Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001365/at2207sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001365/at2207Isup2.hkl |
CCDC reference: 642891
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.064
- wR factor = 0.236
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C16
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 26.95 From the CIF: _reflns_number_total 3130 From the CIF: _diffrn_reflns_limit_ max hkl 10. 8. 28. From the CIF: _diffrn_reflns_limit_ min hkl 0. 0. -28. TEST1: Expected hkl limits for theta max Calculated maximum hkl 10. 9. 30. Calculated minimum hkl -10. -9. -30. PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CAD-4-PC Software (Enraf–Nonius, 1992); cell refinement: CAD-4-PC Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
C16H16N2O2 | F(000) = 568 |
Mr = 268.31 | Dx = 1.223 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 8.5850 (17) Å | θ = 1.7–27.0° |
b = 7.1820 (14) Å | µ = 0.08 mm−1 |
c = 23.786 (5) Å | T = 293 K |
β = 96.35 (3)° | Block, yellow |
V = 1457.6 (5) Å3 | 0.25 × 0.20 × 0.18 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.021 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 1.7° |
Graphite monochromator | h = 0→10 |
ω scans | k = 0→8 |
3335 measured reflections | l = −28→28 |
3130 independent reflections | 3 standard reflections every 100 reflections |
1342 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.236 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1245P)2 + 0.0362P] where P = (Fo2 + 2Fc2)/3 |
3130 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.23 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 | 0.1433 (4) | 1.0886 (5) | −0.05903 (13) | 0.0670 (8) | |
C2 | 0.2483 (4) | 1.1680 (5) | −0.01796 (15) | 0.0768 (9) | |
H2 | 0.2729 | 1.2938 | −0.0196 | 0.080* | |
C3 | 0.3165 (3) | 1.0583 (5) | 0.02560 (13) | 0.0695 (9) | |
H3 | 0.3875 | 1.1108 | 0.0535 | 0.080* | |
C4 | 0.2800 (3) | 0.8691 (4) | 0.02827 (12) | 0.0617 (8) | |
C5 | 0.1750 (4) | 0.7935 (4) | −0.01451 (12) | 0.0653 (8) | |
H5 | 0.1509 | 0.6673 | −0.0136 | 0.080* | |
C6 | 0.1061 (4) | 0.9022 (5) | −0.05809 (12) | 0.0698 (9) | |
H6 | 0.0358 | 0.8505 | −0.0864 | 0.080* | |
C7 | 0.3722 (4) | 0.4621 (4) | 0.12301 (12) | 0.0638 (8) | |
C8 | 0.5295 (4) | 0.4046 (4) | 0.13398 (13) | 0.0682 (8) | |
H8 | 0.6024 | 0.4422 | 0.1101 | 0.080* | |
C9 | 0.5760 (3) | 0.2922 (4) | 0.18014 (13) | 0.0651 (8) | |
C10 | 0.4628 (3) | 0.2340 (4) | 0.21488 (12) | 0.0651 (8) | |
H10 | 0.4926 | 0.1578 | 0.2458 | 0.080* | |
C11 | 0.3051 (3) | 0.2893 (4) | 0.20349 (13) | 0.0647 (8) | |
C12 | 0.2619 (3) | 0.4008 (4) | 0.15772 (13) | 0.0673 (8) | |
H12 | 0.1576 | 0.4360 | 0.1497 | 0.080* | |
C13 | 0.3459 (3) | 0.7516 (4) | 0.07781 (12) | 0.0615 (8) | |
C14 | 0.4314 (5) | 0.8501 (5) | 0.12721 (14) | 0.0900 (11) | |
H14A | 0.4691 | 0.7607 | 0.1555 | 0.080* | |
H14B | 0.3617 | 0.9356 | 0.1428 | 0.080* | |
H14C | 0.5185 | 0.9172 | 0.1151 | 0.080* | |
C15 | 0.1860 (4) | 0.2223 (5) | 0.24078 (14) | 0.0885 (11) | |
H15A | 0.2371 | 0.1475 | 0.2708 | 0.080* | |
H15B | 0.1079 | 0.1492 | 0.2188 | 0.080* | |
H15C | 0.1371 | 0.3274 | 0.2565 | 0.080* | |
C16 | 0.7449 (4) | 0.2316 (5) | 0.19295 (15) | 0.0878 (11) | |
H16A | 0.7556 | 0.1548 | 0.2262 | 0.080* | |
H16B | 0.8106 | 0.3394 | 0.1993 | 0.080* | |
H16C | 0.7758 | 0.1622 | 0.1615 | 0.080* | |
N1 | 0.0686 (3) | 1.2085 (5) | −0.10508 (13) | 0.0804 (8) | |
N2 | 0.3202 (3) | 0.5776 (3) | 0.07516 (10) | 0.0688 (7) | |
O1 | 0.1035 (3) | 1.3728 (5) | −0.10528 (13) | 0.1193 (11) | |
O2 | −0.0281 (3) | 1.1373 (4) | −0.14001 (11) | 0.1054 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0629 (18) | 0.077 (2) | 0.0629 (18) | 0.0080 (17) | 0.0162 (15) | 0.0079 (17) |
C2 | 0.075 (2) | 0.065 (2) | 0.091 (2) | −0.0046 (17) | 0.0113 (19) | 0.0079 (19) |
C3 | 0.0670 (19) | 0.066 (2) | 0.073 (2) | −0.0013 (16) | −0.0014 (16) | −0.0013 (17) |
C4 | 0.0620 (17) | 0.064 (2) | 0.0605 (18) | 0.0002 (15) | 0.0113 (14) | −0.0071 (15) |
C5 | 0.078 (2) | 0.0588 (18) | 0.0591 (18) | 0.0004 (16) | 0.0078 (15) | −0.0045 (15) |
C6 | 0.072 (2) | 0.083 (2) | 0.0537 (17) | 0.0005 (18) | 0.0057 (15) | −0.0030 (16) |
C7 | 0.072 (2) | 0.0564 (17) | 0.0601 (18) | 0.0002 (15) | −0.0039 (15) | −0.0043 (14) |
C8 | 0.068 (2) | 0.0676 (19) | 0.0683 (19) | −0.0023 (16) | 0.0060 (15) | −0.0035 (16) |
C9 | 0.0641 (19) | 0.0603 (18) | 0.0686 (19) | 0.0070 (15) | −0.0023 (15) | −0.0103 (16) |
C10 | 0.072 (2) | 0.0613 (19) | 0.0607 (17) | 0.0025 (16) | 0.0008 (15) | −0.0069 (14) |
C11 | 0.0649 (19) | 0.0599 (18) | 0.0682 (19) | −0.0047 (15) | 0.0031 (15) | −0.0060 (16) |
C12 | 0.0612 (18) | 0.069 (2) | 0.0695 (18) | 0.0009 (16) | −0.0011 (15) | −0.0044 (17) |
C13 | 0.0636 (17) | 0.061 (2) | 0.0585 (18) | 0.0011 (15) | 0.0024 (14) | −0.0047 (14) |
C14 | 0.119 (3) | 0.072 (2) | 0.074 (2) | −0.004 (2) | −0.013 (2) | −0.0058 (18) |
C15 | 0.079 (2) | 0.099 (3) | 0.088 (2) | −0.002 (2) | 0.0134 (19) | 0.010 (2) |
C16 | 0.073 (2) | 0.094 (3) | 0.094 (2) | 0.019 (2) | −0.0005 (18) | −0.009 (2) |
N1 | 0.0684 (18) | 0.091 (2) | 0.083 (2) | 0.0113 (17) | 0.0167 (15) | 0.0185 (19) |
N2 | 0.0766 (17) | 0.0618 (17) | 0.0654 (16) | 0.0012 (13) | −0.0044 (12) | −0.0006 (13) |
O1 | 0.105 (2) | 0.101 (2) | 0.147 (3) | −0.0019 (18) | −0.0092 (17) | 0.0456 (19) |
O2 | 0.108 (2) | 0.124 (2) | 0.0791 (17) | 0.0113 (17) | −0.0112 (15) | 0.0125 (16) |
C1—C6 | 1.377 (4) | C10—C11 | 1.408 (4) |
C1—C2 | 1.378 (4) | C10—H10 | 0.9300 |
C1—N1 | 1.482 (4) | C11—C12 | 1.369 (4) |
C2—C3 | 1.379 (4) | C11—C15 | 1.505 (4) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—C4 | 1.397 (4) | C13—N2 | 1.269 (4) |
C3—H3 | 0.9300 | C13—C14 | 1.493 (4) |
C4—C5 | 1.393 (4) | C14—H14A | 0.9600 |
C4—C13 | 1.508 (4) | C14—H14B | 0.9600 |
C5—C6 | 1.377 (4) | C14—H14C | 0.9600 |
C5—H5 | 0.9300 | C15—H15A | 0.9600 |
C6—H6 | 0.9300 | C15—H15B | 0.9600 |
C7—C12 | 1.395 (4) | C15—H15C | 0.9600 |
C7—C8 | 1.409 (4) | C16—H16A | 0.9600 |
C7—N2 | 1.439 (4) | C16—H16B | 0.9600 |
C8—C9 | 1.386 (4) | C16—H16C | 0.9600 |
C8—H8 | 0.9300 | N1—O1 | 1.217 (4) |
C9—C10 | 1.407 (4) | N1—O2 | 1.220 (4) |
C9—C16 | 1.512 (4) | ||
C6—C1—C2 | 121.7 (3) | C12—C11—C15 | 120.9 (3) |
C6—C1—N1 | 119.7 (3) | C10—C11—C15 | 119.9 (3) |
C2—C1—N1 | 118.6 (3) | C11—C12—C7 | 120.9 (3) |
C1—C2—C3 | 119.1 (3) | C11—C12—H12 | 119.6 |
C1—C2—H2 | 120.5 | C7—C12—H12 | 119.6 |
C3—C2—H2 | 120.5 | N2—C13—C14 | 125.0 (3) |
C2—C3—C4 | 120.7 (3) | N2—C13—C4 | 117.7 (3) |
C2—C3—H3 | 119.6 | C14—C13—C4 | 117.3 (3) |
C4—C3—H3 | 119.6 | C13—C14—H14A | 109.5 |
C5—C4—C3 | 118.4 (3) | C13—C14—H14B | 109.5 |
C5—C4—C13 | 120.6 (3) | H14A—C14—H14B | 109.5 |
C3—C4—C13 | 120.9 (3) | C13—C14—H14C | 109.5 |
C6—C5—C4 | 121.2 (3) | H14A—C14—H14C | 109.5 |
C6—C5—H5 | 119.4 | H14B—C14—H14C | 109.5 |
C4—C5—H5 | 119.4 | C11—C15—H15A | 109.5 |
C1—C6—C5 | 118.8 (3) | C11—C15—H15B | 109.5 |
C1—C6—H6 | 120.6 | H15A—C15—H15B | 109.5 |
C5—C6—H6 | 120.6 | C11—C15—H15C | 109.5 |
C12—C7—C8 | 119.8 (3) | H15A—C15—H15C | 109.5 |
C12—C7—N2 | 118.6 (3) | H15B—C15—H15C | 109.5 |
C8—C7—N2 | 121.5 (3) | C9—C16—H16A | 109.5 |
C9—C8—C7 | 120.3 (3) | C9—C16—H16B | 109.5 |
C9—C8—H8 | 119.9 | H16A—C16—H16B | 109.5 |
C7—C8—H8 | 119.9 | C9—C16—H16C | 109.5 |
C8—C9—C10 | 118.8 (3) | H16A—C16—H16C | 109.5 |
C8—C9—C16 | 120.9 (3) | H16B—C16—H16C | 109.5 |
C10—C9—C16 | 120.3 (3) | O1—N1—O2 | 123.6 (3) |
C9—C10—C11 | 121.0 (3) | O1—N1—C1 | 118.7 (3) |
C9—C10—H10 | 119.5 | O2—N1—C1 | 117.7 (3) |
C11—C10—H10 | 119.5 | C13—N2—C7 | 119.4 (3) |
C12—C11—C10 | 119.2 (3) |