Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007385/hg6148sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007385/hg6148Isup2.hkl |
CCDC reference: 270444
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.076
- wR factor = 0.228
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C15
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.107 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.862(19) ...... 2.11 su-Rat O2 -H2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.862(19) ...... 2.11 su-Rat O2 -H2 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C17H18N2O2 | F(000) = 600 |
Mr = 282.33 | Dx = 1.237 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1484 reflections |
a = 4.9264 (19) Å | θ = 4.7–45.4° |
b = 28.000 (11) Å | µ = 0.08 mm−1 |
c = 11.098 (4) Å | T = 293 K |
β = 97.957 (7)° | Block, colorless |
V = 1516.1 (10) Å3 | 0.35 × 0.33 × 0.08 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 3116 independent reflections |
Radiation source: fine-focus sealed tube | 1720 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.107 |
φ and ω scans | θmax = 26.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −6→6 |
Tmin = 0.972, Tmax = 0.994 | k = −34→35 |
8199 measured reflections | l = −13→7 |
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)] = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.228 | w = 1/[σ2(Fo2) + (0.1071P)2 where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.004 |
3116 reflections | Δρmax = 0.25 e Å−3 |
205 parameters | Δρmin = −0.22 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 |
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 | 0.7881 (5) | 0.27046 (8) | 0.86197 (18) | 0.0655 (7) | |
O2 | 0.9434 (5) | 0.26408 (8) | 0.5039 (2) | 0.0640 (7) | |
N1 | 0.6670 (5) | 0.23717 (9) | 0.6786 (2) | 0.0448 (7) | |
N2 | 0.4978 (5) | 0.20445 (8) | 0.7234 (2) | 0.0458 (7) | |
C1 | 0.8110 (7) | 0.26850 (10) | 0.7534 (3) | 0.0437 (8) | |
C2 | 0.9947 (6) | 0.30130 (9) | 0.6980 (2) | 0.0420 (7) | |
C3 | 1.1170 (8) | 0.33746 (12) | 0.7725 (3) | 0.0642 (10) | |
H3 | 1.0738 | 0.3406 | 0.8511 | 0.077* | |
C4 | 1.3014 (9) | 0.36891 (13) | 0.7321 (3) | 0.0797 (13) | |
H4 | 1.3806 | 0.3929 | 0.7834 | 0.096* | |
C5 | 1.3678 (8) | 0.36471 (12) | 0.6161 (3) | 0.0667 (10) | |
H5 | 1.4927 | 0.3857 | 0.5892 | 0.080* | |
C6 | 1.2504 (7) | 0.32976 (11) | 0.5406 (3) | 0.0540 (8) | |
H6 | 1.2963 | 0.3270 | 0.4624 | 0.065* | |
C7 | 1.0618 (6) | 0.29816 (10) | 0.5799 (2) | 0.0421 (7) | |
C8 | 0.3585 (6) | 0.17941 (10) | 0.6420 (3) | 0.0488 (8) | |
H8 | 0.3765 | 0.1854 | 0.5611 | 0.059* | |
C9 | 0.1715 (6) | 0.14170 (10) | 0.6686 (3) | 0.0465 (8) | |
C10 | 0.1451 (7) | 0.12720 (11) | 0.7857 (3) | 0.0581 (9) | |
H10 | 0.2427 | 0.1428 | 0.8519 | 0.070* | |
C11 | −0.0252 (8) | 0.08971 (11) | 0.8044 (3) | 0.0614 (9) | |
H11 | −0.0380 | 0.0803 | 0.8837 | 0.074* | |
C12 | −0.1772 (7) | 0.06565 (11) | 0.7100 (3) | 0.0532 (8) | |
C13 | −0.1576 (8) | 0.08177 (15) | 0.5945 (3) | 0.0807 (12) | |
H13 | −0.2625 | 0.0673 | 0.5285 | 0.097* | |
C14 | 0.0139 (9) | 0.11894 (14) | 0.5744 (3) | 0.0786 (12) | |
H14 | 0.0229 | 0.1288 | 0.4951 | 0.094* | |
C15 | −0.3609 (8) | 0.02365 (13) | 0.7284 (4) | 0.0687 (10) | |
C16 | −0.3912 (11) | 0.01337 (18) | 0.8571 (5) | 0.1174 (18) | |
H16A | −0.2240 | −0.0002 | 0.8976 | 0.136* | |
H16B | −0.5387 | −0.0088 | 0.8598 | 0.136* | |
H16C | −0.4303 | 0.0425 | 0.8971 | 0.136* | |
C17 | −0.2493 (13) | −0.02080 (16) | 0.6705 (6) | 0.124 (2) | |
H17A | −0.0760 | −0.0296 | 0.7156 | 0.131* | |
H17B | −0.2257 | −0.0139 | 0.5879 | 0.131* | |
H17C | −0.3765 | −0.0467 | 0.6719 | 0.131* | |
H1 | 0.677 (7) | 0.2384 (11) | 0.603 (3) | 0.061 (10)* | |
H2 | 1.051 (8) | 0.2590 (15) | 0.450 (3) | 0.113 (16)* | |
H15 | −0.534 (7) | 0.0213 (12) | 0.667 (3) | 0.075 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1012 (19) | 0.0708 (15) | 0.0290 (12) | −0.0182 (13) | 0.0251 (12) | −0.0065 (10) |
O2 | 0.0870 (18) | 0.0756 (15) | 0.0362 (12) | −0.0240 (13) | 0.0322 (12) | −0.0164 (11) |
N1 | 0.0605 (17) | 0.0506 (15) | 0.0270 (13) | −0.0062 (12) | 0.0191 (12) | 0.0032 (11) |
N2 | 0.0616 (16) | 0.0470 (14) | 0.0313 (13) | 0.0009 (12) | 0.0155 (12) | 0.0046 (11) |
C1 | 0.065 (2) | 0.0416 (16) | 0.0277 (15) | 0.0046 (14) | 0.0170 (14) | −0.0019 (12) |
C2 | 0.0560 (18) | 0.0417 (16) | 0.0299 (15) | 0.0041 (14) | 0.0110 (13) | 0.0005 (12) |
C3 | 0.104 (3) | 0.0577 (19) | 0.0329 (17) | −0.0191 (19) | 0.0158 (18) | −0.0045 (14) |
C4 | 0.121 (3) | 0.073 (2) | 0.043 (2) | −0.040 (2) | 0.004 (2) | −0.0018 (17) |
C5 | 0.080 (3) | 0.070 (2) | 0.049 (2) | −0.0271 (19) | 0.0033 (18) | 0.0125 (17) |
C6 | 0.063 (2) | 0.063 (2) | 0.0389 (17) | −0.0076 (17) | 0.0179 (15) | 0.0053 (15) |
C7 | 0.0571 (19) | 0.0389 (15) | 0.0319 (15) | 0.0028 (14) | 0.0111 (13) | −0.0007 (12) |
C8 | 0.062 (2) | 0.0543 (18) | 0.0322 (16) | 0.0009 (16) | 0.0132 (14) | 0.0048 (13) |
C9 | 0.0573 (19) | 0.0496 (17) | 0.0331 (16) | 0.0025 (14) | 0.0085 (14) | 0.0004 (12) |
C10 | 0.084 (2) | 0.0543 (19) | 0.0378 (18) | −0.0148 (18) | 0.0158 (17) | −0.0082 (14) |
C11 | 0.079 (2) | 0.062 (2) | 0.048 (2) | −0.0120 (19) | 0.0255 (18) | 0.0012 (16) |
C12 | 0.054 (2) | 0.0543 (18) | 0.053 (2) | −0.0024 (15) | 0.0115 (16) | −0.0038 (16) |
C13 | 0.085 (3) | 0.102 (3) | 0.051 (2) | −0.038 (2) | −0.005 (2) | −0.006 (2) |
C14 | 0.099 (3) | 0.099 (3) | 0.0342 (19) | −0.032 (2) | −0.0027 (19) | 0.0040 (18) |
C15 | 0.066 (2) | 0.063 (2) | 0.076 (3) | −0.0115 (19) | 0.006 (2) | 0.001 (2) |
C16 | 0.137 (5) | 0.106 (4) | 0.113 (4) | −0.050 (3) | 0.026 (3) | 0.021 (3) |
C17 | 0.153 (5) | 0.066 (3) | 0.188 (6) | −0.023 (3) | 0.046 (5) | −0.023 (3) |
O1—C1 | 1.227 (3) | C9—C14 | 1.370 (4) |
O2—C7 | 1.351 (3) | C9—C10 | 1.384 (4) |
O2—H2 | 0.862 (19) | C10—C11 | 1.378 (4) |
N1—C1 | 1.341 (4) | C10—H10 | 0.9300 |
N1—N2 | 1.377 (3) | C11—C12 | 1.376 (4) |
N1—H1 | 0.85 (3) | C11—H11 | 0.9300 |
N2—C8 | 1.268 (4) | C12—C13 | 1.374 (5) |
C1—C2 | 1.482 (4) | C12—C15 | 1.515 (5) |
C2—C3 | 1.390 (4) | C13—C14 | 1.378 (5) |
C2—C7 | 1.398 (4) | C13—H13 | 0.9300 |
C3—C4 | 1.384 (5) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.484 (6) |
C4—C5 | 1.376 (5) | C15—C17 | 1.537 (6) |
C4—H4 | 0.9300 | C15—H15 | 1.02 (4) |
C5—C6 | 1.364 (4) | C16—H16A | 0.9600 |
C5—H5 | 0.9300 | C16—H16B | 0.9600 |
C6—C7 | 1.396 (4) | C16—H16C | 0.9600 |
C6—H6 | 0.9300 | C17—H17A | 0.9600 |
C8—C9 | 1.458 (4) | C17—H17B | 0.9600 |
C8—H8 | 0.9300 | C17—H17C | 0.9600 |
C7—O2—H2 | 107 (3) | C11—C10—H10 | 119.9 |
C1—N1—N2 | 120.5 (2) | C9—C10—H10 | 119.9 |
C1—N1—H1 | 119 (2) | C12—C11—C10 | 122.5 (3) |
N2—N1—H1 | 120 (2) | C12—C11—H11 | 118.8 |
C8—N2—N1 | 114.0 (2) | C10—C11—H11 | 118.8 |
O1—C1—N1 | 121.6 (3) | C13—C12—C11 | 116.6 (3) |
O1—C1—C2 | 121.6 (3) | C13—C12—C15 | 120.1 (3) |
N1—C1—C2 | 116.8 (2) | C11—C12—C15 | 123.3 (3) |
C3—C2—C7 | 117.6 (3) | C12—C13—C14 | 121.5 (3) |
C3—C2—C1 | 116.4 (3) | C12—C13—H13 | 119.2 |
C7—C2—C1 | 126.0 (3) | C14—C13—H13 | 119.2 |
C4—C3—C2 | 121.4 (3) | C9—C14—C13 | 121.5 (3) |
C4—C3—H3 | 119.3 | C9—C14—H14 | 119.2 |
C2—C3—H3 | 119.3 | C13—C14—H14 | 119.2 |
C5—C4—C3 | 120.0 (3) | C16—C15—C12 | 115.0 (4) |
C5—C4—H4 | 120.0 | C16—C15—C17 | 109.5 (4) |
C3—C4—H4 | 120.0 | C12—C15—C17 | 108.5 (3) |
C6—C5—C4 | 120.0 (3) | C16—C15—H15 | 116.5 (19) |
C6—C5—H5 | 120.0 | C12—C15—H15 | 115 (2) |
C4—C5—H5 | 120.0 | C17—C15—H15 | 89.0 (19) |
C5—C6—C7 | 120.5 (3) | C15—C16—H16A | 109.5 |
C5—C6—H6 | 119.8 | C15—C16—H16B | 109.5 |
C7—C6—H6 | 119.8 | H16A—C16—H16B | 109.5 |
O2—C7—C6 | 120.1 (3) | C15—C16—H16C | 109.5 |
O2—C7—C2 | 119.5 (3) | H16A—C16—H16C | 109.5 |
C6—C7—C2 | 120.5 (3) | H16B—C16—H16C | 109.5 |
N2—C8—C9 | 123.4 (3) | C15—C17—H17A | 109.5 |
N2—C8—H8 | 118.3 | C15—C17—H17B | 109.5 |
C9—C8—H8 | 118.3 | H17A—C17—H17B | 109.5 |
C14—C9—C10 | 117.6 (3) | C15—C17—H17C | 109.5 |
C14—C9—C8 | 119.3 (3) | H17A—C17—H17C | 109.5 |
C10—C9—C8 | 123.1 (3) | H17B—C17—H17C | 109.5 |
C11—C10—C9 | 120.2 (3) | ||
C1—N1—N2—C8 | 175.0 (3) | N1—N2—C8—C9 | 178.3 (2) |
N2—N1—C1—O1 | −3.2 (4) | N2—C8—C9—C14 | 175.1 (3) |
N2—N1—C1—C2 | 178.0 (2) | N2—C8—C9—C10 | −5.3 (5) |
O1—C1—C2—C3 | −6.5 (4) | C14—C9—C10—C11 | 2.9 (5) |
N1—C1—C2—C3 | 172.3 (3) | C8—C9—C10—C11 | −176.7 (3) |
O1—C1—C2—C7 | 171.3 (3) | C9—C10—C11—C12 | −0.8 (6) |
N1—C1—C2—C7 | −9.9 (4) | C10—C11—C12—C13 | −1.8 (5) |
C7—C2—C3—C4 | −0.8 (5) | C10—C11—C12—C15 | 178.6 (3) |
C1—C2—C3—C4 | 177.2 (3) | C11—C12—C13—C14 | 2.4 (6) |
C2—C3—C4—C5 | −0.1 (6) | C15—C12—C13—C14 | −178.0 (4) |
C3—C4—C5—C6 | 0.4 (6) | C10—C9—C14—C13 | −2.3 (6) |
C4—C5—C6—C7 | 0.2 (5) | C8—C9—C14—C13 | 177.3 (3) |
C5—C6—C7—O2 | 179.0 (3) | C12—C13—C14—C9 | −0.4 (7) |
C5—C6—C7—C2 | −1.3 (5) | C13—C12—C15—C16 | −172.9 (4) |
C3—C2—C7—O2 | −178.7 (3) | C11—C12—C15—C16 | 6.7 (6) |
C1—C2—C7—O2 | 3.4 (5) | C13—C12—C15—C17 | 64.1 (5) |
C3—C2—C7—C6 | 1.5 (4) | C11—C12—C15—C17 | −116.4 (4) |
C1—C2—C7—C6 | −176.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.85 (3) | 1.96 (3) | 2.630 (3) | 135 (3) |
O2—H2···O1i | 0.86 (2) | 1.82 (2) | 2.653 (3) | 161 (4) |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |