Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031552/hk2101sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031552/hk2101Isup2.hkl |
CCDC reference: 621363
Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-STEP32 (Stoe & Cie, 2000); software used to prepare material for publication: SHELXL97.
C19H18N2O2 | F(000) = 648 |
Mr = 306.35 | Dx = 1.282 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2550 reflections |
a = 9.463 (2) Å | θ = 2.4–26.7° |
b = 16.550 (3) Å | µ = 0.08 mm−1 |
c = 10.607 (2) Å | T = 294 K |
β = 107.191 (16)° | Block, colorless |
V = 1587.0 (6) Å3 | 0.35 × 0.3 × 0.2 mm |
Z = 4 |
Stoe IPDS-II diffractometer | 2827 reflections with I > 2σ(I) |
ω ? φ ? scans | Rint = 0.028 |
Absorption correction: numerical (shape of crystal determined optically; reference? | θmax = 26.7°, θmin = 2.4° |
Tmin = 0.971, Tmax = 0.983 | h = −11→11 |
12022 measured reflections | k = −20→20 |
3365 independent reflections | l = −12→13 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0483P)2 + 0.4305P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.112 | (Δ/σ)max = 0.003 |
S = 1.09 | Δρmax = 0.18 e Å−3 |
3365 reflections | Δρmin = −0.18 e Å−3 |
280 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.2708 (2) | 0.06715 (12) | 0.7317 (2) | 0.0593 (5) | |
H1A | 1.320 (3) | 0.0156 (15) | 0.745 (2) | 0.080 (7)* | |
H1B | 1.337 (3) | 0.1115 (18) | 0.710 (3) | 0.106 (9)* | |
H1C | 1.251 (3) | 0.0836 (17) | 0.816 (3) | 0.099 (9)* | |
C2 | 1.03936 (15) | 0.12050 (8) | 0.57734 (13) | 0.0314 (3) | |
C3 | 0.99091 (15) | 0.26761 (8) | 0.57532 (13) | 0.0327 (3) | |
H3 | 0.8957 (17) | 0.2465 (9) | 0.5198 (15) | 0.035 (4)* | |
C4 | 0.96298 (15) | 0.31746 (8) | 0.68567 (13) | 0.0321 (3) | |
C5 | 1.07704 (16) | 0.33658 (8) | 0.79687 (14) | 0.0359 (3) | |
C6 | 1.0518 (2) | 0.38032 (10) | 0.90235 (16) | 0.0470 (4) | |
H6 | 1.135 (2) | 0.3905 (12) | 0.980 (2) | 0.060 (5)* | |
C7 | 0.9137 (2) | 0.40701 (11) | 0.89436 (17) | 0.0508 (4) | |
H7 | 0.899 (2) | 0.4369 (13) | 0.967 (2) | 0.064 (6)* | |
C8 | 0.79352 (18) | 0.39294 (9) | 0.78036 (17) | 0.0437 (4) | |
C9 | 0.6504 (2) | 0.42408 (12) | 0.7686 (2) | 0.0589 (5) | |
H9 | 0.642 (2) | 0.4532 (15) | 0.844 (2) | 0.078 (7)* | |
C10 | 0.5367 (2) | 0.41246 (15) | 0.6580 (3) | 0.0711 (6) | |
H10 | 0.439 (3) | 0.4357 (15) | 0.652 (2) | 0.086 (7)* | |
C11 | 0.5596 (2) | 0.36919 (13) | 0.5522 (2) | 0.0657 (5) | |
H11 | 0.480 (3) | 0.3605 (14) | 0.472 (2) | 0.077 (7)* | |
C12 | 0.69555 (17) | 0.33750 (10) | 0.55943 (18) | 0.0465 (4) | |
H12 | 0.710 (2) | 0.3085 (11) | 0.4845 (18) | 0.051 (5)* | |
C13 | 0.81801 (16) | 0.34785 (8) | 0.67437 (14) | 0.0356 (3) | |
C14 | 1.05820 (16) | 0.31507 (8) | 0.48355 (14) | 0.0358 (3) | |
C15 | 1.0788 (3) | 0.27646 (11) | 0.3745 (2) | 0.0646 (6) | |
H15 | 1.060 (3) | 0.2207 (16) | 0.366 (2) | 0.086 (7)* | |
C16 | 1.1373 (3) | 0.31706 (13) | 0.2877 (2) | 0.0774 (7) | |
H16 | 1.150 (3) | 0.2904 (18) | 0.209 (3) | 0.113 (9)* | |
C17 | 1.1757 (2) | 0.39716 (12) | 0.3077 (2) | 0.0596 (5) | |
H17 | 1.223 (2) | 0.4255 (14) | 0.249 (2) | 0.078 (7)* | |
C18 | 1.1536 (2) | 0.43642 (11) | 0.41359 (18) | 0.0540 (4) | |
H18 | 1.180 (2) | 0.4927 (15) | 0.431 (2) | 0.078 (6)* | |
C19 | 1.09456 (19) | 0.39581 (9) | 0.50039 (17) | 0.0448 (4) | |
H19 | 1.077 (2) | 0.4239 (13) | 0.574 (2) | 0.069 (6)* | |
N1 | 1.13332 (14) | 0.05972 (7) | 0.62789 (13) | 0.0414 (3) | |
H1D | 1.1066 (19) | 0.0113 (11) | 0.5928 (17) | 0.048 (5)* | |
N2 | 1.07799 (14) | 0.19482 (7) | 0.62622 (12) | 0.0379 (3) | |
H2A | 1.163 (2) | 0.2023 (11) | 0.6828 (18) | 0.050 (5)* | |
O1 | 0.92115 (11) | 0.10606 (6) | 0.48890 (11) | 0.0423 (3) | |
O2 | 1.21690 (12) | 0.31167 (7) | 0.80280 (11) | 0.0450 (3) | |
H2B | 1.283 (2) | 0.3362 (13) | 0.867 (2) | 0.070 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0513 (10) | 0.0398 (9) | 0.0637 (12) | 0.0112 (8) | −0.0186 (9) | −0.0041 (9) |
C2 | 0.0345 (7) | 0.0233 (6) | 0.0307 (7) | −0.0010 (5) | 0.0010 (5) | 0.0017 (5) |
C3 | 0.0322 (7) | 0.0221 (6) | 0.0346 (7) | 0.0010 (5) | −0.0043 (5) | −0.0011 (5) |
C4 | 0.0353 (7) | 0.0230 (6) | 0.0327 (7) | −0.0024 (5) | 0.0021 (5) | 0.0024 (5) |
C5 | 0.0380 (7) | 0.0282 (6) | 0.0354 (7) | −0.0011 (5) | 0.0015 (6) | 0.0011 (6) |
C6 | 0.0565 (10) | 0.0445 (9) | 0.0340 (8) | −0.0041 (7) | 0.0040 (7) | −0.0047 (7) |
C7 | 0.0657 (11) | 0.0495 (10) | 0.0416 (9) | −0.0014 (8) | 0.0229 (8) | −0.0042 (7) |
C8 | 0.0473 (9) | 0.0380 (8) | 0.0506 (9) | −0.0019 (6) | 0.0218 (7) | 0.0074 (7) |
C9 | 0.0561 (11) | 0.0586 (11) | 0.0723 (13) | 0.0053 (9) | 0.0347 (10) | 0.0077 (10) |
C10 | 0.0438 (10) | 0.0768 (14) | 0.0970 (17) | 0.0131 (10) | 0.0274 (11) | 0.0125 (12) |
C11 | 0.0369 (9) | 0.0717 (13) | 0.0778 (14) | 0.0061 (9) | 0.0004 (9) | 0.0073 (11) |
C12 | 0.0374 (8) | 0.0438 (8) | 0.0517 (10) | 0.0017 (7) | 0.0029 (7) | 0.0056 (8) |
C13 | 0.0361 (7) | 0.0276 (7) | 0.0413 (8) | −0.0030 (5) | 0.0086 (6) | 0.0069 (6) |
C14 | 0.0377 (7) | 0.0273 (7) | 0.0364 (7) | 0.0055 (5) | 0.0017 (6) | −0.0002 (6) |
C15 | 0.1063 (17) | 0.0313 (8) | 0.0676 (12) | 0.0073 (9) | 0.0434 (12) | −0.0043 (8) |
C16 | 0.126 (2) | 0.0517 (11) | 0.0755 (14) | 0.0167 (12) | 0.0621 (15) | 0.0017 (10) |
C17 | 0.0658 (12) | 0.0556 (11) | 0.0645 (12) | 0.0081 (9) | 0.0303 (10) | 0.0132 (9) |
C18 | 0.0647 (11) | 0.0395 (9) | 0.0544 (10) | −0.0099 (8) | 0.0122 (8) | 0.0039 (8) |
C19 | 0.0589 (10) | 0.0317 (7) | 0.0400 (8) | −0.0053 (7) | 0.0088 (7) | −0.0037 (6) |
N1 | 0.0422 (7) | 0.0226 (6) | 0.0453 (7) | 0.0027 (5) | −0.0086 (5) | −0.0023 (5) |
N2 | 0.0365 (6) | 0.0229 (5) | 0.0409 (7) | 0.0019 (5) | −0.0092 (5) | −0.0018 (5) |
O1 | 0.0386 (5) | 0.0253 (5) | 0.0473 (6) | −0.0005 (4) | −0.0116 (5) | −0.0016 (4) |
O2 | 0.0351 (6) | 0.0416 (6) | 0.0449 (6) | 0.0018 (4) | −0.0087 (5) | −0.0109 (5) |
C1—N1 | 1.440 (2) | C9—H9 | 0.95 (2) |
C1—H1A | 0.96 (2) | C10—C11 | 1.401 (3) |
C1—H1B | 1.03 (3) | C10—H10 | 0.98 (2) |
C1—H1C | 1.01 (3) | C11—C12 | 1.370 (3) |
C2—O1 | 1.2523 (16) | C11—H11 | 0.97 (2) |
C2—N2 | 1.3428 (17) | C12—C13 | 1.423 (2) |
C2—N1 | 1.3447 (17) | C12—H12 | 0.971 (19) |
C3—N2 | 1.4693 (16) | C14—C19 | 1.378 (2) |
C3—C4 | 1.518 (2) | C14—C15 | 1.385 (2) |
C3—C14 | 1.529 (2) | C15—C16 | 1.380 (3) |
C3—H3 | 0.983 (16) | C15—H15 | 0.94 (3) |
C4—C5 | 1.3798 (19) | C16—C17 | 1.374 (3) |
C4—C13 | 1.432 (2) | C16—H16 | 0.99 (3) |
C5—O2 | 1.3698 (18) | C17—C18 | 1.366 (3) |
C5—C6 | 1.411 (2) | C17—H17 | 0.99 (2) |
C6—C7 | 1.358 (3) | C18—C19 | 1.384 (3) |
C6—H6 | 0.97 (2) | C18—H18 | 0.97 (2) |
C7—C8 | 1.413 (2) | C19—H19 | 0.97 (2) |
C7—H7 | 0.96 (2) | N1—H1D | 0.889 (19) |
C8—C9 | 1.419 (2) | N2—H2A | 0.859 (19) |
C8—C13 | 1.424 (2) | O2—H2B | 0.88 (2) |
C9—C10 | 1.352 (3) | ||
N1—C1—H1A | 109.1 (13) | C11—C10—H10 | 120.7 (14) |
N1—C1—H1B | 111.0 (15) | C12—C11—C10 | 121.03 (19) |
H1A—C1—H1B | 111 (2) | C12—C11—H11 | 117.7 (14) |
N1—C1—H1C | 109.7 (15) | C10—C11—H11 | 121.3 (14) |
H1A—C1—H1C | 109 (2) | C11—C12—C13 | 121.04 (19) |
H1B—C1—H1C | 107 (2) | C11—C12—H12 | 119.8 (11) |
O1—C2—N2 | 123.02 (12) | C13—C12—H12 | 119.1 (11) |
O1—C2—N1 | 119.67 (12) | C12—C13—C8 | 117.27 (14) |
N2—C2—N1 | 117.31 (12) | C12—C13—C4 | 123.15 (14) |
N2—C3—C4 | 111.65 (11) | C8—C13—C4 | 119.55 (13) |
N2—C3—C14 | 111.19 (12) | C19—C14—C15 | 117.65 (16) |
C4—C3—C14 | 114.34 (11) | C19—C14—C3 | 123.41 (14) |
N2—C3—H3 | 104.1 (9) | C15—C14—C3 | 118.88 (14) |
C4—C3—H3 | 108.5 (9) | C16—C15—C14 | 121.03 (18) |
C14—C3—H3 | 106.3 (9) | C16—C15—H15 | 120.9 (15) |
C5—C4—C13 | 118.61 (13) | C14—C15—H15 | 117.9 (15) |
C5—C4—C3 | 120.89 (12) | C17—C16—C15 | 120.4 (2) |
C13—C4—C3 | 120.47 (12) | C17—C16—H16 | 118.0 (17) |
O2—C5—C4 | 118.12 (13) | C15—C16—H16 | 121.5 (18) |
O2—C5—C6 | 120.40 (13) | C18—C17—C16 | 119.23 (19) |
C4—C5—C6 | 121.49 (14) | C18—C17—H17 | 120.2 (14) |
C7—C6—C5 | 120.19 (15) | C16—C17—H17 | 120.6 (14) |
C7—C6—H6 | 121.3 (12) | C17—C18—C19 | 120.38 (17) |
C5—C6—H6 | 118.5 (12) | C17—C18—H18 | 121.5 (13) |
C6—C7—C8 | 121.06 (16) | C19—C18—H18 | 118.1 (13) |
C6—C7—H7 | 118.9 (12) | C14—C19—C18 | 121.27 (16) |
C8—C7—H7 | 120.0 (12) | C14—C19—H19 | 118.4 (13) |
C7—C8—C9 | 121.38 (17) | C18—C19—H19 | 120.3 (13) |
C7—C8—C13 | 118.96 (15) | C2—N1—C1 | 125.63 (13) |
C9—C8—C13 | 119.65 (16) | C2—N1—H1D | 115.8 (11) |
C10—C9—C8 | 121.3 (2) | C1—N1—H1D | 118.6 (11) |
C10—C9—H9 | 123.4 (14) | C2—N2—C3 | 123.37 (11) |
C8—C9—H9 | 115.3 (14) | C2—N2—H2A | 119.6 (12) |
C9—C10—C11 | 119.74 (18) | C3—N2—H2A | 116.5 (12) |
C9—C10—H10 | 119.6 (14) | C5—O2—H2B | 110.5 (14) |
N2—C3—C4—C5 | 48.60 (17) | C9—C8—C13—C4 | 179.12 (14) |
C14—C3—C4—C5 | −78.72 (15) | C5—C4—C13—C12 | 174.57 (14) |
N2—C3—C4—C13 | −133.44 (13) | C3—C4—C13—C12 | −3.4 (2) |
C14—C3—C4—C13 | 99.24 (14) | C5—C4—C13—C8 | −3.42 (19) |
C13—C4—C5—O2 | −175.81 (12) | C3—C4—C13—C8 | 178.57 (12) |
C3—C4—C5—O2 | 2.19 (19) | N2—C3—C14—C19 | −125.95 (15) |
C13—C4—C5—C6 | 4.4 (2) | C4—C3—C14—C19 | 1.61 (19) |
C3—C4—C5—C6 | −177.63 (13) | N2—C3—C14—C15 | 56.72 (19) |
O2—C5—C6—C7 | 178.00 (15) | C4—C3—C14—C15 | −175.72 (15) |
C4—C5—C6—C7 | −2.2 (2) | C19—C14—C15—C16 | 1.6 (3) |
C5—C6—C7—C8 | −1.1 (3) | C3—C14—C15—C16 | 179.1 (2) |
C6—C7—C8—C9 | −176.84 (16) | C14—C15—C16—C17 | −0.4 (4) |
C6—C7—C8—C13 | 1.9 (2) | C15—C16—C17—C18 | −0.8 (4) |
C7—C8—C9—C10 | 178.11 (18) | C16—C17—C18—C19 | 0.6 (3) |
C13—C8—C9—C10 | −0.6 (3) | C15—C14—C19—C18 | −1.8 (3) |
C8—C9—C10—C11 | −0.3 (3) | C3—C14—C19—C18 | −179.18 (15) |
C9—C10—C11—C12 | 0.7 (3) | C17—C18—C19—C14 | 0.7 (3) |
C10—C11—C12—C13 | −0.3 (3) | O1—C2—N1—C1 | −178.43 (18) |
C11—C12—C13—C8 | −0.6 (2) | N2—C2—N1—C1 | 1.1 (3) |
C11—C12—C13—C4 | −178.58 (16) | O1—C2—N2—C3 | −4.2 (2) |
C7—C8—C13—C12 | −177.75 (15) | N1—C2—N2—C3 | 176.25 (14) |
C9—C8—C13—C12 | 1.0 (2) | C4—C3—N2—C2 | 130.41 (14) |
C7—C8—C13—C4 | 0.3 (2) | C14—C3—N2—C2 | −100.59 (16) |