Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021742/na6123sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021742/na6123Vsup2.hkl |
CCDC reference: 180772
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.074
- wR factor = 0.248
- Data-to-parameter ratio = 15.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54052 REFLT_03 From the CIF: _diffrn_reflns_theta_max 80.59 From the CIF: _reflns_number_total 3916 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4201 Completeness (_total/calc) 93.22% Alert C: < 95% complete General Notes
RADNW_01 The radiation wavelength given implies that Cu Kalpha1 has been used. Please check that this is correct. Wavelength given = 1.54052
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software; data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997).
C20H21N3O4 | F(000) = 776 |
Mr = 367.40 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54052 Å |
a = 8.289 (1) Å | Cell parameters from 99 reflections |
b = 12.117 (2) Å | θ = 5–60° |
c = 19.225 (3) Å | µ = 0.75 mm−1 |
β = 99.88 (1)° | T = 293 K |
V = 1902.3 (5) Å3 | Sphere, colourless |
Z = 4 | 0.51 mm (radius) |
Kuma KM-4 diffractometer | 1952 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 80.6°, θmin = 4.3° |
ω–2θ scans | h = −9→9 |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | k = 0→15 |
Tmin = 0.692, Tmax = 0.715 | l = −24→0 |
4204 measured reflections | 2 standard reflections every 100 reflections |
3916 independent reflections | intensity decay: −4.0% |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.248 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.1581P)2] where P = (Fo2 + 2Fc2)/3 |
3916 reflections | (Δ/σ)max = 0.006 |
250 parameters | Δρmax = 0.58 e Å−3 |
0 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 | ||
N12 | 0.6189 (3) | 0.7165 (2) | 0.13601 (15) | 0.0485 (6) | |
C21 | 0.5487 (4) | 0.7771 (3) | 0.1819 (2) | 0.0564 (8) | |
O13 | 0.4613 (3) | 0.7330 (2) | 0.21980 (14) | 0.0674 (7) | |
C22 | 0.5818 (6) | 0.8990 (3) | 0.1872 (3) | 0.0767 (12) | |
H22A | 0.6972 | 0.9119 | 0.1907 | 0.092* | |
H22B | 0.5453 | 0.9279 | 0.2283 | 0.092* | |
H22C | 0.5241 | 0.9351 | 0.1458 | 0.092* | |
C12 | 0.5837 (4) | 0.5990 (2) | 0.13085 (18) | 0.0459 (7) | |
H12A | 0.5941 | 0.5677 | 0.1779 | 0.055* | |
H12B | 0.6624 | 0.5626 | 0.1066 | 0.055* | |
C11 | 0.4122 (4) | 0.5786 (3) | 0.09102 (17) | 0.0479 (7) | |
O11 | 0.3327 (3) | 0.6527 (2) | 0.05875 (16) | 0.0746 (8) | |
N1 | 0.3484 (3) | 0.4755 (2) | 0.09372 (14) | 0.0465 (6) | |
C8 | 0.1713 (4) | 0.4615 (3) | 0.06975 (19) | 0.0574 (9) | |
H8A | 0.1532 | 0.4065 | 0.0325 | 0.069* | |
H8B | 0.1248 | 0.5306 | 0.0504 | 0.069* | |
C7 | 0.0872 (4) | 0.4264 (3) | 0.1285 (2) | 0.0615 (10) | |
O1 | −0.0516 (3) | 0.4530 (3) | 0.1315 (2) | 0.0998 (11) | |
N2 | 0.1776 (4) | 0.3617 (3) | 0.17842 (19) | 0.0591 (8) | |
H3 | 0.135 (5) | 0.325 (4) | 0.204 (2) | 0.077 (14)* | |
C6 | 0.3362 (4) | 0.3262 (3) | 0.17427 (17) | 0.0478 (7) | |
C1 | 0.4261 (4) | 0.3832 (2) | 0.13107 (17) | 0.0459 (7) | |
C2 | 0.5806 (4) | 0.3460 (3) | 0.1232 (2) | 0.0559 (9) | |
H2 | 0.6379 | 0.3806 | 0.0918 | 0.067* | |
C3 | 0.6476 (5) | 0.2573 (3) | 0.1625 (3) | 0.0719 (12) | |
H3A | 0.7519 | 0.2329 | 0.1583 | 0.086* | |
C4 | 0.5623 (5) | 0.2043 (3) | 0.2081 (2) | 0.0703 (11) | |
H4 | 0.6106 | 0.1458 | 0.2353 | 0.084* | |
C5 | 0.4061 (5) | 0.2371 (3) | 0.2136 (2) | 0.0612 (9) | |
H5 | 0.3478 | 0.1998 | 0.2436 | 0.073* | |
C13 | 0.6987 (4) | 0.7639 (3) | 0.08156 (18) | 0.0550 (8) | |
C18 | 0.8668 (5) | 0.7447 (3) | 0.0833 (2) | 0.0610 (9) | |
H18 | 0.9247 | 0.7028 | 0.1198 | 0.073* | |
C17 | 0.9453 (5) | 0.7855 (4) | 0.0335 (2) | 0.0733 (11) | |
H17 | 1.0555 | 0.7695 | 0.0346 | 0.088* | |
C16 | 0.8651 (5) | 0.8491 (4) | −0.0176 (2) | 0.0724 (12) | |
C15 | 0.7003 (7) | 0.8703 (4) | −0.0238 (2) | 0.0884 (15) | |
H15 | 0.6462 | 0.9126 | −0.0610 | 0.106* | |
C14 | 0.6124 (6) | 0.8251 (3) | 0.0289 (2) | 0.0774 (12) | |
H14 | 0.5009 | 0.8378 | 0.0265 | 0.093* | |
O12 | 0.9570 (4) | 0.8877 (3) | −0.06865 (19) | 0.1013 (11) | |
C19 | 0.8841 (8) | 0.9603 (4) | −0.1158 (3) | 0.1053 (18) | |
H19A | 0.8537 | 1.0256 | −0.0918 | 0.126* | |
H19B | 0.7854 | 0.9283 | −0.1425 | 0.126* | |
C20 | 1.0017 (7) | 0.9920 (4) | −0.1656 (3) | 0.0962 (16) | |
H20A | 0.9531 | 1.0489 | −0.1972 | 0.115* | |
H20B | 1.0235 | 0.9285 | −0.1923 | 0.115* | |
H20C | 1.1024 | 1.0186 | −0.1385 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N12 | 0.0395 (15) | 0.0437 (13) | 0.0646 (16) | −0.0056 (10) | 0.0153 (12) | −0.0047 (12) |
C21 | 0.050 (2) | 0.0485 (17) | 0.073 (2) | −0.0019 (15) | 0.0162 (17) | 0.0002 (17) |
O13 | 0.0607 (16) | 0.0601 (15) | 0.0901 (18) | −0.0025 (12) | 0.0379 (14) | 0.0010 (13) |
C22 | 0.090 (3) | 0.0451 (19) | 0.102 (3) | −0.0049 (19) | 0.039 (3) | −0.008 (2) |
C12 | 0.0352 (16) | 0.0406 (15) | 0.0628 (19) | −0.0038 (12) | 0.0110 (13) | 0.0005 (13) |
C11 | 0.0434 (18) | 0.0477 (17) | 0.0531 (17) | −0.0012 (13) | 0.0098 (14) | 0.0023 (14) |
O11 | 0.0546 (15) | 0.0594 (15) | 0.103 (2) | −0.0041 (11) | −0.0069 (14) | 0.0292 (14) |
N1 | 0.0294 (13) | 0.0459 (13) | 0.0627 (15) | −0.0012 (10) | 0.0035 (11) | 0.0017 (12) |
C8 | 0.0340 (18) | 0.062 (2) | 0.071 (2) | −0.0068 (14) | −0.0042 (15) | 0.0063 (17) |
C7 | 0.0266 (17) | 0.066 (2) | 0.090 (3) | −0.0063 (15) | 0.0063 (16) | 0.005 (2) |
O1 | 0.0327 (15) | 0.113 (3) | 0.155 (3) | 0.0056 (15) | 0.0225 (17) | 0.032 (2) |
N2 | 0.0405 (17) | 0.0590 (17) | 0.080 (2) | −0.0048 (13) | 0.0158 (15) | 0.0079 (16) |
C6 | 0.0338 (16) | 0.0477 (16) | 0.0605 (18) | −0.0039 (13) | 0.0039 (13) | −0.0067 (14) |
C1 | 0.0368 (17) | 0.0382 (14) | 0.0611 (18) | −0.0029 (12) | 0.0035 (13) | −0.0066 (13) |
C2 | 0.0377 (18) | 0.0460 (16) | 0.085 (2) | −0.0005 (13) | 0.0132 (16) | −0.0083 (17) |
C3 | 0.0398 (19) | 0.0516 (19) | 0.121 (3) | 0.0065 (15) | 0.005 (2) | −0.005 (2) |
C4 | 0.060 (2) | 0.0447 (18) | 0.098 (3) | 0.0034 (16) | −0.011 (2) | 0.0023 (19) |
C5 | 0.058 (2) | 0.0508 (19) | 0.072 (2) | −0.0066 (16) | 0.0013 (17) | 0.0069 (17) |
C13 | 0.059 (2) | 0.0455 (17) | 0.062 (2) | −0.0134 (15) | 0.0143 (17) | −0.0052 (15) |
C18 | 0.055 (2) | 0.062 (2) | 0.070 (2) | −0.0146 (16) | 0.0243 (18) | −0.0118 (17) |
C17 | 0.066 (3) | 0.077 (3) | 0.081 (3) | −0.009 (2) | 0.025 (2) | −0.009 (2) |
C16 | 0.065 (3) | 0.078 (3) | 0.081 (3) | −0.032 (2) | 0.030 (2) | −0.012 (2) |
C15 | 0.121 (4) | 0.068 (3) | 0.068 (3) | −0.022 (3) | −0.006 (3) | 0.011 (2) |
C14 | 0.081 (3) | 0.068 (2) | 0.082 (3) | −0.015 (2) | 0.010 (2) | 0.010 (2) |
O12 | 0.104 (3) | 0.101 (3) | 0.102 (2) | −0.008 (2) | 0.025 (2) | 0.017 (2) |
C19 | 0.141 (5) | 0.070 (3) | 0.090 (3) | −0.023 (3) | −0.020 (3) | −0.008 (3) |
C20 | 0.132 (5) | 0.082 (3) | 0.085 (3) | −0.022 (3) | 0.048 (3) | 0.007 (2) |
N12—C21 | 1.354 (4) | C2—C3 | 1.375 (5) |
N12—C13 | 1.449 (4) | C2—H2 | 0.9300 |
N12—C12 | 1.454 (4) | C3—C4 | 1.375 (6) |
C21—O13 | 1.234 (4) | C3—H3A | 0.9300 |
C21—C22 | 1.502 (5) | C4—C5 | 1.376 (5) |
C22—H22A | 0.9600 | C4—H4 | 0.9300 |
C22—H22B | 0.9600 | C5—H5 | 0.9300 |
C22—H22C | 0.9600 | C13—C14 | 1.356 (5) |
C12—C11 | 1.515 (4) | C13—C18 | 1.407 (5) |
C12—H12A | 0.9700 | C18—C17 | 1.342 (5) |
C12—H12B | 0.9700 | C18—H18 | 0.9300 |
C11—O11 | 1.219 (4) | C17—C16 | 1.332 (6) |
C11—N1 | 1.361 (4) | C17—H17 | 0.9300 |
N1—C1 | 1.422 (4) | C16—C15 | 1.375 (7) |
N1—C8 | 1.470 (4) | C16—O12 | 1.421 (5) |
C8—C7 | 1.487 (5) | C15—C14 | 1.452 (6) |
C8—H8A | 0.9700 | C15—H15 | 0.9300 |
C8—H8B | 0.9700 | C14—H14 | 0.9300 |
C7—O1 | 1.206 (4) | O12—C19 | 1.331 (6) |
C7—N2 | 1.361 (5) | C19—C20 | 1.528 (7) |
N2—C6 | 1.398 (4) | C19—H19A | 0.9700 |
N2—H3 | 0.78 (4) | C19—H19B | 0.9700 |
C6—C5 | 1.387 (5) | C20—H20A | 0.9600 |
C6—C1 | 1.391 (4) | C20—H20B | 0.9600 |
C1—C2 | 1.391 (4) | C20—H20C | 0.9600 |
C21—N12—C13 | 123.8 (3) | C3—C2—H2 | 120.4 |
C21—N12—C12 | 118.2 (3) | C1—C2—H2 | 120.4 |
C13—N12—C12 | 116.8 (3) | C2—C3—C4 | 120.8 (3) |
O13—C21—N12 | 120.8 (3) | C2—C3—H3A | 119.6 |
O13—C21—C22 | 120.4 (3) | C4—C3—H3A | 119.6 |
N12—C21—C22 | 118.9 (3) | C3—C4—C5 | 120.5 (3) |
C21—C22—H22A | 109.5 | C3—C4—H4 | 119.7 |
C21—C22—H22B | 109.5 | C5—C4—H4 | 119.7 |
H22A—C22—H22B | 109.5 | C4—C5—C6 | 119.5 (3) |
C21—C22—H22C | 109.5 | C4—C5—H5 | 120.2 |
H22A—C22—H22C | 109.5 | C6—C5—H5 | 120.2 |
H22B—C22—H22C | 109.5 | C14—C13—C18 | 120.1 (4) |
N12—C12—C11 | 110.8 (3) | C14—C13—N12 | 120.6 (3) |
N12—C12—H12A | 109.5 | C18—C13—N12 | 119.3 (3) |
C11—C12—H12A | 109.5 | C17—C18—C13 | 121.4 (4) |
N12—C12—H12B | 109.5 | C17—C18—H18 | 119.3 |
C11—C12—H12B | 109.5 | C13—C18—H18 | 119.3 |
H12A—C12—H12B | 108.1 | C16—C17—C18 | 119.8 (4) |
O11—C11—N1 | 121.1 (3) | C16—C17—H17 | 120.1 |
O11—C11—C12 | 121.0 (3) | C18—C17—H17 | 120.1 |
N1—C11—C12 | 117.9 (3) | C17—C16—C15 | 122.4 (4) |
C11—N1—C1 | 126.5 (2) | C17—C16—O12 | 116.1 (4) |
C11—N1—C8 | 117.9 (3) | C15—C16—O12 | 121.3 (4) |
C1—N1—C8 | 114.1 (3) | C16—C15—C14 | 118.6 (4) |
N1—C8—C7 | 111.6 (3) | C16—C15—H15 | 120.7 |
N1—C8—H8A | 109.3 | C14—C15—H15 | 120.7 |
C7—C8—H8A | 109.3 | C13—C14—C15 | 117.6 (4) |
N1—C8—H8B | 109.3 | C13—C14—H14 | 121.2 |
C7—C8—H8B | 109.3 | C15—C14—H14 | 121.2 |
H8A—C8—H8B | 108.0 | C19—O12—C16 | 117.0 (5) |
O1—C7—N2 | 122.3 (4) | O12—C19—C20 | 109.2 (5) |
O1—C7—C8 | 122.4 (4) | O12—C19—H19A | 109.8 |
N2—C7—C8 | 115.3 (3) | C20—C19—H19A | 109.8 |
C7—N2—C6 | 123.1 (3) | O12—C19—H19B | 109.8 |
C7—N2—H3 | 121 (3) | C20—C19—H19B | 109.8 |
C6—N2—H3 | 113 (3) | H19A—C19—H19B | 108.3 |
C5—C6—C1 | 119.8 (3) | C19—C20—H20A | 109.5 |
C5—C6—N2 | 121.1 (3) | C19—C20—H20B | 109.5 |
C1—C6—N2 | 119.1 (3) | H20A—C20—H20B | 109.5 |
C2—C1—C6 | 120.1 (3) | C19—C20—H20C | 109.5 |
C2—C1—N1 | 123.1 (3) | H20A—C20—H20C | 109.5 |
C6—C1—N1 | 116.7 (3) | H20B—C20—H20C | 109.5 |
C3—C2—C1 | 119.1 (3) | ||
C1—C6—N2—C7 | 20.2 (5) | C8—N1—C11—C12 | 166.0 (3) |
C6—N2—C7—C8 | −2.5 (5) | N1—C11—C12—N12 | −167.1 (3) |
N2—C7—C8—N1 | −32.3 (4) | C11—C12—N12—C21 | 74.5 (4) |
C7—C8—N1—C1 | 51.6 (4) | C11—C12—N12—C13 | −93.1 (3) |
C8—N1—C1—C6 | −35.7 (4) | C12—N12—C13—C18 | −75.5 (4) |
N1—C1—C6—N2 | 0.1 (4) | C12—N12—C13—C14 | 103.6 (4) |
C1—N1—C11—O11 | −178.0 (3) | C15—C16—O12—C19 | 11.1 (6) |
C8—N1—C11—O11 | −12.6 (5) | C17—C16—O12—C19 | −173.2 (4) |
C1—N1—C11—C12 | 0.6 (5) | C16—O12—C19—C20 | 179.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O11 | 0.97 | 2.26 | 2.702 (4) | 107 |
N2—H3···O13i | 0.78 (4) | 2.11 (4) | 2.891 (4) | 174 (4) |
C20—H20B···O13ii | 0.96 | 2.58 | 3.486 (6) | 158 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1/2, −y+3/2, z−1/2. |
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