Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000991/rn6033sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000991/rn6033Isup2.hkl |
CCDC reference: 264072
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.076
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C13 .. 5.34 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C13 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C11 - C14 ... 1.43 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17 C9 -C10 -C13 -N2 -95.00 18.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18 C11 -C10 -C13 -N2 84.00 18.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 51 C12 -C11 -C14 -N3 100.00 33.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 52 C10 -C11 -C14 -N3 -79.00 33.00 1.555 1.555 1.555 1.555
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 26.99 From the CIF: _reflns_number_total 2244 Count of symmetry unique reflns 2324 Completeness (_total/calc) 96.56% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1999).
C25H13N3O2 | Dx = 1.292 Mg m−3 |
Mr = 387.38 | Melting point: 525 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 7142 reflections |
a = 12.2243 (6) Å | θ = 2.1–27.2° |
b = 19.1241 (10) Å | µ = 0.08 mm−1 |
c = 8.5207 (19) Å | T = 293 K |
V = 1992.0 (5) Å3 | Plate, colourless |
Z = 4 | 0.55 × 0.30 × 0.20 mm |
F(000) = 800 |
Stoe IPDS-2 diffractometer | 2244 independent reflections |
Radiation source: fine-focus sealed tube | 1413 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.0°, θmin = 2.1° |
rotation method scans | h = −8→15 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −24→24 |
Tmin = 0.970, Tmax = 0.983 | l = −10→10 |
8228 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0415P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.88 | (Δ/σ)max < 0.001 |
2244 reflections | Δρmax = 0.09 e Å−3 |
273 parameters | Δρmin = −0.09 e Å−3 |
2 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0149 (15) |
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 | ||
C12 | 0.4993 (2) | 0.68899 (11) | 0.5019 (3) | 0.0619 (6) | |
H12 | 0.4820 | 0.6509 | 0.4386 | 0.074* | |
N1 | 0.34455 (18) | 0.66043 (9) | 0.6681 (2) | 0.0649 (5) | |
C7 | 0.4341 (2) | 0.70452 (11) | 0.6314 (3) | 0.0595 (6) | |
C16 | 0.2251 (2) | 0.75986 (11) | 0.7514 (2) | 0.0599 (6) | |
C11 | 0.5894 (2) | 0.72968 (11) | 0.4667 (3) | 0.0632 (6) | |
O2 | 0.16612 (18) | 0.64382 (9) | 0.7250 (3) | 0.0913 (6) | |
C17 | 0.3024 (2) | 0.80266 (12) | 0.8281 (3) | 0.0639 (6) | |
C10 | 0.6147 (2) | 0.78795 (11) | 0.5581 (3) | 0.0627 (6) | |
C13 | 0.7062 (3) | 0.83128 (12) | 0.5167 (3) | 0.0738 (7) | |
C25 | 0.1238 (2) | 0.78684 (11) | 0.7240 (3) | 0.0637 (6) | |
H25 | 0.0720 | 0.7593 | 0.6734 | 0.076* | |
C19 | 0.1733 (2) | 0.89645 (12) | 0.8504 (3) | 0.0695 (6) | |
C8 | 0.4629 (2) | 0.76120 (12) | 0.7229 (3) | 0.0626 (6) | |
C15 | 0.2429 (2) | 0.68416 (11) | 0.7144 (3) | 0.0669 (6) | |
C9 | 0.5506 (2) | 0.80319 (12) | 0.6863 (3) | 0.0668 (6) | |
H9 | 0.5665 | 0.8419 | 0.7483 | 0.080* | |
C24 | 0.0949 (2) | 0.85553 (12) | 0.7700 (3) | 0.0645 (6) | |
C18 | 0.2779 (2) | 0.86782 (12) | 0.8786 (3) | 0.0740 (7) | |
H18 | 0.3302 | 0.8939 | 0.9321 | 0.089* | |
C1 | 0.3607 (3) | 0.58659 (12) | 0.6425 (3) | 0.0730 (7) | |
C14 | 0.6562 (3) | 0.71238 (13) | 0.3345 (4) | 0.0864 (9) | |
N2 | 0.7784 (2) | 0.86647 (11) | 0.4820 (4) | 0.0961 (8) | |
C23 | −0.0091 (2) | 0.88415 (13) | 0.7387 (4) | 0.0806 (7) | |
H23 | −0.0610 | 0.8580 | 0.6846 | 0.097* | |
C2 | 0.4482 (3) | 0.55461 (14) | 0.7153 (4) | 0.0952 (10) | |
H2 | 0.4926 | 0.5802 | 0.7828 | 0.114* | |
C22 | −0.0335 (3) | 0.94998 (15) | 0.7875 (4) | 0.0965 (10) | |
H22 | −0.1022 | 0.9686 | 0.7663 | 0.116* | |
C20 | 0.1438 (3) | 0.96458 (13) | 0.9002 (4) | 0.0914 (9) | |
H20 | 0.1941 | 0.9919 | 0.9545 | 0.110* | |
N3 | 0.7090 (3) | 0.69908 (16) | 0.2281 (4) | 0.1418 (15) | |
C6 | 0.2932 (3) | 0.54919 (13) | 0.5428 (4) | 0.0915 (9) | |
H6 | 0.2350 | 0.5708 | 0.4919 | 0.110* | |
C21 | 0.0434 (3) | 0.99005 (16) | 0.8694 (4) | 0.1028 (10) | |
H21 | 0.0250 | 1.0348 | 0.9029 | 0.123* | |
C4 | 0.4049 (6) | 0.4474 (2) | 0.5946 (7) | 0.148 (2) | |
H4 | 0.4199 | 0.4003 | 0.5786 | 0.177* | |
C3 | 0.4701 (5) | 0.48534 (18) | 0.6888 (5) | 0.1291 (17) | |
H3 | 0.5304 | 0.4645 | 0.7362 | 0.155* | |
C5 | 0.3149 (5) | 0.47804 (19) | 0.5206 (5) | 0.1319 (17) | |
H5 | 0.2695 | 0.4512 | 0.4568 | 0.158* | |
O1 | 0.40624 (15) | 0.77569 (9) | 0.85941 (18) | 0.0753 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C12 | 0.0604 (17) | 0.0629 (12) | 0.0624 (13) | −0.0066 (11) | −0.0017 (11) | 0.0017 (10) |
N1 | 0.0616 (15) | 0.0625 (11) | 0.0707 (12) | −0.0036 (10) | 0.0108 (10) | 0.0079 (9) |
C7 | 0.0534 (16) | 0.0641 (12) | 0.0611 (13) | −0.0017 (11) | −0.0042 (11) | 0.0060 (10) |
C16 | 0.0546 (16) | 0.0695 (12) | 0.0557 (12) | −0.0062 (11) | 0.0017 (11) | 0.0066 (10) |
C11 | 0.0582 (17) | 0.0669 (13) | 0.0645 (13) | −0.0057 (11) | −0.0015 (12) | 0.0021 (11) |
O2 | 0.0726 (15) | 0.0720 (9) | 0.1294 (16) | −0.0179 (10) | 0.0271 (12) | 0.0000 (10) |
C17 | 0.0527 (17) | 0.0807 (14) | 0.0583 (13) | 0.0028 (12) | −0.0011 (11) | 0.0031 (11) |
C10 | 0.0481 (16) | 0.0650 (13) | 0.0751 (14) | −0.0047 (11) | −0.0096 (12) | 0.0011 (11) |
C13 | 0.062 (2) | 0.0699 (14) | 0.0892 (19) | −0.0042 (14) | −0.0091 (14) | −0.0028 (13) |
C25 | 0.0566 (17) | 0.0712 (14) | 0.0631 (13) | −0.0122 (11) | −0.0017 (11) | 0.0078 (11) |
C19 | 0.0661 (18) | 0.0723 (14) | 0.0700 (14) | −0.0003 (13) | 0.0040 (13) | 0.0006 (11) |
C8 | 0.0531 (16) | 0.0796 (13) | 0.0549 (12) | 0.0029 (12) | −0.0049 (11) | −0.0043 (12) |
C15 | 0.0628 (18) | 0.0674 (12) | 0.0705 (14) | −0.0057 (13) | 0.0066 (12) | 0.0080 (12) |
C9 | 0.0546 (18) | 0.0726 (14) | 0.0732 (15) | 0.0009 (12) | −0.0151 (12) | −0.0087 (11) |
C24 | 0.0572 (16) | 0.0730 (13) | 0.0633 (13) | −0.0036 (12) | 0.0026 (12) | 0.0136 (11) |
C18 | 0.069 (2) | 0.0799 (15) | 0.0726 (15) | −0.0059 (13) | 0.0004 (13) | −0.0124 (12) |
C1 | 0.084 (2) | 0.0607 (13) | 0.0742 (15) | −0.0054 (14) | 0.0231 (14) | 0.0085 (12) |
C14 | 0.089 (2) | 0.0814 (17) | 0.0885 (19) | −0.0316 (15) | 0.0240 (17) | −0.0113 (14) |
N2 | 0.0702 (19) | 0.0914 (14) | 0.127 (2) | −0.0212 (13) | −0.0069 (16) | 0.0027 (14) |
C23 | 0.0655 (19) | 0.0878 (16) | 0.0886 (18) | 0.0038 (14) | −0.0034 (15) | 0.0153 (15) |
C2 | 0.109 (3) | 0.0810 (16) | 0.096 (2) | 0.0181 (17) | 0.0145 (18) | 0.0225 (15) |
C22 | 0.085 (3) | 0.0926 (18) | 0.112 (2) | 0.0213 (18) | 0.0032 (18) | 0.0180 (18) |
C20 | 0.089 (3) | 0.0770 (16) | 0.108 (2) | 0.0030 (16) | 0.0045 (18) | −0.0123 (15) |
N3 | 0.153 (3) | 0.133 (2) | 0.139 (2) | −0.070 (2) | 0.081 (3) | −0.050 (2) |
C6 | 0.096 (3) | 0.0764 (16) | 0.103 (2) | −0.0191 (15) | 0.0226 (18) | −0.0051 (15) |
C21 | 0.099 (3) | 0.0806 (17) | 0.129 (3) | 0.0180 (18) | 0.002 (2) | −0.0009 (17) |
C4 | 0.195 (6) | 0.071 (2) | 0.177 (4) | 0.007 (3) | 0.095 (4) | 0.017 (2) |
C3 | 0.168 (5) | 0.081 (2) | 0.138 (3) | 0.035 (2) | 0.052 (3) | 0.034 (2) |
C5 | 0.164 (5) | 0.084 (2) | 0.148 (4) | −0.041 (2) | 0.058 (3) | −0.031 (2) |
O1 | 0.0582 (12) | 0.1086 (12) | 0.0591 (9) | 0.0091 (9) | −0.0077 (8) | −0.0115 (8) |
C12—C11 | 1.381 (3) | C8—O1 | 1.382 (3) |
C12—C7 | 1.393 (3) | C9—H9 | 0.9300 |
C12—H12 | 0.9300 | C24—C23 | 1.410 (4) |
N1—C15 | 1.380 (3) | C18—H18 | 0.9300 |
N1—C7 | 1.417 (3) | C1—C2 | 1.379 (5) |
N1—C1 | 1.443 (3) | C1—C6 | 1.384 (5) |
C7—C8 | 1.381 (3) | C14—N3 | 1.141 (4) |
C16—C25 | 1.362 (3) | C23—C22 | 1.359 (4) |
C16—C17 | 1.411 (3) | C23—H23 | 0.9300 |
C16—C15 | 1.497 (3) | C2—C3 | 1.370 (4) |
C11—C10 | 1.394 (3) | C2—H2 | 0.9300 |
C11—C14 | 1.430 (4) | C22—C21 | 1.400 (5) |
O2—C15 | 1.219 (3) | C22—H22 | 0.9300 |
C17—C18 | 1.352 (3) | C20—C21 | 1.346 (4) |
C17—O1 | 1.395 (3) | C20—H20 | 0.9300 |
C10—C9 | 1.376 (4) | C6—C5 | 1.399 (5) |
C10—C13 | 1.436 (4) | C6—H6 | 0.9300 |
C13—N2 | 1.149 (3) | C21—H21 | 0.9300 |
C25—C24 | 1.416 (3) | C4—C3 | 1.343 (8) |
C25—H25 | 0.9300 | C4—C5 | 1.398 (8) |
C19—C18 | 1.412 (4) | C4—H4 | 0.9300 |
C19—C24 | 1.414 (4) | C3—H3 | 0.9300 |
C19—C20 | 1.417 (4) | C5—H5 | 0.9300 |
C8—C9 | 1.375 (3) | ||
C11—C12—C7 | 120.5 (2) | C23—C24—C25 | 122.2 (2) |
C11—C12—H12 | 119.7 | C19—C24—C25 | 118.6 (2) |
C7—C12—H12 | 119.7 | C17—C18—C19 | 120.3 (3) |
C15—N1—C7 | 124.25 (18) | C17—C18—H18 | 119.9 |
C15—N1—C1 | 119.3 (2) | C19—C18—H18 | 119.9 |
C7—N1—C1 | 116.3 (2) | C2—C1—C6 | 120.6 (2) |
C8—C7—C12 | 118.0 (2) | C2—C1—N1 | 118.2 (3) |
C8—C7—N1 | 122.7 (2) | C6—C1—N1 | 121.1 (3) |
C12—C7—N1 | 119.3 (2) | N3—C14—C11 | 179.3 (5) |
C25—C16—C17 | 118.0 (2) | C22—C23—C24 | 120.0 (3) |
C25—C16—C15 | 117.5 (2) | C22—C23—H23 | 120.0 |
C17—C16—C15 | 124.1 (2) | C24—C23—H23 | 120.0 |
C12—C11—C10 | 120.4 (2) | C3—C2—C1 | 120.4 (4) |
C12—C11—C14 | 119.7 (2) | C3—C2—H2 | 119.8 |
C10—C11—C14 | 119.8 (2) | C1—C2—H2 | 119.8 |
C18—C17—O1 | 118.8 (2) | C23—C22—C21 | 120.8 (3) |
C18—C17—C16 | 122.3 (2) | C23—C22—H22 | 119.6 |
O1—C17—C16 | 118.9 (2) | C21—C22—H22 | 119.6 |
C9—C10—C11 | 119.1 (2) | C21—C20—C19 | 120.5 (3) |
C9—C10—C13 | 121.1 (2) | C21—C20—H20 | 119.8 |
C11—C10—C13 | 119.8 (2) | C19—C20—H20 | 119.8 |
N2—C13—C10 | 179.0 (3) | C1—C6—C5 | 118.2 (4) |
C16—C25—C24 | 122.1 (2) | C1—C6—H6 | 120.9 |
C16—C25—H25 | 119.0 | C5—C6—H6 | 120.9 |
C24—C25—H25 | 119.0 | C20—C21—C22 | 120.8 (3) |
C18—C19—C24 | 118.8 (2) | C20—C21—H21 | 119.6 |
C18—C19—C20 | 122.4 (3) | C22—C21—H21 | 119.6 |
C24—C19—C20 | 118.8 (3) | C3—C4—C5 | 120.7 (4) |
C9—C8—C7 | 122.0 (2) | C3—C4—H4 | 119.7 |
C9—C8—O1 | 117.7 (2) | C5—C4—H4 | 119.7 |
C7—C8—O1 | 120.3 (2) | C4—C3—C2 | 120.3 (5) |
O2—C15—N1 | 120.4 (2) | C4—C3—H3 | 119.8 |
O2—C15—C16 | 119.0 (2) | C2—C3—H3 | 119.8 |
N1—C15—C16 | 120.6 (2) | C4—C5—C6 | 119.7 (5) |
C8—C9—C10 | 120.0 (2) | C4—C5—H5 | 120.1 |
C8—C9—H9 | 120.0 | C6—C5—H5 | 120.1 |
C10—C9—H9 | 120.0 | C8—O1—C17 | 111.68 (18) |
C23—C24—C19 | 119.2 (2) | ||
C11—C12—C7—C8 | −0.4 (3) | C18—C19—C24—C23 | −178.8 (2) |
C11—C12—C7—N1 | −177.7 (2) | C20—C19—C24—C23 | 1.4 (3) |
C15—N1—C7—C8 | 44.8 (3) | C18—C19—C24—C25 | 1.3 (3) |
C1—N1—C7—C8 | −140.2 (2) | C20—C19—C24—C25 | −178.4 (2) |
C15—N1—C7—C12 | −138.0 (2) | C16—C25—C24—C23 | 178.6 (2) |
C1—N1—C7—C12 | 37.0 (3) | C16—C25—C24—C19 | −1.6 (3) |
C7—C12—C11—C10 | −1.7 (4) | O1—C17—C18—C19 | −179.4 (2) |
C7—C12—C11—C14 | 179.2 (3) | C16—C17—C18—C19 | −2.3 (4) |
C25—C16—C17—C18 | 2.1 (3) | C24—C19—C18—C17 | 0.6 (4) |
C15—C16—C17—C18 | −170.7 (2) | C20—C19—C18—C17 | −179.7 (2) |
C25—C16—C17—O1 | 179.1 (2) | C15—N1—C1—C2 | −129.0 (3) |
C15—C16—C17—O1 | 6.3 (3) | C7—N1—C1—C2 | 55.7 (3) |
C12—C11—C10—C9 | 1.8 (3) | C15—N1—C1—C6 | 53.5 (3) |
C14—C11—C10—C9 | −179.0 (3) | C7—N1—C1—C6 | −121.7 (3) |
C12—C11—C10—C13 | −177.6 (2) | C12—C11—C14—N3 | 100 (33) |
C14—C11—C10—C13 | 1.5 (4) | C10—C11—C14—N3 | −79 (33) |
C9—C10—C13—N2 | −95 (18) | C19—C24—C23—C22 | −0.9 (4) |
C11—C10—C13—N2 | 84 (18) | C25—C24—C23—C22 | 178.9 (2) |
C17—C16—C25—C24 | 0.0 (3) | C6—C1—C2—C3 | 0.6 (4) |
C15—C16—C25—C24 | 173.2 (2) | N1—C1—C2—C3 | −176.9 (3) |
C12—C7—C8—C9 | 2.3 (3) | C24—C23—C22—C21 | −0.2 (5) |
N1—C7—C8—C9 | 179.5 (2) | C18—C19—C20—C21 | 179.3 (3) |
C12—C7—C8—O1 | −175.0 (2) | C24—C19—C20—C21 | −0.9 (4) |
N1—C7—C8—O1 | 2.2 (3) | C2—C1—C6—C5 | 1.3 (4) |
C7—N1—C15—O2 | 170.8 (2) | N1—C1—C6—C5 | 178.6 (3) |
C1—N1—C15—O2 | −4.1 (4) | C19—C20—C21—C22 | −0.1 (5) |
C7—N1—C15—C16 | −8.9 (3) | C23—C22—C21—C20 | 0.7 (5) |
C1—N1—C15—C16 | 176.3 (2) | C5—C4—C3—C2 | 0.9 (7) |
C25—C16—C15—O2 | −30.0 (3) | C1—C2—C3—C4 | −1.7 (6) |
C17—C16—C15—O2 | 142.8 (3) | C3—C4—C5—C6 | 1.0 (7) |
C25—C16—C15—N1 | 149.7 (2) | C1—C6—C5—C4 | −2.0 (5) |
C17—C16—C15—N1 | −37.5 (3) | C9—C8—O1—C17 | 109.7 (2) |
C7—C8—C9—C10 | −2.2 (3) | C7—C8—O1—C17 | −72.9 (3) |
O1—C8—C9—C10 | 175.2 (2) | C18—C17—O1—C8 | −118.3 (2) |
C11—C10—C9—C8 | 0.0 (3) | C16—C17—O1—C8 | 64.6 (3) |
C13—C10—C9—C8 | 179.5 (2) |