus sealed tube | 1815 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (TEXSAN; Molecular Structure Corporation, 1998) | h = 0→18 |
Tmin = 0.836, Tmax = 0.994 | k = 0→7 |
18299 measured reflections | l = −31→31 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0229P)2] where P = (Fo2 + 2Fc2)/3 |
4516 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.18231 (12) | 0.2251 (3) | 0.20019 (6) | 0.0491 (5) | |
O2 | 0.02616 (11) | 0.3820 (3) | 0.06953 (6) | 0.0430 (4) | |
N1 | 0.25927 (14) | −0.3167 (4) | 0.15896 (8) | 0.0487 (6) | |
H1A | 0.2170 | −0.4093 | 0.1445 | 0.058* | |
N2 | 0.23432 (15) | −0.1370 (4) | 0.19223 (8) | 0.0546 (6) | |
H2B | 0.2441 | −0.1492 | 0.2275 | 0.065* | |
N3 | 0.17038 (14) | 0.0558 (4) | 0.11627 (7) | 0.0540 (6) | |
H3B | 0.1448 | 0.1746 | 0.1008 | 0.065* | |
H3C | 0.1801 | −0.0632 | 0.0969 | 0.065* | |
N4 | −0.03660 (14) | 0.7262 (4) | 0.04818 (8) | 0.0453 (5) | |
H4B | −0.0258 | 0.7065 | 0.0141 | 0.054* | |
N5 | −0.08227 (14) | 0.9266 (4) | 0.06360 (7) | 0.0441 (5) | |
H5B | −0.0556 | 1.0193 | 0.0874 | 0.053* | |
N6 | −0.02065 (13) | 0.6122 (4) | 0.13819 (7) | 0.0449 (5) | |
H6B | −0.0368 | 0.7478 | 0.1469 | 0.054* | |
N7 | −0.00711 (15) | 0.4499 (4) | 0.18007 (7) | 0.0468 (5) | |
H7A | 0.0437 | 0.4502 | 0.2023 | 0.056* | |
C1 | 0.35766 (18) | −0.3401 (5) | 0.14989 (10) | 0.0471 (7) | |
C2 | 0.3871 (2) | −0.5431 (5) | 0.12705 (11) | 0.0594 (8) | |
H2A | 0.3435 | −0.6606 | 0.1198 | 0.071* | |
C3 | 0.4823 (2) | −0.5686 (7) | 0.11514 (13) | 0.0765 (9) | |
H3A | 0.5021 | −0.7032 | 0.0995 | 0.092* | |
C4 | 0.5471 (2) | −0.3960 (8) | 0.12639 (14) | 0.0894 (12) | |
H4A | 0.6105 | −0.4126 | 0.1182 | 0.107* | |
C5 | 0.5172 (3) | −0.2002 (7) | 0.14975 (15) | 0.0846 (11) | |
H5A | 0.5612 | −0.0847 | 0.1580 | 0.102* | |
C6 | 0.4227 (2) | −0.1691 (5) | 0.16151 (11) | 0.0637 (8) | |
H6A | 0.4036 | −0.0338 | 0.1771 | 0.076* | |
C7 | 0.19515 (16) | 0.0561 (5) | 0.17061 (10) | 0.0425 (6) | |
C8 | −0.17498 (18) | 0.9673 (5) | 0.03769 (9) | 0.0424 (6) | |
C9 | −0.19680 (19) | 1.1785 (5) | 0.01570 (10) | 0.0523 (7) | |
H9A | −0.1500 | 1.2909 | 0.0167 | 0.063* | |
C10 | −0.2873 (2) | 1.2247 (5) | −0.00769 (11) | 0.0637 (8) | |
H10A | −0.3014 | 1.3684 | −0.0220 | 0.076* | |
C11 | −0.3570 (2) | 1.0599 (6) | −0.01004 (11) | 0.0666 (9) | |
H11A | −0.4182 | 1.0917 | −0.0256 | 0.080* | |
C12 | −0.3353 (2) | 0.8472 (6) | 0.01088 (12) | 0.0652 (8) | |
H12A | −0.3817 | 0.7339 | 0.0090 | 0.078* | |
C13 | −0.24452 (19) | 0.8014 (5) | 0.03467 (10) | 0.0544 (7) | |
H13A | −0.2303 | 0.6574 | 0.0487 | 0.065* | |
C14 | −0.00948 (16) | 0.5653 (5) | 0.08491 (9) | 0.0372 (6) | |
C15 | −0.07927 (17) | 0.2860 (4) | 0.18473 (9) | 0.0415 (6) | |
C16 | −0.17139 (18) | 0.3116 (5) | 0.16065 (9) | 0.0510 (7) | |
H16A | −0.1871 | 0.4388 | 0.1391 | 0.061* | |
C17 | −0.2402 (2) | 0.1477 (6) | 0.16860 (11) | 0.0616 (8) | |
H17A | −0.3017 | 0.1655 | 0.1519 | 0.074* | |
C18 | −0.2191 (2) | −0.0396 (6) | 0.20058 (11) | 0.0628 (8) | |
H18A | −0.2657 | −0.1484 | 0.2057 | 0.075* | |
C19 | −0.1278 (2) | −0.0647 (5) | 0.22503 (10) | 0.0601 (8) | |
H19A | −0.1134 | −0.1903 | 0.2473 | 0.072* | |
C20 | −0.05692 (18) | 0.0940 (5) | 0.21697 (9) | 0.0485 (7) | |
H20A | 0.0049 | 0.0728 | 0.2329 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0537 (11) | 0.0459 (11) | 0.0466 (10) | 0.0027 (9) | −0.0041 (8) | −0.0089 (9) |
O2 | 0.0526 (10) | 0.0346 (10) | 0.0414 (9) | 0.0103 (9) | 0.0012 (8) | −0.0026 (8) |
N1 | 0.0479 (14) | 0.0430 (13) | 0.0535 (12) | 0.0022 (11) | −0.0074 (10) | −0.0053 (12) |
N2 | 0.0748 (16) | 0.0472 (15) | 0.0403 (11) | 0.0122 (13) | −0.0044 (11) | 0.0016 (12) |
N3 | 0.0734 (15) | 0.0443 (14) | 0.0415 (11) | 0.0126 (12) | −0.0148 (11) | −0.0016 (11) |
N4 | 0.0578 (14) | 0.0424 (13) | 0.0362 (10) | 0.0141 (12) | 0.0072 (10) | 0.0036 (11) |
N5 | 0.0540 (13) | 0.0331 (12) | 0.0431 (11) | 0.0072 (11) | −0.0093 (10) | −0.0078 (10) |
N6 | 0.0632 (14) | 0.0361 (12) | 0.0362 (10) | 0.0034 (11) | 0.0075 (10) | −0.0006 (11) |
N7 | 0.0557 (13) | 0.0481 (13) | 0.0359 (10) | −0.0018 (12) | −0.0028 (9) | 0.0061 (11) |
C1 | 0.0483 (17) | 0.0428 (16) | 0.0485 (14) | 0.0034 (14) | −0.0071 (13) | 0.0146 (14) |
C2 | 0.0559 (18) | 0.0549 (19) | 0.0674 (18) | 0.0034 (16) | 0.0042 (15) | 0.0094 (17) |
C3 | 0.067 (2) | 0.080 (2) | 0.084 (2) | 0.021 (2) | 0.0164 (17) | 0.017 (2) |
C4 | 0.051 (2) | 0.116 (4) | 0.103 (3) | 0.006 (3) | 0.0108 (19) | 0.045 (3) |
C5 | 0.060 (2) | 0.077 (3) | 0.113 (3) | −0.014 (2) | −0.014 (2) | 0.031 (2) |
C6 | 0.063 (2) | 0.0509 (18) | 0.0745 (19) | −0.0062 (17) | −0.0135 (16) | 0.0181 (17) |
C7 | 0.0348 (14) | 0.0464 (16) | 0.0452 (14) | −0.0039 (13) | −0.0037 (11) | 0.0060 (15) |
C8 | 0.0479 (16) | 0.0420 (15) | 0.0375 (13) | 0.0030 (14) | 0.0035 (12) | −0.0014 (13) |
C9 | 0.0640 (19) | 0.0377 (16) | 0.0533 (15) | 0.0025 (15) | −0.0068 (14) | 0.0009 (14) |
C10 | 0.076 (2) | 0.0501 (18) | 0.0630 (17) | 0.0170 (18) | −0.0093 (16) | 0.0003 (16) |
C11 | 0.0558 (18) | 0.077 (2) | 0.0655 (18) | 0.0127 (19) | −0.0083 (15) | −0.0038 (19) |
C12 | 0.0509 (18) | 0.069 (2) | 0.0755 (19) | −0.0061 (17) | −0.0003 (15) | −0.0006 (18) |
C13 | 0.0587 (17) | 0.0436 (17) | 0.0605 (16) | −0.0020 (15) | 0.0015 (14) | 0.0061 (15) |
C14 | 0.0358 (14) | 0.0373 (15) | 0.0383 (13) | −0.0031 (12) | 0.0027 (10) | 0.0000 (13) |
C15 | 0.0465 (15) | 0.0449 (16) | 0.0340 (12) | 0.0026 (14) | 0.0079 (11) | −0.0030 (13) |
C16 | 0.0506 (16) | 0.0552 (18) | 0.0475 (14) | 0.0031 (15) | 0.0050 (12) | 0.0048 (14) |
C17 | 0.0543 (18) | 0.071 (2) | 0.0594 (17) | −0.0020 (17) | 0.0032 (14) | 0.0014 (18) |
C18 | 0.0545 (19) | 0.071 (2) | 0.0642 (18) | −0.0106 (17) | 0.0124 (15) | −0.0109 (18) |
C19 | 0.084 (2) | 0.0461 (17) | 0.0528 (16) | 0.0039 (18) | 0.0200 (15) | 0.0063 (15) |
C20 | 0.0535 (17) | 0.0505 (17) | 0.0424 (13) | 0.0009 (16) | 0.0095 (12) | 0.0019 (15) |
O1—C7 | 1.248 (3) | C4—H4A | 0.9300 |
O2—C14 | 1.257 (3) | C5—C6 | 1.387 (4) |
N1—N2 | 1.391 (3) | C5—H5A | 0.9300 |
N1—C1 | 1.419 (3) | C6—H6A | 0.9300 |
N1—H1A | 0.8600 | C8—C13 | 1.377 (3) |
N2—C7 | 1.351 (3) | C8—C9 | 1.378 (3) |
N2—H2B | 0.8600 | C9—C10 | 1.378 (4) |
N3—C7 | 1.341 (3) | C9—H9A | 0.9300 |
N3—H3B | 0.8600 | C10—C11 | 1.374 (4) |
N3—H3C | 0.8600 | C10—H10A | 0.9300 |
N4—C14 | 1.337 (3) | C11—C12 | 1.376 (4) |
N4—N5 | 1.406 (3) | C11—H11A | 0.9300 |
N4—H4B | 0.8600 | C12—C13 | 1.383 (4) |
N5—C8 | 1.421 (3) | C12—H12A | 0.9300 |
N5—H5B | 0.8600 | C13—H13A | 0.9300 |
N6—C14 | 1.345 (3) | C15—C16 | 1.385 (3) |
N6—N7 | 1.398 (3) | C15—C20 | 1.397 (3) |
N6—H6B | 0.8600 | C16—C17 | 1.388 (4) |
N7—C15 | 1.408 (3) | C16—H16A | 0.9300 |
N7—H7A | 0.8600 | C17—C18 | 1.369 (4) |
C1—C6 | 1.372 (4) | C17—H17A | 0.9300 |
C1—C2 | 1.392 (4) | C18—C19 | 1.378 (4) |
C2—C3 | 1.394 (4) | C18—H18A | 0.9300 |
C2—H2A | 0.9300 | C19—C20 | 1.388 (4) |
C3—C4 | 1.376 (5) | C19—H19A | 0.9300 |
C3—H3A | 0.9300 | C20—H20A | 0.9300 |
C4—C5 | 1.364 (5) | ||
N2—N1—C1 | 116.9 (2) | N3—C7—N2 | 116.7 (2) |
N2—N1—H1A | 121.5 | C13—C8—C9 | 118.9 (2) |
C1—N1—H1A | 121.5 | C13—C8—N5 | 121.6 (2) |
C7—N2—N1 | 121.67 (19) | C9—C8—N5 | 119.6 (2) |
C7—N2—H2B | 119.2 | C10—C9—C8 | 120.6 (3) |
N1—N2—H2B | 119.2 | C10—C9—H9A | 119.7 |
C7—N3—H3B | 120.0 | C8—C9—H9A | 119.7 |
C7—N3—H3C | 120.0 | C11—C10—C9 | 120.5 (3) |
H3B—N3—H3C | 120.0 | C11—C10—H10A | 119.8 |
C14—N4—N5 | 121.88 (19) | C9—C10—H10A | 119.8 |
C14—N4—H4B | 119.1 | C10—C11—C12 | 119.3 (3) |
N5—N4—H4B | 119.1 | C10—C11—H11A | 120.3 |
N4—N5—C8 | 116.27 (19) | C12—C11—H11A | 120.3 |
N4—N5—H5B | 121.9 | C11—C12—C13 | 120.1 (3) |
C8—N5—H5B | 121.9 | C11—C12—H12A | 119.9 |
C14—N6—N7 | 122.8 (2) | C13—C12—H12A | 119.9 |
C14—N6—H6B | 118.6 | C8—C13—C12 | 120.6 (3) |
N7—N6—H6B | 118.6 | C8—C13—H13A | 119.7 |
N6—N7—C15 | 117.85 (18) | C12—C13—H13A | 119.7 |
N6—N7—H7A | 121.1 | O2—C14—N4 | 120.5 (2) |
C15—N7—H7A | 121.1 | O2—C14—N6 | 122.7 (2) |
C6—C1—C2 | 120.0 (3) | N4—C14—N6 | 116.8 (2) |
C6—C1—N1 | 122.3 (3) | C16—C15—C20 | 119.2 (3) |
C2—C1—N1 | 117.7 (2) | C16—C15—N7 | 122.9 (2) |
C1—C2—C3 | 119.4 (3) | C20—C15—N7 | 117.8 (2) |
C1—C2—H2A | 120.3 | C15—C16—C17 | 120.1 (3) |
C3—C2—H2A | 120.3 | C15—C16—H16A | 120.0 |
C4—C3—C2 | 120.4 (3) | C17—C16—H16A | 120.0 |
C4—C3—H3A | 119.8 | C18—C17—C16 | 121.0 (3) |
C2—C3—H3A | 119.8 | C18—C17—H17A | 119.5 |
C5—C4—C3 | 119.2 (3) | C16—C17—H17A | 119.5 |
C5—C4—H4A | 120.4 | C17—C18—C19 | 119.1 (3) |
C3—C4—H4A | 120.4 | C17—C18—H18A | 120.5 |
C4—C5—C6 | 121.7 (3) | C19—C18—H18A | 120.5 |
C4—C5—H5A | 119.2 | C18—C19—C20 | 121.2 (3) |
C6—C5—H5A | 119.2 | C18—C19—H19A | 119.4 |
C1—C6—C5 | 119.3 (3) | C20—C19—H19A | 119.4 |
C1—C6—H6A | 120.3 | C19—C20—C15 | 119.4 (2) |
C5—C6—H6A | 120.3 | C19—C20—H20A | 120.3 |
O1—C7—N3 | 122.1 (2) | C15—C20—H20A | 120.3 |
O1—C7—N2 | 121.2 (2) | ||
C1—N1—N2—C7 | 101.7 (3) | C9—C10—C11—C12 | −0.5 (5) |
C14—N4—N5—C8 | −120.5 (2) | C10—C11—C12—C13 | 0.9 (5) |
C14—N6—N7—C15 | −75.9 (3) | C9—C8—C13—C12 | −1.2 (4) |
N2—N1—C1—C6 | −15.2 (3) | N5—C8—C13—C12 | 177.8 (2) |
N2—N1—C1—C2 | 166.5 (2) | C11—C12—C13—C8 | 0.0 (4) |
C6—C1—C2—C3 | −1.3 (4) | N5—N4—C14—O2 | 175.83 (19) |
N1—C1—C2—C3 | 177.1 (2) | N5—N4—C14—N6 | −5.4 (3) |
C1—C2—C3—C4 | 0.7 (4) | N7—N6—C14—O2 | −9.8 (3) |
C2—C3—C4—C5 | 0.5 (5) | N7—N6—C14—N4 | 171.5 (2) |
C3—C4—C5—C6 | −1.2 (5) | N6—N7—C15—C16 | −17.6 (3) |
C2—C1—C6—C5 | 0.7 (4) | N6—N7—C15—C20 | 164.9 (2) |
N1—C1—C6—C5 | −177.6 (2) | C20—C15—C16—C17 | −0.1 (4) |
C4—C5—C6—C1 | 0.6 (5) | N7—C15—C16—C17 | −177.5 (2) |
N1—N2—C7—O1 | −172.4 (2) | C15—C16—C17—C18 | 0.7 (4) |
N1—N2—C7—N3 | 8.1 (4) | C16—C17—C18—C19 | −0.1 (4) |
N4—N5—C8—C13 | 48.5 (3) | C17—C18—C19—C20 | −1.1 (4) |
N4—N5—C8—C9 | −132.5 (2) | C18—C19—C20—C15 | 1.8 (4) |
C13—C8—C9—C10 | 1.6 (4) | C16—C15—C20—C19 | −1.2 (4) |
N5—C8—C9—C10 | −177.5 (2) | N7—C15—C20—C19 | 176.4 (2) |
C8—C9—C10—C11 | −0.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O2 | 0.86 | 2.15 | 2.952 (2) | 154 |
N7—H7A···O1 | 0.86 | 2.35 | 2.973 (3) | 129 |
N1—H1A···O1i | 0.86 | 2.61 | 3.098 (3) | 117 |
N2—H2B···O1ii | 0.86 | 2.11 | 2.899 (2) | 153 |
N4—H4B···O2iii | 0.86 | 2.10 | 2.946 (2) | 168 |
N5—H5B···O2iv | 0.86 | 2.48 | 3.079 (3) | 128 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x, −y+1, −z; (iv) x, y+1, z. |
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