Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026497/lh6137sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026497/lh6137Isup2.hkl |
CCDC reference: 232131
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.067
- Data-to-parameter ratio = 7.1
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.122 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.10 PLAT128_ALERT_4_C Non-standard setting of Space group Pna21 .... P21nb PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C15 = 5.74 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C3 PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. CG3 = 2.85 Ang.
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1611 Count of symmetry unique reflns 1611 Completeness (_total/calc) 100.00% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H19NO3 | F(000) = 704 |
Mr = 333.37 | Dx = 1.291 Mg m−3 |
Orthorhombic, P21nb | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2bc 2a | Cell parameters from 11804 reflections |
a = 9.1755 (9) Å | θ = 2.1–29.6° |
b = 9.4488 (7) Å | µ = 0.09 mm−1 |
c = 19.7807 (18) Å | T = 293 K |
V = 1714.9 (3) Å3 | Plate, colourless |
Z = 4 | 0.80 × 0.38 × 0.06 mm |
STOE IPDS 2 diffractometer | 1611 independent reflections |
Radiation source: sealed X-ray tube | 1229 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.122 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
rotation method scans | h = −10→10 |
Absorption correction: integration STOE X-RED (Stoe & Cie, 2002) | k = −10→11 |
Tmin = 0.952, Tmax = 0.993 | l = −23→23 |
21176 measured 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)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.0291P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.036 |
1611 reflections | Δρmax = 0.11 e Å−3 |
227 parameters | Δρmin = −0.12 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: 0.031 (2) |
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 | −0.0822 (2) | 0.8443 (2) | 0.27477 (10) | 0.0789 (6) | |
O2 | 0.13871 (19) | 0.4419 (2) | 0.34655 (9) | 0.0648 (5) | |
O3 | 0.3239 (2) | 0.7473 (2) | 0.30420 (10) | 0.0836 (7) | |
N1 | 0.0457 (2) | 0.6397 (2) | 0.29553 (10) | 0.0545 (5) | |
C1 | 0.4087 (3) | 0.6206 (3) | 0.20751 (13) | 0.0586 (7) | |
H1 | 0.4033 | 0.5172 | 0.2043 | 0.070* | |
C2 | 0.4050 (3) | 0.6890 (3) | 0.13614 (12) | 0.0592 (7) | |
H2A | 0.3951 | 0.6208 | 0.0997 | 0.071* | |
H2B | 0.3335 | 0.7641 | 0.1318 | 0.071* | |
C3 | 0.5629 (3) | 0.7434 (3) | 0.14602 (11) | 0.0533 (6) | |
C4 | 0.5671 (3) | 0.6693 (4) | 0.21632 (13) | 0.0747 (9) | |
H4A | 0.6363 | 0.5919 | 0.2188 | 0.090* | |
H4B | 0.5808 | 0.7343 | 0.2537 | 0.090* | |
C5 | 0.0524 (3) | 0.5382 (3) | 0.34549 (12) | 0.0498 (6) | |
C6 | −0.0602 (2) | 0.5761 (3) | 0.39567 (11) | 0.0475 (6) | |
C7 | −0.1009 (3) | 0.5098 (3) | 0.45435 (11) | 0.0565 (6) | |
H7 | −0.0577 | 0.4256 | 0.4681 | 0.068* | |
C8 | −0.2094 (3) | 0.5739 (3) | 0.49215 (13) | 0.0654 (7) | |
H8 | −0.2397 | 0.5321 | 0.5323 | 0.078* | |
C9 | −0.2728 (3) | 0.6976 (3) | 0.47151 (15) | 0.0701 (8) | |
H9 | −0.3449 | 0.7382 | 0.4983 | 0.084* | |
C10 | −0.2330 (3) | 0.7637 (3) | 0.41214 (16) | 0.0677 (8) | |
H10 | −0.2769 | 0.8475 | 0.3981 | 0.081* | |
C11 | −0.1249 (3) | 0.6994 (3) | 0.37452 (12) | 0.0519 (6) | |
C12 | −0.0573 (3) | 0.7428 (3) | 0.30956 (13) | 0.0551 (6) | |
C13 | 0.1425 (3) | 0.6381 (3) | 0.23795 (12) | 0.0604 (7) | |
H13A | 0.1067 | 0.7046 | 0.2045 | 0.073* | |
H13B | 0.1409 | 0.5445 | 0.2178 | 0.073* | |
C14 | 0.2975 (3) | 0.6758 (3) | 0.25558 (12) | 0.0571 (7) | |
C15 | 0.5694 (4) | 0.9021 (4) | 0.15099 (18) | 0.0926 (11) | |
H15A | 0.4990 | 0.9343 | 0.1834 | 0.139* | |
H15B | 0.5482 | 0.9428 | 0.1076 | 0.139* | |
H15C | 0.6652 | 0.9304 | 0.1651 | 0.139* | |
C16 | 0.6729 (2) | 0.6926 (3) | 0.09518 (12) | 0.0506 (6) | |
C17 | 0.6405 (3) | 0.6943 (3) | 0.02669 (12) | 0.0627 (7) | |
H17 | 0.5479 | 0.7215 | 0.0127 | 0.075* | |
C18 | 0.7425 (4) | 0.6565 (4) | −0.02107 (14) | 0.0776 (9) | |
H18 | 0.7187 | 0.6592 | −0.0668 | 0.093* | |
C19 | 0.8792 (3) | 0.6149 (3) | −0.00125 (17) | 0.0775 (9) | |
H19 | 0.9483 | 0.5888 | −0.0333 | 0.093* | |
C20 | 0.9130 (3) | 0.6121 (3) | 0.06599 (17) | 0.0778 (8) | |
H20 | 1.0052 | 0.5832 | 0.0798 | 0.093* | |
C21 | 0.8113 (3) | 0.6516 (3) | 0.11330 (14) | 0.0673 (8) | |
H21 | 0.8368 | 0.6507 | 0.1588 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0758 (13) | 0.0775 (13) | 0.0835 (13) | 0.0121 (12) | 0.0138 (11) | 0.0252 (11) |
O2 | 0.0585 (10) | 0.0754 (13) | 0.0606 (11) | 0.0183 (11) | 0.0000 (9) | −0.0036 (9) |
O3 | 0.0721 (14) | 0.1144 (17) | 0.0644 (13) | −0.0196 (12) | 0.0105 (11) | −0.0259 (12) |
N1 | 0.0475 (12) | 0.0677 (13) | 0.0484 (11) | 0.0056 (11) | 0.0101 (10) | 0.0027 (11) |
C1 | 0.0486 (15) | 0.0711 (16) | 0.0561 (14) | 0.0037 (13) | 0.0092 (13) | 0.0084 (12) |
C2 | 0.0474 (14) | 0.0853 (18) | 0.0450 (13) | 0.0030 (13) | 0.0032 (11) | 0.0022 (12) |
C3 | 0.0512 (14) | 0.0669 (17) | 0.0417 (13) | 0.0011 (13) | 0.0072 (11) | −0.0001 (12) |
C4 | 0.0484 (15) | 0.125 (3) | 0.0507 (15) | −0.0013 (16) | 0.0031 (13) | 0.0209 (16) |
C5 | 0.0437 (13) | 0.0592 (16) | 0.0465 (13) | 0.0034 (13) | −0.0024 (11) | −0.0052 (12) |
C6 | 0.0422 (12) | 0.0550 (15) | 0.0453 (12) | −0.0036 (12) | 0.0027 (11) | −0.0055 (11) |
C7 | 0.0555 (15) | 0.0637 (15) | 0.0504 (14) | −0.0022 (14) | −0.0008 (13) | 0.0005 (12) |
C8 | 0.0595 (16) | 0.084 (2) | 0.0530 (15) | −0.0111 (17) | 0.0138 (14) | −0.0057 (14) |
C9 | 0.0560 (16) | 0.081 (2) | 0.0731 (19) | −0.0016 (17) | 0.0237 (15) | −0.0143 (17) |
C10 | 0.0546 (16) | 0.0657 (18) | 0.0828 (19) | 0.0090 (14) | 0.0141 (14) | −0.0030 (15) |
C11 | 0.0444 (13) | 0.0554 (15) | 0.0561 (14) | −0.0012 (12) | 0.0047 (11) | −0.0018 (12) |
C12 | 0.0505 (15) | 0.0555 (15) | 0.0595 (15) | 0.0008 (13) | 0.0044 (12) | 0.0052 (13) |
C13 | 0.0501 (14) | 0.0849 (19) | 0.0464 (14) | −0.0044 (14) | 0.0119 (13) | −0.0012 (13) |
C14 | 0.0532 (15) | 0.0689 (18) | 0.0492 (14) | −0.0048 (14) | 0.0072 (12) | 0.0057 (14) |
C15 | 0.104 (3) | 0.086 (2) | 0.088 (2) | −0.001 (2) | 0.031 (2) | −0.0243 (18) |
C16 | 0.0479 (14) | 0.0538 (15) | 0.0501 (14) | −0.0026 (11) | 0.0102 (11) | 0.0004 (12) |
C17 | 0.0575 (16) | 0.0797 (19) | 0.0510 (15) | 0.0029 (16) | 0.0063 (14) | −0.0043 (13) |
C18 | 0.072 (2) | 0.102 (2) | 0.0588 (17) | −0.0123 (18) | 0.0165 (16) | −0.0200 (16) |
C19 | 0.0591 (19) | 0.085 (2) | 0.088 (2) | −0.0115 (15) | 0.0307 (18) | −0.0305 (17) |
C20 | 0.0534 (16) | 0.085 (2) | 0.095 (2) | 0.0042 (16) | 0.0102 (17) | −0.0033 (17) |
C21 | 0.0496 (15) | 0.086 (2) | 0.0662 (16) | −0.0025 (15) | 0.0058 (14) | 0.0015 (14) |
O1—C12 | 1.203 (3) | C8—H8 | 0.9300 |
O2—C5 | 1.206 (3) | C9—C10 | 1.380 (4) |
O3—C14 | 1.201 (3) | C9—H9 | 0.9300 |
N1—C5 | 1.378 (3) | C10—C11 | 1.381 (3) |
N1—C12 | 1.385 (3) | C10—H10 | 0.9300 |
N1—C13 | 1.444 (3) | C11—C12 | 1.484 (3) |
C1—C14 | 1.489 (4) | C13—C14 | 1.507 (4) |
C1—C4 | 1.534 (4) | C13—H13A | 0.9700 |
C1—C2 | 1.553 (3) | C13—H13B | 0.9700 |
C1—H1 | 0.9800 | C15—H15A | 0.9600 |
C2—C3 | 1.550 (4) | C15—H15B | 0.9600 |
C2—H2A | 0.9700 | C15—H15C | 0.9599 |
C2—H2B | 0.9700 | C16—C21 | 1.375 (4) |
C3—C15 | 1.504 (4) | C16—C17 | 1.387 (3) |
C3—C16 | 1.503 (3) | C17—C18 | 1.376 (4) |
C3—C4 | 1.557 (4) | C17—H17 | 0.9301 |
C4—H4A | 0.9700 | C18—C19 | 1.372 (5) |
C4—H4B | 0.9700 | C18—H18 | 0.9300 |
C5—C6 | 1.477 (3) | C19—C20 | 1.366 (4) |
C6—C11 | 1.373 (3) | C19—H19 | 0.9300 |
C6—C7 | 1.371 (3) | C20—C21 | 1.373 (4) |
C7—C8 | 1.385 (3) | C20—H20 | 0.9299 |
C7—H7 | 0.9300 | C21—H21 | 0.9300 |
C8—C9 | 1.368 (4) | ||
C5—N1—C12 | 112.1 (2) | C11—C10—C9 | 116.7 (3) |
C5—N1—C13 | 122.1 (2) | C11—C10—H10 | 121.6 |
C12—N1—C13 | 125.8 (2) | C9—C10—H10 | 121.6 |
C14—C1—C4 | 118.1 (2) | C6—C11—C10 | 121.3 (2) |
C14—C1—C2 | 114.8 (2) | C6—C11—C12 | 108.5 (2) |
C4—C1—C2 | 89.97 (19) | C10—C11—C12 | 130.2 (3) |
C14—C1—H1 | 110.8 | O1—C12—N1 | 125.2 (2) |
C4—C1—H1 | 110.8 | O1—C12—C11 | 129.5 (2) |
C2—C1—H1 | 110.8 | N1—C12—C11 | 105.3 (2) |
C3—C2—C1 | 90.15 (19) | N1—C13—C14 | 113.3 (2) |
C3—C2—H2A | 113.6 | N1—C13—H13A | 108.9 |
C1—C2—H2A | 113.6 | C14—C13—H13A | 108.9 |
C3—C2—H2B | 113.6 | N1—C13—H13B | 108.9 |
C1—C2—H2B | 113.6 | C14—C13—H13B | 108.9 |
H2A—C2—H2B | 110.9 | H13A—C13—H13B | 107.7 |
C15—C3—C16 | 109.6 (2) | O3—C14—C1 | 124.8 (2) |
C15—C3—C2 | 112.1 (2) | O3—C14—C13 | 120.6 (2) |
C16—C3—C2 | 115.9 (2) | C1—C14—C13 | 114.6 (2) |
C15—C3—C4 | 112.9 (2) | C3—C15—H15A | 109.5 |
C16—C3—C4 | 115.9 (2) | C3—C15—H15B | 109.5 |
C2—C3—C4 | 89.22 (19) | H15A—C15—H15B | 109.5 |
C1—C4—C3 | 90.59 (19) | C3—C15—H15C | 109.5 |
C1—C4—H4A | 113.5 | H15A—C15—H15C | 109.5 |
C3—C4—H4A | 113.5 | H15B—C15—H15C | 109.5 |
C1—C4—H4B | 113.5 | C21—C16—C17 | 117.1 (2) |
C3—C4—H4B | 113.5 | C21—C16—C3 | 122.4 (2) |
H4A—C4—H4B | 110.8 | C17—C16—C3 | 120.4 (2) |
O2—C5—N1 | 124.5 (2) | C18—C17—C16 | 121.5 (3) |
O2—C5—C6 | 129.1 (2) | C18—C17—H17 | 119.3 |
N1—C5—C6 | 106.4 (2) | C16—C17—H17 | 119.3 |
C11—C6—C7 | 121.9 (2) | C19—C18—C17 | 120.0 (3) |
C11—C6—C5 | 107.7 (2) | C19—C18—H18 | 120.0 |
C7—C6—C5 | 130.4 (2) | C17—C18—H18 | 120.0 |
C6—C7—C8 | 116.9 (2) | C20—C19—C18 | 119.4 (3) |
C6—C7—H7 | 121.5 | C20—C19—H19 | 120.3 |
C8—C7—H7 | 121.5 | C18—C19—H19 | 120.3 |
C9—C8—C7 | 121.2 (2) | C19—C20—C21 | 120.3 (3) |
C9—C8—H8 | 119.4 | C19—C20—H20 | 119.9 |
C7—C8—H8 | 119.4 | C21—C20—H20 | 119.9 |
C8—C9—C10 | 121.9 (2) | C20—C21—C16 | 121.8 (3) |
C8—C9—H9 | 119.0 | C20—C21—H21 | 119.1 |
C10—C9—H9 | 119.0 | C16—C21—H21 | 119.1 |
C14—C1—C2—C3 | 119.2 (2) | C13—N1—C12—O1 | 1.5 (4) |
C4—C1—C2—C3 | −2.1 (2) | C5—N1—C12—C11 | −1.4 (3) |
C1—C2—C3—C15 | −112.4 (2) | C13—N1—C12—C11 | −178.3 (2) |
C1—C2—C3—C16 | 120.7 (2) | C6—C11—C12—O1 | −179.6 (3) |
C1—C2—C3—C4 | 2.0 (2) | C10—C11—C12—O1 | −0.3 (5) |
C14—C1—C4—C3 | −116.3 (2) | C6—C11—C12—N1 | 0.2 (3) |
C2—C1—C4—C3 | 2.1 (2) | C10—C11—C12—N1 | 179.6 (3) |
C15—C3—C4—C1 | 111.7 (3) | C5—N1—C13—C14 | −71.0 (3) |
C16—C3—C4—C1 | −120.7 (2) | C12—N1—C13—C14 | 105.6 (3) |
C2—C3—C4—C1 | −2.1 (2) | C4—C1—C14—O3 | −6.1 (4) |
C12—N1—C5—O2 | −175.9 (2) | C2—C1—C14—O3 | −110.3 (3) |
C13—N1—C5—O2 | 1.1 (4) | C4—C1—C14—C13 | 172.4 (3) |
C12—N1—C5—C6 | 2.0 (3) | C2—C1—C14—C13 | 68.1 (3) |
C13—N1—C5—C6 | 179.0 (2) | N1—C13—C14—O3 | −25.3 (4) |
O2—C5—C6—C11 | 176.0 (2) | N1—C13—C14—C1 | 156.1 (2) |
N1—C5—C6—C11 | −1.8 (3) | C15—C3—C16—C21 | 93.4 (3) |
O2—C5—C6—C7 | −3.4 (4) | C2—C3—C16—C21 | −138.5 (3) |
N1—C5—C6—C7 | 178.8 (2) | C4—C3—C16—C21 | −35.8 (4) |
C11—C6—C7—C8 | −0.9 (3) | C15—C3—C16—C17 | −82.3 (3) |
C5—C6—C7—C8 | 178.4 (2) | C2—C3—C16—C17 | 45.8 (4) |
C6—C7—C8—C9 | 0.2 (4) | C4—C3—C16—C17 | 148.5 (3) |
C7—C8—C9—C10 | 0.5 (4) | C21—C16—C17—C18 | 0.0 (4) |
C8—C9—C10—C11 | −0.4 (4) | C3—C16—C17—C18 | 176.0 (3) |
C7—C6—C11—C10 | 1.0 (4) | C16—C17—C18—C19 | 0.6 (5) |
C5—C6—C11—C10 | −178.5 (2) | C17—C18—C19—C20 | −0.3 (5) |
C7—C6—C11—C12 | −179.6 (2) | C18—C19—C20—C21 | −0.5 (5) |
C5—C6—C11—C12 | 0.9 (3) | C19—C20—C21—C16 | 1.2 (5) |
C9—C10—C11—C6 | −0.3 (4) | C17—C16—C21—C20 | −0.9 (4) |
C9—C10—C11—C12 | −179.6 (3) | C3—C16—C21—C20 | −176.7 (3) |
C5—N1—C12—O1 | 178.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O2i | 0.97 | 2.48 | 3.322 (3) | 146 |
C2—H2B···O2i | 0.97 | 2.49 | 3.435 (3) | 164 |
C17—H17···Cg3ii | 0.93 | 2.85 | 3.730 (3) | 158 |
Symmetry codes: (i) x, y+1/2, −z+1/2; (ii) x+1/2, −y, −z. |
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