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
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.112
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.23 Ratio PLAT410_ALERT_2_C Short Intra H...H Contact H3 .. H12 .. 1.97 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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) |
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