Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018694/ci6065sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018694/ci6065Isup2.hkl |
CCDC reference: 177202
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.041
- wR factor = 0.104
- Data-to-parameter ratio = 10.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.53 From the CIF: _reflns_number_total 2571 Count of symmetry unique reflns 2579 Completeness (_total/calc) 99.69% 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 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.
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C21H19N3O4 | Dx = 1.314 Mg m−3 |
Mr = 377.39 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4522 reflections |
a = 4.7919 (9) Å | θ = 1–27.5° |
b = 15.775 (3) Å | µ = 0.09 mm−1 |
c = 25.228 (5) Å | T = 294 K |
V = 1907.1 (6) Å3 | Plate, colourless |
Z = 4 | 0.24 × 0.20 × 0.18 mm |
F(000) = 792 |
Siemens CCD area-detector diffractometer | 2571 independent reflections |
Radiation source: fine-focus sealed tube | 1007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
Detector resolution: 8.3 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω scans | h = −6→5 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −20→19 |
Tmin = 0.978, Tmax = 0.984 | l = −29→32 |
12538 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.85 | (Δ/σ)max < 0.001 |
2571 reflections | Δρmax = 0.14 e Å−3 |
253 parameters | Δρmin = −0.20 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 | 0.3689 (8) | 0.20900 (18) | 0.25572 (11) | 0.1129 (13) | |
O2 | 1.0181 (7) | −0.02251 (16) | 0.23433 (10) | 0.0797 (8) | |
O3 | 1.1365 (7) | 0.10741 (15) | 0.48373 (10) | 0.0982 (11) | |
O4 | 1.0396 (6) | −0.11966 (15) | 0.36016 (9) | 0.0738 (8) | |
N1 | 0.7888 (6) | 0.13141 (16) | 0.36080 (11) | 0.0543 (8) | |
N2 | 0.6785 (7) | 0.10072 (17) | 0.25762 (10) | 0.0636 (9) | |
H2A | 0.7890 | 0.0741 | 0.2787 | 0.076* | |
N3 | 1.1108 (7) | 0.01954 (17) | 0.41213 (10) | 0.0630 (9) | |
H3A | 1.0491 | 0.0171 | 0.3801 | 0.076* | |
C1 | 1.2034 (10) | −0.0912 (2) | 0.22548 (16) | 0.0900 (15) | |
H1B | 1.3066 | −0.1025 | 0.2573 | 0.135* | |
H1C | 1.3304 | −0.0769 | 0.1974 | 0.135* | |
H1D | 1.0985 | −0.1406 | 0.2157 | 0.135* | |
C2 | 0.8516 (9) | 0.0033 (3) | 0.19318 (16) | 0.0662 (11) | |
C3 | 0.8550 (10) | −0.0318 (2) | 0.14311 (18) | 0.0794 (14) | |
H3B | 0.9765 | −0.0758 | 0.1350 | 0.095* | |
C4 | 0.6727 (12) | 0.0001 (3) | 0.10503 (18) | 0.0898 (17) | |
H4A | 0.6746 | −0.0231 | 0.0711 | 0.108* | |
C5 | 0.4911 (11) | 0.0645 (3) | 0.11623 (16) | 0.0862 (15) | |
H5A | 0.3690 | 0.0846 | 0.0905 | 0.103* | |
C6 | 0.4926 (10) | 0.0994 (2) | 0.16694 (15) | 0.0725 (12) | |
H6A | 0.3711 | 0.1435 | 0.1750 | 0.087* | |
C7 | 0.6699 (9) | 0.0697 (2) | 0.20503 (14) | 0.0591 (11) | |
C8 | 0.5389 (10) | 0.1658 (2) | 0.27928 (15) | 0.0675 (12) | |
C9 | 0.6133 (9) | 0.1839 (2) | 0.33589 (14) | 0.0582 (11) | |
C10 | 0.5008 (9) | 0.2547 (2) | 0.35993 (15) | 0.0725 (12) | |
H10A | 0.3745 | 0.2890 | 0.3419 | 0.087* | |
C11 | 0.5789 (10) | 0.2738 (2) | 0.41112 (15) | 0.0801 (13) | |
H11A | 0.5092 | 0.3219 | 0.4278 | 0.096* | |
C12 | 0.7589 (10) | 0.2216 (2) | 0.43699 (14) | 0.0742 (13) | |
H12A | 0.8129 | 0.2331 | 0.4717 | 0.089* | |
C13 | 0.8609 (9) | 0.1505 (2) | 0.41071 (14) | 0.0589 (11) | |
C14 | 1.0511 (9) | 0.0906 (2) | 0.43950 (15) | 0.0642 (11) | |
C15 | 1.2627 (8) | −0.0510 (2) | 0.43016 (13) | 0.0539 (10) | |
C16 | 1.4442 (9) | −0.0510 (2) | 0.47177 (14) | 0.0701 (12) | |
H16A | 1.4746 | −0.0013 | 0.4907 | 0.084* | |
C17 | 1.5841 (9) | −0.1246 (3) | 0.48614 (15) | 0.0755 (12) | |
H17A | 1.7064 | −0.1243 | 0.5148 | 0.091* | |
C18 | 1.5413 (9) | −0.1976 (2) | 0.45809 (15) | 0.0731 (12) | |
H18A | 1.6358 | −0.2468 | 0.4676 | 0.088* | |
C19 | 1.3606 (9) | −0.1988 (2) | 0.41614 (14) | 0.0665 (11) | |
H19A | 1.3315 | −0.2488 | 0.3975 | 0.080* | |
C20 | 1.2214 (8) | −0.1260 (2) | 0.40137 (13) | 0.0565 (10) | |
C21 | 0.9571 (11) | −0.1966 (2) | 0.33382 (14) | 0.0881 (15) | |
H21B | 0.8291 | −0.1834 | 0.3057 | 0.132* | |
H21C | 0.8680 | −0.2337 | 0.3588 | 0.132* | |
H21A | 1.1189 | −0.2240 | 0.3194 | 0.132* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.161 (3) | 0.093 (2) | 0.084 (2) | 0.064 (3) | −0.041 (2) | −0.0022 (17) |
O2 | 0.082 (2) | 0.0748 (18) | 0.082 (2) | 0.0167 (19) | 0.0105 (18) | −0.0082 (15) |
O3 | 0.155 (3) | 0.0761 (17) | 0.0634 (17) | 0.027 (2) | −0.036 (2) | −0.0266 (15) |
O4 | 0.093 (2) | 0.0621 (15) | 0.0660 (16) | 0.0006 (17) | −0.0252 (16) | −0.0161 (13) |
N1 | 0.069 (2) | 0.0438 (16) | 0.0495 (18) | 0.0060 (18) | 0.0004 (16) | −0.0019 (15) |
N2 | 0.087 (3) | 0.0550 (18) | 0.0489 (19) | 0.013 (2) | −0.0097 (18) | −0.0037 (16) |
N3 | 0.087 (3) | 0.0553 (18) | 0.0465 (18) | 0.005 (2) | −0.0158 (17) | −0.0090 (15) |
C1 | 0.080 (3) | 0.064 (3) | 0.126 (4) | 0.014 (3) | 0.025 (3) | −0.001 (2) |
C2 | 0.072 (3) | 0.064 (3) | 0.063 (3) | −0.012 (3) | 0.008 (3) | 0.003 (2) |
C3 | 0.101 (4) | 0.069 (3) | 0.068 (3) | −0.026 (3) | 0.034 (3) | −0.013 (3) |
C4 | 0.129 (5) | 0.085 (3) | 0.055 (3) | −0.049 (4) | 0.017 (3) | −0.002 (3) |
C5 | 0.118 (4) | 0.084 (3) | 0.057 (3) | −0.035 (4) | −0.005 (3) | 0.008 (2) |
C6 | 0.094 (4) | 0.060 (2) | 0.063 (3) | −0.010 (3) | −0.013 (3) | 0.011 (2) |
C7 | 0.076 (3) | 0.052 (2) | 0.049 (2) | −0.006 (2) | 0.002 (2) | −0.0013 (19) |
C8 | 0.090 (4) | 0.047 (2) | 0.065 (3) | 0.012 (3) | −0.001 (3) | −0.001 (2) |
C9 | 0.076 (3) | 0.044 (2) | 0.055 (2) | 0.001 (2) | 0.004 (2) | 0.0013 (19) |
C10 | 0.093 (4) | 0.053 (2) | 0.072 (3) | 0.021 (3) | 0.007 (3) | 0.004 (2) |
C11 | 0.116 (4) | 0.058 (2) | 0.066 (3) | 0.019 (3) | 0.008 (3) | −0.012 (2) |
C12 | 0.111 (4) | 0.052 (2) | 0.060 (3) | 0.004 (3) | 0.004 (3) | −0.007 (2) |
C13 | 0.081 (3) | 0.044 (2) | 0.052 (2) | −0.002 (2) | 0.001 (2) | −0.0060 (19) |
C14 | 0.084 (3) | 0.057 (2) | 0.051 (2) | 0.005 (3) | −0.006 (2) | −0.009 (2) |
C15 | 0.062 (3) | 0.053 (2) | 0.048 (2) | 0.002 (2) | −0.008 (2) | −0.0011 (19) |
C16 | 0.082 (3) | 0.067 (2) | 0.061 (2) | 0.001 (3) | −0.020 (2) | −0.009 (2) |
C17 | 0.075 (3) | 0.085 (3) | 0.067 (3) | 0.006 (3) | −0.018 (2) | 0.007 (2) |
C18 | 0.083 (3) | 0.067 (3) | 0.069 (3) | 0.012 (3) | −0.005 (3) | 0.003 (2) |
C19 | 0.073 (3) | 0.060 (3) | 0.067 (3) | −0.003 (3) | 0.000 (2) | −0.001 (2) |
C20 | 0.064 (3) | 0.057 (2) | 0.048 (2) | −0.002 (2) | −0.005 (2) | −0.002 (2) |
C21 | 0.100 (4) | 0.081 (3) | 0.083 (3) | −0.028 (3) | −0.011 (3) | −0.029 (2) |
O1—C8 | 1.217 (4) | C4—C5 | 1.368 (6) |
O2—C2 | 1.371 (4) | C5—C6 | 1.393 (5) |
O2—C1 | 1.418 (4) | C6—C7 | 1.366 (5) |
O3—C14 | 1.218 (4) | C8—C9 | 1.499 (5) |
O4—C20 | 1.360 (4) | C9—C10 | 1.381 (4) |
O4—C21 | 1.439 (4) | C10—C11 | 1.378 (5) |
N1—C9 | 1.337 (4) | C11—C12 | 1.360 (5) |
N1—C13 | 1.340 (4) | C12—C13 | 1.391 (4) |
N2—C8 | 1.342 (4) | C13—C14 | 1.500 (5) |
N2—C7 | 1.415 (4) | C15—C16 | 1.363 (4) |
N3—C14 | 1.348 (4) | C15—C20 | 1.402 (4) |
N3—C15 | 1.405 (4) | C16—C17 | 1.390 (5) |
C2—C3 | 1.379 (5) | C17—C18 | 1.367 (4) |
C2—C7 | 1.394 (5) | C18—C19 | 1.368 (5) |
C3—C4 | 1.392 (5) | C19—C20 | 1.380 (5) |
C2—O2—C1 | 118.2 (3) | C10—C9—C8 | 118.7 (4) |
C20—O4—C21 | 117.9 (3) | C11—C10—C9 | 118.8 (4) |
C9—N1—C13 | 117.7 (3) | C12—C11—C10 | 119.4 (4) |
C8—N2—C7 | 129.2 (3) | C11—C12—C13 | 118.8 (4) |
C14—N3—C15 | 127.1 (3) | N1—C13—C12 | 122.6 (4) |
O2—C2—C3 | 124.5 (4) | N1—C13—C14 | 118.0 (3) |
O2—C2—C7 | 115.1 (4) | C12—C13—C14 | 119.3 (3) |
C3—C2—C7 | 120.3 (4) | O3—C14—N3 | 125.4 (4) |
C2—C3—C4 | 118.7 (4) | O3—C14—C13 | 120.7 (3) |
C5—C4—C3 | 121.7 (4) | N3—C14—C13 | 113.9 (3) |
C4—C5—C6 | 118.7 (5) | C16—C15—C20 | 119.3 (4) |
C7—C6—C5 | 120.9 (4) | C16—C15—N3 | 125.5 (3) |
C6—C7—C2 | 119.7 (4) | C20—C15—N3 | 115.3 (3) |
C6—C7—N2 | 124.0 (4) | C15—C16—C17 | 120.6 (4) |
C2—C7—N2 | 116.3 (4) | C18—C17—C16 | 119.8 (4) |
O1—C8—N2 | 124.3 (4) | C17—C18—C19 | 120.4 (4) |
O1—C8—C9 | 121.1 (4) | C18—C19—C20 | 120.3 (4) |
N2—C8—C9 | 114.6 (4) | O4—C20—C19 | 125.2 (3) |
N1—C9—C10 | 122.7 (3) | O4—C20—C15 | 115.1 (3) |
N1—C9—C8 | 118.6 (3) | C19—C20—C15 | 119.6 (4) |
C1—O2—C2—C3 | −1.3 (5) | C10—C11—C12—C13 | 0.5 (6) |
C1—O2—C2—C7 | 178.5 (3) | C9—N1—C13—C12 | 0.5 (5) |
O2—C2—C3—C4 | 179.4 (3) | C9—N1—C13—C14 | 178.3 (3) |
C7—C2—C3—C4 | −0.3 (5) | C11—C12—C13—N1 | 0.0 (6) |
C2—C3—C4—C5 | −0.4 (6) | C11—C12—C13—C14 | −177.7 (4) |
C3—C4—C5—C6 | 0.8 (6) | C15—N3—C14—O3 | 5.1 (7) |
C4—C5—C6—C7 | −0.5 (6) | C15—N3—C14—C13 | −174.3 (3) |
C5—C6—C7—C2 | −0.2 (6) | N1—C13—C14—O3 | 175.6 (4) |
C5—C6—C7—N2 | −178.5 (4) | C12—C13—C14—O3 | −6.6 (6) |
O2—C2—C7—C6 | −179.2 (3) | N1—C13—C14—N3 | −4.9 (5) |
C3—C2—C7—C6 | 0.6 (5) | C12—C13—C14—N3 | 172.9 (4) |
O2—C2—C7—N2 | −0.7 (5) | C14—N3—C15—C16 | −20.5 (6) |
C3—C2—C7—N2 | 179.1 (3) | C14—N3—C15—C20 | 160.5 (4) |
C8—N2—C7—C6 | −5.1 (6) | C20—C15—C16—C17 | −0.9 (6) |
C8—N2—C7—C2 | 176.6 (3) | N3—C15—C16—C17 | −179.9 (4) |
C7—N2—C8—O1 | 2.0 (7) | C15—C16—C17—C18 | 0.5 (6) |
C7—N2—C8—C9 | −176.5 (3) | C16—C17—C18—C19 | −0.4 (6) |
C13—N1—C9—C10 | −1.6 (5) | C17—C18—C19—C20 | 0.6 (6) |
C13—N1—C9—C8 | 177.5 (4) | C21—O4—C20—C19 | 8.4 (5) |
O1—C8—C9—N1 | 176.1 (4) | C21—O4—C20—C15 | −171.2 (4) |
N2—C8—C9—N1 | −5.4 (5) | C18—C19—C20—O4 | 179.4 (4) |
O1—C8—C9—C10 | −4.8 (6) | C18—C19—C20—C15 | −1.0 (6) |
N2—C8—C9—C10 | 173.8 (3) | C16—C15—C20—O4 | −179.2 (3) |
N1—C9—C10—C11 | 2.1 (6) | N3—C15—C20—O4 | −0.1 (5) |
C8—C9—C10—C11 | −177.0 (4) | C16—C15—C20—C19 | 1.2 (6) |
C9—C10—C11—C12 | −1.5 (6) | N3—C15—C20—C19 | −179.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.86 | 2.19 | 2.602 (4) | 110 |
N2—H2A···N1 | 0.86 | 2.26 | 2.700 (4) | 112 |
N3—H3A···O4 | 0.86 | 2.22 | 2.580 (4) | 105 |
N3—H3A···N1 | 0.86 | 2.25 | 2.678 (4) | 111 |
C6—H6A···O1 | 0.93 | 2.28 | 2.891 (5) | 123 |
C11—H11A···O3i | 0.93 | 2.57 | 3.260 (4) | 132 |
C16—H16A···O3 | 0.93 | 2.37 | 2.917 (4) | 118 |
C21—H21B···O1ii | 0.96 | 2.49 | 3.124 (5) | 124 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1/2. |
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