Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012275/si2004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012275/si2004Isup2.hkl |
CCDC reference: 643094
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.193
- Data-to-parameter ratio = 20.8
checkCIF/PLATON results
No syntax errors found
Alert level A DIFF019_ALERT_1_A _diffrn_standards_number is missing Number of standards used in measurement. DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.857 0.984 Tmin(prime) and Tmax expected: 0.976 0.984 RR(prime) = 0.878 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C8 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C13 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P1 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... \P2
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993\bbr00q) in WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C19H22N2O2 | F(000) = 664 |
Mr = 310.39 | Dx = 1.224 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7073 reflections |
a = 12.4524 (4) Å | θ = 2.1–28° |
b = 15.3347 (5) Å | µ = 0.08 mm−1 |
c = 8.8832 (2) Å | T = 293 K |
β = 96.991 (2)° | Plate, colourless |
V = 1683.67 (9) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Bruker Kappa-APEX2 diffractometer | 4335 independent reflections |
Radiation source: fine-focus sealed tube | 2848 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω and φ scans | θmax = 28.7°, θmin = 1.7° |
Absorption correction: multi-scan (Blessing, 1995) | h = −16→16 |
Tmin = 0.857, Tmax = 0.984 | k = −20→20 |
20405 measured reflections | l = −11→11 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.193 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1092P)2 + 0.2308P] where P = (Fo2 + 2Fc2)/3 |
4335 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | ||
C1 | 0.08793 (16) | 0.85107 (12) | 1.1554 (2) | 0.0605 (4) | |
C2 | 0.0515 (2) | 0.83451 (15) | 1.2956 (2) | 0.0795 (6) | |
H2 | 0.1000 | 0.8150 | 1.3765 | 0.095* | |
C3 | −0.0559 (2) | 0.84689 (15) | 1.3148 (2) | 0.0818 (7) | |
H3 | −0.0790 | 0.8359 | 1.4087 | 0.098* | |
C4 | −0.12882 (18) | 0.87509 (14) | 1.1971 (2) | 0.0726 (6) | |
H4 | −0.2008 | 0.8840 | 1.2113 | 0.087* | |
C5 | −0.09523 (15) | 0.89015 (12) | 1.0578 (2) | 0.0612 (5) | |
H5 | −0.1455 | 0.9089 | 0.9783 | 0.073* | |
C6 | 0.01260 (13) | 0.87813 (10) | 1.03197 (18) | 0.0497 (4) | |
C7 | 0.04743 (13) | 0.89107 (10) | 0.88117 (18) | 0.0485 (4) | |
C8 | −0.03427 (15) | 0.91290 (15) | 0.7489 (2) | 0.0659 (5) | |
H8A | 0.0014 | 0.9193 | 0.6596 | 0.099* | |
H8B | −0.0698 | 0.9665 | 0.7685 | 0.099* | |
H8C | −0.0868 | 0.8669 | 0.7336 | 0.099* | |
C9 | 0.19118 (14) | 0.88534 (13) | 0.7236 (2) | 0.0592 (4) | |
H9A | 0.1767 | 0.9425 | 0.6790 | 0.071* | |
H9B | 0.1558 | 0.8422 | 0.6548 | 0.071* | |
C10 | 0.31163 (14) | 0.86895 (13) | 0.7459 (2) | 0.0619 (5) | |
H10A | 0.3471 | 0.9175 | 0.8016 | 0.074* | |
H10B | 0.3260 | 0.8169 | 0.8071 | 0.074* | |
C11 | 0.35990 (15) | 0.85764 (12) | 0.5993 (2) | 0.0627 (5) | |
H11A | 0.4358 | 0.8424 | 0.6214 | 0.075* | |
H11B | 0.3233 | 0.8104 | 0.5412 | 0.075* | |
C12 | 0.38548 (12) | 0.94528 (10) | 0.38155 (18) | 0.0489 (4) | |
C13 | 0.44276 (15) | 0.87288 (13) | 0.3096 (2) | 0.0670 (5) | |
H13A | 0.4458 | 0.8222 | 0.3735 | 0.101* | |
H13B | 0.5149 | 0.8911 | 0.2971 | 0.101* | |
H13C | 0.4041 | 0.8591 | 0.2124 | 0.101* | |
C14 | 0.37098 (11) | 1.03009 (10) | 0.30374 (17) | 0.0473 (4) | |
C15 | 0.40440 (14) | 1.04511 (13) | 0.1617 (2) | 0.0634 (5) | |
H15 | 0.4353 | 0.9996 | 0.1127 | 0.076* | |
C16 | 0.39290 (16) | 1.12563 (16) | 0.0914 (2) | 0.0726 (6) | |
H16 | 0.4167 | 1.1341 | −0.0027 | 0.087* | |
C17 | 0.34599 (15) | 1.19306 (14) | 0.1621 (2) | 0.0667 (5) | |
H17 | 0.3382 | 1.2474 | 0.1154 | 0.080* | |
C18 | 0.31083 (14) | 1.18080 (11) | 0.3001 (2) | 0.0578 (4) | |
H18 | 0.2789 | 1.2269 | 0.3461 | 0.069* | |
C19 | 0.32189 (12) | 1.10045 (10) | 0.37325 (17) | 0.0474 (4) | |
N1 | 0.14839 (11) | 0.88058 (9) | 0.86902 (16) | 0.0534 (3) | |
N2 | 0.34936 (11) | 0.93775 (9) | 0.51000 (16) | 0.0525 (3) | |
O1 | 0.19250 (11) | 0.83961 (11) | 1.14088 (16) | 0.0791 (4) | |
H1 | 0.2032 | 0.8515 | 1.0539 | 0.119* | |
O2 | 0.28584 (11) | 1.09222 (8) | 0.50796 (13) | 0.0617 (3) | |
H2A | 0.2646 | 1.0422 | 0.5179 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0714 (12) | 0.0527 (9) | 0.0571 (10) | −0.0003 (8) | 0.0070 (8) | 0.0004 (8) |
C2 | 0.1118 (19) | 0.0734 (13) | 0.0532 (10) | 0.0004 (12) | 0.0095 (10) | 0.0059 (9) |
C3 | 0.1148 (19) | 0.0740 (13) | 0.0629 (12) | −0.0154 (12) | 0.0366 (12) | −0.0073 (10) |
C4 | 0.0762 (13) | 0.0724 (13) | 0.0742 (13) | −0.0181 (10) | 0.0296 (10) | −0.0161 (10) |
C5 | 0.0591 (10) | 0.0628 (11) | 0.0636 (10) | −0.0124 (8) | 0.0144 (8) | −0.0103 (8) |
C6 | 0.0518 (9) | 0.0446 (8) | 0.0530 (9) | −0.0085 (6) | 0.0080 (6) | −0.0047 (6) |
C7 | 0.0486 (9) | 0.0458 (8) | 0.0511 (8) | −0.0065 (6) | 0.0056 (6) | −0.0015 (6) |
C8 | 0.0536 (10) | 0.0860 (14) | 0.0573 (10) | −0.0021 (9) | 0.0029 (7) | 0.0004 (9) |
C9 | 0.0520 (10) | 0.0679 (11) | 0.0592 (10) | −0.0012 (8) | 0.0128 (7) | 0.0073 (8) |
C10 | 0.0521 (10) | 0.0642 (11) | 0.0712 (11) | 0.0031 (8) | 0.0143 (8) | 0.0190 (8) |
C11 | 0.0552 (10) | 0.0523 (9) | 0.0840 (12) | 0.0074 (8) | 0.0223 (8) | 0.0129 (9) |
C12 | 0.0355 (7) | 0.0509 (9) | 0.0613 (9) | −0.0018 (6) | 0.0106 (6) | −0.0060 (7) |
C13 | 0.0607 (11) | 0.0606 (11) | 0.0839 (13) | 0.0060 (8) | 0.0255 (9) | −0.0096 (9) |
C14 | 0.0376 (7) | 0.0544 (9) | 0.0508 (8) | −0.0029 (6) | 0.0089 (6) | −0.0018 (7) |
C15 | 0.0571 (10) | 0.0784 (12) | 0.0577 (10) | 0.0025 (9) | 0.0197 (8) | −0.0008 (9) |
C16 | 0.0691 (12) | 0.0958 (16) | 0.0550 (10) | −0.0065 (11) | 0.0158 (8) | 0.0152 (10) |
C17 | 0.0648 (11) | 0.0698 (12) | 0.0627 (10) | −0.0108 (9) | −0.0035 (8) | 0.0180 (9) |
C18 | 0.0617 (10) | 0.0510 (9) | 0.0587 (9) | −0.0004 (8) | −0.0007 (7) | 0.0009 (7) |
C19 | 0.0443 (8) | 0.0499 (9) | 0.0479 (8) | −0.0029 (6) | 0.0053 (6) | −0.0016 (6) |
N1 | 0.0490 (8) | 0.0559 (8) | 0.0558 (8) | −0.0024 (6) | 0.0088 (6) | 0.0040 (6) |
N2 | 0.0480 (7) | 0.0483 (7) | 0.0635 (8) | 0.0012 (6) | 0.0165 (6) | 0.0053 (6) |
O1 | 0.0682 (9) | 0.0974 (11) | 0.0696 (9) | 0.0154 (7) | −0.0005 (6) | 0.0132 (7) |
O2 | 0.0784 (9) | 0.0535 (7) | 0.0577 (7) | 0.0064 (6) | 0.0259 (6) | −0.0008 (5) |
C1—O1 | 1.336 (2) | C10—H10B | 0.9700 |
C1—C2 | 1.400 (3) | C11—N2 | 1.460 (2) |
C1—C6 | 1.415 (2) | C11—H11A | 0.9700 |
C2—C3 | 1.382 (3) | C11—H11B | 0.9700 |
C2—H2 | 0.9300 | C12—N2 | 1.2817 (19) |
C3—C4 | 1.369 (3) | C12—C14 | 1.473 (2) |
C3—H3 | 0.9300 | C12—C13 | 1.504 (2) |
C4—C5 | 1.373 (3) | C13—H13A | 0.9600 |
C4—H4 | 0.9300 | C13—H13B | 0.9600 |
C5—C6 | 1.402 (2) | C13—H13C | 0.9600 |
C5—H5 | 0.9300 | C14—C15 | 1.395 (2) |
C6—C7 | 1.471 (2) | C14—C19 | 1.418 (2) |
C7—N1 | 1.285 (2) | C15—C16 | 1.383 (3) |
C7—C8 | 1.496 (2) | C15—H15 | 0.9300 |
C8—H8A | 0.9600 | C16—C17 | 1.376 (3) |
C8—H8B | 0.9600 | C16—H16 | 0.9300 |
C8—H8C | 0.9600 | C17—C18 | 1.364 (3) |
C9—N1 | 1.458 (2) | C17—H17 | 0.9300 |
C9—C10 | 1.510 (2) | C18—C19 | 1.392 (2) |
C9—H9A | 0.9700 | C18—H18 | 0.9300 |
C9—H9B | 0.9700 | C19—O2 | 1.3343 (18) |
C10—C11 | 1.509 (3) | O1—H1 | 0.8200 |
C10—H10A | 0.9700 | O2—H2A | 0.8200 |
O1—C1—C2 | 119.14 (18) | H10A—C10—H10B | 107.7 |
O1—C1—C6 | 121.74 (16) | N2—C11—C10 | 110.69 (14) |
C2—C1—C6 | 119.12 (19) | N2—C11—H11A | 109.5 |
C3—C2—C1 | 120.5 (2) | C10—C11—H11A | 109.5 |
C3—C2—H2 | 119.7 | N2—C11—H11B | 109.5 |
C1—C2—H2 | 119.7 | C10—C11—H11B | 109.5 |
C4—C3—C2 | 120.74 (19) | H11A—C11—H11B | 108.1 |
C4—C3—H3 | 119.6 | N2—C12—C14 | 117.45 (13) |
C2—C3—H3 | 119.6 | N2—C12—C13 | 123.21 (16) |
C3—C4—C5 | 119.7 (2) | C14—C12—C13 | 119.33 (14) |
C3—C4—H4 | 120.2 | C12—C13—H13A | 109.5 |
C5—C4—H4 | 120.2 | C12—C13—H13B | 109.5 |
C4—C5—C6 | 121.90 (19) | H13A—C13—H13B | 109.5 |
C4—C5—H5 | 119.1 | C12—C13—H13C | 109.5 |
C6—C5—H5 | 119.1 | H13A—C13—H13C | 109.5 |
C5—C6—C1 | 118.01 (16) | H13B—C13—H13C | 109.5 |
C5—C6—C7 | 121.73 (15) | C15—C14—C19 | 117.39 (15) |
C1—C6—C7 | 120.25 (15) | C15—C14—C12 | 122.48 (14) |
N1—C7—C6 | 117.36 (14) | C19—C14—C12 | 120.14 (13) |
N1—C7—C8 | 122.74 (15) | C16—C15—C14 | 121.97 (17) |
C6—C7—C8 | 119.87 (15) | C16—C15—H15 | 119.0 |
C7—C8—H8A | 109.5 | C14—C15—H15 | 119.0 |
C7—C8—H8B | 109.5 | C17—C16—C15 | 119.45 (17) |
H8A—C8—H8B | 109.5 | C17—C16—H16 | 120.3 |
C7—C8—H8C | 109.5 | C15—C16—H16 | 120.3 |
H8A—C8—H8C | 109.5 | C18—C17—C16 | 120.45 (18) |
H8B—C8—H8C | 109.5 | C18—C17—H17 | 119.8 |
N1—C9—C10 | 109.86 (15) | C16—C17—H17 | 119.8 |
N1—C9—H9A | 109.7 | C17—C18—C19 | 121.15 (17) |
C10—C9—H9A | 109.7 | C17—C18—H18 | 119.4 |
N1—C9—H9B | 109.7 | C19—C18—H18 | 119.4 |
C10—C9—H9B | 109.7 | O2—C19—C18 | 118.52 (14) |
H9A—C9—H9B | 108.2 | O2—C19—C14 | 121.90 (14) |
C11—C10—C9 | 113.56 (16) | C18—C19—C14 | 119.58 (15) |
C11—C10—H10A | 108.9 | C7—N1—C9 | 122.34 (14) |
C9—C10—H10A | 108.9 | C12—N2—C11 | 122.80 (14) |
C11—C10—H10B | 108.9 | C1—O1—H1 | 109.5 |
C9—C10—H10B | 108.9 | C19—O2—H2A | 109.5 |
O1—C1—C2—C3 | 179.1 (2) | N2—C12—C14—C19 | 2.0 (2) |
C6—C1—C2—C3 | −1.9 (3) | C13—C12—C14—C19 | −176.92 (15) |
C1—C2—C3—C4 | 0.3 (3) | C19—C14—C15—C16 | 1.4 (3) |
C2—C3—C4—C5 | 0.9 (3) | C12—C14—C15—C16 | −178.30 (17) |
C3—C4—C5—C6 | −0.5 (3) | C14—C15—C16—C17 | −0.8 (3) |
C4—C5—C6—C1 | −1.1 (3) | C15—C16—C17—C18 | −0.1 (3) |
C4—C5—C6—C7 | 177.60 (16) | C16—C17—C18—C19 | 0.4 (3) |
O1—C1—C6—C5 | −178.82 (17) | C17—C18—C19—O2 | −179.88 (15) |
C2—C1—C6—C5 | 2.2 (3) | C17—C18—C19—C14 | 0.3 (2) |
O1—C1—C6—C7 | 2.5 (3) | C15—C14—C19—O2 | 179.02 (15) |
C2—C1—C6—C7 | −176.45 (16) | C12—C14—C19—O2 | −1.2 (2) |
C5—C6—C7—N1 | 178.38 (15) | C15—C14—C19—C18 | −1.2 (2) |
C1—C6—C7—N1 | −3.0 (2) | C12—C14—C19—C18 | 178.58 (14) |
C5—C6—C7—C8 | −3.4 (2) | C6—C7—N1—C9 | 175.41 (14) |
C1—C6—C7—C8 | 175.25 (16) | C8—C7—N1—C9 | −2.8 (3) |
N1—C9—C10—C11 | 170.33 (15) | C10—C9—N1—C7 | −179.11 (16) |
C9—C10—C11—N2 | 64.1 (2) | C14—C12—N2—C11 | −179.17 (15) |
N2—C12—C14—C15 | −178.23 (15) | C13—C12—N2—C11 | −0.3 (3) |
C13—C12—C14—C15 | 2.8 (2) | C10—C11—N2—C12 | 178.99 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.76 | 2.4912 (19) | 148 |
O2—H2A···N2 | 0.82 | 1.92 | 2.4967 (17) | 126 |
C8—H8B···Π1i | 0.96 | 2.88 | 3.558 | 129 |
C11—H11A···Π2ii | 0.97 | 2.82 | 3.678 | 148 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x, −y+2, −z+1. |
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