Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008480/ya6027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008480/ya6027Isup2.hkl |
CCDC reference: 170318
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.095
- Data-to-parameter ratio = 9.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
ABSMU_01 Alert B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.074 Value of mu given = 0.070
Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(15) - C(16) = 1.43 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(15) - C(17) = 1.43 Ang. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.40 From the CIF: _reflns_number_total 1921 Count of symmetry unique reflns 1962 Completeness (_total/calc) 97.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995).
C19H18N2O | Dx = 1.187 Mg m−3 |
Mr = 290.35 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 10060 reflections |
a = 15.4413 (3) Å | θ = 3.1–27.4° |
b = 10.9988 (3) Å | µ = 0.07 mm−1 |
c = 9.5699 (2) Å | T = 291 K |
V = 1625.31 (6) Å3 | Block, red |
Z = 4 | 0.25 × 0.23 × 0.23 mm |
F(000) = 616 |
Nonius KappaCCD diffractometer | 1302 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.4°, θmin = 3.1° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −19→19 |
201 frames via ω–rotation (Δω=1%) and two times 20 s per frame (two sets at different κ–angles) scans | k = −14→14 |
1921 measured reflections | l = −12→12 |
1921 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0555P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
1921 reflections | Δρmax = 0.12 e Å−3 |
203 parameters | Δρmin = −0.11 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (3) |
Experimental. The data collection covered the whole sphere of reciprocal space. The crystal-to-detector distance was 34 mm. Crystal decay was monitored by repeating the initial frames at the end of data collection and analysing the duplicate reflections. |
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 | ||
O1 | 0.54750 (10) | 0.15514 (18) | 0.5395 (2) | 0.0749 (6) | |
H1 | 0.5783 | 0.1870 | 0.5989 | 0.112* | |
N1 | 0.83970 (17) | −0.2503 (2) | −0.7355 (3) | 0.0753 (7) | |
N2 | 0.58520 (17) | −0.2233 (2) | −0.5335 (3) | 0.0827 (7) | |
C1 | 0.69221 (13) | 0.04293 (19) | 0.1955 (2) | 0.0426 (5) | |
C2 | 0.73123 (13) | 0.09715 (19) | 0.3099 (2) | 0.0468 (6) | |
H2 | 0.7909 | 0.1082 | 0.3089 | 0.056* | |
C3 | 0.68509 (14) | 0.1355 (2) | 0.4254 (2) | 0.0478 (5) | |
H3 | 0.7134 | 0.1725 | 0.4999 | 0.057* | |
C4 | 0.59748 (13) | 0.1186 (2) | 0.4293 (2) | 0.0509 (6) | |
C5 | 0.55606 (15) | 0.0642 (3) | 0.3172 (3) | 0.0652 (7) | |
H5 | 0.4964 | 0.0528 | 0.3198 | 0.078* | |
C6 | 0.60214 (14) | 0.0271 (2) | 0.2025 (3) | 0.0592 (7) | |
H6 | 0.5733 | −0.0092 | 0.1282 | 0.071* | |
C7 | 0.74379 (14) | 0.00947 (19) | 0.0751 (2) | 0.0444 (5) | |
H7 | 0.8034 | 0.0162 | 0.0862 | 0.053* | |
C8 | 0.71726 (14) | −0.0297 (2) | −0.0493 (2) | 0.0465 (6) | |
H8 | 0.6579 | −0.0391 | −0.0617 | 0.056* | |
C9 | 0.77203 (13) | −0.05884 (18) | −0.1669 (2) | 0.0416 (5) | |
C10 | 0.73713 (13) | −0.10251 (19) | −0.2865 (2) | 0.0454 (5) | |
H10 | 0.6772 | −0.1086 | −0.2922 | 0.054* | |
C11 | 0.78721 (13) | −0.13980 (19) | −0.4043 (2) | 0.0428 (5) | |
C12 | 0.88379 (13) | −0.1336 (2) | −0.3922 (3) | 0.0552 (6) | |
H12A | 0.9082 | −0.1208 | −0.4845 | 0.066* | |
H12B | 0.9051 | −0.2110 | −0.3579 | 0.066* | |
C13 | 0.91548 (13) | −0.0324 (2) | −0.2950 (2) | 0.0504 (6) | |
C14 | 0.86870 (13) | −0.0443 (2) | −0.1551 (2) | 0.0453 (5) | |
H14A | 0.8920 | −0.1141 | −0.1057 | 0.054* | |
H14B | 0.8809 | 0.0273 | −0.0994 | 0.054* | |
C15 | 0.74921 (14) | −0.18608 (19) | −0.5220 (2) | 0.0479 (6) | |
C16 | 0.79921 (16) | −0.2226 (2) | −0.6404 (3) | 0.0542 (6) | |
C17 | 0.65798 (18) | −0.2053 (2) | −0.5306 (3) | 0.0544 (6) | |
C18 | 1.01269 (15) | −0.0488 (3) | −0.2716 (3) | 0.0791 (9) | |
H18A | 1.0423 | −0.0448 | −0.3597 | 0.119* | |
H18B | 1.0232 | −0.1263 | −0.2289 | 0.119* | |
H18C | 1.0336 | 0.0146 | −0.2115 | 0.119* | |
C19 | 0.89807 (17) | 0.0923 (2) | −0.3597 (3) | 0.0710 (7) | |
H19A | 0.8367 | 0.1044 | −0.3685 | 0.107* | |
H19B | 0.9245 | 0.0964 | −0.4504 | 0.107* | |
H19C | 0.9221 | 0.1545 | −0.3008 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0675 (10) | 0.1041 (14) | 0.0531 (11) | −0.0104 (10) | 0.0201 (9) | −0.0254 (10) |
N1 | 0.0944 (17) | 0.0894 (15) | 0.0420 (13) | −0.0080 (12) | 0.0055 (13) | −0.0218 (12) |
N2 | 0.0766 (16) | 0.0971 (18) | 0.0743 (17) | −0.0156 (13) | −0.0113 (15) | −0.0127 (14) |
C1 | 0.0457 (12) | 0.0476 (12) | 0.0343 (13) | −0.0012 (9) | 0.0037 (10) | −0.0037 (10) |
C2 | 0.0425 (11) | 0.0571 (13) | 0.0407 (14) | 0.0006 (10) | −0.0011 (11) | −0.0034 (11) |
C3 | 0.0547 (13) | 0.0551 (13) | 0.0337 (12) | 0.0009 (10) | −0.0031 (11) | −0.0097 (11) |
C4 | 0.0536 (15) | 0.0588 (14) | 0.0402 (14) | −0.0019 (10) | 0.0149 (12) | −0.0075 (11) |
C5 | 0.0458 (13) | 0.0960 (19) | 0.0539 (17) | −0.0160 (12) | 0.0098 (14) | −0.0177 (15) |
C6 | 0.0514 (13) | 0.0843 (17) | 0.0419 (15) | −0.0173 (11) | 0.0042 (12) | −0.0168 (14) |
C7 | 0.0444 (11) | 0.0528 (13) | 0.0361 (13) | −0.0003 (9) | 0.0016 (10) | −0.0007 (10) |
C8 | 0.0449 (11) | 0.0583 (14) | 0.0364 (14) | −0.0036 (10) | 0.0034 (11) | −0.0079 (10) |
C9 | 0.0466 (11) | 0.0451 (11) | 0.0330 (12) | 0.0015 (9) | 0.0014 (11) | −0.0031 (10) |
C10 | 0.0464 (11) | 0.0528 (13) | 0.0369 (12) | −0.0026 (9) | −0.0021 (11) | −0.0064 (11) |
C11 | 0.0542 (12) | 0.0414 (11) | 0.0327 (12) | −0.0024 (9) | 0.0015 (11) | −0.0023 (10) |
C12 | 0.0542 (12) | 0.0713 (16) | 0.0400 (14) | 0.0005 (11) | 0.0060 (11) | −0.0138 (12) |
C13 | 0.0467 (12) | 0.0679 (15) | 0.0367 (13) | −0.0072 (10) | 0.0045 (11) | −0.0110 (12) |
C14 | 0.0475 (12) | 0.0532 (13) | 0.0352 (13) | −0.0001 (9) | 0.0007 (10) | −0.0055 (11) |
C15 | 0.0625 (14) | 0.0471 (13) | 0.0341 (13) | −0.0061 (10) | −0.0010 (12) | −0.0055 (11) |
C16 | 0.0719 (16) | 0.0554 (14) | 0.0354 (14) | −0.0072 (11) | −0.0041 (13) | −0.0092 (12) |
C17 | 0.0690 (18) | 0.0550 (14) | 0.0392 (14) | −0.0085 (11) | −0.0074 (13) | −0.0059 (11) |
C18 | 0.0472 (13) | 0.135 (3) | 0.0550 (18) | −0.0085 (15) | 0.0070 (14) | −0.0223 (18) |
C19 | 0.0890 (17) | 0.0771 (17) | 0.0470 (16) | −0.0217 (13) | 0.0105 (14) | 0.0007 (15) |
O1—C4 | 1.368 (3) | C10—C11 | 1.427 (3) |
O1—H1 | 0.820 | C10—H10 | 0.930 |
N1—C16 | 1.145 (3) | C11—C15 | 1.368 (3) |
N2—C17 | 1.141 (3) | C11—C12 | 1.497 (3) |
C1—C2 | 1.385 (3) | C12—C13 | 1.531 (3) |
C1—C6 | 1.403 (3) | C12—H12A | 0.970 |
C1—C7 | 1.448 (3) | C12—H12B | 0.970 |
C2—C3 | 1.381 (3) | C13—C14 | 1.527 (3) |
C2—H2 | 0.930 | C13—C18 | 1.528 (3) |
C3—C4 | 1.366 (3) | C13—C19 | 1.529 (4) |
C3—H3 | 0.930 | C14—H14A | 0.970 |
C4—C5 | 1.385 (3) | C14—H14B | 0.970 |
C5—C6 | 1.370 (3) | C15—C17 | 1.427 (4) |
C5—H5 | 0.930 | C15—C16 | 1.429 (4) |
C6—H6 | 0.930 | C18—H18A | 0.960 |
C7—C8 | 1.330 (3) | C18—H18B | 0.960 |
C7—H7 | 0.930 | C18—H18C | 0.960 |
C8—C9 | 1.444 (3) | C19—H19A | 0.960 |
C8—H8 | 0.930 | C19—H19B | 0.960 |
C9—C10 | 1.353 (3) | C19—H19C | 0.960 |
C9—C14 | 1.505 (3) | ||
C4—O1—H1 | 109.5 | C11—C12—H12A | 108.9 |
C2—C1—C6 | 116.51 (19) | C13—C12—H12A | 108.9 |
C2—C1—C7 | 119.96 (17) | C11—C12—H12B | 108.9 |
C6—C1—C7 | 123.50 (19) | C13—C12—H12B | 108.9 |
C3—C2—C1 | 122.69 (18) | H12A—C12—H12B | 107.7 |
C3—C2—H2 | 118.7 | C14—C13—C18 | 109.04 (19) |
C1—C2—H2 | 118.7 | C14—C13—C19 | 110.42 (19) |
C4—C3—C2 | 119.4 (2) | C18—C13—C19 | 109.7 (2) |
C4—C3—H3 | 120.3 | C14—C13—C12 | 108.62 (18) |
C2—C3—H3 | 120.3 | C18—C13—C12 | 108.51 (18) |
C3—C4—O1 | 122.7 (2) | C19—C13—C12 | 110.5 (2) |
C3—C4—C5 | 119.7 (2) | C9—C14—C13 | 114.35 (19) |
O1—C4—C5 | 117.64 (18) | C9—C14—H14A | 108.7 |
C6—C5—C4 | 120.6 (2) | C13—C14—H14A | 108.7 |
C6—C5—H5 | 119.7 | C9—C14—H14B | 108.7 |
C4—C5—H5 | 119.7 | C13—C14—H14B | 108.7 |
C5—C6—C1 | 121.1 (2) | H14A—C14—H14B | 107.6 |
C5—C6—H6 | 119.5 | C11—C15—C17 | 121.8 (2) |
C1—C6—H6 | 119.5 | C11—C15—C16 | 121.73 (19) |
C8—C7—C1 | 128.66 (18) | C17—C15—C16 | 116.4 (2) |
C8—C7—H7 | 115.7 | N1—C16—C15 | 179.0 (3) |
C1—C7—H7 | 115.7 | N2—C17—C15 | 177.6 (3) |
C7—C8—C9 | 126.08 (19) | C13—C18—H18A | 109.5 |
C7—C8—H8 | 117.0 | C13—C18—H18B | 109.5 |
C9—C8—H8 | 117.0 | H18A—C18—H18B | 109.5 |
C10—C9—C8 | 120.31 (17) | C13—C18—H18C | 109.5 |
C10—C9—C14 | 119.74 (19) | H18A—C18—H18C | 109.5 |
C8—C9—C14 | 119.91 (19) | H18B—C18—H18C | 109.5 |
C9—C10—C11 | 123.66 (18) | C13—C19—H19A | 109.5 |
C9—C10—H10 | 118.2 | C13—C19—H19B | 109.5 |
C11—C10—H10 | 118.2 | H19A—C19—H19B | 109.5 |
C15—C11—C10 | 121.65 (17) | C13—C19—H19C | 109.5 |
C15—C11—C12 | 120.49 (19) | H19A—C19—H19C | 109.5 |
C10—C11—C12 | 117.76 (18) | H19B—C19—H19C | 109.5 |
C11—C12—C13 | 113.46 (18) | ||
C6—C1—C2—C3 | −0.7 (3) | C9—C10—C11—C15 | 178.5 (2) |
C7—C1—C2—C3 | 177.37 (19) | C9—C10—C11—C12 | 2.0 (3) |
C1—C2—C3—C4 | 0.8 (3) | C15—C11—C12—C13 | 153.2 (2) |
C2—C3—C4—O1 | −179.4 (2) | C10—C11—C12—C13 | −30.2 (3) |
C2—C3—C4—C5 | −0.5 (3) | C11—C12—C13—C14 | 52.0 (3) |
C3—C4—C5—C6 | 0.1 (4) | C11—C12—C13—C18 | 170.4 (2) |
O1—C4—C5—C6 | 179.0 (2) | C11—C12—C13—C19 | −69.2 (3) |
C4—C5—C6—C1 | 0.0 (4) | C10—C9—C14—C13 | 23.2 (3) |
C2—C1—C6—C5 | 0.2 (3) | C8—C9—C14—C13 | −158.7 (2) |
C7—C1—C6—C5 | −177.7 (2) | C18—C13—C14—C9 | −166.7 (2) |
C2—C1—C7—C8 | −171.4 (2) | C19—C13—C14—C9 | 72.7 (2) |
C6—C1—C7—C8 | 6.5 (4) | C12—C13—C14—C9 | −48.6 (3) |
C1—C7—C8—C9 | 178.3 (2) | C10—C11—C15—C17 | −3.2 (3) |
C7—C8—C9—C10 | 177.4 (2) | C12—C11—C15—C17 | 173.1 (2) |
C7—C8—C9—C14 | −0.7 (3) | C10—C11—C15—C16 | 179.5 (2) |
C8—C9—C10—C11 | −176.37 (19) | C12—C11—C15—C16 | −4.1 (3) |
C14—C9—C10—C11 | 1.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.14 | 2.958 (3) | 173 |
Symmetry code: (i) −x+3/2, y+1/2, z+3/2. |
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