Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400159X/cf6323sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680400159X/cf6323Isup2.hkl |
CCDC reference: 234915
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (Please check) = 0.000 Å
- R factor = 0.071
- wR factor = 0.204
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level A ATOM007_ALERT_1_A _atom_site_aniso_label is missing Unique label identifying the atom site. PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ..... = 20
Alert level B PLAT210_ALERT_3_B No Anisotropic ADP's Found in CIF .............. ? PLAT301_ALERT_3_B Main Residue Disorder ......................... 50.00 Perc.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 24 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.45 From the CIF: _reflns_number_total 1507 Count of symmetry unique reflns 1540 Completeness (_total/calc) 97.86% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
2 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: enCIFer (CCDC, 2003).
C14H14N4O2 | F(000) = 284 |
Mr = 270.29 | Dx = 1.409 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.590 (4) Å | Cell parameters from 2320 reflections |
b = 10.532 (6) Å | θ = 5.1–53.2° |
c = 8.101 (4) Å | µ = 0.10 mm−1 |
β = 100.248 (9)° | T = 150 K |
V = 637.3 (6) Å3 | Block, red |
Z = 2 | 0.43 × 0.42 × 0.19 mm |
Bruker SMART 1000 diffractometer | 1507 independent reflections |
Radiation source: fine-focus sealed tube | 1202 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 100 pixels mm-1 | θmax = 27.5°, θmin = 2.6° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | k = −13→13 |
Tmin = 0.959, Tmax = 0.982 | l = −10→10 |
6858 measured reflections |
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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.204 | H-atom parameters constrained |
S = 1.21 | w = 1/[σ2(Fo2) + (0.1146P)2 + 0.2904P] where P = (Fo2 + 2Fc2)/3 |
1183 reflections | (Δ/σ)max < 0.001 |
119 parameters | Δρmax = 0.37 e Å−3 |
86 restraints | Δρmin = −0.33 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 | Occ. (<1) | |
O1 | 0.0061 (7) | 0.2154 (6) | −0.1419 (7) | 0.0453 (15)* | 0.750 (5) |
O2 | 0.0563 (8) | 0.4133 (6) | −0.1875 (7) | 0.0375 (15)* | 0.750 (5) |
O1' | 0.043 (2) | 0.2321 (12) | −0.179 (2) | 0.039 (3)* | 0.250 (5) |
O2' | 0.099 (2) | 0.4343 (12) | −0.182 (2) | 0.037 (4)* | 0.250 (5) |
N1 | 0.4333 (6) | 0.2907 (6) | 0.6621 (6) | 0.0256 (11)* | 0.750 (5) |
N2 | 0.4342 (6) | 0.3848 (6) | 0.5666 (7) | 0.0269 (11)* | 0.750 (5) |
N3 | 0.7734 (7) | 0.3179 (6) | 1.3252 (6) | 0.0256 (12)* | 0.750 (5) |
N4 | 0.0665 (8) | 0.3200 (5) | −0.0958 (6) | 0.0270 (13)* | 0.750 (5) |
C1 | 0.1531 (8) | 0.3330 (6) | 0.0757 (4) | 0.0278 (11)* | 0.750 (5) |
C2 | 0.2433 (8) | 0.4456 (6) | 0.1240 (5) | 0.0286 (11)* | 0.750 (5) |
H2B | 0.2421 | 0.5126 | 0.0453 | 0.034* | 0.750 (5) |
C3 | 0.3351 (6) | 0.4601 (6) | 0.2874 (5) | 0.0280 (11)* | 0.750 (5) |
H3A | 0.3967 | 0.5371 | 0.3204 | 0.034* | 0.750 (5) |
C4 | 0.3367 (6) | 0.3621 (7) | 0.4024 (4) | 0.0278 (11)* | 0.750 (5) |
C5 | 0.2466 (6) | 0.2495 (6) | 0.3542 (5) | 0.0295 (12)* | 0.750 (5) |
H5A | 0.2477 | 0.1824 | 0.4328 | 0.035* | 0.750 (5) |
C6 | 0.1548 (7) | 0.2350 (6) | 0.1908 (5) | 0.0304 (11)* | 0.750 (5) |
H6A | 0.0932 | 0.1580 | 0.1578 | 0.037* | 0.750 (5) |
C7 | 0.5273 (6) | 0.3079 (5) | 0.8256 (4) | 0.0257 (11)* | 0.750 (5) |
C8 | 0.6257 (6) | 0.4151 (5) | 0.8843 (6) | 0.0248 (11)* | 0.750 (5) |
H8A | 0.6335 | 0.4844 | 0.8110 | 0.030* | 0.750 (5) |
C9 | 0.7127 (7) | 0.4208 (6) | 1.0503 (6) | 0.0256 (11)* | 0.750 (5) |
H9A | 0.7800 | 0.4941 | 1.0904 | 0.031* | 0.750 (5) |
C10 | 0.7013 (9) | 0.3194 (7) | 1.1576 (5) | 0.0244 (10)* | 0.750 (5) |
C11 | 0.6029 (9) | 0.2122 (6) | 1.0990 (6) | 0.0292 (11)* | 0.750 (5) |
H11A | 0.5951 | 0.1428 | 1.1723 | 0.035* | 0.750 (5) |
C12 | 0.5159 (7) | 0.2064 (5) | 0.9330 (6) | 0.0294 (11)* | 0.750 (5) |
H12A | 0.4486 | 0.1332 | 0.8929 | 0.035* | 0.750 (5) |
C13 | 0.8565 (9) | 0.4323 (7) | 1.4038 (8) | 0.0304 (17)* | 0.750 (5) |
H13A | 0.7744 | 0.5042 | 1.3767 | 0.046* | 0.750 (5) |
H13B | 0.9676 | 0.4493 | 1.3619 | 0.046* | 0.750 (5) |
H13C | 0.8835 | 0.4206 | 1.5257 | 0.046* | 0.750 (5) |
C14 | 0.7697 (11) | 0.2036 (8) | 1.4249 (10) | 0.0372 (18)* | 0.750 (5) |
H14A | 0.8119 | 0.1314 | 1.3663 | 0.056* | 0.750 (5) |
H14B | 0.6470 | 0.1875 | 1.4417 | 0.056* | 0.750 (5) |
H14C | 0.8478 | 0.2148 | 1.5340 | 0.056* | 0.750 (5) |
N1' | 0.4720 (18) | 0.3616 (15) | 0.6421 (17) | 0.0277 (18)* | 0.250 (5) |
N2' | 0.3756 (18) | 0.2716 (14) | 0.5709 (16) | 0.0264 (17)* | 0.250 (5) |
N3' | 0.810 (2) | 0.3319 (13) | 1.3125 (17) | 0.025 (2)* | 0.250 (5) |
N4' | 0.097 (2) | 0.3320 (10) | −0.1105 (16) | 0.026 (2)* | 0.250 (5) |
C1' | 0.161 (2) | 0.3322 (16) | 0.0630 (11) | 0.0289 (15)* | 0.250 (5) |
C2' | 0.259 (2) | 0.4299 (13) | 0.1506 (15) | 0.0299 (14)* | 0.250 (5) |
H2'B | 0.2775 | 0.5070 | 0.0950 | 0.036* | 0.250 (5) |
C3' | 0.3313 (18) | 0.4149 (13) | 0.3197 (15) | 0.0289 (15)* | 0.250 (5) |
H3'A | 0.3984 | 0.4817 | 0.3796 | 0.035* | 0.250 (5) |
C4' | 0.3048 (18) | 0.3021 (15) | 0.4010 (10) | 0.0293 (16)* | 0.250 (5) |
C5' | 0.2066 (18) | 0.2044 (13) | 0.3134 (15) | 0.0289 (16)* | 0.250 (5) |
H5'A | 0.1885 | 0.1273 | 0.3690 | 0.035* | 0.250 (5) |
C6' | 0.135 (2) | 0.2194 (14) | 0.1443 (15) | 0.0297 (16)* | 0.250 (5) |
H6'A | 0.0676 | 0.1526 | 0.0844 | 0.036* | 0.250 (5) |
C7' | 0.5515 (19) | 0.3374 (14) | 0.8102 (12) | 0.0254 (16)* | 0.250 (5) |
C8' | 0.6624 (19) | 0.4338 (12) | 0.8860 (17) | 0.0245 (15)* | 0.250 (5) |
H8'A | 0.6849 | 0.5061 | 0.8227 | 0.029* | 0.250 (5) |
C9' | 0.740 (2) | 0.4245 (17) | 1.0543 (18) | 0.0255 (14)* | 0.250 (5) |
H9'A | 0.8161 | 0.4904 | 1.1061 | 0.031* | 0.250 (5) |
C10' | 0.707 (3) | 0.319 (2) | 1.1469 (14) | 0.0266 (14)* | 0.250 (5) |
C11' | 0.597 (3) | 0.2223 (16) | 1.0712 (17) | 0.0277 (14)* | 0.250 (5) |
H11B | 0.5740 | 0.1500 | 1.1344 | 0.033* | 0.250 (5) |
C12' | 0.519 (2) | 0.2316 (13) | 0.9028 (16) | 0.0275 (15)* | 0.250 (5) |
H12B | 0.4428 | 0.1657 | 0.8511 | 0.033* | 0.250 (5) |
C13' | 0.883 (3) | 0.4539 (14) | 1.374 (3) | 0.029 (4)* | 0.250 (5) |
H13D | 0.9567 | 0.4429 | 1.4856 | 0.043* | 0.250 (5) |
H13E | 0.7855 | 0.5131 | 1.3813 | 0.043* | 0.250 (5) |
H13F | 0.9576 | 0.4878 | 1.2971 | 0.043* | 0.250 (5) |
C14' | 0.805 (3) | 0.2314 (19) | 1.434 (3) | 0.029 (4)* | 0.250 (5) |
H14D | 0.8403 | 0.2656 | 1.5479 | 0.044* | 0.250 (5) |
H14E | 0.8875 | 0.1636 | 1.4160 | 0.044* | 0.250 (5) |
H14F | 0.6830 | 0.1972 | 1.4214 | 0.044* | 0.250 (5) |
O1—N4 | 1.226 (4) | C14—H14B | 0.980 |
O2—N4 | 1.226 (4) | C14—H14C | 0.980 |
O1'—N4' | 1.226 (4) | N1'—N2' | 1.271 (15) |
O2'—N4' | 1.226 (4) | N1'—C7' | 1.412 (14) |
N1—N2 | 1.258 (6) | N2'—C4' | 1.422 (13) |
N1—C7 | 1.400 (5) | N3'—C10' | 1.432 (13) |
N2—C4 | 1.422 (6) | N3'—C14' | 1.453 (5) |
N3—C10 | 1.371 (5) | N3'—C13' | 1.453 (5) |
N3—C13 | 1.453 (5) | N4'—C1' | 1.403 (13) |
N3—C14 | 1.453 (5) | C1'—C2' | 1.390 |
N4—C1 | 1.434 (5) | C1'—C6' | 1.390 |
C1—C2 | 1.390 | C2'—C3' | 1.390 |
C1—C6 | 1.390 | C2'—H2'B | 0.950 |
C2—C3 | 1.390 | C3'—C4' | 1.390 |
C2—H2B | 0.950 | C3'—H3'A | 0.950 |
C3—C4 | 1.390 | C4'—C5' | 1.390 |
C3—H3A | 0.950 | C5'—C6' | 1.390 |
C4—C5 | 1.390 | C5'—H5'A | 0.950 |
C5—C6 | 1.390 | C6'—H6'A | 0.950 |
C5—H5A | 0.950 | C7'—C8' | 1.390 |
C6—H6A | 0.950 | C7'—C12' | 1.390 |
C7—C8 | 1.390 | C8'—C9' | 1.390 |
C7—C12 | 1.390 | C8'—H8'A | 0.950 |
C8—C9 | 1.390 | C9'—C10' | 1.390 |
C8—H8A | 0.950 | C9'—H9'A | 0.950 |
C9—C10 | 1.390 | C10'—C11' | 1.390 |
C9—H9A | 0.950 | C11'—C12' | 1.390 |
C10—C11 | 1.390 | C11'—H11B | 0.950 |
C11—C12 | 1.390 | C12'—H12B | 0.950 |
C11—H11A | 0.950 | C13'—H13D | 0.980 |
C12—H12A | 0.950 | C13'—H13E | 0.980 |
C13—H13A | 0.980 | C13'—H13F | 0.980 |
C13—H13B | 0.980 | C14'—H14D | 0.980 |
C13—H13C | 0.980 | C14'—H14E | 0.980 |
C14—H14A | 0.980 | C14'—H14F | 0.980 |
N2—N1—C7 | 115.0 (5) | O2'—N4'—C1' | 116.3 (13) |
N1—N2—C4 | 112.5 (4) | O1'—N4'—C1' | 119.0 (13) |
C10—N3—C13 | 119.4 (5) | C2'—C1'—C6' | 120.0 |
C10—N3—C14 | 121.0 (5) | C2'—C1'—N4' | 124.9 (11) |
C13—N3—C14 | 119.6 (5) | C6'—C1'—N4' | 114.8 (11) |
O2—N4—O1 | 123.7 (5) | C1'—C2'—C3' | 120.0 |
O2—N4—C1 | 118.6 (5) | C1'—C2'—H2'B | 120.0 |
O1—N4—C1 | 117.6 (4) | C3'—C2'—H2'B | 120.0 |
C2—C1—C6 | 120.0 | C2'—C3'—C4' | 120.0 |
C2—C1—N4 | 118.2 (3) | C2'—C3'—H3'A | 120.0 |
C6—C1—N4 | 121.8 (3) | C4'—C3'—H3'A | 120.0 |
C1—C2—C3 | 120.0 | C5'—C4'—C3' | 120.0 |
C1—C2—H2B | 120.0 | C5'—C4'—N2' | 113.8 (11) |
C3—C2—H2B | 120.0 | C3'—C4'—N2' | 126.2 (11) |
C2—C3—C4 | 120.0 | C6'—C5'—C4' | 120.0 |
C2—C3—H3A | 120.0 | C6'—C5'—H5'A | 120.0 |
C4—C3—H3A | 120.0 | C4'—C5'—H5'A | 120.0 |
C5—C4—C3 | 120.0 | C5'—C6'—C1' | 120.0 |
C5—C4—N2 | 123.7 (3) | C5'—C6'—H6'A | 120.0 |
C3—C4—N2 | 116.3 (3) | C1'—C6'—H6'A | 120.0 |
C6—C5—C4 | 120.0 | C8'—C7'—C12' | 120.0 |
C6—C5—H5A | 120.0 | C8'—C7'—N1' | 114.5 (11) |
C4—C5—H5A | 120.0 | C12'—C7'—N1' | 125.3 (11) |
C5—C6—C1 | 120.0 | C7'—C8'—C9' | 120.0 |
C5—C6—H6A | 120.0 | C7'—C8'—H8'A | 120.0 |
C1—C6—H6A | 120.0 | C9'—C8'—H8'A | 120.0 |
C8—C7—C12 | 120.0 | C10'—C9'—C8' | 120.0 |
C8—C7—N1 | 125.5 (3) | C10'—C9'—H9'A | 120.0 |
C12—C7—N1 | 114.5 (3) | C8'—C9'—H9'A | 120.0 |
C7—C8—C9 | 120.0 | C9'—C10'—C11' | 120.0 |
C7—C8—H8A | 120.0 | C9'—C10'—N3' | 107.9 (13) |
C9—C8—H8A | 120.0 | C11'—C10'—N3' | 132.0 (13) |
C8—C9—C10 | 120.0 | C12'—C11'—C10' | 120.0 |
C8—C9—H9A | 120.0 | C12'—C11'—H11B | 120.0 |
C10—C9—H9A | 120.0 | C10'—C11'—H11B | 120.0 |
N3—C10—C11 | 115.2 (4) | C11'—C12'—C7' | 120.0 |
N3—C10—C9 | 124.7 (4) | C11'—C12'—H12B | 120.0 |
C11—C10—C9 | 120.0 | C7'—C12'—H12B | 120.0 |
C12—C11—C10 | 120.0 | N3'—C13'—H13D | 109.5 |
C12—C11—H11A | 120.0 | N3'—C13'—H13E | 109.5 |
C10—C11—H11A | 120.0 | H13D—C13'—H13E | 109.5 |
C11—C12—C7 | 120.0 | N3'—C13'—H13F | 109.5 |
C11—C12—H12A | 120.0 | H13D—C13'—H13F | 109.5 |
C7—C12—H12A | 120.0 | H13E—C13'—H13F | 109.5 |
N2'—N1'—C7' | 114.6 (14) | N3'—C14'—H14D | 109.5 |
N1'—N2'—C4' | 111.0 (13) | N3'—C14'—H14E | 109.5 |
C10'—N3'—C14' | 119.4 (15) | H14D—C14'—H14E | 109.5 |
C10'—N3'—C13' | 121.3 (15) | N3'—C14'—H14F | 109.5 |
C14'—N3'—C13' | 117.7 (16) | H14D—C14'—H14F | 109.5 |
O2'—N4'—O1' | 124.8 (15) | H14E—C14'—H14F | 109.5 |
C7—N1—N2—C4 | −180.0 (4) | C7'—N1'—N2'—C4' | −178.4 (13) |
O2—N4—C1—C2 | −8.9 (8) | O2'—N4'—C1'—C2' | −14 (3) |
O1—N4—C1—C2 | 171.4 (5) | O1'—N4'—C1'—C2' | 165.8 (15) |
O2—N4—C1—C6 | 173.8 (5) | O2'—N4'—C1'—C6' | 171.7 (15) |
O1—N4—C1—C6 | −5.9 (8) | O1'—N4'—C1'—C6' | −8 (2) |
C6—C1—C2—C3 | 0.0 | C6'—C1'—C2'—C3' | 0.0 |
N4—C1—C2—C3 | −177.4 (6) | N4'—C1'—C2'—C3' | −174 (2) |
C1—C2—C3—C4 | 0.0 | C1'—C2'—C3'—C4' | 0.0 |
C2—C3—C4—C5 | 0.0 | C2'—C3'—C4'—C5' | 0.0 |
C2—C3—C4—N2 | 179.9 (4) | C2'—C3'—C4'—N2' | 177.4 (15) |
N1—N2—C4—C5 | 1.6 (6) | N1'—N2'—C4'—C5' | 176.5 (11) |
N1—N2—C4—C3 | −178.3 (3) | N1'—N2'—C4'—C3' | −1.1 (18) |
C3—C4—C5—C6 | 0.0 | C3'—C4'—C5'—C6' | 0.0 |
N2—C4—C5—C6 | −179.8 (5) | N2'—C4'—C5'—C6' | −177.7 (13) |
C4—C5—C6—C1 | 0.0 | C4'—C5'—C6'—C1' | 0.0 |
C2—C1—C6—C5 | 0.0 | C2'—C1'—C6'—C5' | 0.0 |
N4—C1—C6—C5 | 177.3 (6) | N4'—C1'—C6'—C5' | 174.3 (18) |
N2—N1—C7—C8 | −3.6 (6) | N2'—N1'—C7'—C8' | 177.6 (12) |
N2—N1—C7—C12 | 176.1 (4) | N2'—N1'—C7'—C12' | −6.3 (19) |
C12—C7—C8—C9 | 0.0 | C12'—C7'—C8'—C9' | 0.0 |
N1—C7—C8—C9 | 179.7 (5) | N1'—C7'—C8'—C9' | 176.3 (15) |
C7—C8—C9—C10 | 0.0 | C7'—C8'—C9'—C10' | 0.0 |
C13—N3—C10—C11 | −171.3 (5) | C8'—C9'—C10'—C11' | 0.0 |
C14—N3—C10—C11 | 9.4 (8) | C8'—C9'—C10'—N3' | 177.6 (19) |
C13—N3—C10—C9 | 5.1 (9) | C14'—N3'—C10'—C9' | −177.8 (15) |
C14—N3—C10—C9 | −174.2 (5) | C13'—N3'—C10'—C9' | 17 (2) |
C8—C9—C10—N3 | −176.2 (7) | C14'—N3'—C10'—C11' | −1 (3) |
C8—C9—C10—C11 | 0.0 | C13'—N3'—C10'—C11' | −165.8 (15) |
N3—C10—C11—C12 | 176.6 (7) | C9'—C10'—C11'—C12' | 0.0 |
C9—C10—C11—C12 | 0.0 | N3'—C10'—C11'—C12' | −177 (2) |
C10—C11—C12—C7 | 0.0 | C10'—C11'—C12'—C7' | 0.0 |
C8—C7—C12—C11 | 0.0 | C8'—C7'—C12'—C11' | 0.0 |
N1—C7—C12—C11 | −179.7 (5) | N1'—C7'—C12'—C11' | −175.9 (17) |
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