Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101003171/sk1458sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101003171/sk1458BCCMsup2.hkl |
CCDC reference: 166983
For related literature, see: Abrahams & Keve (1971); Bertolasi et al. (1984); Codding et al. (1988); International (1969); Muir & Codding (1985).
The compound was provided by Drs R. Coutts and R. Micetish of the Faculty of Pharmacy, University of Alberta. Colourless prismatic crystals were grown from the ethanol solution by slow evaporation.
Hydrogen atoms of the methyl group in molecule A were found to be disordered over two positions with site occupation factors of 0.5 each. The positional parameters of all these hydrogen atoms were refined, as was one common isotropic displacement parameter for each three-atom group.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: ENPROC (Rettig, 1978); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens, 1989).
C13H10N2O2 | F(000) = 944 |
Mr = 226.23 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 9.6550 (5) Å | Cell parameters from 25 reflections |
b = 20.8077 (8) Å | θ = 10–38° |
c = 11.0793 (5) Å | µ = 0.78 mm−1 |
β = 102.388 (5)° | T = 293 K |
V = 2173.99 (16) Å3 | Prism, colourless |
Z = 8 | 0.35 × 0.25 × 0.2 mm |
CAD4-F four-circle diffractometer | Rint = 0.019 |
Radiation source: fine-focus sealed tube | θmax = 69.9°, θmin = 4.3° |
Ni-filter monochromator | h = −8→11 |
ω/2θ scans | k = −25→25 |
8604 measured reflections | l = −13→11 |
4113 independent reflections | 2 standard reflections every 33 min |
3280 reflections with I > 2σ(I) | intensity decay: 2% |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | All H-atom parameters refined |
S = 1.22 | w = 1/[σ2(Fo2) + (0.030P)2 + 0.1443P] where P = (Fo2 + 2Fc2)/3 |
4113 reflections | (Δ/σ)max < 0.001 |
393 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C13H10N2O2 | V = 2173.99 (16) Å3 |
Mr = 226.23 | Z = 8 |
Monoclinic, P21/c | Cu Kα radiation |
a = 9.6550 (5) Å | µ = 0.78 mm−1 |
b = 20.8077 (8) Å | T = 293 K |
c = 11.0793 (5) Å | 0.35 × 0.25 × 0.2 mm |
β = 102.388 (5)° |
CAD4-F four-circle diffractometer | Rint = 0.019 |
8604 measured reflections | 2 standard reflections every 33 min |
4113 independent reflections | intensity decay: 2% |
3280 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.099 | All H-atom parameters refined |
S = 1.22 | Δρmax = 0.15 e Å−3 |
4113 reflections | Δρmin = −0.19 e Å−3 |
393 parameters |
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 | Occ. (<1) | |
C1AA | 0.77699 (15) | 0.49647 (7) | 0.50226 (13) | 0.0521 (3) | |
C1A | 0.73661 (17) | 0.45891 (7) | 0.39661 (15) | 0.0592 (4) | |
H1A | 0.7903 (18) | 0.4230 (8) | 0.3806 (16) | 0.074 (5)* | |
N2A | 0.62048 (14) | 0.47172 (6) | 0.31164 (11) | 0.0592 (3) | |
C3A | 0.54165 (15) | 0.52333 (7) | 0.32979 (13) | 0.0522 (3) | |
C31A | 0.41510 (16) | 0.53548 (7) | 0.22854 (14) | 0.0561 (4) | |
O31A | 0.38630 (13) | 0.50624 (6) | 0.13295 (10) | 0.0748 (3) | |
O32A | 0.33677 (12) | 0.58386 (5) | 0.25567 (10) | 0.0683 (3) | |
C32A | 0.2134 (2) | 0.60102 (11) | 0.1633 (2) | 0.0745 (5) | |
H32A | 0.176 (3) | 0.6431 (16) | 0.191 (3) | 0.049 (5)* | 0.50 |
H32B | 0.145 (3) | 0.5643 (16) | 0.152 (3) | 0.049 (5)* | 0.50 |
H32C | 0.245 (3) | 0.6096 (17) | 0.079 (3) | 0.049 (5)* | 0.50 |
H32D | 0.195 (4) | 0.5658 (19) | 0.105 (3) | 0.066 (6)* | 0.50 |
H32E | 0.231 (4) | 0.6424 (18) | 0.128 (3) | 0.066 (6)* | 0.50 |
H32F | 0.134 (4) | 0.6128 (19) | 0.213 (3) | 0.066 (6)* | 0.50 |
C4A | 0.57249 (15) | 0.56282 (7) | 0.43218 (13) | 0.0501 (3) | |
H4A | 0.5096 (16) | 0.5994 (7) | 0.4373 (13) | 0.058 (4)* | |
C4AA | 0.69294 (14) | 0.54895 (6) | 0.52184 (13) | 0.0488 (3) | |
C4BA | 0.75996 (15) | 0.57647 (6) | 0.63938 (13) | 0.0511 (3) | |
C5A | 0.72662 (18) | 0.62666 (7) | 0.71074 (15) | 0.0623 (4) | |
H5A | 0.6412 (19) | 0.6526 (8) | 0.6803 (15) | 0.078 (5)* | |
C6A | 0.8158 (2) | 0.63965 (8) | 0.82222 (16) | 0.0718 (5) | |
H6A | 0.7921 (19) | 0.6744 (9) | 0.8724 (17) | 0.087 (6)* | |
C7A | 0.9394 (2) | 0.60391 (9) | 0.86258 (17) | 0.0751 (5) | |
H7A | 0.997 (2) | 0.6125 (9) | 0.9405 (17) | 0.083 (5)* | |
C8A | 0.97481 (18) | 0.55386 (8) | 0.79472 (16) | 0.0683 (4) | |
H8A | 1.057 (2) | 0.5279 (9) | 0.8212 (16) | 0.082 (5)* | |
C8AA | 0.88343 (15) | 0.53972 (7) | 0.68287 (14) | 0.0540 (3) | |
N9A | 0.89173 (13) | 0.49179 (6) | 0.59924 (12) | 0.0584 (3) | |
H9A | 0.952 (2) | 0.4592 (9) | 0.6120 (17) | 0.083 (6)* | |
C1AB | 0.37615 (17) | 0.38237 (7) | 0.93274 (14) | 0.0574 (4) | |
C1B | 0.26108 (19) | 0.42080 (8) | 0.87921 (16) | 0.0661 (4) | |
H1B | 0.2412 (18) | 0.4608 (8) | 0.9178 (16) | 0.076 (5)* | |
N2B | 0.17707 (14) | 0.40581 (6) | 0.77217 (12) | 0.0615 (3) | |
C3B | 0.20684 (15) | 0.35219 (7) | 0.71339 (13) | 0.0521 (3) | |
C31B | 0.10855 (16) | 0.33938 (7) | 0.59329 (14) | 0.0549 (3) | |
O31B | 0.00621 (12) | 0.37134 (5) | 0.54957 (11) | 0.0717 (3) | |
O32B | 0.14493 (12) | 0.28749 (5) | 0.53749 (10) | 0.0681 (3) | |
C32B | 0.0522 (2) | 0.26920 (11) | 0.42285 (18) | 0.0763 (5) | |
H32G | 0.090 (2) | 0.2303 (11) | 0.390 (2) | 0.113 (4)* | |
H32H | −0.039 (3) | 0.2599 (11) | 0.440 (2) | 0.113 (4)* | |
H32I | 0.037 (2) | 0.3055 (11) | 0.371 (2) | 0.113 (4)* | |
C4B | 0.31840 (15) | 0.31121 (7) | 0.75957 (13) | 0.0527 (3) | |
H4B | 0.3351 (16) | 0.2737 (7) | 0.7120 (14) | 0.058 (4)* | |
C4AB | 0.40378 (15) | 0.32572 (7) | 0.87352 (13) | 0.0521 (3) | |
C4BB | 0.52446 (15) | 0.29591 (7) | 0.95351 (13) | 0.0539 (3) | |
C5B | 0.59907 (17) | 0.23912 (8) | 0.94830 (16) | 0.0646 (4) | |
H5B | 0.5732 (18) | 0.2105 (8) | 0.8750 (16) | 0.073 (5)* | |
C6B | 0.7106 (2) | 0.22462 (10) | 1.04429 (19) | 0.0798 (5) | |
H6B | 0.765 (2) | 0.1860 (9) | 1.0412 (17) | 0.094 (6)* | |
C7B | 0.7502 (2) | 0.26656 (11) | 1.14316 (18) | 0.0859 (6) | |
H7B | 0.829 (2) | 0.2531 (10) | 1.2069 (19) | 0.107 (7)* | |
C8B | 0.6794 (2) | 0.32285 (10) | 1.15115 (16) | 0.0756 (5) | |
H8B | 0.701 (2) | 0.3536 (9) | 1.2174 (18) | 0.095 (6)* | |
C8AB | 0.56401 (17) | 0.33713 (8) | 1.05600 (14) | 0.0592 (4) | |
N9B | 0.47373 (15) | 0.38910 (7) | 1.04178 (12) | 0.0655 (4) | |
H9B | 0.4765 (19) | 0.4214 (9) | 1.0940 (17) | 0.078 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1AA | 0.0498 (8) | 0.0507 (7) | 0.0550 (8) | −0.0004 (6) | 0.0093 (6) | 0.0031 (6) |
C1A | 0.0596 (9) | 0.0541 (8) | 0.0627 (9) | 0.0065 (7) | 0.0107 (7) | −0.0044 (7) |
N2A | 0.0617 (8) | 0.0574 (7) | 0.0568 (7) | 0.0010 (6) | 0.0091 (6) | −0.0052 (6) |
C3A | 0.0510 (8) | 0.0530 (8) | 0.0507 (8) | −0.0036 (6) | 0.0069 (6) | 0.0012 (6) |
C31A | 0.0578 (9) | 0.0561 (8) | 0.0519 (8) | −0.0064 (7) | 0.0062 (7) | 0.0001 (7) |
O31A | 0.0799 (8) | 0.0788 (8) | 0.0568 (6) | 0.0035 (6) | −0.0052 (6) | −0.0121 (6) |
O32A | 0.0611 (7) | 0.0725 (7) | 0.0620 (6) | 0.0106 (5) | −0.0078 (5) | −0.0064 (5) |
C32A | 0.0649 (11) | 0.0762 (13) | 0.0712 (12) | 0.0074 (10) | −0.0101 (9) | 0.0060 (10) |
C4A | 0.0467 (7) | 0.0496 (7) | 0.0518 (8) | −0.0008 (6) | 0.0053 (6) | 0.0013 (6) |
C4AA | 0.0478 (7) | 0.0472 (7) | 0.0505 (7) | −0.0022 (6) | 0.0083 (6) | 0.0014 (6) |
C4BA | 0.0484 (7) | 0.0480 (7) | 0.0533 (8) | −0.0013 (6) | 0.0031 (6) | 0.0019 (6) |
C5A | 0.0604 (9) | 0.0566 (9) | 0.0629 (9) | 0.0064 (7) | −0.0022 (7) | −0.0054 (7) |
C6A | 0.0790 (12) | 0.0642 (10) | 0.0629 (10) | 0.0047 (9) | −0.0054 (9) | −0.0119 (8) |
C7A | 0.0756 (12) | 0.0741 (11) | 0.0612 (10) | 0.0015 (9) | −0.0171 (9) | −0.0047 (9) |
C8A | 0.0580 (9) | 0.0679 (10) | 0.0688 (10) | 0.0072 (8) | −0.0090 (8) | 0.0044 (8) |
C8AA | 0.0496 (8) | 0.0508 (8) | 0.0580 (8) | 0.0002 (6) | 0.0036 (7) | 0.0043 (6) |
N9A | 0.0505 (7) | 0.0574 (7) | 0.0634 (8) | 0.0088 (6) | 0.0035 (6) | 0.0018 (6) |
C1AB | 0.0616 (9) | 0.0582 (8) | 0.0508 (8) | −0.0006 (7) | 0.0088 (7) | −0.0017 (6) |
C1B | 0.0742 (11) | 0.0581 (9) | 0.0634 (10) | 0.0097 (8) | 0.0091 (8) | −0.0062 (7) |
N2B | 0.0622 (8) | 0.0562 (7) | 0.0634 (8) | 0.0061 (6) | 0.0072 (6) | 0.0007 (6) |
C3B | 0.0513 (8) | 0.0487 (7) | 0.0546 (8) | −0.0009 (6) | 0.0078 (6) | 0.0031 (6) |
C31B | 0.0519 (8) | 0.0486 (7) | 0.0616 (9) | −0.0005 (6) | 0.0066 (7) | 0.0059 (6) |
O31B | 0.0585 (6) | 0.0648 (7) | 0.0809 (8) | 0.0101 (5) | −0.0090 (6) | −0.0046 (5) |
O32B | 0.0704 (7) | 0.0660 (7) | 0.0587 (6) | 0.0117 (5) | −0.0069 (5) | −0.0064 (5) |
C32B | 0.0745 (11) | 0.0843 (13) | 0.0614 (10) | 0.0016 (10) | −0.0045 (9) | −0.0105 (9) |
C4B | 0.0534 (8) | 0.0492 (8) | 0.0532 (8) | −0.0007 (6) | 0.0062 (7) | −0.0007 (6) |
C4AB | 0.0511 (8) | 0.0516 (8) | 0.0525 (8) | −0.0016 (6) | 0.0090 (6) | 0.0013 (6) |
C4BB | 0.0501 (8) | 0.0591 (8) | 0.0502 (8) | −0.0024 (6) | 0.0053 (6) | 0.0007 (6) |
C5B | 0.0543 (9) | 0.0669 (9) | 0.0667 (10) | 0.0050 (7) | 0.0003 (7) | −0.0073 (8) |
C6B | 0.0629 (10) | 0.0817 (12) | 0.0843 (13) | 0.0152 (9) | −0.0075 (9) | −0.0040 (10) |
C7B | 0.0743 (12) | 0.0966 (14) | 0.0715 (12) | 0.0089 (11) | −0.0180 (10) | −0.0029 (10) |
C8B | 0.0768 (12) | 0.0856 (12) | 0.0561 (10) | −0.0032 (10) | −0.0043 (9) | −0.0084 (9) |
C8AB | 0.0606 (9) | 0.0656 (9) | 0.0501 (8) | −0.0043 (7) | 0.0087 (7) | −0.0013 (7) |
N9B | 0.0742 (9) | 0.0650 (8) | 0.0537 (7) | 0.0030 (7) | 0.0057 (7) | −0.0105 (6) |
C1AA—N9A | 1.371 (2) | N9A—H9A | 0.88 (2) |
C1AA—C1A | 1.392 (2) | C1AB—N9B | 1.370 (2) |
C1AA—C4AA | 1.405 (2) | C1AB—C1B | 1.394 (2) |
C1A—N2A | 1.327 (2) | C1AB—C4AB | 1.402 (2) |
C1A—H1A | 0.95 (2) | C1B—N2B | 1.322 (2) |
N2A—C3A | 1.356 (2) | C1B—H1B | 0.97 (2) |
C3A—C4A | 1.380 (2) | N2B—C3B | 1.353 (2) |
C3A—C31A | 1.492 (2) | C3B—C4B | 1.383 (2) |
C31A—O31A | 1.201 (2) | C3B—C31B | 1.483 (2) |
C31A—O32A | 1.332 (2) | C31B—O31B | 1.203 (2) |
O32A—C32A | 1.439 (2) | C31B—O32B | 1.328 (2) |
C32A—H32A | 1.02 (3) | O32B—C32B | 1.439 (2) |
C32A—H32B | 1.00 (3) | C32B—H32G | 0.99 (2) |
C32A—H32C | 1.06 (3) | C32B—H32H | 0.96 (2) |
C32A—H32D | 0.97 (4) | C32B—H32I | 0.94 (2) |
C32A—H32E | 0.98 (4) | C4B—C4AB | 1.385 (2) |
C32A—H32F | 1.07 (4) | C4B—H4B | 0.98 (2) |
C4A—C4AA | 1.388 (2) | C4AB—C4BB | 1.444 (2) |
C4A—H4A | 0.98 (2) | C4BB—C5B | 1.392 (2) |
C4AA—C4BA | 1.443 (2) | C4BB—C8AB | 1.409 (2) |
C4BA—C5A | 1.389 (2) | C5B—C6B | 1.375 (2) |
C4BA—C8AA | 1.411 (2) | C5B—H5B | 1.00 (2) |
C5A—C6A | 1.372 (2) | C6B—C7B | 1.389 (3) |
C5A—H5A | 0.98 (2) | C6B—H6B | 0.96 (2) |
C6A—C7A | 1.396 (2) | C7B—C8B | 1.369 (3) |
C6A—H6A | 0.97 (2) | C7B—H7B | 0.96 (2) |
C7A—C8A | 1.370 (3) | C8B—C8AB | 1.392 (2) |
C7A—H7A | 0.94 (2) | C8B—H8B | 0.96 (2) |
C8A—C8AA | 1.390 (2) | C8AB—N9B | 1.377 (2) |
C8A—H8A | 0.95 (2) | N9B—H9B | 0.88 (2) |
C8AA—N9A | 1.375 (2) | ||
N9A—C1AA—C1A | 130.7 (1) | C1AA—N9A—H9A | 125 (1) |
N9A—C1AA—C4AA | 109.3 (1) | C8AA—N9A—H9A | 125 (1) |
C1A—C1AA—C4AA | 120.0 (1) | N9B—C1AB—C1B | 130.6 (1) |
N2A—C1A—C1AA | 121.7 (1) | N9B—C1AB—C4AB | 109.5 (1) |
N2A—C1A—H1A | 116 (1) | C1B—C1AB—C4AB | 119.8 (1) |
C1AA—C1A—H1A | 122 (1) | N2B—C1B—C1AB | 121.7 (1) |
C1A—N2A—C3A | 118.0 (1) | N2B—C1B—H1B | 117 (1) |
N2A—C3A—C4A | 124.4 (1) | C1AB—C1B—H1B | 121 (1) |
N2A—C3A—C31A | 114.7 (1) | C1B—N2B—C3B | 118.2 (1) |
C4A—C3A—C31A | 121.0 (1) | N2B—C3B—C4B | 124.0 (1) |
O31A—C31A—O32A | 123.1 (1) | N2B—C3B—C31B | 114.8 (1) |
O31A—C31A—C3A | 125.1 (1) | C4B—C3B—C31B | 121.2 (1) |
O32A—C31A—C3A | 111.8 (1) | O31B—C31B—O32B | 122.6 (1) |
C31A—O32A—C32A | 116.8 (1) | O31B—C31B—C3B | 125.0 (1) |
O32A—C32A—H32A | 107 (2) | O32B—C31B—C3B | 112.4 (1) |
O32A—C32A—H32B | 109 (2) | C31B—O32B—C32B | 116.7 (1) |
H32A—C32A—H32B | 115 (3) | O32B—C32B—H32G | 109 (1) |
O32A—C32A—H32C | 108 (2) | O32B—C32B—H32H | 108 (1) |
H32A—C32A—H32C | 108 (2) | H32G—C32B—H32H | 109 (2) |
H32B—C32A—H32C | 109 (2) | O32B—C32B—H32I | 108 (1) |
O32A—C32A—H32D | 107 (2) | H32G—C32B—H32I | 117 (2) |
H32D—C32A—H32E | 115 (3) | H32H—C32B—H32I | 105 (2) |
O32A—C32A—H32F | 105 (2) | C3B—C4B—C4AB | 117.8 (1) |
H32D—C32A—H32F | 118 (3) | C3B—C4B—H4B | 120.9 (9) |
H32E—C32A—H32F | 102 (3) | C4AB—C4B—H4B | 122.2 (9) |
C3A—C4A—C4AA | 117.7 (1) | C4B—C4AB—C1AB | 118.3 (1) |
C3A—C4A—H4A | 118.7 (9) | C4B—C4AB—C4BB | 135.2 (1) |
C4AA—C4A—H4A | 123.6 (9) | C1AB—C4AB—C4BB | 106.5 (1) |
C4A—C4AA—C1AA | 118.3 (1) | C5B—C4BB—C8AB | 119.8 (1) |
C4A—C4AA—C4BA | 135.1 (1) | C5B—C4BB—C4AB | 134.1 (1) |
C1AA—C4AA—C4BA | 106.6 (1) | C8AB—C4BB—C4AB | 106.1 (1) |
C5A—C4BA—C8AA | 119.7 (1) | C6B—C5B—C4BB | 118.7 (2) |
C5A—C4BA—C4AA | 134.3 (1) | C6B—C5B—H5B | 121 (1) |
C8AA—C4BA—C4AA | 106.0 (1) | C4BB—C5B—H5B | 120 (1) |
C6A—C5A—C4BA | 118.9 (1) | C5B—C6B—C7B | 120.6 (2) |
C6A—C5A—H5A | 121 (1) | C5B—C6B—H6B | 120 (1) |
C4BA—C5A—H5A | 120 (1) | C7B—C6B—H6B | 119 (1) |
C5A—C6A—C7A | 120.8 (2) | C8B—C7B—C6B | 122.1 (2) |
C5A—C6A—H6A | 119 (1) | C8B—C7B—H7B | 122 (1) |
C7A—C6A—H6A | 120 (1) | C6B—C7B—H7B | 116 (1) |
C8A—C7A—C6A | 121.7 (2) | C7B—C8B—C8AB | 117.6 (2) |
C8A—C7A—H7A | 119 (1) | C7B—C8B—H8B | 126 (1) |
C6A—C7A—H7A | 120 (1) | C8AB—C8B—H8B | 116 (1) |
C7A—C8A—C8AA | 117.7 (2) | N9B—C8AB—C8B | 129.7 (1) |
C7A—C8A—H8A | 123 (1) | N9B—C8AB—C4BB | 109.3 (1) |
C8AA—C8A—H8A | 119 (1) | C8B—C8AB—C4BB | 121.0 (2) |
N9A—C8AA—C8A | 129.5 (1) | C1AB—N9B—C8AB | 108.6 (1) |
N9A—C8AA—C4BA | 109.3 (1) | C1AB—N9B—H9B | 125 (1) |
C8A—C8AA—C4BA | 121.2 (1) | C8AB—N9B—H9B | 126 (1) |
C1AA—N9A—C8AA | 108.8 (1) | ||
N9A—C1AA—C1A—N2A | −179.5 (1) | N9B—C1AB—C1B—N2B | −179.4 (2) |
C4AA—C1AA—C1A—N2A | 0.9 (2) | C4AB—C1AB—C1B—N2B | −0.9 (3) |
C1AA—C1A—N2A—C3A | 0.6 (2) | C1AB—C1B—N2B—C3B | −1.2 (2) |
C1A—N2A—C3A—C4A | −1.4 (2) | C1B—N2B—C3B—C4B | 1.4 (2) |
C1A—N2A—C3A—C31A | 178.4 (1) | C1B—N2B—C3B—C31B | −179.2 (1) |
N2A—C3A—C31A—O31A | −5.2 (2) | N2B—C3B—C31B—O31B | −2.5 (2) |
C4A—C3A—C31A—O31A | 174.6 (1) | C4B—C3B—C31B—O31B | 176.9 (1) |
N2A—C3A—C31A—O32A | 175.6 (1) | N2B—C3B—C31B—O32B | 177.9 (1) |
C4A—C3A—C31A—O32A | −4.6 (2) | C4B—C3B—C31B—O32B | −2.6 (2) |
O31A—C31A—O32A—C32A | −0.7 (2) | O31B—C31B—O32B—C32B | −2.4 (2) |
C3A—C31A—O32A—C32A | 178.5 (1) | C3B—C31B—O32B—C32B | 177.1 (1) |
N2A—C3A—C4A—C4AA | 0.6 (2) | N2B—C3B—C4B—C4AB | 0.7 (2) |
C31A—C3A—C4A—C4AA | −179.2 (1) | C31B—C3B—C4B—C4AB | −178.7 (1) |
C3A—C4A—C4AA—C1AA | 1.0 (2) | C3B—C4B—C4AB—C1AB | −2.7 (2) |
C3A—C4A—C4AA—C4BA | −179.0 (1) | C3B—C4B—C4AB—C4BB | 178.1 (1) |
N9A—C1AA—C4AA—C4A | 178.6 (1) | N9B—C1AB—C4AB—C4B | −178.3 (1) |
C1A—C1AA—C4AA—C4A | −1.7 (2) | C1B—C1AB—C4AB—C4B | 2.9 (2) |
N9A—C1AA—C4AA—C4BA | −1.4 (2) | N9B—C1AB—C4AB—C4BB | 1.1 (2) |
C1A—C1AA—C4AA—C4BA | 178.3 (1) | C1B—C1AB—C4AB—C4BB | −177.7 (1) |
C4A—C4AA—C4BA—C5A | 2.7 (3) | C4B—C4AB—C4BB—C5B | −2.7 (3) |
C1AA—C4AA—C4BA—C5A | −177.3 (2) | C1AB—C4AB—C4BB—C5B | 178.1 (2) |
C4A—C4AA—C4BA—C8AA | −178.6 (1) | C4B—C4AB—C4BB—C8AB | 178.4 (2) |
C1AA—C4AA—C4BA—C8AA | 1.4 (1) | C1AB—C4AB—C4BB—C8AB | −0.9 (2) |
C8AA—C4BA—C5A—C6A | 0.5 (2) | C8AB—C4BB—C5B—C6B | 0.0 (2) |
C4AA—C4BA—C5A—C6A | 179.0 (2) | C4AB—C4BB—C5B—C6B | −178.9 (2) |
C4BA—C5A—C6A—C7A | 1.2 (3) | C4BB—C5B—C6B—C7B | −1.5 (3) |
C5A—C6A—C7A—C8A | −1.6 (3) | C5B—C6B—C7B—C8B | 1.4 (3) |
C6A—C7A—C8A—C8AA | 0.3 (3) | C6B—C7B—C8B—C8AB | 0.2 (3) |
C7A—C8A—C8AA—N9A | −178.3 (2) | C7B—C8B—C8AB—N9B | 178.8 (2) |
C7A—C8A—C8AA—C4BA | 1.3 (3) | C7B—C8B—C8AB—C4BB | −1.8 (3) |
C5A—C4BA—C8AA—N9A | 178.0 (1) | C5B—C4BB—C8AB—N9B | −178.7 (1) |
C4AA—C4BA—C8AA—N9A | −1.0 (2) | C4AB—C4BB—C8AB—N9B | 0.4 (2) |
C5A—C4BA—C8AA—C8A | −1.7 (2) | C5B—C4BB—C8AB—C8B | 1.7 (2) |
C4AA—C4BA—C8AA—C8A | 179.3 (1) | C4AB—C4BB—C8AB—C8B | −179.1 (1) |
C1A—C1AA—N9A—C8AA | −178.9 (2) | C1B—C1AB—N9B—C8AB | 177.8 (2) |
C4AA—C1AA—N9A—C8AA | 0.8 (2) | C4AB—C1AB—N9B—C8AB | −0.9 (2) |
C8A—C8AA—N9A—C1AA | 179.8 (2) | C8B—C8AB—N9B—C1AB | 179.8 (2) |
C4BA—C8AA—N9A—C1AA | 0.1 (2) | C4BB—C8AB—N9B—C1AB | 0.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N9A—H9A···O31Bi | 0.88 (2) | 2.06 (2) | 2.840 (2) | 146 (2) |
N9A—H9A···N2Bi | 0.88 (2) | 2.73 (2) | 3.492 (2) | 145 (1) |
N9B—H9B···O31Aii | 0.88 (2) | 2.05 (2) | 2.835 (2) | 147 (2) |
N9B—H9B···N2Aii | 0.88 (2) | 2.72 (2) | 3.476 (2) | 144 (1) |
C6A—H6A···O32Biii | 0.97 (2) | 2.58 (2) | 3.431 (2) | 147 (1) |
C6B—H6B···O31Biv | 0.96 (2) | 2.61 (2) | 3.473 (2) | 150 (1) |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) x+1, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H10N2O2 |
Mr | 226.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.6550 (5), 20.8077 (8), 11.0793 (5) |
β (°) | 102.388 (5) |
V (Å3) | 2173.99 (16) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.78 |
Crystal size (mm) | 0.35 × 0.25 × 0.2 |
Data collection | |
Diffractometer | CAD4-F four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8604, 4113, 3280 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.099, 1.22 |
No. of reflections | 4113 |
No. of parameters | 393 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.15, −0.19 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, ENPROC (Rettig, 1978), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Stereochemical Workstation (Siemens, 1989).
C1AA—N9A | 1.371 (2) | C1AB—N9B | 1.370 (2) |
C1A—N2A | 1.327 (2) | C1B—N2B | 1.322 (2) |
N2A—C3A | 1.356 (2) | N2B—C3B | 1.353 (2) |
C31A—O31A | 1.201 (2) | C31B—O31B | 1.203 (2) |
C8AA—N9A | 1.375 (2) | C8AB—N9B | 1.377 (2) |
C1A—N2A—C3A | 118.0 (1) | C1B—N2B—C3B | 118.2 (1) |
C1AA—N9A—C8AA | 108.8 (1) | C1AB—N9B—C8AB | 108.6 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
N9A—H9A···O31Bi | 0.88 (2) | 2.06 (2) | 2.840 (2) | 146 (2) |
N9A—H9A···N2Bi | 0.88 (2) | 2.73 (2) | 3.492 (2) | 145 (1) |
N9B—H9B···O31Aii | 0.88 (2) | 2.05 (2) | 2.835 (2) | 147 (2) |
N9B—H9B···N2Aii | 0.88 (2) | 2.72 (2) | 3.476 (2) | 144 (1) |
C6A—H6A···O32Biii | 0.97 (2) | 2.58 (2) | 3.431 (2) | 147 (1) |
C6B—H6B···O31Biv | 0.96 (2) | 2.61 (2) | 3.473 (2) | 150 (1) |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) −x+1, y+1/2, −z+3/2; (iv) x+1, −y+1/2, z+1/2. |
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The crystal structure of monoclinic methyl β-carboline-3-carboxylate (hereinafter referred to as BCCM) was reported twice (Bertolasi et al., 1984, hereinafter BFGB; Muir & Codding, 1985, hereinafter MC). Both independent determinations were of comparable quality (reported R factors are 0.058 and 0.049 for BFGB and MC, respectively), and they described exactly the same form of BCCM: monoclinic P21/c, with the mean values of the unit-cell parameters equal: a = 11.477 (2) Å, b = 5.806 (1) Å, c = 32.400 (4) Å, β = 97.11 (2)°, and Z = 8 (i.e. there are two symmetry- independent molecules in the asymmetric part of the unit cell). \sch
The discussion of the biological activity of β-carbolines and similar compounds at benzodiaepine receptor as well as the results of structure activity studies of these compunds can be found in Codding et al. (1988). Here, we report the crystal and molecular structure of another monoclinic form of BCCM (Fig. 1). The different unit cell [a = 9.6550 (5) Å, b = 20.8077 (8) Å, c = 11.0793 (5) Å, β = 102.388 (5)°] of the same space group P21/c also contains eight molecules of BCCM, very similar to those reported earlier. The bond lengths and angles patterns agree within the experimental error, and on the basis of the results of normal probability plot (Abrahams & Keve, 1971, International Tables for X-Ray Crystallography, 1969) it can be stated that the differences are of random rather than systematical nature. In both molecules three fused rings are essentially coplanar (maximum deviations are 0.040 (2) and 0.051 (2) Å for molecules A and B, respectively), and the methyl carboxylate groups are close to coplanarity with the carboline planes [the appropriate dihedral angles are 3.9 (1) and 5.0 (1)° for both symmetry-independent molecules].
The hydrogen-bonding scheme is exactly the same in both forms: the molecules form infinite, planar sheets that expand along the axis of the length of ca 13 Å ([110] in BFGB and MC, [101] in present case, Fig. 2). It might be noted that only the unit-cell translation are used in formation of the sheet and the inter-sheet interactions are weak, mainly of the van der Waals nature, and therefore there is certain degree of flexibility in the orientation of the sheets with respect to the symmetry elements, hence the two forms are possible within the same space group. In the present case the neighbouring, non-coplanar sheets are joined by weak C6—H6···O hydrogen bonds, while in MC and BFGB the weak C—H···O hydrogen bonds connect the parallel sheets into a centrosymmetric bilayer. This may also explain the large differences in the unit-cell parameters in MC and BFGB (longest to shortest unit-cell parameter ratio of ca 6) as compared to the present form (the ratio of 2).
The geometrical parameters of strong hydrogen bonds are quite similar; the only remarkable difference is a lack of the asymmetry between N—H···O bonds in the present case, and consequently, much longer N—H···N contacts and the absence of a "slip of one molecule past the other in the hydrogen-bonding plane" (Muir & Codding, 1985).