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The title compounds, 10-benzoylamino-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione monohydrate, C20H20N2O3·H2O, and 10-p-toluoylamino-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione monohydrate, C21H22N2O3·H2O, consist of partially hydrogenated acridine moieties with one benzoylamino substituent on the central ring. The acridine moiety suffers considerable deviations from planarity. The central ring in the acridine moiety is a boat, while the outer rings adopt sofa conformations.
Supporting information
CCDC references: 150776; 150777
Data collection: SMART (Siemens, 1996) for (I). Cell refinement: SAINT (Siemens, 1996) for (I). Data reduction: SAINT for (I). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for (I); SHELXS97 (Sheldrick, 1990) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983, 1995).
(I) 10-(benzoylamino)-3,4,6,7,9,10-hexahydro-1,8-(2
H,5H)-acridinedione (I)
top
Crystal data top
C20H20N2O3·H2O | F(000) = 752 |
Mr = 354.40 | Dx = 1.279 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4056 (2) Å | Cell parameters from 6167 reflections |
b = 12.2501 (1) Å | θ = 1.8–28.3° |
c = 13.1746 (3) Å | µ = 0.09 mm−1 |
β = 91.497 (1)° | T = 293 K |
V = 1840.12 (5) Å3 | Slab, yellow |
Z = 4 | 0.48 × 0.40 × 0.08 mm |
Data collection top
Siemens SMART CCD area detector Diffractometer | 3066 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 28.4°, θmin = 1.8° |
Detector resolution: 8.33 pixels mm-1 | h = −15→13 |
ω scans | k = −15→16 |
12199 measured reflections | l = −15→17 |
4512 independent reflections | |
Refinement top
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.03 | Calculated w = 1/[σ2(Fo2) + (0.0755P)2 + 0.5302P] where P = (Fo2 + 2Fc2)/3 |
4512 reflections | (Δ/σ)max < 0.001 |
243 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Special details top
Experimental. Data were collected over a hemisphere of reciproal space, by a combination of
three sets of exposures. Each set had a different φ angle (0, 88 and 180 °)
for the crystal and each exposure of 30 s(I) and (II) covered 0.3° in ω. The
crystal-to-detector distance was 4 cm (I) and (II) the detector swing angle
was -35°. Coverage of the unique set is over 99% complete. The first 30
frames of data were recollected at the end of data collection to monitor
crystal decay. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.23695 (13) | 0.72286 (15) | −0.12058 (14) | 0.0765 (5) | |
O2 | 0.94941 (15) | 0.44042 (15) | −0.25585 (12) | 0.0753 (5) | |
O3 | 0.71019 (13) | 0.83820 (13) | −0.03779 (10) | 0.0628 (4) | |
C1 | 1.16121 (17) | 0.75573 (17) | −0.06314 (16) | 0.0530 (5) | |
C1A | 1.05034 (15) | 0.69651 (15) | −0.05398 (13) | 0.0421 (4) | |
C2 | 1.1774 (2) | 0.8579 (2) | −0.0029 (2) | 0.0729 (7) | |
H2A | 1.1501 | 0.9194 | −0.0434 | 0.088* | |
H2B | 1.2604 | 0.8684 | 0.0119 | 0.088* | |
C3 | 1.1133 (2) | 0.8566 (2) | 0.0950 (2) | 0.0802 (8) | |
H3A | 1.1188 | 0.9283 | 0.1258 | 0.096* | |
H3B | 1.1516 | 0.8052 | 0.1410 | 0.096* | |
C4 | 0.98483 (18) | 0.82563 (18) | 0.08270 (17) | 0.0589 (5) | |
H4A | 0.9544 | 0.8068 | 0.1485 | 0.071* | |
H4B | 0.9408 | 0.8879 | 0.0568 | 0.071* | |
C4A | 0.96784 (15) | 0.73105 (14) | 0.01163 (13) | 0.0418 (4) | |
C5 | 0.87640 (18) | 0.47744 (17) | −0.19661 (15) | 0.0539 (5) | |
C5A | 0.90911 (15) | 0.55826 (15) | −0.12073 (13) | 0.0427 (4) | |
C6 | 0.7503 (2) | 0.4434 (2) | −0.2046 (2) | 0.0749 (7) | |
H6A | 0.7461 | 0.3694 | −0.2307 | 0.090* | |
H6B | 0.7095 | 0.4905 | −0.2530 | 0.090* | |
C7 | 0.6883 (2) | 0.4478 (2) | −0.1055 (2) | 0.0771 (7) | |
H7A | 0.7173 | 0.3891 | −0.0622 | 0.093* | |
H7B | 0.6052 | 0.4356 | −0.1183 | 0.093* | |
C8 | 0.70433 (18) | 0.55438 (18) | −0.05035 (18) | 0.0596 (5) | |
H8A | 0.6518 | 0.6083 | −0.0805 | 0.072* | |
H8B | 0.6833 | 0.5449 | 0.0200 | 0.072* | |
C8A | 0.82820 (15) | 0.59571 (15) | −0.05409 (13) | 0.0420 (4) | |
C9 | 1.03328 (16) | 0.59835 (17) | −0.12132 (14) | 0.0485 (4) | |
H9A | 1.0535 | 0.6172 | −0.1902 | 0.058* | |
H9B | 1.0855 | 0.5404 | −0.0982 | 0.058* | |
N10 | 0.85975 (12) | 0.67670 (13) | 0.01556 (11) | 0.0455 (4) | |
N11 | 0.77321 (13) | 0.71683 (13) | 0.08003 (11) | 0.0468 (4) | |
H11 | 0.7667 | 0.6907 | 0.1402 | 0.056* | |
C12 | 0.70035 (15) | 0.79687 (15) | 0.04634 (13) | 0.0448 (4) | |
C13 | 0.60590 (14) | 0.82915 (15) | 0.11858 (13) | 0.0421 (4) | |
C14 | 0.55390 (16) | 0.93074 (17) | 0.10426 (15) | 0.0503 (4) | |
H14 | 0.5800 | 0.9770 | 0.0536 | 0.060* | |
C15 | 0.46231 (18) | 0.96351 (19) | 0.16583 (17) | 0.0590 (5) | |
H15 | 0.4276 | 1.0315 | 0.1557 | 0.071* | |
C16 | 0.42296 (17) | 0.8957 (2) | 0.24160 (17) | 0.0619 (6) | |
H16 | 0.3613 | 0.9176 | 0.2817 | 0.074* | |
C17 | 0.47542 (19) | 0.7956 (2) | 0.25751 (18) | 0.0650 (6) | |
H17 | 0.4501 | 0.7504 | 0.3092 | 0.078* | |
C18 | 0.56660 (17) | 0.76214 (17) | 0.19593 (17) | 0.0551 (5) | |
H18 | 0.6014 | 0.6943 | 0.2067 | 0.066* | |
O1W | 0.18109 (18) | 0.1329 (2) | 0.22943 (13) | 0.0907 (7) | |
HWA | 0.108 (3) | 0.113 (2) | 0.230 (2) | 0.084 (9)* | |
HWB | 0.204 (3) | 0.152 (3) | 0.169 (3) | 0.100 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0532 (9) | 0.0927 (12) | 0.0853 (12) | −0.0016 (8) | 0.0344 (8) | −0.0126 (10) |
O2 | 0.0673 (10) | 0.0932 (12) | 0.0659 (10) | 0.0120 (8) | 0.0077 (8) | −0.0333 (9) |
O3 | 0.0659 (9) | 0.0797 (10) | 0.0437 (7) | 0.0212 (8) | 0.0186 (6) | 0.0158 (7) |
C1 | 0.0469 (10) | 0.0619 (12) | 0.0509 (10) | 0.0031 (9) | 0.0133 (8) | 0.0060 (9) |
C1A | 0.0408 (9) | 0.0508 (10) | 0.0351 (8) | 0.0088 (7) | 0.0073 (6) | 0.0032 (7) |
C2 | 0.0644 (14) | 0.0745 (15) | 0.0809 (16) | −0.0154 (12) | 0.0201 (12) | −0.0113 (13) |
C3 | 0.0730 (16) | 0.0899 (18) | 0.0785 (16) | −0.0181 (13) | 0.0203 (12) | −0.0283 (15) |
C4 | 0.0568 (12) | 0.0592 (12) | 0.0615 (12) | 0.0016 (9) | 0.0150 (9) | −0.0142 (10) |
C4A | 0.0422 (9) | 0.0456 (9) | 0.0378 (8) | 0.0075 (7) | 0.0072 (7) | 0.0031 (7) |
C5 | 0.0547 (11) | 0.0589 (11) | 0.0479 (10) | 0.0120 (9) | −0.0010 (8) | −0.0061 (9) |
C5A | 0.0443 (9) | 0.0483 (9) | 0.0355 (8) | 0.0116 (7) | 0.0029 (7) | 0.0014 (7) |
C6 | 0.0633 (14) | 0.0833 (16) | 0.0777 (16) | 0.0006 (12) | −0.0061 (12) | −0.0240 (14) |
C7 | 0.0605 (14) | 0.0816 (16) | 0.0895 (18) | −0.0084 (12) | 0.0052 (12) | −0.0146 (14) |
C8 | 0.0459 (11) | 0.0681 (13) | 0.0653 (13) | 0.0023 (9) | 0.0097 (9) | −0.0065 (11) |
C8A | 0.0418 (9) | 0.0465 (9) | 0.0380 (8) | 0.0084 (7) | 0.0037 (7) | 0.0032 (7) |
C9 | 0.0433 (9) | 0.0632 (11) | 0.0394 (9) | 0.0117 (8) | 0.0091 (7) | −0.0050 (8) |
N10 | 0.0391 (7) | 0.0565 (9) | 0.0415 (7) | 0.0075 (6) | 0.0140 (6) | −0.0053 (7) |
N11 | 0.0439 (8) | 0.0601 (9) | 0.0372 (7) | 0.0128 (7) | 0.0153 (6) | 0.0018 (7) |
C12 | 0.0413 (9) | 0.0534 (10) | 0.0402 (9) | 0.0055 (8) | 0.0101 (7) | 0.0008 (8) |
C13 | 0.0338 (8) | 0.0518 (10) | 0.0411 (8) | 0.0031 (7) | 0.0076 (6) | −0.0030 (8) |
C14 | 0.0455 (10) | 0.0581 (11) | 0.0475 (10) | 0.0080 (8) | 0.0065 (8) | 0.0038 (9) |
C15 | 0.0489 (11) | 0.0645 (12) | 0.0639 (12) | 0.0166 (9) | 0.0073 (9) | −0.0068 (10) |
C16 | 0.0426 (10) | 0.0802 (15) | 0.0636 (13) | 0.0080 (10) | 0.0194 (9) | −0.0093 (11) |
C17 | 0.0524 (12) | 0.0765 (14) | 0.0675 (13) | 0.0016 (10) | 0.0296 (10) | 0.0088 (11) |
C18 | 0.0477 (10) | 0.0547 (11) | 0.0640 (12) | 0.0064 (8) | 0.0218 (9) | 0.0082 (9) |
O1W | 0.0780 (12) | 0.1477 (19) | 0.0473 (9) | −0.0488 (13) | 0.0173 (8) | −0.0219 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.231 (2) | C7—C8 | 1.503 (3) |
O2—C5 | 1.242 (2) | C7—H7A | 0.9700 |
O3—C12 | 1.226 (2) | C7—H7B | 0.9700 |
C1—C1A | 1.465 (3) | C8—C8A | 1.503 (3) |
C1—C2 | 1.491 (3) | C8—H8A | 0.9700 |
C1A—C4A | 1.362 (2) | C8—H8B | 0.9700 |
C1A—C9 | 1.504 (3) | C8A—N10 | 1.392 (2) |
C2—C3 | 1.499 (3) | C9—H9A | 0.9700 |
C2—H2A | 0.9700 | C9—H9B | 0.9700 |
C2—H2B | 0.9700 | N10—N11 | 1.4075 (18) |
C3—C4 | 1.518 (3) | N11—C12 | 1.353 (2) |
C3—H3A | 0.9700 | N11—H11 | 0.8600 |
C3—H3B | 0.9700 | C12—C13 | 1.509 (2) |
C4—C4A | 1.499 (3) | C13—C14 | 1.389 (3) |
C4—H4A | 0.9700 | C13—C18 | 1.392 (3) |
C4—H4B | 0.9700 | C14—C15 | 1.398 (3) |
C4A—N10 | 1.403 (2) | C14—H14 | 0.9300 |
C5—C5A | 1.449 (3) | C15—C16 | 1.383 (3) |
C5—C6 | 1.499 (3) | C15—H15 | 0.9300 |
C5A—C8A | 1.369 (2) | C16—C17 | 1.378 (3) |
C5A—C9 | 1.499 (3) | C16—H16 | 0.9300 |
C6—C7 | 1.501 (4) | C17—C18 | 1.397 (3) |
C6—H6A | 0.9700 | C17—H17 | 0.9300 |
C6—H6B | 0.9700 | C18—H18 | 0.9300 |
| | | |
O1—C1—C1A | 120.64 (19) | H7A—C7—H7B | 107.7 |
O1—C1—C2 | 121.50 (19) | C8A—C8—C7 | 112.28 (17) |
C1A—C1—C2 | 117.84 (17) | C8A—C8—H8A | 109.1 |
C4A—C1A—C1 | 120.70 (17) | C7—C8—H8A | 109.1 |
C4A—C1A—C9 | 122.82 (16) | C8A—C8—H8B | 109.1 |
C1—C1A—C9 | 116.47 (15) | C7—C8—H8B | 109.1 |
C1—C2—C3 | 113.1 (2) | H8A—C8—H8B | 107.9 |
C1—C2—H2A | 109.0 | C5A—C8A—N10 | 119.63 (16) |
C3—C2—H2A | 109.0 | C5A—C8A—C8 | 123.92 (17) |
C1—C2—H2B | 109.0 | N10—C8A—C8 | 116.45 (15) |
C3—C2—H2B | 109.0 | C5A—C9—C1A | 111.50 (14) |
H2A—C2—H2B | 107.8 | C5A—C9—H9A | 109.3 |
C2—C3—C4 | 113.7 (2) | C1A—C9—H9A | 109.3 |
C2—C3—H3A | 108.8 | C5A—C9—H9B | 109.3 |
C4—C3—H3A | 108.8 | C1A—C9—H9B | 109.3 |
C2—C3—H3B | 108.8 | H9A—C9—H9B | 108.0 |
C4—C3—H3B | 108.8 | C8A—N10—C4A | 121.74 (14) |
H3A—C3—H3B | 107.7 | C8A—N10—N11 | 118.25 (14) |
C4A—C4—C3 | 111.61 (17) | C4A—N10—N11 | 119.15 (15) |
C4A—C4—H4A | 109.3 | C12—N11—N10 | 119.32 (14) |
C3—C4—H4A | 109.3 | C12—N11—H11 | 120.3 |
C4A—C4—H4B | 109.3 | N10—N11—H11 | 120.3 |
C3—C4—H4B | 109.3 | O3—C12—N11 | 121.73 (16) |
H4A—C4—H4B | 108.0 | O3—C12—C13 | 123.07 (16) |
C1A—C4A—N10 | 119.89 (16) | N11—C12—C13 | 115.20 (15) |
C1A—C4A—C4 | 123.81 (17) | C14—C13—C18 | 118.90 (16) |
N10—C4A—C4 | 116.30 (15) | C14—C13—C12 | 117.28 (16) |
O2—C5—C5A | 121.22 (19) | C18—C13—C12 | 123.79 (16) |
O2—C5—C6 | 120.83 (19) | C13—C14—C15 | 120.08 (19) |
C5A—C5—C6 | 117.89 (17) | C13—C14—H14 | 120.0 |
C8A—C5A—C5 | 120.37 (17) | C15—C14—H14 | 120.0 |
C8A—C5A—C9 | 123.10 (16) | C16—C15—C14 | 120.54 (19) |
C5—C5A—C9 | 116.52 (15) | C16—C15—H15 | 119.7 |
C5—C6—C7 | 113.70 (19) | C14—C15—H15 | 119.7 |
C5—C6—H6A | 108.8 | C17—C16—C15 | 119.77 (18) |
C7—C6—H6A | 108.8 | C17—C16—H16 | 120.1 |
C5—C6—H6B | 108.8 | C15—C16—H16 | 120.1 |
C7—C6—H6B | 108.8 | C16—C17—C18 | 120.0 (2) |
H6A—C6—H6B | 107.7 | C16—C17—H17 | 120.0 |
C6—C7—C8 | 113.4 (2) | C18—C17—H17 | 120.0 |
C6—C7—H7A | 108.9 | C13—C18—C17 | 120.71 (19) |
C8—C7—H7A | 108.9 | C13—C18—H18 | 119.6 |
C6—C7—H7B | 108.9 | C17—C18—H18 | 119.6 |
C8—C7—H7B | 108.9 | | |
| | | |
O1—C1—C1A—C4A | 178.15 (19) | C8A—C5A—C9—C1A | −10.1 (2) |
C2—C1—C1A—C4A | −3.4 (3) | C5—C5A—C9—C1A | 168.82 (15) |
O1—C1—C1A—C9 | −2.7 (3) | C4A—C1A—C9—C5A | 10.5 (2) |
C2—C1—C1A—C9 | 175.76 (19) | C1—C1A—C9—C5A | −168.61 (16) |
O1—C1—C2—C3 | −151.0 (2) | C5A—C8A—N10—C4A | 8.0 (3) |
C1A—C1—C2—C3 | 30.5 (3) | C8—C8A—N10—C4A | −172.16 (17) |
C1—C2—C3—C4 | −51.0 (3) | C5A—C8A—N10—N11 | 177.27 (15) |
C2—C3—C4—C4A | 43.4 (3) | C8—C8A—N10—N11 | −2.9 (2) |
C1—C1A—C4A—N10 | 176.68 (16) | C1A—C4A—N10—C8A | −7.6 (3) |
C9—C1A—C4A—N10 | −2.4 (3) | C4—C4A—N10—C8A | 172.72 (16) |
C1—C1A—C4A—C4 | −3.7 (3) | C1A—C4A—N10—N11 | −176.78 (15) |
C9—C1A—C4A—C4 | 177.25 (17) | C4—C4A—N10—N11 | 3.5 (2) |
C3—C4—C4A—C1A | −16.5 (3) | C8A—N10—N11—C12 | −84.2 (2) |
C3—C4—C4A—N10 | 163.2 (2) | C4A—N10—N11—C12 | 85.3 (2) |
O2—C5—C5A—C8A | −178.04 (19) | N10—N11—C12—O3 | −2.6 (3) |
C6—C5—C5A—C8A | 4.6 (3) | N10—N11—C12—C13 | 176.27 (15) |
O2—C5—C5A—C9 | 3.0 (3) | O3—C12—C13—C14 | −21.3 (3) |
C6—C5—C5A—C9 | −174.36 (19) | N11—C12—C13—C14 | 159.89 (17) |
O2—C5—C6—C7 | 151.7 (2) | O3—C12—C13—C18 | 156.9 (2) |
C5A—C5—C6—C7 | −31.0 (3) | N11—C12—C13—C18 | −21.9 (3) |
C5—C6—C7—C8 | 50.0 (3) | C18—C13—C14—C15 | −1.1 (3) |
C6—C7—C8—C8A | −42.0 (3) | C12—C13—C14—C15 | 177.21 (18) |
C5—C5A—C8A—N10 | −177.31 (16) | C13—C14—C15—C16 | 0.3 (3) |
C9—C5A—C8A—N10 | 1.6 (3) | C14—C15—C16—C17 | 0.9 (3) |
C5—C5A—C8A—C8 | 2.9 (3) | C15—C16—C17—C18 | −1.2 (4) |
C9—C5A—C8A—C8 | −178.24 (18) | C14—C13—C18—C17 | 0.8 (3) |
C7—C8—C8A—C5A | 16.2 (3) | C12—C13—C18—C17 | −177.4 (2) |
C7—C8—C8A—N10 | −163.60 (19) | C16—C17—C18—C13 | 0.4 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O1Wi | 0.86 | 1.94 | 2.750 (2) | 157 |
C16—H16···O1ii | 0.93 | 2.59 | 3.180 (3) | 122 |
C17—H17···O1ii | 0.93 | 2.64 | 3.203 (3) | 119 |
C18—H18···O1Wi | 0.93 | 2.71 | 3.407 (3) | 133 |
O1W—HWA···O2iii | 0.87 | 1.937 | 2.802 (3) | 173.9 |
O1W—HWB···O3iv | 0.88 | 2.012 | 2.864 (2) | 163.7 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, −y+3/2, z+1/2; (iii) x−1, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z. |
(II) 10-(4-methylbenzoylamino)-3,4,6,7,9,10-hexahydro-1,8-(2
H,5H)-acridinedione(II)
top
Crystal data top
C21H22N2O3·H2O | F(000) = 1568 |
Mr = 368.42 | Dx = 1.258 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.2343 (10) Å | Cell parameters from 6666 reflections |
b = 13.8327 (6) Å | θ = 1.9–28.3° |
c = 16.3286 (7) Å | µ = 0.09 mm−1 |
β = 132.140 (1)° | T = 293 K |
V = 3891.4 (3) Å3 | Block, yellow |
Z = 8 | 0.48 × 0.44 × 0.36 mm |
Data collection top
Siemens SMART CCD area detector Diffractometer | 2634 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
Detector resolution: 8.33 pixels mm-1 | h = −27→20 |
ω scans | k = −14→16 |
10281 measured reflections | l = −19→19 |
3424 independent reflections | |
Refinement top
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | Constrained(execpt water molecule) |
S = 0.95 | Calculated w = 1/[σ2(Fo2) + (0.1225P)2 + 2.3517P] where P = (Fo2 + 2Fc2)/3 |
3424 reflections | (Δ/σ)max = 0.003 |
253 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.19154 (13) | 0.35055 (13) | 0.14221 (17) | 0.0917 (6) | |
O2 | 0.14732 (16) | 0.41574 (14) | 0.39752 (19) | 0.1088 (8) | |
O3 | 0.01368 (10) | 0.01930 (11) | 0.11193 (14) | 0.0711 (5) | |
O1W | 0.27048 (12) | −0.07556 (15) | 0.47128 (16) | 0.0761 (5) | |
HWA | 0.3006 (18) | −0.025 (2) | 0.509 (3) | 0.085 (9)* | |
HWB | 0.294 (2) | −0.098 (2) | 0.446 (3) | 0.114 (12)* | |
C1 | 0.19224 (15) | 0.26294 (18) | 0.1572 (2) | 0.0676 (6) | |
C1A | 0.17132 (13) | 0.22895 (14) | 0.21847 (17) | 0.0558 (5) | |
C2 | 0.2088 (2) | 0.1891 (2) | 0.1077 (3) | 0.0911 (9) | |
H2A | 0.1614 | 0.1763 | 0.0322 | 0.109* | |
H2B | 0.2464 | 0.2156 | 0.1055 | 0.109* | |
C3 | 0.2390 (2) | 0.0973 (2) | 0.1697 (3) | 0.0950 (9) | |
H3A | 0.2910 | 0.1077 | 0.2403 | 0.114* | |
H3B | 0.2423 | 0.0502 | 0.1290 | 0.114* | |
C4 | 0.18877 (16) | 0.05684 (17) | 0.1894 (2) | 0.0677 (6) | |
H4A | 0.1416 | 0.0303 | 0.1210 | 0.081* | |
H4B | 0.2162 | 0.0048 | 0.2429 | 0.081* | |
C4A | 0.16805 (12) | 0.13331 (14) | 0.23127 (16) | 0.0527 (5) | |
C5 | 0.13821 (16) | 0.32860 (19) | 0.4007 (2) | 0.0752 (7) | |
C5A | 0.14027 (12) | 0.26131 (16) | 0.33461 (17) | 0.0573 (5) | |
C6 | 0.1286 (3) | 0.2902 (3) | 0.4756 (3) | 0.1134 (12) | |
H6A | 0.1781 | 0.2955 | 0.5508 | 0.136* | |
H6B | 0.0921 | 0.3313 | 0.4695 | 0.136* | |
C7 | 0.1032 (3) | 0.1953 (3) | 0.4580 (4) | 0.153 (2) | |
H7A | 0.0471 | 0.1974 | 0.4081 | 0.183* | |
H7B | 0.1220 | 0.1710 | 0.5280 | 0.183* | |
C8 | 0.12297 (17) | 0.12158 (19) | 0.4140 (2) | 0.0735 (7) | |
H8A | 0.0813 | 0.0746 | 0.3709 | 0.088* | |
H8B | 0.1697 | 0.0877 | 0.4752 | 0.088* | |
C8A | 0.13548 (11) | 0.16539 (15) | 0.34328 (16) | 0.0522 (5) | |
C9 | 0.14962 (18) | 0.30370 (16) | 0.2601 (2) | 0.0739 (7) | |
H9A | 0.1895 | 0.3532 | 0.2999 | 0.089* | |
H9B | 0.1014 | 0.3343 | 0.1978 | 0.089* | |
N10 | 0.14564 (11) | 0.10201 (11) | 0.28778 (15) | 0.0575 (5) | |
N11 | 0.13047 (11) | 0.00379 (11) | 0.28438 (15) | 0.0568 (5) | |
H11 | 0.1626 | −0.0326 | 0.3410 | 0.068* | |
C12 | 0.06327 (12) | −0.03293 (14) | 0.18885 (16) | 0.0510 (5) | |
C13 | 0.05681 (11) | −0.13969 (14) | 0.18533 (15) | 0.0481 (5) | |
C14 | 0.01321 (13) | −0.18396 (16) | 0.08280 (18) | 0.0620 (6) | |
H14 | −0.0110 | −0.1465 | 0.0199 | 0.074* | |
C15 | 0.00567 (15) | −0.28268 (17) | 0.0739 (2) | 0.0698 (6) | |
H15 | −0.0231 | −0.3112 | 0.0047 | 0.084* | |
C16 | 0.03971 (14) | −0.34104 (16) | 0.1652 (2) | 0.0673 (6) | |
C17 | 0.08318 (16) | −0.29647 (17) | 0.2667 (2) | 0.0740 (7) | |
H17 | 0.1069 | −0.3340 | 0.3294 | 0.089* | |
C18 | 0.09226 (14) | −0.19757 (16) | 0.27738 (18) | 0.0639 (6) | |
H18 | 0.1224 | −0.1694 | 0.3470 | 0.077* | |
C19 | 0.0291 (2) | −0.44942 (19) | 0.1527 (3) | 0.1095 (12) | |
H19A | 0.0484 | −0.4740 | 0.1199 | 0.164* | |
H19B | −0.0250 | −0.4647 | 0.1062 | 0.164* | |
H19C | 0.0573 | −0.4784 | 0.2240 | 0.164* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1211 (16) | 0.0650 (11) | 0.0996 (14) | −0.0179 (10) | 0.0784 (13) | 0.0095 (10) |
O2 | 0.156 (2) | 0.0601 (12) | 0.1017 (15) | 0.0000 (12) | 0.0827 (16) | −0.0231 (10) |
O3 | 0.0722 (10) | 0.0569 (9) | 0.0708 (10) | 0.0182 (8) | 0.0425 (9) | 0.0156 (8) |
O1W | 0.0780 (11) | 0.0680 (11) | 0.0724 (11) | 0.0048 (9) | 0.0464 (10) | −0.0097 (9) |
C1 | 0.0706 (14) | 0.0634 (14) | 0.0644 (14) | −0.0104 (11) | 0.0434 (12) | 0.0054 (11) |
C1A | 0.0644 (12) | 0.0465 (11) | 0.0515 (11) | −0.0038 (9) | 0.0368 (10) | 0.0009 (8) |
C2 | 0.118 (2) | 0.089 (2) | 0.114 (2) | −0.0013 (17) | 0.097 (2) | 0.0096 (17) |
C3 | 0.123 (2) | 0.086 (2) | 0.129 (3) | 0.0077 (17) | 0.106 (2) | 0.0054 (18) |
C4 | 0.0876 (16) | 0.0526 (13) | 0.0862 (16) | 0.0046 (11) | 0.0679 (15) | 0.0018 (11) |
C4A | 0.0583 (11) | 0.0478 (11) | 0.0529 (11) | −0.0002 (9) | 0.0377 (10) | 0.0010 (8) |
C5 | 0.0818 (16) | 0.0657 (16) | 0.0636 (14) | 0.0055 (12) | 0.0428 (13) | −0.0125 (11) |
C5A | 0.0573 (12) | 0.0529 (12) | 0.0492 (11) | −0.0014 (9) | 0.0306 (10) | −0.0081 (9) |
C6 | 0.163 (4) | 0.104 (3) | 0.115 (3) | 0.021 (2) | 0.110 (3) | −0.005 (2) |
C7 | 0.257 (6) | 0.129 (3) | 0.206 (5) | −0.084 (3) | 0.210 (5) | −0.082 (3) |
C8 | 0.0814 (16) | 0.0799 (17) | 0.0794 (16) | −0.0027 (13) | 0.0622 (14) | −0.0007 (13) |
C8A | 0.0501 (11) | 0.0533 (12) | 0.0489 (11) | −0.0005 (9) | 0.0314 (9) | −0.0033 (8) |
C9 | 0.109 (2) | 0.0422 (11) | 0.0741 (15) | −0.0055 (12) | 0.0629 (15) | −0.0046 (10) |
N10 | 0.0808 (12) | 0.0381 (9) | 0.0689 (11) | −0.0011 (8) | 0.0564 (10) | 0.0005 (8) |
N11 | 0.0708 (11) | 0.0383 (9) | 0.0604 (10) | 0.0004 (7) | 0.0437 (10) | 0.0058 (7) |
C12 | 0.0597 (12) | 0.0465 (11) | 0.0575 (12) | 0.0079 (9) | 0.0437 (11) | 0.0071 (9) |
C13 | 0.0487 (10) | 0.0468 (11) | 0.0525 (11) | 0.0026 (8) | 0.0356 (9) | 0.0043 (8) |
C14 | 0.0615 (12) | 0.0590 (13) | 0.0505 (11) | 0.0041 (10) | 0.0314 (10) | 0.0065 (9) |
C15 | 0.0710 (15) | 0.0594 (14) | 0.0594 (13) | −0.0045 (11) | 0.0357 (12) | −0.0071 (10) |
C16 | 0.0658 (13) | 0.0497 (12) | 0.0764 (15) | −0.0026 (10) | 0.0436 (12) | 0.0009 (11) |
C17 | 0.0856 (17) | 0.0538 (13) | 0.0682 (15) | −0.0027 (11) | 0.0457 (14) | 0.0146 (11) |
C18 | 0.0748 (14) | 0.0577 (13) | 0.0523 (12) | −0.0067 (10) | 0.0398 (12) | 0.0034 (9) |
C19 | 0.127 (3) | 0.0533 (16) | 0.121 (3) | −0.0095 (16) | 0.072 (2) | −0.0022 (16) |
Geometric parameters (Å, º) top
O1—C1 | 1.234 (3) | C7—H7B | 0.9700 |
O2—C5 | 1.231 (3) | C8—C8A | 1.495 (3) |
O3—C12 | 1.219 (2) | C8—H8A | 0.9700 |
C1—C1A | 1.453 (3) | C8—H8B | 0.9700 |
C1—C2 | 1.504 (4) | C8A—N10 | 1.390 (3) |
C1A—C4A | 1.350 (3) | C9—H9A | 0.9700 |
C1A—C9 | 1.499 (3) | C9—H9B | 0.9700 |
C2—C3 | 1.476 (4) | N10—N11 | 1.395 (2) |
C2—H2A | 0.9700 | N11—C12 | 1.364 (3) |
C2—H2B | 0.9700 | N11—H11 | 0.8600 |
C3—C4 | 1.511 (4) | C12—C13 | 1.482 (3) |
C3—H3A | 0.9700 | C13—C18 | 1.385 (3) |
C3—H3B | 0.9700 | C13—C14 | 1.389 (3) |
C4—C4A | 1.503 (3) | C14—C15 | 1.372 (3) |
C4—H4A | 0.9700 | C14—H14 | 0.9300 |
C4—H4B | 0.9700 | C15—C16 | 1.384 (3) |
C4A—N10 | 1.398 (3) | C15—H15 | 0.9300 |
C5—C5A | 1.450 (3) | C16—C17 | 1.379 (3) |
C5—C6 | 1.480 (5) | C16—C19 | 1.511 (3) |
C5A—C8A | 1.347 (3) | C17—C18 | 1.377 (3) |
C5A—C9 | 1.491 (3) | C17—H17 | 0.9300 |
C6—C7 | 1.389 (5) | C18—H18 | 0.9300 |
C6—H6A | 0.9700 | C19—H19A | 0.9600 |
C6—H6B | 0.9700 | C19—H19B | 0.9600 |
C7—C8 | 1.487 (4) | C19—H19C | 0.9600 |
C7—H7A | 0.9700 | | |
| | | |
O1—C1—C1A | 119.2 (2) | C8A—C8—H8A | 109.2 |
O1—C1—C2 | 122.3 (2) | C7—C8—H8B | 109.2 |
C1A—C1—C2 | 118.4 (2) | C8A—C8—H8B | 109.2 |
C4A—C1A—C1 | 120.2 (2) | H8A—C8—H8B | 107.9 |
C4A—C1A—C9 | 122.3 (2) | C5A—C8A—N10 | 119.38 (19) |
C1—C1A—C9 | 117.34 (19) | C5A—C8A—C8 | 123.6 (2) |
C3—C2—C1 | 113.0 (2) | N10—C8A—C8 | 116.99 (19) |
C3—C2—H2A | 109.0 | C5A—C9—C1A | 112.11 (18) |
C1—C2—H2A | 109.0 | C5A—C9—H9A | 109.2 |
C3—C2—H2B | 109.0 | C1A—C9—H9A | 109.2 |
C1—C2—H2B | 109.0 | C5A—C9—H9B | 109.2 |
H2A—C2—H2B | 107.8 | C1A—C9—H9B | 109.2 |
C2—C3—C4 | 112.7 (3) | H9A—C9—H9B | 107.9 |
C2—C3—H3A | 109.1 | C8A—N10—N11 | 119.41 (17) |
C4—C3—H3A | 109.1 | C8A—N10—C4A | 122.43 (16) |
C2—C3—H3B | 109.1 | N11—N10—C4A | 118.12 (16) |
C4—C3—H3B | 109.1 | C12—N11—N10 | 118.22 (17) |
H3A—C3—H3B | 107.8 | C12—N11—H11 | 120.9 |
C4A—C4—C3 | 111.4 (2) | N10—N11—H11 | 120.9 |
C4A—C4—H4A | 109.3 | O3—C12—N11 | 121.54 (19) |
C3—C4—H4A | 109.3 | O3—C12—C13 | 123.35 (19) |
C4A—C4—H4B | 109.3 | N11—C12—C13 | 115.09 (16) |
C3—C4—H4B | 109.3 | C18—C13—C14 | 118.37 (19) |
H4A—C4—H4B | 108.0 | C18—C13—C12 | 124.28 (18) |
C1A—C4A—N10 | 119.36 (19) | C14—C13—C12 | 117.34 (17) |
C1A—C4A—C4 | 123.5 (2) | C15—C14—C13 | 120.3 (2) |
N10—C4A—C4 | 117.18 (17) | C15—C14—H14 | 119.9 |
O2—C5—C5A | 120.3 (3) | C13—C14—H14 | 119.9 |
O2—C5—C6 | 120.8 (2) | C14—C15—C16 | 121.8 (2) |
C5A—C5—C6 | 118.9 (3) | C14—C15—H15 | 119.1 |
C8A—C5A—C5 | 120.5 (2) | C16—C15—H15 | 119.1 |
C8A—C5A—C9 | 122.71 (19) | C17—C16—C15 | 117.5 (2) |
C5—C5A—C9 | 116.8 (2) | C17—C16—C19 | 121.9 (2) |
C7—C6—C5 | 116.6 (3) | C15—C16—C19 | 120.6 (2) |
C7—C6—H6A | 108.1 | C18—C17—C16 | 121.5 (2) |
C5—C6—H6A | 108.1 | C18—C17—H17 | 119.3 |
C7—C6—H6B | 108.1 | C16—C17—H17 | 119.3 |
C5—C6—H6B | 108.1 | C17—C18—C13 | 120.5 (2) |
H6A—C6—H6B | 107.3 | C17—C18—H18 | 119.7 |
C6—C7—C8 | 121.5 (3) | C13—C18—H18 | 119.7 |
C6—C7—H7A | 107.0 | C16—C19—H19A | 109.5 |
C8—C7—H7A | 107.0 | C16—C19—H19B | 109.5 |
C6—C7—H7B | 107.0 | H19A—C19—H19B | 109.5 |
C8—C7—H7B | 107.0 | C16—C19—H19C | 109.5 |
H7A—C7—H7B | 106.7 | H19A—C19—H19C | 109.5 |
C7—C8—C8A | 112.2 (2) | H19B—C19—H19C | 109.5 |
C7—C8—H8A | 109.2 | | |
| | | |
O1—C1—C1A—C4A | 176.8 (2) | C5—C5A—C9—C1A | 165.3 (2) |
C2—C1—C1A—C4A | 0.9 (3) | C4A—C1A—C9—C5A | 11.4 (3) |
O1—C1—C1A—C9 | 0.1 (3) | C1—C1A—C9—C5A | −172.0 (2) |
C2—C1—C1A—C9 | −175.8 (2) | C5A—C8A—N10—N11 | −171.42 (19) |
O1—C1—C2—C3 | 155.7 (3) | C8—C8A—N10—N11 | 11.1 (3) |
C1A—C1—C2—C3 | −28.5 (4) | C5A—C8A—N10—C4A | 6.2 (3) |
C1—C2—C3—C4 | 51.7 (4) | C8—C8A—N10—C4A | −171.2 (2) |
C2—C3—C4—C4A | −47.1 (4) | C1A—C4A—N10—C8A | −8.0 (3) |
C1—C1A—C4A—N10 | −178.2 (2) | C4—C4A—N10—C8A | 171.0 (2) |
C9—C1A—C4A—N10 | −1.7 (3) | C1A—C4A—N10—N11 | 169.70 (19) |
C1—C1A—C4A—C4 | 2.9 (3) | C4—C4A—N10—N11 | −11.4 (3) |
C9—C1A—C4A—C4 | 179.4 (2) | C8A—N10—N11—C12 | 103.8 (2) |
C3—C4—C4A—C1A | 20.2 (3) | C4A—N10—N11—C12 | −74.0 (2) |
C3—C4—C4A—N10 | −158.7 (2) | N10—N11—C12—O3 | −7.5 (3) |
O2—C5—C5A—C8A | 175.6 (2) | N10—N11—C12—C13 | 170.87 (17) |
C6—C5—C5A—C8A | −1.6 (4) | O3—C12—C13—C18 | −152.9 (2) |
O2—C5—C5A—C9 | −3.1 (4) | N11—C12—C13—C18 | 28.8 (3) |
C6—C5—C5A—C9 | 179.7 (3) | O3—C12—C13—C14 | 28.2 (3) |
O2—C5—C6—C7 | 167.4 (4) | N11—C12—C13—C14 | −150.11 (19) |
C5A—C5—C6—C7 | −15.4 (5) | C18—C13—C14—C15 | 0.2 (3) |
C5—C6—C7—C8 | 31.1 (7) | C12—C13—C14—C15 | 179.2 (2) |
C6—C7—C8—C8A | −27.9 (6) | C13—C14—C15—C16 | 1.0 (4) |
C5—C5A—C8A—N10 | −173.4 (2) | C14—C15—C16—C17 | −1.2 (4) |
C9—C5A—C8A—N10 | 5.2 (3) | C14—C15—C16—C19 | 178.8 (3) |
C5—C5A—C8A—C8 | 3.9 (3) | C15—C16—C17—C18 | 0.3 (4) |
C9—C5A—C8A—C8 | −177.5 (2) | C19—C16—C17—C18 | −179.7 (3) |
C7—C8—C8A—C5A | 9.7 (4) | C16—C17—C18—C13 | 0.8 (4) |
C7—C8—C8A—N10 | −173.0 (3) | C14—C13—C18—C17 | −1.1 (3) |
C8A—C5A—C9—C1A | −13.3 (3) | C12—C13—C18—C17 | 180.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O1W | 0.86 | 2.00 | 2.789 (2) | 152 |
C8—H8A···O3i | 0.97 | 2.52 | 3.234 (1) | 130 |
O1W—HWB···O1ii | 0.93 | 1.828 | 2.730 (5) | 162.0 |
O1W—HWA···O2iii | 0.88 | 1.897 | 2.763 (3) | 166.2 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, −y+1/2, −z+1. |
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