Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022999/sg2038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022999/sg2038Isup2.hkl |
CCDC reference: 613813
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.002 Å
- R factor = 0.055
- wR factor = 0.159
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.36 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT731_ALERT_1_C Bond Calc 0.832(19), Rep 0.834(9) ...... 2.11 su-Rat O2 -H2A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.832(19), Rep 0.834(9) ...... 2.11 su-Rat O2 -H2A 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
C17H21NO2 | F(000) = 292 |
Mr = 271.35 | Dx = 1.163 Mg m−3 |
Triclinic, P1 | Melting point: 325 K |
a = 5.8024 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8867 (17) Å | Cell parameters from 2358 reflections |
c = 12.5346 (19) Å | θ = 2.6–26.6° |
α = 93.980 (3)° | µ = 0.08 mm−1 |
β = 90.847 (3)° | T = 292 K |
γ = 100.955 (3)° | Block, colorless |
V = 775.2 (2) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 3416 independent reflections |
Radiation source: fine-focus sealed tube | 2423 reflections with I > 2σ(I)' |
Graphite monochromator | Rint = 0.057 |
φ and ω scans | θmax = 27.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −7→7 |
Tmin = 0.978, Tmax = 0.985 | k = −14→14 |
7457 measured reflections | l = −16→16 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0876P)2] where P = (Fo2 + 2Fc2)/3 |
3416 reflections | (Δ/σ)max = 0.002 |
190 parameters | Δρmax = 0.20 e Å−3 |
2 restraints | Δρmin = −0.22 e Å−3 |
Experimental. 1H NMR (CDCl3, 400 MHz): 8.41 (s, 2H, O—H), 6.90–6.94 (t, 4H, Ph—H), 6.75 (d, 2H, Ph—H), 4.10 (s, 8H, N—CH2), 2.27 (s, 3H, N—CH3). |
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 | ||
N1 | 0.3533 (2) | 0.25651 (10) | 0.55805 (10) | 0.0510 (3) | |
O1 | 0.1354 (2) | 0.42854 (11) | 0.64974 (9) | 0.0692 (4) | |
H1 | 0.177 (4) | 0.3796 (17) | 0.6036 (13) | 0.104* | |
O2 | 0.1181 (2) | 0.40206 (10) | 0.41050 (10) | 0.0677 (4) | |
H2A | 0.033 (3) | 0.4478 (18) | 0.3865 (17) | 0.102* | |
C1 | 0.4075 (3) | 0.33426 (14) | 0.74673 (13) | 0.0543 (4) | |
C2 | 0.4814 (3) | 0.30243 (16) | 0.84495 (14) | 0.0646 (4) | |
H2 | 0.6079 | 0.2614 | 0.8470 | 0.078* | |
C3 | 0.3768 (3) | 0.32853 (15) | 0.93997 (13) | 0.0641 (4) | |
C4 | 0.1870 (3) | 0.38733 (16) | 0.93425 (14) | 0.0694 (5) | |
H4 | 0.1109 | 0.4052 | 0.9966 | 0.083* | |
C5 | 0.1074 (3) | 0.42020 (16) | 0.83819 (14) | 0.0686 (5) | |
H5 | −0.0207 | 0.4600 | 0.8365 | 0.082* | |
C6 | 0.2162 (3) | 0.39451 (13) | 0.74482 (12) | 0.0548 (4) | |
C7 | 0.4652 (4) | 0.2919 (2) | 1.04508 (15) | 0.0906 (6) | |
H7A | 0.4146 | 0.2033 | 1.0501 | 0.136* | |
H7B | 0.4034 | 0.3366 | 1.1032 | 0.136* | |
H7C | 0.6336 | 0.3125 | 1.0486 | 0.136* | |
C8 | 0.5256 (3) | 0.30827 (17) | 0.64320 (13) | 0.0622 (4) | |
H8A | 0.6209 | 0.3856 | 0.6222 | 0.075* | |
H8B | 0.6287 | 0.2495 | 0.6540 | 0.075* | |
C9 | 0.2360 (4) | 0.12917 (16) | 0.57710 (15) | 0.0857 (6) | |
H9A | 0.3480 | 0.0746 | 0.5733 | 0.129* | |
H9B | 0.1137 | 0.1004 | 0.5237 | 0.129* | |
H9C | 0.1693 | 0.1289 | 0.6467 | 0.129* | |
C10 | 0.4577 (3) | 0.26228 (16) | 0.45199 (12) | 0.0591 (4) | |
H10A | 0.5726 | 0.2081 | 0.4471 | 0.071* | |
H10B | 0.5389 | 0.3474 | 0.4436 | 0.071* | |
C11 | 0.2774 (3) | 0.22288 (13) | 0.36344 (12) | 0.0533 (4) | |
C12 | 0.2688 (3) | 0.11365 (14) | 0.29788 (12) | 0.0620 (4) | |
H12 | 0.3820 | 0.0653 | 0.3086 | 0.074* | |
C13 | 0.0997 (3) | 0.07340 (15) | 0.21726 (13) | 0.0665 (5) | |
C14 | −0.0649 (3) | 0.14720 (16) | 0.20286 (13) | 0.0681 (5) | |
H14 | −0.1807 | 0.1226 | 0.1495 | 0.082* | |
C15 | −0.0622 (3) | 0.25694 (15) | 0.26582 (13) | 0.0619 (4) | |
H15 | −0.1756 | 0.3050 | 0.2546 | 0.074* | |
C16 | 0.1086 (3) | 0.29518 (13) | 0.34535 (12) | 0.0530 (4) | |
C17 | 0.0997 (5) | −0.04558 (19) | 0.14717 (17) | 0.0981 (7) | |
H17A | −0.0464 | −0.0686 | 0.1072 | 0.147* | |
H17B | 0.1185 | −0.1119 | 0.1912 | 0.147* | |
H17C | 0.2270 | −0.0317 | 0.0987 | 0.147* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0517 (7) | 0.0449 (7) | 0.0583 (7) | 0.0120 (5) | 0.0045 (6) | 0.0082 (5) |
O1 | 0.0865 (8) | 0.0671 (7) | 0.0638 (7) | 0.0451 (6) | −0.0137 (6) | −0.0071 (5) |
O2 | 0.0805 (8) | 0.0507 (6) | 0.0773 (8) | 0.0303 (6) | −0.0136 (6) | −0.0035 (5) |
C1 | 0.0487 (8) | 0.0485 (8) | 0.0653 (9) | 0.0089 (6) | −0.0066 (7) | 0.0037 (7) |
C2 | 0.0581 (9) | 0.0614 (10) | 0.0764 (11) | 0.0148 (8) | −0.0093 (8) | 0.0126 (8) |
C3 | 0.0714 (11) | 0.0533 (9) | 0.0634 (10) | 0.0013 (8) | −0.0073 (8) | 0.0069 (7) |
C4 | 0.0821 (12) | 0.0605 (10) | 0.0634 (10) | 0.0120 (9) | 0.0018 (9) | −0.0052 (8) |
C5 | 0.0722 (11) | 0.0622 (10) | 0.0739 (11) | 0.0257 (8) | −0.0053 (9) | −0.0112 (8) |
C6 | 0.0604 (9) | 0.0429 (8) | 0.0614 (9) | 0.0143 (7) | −0.0093 (7) | −0.0028 (6) |
C7 | 0.1024 (15) | 0.0938 (15) | 0.0727 (12) | 0.0075 (12) | −0.0111 (11) | 0.0209 (11) |
C8 | 0.0491 (8) | 0.0715 (10) | 0.0704 (10) | 0.0212 (8) | −0.0023 (8) | 0.0100 (8) |
C9 | 0.1305 (18) | 0.0498 (10) | 0.0715 (12) | 0.0012 (10) | 0.0148 (12) | 0.0090 (8) |
C10 | 0.0541 (9) | 0.0630 (9) | 0.0660 (10) | 0.0217 (7) | 0.0089 (7) | 0.0134 (8) |
C11 | 0.0575 (9) | 0.0495 (8) | 0.0577 (8) | 0.0176 (7) | 0.0113 (7) | 0.0144 (7) |
C12 | 0.0796 (11) | 0.0532 (9) | 0.0621 (10) | 0.0305 (8) | 0.0182 (9) | 0.0141 (8) |
C13 | 0.0939 (13) | 0.0487 (9) | 0.0590 (10) | 0.0162 (9) | 0.0142 (9) | 0.0082 (7) |
C14 | 0.0767 (11) | 0.0644 (10) | 0.0605 (10) | 0.0080 (9) | 0.0007 (8) | 0.0013 (8) |
C15 | 0.0636 (10) | 0.0615 (10) | 0.0645 (10) | 0.0214 (8) | −0.0003 (8) | 0.0055 (8) |
C16 | 0.0595 (9) | 0.0438 (7) | 0.0587 (9) | 0.0158 (7) | 0.0078 (7) | 0.0077 (6) |
C17 | 0.149 (2) | 0.0655 (12) | 0.0828 (13) | 0.0311 (13) | 0.0123 (13) | −0.0063 (10) |
N1—C8 | 1.458 (2) | C8—H8A | 0.9700 |
N1—C9 | 1.461 (2) | C8—H8B | 0.9700 |
N1—C10 | 1.4692 (18) | C9—H9A | 0.9600 |
O1—C6 | 1.3742 (18) | C9—H9B | 0.9600 |
O1—H1 | 0.829 (9) | C9—H9C | 0.9600 |
O2—C16 | 1.3661 (17) | C10—C11 | 1.497 (2) |
O2—H2A | 0.834 (9) | C10—H10A | 0.9700 |
C1—C2 | 1.386 (2) | C10—H10B | 0.9700 |
C1—C6 | 1.393 (2) | C11—C12 | 1.390 (2) |
C1—C8 | 1.511 (2) | C11—C16 | 1.393 (2) |
C2—C3 | 1.381 (2) | C12—C13 | 1.386 (2) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—C4 | 1.378 (2) | C13—C14 | 1.377 (3) |
C3—C7 | 1.513 (2) | C13—C17 | 1.514 (2) |
C4—C5 | 1.377 (2) | C14—C15 | 1.383 (2) |
C4—H4 | 0.9300 | C14—H14 | 0.9300 |
C5—C6 | 1.375 (2) | C15—C16 | 1.381 (2) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C7—H7A | 0.9600 | C17—H17A | 0.9600 |
C7—H7B | 0.9600 | C17—H17B | 0.9600 |
C7—H7C | 0.9600 | C17—H17C | 0.9600 |
C8—N1—C9 | 111.19 (13) | N1—C9—H9B | 109.5 |
C8—N1—C10 | 111.85 (11) | H9A—C9—H9B | 109.5 |
C9—N1—C10 | 111.69 (12) | N1—C9—H9C | 109.5 |
C6—O1—H1 | 104.6 (15) | H9A—C9—H9C | 109.5 |
C16—O2—H2A | 111.3 (16) | H9B—C9—H9C | 109.5 |
C2—C1—C6 | 117.65 (15) | N1—C10—C11 | 112.23 (12) |
C2—C1—C8 | 123.26 (14) | N1—C10—H10A | 109.2 |
C6—C1—C8 | 119.08 (14) | C11—C10—H10A | 109.2 |
C3—C2—C1 | 123.35 (15) | N1—C10—H10B | 109.2 |
C3—C2—H2 | 118.3 | C11—C10—H10B | 109.2 |
C1—C2—H2 | 118.3 | H10A—C10—H10B | 107.9 |
C4—C3—C2 | 117.04 (16) | C12—C11—C16 | 117.72 (15) |
C4—C3—C7 | 121.81 (17) | C12—C11—C10 | 122.05 (14) |
C2—C3—C7 | 121.14 (17) | C16—C11—C10 | 120.22 (13) |
C5—C4—C3 | 121.43 (16) | C13—C12—C11 | 123.12 (15) |
C5—C4—H4 | 119.3 | C13—C12—H12 | 118.4 |
C3—C4—H4 | 119.3 | C11—C12—H12 | 118.4 |
C6—C5—C4 | 120.43 (16) | C14—C13—C12 | 117.18 (15) |
C6—C5—H5 | 119.8 | C14—C13—C17 | 121.74 (19) |
C4—C5—H5 | 119.8 | C12—C13—C17 | 121.08 (17) |
O1—C6—C5 | 119.69 (14) | C13—C14—C15 | 121.64 (17) |
O1—C6—C1 | 120.23 (14) | C13—C14—H14 | 119.2 |
C5—C6—C1 | 120.08 (15) | C15—C14—H14 | 119.2 |
C3—C7—H7A | 109.5 | C16—C15—C14 | 120.05 (15) |
C3—C7—H7B | 109.5 | C16—C15—H15 | 120.0 |
H7A—C7—H7B | 109.5 | C14—C15—H15 | 120.0 |
C3—C7—H7C | 109.5 | O2—C16—C15 | 122.47 (13) |
H7A—C7—H7C | 109.5 | O2—C16—C11 | 117.23 (14) |
H7B—C7—H7C | 109.5 | C15—C16—C11 | 120.29 (14) |
N1—C8—C1 | 111.24 (12) | C13—C17—H17A | 109.5 |
N1—C8—H8A | 109.4 | C13—C17—H17B | 109.5 |
C1—C8—H8A | 109.4 | H17A—C17—H17B | 109.5 |
N1—C8—H8B | 109.4 | C13—C17—H17C | 109.5 |
C1—C8—H8B | 109.4 | H17A—C17—H17C | 109.5 |
H8A—C8—H8B | 108.0 | H17B—C17—H17C | 109.5 |
N1—C9—H9A | 109.5 | ||
C6—C1—C2—C3 | −0.7 (2) | C8—N1—C10—C11 | −173.56 (12) |
C8—C1—C2—C3 | 178.55 (15) | C9—N1—C10—C11 | 61.09 (17) |
C1—C2—C3—C4 | 1.2 (2) | N1—C10—C11—C12 | −112.58 (15) |
C1—C2—C3—C7 | −179.85 (15) | N1—C10—C11—C16 | 66.44 (18) |
C2—C3—C4—C5 | −0.9 (2) | C16—C11—C12—C13 | −0.9 (2) |
C7—C3—C4—C5 | −179.89 (16) | C10—C11—C12—C13 | 178.18 (13) |
C3—C4—C5—C6 | 0.2 (3) | C11—C12—C13—C14 | 0.3 (2) |
C4—C5—C6—O1 | −179.66 (14) | C11—C12—C13—C17 | 179.29 (15) |
C4—C5—C6—C1 | 0.3 (2) | C12—C13—C14—C15 | 0.1 (2) |
C2—C1—C6—O1 | 179.87 (14) | C17—C13—C14—C15 | −178.90 (16) |
C8—C1—C6—O1 | 0.6 (2) | C13—C14—C15—C16 | 0.1 (2) |
C2—C1—C6—C5 | −0.1 (2) | C14—C15—C16—O2 | −179.34 (14) |
C8—C1—C6—C5 | −179.37 (15) | C14—C15—C16—C11 | −0.7 (2) |
C9—N1—C8—C1 | −69.72 (17) | C12—C11—C16—O2 | 179.75 (12) |
C10—N1—C8—C1 | 164.65 (13) | C10—C11—C16—O2 | 0.7 (2) |
C2—C1—C8—N1 | 135.25 (15) | C12—C11—C16—C15 | 1.1 (2) |
C6—C1—C8—N1 | −45.55 (19) | C10—C11—C16—C15 | −178.00 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.83 (1) | 1.90 (1) | 2.6594 (15) | 152 (2) |
O1—H1···O2 | 0.83 (1) | 2.47 (2) | 2.9910 (17) | 121 (2) |
C8—H8A···O2i | 0.97 | 2.57 | 3.540 (2) | 173 |
O2—H2A···O1ii | 0.83 (1) | 1.88 (1) | 2.7065 (15) | 170 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |