Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019184/wn6182sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019184/wn6182Isup2.hkl |
CCDC reference: 225703
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.048
- wR factor = 0.120
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.684 0.998 Tmin' and Tmax expected: 0.959 0.998 RR' = 0.713 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.71
Alert level C PLAT024_ALERT_4_C Merging of Friedel Data Preferred for Z<=Si .... ! PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases. From the CIF: _diffrn_reflns_theta_max 25.10 From the CIF: _reflns_number_total 1607 Count of symmetry unique reflns 973 Completeness (_total/calc) 165.16% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 634 Fraction of Friedel pairs measured 0.652 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C20H22N4O2 | Dx = 1.239 Mg m−3 |
Mr = 350.41 | Melting point: 146-147 oC K |
Orthorhombic, C2221 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2c 2 | Cell parameters from 664 reflections |
a = 6.7980 (6) Å | θ = 3.5–22.8° |
b = 10.9084 (9) Å | µ = 0.08 mm−1 |
c = 25.331 (2) Å | T = 296 K |
V = 1878.4 (3) Å3 | Plate, colorless |
Z = 4 | 0.50 × 0.45 × 0.03 mm |
F(000) = 744 |
Bruker CCD area detector diffractometer | 1607 independent reflections |
Radiation source: fine-focus sealed tube | 1228 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.1°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS, Blessing, 1995) | h = −7→8 |
Tmin = 0.684, Tmax = 0.998 | k = −12→12 |
3653 measured reflections | l = −30→29 |
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)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0665P)2 + 0.3025P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
1607 reflections | Δρmax = 0.13 e Å−3 |
140 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods |
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 | ||
N13 | 0.1034 (3) | 0.8534 (3) | 0.15061 (9) | 0.0544 (6) | |
N11 | 0.1330 (3) | 0.6485 (3) | 0.15224 (9) | 0.0528 (6) | |
C12 | 0.0586 (3) | 0.7520 (3) | 0.17554 (9) | 0.0453 (6) | |
C1 | −0.0632 (3) | 0.7514 (3) | 0.22506 (9) | 0.0455 (6) | |
O1 | −0.1995 (2) | 0.65471 (19) | 0.22694 (7) | 0.0549 (5) | |
C11 | 0.2369 (4) | 0.6885 (4) | 0.10867 (11) | 0.0602 (9) | |
C13 | 0.2181 (4) | 0.8163 (4) | 0.10822 (10) | 0.0603 (9) | |
C17 | 0.3457 (5) | 0.6257 (5) | 0.07106 (15) | 0.0887 (14) | |
C2 | −0.3528 (4) | 0.6667 (3) | 0.18888 (12) | 0.0700 (9) | |
H2A | −0.4317 | 0.7371 | 0.1972 | 0.105* | |
H2B | −0.4336 | 0.5946 | 0.1894 | 0.105* | |
H2C | −0.2964 | 0.6766 | 0.1544 | 0.105* | |
C18 | 0.1200 (5) | 0.5205 (3) | 0.16879 (12) | 0.0692 (9) | |
H18A | 0.1295 | 0.5158 | 0.2066 | 0.104* | |
H18B | 0.2254 | 0.4747 | 0.1531 | 0.104* | |
H18C | −0.0037 | 0.4869 | 0.1576 | 0.104* | |
C15 | 0.4206 (6) | 0.8229 (9) | 0.03198 (16) | 0.1101 (18) | |
C14 | 0.3107 (6) | 0.8855 (5) | 0.06901 (14) | 0.0856 (13) | |
C16 | 0.4373 (7) | 0.6962 (8) | 0.03325 (18) | 0.114 (2) | |
H16 | 0.513 (7) | 0.660 (5) | 0.0053 (18) | 0.125 (14)* | |
H14 | 0.301 (5) | 0.974 (3) | 0.0688 (15) | 0.075 (12)* | |
H15 | 0.487 (6) | 0.884 (4) | 0.0056 (18) | 0.116 (15)* | |
H17 | 0.365 (5) | 0.539 (4) | 0.0736 (15) | 0.076 (11)* | |
H1 | −0.128 (3) | 0.830 (3) | 0.2246 (9) | 0.041 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N13 | 0.0551 (12) | 0.0536 (16) | 0.0545 (12) | −0.0028 (13) | −0.0038 (11) | 0.0041 (13) |
N11 | 0.0517 (11) | 0.0524 (15) | 0.0542 (12) | 0.0077 (13) | −0.0090 (10) | −0.0107 (13) |
C12 | 0.0429 (11) | 0.0418 (14) | 0.0514 (11) | 0.0003 (15) | −0.0078 (10) | −0.0008 (17) |
C1 | 0.0434 (11) | 0.0357 (13) | 0.0576 (12) | 0.0025 (15) | −0.0043 (11) | −0.0010 (17) |
O1 | 0.0464 (9) | 0.0550 (12) | 0.0633 (9) | −0.0084 (10) | −0.0123 (9) | 0.0067 (10) |
C11 | 0.0454 (14) | 0.086 (3) | 0.0491 (15) | 0.0104 (16) | −0.0103 (13) | −0.0098 (18) |
C13 | 0.0479 (14) | 0.084 (3) | 0.0491 (15) | −0.0029 (18) | −0.0081 (13) | 0.0064 (18) |
C17 | 0.066 (2) | 0.132 (5) | 0.068 (2) | 0.032 (3) | −0.0049 (19) | −0.028 (3) |
C2 | 0.0530 (15) | 0.079 (2) | 0.0783 (18) | −0.0068 (17) | −0.0218 (14) | 0.0015 (19) |
C18 | 0.0752 (18) | 0.0431 (18) | 0.089 (2) | 0.0133 (16) | −0.0199 (16) | −0.0145 (16) |
C15 | 0.063 (2) | 0.206 (6) | 0.061 (2) | −0.002 (4) | 0.007 (2) | 0.023 (4) |
C14 | 0.069 (2) | 0.125 (4) | 0.062 (2) | −0.014 (2) | −0.0101 (19) | 0.021 (2) |
C16 | 0.072 (2) | 0.211 (7) | 0.060 (2) | 0.035 (4) | 0.006 (2) | −0.015 (4) |
N13—C12 | 1.310 (4) | C17—C16 | 1.377 (8) |
N13—C13 | 1.387 (4) | C17—H17 | 0.95 (4) |
N11—C12 | 1.371 (4) | C2—H2A | 0.9600 |
N11—C11 | 1.381 (4) | C2—H2B | 0.9600 |
C11—C13 | 1.400 (4) | C2—H2C | 0.9600 |
N11—C18 | 1.460 (4) | C18—H18A | 0.9600 |
C12—C1 | 1.503 (3) | C18—H18B | 0.9600 |
C1—O1 | 1.404 (3) | C18—H18C | 0.9600 |
C1—C1i | 1.528 (4) | C15—C14 | 1.380 (7) |
C1—H1 | 0.96 (3) | C15—C16 | 1.387 (8) |
O1—C2 | 1.426 (3) | C15—H15 | 1.04 (5) |
C11—C17 | 1.387 (4) | C14—H14 | 0.97 (3) |
C13—C14 | 1.397 (5) | C16—H16 | 0.96 (5) |
C12—N13—C13 | 104.9 (3) | C11—C17—H17 | 121 (2) |
C12—N11—C11 | 105.8 (3) | O1—C2—H2A | 109.5 |
C12—N11—C18 | 129.9 (2) | O1—C2—H2B | 109.5 |
C11—N11—C18 | 124.3 (3) | H2A—C2—H2B | 109.5 |
N13—C12—N11 | 113.7 (2) | O1—C2—H2C | 109.5 |
N13—C12—C1 | 122.3 (3) | H2A—C2—H2C | 109.5 |
N11—C12—C1 | 124.0 (3) | H2B—C2—H2C | 109.5 |
O1—C1—C12 | 113.3 (2) | N11—C18—H18A | 109.5 |
O1—C1—C1i | 110.07 (17) | N11—C18—H18B | 109.5 |
C12—C1—C1i | 112.3 (2) | H18A—C18—H18B | 109.5 |
O1—C1—H1 | 111.7 (14) | N11—C18—H18C | 109.5 |
C12—C1—H1 | 103.6 (14) | H18A—C18—H18C | 109.5 |
C1i—C1—H1 | 105.5 (14) | H18B—C18—H18C | 109.5 |
C1—O1—C2 | 113.0 (2) | C14—C15—C16 | 121.5 (5) |
N11—C11—C17 | 131.7 (4) | C14—C15—H15 | 111 (3) |
N11—C11—C13 | 105.9 (3) | C16—C15—H15 | 128 (2) |
C17—C11—C13 | 122.3 (4) | C15—C14—C13 | 117.4 (5) |
N13—C13—C14 | 130.2 (4) | C15—C14—H14 | 122 (2) |
N13—C13—C11 | 109.6 (3) | C13—C14—H14 | 121 (2) |
C14—C13—C11 | 120.2 (4) | C17—C16—C15 | 122.4 (5) |
C16—C17—C11 | 116.3 (6) | C17—C16—H16 | 121 (3) |
C16—C17—H17 | 123 (2) | C15—C16—H16 | 116 (3) |
C13—N13—C12—N11 | −1.0 (3) | C18—N11—C11—C13 | −177.6 (2) |
C13—N13—C12—C1 | 178.96 (19) | C12—N13—C13—C14 | −178.4 (3) |
C11—N11—C12—N13 | 0.7 (3) | C12—N13—C13—C11 | 0.9 (3) |
C18—N11—C12—N13 | 178.0 (3) | N11—C11—C13—N13 | −0.4 (3) |
C11—N11—C12—C1 | −179.2 (2) | C17—C11—C13—N13 | −179.4 (2) |
C18—N11—C12—C1 | −1.9 (4) | N11—C11—C13—C14 | 178.9 (2) |
N13—C12—C1—O1 | 139.8 (2) | C17—C11—C13—C14 | −0.1 (5) |
N11—C12—C1—O1 | −40.3 (3) | N11—C11—C17—C16 | −177.8 (3) |
N13—C12—C1—C1i | −94.7 (2) | C13—C11—C17—C16 | 0.8 (5) |
N11—C12—C1—C1i | 85.2 (2) | C16—C15—C14—C13 | 0.6 (6) |
C12—C1—O1—C2 | −68.1 (3) | N13—C13—C14—C15 | 178.5 (3) |
C1i—C1—O1—C2 | 165.3 (2) | C11—C13—C14—C15 | −0.6 (5) |
C12—N11—C11—C17 | 178.6 (3) | C11—C17—C16—C15 | −0.9 (6) |
C18—N11—C11—C17 | 1.1 (4) | C14—C15—C16—C17 | 0.2 (8) |
C12—N11—C11—C13 | −0.1 (3) |
Symmetry code: (i) −x, y, −z+1/2. |