Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008863/na6164sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008863/na6164Isup2.hkl |
CCDC reference: 189406
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO nd COLLECT; data reduction: DENZO nd COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
C13H10N2O2 | F(000) = 472 |
Mr = 226.23 | Dx = 1.360 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6650 (7) Å | Cell parameters from 1832 reflections |
b = 9.8140 (8) Å | θ = 1.0–27.5° |
c = 11.1544 (12) Å | µ = 0.09 mm−1 |
β = 108.833 (3)° | T = 293 K |
V = 1104.99 (17) Å3 | Plate, colourless |
Z = 4 | 0.30 × 0.10 × 0.03 mm |
Bruker-Nonius KappaCCD area-detector diffractometer | 2460 independent reflections |
Radiation source: Bruker Nonius FR591 rotating anode | 906 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.4°, θmin = 2.3° |
φ and ω scans | h = −13→13 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −11→12 |
Tmin = 0.972, Tmax = 0.997 | l = −14→14 |
4925 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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.201 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0831P)2] where P = (Fo2 + 2Fc2)/3 |
2460 reflections | (Δ/σ)max < 0.001 |
159 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 4.2083 (0.0133) x + 3.4036 (0.0122) y + 10.4039 (0.0053) z = 3.2471 (0.0091) * 0.0099 (0.0023) N1 * -0.0040 (0.0023) C2 * -0.0060 (0.0024) C3 * 0.0101 (0.0024) C4 * -0.0046 (0.0024) C5 * -0.0054 (0.0022) C6 Rms deviation of fitted atoms = 0.0071 - 4.2138 (0.0142) x - 2.9541 (0.0138) y + 10.5855 (0.0052) z = 5.2040 (0.0038) Angle to previous plane (with approximate e.s.d.) = 37.81 (0.09) * -0.0051 (0.0024) C61 * 0.0127 (0.0024) C62 * -0.0105 (0.0025) C63 * 0.0006 (0.0025) C64 * 0.0069 (0.0027) C65 * -0.0046 (0.0026) C66 Rms deviation of fitted atoms = 0.0078 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4633 (3) | −0.1765 (3) | 0.5582 (3) | 0.0352 (8) | |
H1 | 0.419 (3) | −0.103 (3) | 0.512 (4) | 0.069 (13)* | |
C2 | 0.5979 (4) | −0.1595 (3) | 0.6058 (3) | 0.0345 (9) | |
O2 | 0.6507 (2) | −0.0503 (2) | 0.5884 (2) | 0.0477 (8) | |
C3 | 0.6697 (3) | −0.2733 (3) | 0.6718 (3) | 0.0336 (9) | |
C31 | 0.8102 (4) | −0.2589 (3) | 0.7225 (4) | 0.0414 (10) | |
N32 | 0.9229 (3) | −0.2456 (3) | 0.7617 (4) | 0.0659 (11) | |
C4 | 0.6054 (4) | −0.3903 (3) | 0.6857 (3) | 0.0424 (10) | |
H4 | 0.6537 | −0.4632 | 0.7310 | 0.053* | |
C5 | 0.4679 (4) | −0.4008 (3) | 0.6321 (3) | 0.0414 (10) | |
H5 | 0.4253 | −0.4813 | 0.6403 | 0.052* | |
C6 | 0.3962 (3) | −0.2935 (3) | 0.5679 (3) | 0.0330 (9) | |
C61 | 0.2522 (3) | −0.2950 (3) | 0.5092 (3) | 0.0352 (9) | |
C62 | 0.1881 (3) | −0.4135 (3) | 0.4523 (3) | 0.0410 (10) | |
H62 | 0.2378 | −0.4915 | 0.4530 | 0.051* | |
C63 | 0.0530 (4) | −0.4180 (3) | 0.3951 (4) | 0.0460 (10) | |
H63 | 0.0129 | −0.4972 | 0.3548 | 0.057* | |
C64 | −0.0229 (4) | −0.3047 (4) | 0.3975 (4) | 0.0430 (10) | |
C65 | 0.0380 (4) | −0.1875 (4) | 0.4551 (4) | 0.0492 (11) | |
H65 | −0.0129 | −0.1111 | 0.4573 | 0.061* | |
C66 | 0.1735 (4) | −0.1820 (3) | 0.5095 (4) | 0.0451 (10) | |
H66 | 0.2132 | −0.1014 | 0.5470 | 0.056* | |
O64 | −0.1559 (3) | −0.3195 (2) | 0.3383 (3) | 0.0601 (8) | |
C67 | −0.2399 (4) | −0.2070 (4) | 0.3423 (5) | 0.0755 (15) | |
H671 | −0.2264 | −0.1822 | 0.4288 | 0.094* | |
H672 | −0.3308 | −0.2324 | 0.3024 | 0.094* | |
H673 | −0.2189 | −0.1308 | 0.2982 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.038 (2) | 0.0294 (17) | 0.035 (2) | 0.0037 (14) | 0.0083 (16) | 0.0034 (14) |
C2 | 0.037 (2) | 0.0313 (19) | 0.034 (2) | 0.0023 (16) | 0.0090 (19) | 0.0008 (16) |
O2 | 0.0425 (17) | 0.0352 (13) | 0.0627 (19) | −0.0030 (12) | 0.0134 (14) | 0.0090 (13) |
C3 | 0.036 (2) | 0.0312 (18) | 0.034 (2) | 0.0055 (16) | 0.0119 (19) | 0.0042 (16) |
C31 | 0.043 (3) | 0.035 (2) | 0.044 (3) | 0.009 (2) | 0.012 (2) | 0.0030 (18) |
N32 | 0.045 (2) | 0.068 (2) | 0.083 (3) | 0.0061 (19) | 0.018 (2) | 0.005 (2) |
C4 | 0.050 (3) | 0.0345 (19) | 0.044 (3) | 0.0112 (17) | 0.017 (2) | 0.0064 (17) |
C5 | 0.045 (3) | 0.0300 (19) | 0.050 (3) | −0.0006 (17) | 0.015 (2) | 0.0055 (17) |
C6 | 0.040 (2) | 0.0307 (18) | 0.031 (2) | 0.0000 (16) | 0.0152 (19) | 0.0000 (16) |
C61 | 0.038 (2) | 0.033 (2) | 0.037 (2) | −0.0034 (16) | 0.0160 (19) | −0.0002 (16) |
C62 | 0.044 (3) | 0.035 (2) | 0.051 (3) | −0.0005 (17) | 0.026 (2) | −0.0042 (18) |
C63 | 0.046 (3) | 0.045 (2) | 0.052 (3) | −0.0170 (19) | 0.023 (2) | −0.0092 (19) |
C64 | 0.033 (2) | 0.054 (2) | 0.045 (3) | 0.0003 (19) | 0.016 (2) | 0.001 (2) |
C65 | 0.041 (3) | 0.046 (2) | 0.062 (3) | 0.0061 (18) | 0.019 (2) | −0.009 (2) |
C66 | 0.044 (3) | 0.037 (2) | 0.053 (3) | −0.0011 (18) | 0.014 (2) | −0.0100 (18) |
O64 | 0.0344 (18) | 0.0706 (18) | 0.074 (2) | −0.0059 (14) | 0.0160 (16) | −0.0051 (16) |
C67 | 0.038 (3) | 0.105 (3) | 0.088 (4) | 0.008 (3) | 0.026 (3) | −0.008 (3) |
N1—C2 | 1.371 (4) | C61—C62 | 1.394 (4) |
N1—C6 | 1.375 (4) | C62—C63 | 1.375 (4) |
N1—H1 | 0.92 (4) | C62—H62 | 0.93 |
C2—O2 | 1.255 (4) | C63—C64 | 1.380 (4) |
C2—C3 | 1.419 (4) | C63—H63 | 0.93 |
C3—C4 | 1.372 (4) | C64—O64 | 1.366 (4) |
C3—C31 | 1.427 (5) | C64—C65 | 1.374 (5) |
C31—N32 | 1.147 (4) | C65—C66 | 1.377 (5) |
C4—C5 | 1.397 (4) | C65—H65 | 0.93 |
C4—H4 | 0.93 | C66—H66 | 0.93 |
C5—C6 | 1.362 (4) | O64—C67 | 1.432 (4) |
C5—H5 | 0.93 | C67—H671 | 0.96 |
C6—C61 | 1.462 (5) | C67—H672 | 0.96 |
C61—C66 | 1.392 (4) | C67—H673 | 0.96 |
C2—N1—C6 | 125.3 (3) | C63—C62—C61 | 121.6 (3) |
C2—N1—H1 | 114 (2) | C63—C62—H62 | 119.2 |
C6—N1—H1 | 121 (2) | C61—C62—H62 | 119.2 |
O2—C2—N1 | 120.7 (3) | C62—C63—C64 | 119.9 (3) |
O2—C2—C3 | 124.0 (3) | C62—C63—H63 | 120.0 |
N1—C2—C3 | 115.3 (3) | C64—C63—H63 | 120.0 |
C4—C3—C2 | 120.8 (3) | O64—C64—C65 | 125.1 (3) |
C4—C3—C31 | 122.5 (3) | O64—C64—C63 | 115.4 (3) |
C2—C3—C31 | 116.7 (3) | C65—C64—C63 | 119.5 (3) |
N32—C31—C3 | 178.8 (4) | C64—C65—C66 | 120.6 (3) |
C3—C4—C5 | 120.5 (3) | C64—C65—H65 | 119.7 |
C3—C4—H4 | 119.8 | C66—C65—H65 | 119.7 |
C5—C4—H4 | 119.8 | C65—C66—C61 | 121.1 (3) |
C6—C5—C4 | 120.1 (3) | C65—C66—H66 | 119.5 |
C6—C5—H5 | 120.0 | C61—C66—H66 | 119.5 |
C4—C5—H5 | 120.0 | C64—O64—C67 | 117.8 (3) |
C5—C6—N1 | 118.0 (3) | O64—C67—H671 | 109.5 |
C5—C6—C61 | 123.9 (3) | O64—C67—H672 | 109.5 |
N1—C6—C61 | 118.1 (3) | H671—C67—H672 | 109.5 |
C66—C61—C62 | 117.3 (3) | O64—C67—H673 | 109.5 |
C66—C61—C6 | 122.5 (3) | H671—C67—H673 | 109.5 |
C62—C61—C6 | 120.2 (3) | H672—C67—H673 | 109.5 |
C6—N1—C2—O2 | 177.5 (3) | C5—C6—C61—C62 | −36.6 (5) |
C6—N1—C2—C3 | −1.4 (5) | N1—C6—C61—C62 | 143.8 (3) |
O2—C2—C3—C4 | −179.1 (3) | C66—C61—C62—C63 | 2.0 (5) |
N1—C2—C3—C4 | −0.2 (5) | C6—C61—C62—C63 | −179.3 (3) |
O2—C2—C3—C31 | 1.1 (5) | C61—C62—C63—C64 | −2.5 (5) |
N1—C2—C3—C31 | 180.0 (3) | C62—C63—C64—O64 | −179.9 (3) |
C2—C3—C4—C5 | 1.6 (5) | C62—C63—C64—C65 | 1.3 (5) |
C31—C3—C4—C5 | −178.6 (3) | O64—C64—C65—C66 | −178.3 (4) |
C3—C4—C5—C6 | −1.4 (5) | C63—C64—C65—C66 | 0.3 (6) |
C4—C5—C6—N1 | −0.1 (5) | C64—C65—C66—C61 | −0.9 (6) |
C4—C5—C6—C61 | −179.7 (3) | C62—C61—C66—C65 | −0.3 (5) |
C2—N1—C6—C5 | 1.5 (5) | C6—C61—C66—C65 | −179.0 (3) |
C2—N1—C6—C61 | −178.8 (3) | C65—C64—O64—C67 | −3.7 (6) |
C5—C6—C61—C66 | 142.1 (4) | C63—C64—O64—C67 | 177.6 (3) |
N1—C6—C61—C66 | −37.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.92 (4) | 1.88 (4) | 2.797 (4) | 172 (3) |
C4—H4···O2ii | 0.93 | 2.53 | 3.368 (4) | 149 |
C67—H672···N32iii | 0.96 | 2.53 | 3.445 (5) | 160 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x−3/2, −y−1/2, z−1/2. |